10 comments/ 119494 views/ 31 favorites Dressed for Sex By: call_me_dana This is a prequel to the Sissy Nicky story ... "Thanks Dana, I'm glad you could get here on such short notice." "No problem Angie, I'm glad I could help you out." "I'd have waited until Nick got home from his trip, but I really needed to get the laundry started and I haven't had water all weekend." "Why don't you show me to problem and I'll see what I can do." Angie backed away from the door to let me inside. As she did, it was evident she wasn't wearing a bra under her loose t-shirt. I really didn't think anything of it as we were old friends and she was trying to get her chores done on the weekend, but I did notice the way her ample breasts swayed under the t-shirt. Angie led me to the laundry room. I pulled the washer away from the wall so I could take a look. "Do you have some old towels I can use to soak up the water?" She went into the garage and returned with some beach towels. I spread the towels around and soaked up most of the sitting water. I turned the valve off for the washer then unfastened the water hoses connected to the washer. As I suspected, the hose had cracked near the washer. "Hey Angie." I walked towards the kitchen to find her. I rounded the corner to see her bent over at the waist. Her shorts were riding high up her thighs and the unmistakable 'V' from her thong bikini was evident. I paused and took in the view before speaking. "I just need to replace this water hose for you. I'll run over to Home Depot. Do you want me to replace them both? It'll be about $40, but the other one is just as old." "Whatever you think Dana. Here's some cash, just let me know if I owe you more when you get back." It took me about forty minutes to get over and back with the hoses. Angie let me back in the house then went off to do her own thing. "It'll only take me about ten minutes." I was on my hands and knees collecting my tools when I heard heels clicking on the tile. Angie stopped just in front of me. Her toenails were painted bright red and she wore five-inch heels. My eyes slowly moved up her bare calves, then her knees, then her thighs. She was wearing a very short red robe. "Thanks for fixing this for me, Dana." As she spoke, she slowly pulled her robe open to show me the very skimpy red lace teddy on her body. Angie has very nice curves and great breasts that were exaggerated by the teddy she now wore. I wasn't sure what to say, but I couldn't look away either. "You know this is the position a man should always be for a woman. Do you think I look sexy, Dana?" "U-h-h, very sexy. In fact too sexy for just the two of us to be here." "Relax Dana. Nick's not due home for hours. Remember that's why I called you to help me." I couldn't take my eyes off the 'V' of her high-cut teddy. It exposed her high hips and made it very evident that her pubes were closely cropped or non-existent. "I've thought about you and those conversations we've had about you getting all dressed up and having no one to play with. I want to see you!" I was getting nervous just being in this position, but I could feel my penis stiffen in my pants at the thought. "This isn't right. Nick's my best friend. Besides I don't have any of that stuff with me." Angie smiled and bent at the knees. Her breasts were just twelve inches from my face. She just sat there for thirty seconds letting me take her into my senses. "You've been a good handyman today and I want to thank you." From behind her back she handed me two white lacy undergarments. "Take these from my hand and go into the guest bedroom. You'll find a few other things for you. When you have them on, come into the family room and let me see." I hesitated, but the desire was too strong. I slowly reached out and took them from her. As I stood up, it was evident I was quite erect. When I was standing, my cock was straight out from Angie's face. She smiled. "You'll have to do something about this. The panties are not that big." I quickly walked past her and into the guest room. Once inside, I closed the door behind me. Even though I knew what was in my hand, I unfolded them and looked at what Angie had given me for the first time. It was a bra and panties set. The panties were actually a little wider in the front than I have bought for myself, but I figured she was guessing. I looked at the bed for the first time and saw matching garter and stockings. She even left me a little tube of lipstick. Although I don't usually use lipstick being home alone, it was quite intriguing. I went into the bathroom and washed my hands and face to get the dirt from the washer off of me. I stripped off my male clothes and folded them in a pile. My cock was still quite erect from my excitement. I knew there was nothing I could really do about it except to jerk myself off and I really didn't want to do that. I put the bra on first and adjusted the shoulder straps to fit. Next I fastened the garter belt and moved it into place. The stockings were shear and rolled smoothly up my legs. I quickly fastened them to the belt. Finally I stepped into the panties and pulled them up my legs. They were just a bit loose, but the extra space made it a bit easier to contain my erection in the panties. I admired myself in the full-length mirror behind the door. I was very pleased I had shaved my pubes that morning while showering. I like to keep most of my pubes shaved all the way to my anus. I have just a small amount of dark curls between my navel and my penis. I could see my hand shaking as I reached for the door. I'd never been seen by anyone else while dressed this way. The door opened and I knew I was committed. "Let me see you Dana." I could hear Angie call me from the family room in the back of the house. I walked down the hallway in my stocking feet. I tried to look nonchalant, but my heart was pounding with excitement. I knew she wouldn't laugh, but I didn't want to disappoint her either. I stopped in my tracks when I first saw her sitting on the love seat. "Don't be shy. Come closer so I can get a good look at your sexy body." Angie was casually stroking her breast through the teddy as she spoke to me. She was sitting with her back to the wall and her feet up on the ottoman. Her legs were parted and I could easily see the 'V' between her thighs. I moved to within four feet of her before stopping. I had entered the room with my hands in front of my crotch. "Don't be a silly. Put your hands behind your back and stick out your breasts for me to see." I did as she told me to and I could seemingly feel my penis grow in my panties. I could feel the moisture oozing from the tip as the silky fabric rubbed against it as I walked. "You look wonderful. Please turn around so I can admire your backside." I turned around and stopped for a moment. When I turned back around, I could see Angie had unhooked the teddy between her legs. Her shaved pussy was very prominently displayed for me. "Oh Dana. You were very modest. You look even sexier than you described to me. You did a nice job with the lipstick." "Thank you Angie for the compliments." Angie's left hand had moved down between her thighs and she was now lightly fingering her pussy lips. My eyes naturally followed her fingers. "You are making me so horny standing all sexy like that for me. I'm not making you nervous ... am I?" She was making me very nervous and very aroused. "U-h-h yes you are making me nervous. But please don't stop." Angie smiled a wicked little smile at me. "I've read your stories and know how much you love to lick pussy. Will you lick mine?" "I really don't think that is a good idea. What if Nick walks in on us?" "Relax silly girl," that was the first time anyone had referred to me as a female, "Nick called while you were out. He was still at the airport and he won't be home for another three hours. I told him you were taking care of my plumbing problem." Angie looked incredibly sexy sitting there with her legs spread and her fingers casually stroking her lips. "You know we both want you between my legs. Now get between my legs and show me how good you are." Her tone changed slightly, telling me she was in control even if I hadn't already felt that way. I slowly approached her and she kicked the ottoman away from her. She reached out and felt my erection through the panties with the ever-increasing wet spot. "You have such a big clit. I hope you let me play with it later." It jerked against her fingers and she smiled. "Now get on your knees Dana." I dropped to my knees and suddenly felt a little slutty. Angie spread her legs a little wider and I soon found myself inches from the heat between her legs. "Do you like to see my shaved pussy? It's so nice and smooth, isn't it?" All I could do was nod my head. I could smell her body's aroma. I leaned forward and tasted her lips for the first time. My tongue licked up and down the crack of her lips, not penetrating, just teasing them. "Ooh you are a bad girl. You're going to tease me, aren't you?" I moved my tongue up and found her clit for the first time. Angie let out a moan and her body slid down the chair closer to me by a couple inches. I used my tongue as skillfully as I had ever done so with a woman. Her body was very expressive and once I got her juices flowing, she had a very sweet taste. Occasionally I would look up at her to watch her playing with her now exposed breasts. Angie told me she loved to play with her large brown nipples and she was pulling and pinching them every time I looked. I had been between her legs for more than fifteen minutes when she clamped her thighs around my head and pulled me closer. I worked her clit with my tongue, biting it, sucking it and stroking it. When she could take no more, she started moaning very loudly before I could feel her muscles shake from her orgasm. "Oh Dana, you do love to lick pussy and you are so good at it. That was wonderful." She patted the sofa next to her and I sat beside her. We kissed for the first time. Her hand began to lightly stroke my fully erect cock through my panties. "Now it's my turn to please you. Sit here for five minutes then come upstairs to my bedroom." I looked at the clock to see when it would be five minutes but also to check that I still had two and a half hours before Nick would be home. Angie stood up and walked upstairs. I waited for exactly five minutes before getting off the couch. I had to do everything I could to keep from running up the stairs. I walked into her room to find the bed covers pulled down. "Lie down on the bed. I'll be with you in a minute." I looked around the room and saw nothing I hadn't seen in previous visits. Of course, this was not like any previous visit. Angie walked out of the bathroom with a surprise for me. She was nearly nude. Well, she was nude except for the nipple clamps and the harness around her waist. A large rubber cock extended from the harness and swung between her legs. "Uh Angie, I don't know about this." I kept looking at the size of the rubber cock and knew where it was headed. It scared me, but I found myself incredibly aroused. Angie crawled onto the bed. "Get on your hands and knees and show me how a slut sucks cock." Her tone surprised me. "I told you to suck my cock!" Her voice was louder this time. I got on all fours and took the head of the large cock between my lips. I started slowly as I had never been with a guy before and was really unsure. Angie pushed more of the cock inside my mouth and I soon had half of the rubber phallus between my lips. "That's enough. I know every slut likes to suck cock, but they really love to take it up their ass." I was really nervous now thinking it would split me open. "Turn around for me!" I wanted to do whatever Angie wanted. Angie actually got off the bed and stood with her feet on the floor. She grabbed my stocking covered ankles and pulled me to her. She slapped my ass through the panties causing me to lurch. She gave me four more spanks before she rolled the panties off my ass cheeks. The front of the panties was standing out like a tent. I could feel a cool liquid being squirted on the crack of my ass then her finger was pushing it around the rim and inside the sphincter. "You're gonna need to relax Dana or this will hurt. But you're gonna get fucked either way!" I was trying to relax but I was scared and excited and nervous. Finally I felt the tip of the rubber cock against the rim of my hole. She gave it a push and I felt the muscles began to widen around it. Even though she was talking tough, Angie was being gentle as she pushed more and more of the large rubber cock into my ass. I found myself moaning with pleasure as I dropped to my elbows. She had settled into a nice rhythm that had her pushing about two-thirds of the cock into me. "You've got a very fuckable ass Dana. Are you enjoying this?" "Yes I am Angie." She slapped my cheeks a few more times before reaching around and pulling my panties down over my erect cock. Angie tightly grabbed my cock in her hand. She gave it a couple strokes and I thought she would make me cum, but instead she grabbed it and hung onto it. "I've got a surprise for you Dana. Look up." I looked up and couldn't believe my eyes. Nick was standing in the doorway to the room. He was naked, his body covered with dark hair. I looked at him and I'm sure the blood drained from my face. I tried to move but the large rubber cock in my ass and Angie's grip on my cock held me on the bed. I realized if Nick was already naked, he was in on it and I'd been had. Then I looked at his tightly bound cock and balls. It had been years since we'd gone camping, but I always remembered the size of his penis. It was very thick compared to my much thinner version. "Nick's been watching everything. He watched his slutty friend get between my legs and eat me to orgasm." With his cock securely fastened by a steel cock ring against the base and his balls pushed being down by a four-inch leather strap, his privates now looked huge to me. "Come here and give me a kiss." Nick walked over to the bed and gave a deep and passionate kiss to his wife. "Okay Dana, I let you practice on mine and now its time to show Nick how good you can suck on a cock." "This is crazy. Nick, what are you doing?" Nick got on the bed in front of me, his huge cock bobbing in front of my lips. "Angie says I'm about to have a little slut suck on my cock. And I don't ever disobey Angie." Again I couldn't believe what was happening. Slowly I opened my lips and he pressed his cock against them. I took him inside my mouth as Angie returned to fucking my ass. "Good girl, suck on that big cock while I fuck you. You know you are so turned on by all this." I couldn't disagree with her. I had never been this excited in my life. I thought my own cock would explode from the rush of excitement, but it just continued to ooze pre-cum. Nick's cock was stretching the bounds of my jaw as he pumped it in and out of my mouth. "I'm getting tired and need to have my pussy taken care of again by this pretty girl. Nick, can you take my place?" Nick slid his cock from my mouth. "Don't move sweetie, we'll be right with you." I didn't dare move for fear I'd touch my cock and it would explode. Angie got on the bed stripped of the harness and put her shaved pussy in my face. I was surprised when I felt Nick's tongue dance around the rim of my asshole. He worked his tongue around the rim before probing it with the tip. That felt really great. But before I enjoyed it too much, I felt Nick's hairy legs behind me. I soon felt his large cock at the entrance to my ass. He pressed his thick cock against the rim of my ass and was soon pushing inside. "Just relax Dana, Nick's gonna make you feel really good!" Angie slid her pussy against my lips and my tongue snaked out and tasted her sweetness once again. Nick's cock was now three inches inside of me as he worked in and out of my ass. My tongue was lapping at Angie's wet pussy, her juices flowing to my tongue. Nick grabbed my hips and he began to stroke deeper inside of me and I was finding his thickness very comforting. Within a couple minutes, Nick was able to get most of his cock inside of me as he thrust. Occasionally his bound balls would swing up and hit mine. It was a really weird sensation. I looked up at Angie. "I need to cum Angie. I feel like I'm going to explode!" "I'll make you a deal. When you get me off, I'll let Nick cum. After that, he'll show you how to suck on a cock. Does that sound like fun?" I didn't even answer, I just dove into her pussy. My tongue was now flicking her clit like there was no tomorrow. Angie began thrusting her hips up to meet me as my tongue feverishly lapped across her swollen clit. "That's it. Make me cum. Make me cum." Just as she felt her orgasm, Angie pulled the clamps from her swollen nipples and let out a tremendous yell. The blood rushing back to her nipples was electric. The sensation pushed her over the top and her pussy thrashed against me. My face was soon covered with her juices. The next sensation I felt was Nick filling my ass with his warm cum. He shot at least three long streams inside of me. I ground my hips back against him as he continued to stroke inside my ass. I knew it was my turn. "You've been such a good fuck Dana. Now it's time for your reward." Nick exited my ass and the two of them helped turn me over. Nick got between my legs and pulled my panties down to expose my cock. I knew I was so close that I'd probably cum as soon as he touched it. I tried to think about anything but sex. Nick's tongue was very soft on the underside of my cock. He licked at my balls and around my shaft before finally taking me inside his mouth. Angie was squeezing my 'breasts' as Nick worked his magic on my cock. I was soon shooting cum into his mouth. It seemed like I would never stop cumming, as I had been so excited for so long. We finally all lay on the bed without saying anything. "That was incredible guys. I can't thank you enough for this. It feels so great to be able to get dressed like this with an audience. And the sex ... you two are unbelievable." We eventually all showered and Angie suggested we grab dinner before I drive home. She did tell me to wear my new undies to dinner and based on the afternoon, who was I to argue? Dressed for Success I’ve been a professional wrestler for about two years now. And no you haven’t seen me on TV I’m not that good yet. I wrestle in the Ohio Valley Training Center. That’s were all of us kids go to train for the big shows. RAW or SMACKDOWN. One of the things I enjoy most about this job is the testosterone level of my fellow workers. Everybody has an attitude and everybody is willing to share it. Now there are two real hallmarks in this business, the ribbing (Practical Jokes) and the Bets. If you make a bet in this business you have to pay up. Some of the major bets I’ve won have included making my buddies pay for dinner, eat soap, and wash the car of everyone at the training center. That was over one hundred cars. So over all I’ve done pretty well. I’ve only truly lost one major bet. I was in a match with one of the girls and the testosterone was flying. I thought I’d beat her easily and I told her so. She asked if I wanted to bet and we were off. I said yes if I won she went on a date with me. She agreed so I upped the ante. She was always wearing jeans, so I told her if I won she had to wear a dress. She said fine if she won so did I. I should have let it go but I’m a little temperamental. I added to the bet saying that she had to get the phone numbers of two girls who would go out with her while we were out. She nodded and informed me that I’d have to pick up two guy’s. I agreed to the bet and we got down to wrestling. I won’t bore you with the details of the match but due to a little outside interference by the guy who washed the cars, I lost the match and the bet. Everyone was laughing when I lost. The announcers had made a big deal out of the match and all the fans were really into it. It was even worse in the locker room. My locker was strung with bra’s and the guys were gather around to snicker at me. I decided right then and there I was going to do it right. Well it’s been almost a week since the match and we are going out tonight so that everyone will have something to talk about at the matches tomorrow. I’d put a lot of work into this outfit and all I can say is thank goodness for Lane Bryant. They make clothes for bigger women and enough of them fit me that I was able to buy something stylish. They were even able to help me out in the undies department. I’d bought an aqua bra. Nothing like having a little cleavage and a Binicki or butt bra so I’d have a little tush. Over this I put nylons, hi-heels, and a Japanese dress that brought out the highlights in my hair. Now I don’t want you to think I just looked like a man in a dress. I’d gone to a salon and I’d spent several hundred dollars for the best makeup job I could get. In addition to the shave and the make-up I had had my hair done. It was interesting to watch as the girl shaped my hair into a very feminine looking haircut. I’ve always had long hair but I’ve always had a square cut mane. And then she added color to a few select strands of hair and wrapped them in foil. The effect when I was done was stunning. I got lots of looks on my way home, although whether that was because I looked so good or so bad was hard to tell. That night was worth the effort. I loved watching my dates jaw drop as I walked in to her apartment. I did a little pirouette and believe me that’s harder than it looks. She was just amazed at how good I looked. She had to admit that if she didn’t know who I was, she might try to pick me up herself. We headed off for Zeke’s Bar and I had to say I was looking forward to it. As we pulled in and got out of the car I could already see a few guy’s looking our way. I felt her take my hand and we proceeded into the bar. We passed quite a few guys and as we got closer I felt a hand on my ass. I turned to look and found this toothless guy hanging onto me. I gave him my best smile and pointed at the ceiling. He couldn’t help himself and looked up to see what I was pointing at. My openhanded slap sent him flying, all his buddies laughing at him. As he stood up and started back at me I asked him what his friends would say if a girl kicked his ass. He stopped and rethought his plan. Next thing I know we are surrounded by guys all willing to buy us drinks if we’ll just sit and talk with them. I actually got thirty some odd numbers in just the first hour we were there. My date just couldn’t believe it. It actually went to well. I met a small guy I really liked. He was somewhat smaller than I was and thin as a rail. He had very fine features and was a great conversationalist. We got started talking and it was as if everyone else disappeared. I think we talked for several hours. He finally excused himself to go to the bathroom. I needed to go as well and went after him. I was kind of lightheaded after all that alcohol, I didn’t notice that I’d followed him into the Men’s room. He went into a stall and I followed out of embarrassment. I’d seen other girls do this and laughed as I realized the other girls would think me a slut. He turned in surprise to see me and I kissed him full on the mouth. He pulled me into the stall and shut the door. My tongue reached for his but he stopped me. He told me I needed to know something before we went any farther and dropped his pants. I was extremely surprised to find out ‘he’ was a woman. I saw the hoping expression on his face and I told him we were made for each other and pulled up my dress. He reached out and pulled me to him. I spun us around and my already hard dick escaped it’s covering and in no time at all we were having really good sex. Every time someone banged on the door I’d yell out for him to go away. It was intensely erotic to know that all that protected us from those guy’s was a small steel door. As we left the bathroom He pinched my ass and smacked a sharp blow. We went home together that night and we go out again every once in a while. He really is the best thing that'’ ever happened to me.” Dressed for Success "And can you take dictation?" Harry asked. He watched the eyes of the young man across the desk as he asked the question. Harry liked to watch people's eyes when he talked. The way a person's eyes widened or narrowed sometimes told more about them than a whole résumé. George's eyes widened. Not quite 'deer in the headlights' quality widening, but Harry knew he'd hit a vulnerable spot. "I've not had much opportunity to practice, Mister Keel," he said, rallying, "but I've taken dictation in business courses. Do you expect it to come up often?" "Not in a formal sense, no," Harry said, jotting down a quick note for later. His desk had almost a dozen folders sitting on it now, with dozens of nearly-illegible notes on each candidate in each folder. This kind of mess was half the reason he was looking for a personal assistant to begin with. "But you will be expected to keep an ear out for my conversations for anything that I might need to be reminded of later on. After all, I'm hiring you to keep me on track. That starts with knowing what the track is." George nodded, visibly relaxing while trying not to look like he was visibly relaxing. Harry jotted down another quick note, but he watched George's eyes while he did it. Sure enough, Harry could see just the tiniest touch of panic in them. Harry wasn't sure he wanted someone who got rattled that easily. Then again, his standards might simply be too high. Harry really wanted a personal assistant like the one billionaire industrialists had on television shows, the kind who instantly and effortlessly anticipated their bosses' every need as though they had some sort of telepathic link with them. The kind that finished your sentences for you, showed up with coffee before you asked for it, and bought your wife flowers on your anniversary when you'd forgotten what day it was on. (Or when you bought them on the anniversary of your marriage to your second wife, he thought ruefully. Oh well. There'd probably be another woman along in a few months.) So far, though, he'd just gotten a succession of men and women like George, here, a group of competent middle managers who thought the job was something like a glorified secretary with a bit of gofer mixed in. While those certainly were among the job requirements, Harry knew his personal assistant would need to be able to handle a lot more. They'd need to be able to keep him focused on the little details before they became big problems--sure, his habit of wool-gathering and brainstorming had resulted in a number of the innovations that made Even Keel Enterprises the hot tech company it was today, but you can only forget to eat so many times before it catches up to you. And George, here? Was he really going to be able to challenge Harry when he decided on something impractical? Was he going to be able to assert authority over his own boss when Harry tried to book three different meetings for three different cities in the same day? Probably not, Harry decided. He doesn't even seem to know how to handle it when his boss gets totally lost in thought in the middle of an interview. "Thank you, George," he said, a little animation returning to his features as he returned to reality. "Naturally, I can't assess your chances before I've interviewed all applicants, but rest assured your qualifications have been most impressive." He stood up and shook George's hand. The grip was firm, the smile was genuine, but Harry could see in George's eyes that he knew he hadn't gotten the job. "Thank you, Mister Keel. It's been an honor to meet you." Keeping the smile firmly in place, George turned and marched out of the room. Harry sat back down and jotted a few more notes on George's performance. Absently, he reached out and tapped the intercom. "Send in the next applicant, would you, Nadia?" A crackling buzz on the other end indicated compliance, and Harry went back to scribbling notes. He didn't know why he bothered, really. It would only go on top of the pile. It was so much harder to organize paper files than it was to organize virtual ones--but then again, it was easier to write notes on paper. Hand-writing recognition software was a joke. What he needed was a way of converting files back and forth between paper and virtual quickly and easily. Some sort of combination shredder/scanner/printer, perhaps? He thought about it, accidentally starting to write down ideas for the machine on George's job application. A device that could scan hard-copy files, store them in virtual form, then reconstitute them into printed form on request. A sort of post-paperless office, as it were. The real question was, could you recycle the paper efficiently enough to reconstitute the documents again and again if-- "Your coffee, sir." A woman's shadow fell across his desk. "Harar Sumatra blend, no cream, two sugars. I read in 'Geek Monthly' that it's your preferred drink?" "Thanks," he said, writing a reminder to himself to talk to paper manufacturers on Monday. He paused for a second as his brain caught up with the conversation. Then he looked up. After looking up, he looked up quite a bit more. The woman standing in front of the desk loomed over him, six-inch stiletto heels adding to her already-considerable six feet of height. Her honey-blonde hair was pulled back into a tight ponytail, which only emphasized her air of authority. She had pale blue eyes, but for the first time in ages, Harry didn't look much at her eyes. He was too busy looking at her outfit. She wore a black vinyl peek-a-boo bustier that displayed a generous amount of cleavage, and an even more generous amount of toned mid-riff. Below that, a matching black vinyl skirt only came down to her thighs, but Harry didn't see much in the way of exposed leg because those six-inch heels were on shiny black leather boots that came up almost all the way to the hem of the skirt. She held a riding crop in one hand and, incongrously, a cup of steaming coffee in the other. Harry's jaw hung open for a long moment as he stared at the woman in black. No matter how hard he tried, he couldn't seem to process it. There wasn't anyone else in the room, this had to be the next applicant, but...she couldn't be. It had to be a joke of some sort...but who would play it on him? "Mister Keel?" she said briskly. "I think we should probably get started. I'm Eryn Zane." She set the coffee down on the desk and extended her hand. He noticed, even as he automatically reached out to shake it, that she wore long black vinyl gloves that came up to the elbows. "I'm here to be your new personal assistant. I've already read the brief you provided on the job requirements, and I'm not afraid to say that I can handle them admirably." Harry blinked. "Um...you, you're serious?" he blurted out. "You're really here for the job?" "Of course, Mister Keel," Eryn said. "I'm a great admirer of yours. You're intelligent--a visionary thinker, in fact, if I might say so. You're also personable and friendly, with a good sense of humor--all desirable qualities in a boss, especially in a position that requires as much personal interaction as this one. And by all accounts, you're scrupulously ethical and fair in your business dealings--definitely a desirable quality in a boss. All you really need is some guidance on a day-to-day basis." She waggled the crop just slightly, causing the end of it to quiver alarmingly. "A...firm hand, as it were." Harry simply goggled at her. "You're really serious?" he said. He knew he was being rude, but frankly, she couldn't have expected any other reaction under the circumstances. "But--but your outfit--" She looked down at herself, clearly quite proud of what she saw. "I understood that it was common practice for people to dress for interviews in a way that made them look confident and powerful. I think you'll agree that this fits both those conditions, yes?" "Well, I--" Harry had always heard that one should dress conservatively for job interviews, but as a founder of his own company, he'd never actually had to go to one. "I mean, I guess, but--" "Then we'll speak no more about it," Eryn said, punctuating her words with another tiny wave of the riding crop. "After all, my job will be to keep you on track and focused. What kind of a job would I be doing if I let you spend the entire interview chatting with me about fashion?" She walked around the desk, showing an easy grace that impressed Harry despite the sheer insanity of the whole thing. She must have practiced a long while to be able to walk so well in those heels. "Naturally," she said, coming around to stand directly in front of him, "I assume you've already looked at my qualifications for the position, at least those on paper. But I suspect you've already determined that the real assets that matter for this job are entirely intangible." She leaned forward slightly, exposing certain assets that were a little bit too tangible, and Harry shifted slightly in his seat. Standing this close, she looked a lot more imposing than she had on the other side of the desk, and that was saying something. She towered over him in those heels, her outfit giving her an air of firm command without detracting from her sexuality in the slightest. "A man as intelligent as you has already determined that what you really need isn't a paper-pusher or a glorified secretary." Harry started a little as Eryn echoed his earlier thoughts. "You need someone to take control of things. You need someone to bring discipline to your day-to-day routine, Mister Keel." She tapped the riding crop gently against her thigh as she spoke, and despite his best efforts to drag his gaze up to her eyes, Harry was drawn down to the gleam of the office lights on the vinyl that encased her long, shapely legs. "You need someone to take charge of you, Mister Keel, and free you to be the best person you can be." Harry started to open his mouth to tell her that he was looking for a personal assistant, not a personal controller, but he'd barely gotten the beginning of a sound out when Eryn snapped the crop down against her thigh rapidly, producing a sound that startled him into momentary silence. In the pause, Eryn took charge of the conversation. "You've always needed someone like me, Mister Keel, even if you haven't let yourself know it. You've been waiting for me to walk through that door your whole life, in fact." She shifted position slightly as she spoke, just enough to cause the light to glisten off of her outfit in ways that drew attention to her figure. "You're so easily distracted and your mind is running in so many different directions that you don't even know what you really want. And all along, you've needed a strong, powerful woman to take control and tell you what to focus on in a way you can't ignore or argue with. You need to let me direct you." She slowly stroked the crop all the way down to her knee, then back up to the hem of her skirt. "It will simplify everything." Harry wasn't sure whether to be furious or turned on, so he settled for both. "Now look here," he said, "I'm not 'easily distracted'!" The most frustrating thing was that right up until he'd heard someone else say it, he'd been thinking almost the exact same thing. But he wasn't about to let someone walk into his office and tell him that, especially not someone who was...was... "Oh, really?" Eryn said, breaking into his train of thought. "Then this doesn't distract you?" She pulled down the zipper on the bottom half of the bustier, letting her breasts hang open. Harry gulped. Before he could speak, Eryn pre-empted him again. "See? You're totally lost for words. Just the sight of my breasts sends your mind into a distracted haze, while I'm still completely focused, completely in control. Which one of us is in charge right now, Harry?" "I--I am," he said. And he was, even if his cock had gotten quite a bit harder since the conversation had started, Even if he wasn't quite sure what part of her argument was wrong, exactly. Even if he still didn't seem to be able to look her in the eyes while that outfit kept directing his attention to every other part of her body. Even if exposing her breasts didn't make her look any less like she could order him to kneel at any moment and he wouldn't have any choice but to do it... "No, you're not, Harry," Eryn said firmly. She didn't sound angry, simply...commanding. "You're not in charge of your eyes, Harry. They're still staring at my tits." Harry finally jerked his eyes away to stare up into hers. "See? Now I told you to look somewhere else, and you did. You were distracted, you weren't thinking clearly, and I took command and helped you. You needed me to tell you what to do. And that's nothing to be ashamed of, Harry. You just need to accept it." "But I--" Another sharp tap of the crop stopped him mid-sentence. He couldn't help but be nervous, even though he knew she wouldn't actually use it on him...would she? "You're not in control of your cock, either, Harry," she said, taking advantage of his hesitation again to dominate the conversation. Knowing she was doing it didn't help him, either. It only made her arguments more convincing. "Your cock has decided to stiffen...and throb...and ache with need, Harry, and you can't stop it. Your cock wants me to take charge, and it's not listening to you. It's listening to me. Your cock has already let me control it. And the harder it gets, the harder it is to deny me." "This, um..." Harry's voice sounded weak and lifeless in his own ears. "This is...inappropriate," he stammered out. He was aware that he'd just conceded huge chunks of the argument to her; but he wanted to get her out of here now, before he did something foolish. His eyes were already beginning to water from the effort of looking up into hers, and it didn't help that she'd positioned herself so that her breasts were exactly at eye level. But staring at her breasts would mean admitting that she was the one in control. Or did staring up at her eyes mean that she was the one in control? "Don't be silly, Harry," she said. She sounded like she was chiding a favorite pet. "We're going to be working together very intimately over the years to come; a certain degree of familiarity is simply unavoidable." She unzipped her skirt and let it fall to the ground, revealing a pair of vinyl panties with a zipper of their own. Harry couldn't help himself. His eyes dropped down to her crotch, all on their own. "You'll become quite used to the way I look..." She reached out and took his hand in her own. He felt somehow like he should pull away, but she just seemed to be guiding it right to where he already wanted it to go. "The way I feel..." she said as she pressed his hand to her pussy and rubbed against it. He could feel her warmth through the vinyl panties, but somehow she seemed far more in control of her obvious arousal than he was. He'd given up trying to conceal his erection at all, now, letting it form a tent in the crotch of his slacks. She guided his hand to pull the zipper down now, and Harry found himself so engrossed in exploring the warm, wet folds of her cunt that he didn't even notice she'd let go of his hand until he felt her vinyl-covered fingers entwining in his hair. "The way I smell..." she said, pulling his head closer to her pussy. Involuntarily, he inhaled when he heard her words, and the scent of her arousal made his cock twitch. He could feel pre-cum dribbling down the shaft and soaking into the fabric of his pants. "The way I taste..." she said, pressing his face to her crotch, and Harry really couldn't do anything but lick. He knew she wanted him to lick, and he knew that meant that he was doing what she wanted...again...but there didn't seem to be any real alternative. There never seemed to be any real alternative to her decisions. She just removed all the objections, all the distractions, until the only thing in his world was her smell and her taste and her words. "We'll be working this closely all the time, Harry," she cooed as he licked her pussy. "You'll be so happy to focus on the things you need to focus on, Harry, because your cock will remember all the wonderful rewards I'll give it. It's going to feel so good, Harry, and you can already feel your cock swelling and throbbing, because it knows I'm in control. And you feel so good when you give in to your cock and your cock gives in to me. You feel so good when you accept my control, Harry. It's what you need. It's what you always need. You were born to be mine, Harry. Born to be...mine..." He felt her juices flow freely onto his tongue, and he shuddered in pleasure. He felt like he was lost in warm, dreamy pleasure--it just felt so nice to do what he was told and drift in lazy, sexual heat as he obeyed. Eryn pulled his head back abruptly. His eyes couldn't quite seem to focus as he tried to adjust to the sudden change. "Now, Harry, let's talk salary." "I, uh, um..." The sudden shift to clinical business discussions left him even more confused. His cock still ached, rock hard inside his pants. Desperately, he tried to remember what he was planning to offer, but dollar amounts jumbled together with visions of black vinyl and the taste of pussy in his mind. "A hundred...and, um..." Eryn cut him off again before he could even work out the rest of the figure in his head. "Absolutely unacceptable," she said firmly. "Stand up." Something in him almost reasserted himself there, but one look at those stern blue eyes told him that Eryn wouldn't tolerate it. Even without her skirt, even with her pussy juices smeared on her panties, she presented such a total picture of dominance from head to toe that his legs seemed to take the decision away from him completely. "Good boy," she said as he rose to his feet. She stepped around him and sat in his chair. Even sitting, she somehow seemed taller than him. The boots made her legs look longer, sleeker, more powerful. "Now, off with your pants." He froze, his mind making one last effort at reasserting control. "I--" Eryn slapped the riding crop down on the arm of the chair, full force. "Off with your pants," she said with icy precision. She didn't speak any louder, but somehow Harry knew he had better not force her to repeat the command again. He undid his belt and pulled his pants down, stepping out of his shoes as he did so. After a moment, he pulled his boxers off as well. "Good boy!" Eryn said warmly. "Now, come lie on my lap. Face down." Harry looked nervously at the riding crop, but disobedience wasn't even an option anymore. He complied, shifting position awkwardly to get as comfortable as he could with his ass directly on Eryn's lap. His cock rubbed slightly against the slick vinyl of her boots as he moved. Even though he knew it was coming, the first smack of the crop came as a surprise. "Now, Harry," Eryn said as she spanked him, "I know you want to make me happy." Harry jerked as he felt the crop come down again. "And I know you want to pay me as much money as you can afford to. That's not the issue here." Even through the sharp blows of the crop, Harry felt the pleasure building as his involuntary motions caused his cock to slide back and forth against Eryn's legs. "The issue is that I'm supposed to be keeping you on track. I'm going to have to assert authority over you like this--" She punctuated the words with another stinging crack of the crop. "On a regular basis." Harry whimpered, no longer sure whether he was frightened or aroused by the thought. "Now how can I do that if you're my boss?" There was a long silence. Finally, Eryn slapped his ass again, and he yelped. "Sorry!" he said, as he finally realized she was waiting for a response. "I, I don't...I don't know." Harry didn't know much of anything anymore, not between the throbbing in his cock and the entirely different, but somehow equally pleasant throbbing of his ass. Dressed for Success "Exactly," Eryn said with another smack of the crop. "So obviously, I'm going to have to be your boss. It's just a formality, really." She brought the crop down on his ass again, and he could feel her legs shifting underneath him. He realized she was doing it on purpose, moving barely enough to stroke his cock with her soft, smooth boots. "I'm already completely in control; we've established that. So we'll simply have to fill out some paperwork to make that official." "I, unnh, ohhh..." Something about that didn't sound quite right to Harry, but he was so close to the edge now, and every time he tried to think it through she swatted him again, and soon his mind crumbled down into sensation and he moaned out, "Yes..." "Very, very good, Harry," Eryn said, patting him with a relentless series of light blows all over his ass. "And you don't need to worry, Harry. I really do admire you. And I'm going to take very...good...care of you." She wiggled her hips one last time, and Harry couldn't take any more. He felt his balls tighten and he came hard all over Eryn's boots. "And just think," she said as she gently petted his back, "they say you can't get good help anymore." THE END Dressed for Suck-cess I had met my new friend just before Christmas, and we had already played a couple of times before today. However, it kept getting hotter, and today it was just too hot not to write about it. If you've read any of my other stories, you'll know that I'm an older bi married white male living in west central Texas. I don't usually write about events involving cross dressing, as I don't do it often, but I do enjoy it occasionally. It's hard to find guys who like another guy to dress for them, let alone guys who want to do it as well, but I lucked out this time. He is in his early thirties with a sexy muscular body, and he loves dressing and being sucked by someone who is also dressed. Lucky me! After weeks of trying to align our schedules, we were finally able to hook up today. In anticipation of his arrival, I was wearing a white silk teddy with snaps at the crotch for easy access, and contrasting black crotchless stockings. He asked me to have something ready for him to wear, and I selected a pair of dark thigh-high stockings, a sexy red teddy, and a silky thong in black with red and pink hearts. As I waited for him to arrive, I sat back on the couch and rubbed my satin-covered cock, picturing myself on my knees feasting on his thick cock. I hadn't waited long before he arrived. Once inside, we exchanged pleasantries as he undressed and put on the sexy lingerie I had waiting for him. In a few moments he was dressed, and we stood close while I fondled his cock in the thong. He was hard and ready, and I wasted no time in having him sit on the couch. He spread his legs for my camera as I took a picture of him, stretching the thong with his huge erection. He then spread the thong away from his cock as I took another picture, and then set the camera down and began to enjoy his cock. I knelt before him, my own cock straining against the satin as I leaned to kiss his beautiful penis. He moaned at the contact, arching his cock forward into my mouth, as I enveloped the head with my lips and began to slowly suck. I worked my way down his shaft, not stopping until it hit the back of my throat, then slid my lips back up to the head and began to suck. His cock tasted so good, and I had waited more than a month since the last time we played, that I began combining sucking, licking, and nibbling his head and shaft. I then pulled the thong aside to expose his sexy shaved balls, and began licking and sucking them into my mouth. He moaned in pleasure and spread his legs wider, giving me access to his balls. I licked and gently sucked them, and then I began to go lower. I licked the sensitive area under his balls, and then urged my tongue even further down. I've never been much for rimming, but he was fresh from the shower and his tight bottom beckoned me further. I pulled the thong aside as far as it would go with him seated, and licked the tight pucker of his anus. I licked for a few minutes, hearing him breath more deeply as I went, then I decided I wanted more. I asked him if he would like my tongue all the way in his bottom, and he turned around and got on his knees on the couch, presenting his taut buttocks to me and willing me to continue. I paused to take a pic, and then spread the thong and got a shot of his anus, now quivering with desire. I put the camera back down, pulled the thong aside, and went to work on my prize. He moaned as I penetrated his anus with my tongue, shoving it in as far as it would go, spreading his bottom with my hands so I had more room. Reaching down with my right hand, I felt his cock, rock hard and oozing, rubbing along the couch as he humped his ass back in my face. By that time, I wanted and needed to have my tongue inside him, and I pumped his bottom with my tongue like it was a cock, driving it into his anus and hearing him groan at the intrusion. His bottom gripped my tongue like a vise, but I drove it onward and rimmed him with all my energy. After a few furious minutes of tonguing him, I moved back down to his balls and gently began to kiss and suck them. He reached under his cock to help me, moving his balls all the way back to greet my lips. As I kissed them, I reached down to my own cock and felt an ocean of precome waiting there. Feeling bold and hot, I scooped some onto my finger, then rubbed it on his hole and resumed licking him there. That was a first, as I had never licked my own precome off another guy's bottom, and it was hot! I wanted to see what else I could do, so I moved my mouth back to his balls and began rubbing his hole with my thumb. This brought a slight moan, but no resistance, so I slowly began to penetrate his tight anus with my thumb. I pushed it in gently to the first knuckle, and he moaned a bit more. I licked and kissed his shaft and balls now, gently pumping my thumb in his hole, and his cock got even harder. For the next fifteen minutes, I kept up a round-robin, alternating between licking his bottom, balls, and shaft and fingering his hole with my thumb. I kept rubbing my own precome onto his hole, licking him and using it as lube to finger him, still amazed at how hot it was! I'm a bottom, but I think if I could have stood up and fucked him right there and then, he wouldn't have stopped me. Finally, my poor tongue was getting worn out, and I wanted to taste his orgasm. He turned back around and sat down, and I immediately engulfed his dick and began voraciously sucking him. He continued to moan as I told him I wanted his juice, and continued to shove my mouth up and down on his cock. This went on for another ten minutes, until finally I felt his legs quiver. "I'm gonna come!" he shouted, and at this, I gently slid my finger back up his tight bottom. He exploded at that point, thick sticky come pouring out of his cock, and I swallowed as fast as I could. It seemed like gallons, and as he relaxed, I slid my finger out of his bottom. His cock was wet with come, and I spent ten more minutes licking him clean and teasing his balls and shaft as I went. He needed to go, so we thanked each other and he got dressed and left. I took the thong and put it on, getting stiff when the wet material came tight against my own bottom, then sat down on the couch and began to masturbate. I pulled up the last picture, me licking his long shaft, and pumped my cock, thinking about how good it had been and how much I enjoyed rimming him and tasting my liquid on his bottom. I came hard, spurting my own ocean of semen, then cleaned up and got dressed. I sure hope I get to try his cock in my bottom soon, but something tells me he wouldn't mind being fucked either; should I ask him which one he wants more? Reader feedback is encouraged on this subject; let me know what you think I should do with him next time!