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Halloween Cross-Dressing Bash Ch. 01

By: BOSTONFICTIONWRITER



Bob went to the bathroom, locked the door, and sat on the closed toilet lid. He pulled the invitation from his wallet and unfolded it. Well worn from reading it over and again so many times, he had saved it hidden there in his wallet and in his back pocket since the beginning of September. He had received the invitation online and printed it out before deleting it, so that his wife wouldn't see it.

It excited him to read it. It excited him to think about attending the Halloween party. Reading this 8 x 11 piece of paper was one of the few things that gave him any real happiness. This invitation to the Halloween Bash gave him hope for a new beginning and another chapter in his life with the hope of making some new friends who shared his interest and desire to dress as a woman.

"Topsy Turvy invites you to our biggest and best cross-dressing dance of the year, The Happy Halloween Cross-Dressing Bash. This is your chance to come dressed as you really are. This is your chance to be yourself without embarrassment or ridicule. This is your chance to fit in with the rest of us and to shine. So, kick off your jeans and flannel shirts and leave your work boots home. Put on a dress, a wig, some makeup, and your highest high heels and come strut your stuff with us while dancing to the music, Honey."

They got his name and e-mail address from the query he sent online last year. He wanted to go last year, but had chickened out at the last minute. He had reserved his place and ordered and even paid for the ticket. He even went as far as to pick out the clothes, but he left them in the carriage in the aisle when he saw his friend, Jim and his wife enter the store, as he was nearing the register to pay for his selections.

He panicked and left in a mad rush without them seeing him, thank God. That was all he needed was for Jim to see him buying women's clothes. That was all he needed was for Jim to tell everyone that he was a cross-dresser. He was a big blabbermouth and would tease him unmercifully not realizing that what he thought was a joke and was innocent teasing was, in fact, actually the truth.

He'd never live it down. Never again could he go to the tavern for a beer while watching the game on the big screen. Never could he shoot pool with the guys or be invited over to their homes for a game of draw poker. He'd have to quit the bowling league, too. And they'd never allow him to coach another Little League or Pop Warner Football team; two things that he loved to do every year.

He couldn't imagine what the guys at work would say. They'd think him gay. They would never understand his need and desire to wear nice things and to dress as a woman. They'd laugh at him. He couldn't imagine what his minister would say to him about this. His life as he had known and loved it in this little community of closed minded and unforgiving Christians would be over.

He imagined Jim's conversation.

"Hey, Bob, where's Sheila?"

"She's home."

"Home?"

"Yeah, I'm here alone."

"Alone?"

"Yeah, I thought I'd do a little shopping and pick up a few things that I needed."

He imagined his friend peering in the carriage and picking up his items, a dress, pantyhose, shoes, a pocketbook, a bra, and panty.

"What's all this? This dress is huge. It would never fit Sheila. Are you buying clothes for your mother or are you a cross-dresser?"

"No, uhm, it's for the women's shelter. Yeah, that's it. They are in desperate need for clothes for when they have to go out and get dressed up for a job interview."

He imagined himself turning red with embarrassment. With guilt and shame written all over his face, he imagined himself stuttering with nothing to say to make Jim believe that he wasn't a cross-dresser. What was the use? He knew Jim would never believe him, which is why he fled the store. His friend would immediately know that he was lying.

There'd be no way to explain himself out of that one because Jim's wife, Connie, was best friends with Sheila, Bob's wife, and she'd tell her that she saw Bob shopping for women's clothes. Then, when he didn't give his wife the clothes, Sheila, of course, would think he was having an extra marital affair. 

He'd rather be deemed a cross-dresser than for his wife to think he was having an affair. He didn't know which was worse. Either way, she'd kill him. Either way, she'd divorce him. Either way, he was screwed.

He hated all the sneaking around just to buy an outfit for the Happy Halloween Cross-Dressing Bash. He had been so excited to attend and now to have all his excitement suddenly end was devastating. It was his fault. He hadn't really thought it through. What the Hell was he thinking shopping here in town anyway?

He should have shopped at a mall where no one knew him. Then, again, maybe he wanted to get caught. Maybe, he wanted all of this to be made public finally after spending a lifetime hiding the fact that he enjoyed wearing women's clothes. Maybe, he was just tired of not being himself and wanted to come out of the closet, so to speak.

So what if he enjoyed wearing women's clothes? He wasn't hurting anyone. He wasn't committing a crime. It was just something he enjoyed doing. People should mind their own business. How dare they put their morals and societal interpretations that forced him to conform to their standards and restricted him on how to act not only when in public but also even when in the privacy of his own home? He wished everyone would just leave him the Hell alone. This was his life to live and not theirs.

He'd even thought about ordering the clothes online, but what if his wife saw the credit card bill? What if the women's clothes came to his house when he was at work and his wife was home? How could he possibly explain that? Oh, my God! He was in a panic just thinking about what she would say and do. 

"Bob, a box from He/She Outfits came for you while you were at work," he imagined his wife confronting him at the door with a rolling pin as soon as he pulled in the driveway with his pickup truck.

"What? He/She Outfits. I don't know what you're talking about." Deny, deny, and deny, he thought to himself when in a jam, even if she's holding proof. "I'm tired. I just want to get a beer and watch some TV." 

"I should have known they weren't for me because you never buy me anything," she'd say showing her disappointment in that fact and in him. "Yet, I was so excited thinking that you bought me a gift and bought something for me that I opened the box. Can you imagine my surprise when I found these clothes? None of these clothes are my size. I take an 8/10 and these clothes are an 18. Can you explain this, Bob," she'd say holding up a dress that would surely swim on her petite frame, but coincidentally was plenty big enough to fit his fat body. "What the Hell is all this?"

"Explain what? There's nothing to explain. I didn't order that stuff. I don't know what you're talking about."

"Who did you buy these clothes for, Bob? Did you buy these clothes for your fat girlfriend? You'd better not have a girlfriend, fat or otherwise, Bob," he imagined her saying while tapping the rolling pin in the palm of her hand. "I won't tolerate you cheating on me after all I've done for you. I cook and clean for you and make you a good home. You'd better not have a girlfriend on the side."

"I have no idea what all these women's clothes are, Honey? I didn't order them," he'd say squeezing by her while pulling the dress from her hand.

Deflated that he'd have to return everything that he took the time to buy online, saddened that he now couldn't attend the Happy Halloween Cross-dressing Bash because he wouldn't have an outfit to wear, he imagined scooping up the women's clothes and stuffing them back in the box. 

"What are you going to do with all this, then?"

"I'll return them tomorrow," he'd say going in the house. "Obviously, it was delivered to the wrong address."

He thought about opening a post office box and have whatever he ordered online delivered there, but he lived in a small town and he knew all those who worked at the post office and they were all blabbermouths. Even though he didn't understand why people thought that men wearing women's clothes was perverted, even though he didn't believe he was doing anything wrong by buying women's clothes and having them delivered to his house or post office box, the mailman knew all the perverts in town and he didn't want to be known as one of them.

He had spent many a day gossiping to the mailman about this one and that one and he didn't want to be the mailman's gossip fodder for the remainder of his route for that day and the remainder of the year. It pained him to think of the mailman gossiping to his neighbors about him being a cross-dresser because of what was delivered to him in the mail.

He just wanted to be left alone to live his life the way he wanted to live it, only he couldn't. People couldn't mind their own business. People were always pointing their fingers and laughing at anyone who was the least bit different. What the Hell did they know? They didn't know him? They didn't know how he felt? How could they? If they did, maybe they'd understand. Well, he was glad that he wasn't like them. He was glad that he finally found something that made him happy, even if he had to sneak around to enjoy it and even if it was considered taboo and/or perverted.

Now, a year later, back in a different woman's clothing store and shopping for women's clothes again, he was having a panic attack. He couldn't breathe. He was so nervous, so guilty, and so afraid to be himself. Wearing dark glasses and a baseball cap, always ready to abandon his carriage and flee the store, he continually looked around the small store to see if he recognized anyone shopping. 

As soon as he grabbed a carriage and started shopping, his hands were shaking. Before he had picked out anything to put in his shopping cart, already, he feared taking his purchases to the register. As the anxiety that a thief must feel when about to shoplift, he felt as if he was doing something wrong. He felt everyone was staring at him. He felt everyone knew he was here buying clothes for himself. He felt that everyone knew he was a cross-dresser.

After not dressing as a woman for years, since before he was married, he had successfully fought the urge to dress up in women's clothes. Yet, always it was there. Once in a while he'd squeeze his fat ass in his wife's panties and wear them to work. Only, he always feared the embarrassment should he have an accident at work and have to be taken out by ambulance and driven to the hospital. He had women's clothes hidden all over the house, in the cellar, and in the garage when he needed to feel some comfort by wearing something nice, something soft, and something sexy next to his skin.

He imagined that the emergency medical technicians, doctors, and nurses at the emergency room saw it all, but this was a small town where everyone knew everyone and they all talked about everything to everyone. He could never live with that embarrassment and shame he'd feel should anyone in town discover that he enjoyed wearing women's clothes.

He'd have to move to get any peace after that. He'd be an outcast. He imagined the whole town turning against him and shunning him. He imagined mothers at Halloween pulling their children away from his house and passing it by completely. 

"Don't go to that house for candy, kids. Bob lives there and he's a very sick man who enjoys wearing women's clothes. Pervert," he'd hear his neighbors yell when he came to the door with his dish of candy to pass out to the kids, only to watch them walk by his house before throwing eggs at his windows.

Even now, years later, he couldn't pass by a lingerie counter without feeling the silk and satin panties. He loved how they felt. Women were so lucky. He wished they made men's underwear that felt as nice and as soft and that made him feel as sexy when wearing it. He couldn't pass by a rack of women's clothes without pausing to browse the merchandise while imagining how he'd look in this dress or that blouse or that skirt.

Now, having given into the urge of wearing women's clothes, safe within the acceptance that he'd surely receive at the Happy Halloween Cross-Dressing Bash, he was excited about attending and getting dressed as a woman without being made to feel foolish or being harshly judged and meanly ridiculed. He just wanted to go somewhere that he could dress as a woman without anyone making fun of him or looking at him like there was something wrong with him. He just wanted to experience, for once, what it would be like to see himself in the mirror while being completely dressed as a woman in public. He wanted to be accepted for who he truly was without having to hide, without having to lie, and without having to make excuses for his behavior.

In the next chapter Bob goes shopping for women's clothes.

*

Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued... 

Halloween Cross-Dressing Bash Ch. 02



Now, having given into the urge of wearing women's clothes, safe within the acceptance that he'd surely receive at the Happy Halloween Cross-Dressing Bash, he was excited about attending and getting dressed as a woman without being made to feel foolish or being harshly judged and meanly ridiculed. He just wanted to go somewhere that he could dress as a woman without anyone making fun of him or looking at him like there was something wrong with him. He just wanted to experience, for once, what it would be like to see himself in the mirror while being completely dressed as a woman in public. He wanted to be accepted for who he truly was without having to hide, without having to lie, and without having to make excuses for his behavior.

Finally, there was a place for him to go where he'd feel accepted. The Topsy Turvy Happy Halloween Cross-Dressing Bash, run and organized by cross-dressers for cross-dressers, he'd finally meet men who were just like him and who shared his need to dress as a woman. There was nothing else like it and he couldn't wait to go. Tickets were $30.00 a person and the invitation even read that he could bring his spouse or girlfriend or significant other to the event. Only, he had no one to bring. He was alone in his secret. 

He envied those men who had a woman by their side who understood their need to cross-dress. His wife would have a heart attack if he told her that he needed to dress as a woman. She'd never attend if he asked her to accompany him and would forbid him to go. She'd think he was insane and she'd divorce him for sure if he dressed and attended the event.

He hated the fact that he couldn't share something this big, something that was so important to him, and something that made him this happy with his wife. He hated having to sneak around. He hated feeling so guilty. He wished he could tell her. He wished she'd be supportive of his need to cross-dress. He felt so alone safeguarding his secret desire. Happy and excited, he was sad and guilty at the same time. He was miserable.

When they went to New York City, last year, they had seen a few cross-dressers and drag queens and she laughed at them and made fun of them to him. 

"Bob," she said squeezing his arm. "Look at that one. That's a man dressed as a woman, isn't it? How can someone so sick walk around like that in public? I'm so embarrassed for him. He looks nothing like a woman. It's so obvious that he's a man. He's not fooling anyone. What a bunch of faggots."

Her hostility towards them shocked him. What would she think of him if she knew that he shared their desire to dress as a woman? Would she think he was sick? Would she be embarrassed for him? Would she think he was a faggot, too?

He thought the cross-dressers looked pretty. He envied how they looked. He wished he were one of them and was free to be himself. He envied that they were so dressed in women's clothes and out walking about on a public street, when he was still hiding his secret desire to so dress. He wished he could be as brave and as true to himself as they were. He wished he was as free to express himself in that way.

She made him feel bad. She made him feel perverted. She made him feel dirty. She made him feel less than the man he truly was. She made him feel that he was a degenerate just because he wanted to feel feminine and pretty. There was just no way he could tell her, never mind asking her to attend the Topsy Turvy Happy Halloween Cross-Dressing Bash with him. He imagined the fight they'd have and her respect he'd lose.

"What? You want to dress up as a woman? You want to drag me to this perverted and sick dance with you? I'd be mortified. I'd be humiliated. Are you crazy? What is wrong with you? What are you gay? I married a gay man! I want a divorce."

He imagined her thinking that he suddenly lusted over men and not understanding what cross-dressing was about. Not necessarily sexual, not necessarily even a fetish or homosexual, cross-dressing, a behavior of transgender, does not always mean that the cross-dresser has a different gender from that assigned at birth. Only, how could he convince her of anything in her state of close mindedness?

She was as close minded about it, as were most people. She'd never understand. She'd hate him. She'd be hurt. She'd feel that she did something wrong. She'd feel that it was her fault that he wanted to dress as a woman. She'd feel it was all about her and not about him.

Bob didn't want to shock anyone. He didn't want to challenge social norms. He wasn't trying to make a statement. He didn't even want to pass as a woman by adopting her voice or mannerisms. By keeping his mustache and not shaving it off, without even realizing it, if anything he was genderfucking. He didn't even know what genderfucking was.

He was just an average guy who enjoyed the feeling of women's clothes against his skin. He liked how he looked when he was all dressed. That's all. He felt pretty, he felt sexy, and he was happy, and he only wished that he could experience that feeling more often.

Bob hid the bag of clothes away in the toolbox of his truck while waiting for his wife to go out and do her errands before bringing it in the house. He was excited to see his purchases again and to try them on to see if they all fit.

He was sweating he was so nervous. He had never done anything like this before and he was embarrassed, but excited at the same time. The saleswoman at the store, an attractive and heavyset woman, who was about his age, wouldn't leave him alone. He didn't know if she was hitting on him, was just trying to do her job and help him, thought he was a shoplifter because he was acting so nervous to arouse her suspicions or if she suspected that he was buying the clothes for himself and that he was a cross-dresser.

He figured he was just being paranoid. He figured she was just doing her job. He needed to calm down, relax, and have a good time picking out the outfit he'd wear to the ball. This was the beginning of a new chapter in his life.

He successfully avoided her by heading down different aisles whenever he spotted her heading in his direction. Then, as she neared, he tried not looking at her hoping that she'd head the other way and busy herself with another customer.

"Can I help you to find something?"

"What?"

"Do you need some help with sizes?"

"Oh, well, yeah, I think, uhm, maybe. It's my wife's birthday and—"

"What size does she take?"

"Size? Oh, I don't know. I didn't think to take her sizes with me. She's big, as big as I am." He was glad he didn't say as big as you are. Some woman, all women probably, are sensitive about their weight.

The saleswoman looked at him with a knowing look and he felt embarrassed. Was she looking at him because he was a typical guy who didn't know his wife's sizes? Was she looking at him because she could tell what size his wife would take by the size of him? Was she looking at him because she thought he was a potential shoplifter? Or was she looking at him because she suspected he was a cross-dresser. His palms were sweating and his pulse was racing. He figured she thought that he was a cross-dresser. Suddenly, he felt exactly how he hated others made him feel. He felt perverted.

He felt as if he was doing something wrong and maybe he was, but it was none of her business why he was there. As far as he was concerned, he was there to buy clothes for his wife. As far as she was concerned, he was just another customer with every right to be in her store to shop for whatever and for whomever.

He took a breath and tried to relax. He wanted to tell her that the clothes weren't for him, but he figured that would make her even more suspicious. Yet, what did it matter? He'd never see her, again. He traveled nearly clear across the state on the pretense of going to a monster truck show to shop for women's clothes. No one knew him here, he hoped.

"Well, if your wife is as heavy and as tall as you are, you'd want to go to the plus sizes that are on the other side of the store. These are the petite sizes."

Bob stood 5'8" and weighed about 200 pounds.

"Oh, okay."

She escorted him to the other side of the store and now that he was relaxed enough to take note of the woman who was helping him, he determined that they were both about the same size. She was pretty, much prettier than his wife. He felt better knowing that she could help him pick out the correct sizes he needed without making her think that the clothes were for him. Maybe, she'd even try the clothes on to model them for him. 

Nah, she'd never do that. It's probably against store policy. Besides, this wasn't Rodeo Drive. This wasn't a high end store where they had models to model the clothes while you lounged in a chair sipping champagne and comfortably waited for your wife or girlfriend or significant other to make her fashion selection and she wasn't Pretty Woman.

Suddenly, being in her company, he was horny. The more he interacted with her, the more he was attracted to her. Nonetheless, he felt conspicuous and uncomfortable being the only man in a woman's clothing store. Finally, he felt relieved when he saw that there were other salesclerks helping customers, too, and not just helping him. That made him feel better that he wasn't being singled out, but it was just store policy and helpful store clerks helping customers find what they needed.

"Are you shopping for pants, a skirt or a—"

"A dress," he said with a nervous smile. "She only wears dresses. She said that pants make her look fat and that dresses hide her weight more."

"Yeah, that's true, normally, but we have some slenderizing pantsuits that just came in for our Fall selection and they go on sale—" 

"Nah, she'll return it if I bought her pants. She never wears pants."

"Well, I have several racks of dresses. Do you know what colors she'd like? Does she like solids or prints or—"

"Solids and in a dark color, black, navy blue, brown or forest green because she says the darker colors make her look thinner."

She rifled through a rack and pulled out half a dozen dresses. Every dress was more than he wanted to spend. Some of the dresses were well over one hundred dollars, more than he paid for the last suit he bought to attend his friend's wedding.

"All of our dresses can be altered. We have a seamstress—"

"I like this one," he said pointing to a dark green one that had shiny gold buttons. He didn't even look at the others she had pulled from the rack. He acted as if he was afraid to even touch any of them. 

"You have good taste. This is a popular style and a very comfortable dress. Many of our customers choose this dress because it is roomy without looking baggy," she said twirling around with the dress held up to her before holding it up to him. Being blessed with abundant proportions, she was very curvaceous for a full figured woman. "And it just falls right because of the material," she said. "And the gold buttons dress it up a bit otherwise it would look a bit plain."

"It's not for me," he said taking a step back. "It's for my wife."

"I know that," she said giving him a sexy smile and a chuckle. "I'm just holding it up for size," she said taking a step towards him, "since you told me that your wife is about your size."

"Oh, okay. I'm just a little nervous being in a woman's clothing store without my wife. I'm more comfortable in Home Depot shopping for power tools," he said with a laugh.

"We are about the same size. Is your wife about my size?" She gave him a smile before slowing turning in each direction. Bob couldn't help but stare at her big breasts. They were huge.

"Yeah, she is, only she—" he paused embarrassed while holding his hands out in front of his chest and staring at her huge double D breasts. Certainly, she could suffocate someone with those weapons, but what a way to die. He imagined her hanging those huge hooters down over his face and sucking on them while she sat on his cock.

He imagined the conversation that his friends would have at his funeral should he meet with foul boob play.

"So, how did Bob die, anyway?"

"Bob was suffocated by big boobs, really big boobs, the lucky bastard, but he died with a smile on his face."

"Wow! What a way to go. When I die, I hope I go that way, with big boobs, really big boobs, suffocating the life out of me."

She looked down at her abundant cleavage before looking back up at him and catching him looking at her tits and giving him a sexy smile. 

"Not many women are as top heavy as I am. It's been a curse more than it has been a blessing. My husband left me for some flat chested bitch. Can you imagine passing up a steady diet of these big tits," she said raising her tits up with both her hands, "for a woman who has not much more than nipples?"

Top heavy? He didn't know why this woman didn't continually fall forward from the weight her her huge hooters. 

"No, I mean, yeah, he'd have to be crazy to pass up on those. Sorry," he said feeling a bit uncomfortable with the conversation and her forwardness. "I didn't mean to stare." He could feel his face turning a bright red.

Now, he was unable to remove the image that she had given him of her standing next to her ex-husband's flat chested girlfriend with her big tits casting a shadow over her feet. He imagined the two women standing side by side topless. It took all the control he had to wipe the smile from his face imagining her big, naked breasts.

"It's okay," she said. It's been years since we divorced." 

Still holding the dress up to him, she pressed one hand against his chest with her other hand pushed against his pelvis with her fingers only inches away from his cock. If he took one step to the left, her fingers would be in contact with his growing erection. There, he did, but just as he did, she handed him the dress. Darn.

"Thank you," he said accepting the dress from her.

"You can return it if it doesn't fit her. We can go a size smaller or a size larger. We have some in a size 16 and a size 20. And if she doesn't like the color, but likes the style we have the dress in brown, black, navy, and red. I'm sure she'll love it."

Bob looked at the price, $89.95. He could buy a nice fishing rod or a power tool for that. He calculated that his entire outfit he was wearing today, jeans, flannel shirt, work boots, and even his underwear didn't cost as much as this one dress.

"I can try it on for you, if you'd like and model it so that you can see how it would look on your wife."

"Really?" He couldn't believe his ears. Suddenly, he imagined her whipping off her dress and putting on this one right in front of him. "You can do that?"

In the next chapter Bob enjoys the show.

*

Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued...



Halloween Cross-Dressing Bash Ch. 03



She escorted him to the other side of the store and now that he was relaxed enough to take note of the woman who was helping him, he determined that they were both about the same size. She was pretty, much prettier than his wife. He felt better knowing that she could help him pick out the correct sizes he needed without making her think that the clothes were for him. Maybe, she'd even try the clothes on to model them for him.

Nah, she'd never do that. It's probably against store policy. Besides, this wasn't Rodeo Drive. This wasn't a high end store where they had models to model the clothes while you lounged in a chair sipping champagne and comfortably waited for your wife or girlfriend or significant other to make her fashion selection and she wasn't Pretty Woman.

"I can try it on for you, if you'd like and model it so that you can see how it would look on your wife."

"Really?" He couldn't believe his ears. Suddenly, he imagined her whipping off her dress and putting on this one right in front of him while he stood behind her with his cock planted between her ass checks helping to hold her big bra covered tits up and out of the way for her to fit in the dress. "You can really do that?"

"Sure, it's part of our personal service and what makes our store better than the competition. We pride ourselves on our customer service."

"You won't get in trouble? I mean it's not against store policy to model the clothes for me, is it? That would be great if you could do that."

"Well, if it is against store policy, it's my policy to break. I own the store," she smiled. "It's one of the benefits of being the boss."

"Oh, okay, sure. Yeah, I'd like to see the dress on you, that way I can tell how it would look on my wife."

"Follow me," she said and headed for the dressing room. "What's your name," she said turning to look at him.

"Bob."

"Pleased to meet you, Bob. I'm Gloria, but everyone calls me Glory," she said turning and stopping to shake hands with him.

"Glory? Why Glory?"

"Glory is the name of my store."

"Oh." Bob was so nervous walking in the women's clothing store that he didn't even notice the name on the store.

He stopped short as he neared the dressing room.

"It's okay, you can come inside. There's a sofa across from the three full sized mirrors where you can sit and wait for me to change."

Bob impatiently sat on the sofa while Gloria went in the dressing room to the right and pulled closed the curtain. Only, she didn't pull the curtain all the way closed and when Bob looked in the first mirror that was conveniently angled to the right and pointed at where she was changing, he could clearly see Gloria's reflection while she unzipped her dress.

She removed it from her shoulders and shimmied it down past her bust, wiggled it past her waist, and pulled it over her hips before stepping out of it and hanging it on a hanger. She stood in the dressing room in her white, full sized panty and big white bra with her back to him. She had a big, full, round and shapely ass. He couldn't believe what he was seeing. Immediately with the sight of her, he started developing an erection. He couldn't believe he was seeing Glory in her bra and panty. She was giving him an unbelievable strip tease show.

When she turned a little to the left, he could see the entire side of her bra and part of the front of her bra covered tits. Her tits were huge and she was wearing the biggest bra he had ever seen. He could only imagine what her tits looked like. Her bra cups were so round and so full with the tops of her breasts squished a bit together to form a long cleavage line. He imagined his cock fitting nicely in there and in between her breasts as she lowered her head down and licked the top of his penis before shooting load of cum in her mouth and all over her big tits. All she needed was a yellow caution sign, as her big, white bra looked like painted white scaffolding to support those big breasts.

He wished she wasn't wearing a bra. He wished he could see her tits, her areolas, and her nipples. He could only imagine what they looked like. No, he couldn't imagine what they looked like because, surely, he had never seen tits this big before. Only, as soon as he thought it, she did it. He couldn't believe his eyes when she reached around behind her, unhooked her bra, pushed the straps from her shoulders, removed her bra, and hung it on the hook. Oh, baby, there they were and they were magnificent.

Are you kidding me? Clearly, he had a good view of the entire side of her boob. If only she would turn a bit to the left, there, he saw her left breast, all of it. She had the biggest tits he had ever seen. For tits that were as big as hers, they didn't sag as much as he thought they would. They were spectacular. He imagined touching them, feeling them, caressing them, fondling them, sucking them, and fucking them before shooting a load of cum all over them.

Her areolas were as big around as saucers and she had these giant nipples that made his lips reflexively move in the shape of a goldfish's mouth when begging for food. Finally, she emerged from the dressing room wearing the dark green dress with the gold buttons. The dress looked a little like a uniform, but he liked it.

"What do you think," she said. She stood up on the platform that they have where the seamstress pins the hem of the dress to hem it. With a wide smile while holding up and out the hem of the dress, she twirled in front of him. From the low angle of the couch and in the relaxed vantage point of how he slouched down while sitting, he was treated to a complete up skirt view of her panty from camel toe to waistband. Was she purposely teasing him or did she just not know what she was doing? Whichever, she was driving him nuts.

"It looks good on you," he said barely able to speak after her sexy show. Unable to remove the vision of her up skirt and of her in her panties and bra and only removing that image to remember her giant naked breasts, he suddenly saw this saleswoman in a whole new light. He imagined calling home while spending the night at Gloria's house.

"Honey, I'm going to spend the night here," he'd say to his wife while Gloria sucked his cock and he felt her enormous tits and fingered her giant sized nipples. "They're having another truck show tomorrow, too, and Willie Nelson is giving a free concert and you know how much I love Wet Willie."

"I just love how this dress fits and falls. It's a real bargain for the money. She'll get years of use out of it." She laughed and a flash of red brightened her cheeks. "I had to remove my bra otherwise I'd never fit myself in the dress. Besides, the way this dress is cut, it squishes my tits so tight that I almost don't need any more support."

"I'll take it," he said. He just wanted to watch her change again. He hoped that she'd forget to close the curtain all the way, again. From where he was sitting, unless she looked at his reflection in the mirror, she couldn't see him.

"Great," she smiled. "Just give me a minute to change." She walked in the dressing room shouldering past the curtain without closing it at all this time. It was nearly halfway open and no matter where she stood in that tiny dressing room, he could clearly see all of her.

This time she took her time undressing and dressing giving him more of a prolonged show. With the curtain open a good two feet, how could she not know the curtain was open? How could she not know he could see her? Intently, he watched as she unzipped her dress. This time, instead of wiggling herself out of it, she lifted it from the hem and up and over her head.

With her dress covering her face, she turned to face him, her tits lifted high up and proud as she struggled to free herself from her dress. As if in slow motion, he watched her big boobs sway and bounce with the movement of her trying to free herself from the tight confines of the dress. It took all the self-control he possessed not to get up and offer to help her. 

"Here, let me hold your tits out of the way," he imagined saying to her as he touched, caressed, and felt her tits before falling to his knees and taking them in his mouth.

He couldn't believe it when she faced him topless with her head down while holding her bra and tightening her over the shoulder boulder strap holder.

Both of her breasts were totally exposed to him. She was topless and she was facing him. He saw everything through the mirror. Surely, she was doing this on purpose. Surely, she was flashing him her tits. Surely, she knew that he could see her breasts. How could she not know that he could see her? Hey, if she wanted to show him her big balloons, he was going to look and he did. He stared and he leered while smiling with the thought of spending some quality time alone with her and away from here with those huge knockers. 

Only, just as he thought that, she looked up, saw his reflection in the mirror, and caught him staring while smiling. She covered her tits with her hand and arm and snapped shut the curtain with a loud click. Oh, oh, now he was fucked. He was as embarrassed for himself as he was for her. He was such a fool. He just ruined a good thing. There goes his free wet Willie concert. Now what?

Maybe, she didn't know that the curtain was open. Yeah, right? He was certainly grateful for the show, as it had been a while since he had been intimate with his wife, and this saleswoman wasn't a bad looking woman. He couldn't take his eyes of her tits. It had been quite some time since he had been with a woman who had big tits, before he was married when he was dating his first girlfriend Kathy or Linda or Debbie. He couldn't remember her name. He only remembered feeling and sucking her big tits. He imagined Glory sucking his cock with him fondling her massive boobs while dressed in his forest green dress with the gold buttons.

Finally, she emerged again from the dressing room with her dress unzipped in the back. 

"I'm so sorry," she said. "I thought that I had closed the curtain all the way. You didn't see my, uhm, anything did you," she asked while biting her lip.

"I did. I'm the one who should apologize. I'm sorry. I was mesmerized. I couldn't take my eyes off your breasts. I've never seen tits so big."

"You saw my breasts?"

"Yes, and I'm sorry."

"I'm so embarrassed," she said turning red and breaking eye contact. "It's a bad habit, I guess. Normally, we don't allow men in the dressing room. Normally, it's just us girls in the dressing room and sometimes we don't even close the curtain. 

"Please don't be. Think of it as an artistic display. They truly are beautiful, works of art, actually."

"Really? Do you really think so? Oh, God, I'm so embarrassed. I hardly know you and you've already seen my breasts and are now talking about them." She looked at him and gave him a smile of embarrassment. "Do you really think my breasts are works of art?"

"Oh, yes, I do. They are quite spectacular. If I were an artist, I'd want to paint them. I am an amateur photographer, though. I would love to shoot them." 

"Yeah, I bet you would," she said with a smile.

"C'mon, it would be fun."

"Oh, I don't know about that," she said. "Maybe," she said giving him a sexy look. "Let me think about it. In the meantime, would you mind doing me," she said. 

All that he could imagine was pushing her down on the rug in the dressing room, stripping off her clothes, stripping off his clothes, struggling to remove that massive bra, and pulling down her white panty before mounting her and doing her. He'd hump her had, really hard, while leaning down to suck on her big nipples.

"I beg your pardon?"

"My dress," she said pointing to the zipper. "Would you mind doing me, I mean zipping me?" She turned her back to him flashing him the back of her wide bra and the top of her panty. He had a sudden urge to reach inside her dress and around her to feel her big breasts through her white bra.

"Oh, yeah, sure."

"Sorry, I don't realize what I say sometimes. Sometimes, my innocence gets me in trouble. Much like my little dress shop?"

"How do you mean?"

"Well, ever since I was a little girl, everyone called me Glory. I figured that'd be a great name for the dress shop. When I started this business, I couldn't afford much to lease, but I found this place, a little hole in the wall, much longer than it is wider. I wanted to call it Glory's Hole In The Wall, but the shop was so narrow, the words wouldn't fit and still maintain the city council's code for sign size. So, I named it Glory's Hole."

"Oh. Oh! I had no idea your shop was named, Glory's Hole," he said laughing.

"If I knew you a bit better, I'd tell you the other half of the story relating to the name of the shop and what my ex-husband tricked me to do, but it's a bit risqué and I'm embarrassed that I fell for it," she said with a sexy laugh. "I'm too trusting and it's only something that I would do. I should have known better," she said hanging his dress back on the hanger. "Okay, so we have the dress, what else do you need?"

"Well, now you have me more than curious about the other half of the story. Maybe if I spend more money in your store, you'll tell me the story. Let's see, I need shoes and a handbag. I want to buy her a whole outfit, soup to nuts."

She gave him a look that made him lift up his chin in defiance of her suspicion that he was a cross-dresser. Yet, maybe her look was that she had suddenly taken a sexual interest in him after accidentally on purpose flashing him her boobs and would, perhaps, share the rest of her story that related to the name of the shop and what her ex-husband had tricked her into doing while in the privacy of her bedroom.

In the next chapter Bob jumps at the chance to wet his Willie.

*

Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued...



Halloween Cross-Dressing Bash Ch. 04



"If I knew you a bit better, I'd tell you the other half of the story relating to the name of the shop and what my ex-husband tricked me to do, but it's a bit risqué and I'm embarrassed that I fell for it," she said with a sexy laugh. "I'm too trusting and it's only something that I would do. I should have known better," she said hanging his dress back on the hanger. "Okay, so we have the dress, what else do you need?"

"Well, now you have me more than curious about the other half of the story. Maybe if I spend more money in your store, you'll tell me the story. Let's see, I need shoes and a handbag. I want to buy her a whole outfit, soup to nuts."

She gave him a look that made him lift up his chin in defiance of her suspicion that he was a cross-dresser. Yet, maybe her look was that she had suddenly taken a sexual interest in him after accidentally on purpose flashing him her boobs and would, perhaps, share the rest of her story that related to the name of the shop and what her ex-husband had tricked her into doing. Maybe, she would tell him that sexy story in the privacy of her bedroom.

"Do you know what size shoe she takes?"

"That I know because she wears my slippers sometimes and they fit her perfectly. I take a size 9, so she must, too."

"Well, women's shoes fit a bit differently than men's shoes. If she fits in your men's size 9 a woman's size 10 would fit her." She looked at him and smiled.

She was prettier when she smiled. Certainly, she was much prettier than his wife. He wished his wife took as much pride in her appearance as this woman did. Now, after seeing her tits, he wished his wife had bigger and better tits. His wife's little A cuppers that sagged more than did her double D breasts.

"Oh, I didn't know that about women's shoes."

"Does she have a wide or narrow foot?"

"Wide, like me."

"Do you know if she prefers heels, flats or pumps?"

"Pumps? What's that?" Suddenly, he imagined humping her and pumping all the cum he had in her pussy and in her mouth.

"These are pumps," she said holding out a shoe to him.

"Yeah, I like those, I mean, I've seen her wear that type of shoe."

"Try this on to see if it fits."

"Gloria," he said taking a step back while putting up his hand as if it was a mini stop sign, "I'm not going to try on a woman's shoe. I'm not gay. Maybe you think I am, but I'm not one of those cross-dressers."

She shot him a look. He had over done the protesting and had aroused her suspicion. He could clearly see it in her eyes.

"No one will know, Bob. There's no one else here in the shoe department but you and me. Besides, the shoe is not for you, it's for your wife. Right?"

The way that she questioned him when she said the word, Right, made him think that she was on to him. Suddenly, he felt embarrassed. Suddenly, he wanted to escape her and her store. Then, he thought of the cross-dressers' ball. He fled the store last year when he saw his friend Jim and missed his opportunity to attend the dance; he regretted not buying his outfit and he wasn't going to do that again this year.

He suspected that she knew he was a cross-dresser. Yet, what did it matter? Apparently, whether he's buying the clothes for him or for his wife, she doesn't care who he is buying the clothes for, so long as he buys them. She just wants his sale. Whether he was gay or straight or even a cross-dresser, his money was good here.

"Yes, they are for her, of course," he said with half a smile. He wanted to punctuate what he said by saying that they definitely are not for me, but didn't. 

Bob sat on the little bench they had in the shoe department and unlaced his work boot. He felt foolish. He felt embarrassed and excited at the same time that he was about to try on a woman's shoe in front of a woman he barely knew. Normally, trying on women's clothes, even just women's shoes were something that he'd do in the privacy of his home. He could feel his cock swell with the thoughts of wearing the green dress with the gold buttons that he had chosen with these brown pumps. He couldn't wait to try the dress on when he got home to see how pretty and sexy he'd look for the dance.

He couldn't believe his eyes when she squatted down to fit the shoe on his foot and remained there while he pretended to look at the shoe on his foot, but instead looked at her. She rewarded him with a down dress peek at her bra and an up skirt peek at her panty at the same time. Even though he had already seen her in her bra and panty, this sight of looking down her dress at her long line of cleavage and seeing her bright, white cotton panty was so much more exciting and so much more erotic. He couldn't help himself from looking between her thighs at her panty covered camel toe and stare down her dress at her big, white bra. How could she not know she was flashing him? Was she doing this accidentally without realizing that he could see her bra and her panty or was she doing this on purpose?

This woman was driving him wild with sexual desire for her. With the attention she had suddenly shown him by flashing him her big tits in the dressing room and now flashing him her panty and bra, he didn't care if she flashed him by accident or on purpose so long as she continued flashing him. Then, he stood only, now, he had an erection. He saw her cast her glance at the obvious bulge in his pants. She showed him a satisfied smile. A bit unsteady on the pump, the shoe fit him well, albeit a little tight. He figured he'd stick the thing in the vice once he got home and leave it in there overnight to stretch it wider.

"How do they fit?"

"Yeah, the shoe fits me good," he said walking past her and turning so she couldn't see him pushing his erection down hoping to make it look less obvious. "They should fit her."

He didn't know how women wore these little shoes. They offered no support whatsoever. His work boot was much more comfortable. His work boot even had a steel toe. These things were like wearing molded plastic. He knew that he'd never be able to walk in the high heels, but he wanted something that made him feel taller than his 5'8" height. The pumps were the perfect choice.

"Okay, the handbags are over here," she said already walking away and ahead of him.

"Wait, how much are the shoes?"

"These are..." She turned to face him, accepted the shoe from him, and turned it over to see the price tag. "These are $49.95."

"Wow, fifty bucks. My work boots only cost me thirty bucks on sale at Wal-Mart and they have way more leather than those little pump things. They even have a steel toe."

"Well, this isn't Wal-Mart," she said laughing, "and your work boots aren't as fashionable as this darling little pump things," she said with another laugh. "And unless you, I mean, your wife intends on playing soccer while wearing these pumps, you, I mean, she won't have the need for a steel toe."

She walked him over to the handbags and began picking out a selection of bags that complimented his dress. Immediately he fell in love with a dark brown, imitation alligator purse. It reminded him of his shotgun case, only not nearly as big.

"That one," he said pointing, and acting again as if he was almost afraid to touch it. "I've seen her looking at the same exact purse. "How much is that purse?"

"I wish all my customers were quick shoppers like you men," she said with a chuckle. "I'd have my merchandise flying out the door, instead of collecting dust on racks. I can't tell you how much time I've spent with women only to have them walk out the door without buying anything. Yet, once a man walks into my store, I know I'll have a sale."

"Well, men like to just be done with shopping. I'm the same way at Home Depot. I don't like to wander. I know what I need and I know where to get it. I go get it and bring it up to the counter to pay for it. Shopping to me is a complete waste of time and not fun at all. I don't like aimlessly wandering around the store. I'm rather be home watching the football game on TV. I'm not much of a window shopper.

He lied. He was having a blast shopping for his outfit. This was the most fun he has had seen he first received his invitation to the Topsy Turvy Halloween Cross-Dressing Bash. Picking out the dress, the shoes, and now the pocketbook was so very exciting. He couldn't wait to try them all on. He couldn't wait to see what he'd look like. He couldn't wait.

"This one is" she said reaching inside the pocketbook for the tag, "$69.95."

"Wow. My wallet only cost my five bucks. How much am I up to now?"

"Well, the dress is ninety, the shoes, fifty, and the purse seventy, your total is two hundred and ten dollars, less fifteen cents, so two hundred nine and eighty-five cents."

"Don't you always have a sale on women's clothes?"

"Not today," she said giving him her best smile.

"Oh, and I need those stocking things, you know the ones like long underwear but for women that football players wear under their uniforms."

"Pantyhose?"

"Yeah, that's it. I need a pair of those. Better give me two pair incase one tears. She never cuts her damn toenails. She's always clawing my legs in bed." Satisfied with his imagined quickness, he thought that was a believable touch to say about his wife having long toenails that needed to be cut and was a good reason to buy the second pair of pantyhose.

She helped him pick out two pair of taupe queen-sized pantyhose. She opened one of the packages and held one pair up to his waist.

"You can never tell about these things. Some brands give you more length than you need and others don't give you enough." 

He couldn't believe it when she put a hand to his crotch to hold the pantyhose steady and in place to see the fit. Her touch was gentle yet strong. Her hand and fingers felt good against his balls. He imagined her jerking him off. He imagined her unzipping him, pulling off his pants, and helping him on with his pantyhose. Now, that would be the kind of customer service that he needed right now. He imagined parading around in front of her in his pantyhose with his cock sticking straight out and her staring at it before reaching her hand inside, grabbing it and moving it to try and make it fit better in the pantyhose without being so conspicuous.

"Sorry," she said smiling. "I'm used to fitting women. I can't believe I did that, touched you like that," she said turning a bit red again. "I'm so embarrassed. See, that's what I mean about me. I do something so innocent, not realizing that it can be taken so sexually." 

He liked that about her. He liked how she blurted things and did things without realizing the sexual implications of them and then once realizing what she had just done, blushed over what she did. Had he not been a man, had he been a woman, he would have realized that she knew exactly what she was doing. She was fishing and he was the big catch of the day. With her big tits as bait, she was reeling him in, hook, line, and sinker.

"Well, I guess that's it," he said taking a step towards the register.

"What about accessories?"

"Accessories? You mean a belt and a hat? No, I don't look good in hats. I mean, she doesn't wear hats."

"No, there's no need for a belt with that dress and I wasn't necessarily talking about a hat for you or for her," she said with a little laugh. "What I meant by accessories was what about earrings and/or a bracelet. We have a great selection of costume jewelry and I'm sure you could find something to accessorized your outfit selection and complete your wardrobe to dress it up a bit more."

Outfit selections...complete your wardrobe. That's what he liked about shopping for women's clothes. The words they used always gave him a full image of their fashion. Guys don't talk about outfits and wardrobe, they just buy their jeans and shirt, shut up about it, and take them home. Women were so much creative about their clothes. Albeit more expensive, definitely, it was more fun shopping here than at Wal-Mart.

"Yeah, I could buy her some accessories, too."

They walked over to the jewelry counter together and picked out earrings and a bracelet that matched."

"These are nice," she said holding up dangling earrings that weren't so big that they'd be annoying to wear. First she held them up to her ear and looked at herself with them in the mirror. Then, she held them up to his ear. Instantly, he recoiled.

"Yeah, I like those," he said not even examining them, but just looking and pointing.

"And I have a bracelet that matches the earrings."

"Perfect."

Not real gold, they were more costume jewelry and he bought both the earrings and the bracelet for $29.95.

"Will that be all?"

"Yeah, I guess I'm done spending my money on my wife."

"I'm sure she'll love everything," she said shooting him a smile and giggle. 

"What about lingerie?"

"Lingerie?"

"Bra and panty?"

"Oh, yeah, I would have forgotten had you not mentioned that. Definitely, I'm going to need to buy a bra and a panty," he said giving her a hopeful look.

"Sorry, but I can't model those for you," she said with a sexy laugh and giving him a long pause before speaking. "It's against the health code. Besides, you've already seen more of me than you should have and certainly more of me than many of my boyfriends do on our first date. I'm still embarrassed to think that you saw my—"

"Please don't be embarrassed. It's already gone from my mind."

In fact the only two things that filled his mind were those two massive tits. Once he saw them, he couldn't stop imagining touching them, feeling them, caressing them, holding them, and sucking them, while she fucked him after sucked his cock. She had beautiful, big breasts and if he didn't realize it before, he knew now that he was a breast man.

"Well, you've already modeled the bra for me," he said with a laugh, "why not model the panty, too."

She ignored his remark while walking ahead of him to the lingerie area.

He wondered if there wasn't a health code about trying on underwear if she'd model them for him. He wondered if she'd leave the curtain partially open while removing her bra again and trying on the new one before emerging wearing her panty and bra or just her bra or just her panty. He imagined her asking him, how do they feel? He imagined reaching out his hands and touching her and feeling her body through her sexy lingerie while she groped and fondled and rubbed his cock through his pantyhose.

She escorted him to the lingerie counter where Bob picked three panties, one in pink, one in blue, and one in bright white. He loved how they felt. He so wanted to hold them up to his face and run them down his check and along his neck. Maybe, later when he was home alone, he'd do that while stroking his cock. Then, he picked a white 40 C bra. He loved handling the panties and bra, especially after having seen Gloria in her panty and bra. Now, he imagined he was touching her panty and bra.

"Well, I guess that's it."

"Won't you need makeup, lipstick, eye liner, and eye shadow? And what about a wig?"

"A wig?"

"Surely, you can't wear a dress without wearing a wig."

He watched a big smile brighten her face.

"How'd you know the clothes were for me? Did you know all along? Am I that obvious? Do I really look like a cross-dresser?"

"Don't worry your secret is safe with me. My brother was a cross-dresser. I used to help him get dressed."

He didn't know what to say. He was speechless. He was mortified. Never had he felt as embarrassed.

"It's just there's a cross-dressers Halloween bash that I'm attending and I always wanted to know what it felt like to—"

"Topsy Turvy?"

"Yes," he looked at her in disbelief. How did she know? Maybe other cross-dresses who are attending the big bash buy their clothes here and from her.

"Yeah, my brother attended that every year. He even took me one year."

"Really? No kidding. I don't believe this. So, tell me. What's it like?"

"It was fun, low key with about one hundred cross-dressing men. Only, every year it gets bigger and more men attend. This year's event is supposed to be their biggest and best from what I've heard from some of my cross-dressing customers. I'll tell you what," she said. "Why don't you come back to my place and you can try on your purchases. I have a wig that I can loan you to wear. I can even show you how to do your makeup. And maybe after a glass of wine or two, you can convince me to model some lingerie for you."

"Sure, okay. I'd like that."

"Will your brother be there?"

"No, he was murdered."

"Murdered?"

"Yeah, a couple of guys saw him dressed as a woman and thought he was gay. They threw a brick at him and it hit him in the temple. He never knew what hit him."

"I'm sorry. I'm so sorry."

"Oh, it was years ago. I still miss dressing him, though, helping him to get ready. He was the sister that I never had," she said with a laugh. "I can help you get dressed, if you'd like. I can even shave your legs if you'd like me to or want me to do that. I used to do that for my brother. I even used to give him a bikini wax. I mean, it wasn't sexual or anything like that, although I did have to hold his cock to move it out of the way while I waxed his balls. We were more like girlfriends than we were brother and sister. He even gave me a bikini wax when I was going on vacation to Mexico and wanted to experience a nude beach."

"Yeah, that is really nice of you to volunteer to help me."

"Maybe, later, you can take some candid photos of my...works of art," she said looking down at her breasts and then looking up back at him.

"Okay, yeah, sure, and maybe later, after a glass of wine or two you'll feel comfortable enough with me to share your story about the trick your husband played on your regarding the name of your shop."

"You'll have to get me drunk to tell you that story, Bob, but we'll see."

In the next chapter Bob gets dressed.

*

Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued...



Halloween Cross-Dressing Bash Ch. 05



"Oh, it was years ago since my brother's murder. I still miss dressing him, though, helping him to get ready for the Topsy Turvy Happy Halloween Cross-Dressing Bash. That event was always the highlight of his year and that was fun for me, too. He was the sister that I never had and we were so very close," she said with a laugh. "I was thinner then and we were the same size and he was always wearing my clothes and whenever he bought a new outfit, he'd share it with me, too." She looked at him and smiled. "I can help you get dressed, if you'd like. I can even shave your legs or your back or your chest if you'd like me to or want me to do that, along with doing your hair, makeup, and painting your fingernails."

"Really? That would be so great if you could help me get dressed, help me with my makeup, loan me your wig, paint my fingernails, and shave my legs and my back in readiness for the Halloween bash."

He imagined having legs as smooth as silk. He imagined her helping him put on his pantyhose. He imagined her seeing his cock for the first time and him getting an erection with her look. He imagined himself with a huge boner sticking straight out of his pantyhose and her reaching her hand inside, taking hold of his cock and wrapping her fingers around it while trying to adjust him to make it look more presentable.

"Yeah, sure, no problem, I used to do that for my brother. I even used to give him a bikini wax," she said with her cheeks suddenly looking a bit red. "I mean, it wasn't sexual or anything like that, although I did have to hold his cock to move it out of the way while I waxed his balls, but it was no big deal."

"Really? Wow! That would be so nice of you, if you could do that for me. I don't mean holding my cock. I mean, if you could give me a bikini wax. I can hold my own cock. You don't have to hold my cock for me."

"No, really, I don't mind. I'd hold your cock for you, too," she said giving him a wink and a sexy smile.

"Okay, that would be great if you could do that, too," he said giving her a lustful look that culminated in him staring at the huge impression her tits made in her dress.

Suddenly, he had the image of Gloria holding his cock while giving him a bikini wax. He imagined her stroking his cock while he felt her big tits and fingered her big nipples. Suddenly, he had the image of Gloria holding her brother's cock while giving him a bikini wax. He imagined her stroking her brother's cock while he felt her big tits and fingered her nipples. She was driving him wild with this sudden sexual conversation.

He couldn't believe she was telling him all this without any sexual emotion. She talked about it, as if she was talking about how to make beef stew. She was making him so horny with all this incestuous, sexual talk. He was fascinated that this woman could be so candid and so erotic while seemingly acting so innocent, albeit she did get a look of embarrassment when telling him about having to hold her brother's cock.

"Okay," she said laughing, "now that I remember it, he did get an erection every time I touched him and every time I held his cock in my hand to move it out of the way. My brother had a big cock, too. He was always so horny and was always feeling my tits at every opportunity. Maybe because his wife was flat chested, but he loved my big tits. Besides, it was just horseplay and innocent teasing between brother and sister, you know. Nothing ever happened. It wasn't sexual whatsoever."

"Well, I think if my sister held my cock, I'd get an erection, too. Only, if my sister held my cock, I'd think it was sexual. If my sister held my cock, I'd want her to jerk me off or blow me. We must have had a different relationship than the one you had with your brother, I guess. Guys are all such horn balls."

Suddenly, he imagined his sister holding his cock and his sister giving him a slow hand job. Now, that he thought about it, there was that time, a few times, she walked in his room unannounced and caught him jerking off. He was always jerking off and she'd always stare at his cock before leaving the room without saying anything about it, not even apologizing for barging in on him. 

He wondered if she did on purpose. He wondered if she knew he was jerking off, heard him jerking off, and took the opportunity to barge in his room to catch him masturbating and to stare at his cock. He never considered that as a possibility, until now, and until talking to her about her brother.

He always just felt embarrassed. He always just felt perverted. He thought he was the only one who jerked off numerous times a day, every day. Back then, he never realized that all guys his age masturbated.

Bob thought of his sister growing up. Although he always wanted to, he never felt her tits. She never gave him a bikini wax or held his cock for that matter. Except for the looks he stole through the keyhole when she was changing for bed, and jerking off over what he saw later when alone in his room, that was the extent of his incestuous encounter with his sister. With all this incestuous talk, he remembered he used to do that same with his mother, too. 

He remembered he'd watch his mother through the keyhole getting undressed, only to jerk off over what he saw later in the privacy of his bedroom and in his bed. Then, he remembered all the times he tried on his mother's and sister's underwear, panty and bra, and jerked off while wearing it. He wondered if they knew. He wondered if they suspected. That was the first time he experimented with cross-dressing and now, he was about to take the biggest step when attending the Halloween Cross-Dressing Bash. Finally, he was going to see himself all dressed to kill as a woman. 

How could he possibly forget that he used to dress up in his sister's and his mother's underwear? That was so exciting to prance around while wearing their underwear. He couldn't discern if it was so exciting to wear women's panties and bras or if it was even more exciting to wear his mother's and his sister's panties and bras. He wondered if that was incestuous behavior. Probably, it was. Now, this story that Gloria was telling him in confidence had him more than excited and he hoped she'd tell him more to make him even more excited. He never considered cheating on his wife and adultery, until he met her. Now, except for the Happy Halloween Cross-Dressing Bash, she was all that he thought about.

"Well, there was that one time that I gave my brother a hand job," she laughed and turned a bit red again.

"Seriously? You gave your brother a hand job? Wow! No kidding."

"Yeah, I mean, it wasn't intentional or planned, it just happened. We were just both caught up in the moment."

"How old were you?"

"Oh, God, I don't know he was maybe 25-years-old or 26-years-old and I was in my early thirties. That seems like so long ago and it was. Wow, I can't believe it was nearly ten years ago. Where did the years go?"

"So, tell me, how did it happen?"

She was making him so hot with this incestuous talk. He couldn't believe she was like this, giving her brother a hand job. Now, he couldn't help but wonder if she flashed him her tits on purpose.

"At the time, he was going through a horrible divorce and he needed some comfort and we started innocently hugging one another. He had only been married two years. Then, he kissed me and I kissed him back. That was when he put my hand on his cock. He was on the table and I was giving him a bikini wax in readiness for the Halloween Cross-Dressing Bash. I mean, his cock was right there and it was obvious by his huge erection that he needed a sexual release," she said with her eyes starting to well up, obviously missing her dead brother.

"It's okay," he said touching her shoulder and handing her his handkerchief.

"He had a beautiful cock and I had always been curious about touching him. I used to fantasy about having sex with my brother whenever I masturbated. I was so horny back then. My husband had some sexual peccadilloes and he couldn't perform in the way that normal men did, which is part of the Glory Hole story that I might tell you if you get me drunk enough. So, I just kind of reached over and gently started stroking him," she said looking at him with a sincere smile. "It was all so very innocent. There was nothing sexual about it at all. It was just a sister comforting her brother."

"It's okay, Gloria. You don't have to finish the story, if it's too painful." He hoped she would finish the story, but he felt that he had to say that for her to finish.

"No, it's okay. I want to finish telling you about my brother. I had never told anyone this, until now. I had put it out of my mind and had forgotten most of it, until now. Telling you about the relationship we shared is cleansing."

"Then, please continue. It's probably good for you to talk about it," said Bob hoping she'd go on with her story.

She was making him so hot and horny. She made him wish his sister was like her. He wished he had a sister who gave him bikini waxes and hand jobs. It would have been erotic fun to have a sister with benefits. Then, he imagined his mother giving him bikini waxes and hand jobs. He wished both his mom and sister were more sexually open to incest in the way Gloria was with her brother. He envied their loving relationship.

"It all started when he wanted to see my tits. Well, it didn't bother me to get topless in front of my brother. He had already seen my breasts when he and his wife came with my husband and me to a nude beach last year. It was no big deal. We even fooled around in the water. He'd swim up behind me and put his big arms around me and pull me down under the water. Once submerged, he was like an octopus touching me everywhere and pulling and twisting my nipples, which I actually love by the way. I teased him, too, by groping his cock and stroking him a little under the water. We were just fooling around. It was no big deal, really and there was nothing sexual about our antics at all. We were just goofing around."

"Yeah, it was like you were kids again and playing tag in the water."

"Yes, exactly, it was as if we reverted to when we were growing up together and skinny dipping in the pond behind our house. Only, he was just horny and lonely and feeling sad, even back then because it was around the time that his wife found out about his secret and discovered that he was a cross-dresser."

"Wow that must have sucked. My wife wouldn't understand if she knew I cross-dressed. She'd want a divorce, too."

"Well, only, it was worse for my baby brother. I was seven years older than him. She thought he was gay. Of course, he wasn't. She figured he'd be sleeping with men. Of course, he didn't. It was around the time of the AIDS scare and she thought he had AIDS, no doubt. Of course, he didn't have AIDS. They were divorced soon after that. The Happy Halloween Cross-Dressing Bash was the only thing that uplifted his spirits. He made a lot of good friends there, which I'm sure you will, too."

"It's understandable that you're brother would look upon you for comfort, since you were the older sister, his big sister."

"Yeah, only, once he saw my tits, once I got topless in front of him, he wanted to feel them and once he started feeling them, holding them, touching them, and caressing them, he wanted to suck them. I admit that it was flattering to have someone, even if it was my brother, who was so enamored with my breasts. He made me feel sexy. He made me feel beautiful and desirable and it felt good to have him touch me like that."

"It's understandable you'd fall victim to that. Everyone needs to feel sexy and wanted. At the time, it sounds like you were two lonely people who happened to come together sexually, and who happened to be brother and sister."

"Yeah, well, still, at first I was a little bit uncomfortable having my brother suck on my nipples, it was more than weird. Yet, once he started sucking them and once he started fingering my nipples and pulling them and twisting them, he was making me excited. I could tell that he loved my tits. He was making me horny. I remember that I was so wet that I would have done anything," she looked at him with an excited smile. "Do you know what I mean? I would have sucked his cock if he wanted me to do that for him. He was my brother after all and we had never done anything like this before, but he was so distraught and sucking my nipples did seem to calm him, while it excited me at the same time."

"You were a good sister to have put your feeling about incest aside and give your brother what he needed." He reached down to adjust his erection and she followed his hand with her eyes. "Sorry, your story is making me a sexually excited."

"I'm sorry. I'm giving you too much personal information. Suddenly, I'm embarrassed. Sometimes, I don't realize what I say can be taken so sexually. What I think is innocent is sexual to someone else. Do you want me to stop?"

"No, please, I'd like to hear what happened."

"Well, now, that I think of it, I may have given him a blowjob, too. I don't remember. It was so long ago and I was a little bit drunk. Actually, I do remember. I was on my knees shaving my brother's thighs and he was naked. Yeah, I remember now. He started fooling around, teasing me with his cock and the more he rubbed his cock on my forehead the more of an erection he started getting. I remember his cock being so big and so hard. Except for an old boyfriend in high school and the limited sexual contact with my husband, I didn't have much sexual experience back then and it was exciting to have a cock right there, even if it was my brother's cock to experiment with."

"I envy the relationship you had with your brother. I wish I had a relationship like that with my sister. Only, she was a prude." He looked at her. She was pretty and he was sexually attracted to her, especially now that they were talking about sexual things. "I'm sorry. I've interrupted you. Please continue with your story."

"I'd reach my hand up and swipe it away and he'd pull me by my wrist and put my hand on it. Then, when he squatted down a bit and started rubbing his cock on my cheeks and on my nose while feeling my tits, he was making me so horny. Had I not been drinking, I don't think I would have sucked him off him, but I just took his cock in my hand and started stroking him before I opened my mouth and started blowing him."

"Wow, that's so hot. I can't believe you blew your brother."

"It was no big deal; we were more like girlfriends than we were brother and sister. He did cum in my mouth, though and I did swallow, but it was just a blowjob. It was much like what happened between Bill Clinton and Monica Lewinski. It wasn't like we had real sex or anything.

"Yeah, that's a good point. It was just a blowjob."

"Actually, he promised me that he would tell me when he was ready to cum, but he didn't. He promised me that he wouldn't cum in my mouth," she said laughing. "Instead, when he was ready to cum, he put his hand to the back of my head and pushed forward. He exploded his cum in my mouth. He must not have cum in a long time because there was so much of it. Then, when he pulled his prick from my mouth, he exploded more cum again giving me a cum bath. I had cum everywhere, on my tits, in my hair, up my nose, even in my ear. I mean, that wasn't the first time I had given a blowjob, this wasn't the first time that I had swallowed, and it wasn't the first time that I had a cum bath, but he was my brother."

"Damn, Gloria that was a hot story."

"He even gave me a bikini wax once when I was going on vacation to Mexico and wanted to experience a nude beach there, too."

"Really? So he saw you naked?"

"Yeah, sure, my brother saw me naked lots of times. We were always together. Shit, now that I think of it, I think we fucked when he was giving me that bikini wax. I forgot about that. Wow, I can't believe I forgot about that. We did a lot of drinking back then. We had both developed a fondness for tequila and a desire for one another. I guess now that I think of it, we were hot lovers for a brief period." She looked at him with an awkward smile that showed her obvious embarrassment. "It was just the one time, but he had made me so horny touching my pussy. Then, he started rubbing my clit and that's all it took. I remember now. I fucked my brother. I guess we did have sex. Surely, you had sex with your sister at least once growing up. Right? Surely, your sister gave you a hand job or a blowjob."

"Sex with my sister? No, I never had sex with my sister."

"Oh, well, I hope you don't think less of me because I had sex, I mean, comforted my brother during his troubled times."

"No, not at all, I'm just as excited with this incestuous story as I am that you've volunteered to help me get ready for the Halloween Cross-Dressing Bash. Yeah, that is really nice of you to volunteer to help me. I can't tell you what a load of my mind having someone to help me with my hair and makeup."

"Really, it's my pleasure. Maybe, later, you can take some candid photos of my...works of art," she said looking down at her breasts and then looking up back at him.

"Really? Are you serious?"

"Yeah, sure, why not?"

"Okay, yeah, sure, and maybe later, after a glass of wine or two you'll feel comfortable enough with me to share your story about the trick your husband played on your regarding the name of your shop."

"You'll have to get me drunk to tell you that story, Bob, because if you think what I told you about my brother is hot, you'll be out of your mind with passion for me when if I tell you the story of how my ex-husband tricked me, but we'll see."

In the next chapter Glory helps Bob get dressed and then tells him about the Glory Hole story.

*

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To be continued... 



Halloween Cross-Dressing Bash Ch. 06



Gloria left the store in the capable hands of her store manager, Sharon. After paying for his purchases, with Gloria giving Bob a very generous and unexpected 20% discount, Bob followed her car home in his pickup truck. He was just as excited to maybe have a sexual affair with her as he was with the thoughts of trying on the clothes he just bought.

They stopped at a nice house set back away from the others at the end of a long, winding tree lined cul-de-sac. The trees afforded the property plenty of privacy and it couldn't be seen from the road. When driving up to it, Bob was more than a bit nervous. What if this woman had something against cross-dressers? What if she tied them up, tortured them, and had her way with them before murdering them? What if she was the one who threw the rock at her brother and murdered him? What if that wasn't her brother at all, but just some customer she invited home in the way that she invited him? What if her Glory Hole story wasn't a sexual story at all, but how she murdered her victims.

He had never been with another woman other than his wife. Yeah, sure, he'd looked at plenty of women, but he never touched another woman since he's been married. He's been a faithful husband. Only, he and his wife hadn't had sex in nearly three years. He was more than horny. Besides, he wasn't as interested in being with women, other than his wife, as he was with dressing as one. Cross-dressing and masturbating took the edge off not having sex with a woman. Still, nervous after allowing his imagination to run wild, he calmed down when she opened her front door and invited him inside.

"Come inside, Bob, and make yourself comfortable. What will you have to drink?"

"I'll have a beer if you have one."

"One cold beer coming right up."

She handed him a cold Bud and a glass.

"That's okay," he said waving off the glass. "I drink it out of the bottle." 

He was a real man, a man who drank his beer out of the bottle, albeit a man how enjoyed wearing women's clothes. Besides, drinking from the bottle added to the pleasurable experience of drinking beer and the only better ways to drink a beer was to belly up to the bar for the bartender to pour a cold, frosty one right from the tap. 

She sat across from him drinking some girly type of drink, no doubt. She was a lady, after all. He couldn't believe he was here sitting across from her. He couldn't believe how pretty she was. Sure, she was a full figure woman and much larger than his wife, but he enjoyed her for who she was inside. She was very personable and he liked that about her. She made him feel comfortable and it was obvious that she liked him for who he was. It didn't matter that he was a cross-dresser. To her, cross-dressing wasn't an end all issue, as it would be for his wife, if only his wife knew that he loved to dress as a woman.

"I needed a drink after being on my feet all day and this taste so good," she said holding the cool glass to her cheek and closing her eyes for a second.

"What are you drinking?"

"A double scotch with a splash of water."

Wow, he thought she was drinking a girlie drink to find out that she was drinking a real drink, the hard stuff, and she was drinking it like a man without watering it down with ice. He liked this woman. No doubt, after drinking two of those double scotches, her lips, all four of them would not only be loose enough to have sex with him but also to tell him the story about how her husband took advantage of her. He couldn't wait to hear that story. He wondered what it was. He could only imagine. Surely, it had to be something really despicable and maybe even perverted. 

"This is a nice place," Bob said looking around the ranch style home. "You have a very beautiful home. You live here alone?"

"Yeah, I never had kids. My husband never wanted them. He was tight with a dollar and kids cost money. I was pregnant once, but had a miscarriage. It was just as well because, as it turned out, he was more than a bit weird."

Bob thought she would get into the story from that statement, but when she didn't he said nothing to encourage her to say more. He didn't want to ruin any opportunity he may have with her by pressuring to talk about something that she wasn't yet ready to share with a stranger and with him. Only, he hoped for the opportunity to bring it up again in conversation.

He took a sip of his beer before peering in the bag of clothes he bought from her little dress shop, the Glory Hole. He loved touching the undergarments he bought. They felt so soft and so silky. He couldn't wait to feel them against his skin. He felt the bra and fingered the panty before pulling out the dress to look at it, again.

"I really like this dress," he said. "As soon as I saw it, I fell in love with it as soon as I saw it. I think my mother had a similar dress so long ago," he said with a satisfied smile. "It's the gold buttons that make the dress, I think. It looks a little like a uniform, only more dressy. Do you know what I mean?"

"Yeah, I know exactly what you mean, Bob. Moreover, your mother may have had a similar dress. A dress like that never goes out of style." She gave him a smile. "I can tell you're excited about your purchases and can't wait to try them on. I'm so happy to have helped you find what you wanted. I'm so happy to have met you and made a friend."

"Me, too," he said giving her a warm smile. "Yeah, I am excited about trying on my purchases," he said looking at the inside tag before holding the dress up with outstretched arms. I just hope it fits."

"Well, go ahead and try on the dress. If it's too big or two small, we have the same dress and in the same color in other sizes. I'm curious, too. I'd like to see how it fits you, too. I'm dying to see you wearing it."

"He looked around the room. Where can I try the dress?"

"Try it here, please, Bob," she said taking another sip of her drink before leering at him, "so that I can see how it fits as you are putting it on over your head."

"Really? You don't mind? You want me to get dress in front of you?"

"Well, after you ogled my tits, it's only fair play that I ogle the bulge in your underwear, don't you think?"

"Okay, yeah, sure," he said laughing and standing to unbutton her shirt. He removed his shirt and t-shirt displaying his hairy chest, back, and shoulders and his bulging beer belly.

Before he removed his shirt, she started humming strip tease music while he unbuttoned his shirt and Bob got into the game by slowly stripping and teasing her with his chubby body. Once he removed his shirt, he unbuckled and unzipped his jeans. Intently, she watched him while focusing her concentration on the big bulge that suddenly ballooned out his briefs. He was so horny and so hot for her that he already had a fairly large erection.

"It looks like you have a big cock, Bob."

"Thank you, I do," he said looking down at it while rubbing his beer belly. "And with his big gut, it's a good thing that I do," he said with a laugh.

She sat on the sofa with her legs slightly spread and enough apart for Bob to see her panty from where he stood across from her while stripping off his clothes. He wondered if she knew she was showing. He wondered if she was flashing him by accident or on purpose. Truly, it didn't matter which it was, by accident or on purpose, so long as she continued flashing him. Up skirts and down blouses were his favorite views. Definitely, she was giving him a nice up skirt of her white panty. The sight of her panty added to his erection. He imagined walking over to her and her taking his cock in her hand before blowing him.

He wiggled into the dress and walked back and forth in front of her with the dress on. It was obvious that he needed a makeover. His legs from his ankles to his crotch were hairy. He had hair from his fingers to his shoulders with plenty of hair on his back, as well as his chest. She'd be waxing and shaving him for a while.

"Oh, well, I hope you don't think less of me because I had sex, I mean, comforted my brother during his troubled times while he was going through his divorce," she said after downing the rest of her drink while hinting at a replay of the conversation that had in the store before they arrived at her house. Obviously, for her to start this sexual conversation, again, the alcohol was already working its magic on her inhibitions. 

"Let me fix you another scotch," he said.

"Thanks, Bob," she said handing him her glass. This time he poured her a triple with even less of a splash of water. He was hoping to get her high enough that she would enlighten him with her Glory Hole story. Surely, he had heard plenty of glory hole stories, only, he couldn't imagine that her story would be anything like those that he heard or imagined. 

"Why would I think any less of you? I don't think any less of you just because you showed your brother some sisterly comfort and love. He needed you at that moment and you helped him though a bad time. I'm just as sexually excited by this incestuous story as I am that you've volunteered to help me get ready for the Halloween Cross-Dressing Bash." 

"Really, you find my incestuous story of what happened between my brother and I sexually exciting?"

"Oh, yeah, that's every guy's fantasy to do his older sister."

"I'm sure that it is," she said with a laugh after taking another long sip of her drink.

"I can't tell you how much I appreciate your help in helping me select my outfit and in helping me do my hair, makeup, and fingernails. Thank you so much. That is really nice of you to volunteer to help me. I can't tell you what a load off my mind having someone to help me with my hair and makeup and even to do my fingernails. I don't have the patience to do my nails. My hands start shaking and I get nail polish all over my fingers."

"Well, it's my pleasure to help you get ready for the Happy Halloween Cross-Dressing Bash." She looked at him and smiled. "Do you know why they call it Happy Halloween Cross-Dressing Bash instead of Halloween Cross-Dressing Bash?"

"No, actually, I never gave that a thought, but now that you mention it, I am a bit more than curious. Why do they call it Happy Halloween Cross-Dressing Bash instead of just Halloween Cross-Dressing Bash?"

"Well, this is my brother's reasoning and not mine and probably not the officially answer, at least, I don't think that it is. I don't have a clue why they named it so, but he said they put the Happy first because they wanted everyone to have a happy time. He said that too many times, too many cross-dressers are torn and tortured and that this bash, one of several that they hold throughout the year, allows men who are so inclined to feel the need to dress as a woman to be happy while dressed as a woman instead of feeling sad before they feel that they must dress, uncomfortable during the time that they are dressed, and guilty after they have dressed in women's clothes. This happy time removes all of those internal struggles that they have wrestled with all of their lives. This bash really is a place for them to have a happy time. It is their safe haven of acceptance away from the cruel world of ridicule."

"Well, that explanation makes sense to me. It would take a cross-dresser to come up with that as an explanation." He smiled at her. "I can't wait," said Bob. "I'm so excited." He looked at her. "Do you think I should shave my mustache?"

"Yes, of course, Bob. How many woman have you ever seen with a bushy mustache like you have?"

"None, but I've had this mustache for nearly thirty years. I don't even remember what I look like without it."

"Well, there are men who go to the bash with mustaches and full beards, even. The choice is up to you. If you feel the need to look, walk, act, and talk like a woman; then you should shave your mustache. Yet, if you feel that it's enough of a thrill just to wear woman's clothes, then I'd keep the mustache."

"Yeah, I think I'll keep it. I'm not trying to fool anyone. With my body, the way that I walk, and how I carry myself, there's no mistaking me for a woman. I look like a guy. Besides, my wife would know something was up if she saw me without my mustache. She'd give me the third degree as soon as I walked in the door asking me if I shaved my mustache because my new girlfriend doesn't like mustaches."

Gloria took a couple of quick sips of her drink.

"Don't look so sad, Bob. You'll have a good time," she said with a smile. "Maybe, later, after I've finished this drink and had another, you can take some candid photos of my...works of art," she said looking down at her breasts and then looking up back at him.

"Really? Are you serious?" He stared at the huge impression her tits made in her dress. "You have beautiful breasts."

"Thank you, Bob. Yeah, sure, why not? What the Hell, you've already seen the twin girls anyway; why not photograph them, too," she said with a laugh.

"Okay, yeah, sure, and maybe later, after a glass of wine or two you'll feel comfortable enough with me to share your story about the trick your husband played on your regarding the name of your shop."

"You'll have to get me drunk to tell you that story, Bob, because if you think what I told you about my brother is hot, you'll be out of your mind with passion and desire for me when if I tell you the story of how my ex-husband tricked me, but we'll see. I'd have to feel a bit more comfortable with you to share that story with you."

"Excuse me while I change into something more comfortable. I've been in this dress all day." She stood and when she did, she flashed him her panties again when getting up from the low sofa. "Would you mind doing me," she said again, this time turning her back to him and pointing to her zipper.

"I'd love to do you, Gloria. You are a very pretty and sexy woman."

"Well, thank you, Bob. Maybe if you get me drunk enough, you can take advantage of me," she said with a sexy laugh. "Only, for now, I meant, would you unzip my dress."

"Yeah, sure."

He slowly unzipped her dress all the way down to the top of her hips.

"Thank you that feels better already." 

"Would you like for me to undo your bra?" 

"Sure, if you can, it's very tight. Undoing my bra would be a great relief."

Bob pulled the elastic material forward and struggled with the hooks, but he undid the four of them. It was a very wide bra. The back of his wife's bra was very narrow and only had one hook. He had never seen a bra with four hooks before. As soon as he undid her bra, he reached his hand inside her dress and around the front of her and felt her big tit through her bra. It was enormous. Never had he felt a tit as big. Then, he lifted her bra cup and her breast fell to meet his hand. He felt the weight of her big tit and briefly fingered her nipple before she pulled away from his hold.

"Bob, you're so fresh," she said turning to face him. He kissed her and she kissed him back, but when he tried to part her lips with his tongue, she pulled back. 

"Let me get into something more comfortable, Bob."

"Sure," he said allowing her to leave.

He watched where she went hoping she'd go in the bedroom across the way and leave open the door, as she had left the curtain open in the dressing room when she accidentally on purpose showed him her big boobs while she was changing her clothes to model his dress on her. He was hoping she'd give him another show of her big boobs, accidentally, of course, on purpose. Only, she went to the bathroom around the corner and closed the door.

After what seemed an hour but was only twenty minutes, she emerged wearing a low cut black negligee with matching bathrobe. The material was so sheer that even wearing the bathrobe, he could clearly see through both. He saw the outline of her pussy and could see that her pubic hair was trimmed. More importantly for him, being the breast man that he was and being in the constant horny and terribly aroused state that he was, he could see her areolas and nipples. Her areolas were the size of small saucers and her nipples were as big as hard candies and already were erect. He couldn't wait to feel her breasts. He couldn't wait to suck her nipples. He couldn't wait to see her tits, again.

She pulled out a folding table, he imagined like the one she used to give her brother a bikini wax. His mind was filled with her standing over her brother topless while he felt her big tits and while she slowly stroked his cock before leaning down and taking it in her mouth. He imagined the incestuous sight of her blowing her brother. 

"Well, Bob. Are you ready?"

"Ready for what?"

"Are you ready to remove your modesty, get naked, and climb up on the table so that I can free you from all that body hair?"

"I'm ready to get naked, but I don't know about the bikini wax, Gloria. I think it would really hurt."

"Well, I have an electric shaver I could use on you, if you prefer."

"Oh, that would be better."

"Which first? Front or back?"

"Let's do the back first."

Bob was quick to change out of the dress and remove his briefs. His cock was semi-erect but grew harder as soon as he saw her staring at it.

As soon as he climbed on the table and got comfortable face down, she giggled and gave his fat ass a slap. He could feel the tickle of the shaver across his shoulder, back, ass, and thighs. Even though it tickled it felt erotic to have a strange woman shave his naked body. Within ten minutes he was ready to turn over. When he did, his cock was pointing straight out.

"Well, Bob, at least with that big boner, I don't have to hold it out of the way," she said laughing.

"Sorry, but the sight of you in that sheer, black negligee is enough for any man to get excited. It makes you look so sexy."

"So, you like my negligee, huh?"

"Oh, yeah, only I like what's underneath it more," he said reaching his hand up to feel her tit and fingering her nipples before pulling and twisting them. He remembered she said that she liked it when her brother pulled and twisted her nipples. He remembered her saying that her nipples were sensitive to that kind of play. 

"Oh, Bob, that feels good when you touch my nipple. My nipples are very sensitive, but now is not the time. I need to concentrate so that the shaver doesn't slip and we really make you into a woman."

She shaved his shoulders, chest, stomach, and legs. Then, she took her time shaving his balls and cock spending quality time holding his stiff prick in her hand.

"I love the feel of your hand around my cock."

"Do you like it when I do this, Bob," she said slowly stroking him while staring down at his big prick.

"Yes," he said while reaching up his hand to feel her massive breasts again.

"What if I did this," she said leaning down to take his cock in her mouth for a few seconds while sucking it and twirling her tongue around it. "Did you like that, Bob," she said removing his cock from her mouth to talk.

"Oh, God, yes. That was incredible. It's been a while since I've had a blowjob."

"It's been a while since I've given a blowjob.

Suddenly, she looked sad.

"What's wrong?"

"I haven't been able to orally pleasure a man, since what my ex-husband, the no good, dirty bastard did to me."

"Tell me what happened. What did he do?" 

In the next chapter Gloria tells Bob the Glory Hole story.

*

Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued...



Halloween Cross-Dressing Bash Ch. 07



"So, you like my negligee, huh?"

"Oh, yeah, only I like what's underneath it more," he said reaching his hand up to feel her tit and fingering her nipple before pulling and twisting them through the thin, black sheer material of her negligee. He remembered she said that she liked it when her brother pulled and twisted her nipples. He remembered her saying that her nipples were sensitive to that kind of play. Pulling and twisting her nipples was okay by him, as he had a penchant for tits and nipples. 

"Oh, Bob, that feels good when you touch my nipple like that. It sends shivers down my spine and brings back memories when my brother was lying on this table naked while I gave him a bikini wax and he touched me where no brother should touch his sister." She looked down watching his fingers work their magic on her nipples. "Although I am very much enjoying this, now is not the time to get me all hot and bothered. I need to concentrate so that the shaver doesn't slip and we really make you into a woman, instead of a man who enjoys wearing women's clothes," she said with a laugh.

She shaved his shoulders. She shaved his chest. She shaved his stomach. She shaved his legs. When she was done shaving his hairy body, she had enough of his body hair to make another Bob. Then, she took her time shaving his balls and cock spending quality time holding his stiff prick and cupping his balls in her hand while shaving them silky smooth and soft.

"I love the feel of your hand around my cock."

"Do you like it when I do this to your cock, Bob," she said slowly stroking him while staring down at his big prick and teasing him.

"Yes," he said while reaching up his hand to feel her massive breasts again and fingering her nipple through her sexy negligee before teasing it out and more erect with a twist and giving it a playful pull.

"What if I did this to your cock," she said leaning down to take his cock in her mouth for a few seconds while sucking it and twirling her tongue around it before deep throating it. "Did you like that, Bob? Did you like it when I took your cock, all of your cock in my mouth and ran my tongue around it," she said removing his cock from her mouth to talk.

"Oh, God, yes. That was incredible. It's been a while since my cock has been in any woman's mouth other than my wife and it's been a very long time since I've had a blowjob."

"Well, it's been a very long time since I've given a blowjob.

Suddenly, she looked sad.

"What's wrong?"

"I haven't been able to orally pleasure a man, since what my ex-husband, the no good, dirty bastard did to me."

"Tell me what happened. What did the son of a bitch do?" 

She looked at him with a face full of hurt. Her eyes welled up and she looked old and tired suddenly. The transformation that came over her was immediate. She gave him a look that was forlorn and dark.

"Come with me," she said.

"Wait, should I put something on?"

"No, I'd prefer if you came as you are. It's better if you are naked."

"Okay."

Suddenly, he was afraid. Suddenly, he imagined she was leading him to be slaughtered. He imagined her taking him to the dungeon where she chained him to a concrete wall and where he saw the skeleton of others who were chained there before him and left to die. He wondered if they were alone in the house. Maybe, she was taking him to be murdered. He had an uneasy feeling, especially as she herded him downstairs.

She walked ahead of him leading the way to a basement that was another living space to the house. With thick wall to wall carpeting, recessed lighting, a pinball machine, a pool table, a gaming table, a full bar, and a complete media room resplendent with a huge plasma television, the place was what every man would love to have. He had no idea such a modest home housed such an elaborate setup as was this. This was his dream getaway. Never had he seen such an elaborate setup. This must have cost her a fortune.

"This was my ex-husband's pride and joy," she said with a bitter smile. "He was always down here playing poker, watching football games, and entertaining his friends while getting drunk. He had a lot of friends and every weekend our house never had less than a dozen men congregated down here enjoying this living space while watching movies and football games on the plasma television." She looked at him with a sullen face. "There was a lot of drinking down here and when men drink, they get horny and wild for sexual activity."

"Wow, this place is huge. It's great. It looks bigger than all of upstairs. I wish I had a space like this with a huge television like that and that bar with the huge mirror over it is phenomenal. I don't even have a poker table, never mind a pool table."

"He took over part of the garage that runs under the house. He built a separate unattached garage for the cars out back. I hate coming down here, though. I never come down here. It gives me the creeps to come down here alone. I feel as if this place is haunted with his evil spirit and with all the evil spirits of all his asshole friends."

"I wish I had this in my house. Only, he must have spent an absolute fortune to turn this basement into such a spectacular men's space. I mean, just one of those overstuffed media chairs must have set him back plenty and he has how many of them, one three, five...eight. It must have felt you were in a real movie theatre while watching a movie."

She led him to a door in the corner of the room and on the same wall where the bar was. She stood in front of it before opening it. Looking as if she was frightened and fearing what was behind the door, she looked as if she was afraid to open it, but she did with hesitation and great trepidation. With a resigned determination and resolute strength, she flung open the door, as if the feat was no small victory.

"This room is why I haven't given anyone a blowjob since I've ridden myself of my evil ex-husband from my house and from my life. I'm glad he and his friends are gone, but what he did to me has scarred me for life."

She turned on the light. It was another good sized room that further tricked the mind that this space was so much bigger than the space upstairs. There was a window that ran nearly the width of the wall. A couple of chairs with a sofa that was set back from the windowed wall had three tables with ashtrays and scatterings of coasters should someone want to put their drink upon the table while watching and looking out the window. An aroma therapy machine was mounted to the wall that gave a measured and timed spray of floral scent. It looked like a secret room, but what was it for?

"What's this room?" He looked out the window. "Wait, this is the big mirror that's over the bar," he said turning to look at her. "Right?" He looked at her and she was crying. "Why are you crying? What's wrong? Did I say something wrong? What did I say? Did I hurt your feelings? If I did, I'm sorry."

She walked him over to the other side of the room to a wall that had dozens of holes in it that were spread throughout the wall at differing heights. It was an interior wall making him wonder what was behind the wall that housed the holes. The smaller holes were always set in the middle and lower than the larger holes. It was an odd spattering of holes, almost giving the appearance of a modern work of art, had you not known they were holes but decorations painted on the wall instead of carved through. 

"No, it's not you, she said wiping the tears from her eyes and blowing her nose on a tissue that she kept balled up in the pocket of her bathrobe. My husband devised this. This was his creation. This was the physical view into his sick mind. This was his chamber of sexual perversion," she said moving him along a long corridor that ran the length of the wall and that was perpendicular to the bar on the other side of the wall behind the room that they were just inside before they opened this door next to the bar.

Well, if her sheer outfit didn't get his attention and his libido racing, then this chamber of sexual perversion did. He couldn't imagine the story behind this room. He could only imagine the need for such a wall.

She stopped along a wall that had a series of holes. 

"What is it? And why are there all these holes in the wall?"

"He told me he couldn't get off anymore. He told me that he needed something more. He told me that he needed a fantasy and needed me to play a submissive role. As a good wife, I was responsive to his every desire and wanton sexual wish. It was my duty married to the man that I loved. 

He told me that he needed to pretend that he was someone else and that I was blowing someone else. After growing up living with my brother, a cross-dresser, I didn't think anything of it. I mean, I just thought that all guys had sexual fetishes and erotic peccadilloes to get their rocks off," she looked at him and gave him a half smile. "I trusted him. Only, he took advantage of my naiveté."

"Gloria, what is this? I still don't get what I'm looking at and why you are so upset? What is this room and why is there a two way mirror?"

"Go through that door," she said pointing to the far end and come back around to where you see the holes. Then, walk forward and put your cock through the smaller one and your arms through the larger holes."

It was designed like an adult fun house with mirrors and cameras to record the action from every angle. He did as she said and Gloria got down on her knees and accepted his cock in her mouth. He reached down with his arms through the bigger holes and fondled her big tits.

"Oh, I see. This is what your husband created? Wow, he was a very ingenious fellow. So, he needed you to think that he was just some stranger sticking his cock through the hole. Well, really, I don't see anything wrong with that. I mean, whatever floats your boat and if he needed to pretend you were blowing someone else to cum, then what's the harm." He laughed. "I wish my wife would play a game like this with me. Maybe, we wouldn't have the problems we have now. Maybe, we'd be having more sex. Maybe, I wouldn't feel the need to cross-dress and wear women's clothes if she gave me what I needed. I don't know. Who knows what goes on in someone's mind when it comes to sex?"

"Come back around now, please. I don't like staying down here for very long. It just gives me the creeps."

"Wow that was great. The holes are the perfect height. I like this place. I really like this place. I could live down here," he said looking back behind him before she turned off the light. "You must have had an awesome time playing that blowjob game with your ex-husband."

"At first it was fun to come down here and to have a sexual adventure with my husband, but then he wanted me to blow him every night. I was resistant, of course. I was tired from working all day as a salesclerk in a dress shop and I needed some down time. Only, he wanted me and expected me to come home from my job and from work to blow him. I told him no and wrestled with the guilt of disobeying my husband. Then, he told me that if I blew him every day for one year that he'd set me up in my own dress shop."

"So, I get it. That's how you got your store and the idea for the name. Wow, that's a great story, Gloria."

"That's only part of the story," she said giving him a wry smile. "Let's go back upstairs. I'm more comfortable upstairs and we can talk there."

She was so solemn in her tone and Bob knew there was something still wrong. He tried to lighten her mood. He figured maybe she just missed her ex-husband and missed playing those glory hole games with him.

Once back upstairs, feeling a bit chilled, Bob put his briefs back on and sat on the couch with her.

"So, tell me, why are you so upset? I don't understand."

"Well, my ex-husband told me that he couldn't get off unless I blew him when he stuck his cock through the wall. He called the wall his Glory Hole, since I was Gloria, nicknamed Glory, since I was a kid, and which later became the name of my store. He used me and that wall of holes, as a way for him to get what he wanted, namely blowjobs from me. Sure he kept his promise by setting me up in business, once I reached my year of giving him a blowjob every day for 365 consecutive days."

"Gloria, I'm sorry, but I still don't understand why you are so upset. I mean, you did agree to give him daily blowjobs for a year and he was your loving husband, after all. It wasn't like you were blowing everyone when you were kneeling down there with your tits though the holes and his hands all over your—" He looked at her and she was crying again. "Oh, you mean, he had you blow someone else?"

"Yes."

"Oh, my God. That vile cad. He had you blow one of his friends?"

"No," she looked at him with pleading eyes that asked him to guess the truth so that she didn't have to utter it.

"He had you blow some his friends?"

"No," she said again while looking at him with pleading eyes. He felt as if he was playing an X-rated game of charades. Only, he felt as if she needed to play this game to let go of her past. He was astonished and excited by her answer to his next question.

"He had you blow all of his friends?"

"Yes."

"Oh, my God, Gloria, I'm so sorry. He was no loving husband. He was a disturbed man who took advantage of his loving wife."

"That's not all," she said putting her head down and looking ashamed to tell him any more. "There was more, so much more."

"More? How much more could there be? Tell me, what is it Gloria?"

She looked at him again with those pleading eyes again. He thought of her incestuous affair with her brother and wondered if her husband had a brother. Maybe, he thought, she had confessed the story about having sex with her brother and somehow instead of understanding that as an unselfish act between brother and sister, her ex-husband had mistaken for good deed as sexual love instead of comforting love, he flipped out and wanted to make her his cum slut.

"Tell me that he didn't have a brother?"

"He did."

"Oh, my God. How many?"

"Four," she said holding up four fingers.

"He had you blow all four of his brothers."

"Yes, and his Dad and his grandfather, too."

"Oh, Gloria, I'm so sorry," he said holding her. "That bastard." 

Although he couldn't believe her story, although he had a hatred for her ex-husband, a man he had never met, his cock was throbbing with desire for her. How exciting it would be to have sex with such a woman who had given so many blowjobs to so many men. He couldn't imagine the pillow talk when thinking about her sucking off all her ex-husband's friends, his four brothers, her father, and the father of her father-in-law.

Wow! This guy was his hero, I mean, you know what I mean. Bob was just a guy; a guy who enjoyed wearing women's clothes, but this having your own glory hole wall and sharing your wife with every Tom, Dick, and Harry was every guy's fantasy. Okay, not every guy, but every sexually deranged guy.

"I feel so used and abused."

"There, there Gloria," he said patting her back while wondering if she wore kneepads. "Put that bastard out of your mind." He couldn't imagine the blowjob she could give him. Never had he known a woman so experienced in sucking cock. "Not all men are as sexually perverted and depraved as he was." Only, he couldn't think of any who were not, not even him judging by the stiffness of his cock and the erotic internal dialogue he was having right now.

That lucky bastard to devise something like this, he should pattern the design and sell it as a modular room to add on to any house or garage. What a great idea? He imagined trying it with his wife and his friends. Honey, can you come down here for a minute. I have something to show you. Oh, and come down naked, please. Okay, guys get the video camera and everyone hide. Someone turn off the lights.

"Yes, I didn't know," she said holding back her tears. "I don't know how many men I sucked off. I have no idea. Surely, it was hundreds. It may have been thousands. Only, now that I think back on it, it was a lot. I thought I was sucking off my husband, but I was sucking off the whole town. I may have given a blowjob to every man I know. While every man I thought was my friend, family member or just a passing acquaintance, they have spent quality time feeling my breasts and fingering, twisting, and pulling my nipples while I sucked their cock and they shot their cum in my mouth."

"I don't understand, though, how could you not know that you were sucking off different guys? I mean, some men have longer, shorter, fatter, and thinner cocks and some are circumcised while others are uncircumcised. And wouldn't you get a bit suspicious when your husband came off multiple times an evening."

"Lots of alcohol and sensory depravation was the reason I was unable to discern one prick from another. Also, if you are living your fantasy, as my husband told me he was, it is not unusual for a man to cum three or four times over a few hours."

"Sensory depravation? What's that?"

"It's when your senses are blocked and you can't see or hear of feel or smell. One cock feels, smells, and tastes like another and he got me plenty drunk first. Giving all those blowjobs explains why my jaw always hurt the next morning."

"He always kept the room sprayed with a floral scent and it was very dark down here, pitch black really. He played loud music in the background so that I couldn't hear anything but the music and he tied my hands behind my back and blindfolded me, so that my eyes wouldn't have a chance to get used to the dark."

"Wow, he thought of everything." 

This guy was unbelievable. Who would have thought this was possible? How could he do this to his own wife? How could he share her mouth and her tits with all of his friends, relatives, and practically every man in their little community?

"He did think of everything alright. He even thought to charge his friends for the opportunity to receive a blowjob from me while they fondled my tits and fingered my nipples. And judging by all that stuff downstairs, he must have made an absolute fortune selling my mouth and the use of my tits to his friends."

"So, how did you finally find discover his game of lewd debauchery and forced prostitution?"

"Stupidly, probably when he was drunk after the sex show that I gave everyone, he left a CD in the video recorder. When I turned the television on to watch a movie while he was at work and I was home sick, there I was servicing the neighborhood. I couldn't believe it when I saw myself blindfolded, handcuffed, and on my knees at the wall of holes. I was sick over it." She laughed a sick laugh. "He even fashioned a padded board that I could recline against to remove the pressure from my knees and that allowed me to stay at the wall longer."

"I'm so sorry, Gloria," he said giving her a hug. 

"I saw some of the men that I had blown. There they all were laughing it up and drinking. I saw my mailman, my neighbors, husbands of my friends, my gas station man, my plumber, electrician, my teller from the bank, and the grocer where I do all my shopping. One time or another, I literally sucked off every man in my small community. Of course it was only one every night, but every night I was giving my ex-husband a blowjob, only I was sucking off all his friends for money."

"This is an incredible story. No wonder why you threw him out and divorced him."

"Yet, that's okay because payback is a bitch. He left all the tapes here when I locked him out of my house and I copied them. I used the copy to extort money from all those who had me blow them. I charged $1,000 to my mailman, gas station man, banker, grocer, relatives, friends, and whoever I could identify. I made $250,000 and could have made more, if I was able to make out their faces in the videotape, but it was always so dark down there."




Halloween Cross-Dressing Bash Ch. 07



"Well, that's good that you made some money out of such a horrible experiecence."

She looked down and saw that he had an erection. 

"All you guys are the same," she said shooting him a cold stare. "Here I am pouring out my heart to you and you have an erection from hearing about me blowing the every man in the neighborhood."

"I'm sorry, but it is a hot story, Gloria, you must admit."

She put her hand on his cock and felt him through his underwear. 

"So, hearing about me sucking off men turns you on?"

"Yes, oh, God yes, only if you were my wife, I might imagine such a scenario, but I would never mistreat you in the way that he disrespected you."

"Would you like me to suck you off, too?"

"Are you serious? Oh, God, yes."

"Only, I don't know if I can. I'll try, though."

"Try, yes, please try."

She fell between his knees, pulled down and off his briefs, and took his stiff prick in her hand. Slowly she stroked his cock while staring at it before taking it in her mouth, engulfing it with her lips, and sucking it while twirling her experienced tongue around it.

"You have a big prick, Bob. It's much bigger than my ex-husband's cock. I like sucking your cock better than all of those other men I sucked."

He shot a load of cum in her mouth within three minutes. Never had he cum off so fast from a blowjob before. He calculated if she was this good to get him off within three minutes. She may have blown dozens of men in an hour and fifty men within one evening. He extrapolated his imagined totals for the year. She may have given more than 18,000 blowjobs.

In the next chapter Bob attends the Happy Halloween Cross-Dressing Bash.

*

Thank you for reading my story. I sincerely hope you enjoyed it. Please take a moment to vote, make a public comment, and/or give me feedback. Your support is why I write. Your feedback will motivate me to write a better story the next time.

If you haven't already, please take moment to add me and/or this story or any other of my stories to your list of favorites. Thanks, Freddie, Bostonfictionwriter.

To be continued...



Halloween Cross-Dressing Bash Ch. 08



She looked down and saw that he had an erection. 

"All you guys are the same," she said shooting him a cold stare. "Here I am pouring out my heart to you about what my ex-husband did to me and you have an erection."

"Sorry."

"Do you realize how humiliated I am to find out that I blew every man in my community? Then, to find out that I blew my husband's four brothers, his father, and his grandfather, now I understand why they all stare at me and giggle like little girls at every family gathering."

"Sorry. I'm ashamed of myself, but it's a guy thing. I can't help it. All guys are insensitive pigs. All guys think with their peckers. All guys get off when imagining their wives or girlfriend or significant other doing another guy."

"I'm just curious," she said giving him another icy look, "which part excites you more? Is it me naked, blindfolded, handcuffed, and on my knees or is it me blowing my four brothers, my father-in-law, and his father? Or is it me sucking off all my husband's friends? Or did you like the part about me blowing the mailman, the gas station attendant, the grocer, and God only knows who else? Or did you like the part that my husband lied to me that I was blowing him and videotaped me blowing everyone else?"

She didn't realize it, but she was making him hotter with all that dirty talk about her giving blowjobs. She didn't realize that all of it made him hot and horny.

"I'm sorry, but I can't control my erection. It's a hot story and the fact that it is you that I imagine giving all those blowjobs to all those men and not some stranger that I don't even know makes it so much hotter."

"Really," she said cooing while snuggling up to him. Fearing that she was about to bounce him out the door, finally, he said something right to soothe her. "You like to think of me being wicked and erotically adventurous with other men?"

"Yeah, I do."

"Well, my ex-husband was the same way," she said with a wry chuckle. "The difference between you getting off on me giving blowjobs to other men and him wanting me to suck off every man we knew is that he wasn't honest about it with me. At least you're a man and you're upfront with your feelings. He, on the other hand, tricked me and used me. His deception by not being honest showed me that he didn't love me."

"Yes, I'm sorry to say that I agree with you. He couldn't love you and do all those despicable things to you, which is why you two are no longer together. It was obvious to use you for his sexual benefit and monetary gain that he had no respect for you."

"Well, maybe, if he had been upfront about what he wanted, we may have come to some open arrangement that we both could have enjoyed. Although I am a bit naïve and too trusting, I'm certainly not a prude. Maybe, I could have sucked off one of his brothers instead of all of his brothers and/or maybe I could have sucked off some of his friends instead of all of his friends. Maybe, I could have blown the banker or the grocer or the mechanic, but certainly not everyone. He had no compassion for me or respect for my reputation. He's gone now, that bastard, but I still must live here." 

"Surely, you must have gotten something out of sucking cock otherwise you wouldn't have agreed to giving your ex-husband a blowjob every day for a year. I can't imagine eating my wife's pussy every day for a year. I mean you must enjoy sucking cock to agree to a daily regimen of blowjobs."

"Yeah, well, there were some days that I was really into sucking cock and whosever cock I sucked that day was the lucky one and really got off. Then there were days that I thought I'd vomit if I sucked another cock," she said with a laugh. "I feel sorry for the bastard that I blew that day because I think I put more teeth into it because my jaw was getting numb. Only," she said looking at him with an expression of appeal, "I thought I was sucking off my husband. I was so trusting and so naïve."

"Well, you are naïve. I couldn't believe you changed out of your dress and removed your bra without realizing I was in the dressing room watching you." 

"Well, maybe had I not given you a free show you wouldn't be sitting here now?" She shuddered while making a gross face. "When I think about it, I can't believe how much and whose cum I swallowed. Eww! Sometimes, I pulled out prematurely only to receive a cum bath. My face, hair, and tits were covered with God only knows whose cum. It was okay thinking that it was my husband's cum, but finding out that it was someone else's cum is beyond gross."

"Well, it's over now. You're rid of him. Your ex-husband is gone and gone for good and never to darken your door, again. Now, it's time you got on with your life and put all of this behind you. Just as I'm doing with this cross-dressing, it's time for you to begin a new chapter."

"Of course, you're right, but apparently these men must have like me blowing them while they fondled my tits because they continued to return over and again and they continued to pay my ex-husband money for the pleasure of me attached to their cocks," she said looking at him with an expression of curiosity. "I wonder how much he charged them. I wonder how much money he made from my mouth and my big tits. Well, no matter, all the money he spent on all those entertainment toys downstairs are now mine to keep, should I ever get over my phobia of going downstairs and he did buy me a new car. Here I thought he was a generous husband and it turns out that I prostituted myself to buy my own car. He's such an asshole."

"Gloria?"

"Yes?"

"Uhm, speaking of downstairs...I was just wondering..."

"Yes?"

"Do you still have any tapes of you giving blowjobs or did you destroy them all?"

"Oh, you're just as perverted as the rest of them. You're no better than my ex-husband. You're pathetic. Yes, I still have them." She gave him a look of disdain and put a hand to her hip. "Why? You want to watch them, don't you?"

"Well, yeah, but only if you'd want to show them to me."

"You'd want to see me naked, handcuffed, and blindfolded while sucking off some guy?" She turned to face him. "Would that make you all hot for me?" 

"I'd just be curious, is all. Actually, who wouldn't want to watch those tapes and I'm already hot for you and watching that would make me more so," he said with a nervous laugh. "It's probably every guy's fantasy to watch his wife on her knees giving a blowjob to someone else while handcuffed and blindfolded.

She put her hand on his cock and felt him through his underwear. 

"Do you mean curious or hot enough to get an erection like you have now."

"Okay, I admit it. It would make me hot to see you naked, handcuffed, blindfolded, and on your knees while you were sucking off some guy."

"So, hearing about me sucking off men turns you on?"

"Oh, God yes, only if you were my wife, I might imagine you doing such a scenario, but I would never mistreat you in the way that he disrespected you. I would never do that to you; trick you to give another man a blowjob, if you were my wife. If I wanted to watch you blow another man and if that was my fantasy, I probably would feel you out about it with some hot pillow talk. If you were averse to giving other men blowjobs, well, that would be the last time that I'd mentioned it. I'd never do what your ex-husband did to you. What he did is like those fantasies that you read about online at one of those erotic story web sites."

"Well, if hearing about me sucking off other men gets you all hot and bothered, I can't imagine what you'd be like if you saw me sucking off men." She looked at him and gave him her best sexy smile. 

"I'd probably cum in my jeans," he said hoping she'd take the bait and show him a tape of her sucking of other men. There was a long uncomfortable silence before Gloria spoke again.

"Would you like me to suck you off, too, while we watched a tape of me giving other men blowjobs? "She pulled down his briefs enough to expose his erection and then wrapped her hand around it while gently stroking it stiffer. "It would be like watching our own personal porn movies with me as the star."

"Are you serious? Oh, God, yes. I would love for you to suck my cock while I watched you sucking the cocks of other men. That would be so hot."

"Only, I don't know if I can blow you. It's been a while since I've given anyone a blowjob. I'll try, though, if you want me to blow you."

"Oh, yes, try, please try."

Gloria went downstairs and returned with a tape. She loaded it in the video player and waited for the image to appear on her big screen television. At first the tape showed a handful of guys standing around the big room downstairs talking, laughing, and drinking. Then, the lights went out and it showed her ex-husband leading Gloria down the stairs and escorting her down and around the basement.

There was loud music playing in the background. Except for a few night lights, the room was totally dark and it was more difficult to see because everything was so very dark. Still, her figure could be identified by her massive boobs. He had never seen tits so big. They were enormous and they only sagged a little bit. His wife's A cuppers sagged more than Gloria's double D's. He realized that he hadn't even thought about his wife since he's been here with Gloria. He was starting to develop real feelings for her.

He refocused his attention back to the big screen television. There she was walking beside her ex-husband as he led the way to the room behind the bar. Everyone was so quiet. Except for the blaring music, you couldn't even hear a whisper. Then, once she was in the room, there were cameras everywhere capturing the action while she was on her knees. Within a couple of minutes a cock appeared through one of the holes.

"I'm ready, Gloria," said her ex-husband.

Only, it wasn't his cock that was peeking out the hole. It was someone else's cock. Her husband stood off to the front side of her watching her sucking off another while he unzipped himself, pulled out his prick, and started masturbating to the sight of her giving a blowjob to one of his friends or one of his brothers or who knows who she was doing.

It was very hot to watch her skillfully give a blowjob with just her mouth and without using her hands. It was an amazing feat. Within only a few minutes the man shot a load of cum in her mouth. Then, her ex-husband pretended to come around the holed wall by opening and closing the door. He helped her up, gave her something to drink, kissed her, and then whispered something in her ear. Within a few minutes she was back down on her knees again sucking someone else off. The whole process lasted about an hour. It was well orchestrated and Bob could understand how being blindfolded in the dark for a period of time, you wouldn't know where you were after a while.

"What did he say to you?"

"He said that was so great, baby, only I didn't shoot my whole load. I'll give you a few minutes before you can suck me off, again. Normally, he'd wait fifteen minutes or so and tell me that he was ready to go again. It was part of our agreement that I'd suck him off for an hour, no matter how many times he got off. Only, in the dark and wearing a blindfold, I had no sense of time. I could have been on my knees for an hour or for three hours for all that I knew."

"You weren't suspicious that you were sucking off someone else?"

"No, when you love someone, you trust them. I had no idea I was sucking off different men. How would I know that? I thought we were alone in the house. I had no idea there were men downstairs in the basement watching me give blowjobs on the big screen television. I only thought I was blowing my husband. Besides, with it being so dark and not being able to hear anything with the music playing in the background and not being able to feel the cock in my hand because I was handcuffed, I had no way of knowing who the Hell I was blowing. You lose all references of where you are. He never removed the blindfold and/or the handcuffs until I was back upstairs. Most times he kept that door locked and he had the only key, that is, until I threw his ass out and had a locksmith remove the lock from the door."

"I still don't understand. How did all these men get downstairs in the basement without you seeing them enter your house?"

"That's easy. There is an outside entrance to the room that leads out to the back of the house. All they had to do was to park their cars a street over, walk through my backyard, and go in through the back way. My husband unlocked the door for them to enter."

While he watched her on video sucking off other men, she fell between his knees, pulled down and off his briefs again, and took his stiff prick in her hand. Slowly she stroked his cock while staring at it before taking it in her mouth, engulfing it with her lips, and sucking it while twirling her experienced tongue around it. Her mouth felt incredible. Never had he received such a blowjob. She sucked him like a vacuum. No wonder why these guys shot their loads so fast. She was an experienced professional at sucking cock.

"You have a big prick, Bob. It's much bigger than my ex-husband's cock," she said removing his cock from her mouth to speak before reinserting it again. "I like sucking your cock better than all of those other men I sucked."

He shot a load of cum in her mouth within three minutes. Never had he cum off so fast from a blowjob before. He calculated if she was this good to get him off within three minutes. She may have blown more than a dozen men in an hour and fifty men within one evening. He extrapolated his imagined totals for the year. She may have given more than 18,000 blowjobs and if her husband had modestly charged $25.00 for a blowjob, no doubt, he charged more, though, but at $25.00, he would have earned $450,000 for having her give 18,000 blowjobs. He wondered how many she did give.

Now, with the Happy Halloween Cross-Dressing Bash tomorrow, Bob kindly accepted Gloria's invitation to stay the night. Since she lived alone, she left her three bedroom home as a one bedroom. She converted the second bedroom to her office and the third bedroom was used to make the media room downstairs. With only the one bedroom and no other bedroom to spare as a guest bedroom, other than the couch, she invited him to share her bed for the night. They had hot sex.

Finally, Bob was able to spend some quality time with her tits. He kissed and kissed her while fucking her. He was all over her big boobs, touching them, feeling them, caressing them, and sucking her nipples. Her tits maintained his erection. Never had he been with a woman who had such big tits. He loved her big knockers.

He ate her pussy. He made her cum with his mouth and made her cum again while fucking her and making sure the length of his cock rubbed against her click every time he humped and pumped her. Then, she blew him again. He didn't think he could cum again. He had already cum twice, but she sucked the cum right out of him. She was so much more sexual than his wife and he loved it. This, by far, was the best sex he had ever had and he wanted a steady diet of this and her. 

He already decided to ask his wife for a divorce as soon as he got back home after the Halloween Cross-Dressing Bash. It was different with Gloria than it was with his wife. He didn't have to lie, hide, and sneak around about wanting to dress like a woman. Gloria not only already knew that he was a cross-dresser but also she was okay with it. Further, she owned a woman's clothing store. Moreover, she gave him the best sex and the best blowjobs he ever had. She was his perfect woman.

The next day, she helped him primp for his Halloween Bash. Between helping him comb out his wig, do his makeup, paint his nails, it was a four hour process. He took longer than a woman to get himself ready. It's a good thing they started early and the dance was late.

Of course, he invited her to join him and she was happy to go. It had been a few years since she attended one of these events with her brother. Bob paid for her ticket at the door. As soon as she entered the large hall, she recognized many of the people in attendance as those who attended the couple of times she accompanied her brother. Less than half the men were with their wife, girlfriend or significant other. It was apparent that no everyone had an understanding woman as he did now having Gloria in his life. She pointed out the ones she knew and several cross-dressers gave to her table to give their condolences.

"Gloria! How are you?" A tall man with shapely legs ran up to her, gave her a big kiss on the lips, and hugged her.

"This is my friend Bob. Bob, this is Anthony." The men shook hands.

"I heard what happened to your brother. I'm so sorry," said one man who came up behind Gloria and gave her a hug while she was talking to Anthony. He looked good enough to be a woman.

"Mark, this is Bob." They shook hands.

By nine o'clock dozens of cross-dressers poured in. Many were dressed in outrageous and colorful ensembles. With all the boas, feathers, hats, and high heels, it looked more like a Halloween Masquerade than it did a cross-dressers dance. The cross-dressing men who attended the Halloween bash were not subtle in their fashion taste with some wearing mini-skirts, low cut tops, and even formal gowns. This was their evening to go over the top and they did.

In the beginning, the men separated themselves off in common groups. There were those who looked good enough to be women and had you not known that this was a cross-dressers bash, you would think and mistake them for women. There were those who were gay, those who were post-op transvestites, and others who were pre-op transvestites. Then there was another group who were dressed as women but who looked like men. Many of the men in that group were well over six foot tall, especially with their high heels. Then, there were a group of men who looked much like Bob. They were men with beards and mustaches. 

After the music started playing and cross-dressers started drinking and mingling, the groups blurred into one massive scene of cross-dressing men. They all appeared to be enjoying themselves. Everyone looked happy. Bob made a lot of friendships that night while Gloria passed out discount coupons to her store.

*

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