16 comments/ 110523 views/ 51 favorites The Part-Time Job By: centrum1000 It all started innocently enough. Martin Jackson replied to a help wanted ad in the back of the campus newspaper for a part-time data entry job. Martin, a freshman at Blue Mountain College, needed to find a job as part of his scholarship eligibility. He was awarded one of five academic scholarships that covered most of his tuition and living expenses, the only two criteria for keeping the scholarship were grades and maintaining a part-time job. Martin had no problem with the initial phone interview for the job and scored an in person interview the next day. When he arrived at the address the next day he cursed himself for writing it down wrong because he found himself in a quiet suburban neighborhood. He decided to give it a shot since he was already there and walked past the white picket fence to the front door. A chipper woman led him into the house, assuring him that he was in the right place after all. He took a seat in the living room with three other candidates and waited his turn. The job was for light secretarial work and data entry for a growing sales company. Martin was told that the woman who answered the door was the owner and the office was in her basement. She apologized for the fact that the job was based out of her home, but she assured him that the company had grown much faster than she anticipated and she would eventually rent a more traditional office downtown. He nailed the interview and with one other candidate, a fellow student named Joshua, got the job. The two of them would alternate days taking care of whatever was asked of them. Martin was told to show up on Monday morning after class and be ready to work. Jessica Stansfield was the owner, and only employee, of the company that she had built from scratch. She was a wholesaler of clothes and fashion accessories to local retail stores and boutiques. Not having any kids and being a housewife led to extreme boredom and borderline depression. Her husband didn't know what to do to help her so he encouraged her to get a job to give her something to do. She didn't like the idea of working for someone else and came up with the idea for her company, Stansfield Fashion Inc., one night while struggling to get to sleep. It wasn't easy for her, but over the past two years she managed to get the new business off the ground. While orders weren't quite flying in she was generating enough revenue to finally bring on a little help and the nearby college seemed like a perfect source of cheap labor. Her goal was for the new hires to help her clean up and merge various mailing/contact lists and answer the phone for her while she was out making sales calls. The additional help would allow her to be in two places at once and she hoped would give her a little breathing room. Martin, a typical eighteen year old college student, wasn't interested in getting a job but the school made it very clear to him what his choices were. His family couldn't afford to pay for college so he needed to keep the scholarship. He figured that the hours for this job would allow him plenty of time to study and give him a little extra beer money for the weekends too. When he arrived at Jessica's house for his first day of work he was struck by how hard working she was. She was constantly running around the basement office between her emails and phone answering questions and trying to close a big order. Jessica, in her mid thirties, had been married to her husband Eric for nearly ten years. She has shoulder length light brown hair and an athletic build. Her figure has slight curves and a small chest well suited for her 5'3" frame. She had thrown herself headfirst into her new company and focused all of her energy into it. She was grateful that her husband made enough money that he could support her new dream and wanted to see it succeed. On the first day Martin was shown around the house and given his instructions. The job would require him to spend most of his time at the computer in the basement office. He knew that he would have no problem doing the data entry work and was told that he could relax in the TV room next to the office after finishing. He had to make sure that he answered the phone by the third ring though. Jessica spent most of her time out on the road and told Martin to make himself comfortable. Martin spent the first week getting used to the new job and rearranging his schedule around it. During the second week he found himself getting bored after a few hours of the monotonous data work and decided to watch some TV. Not being much of a fan of daytime TV he started poking around the basement and stumbled onto a small laundry room. Jessica must have been in the middle of doing her laundry because the room was filled with baskets of clean and dirty clothes in separate piles. Martin had always liked girls, but ever since he was a young boy he also liked wearing women's underwear. Growing up with three sisters meant that there was always an ample supply of panties in the house. It started one summer day when two of his sisters decided that they wanted to play dress up. Using Martin as their doll they dressed him in one of their summer dresses and high heels and of course a bra and panties. He was too young to think that this was unusual behavior and didn't associate wearing his sister's clothes with anything sexual but he realized immediately that he liked the way it felt. After spending the next few days unsuccessfully hinting that he wanted to play the game again he decided to take matters into his own hands. Martin waited until he was home alone and snuck into one of his sisters' room. He spent the entire afternoon trying on everything that she owned. Over time he would steal panties from them and wear them under his clothes. He never got caught, but eventually he discovered sports and girls and he stopped wearing his sisters' underwear. Standing in Jessica's laundry room he noticed a large pile of her underwear and the old feeling came rushing back. It had been years since he even considered wearing women's underwear and he was too nervous to risk losing his job so he took a moment to look around the room before closing the door and getting back to work. He spent the rest of the day trying to push those thoughts out of his head and hurried home after his shift was over. Martin lived in campus housing but lucked out in the lottery. Not only did he end up in a two bedroom suite that was usually meant for upper classmen his roommate was kicked out of school in the first week. He never got another roommate so he ended up with a huge suite all to himself. He spent the entire walk back to his apartment keenly aware of his bulky boxer shorts underneath his pants. He tried to convince himself that it wouldn't be worth it but he knew deep down inside that he was going to have to try on Jessica's panties as soon as he could. He didn't work for several days after that and when he again showed up Jessica said that she was going to be out all day again. From the basement he noticed that he could hear her opening and closing the car door through the small window in the corner of the room and realized that the driveway was right next to the window. He climbed on top of a chair and managed to open the window a little, thinking that it would serve as a perfect warning alarm. He peeked into the laundry room and found a smaller pile of underwear waiting to be washed. Martin took his time examining every pair of her panties before choosing his favorite. He picked out a pair of loose fitting dark red satin panties and slipped it on. His body tingled as he pulled the soft material up his legs and over his cock. He tucked his penis down into the crotch of the panties and walked around the laundry room enjoying the feeling of the silky material against his skin. He tucked his boxers into his bag and put his pants back on so that he could get back to work. It was a quiet day on the phone and he managed to plow through the rest of the work with plenty of time left over. To wait out the rest of his shift he sat down on the couch in the other room and watched TV. Every time he moved he felt the soft material caressing him. He felt a little guilty about what he was doing, but he knew that Jessica would never know. His warning system worked as he had hoped and he was able to easily hear her car pulling into the driveway, giving him more than enough time to replace her panties and take his position back on the couch. For the next several weeks Martin fell into a routine and as soon as Jessica left the house he would pick out a pair of her underwear and wear them under his clothes while he worked. Eventually he became bold enough to even wear a pair of her panties home returning them the next time he worked. He thought that he had worked out a perfect system until Jessica confronted him. "Martin, we need to talk." He wasn't the smartest guy around, but he knew enough to know that nothing good started like that. "Yes Jessica." "I know what you've been doing while I'm away Martin." He felt his heart drop in his chest. "I want you to tell me why you've been doing this." "Uhhh...." "Come on, out with it. I can fire you right now if you would rather." He knew that he couldn't afford to be fired so he struggled to speak. "Well... you see..." "How long have you been a crossdresser?" Shocked by her bluntness, he froze. He never thought of himself in those terms. He just liked the way that women's panties felt. "I.. I.. I'm not a crossdresser." "Well then, what would you call it? You do wear women's clothes don't you?" Martin nodded in response. "Well whatever you call it, we should talk about it." Jessica found out in high school that her younger brother was a crossdresser when she caught him in her closet one afternoon. She knew how hard it had been for him and she did everything that she could to help him feel more comfortable. Looking at Martin, she saw the same fear that she saw in her brother years ago. She first became suspicious when she was looking for a pair of her panties in the laundry room, only to have it reappear several days later. She did an experiment and monitored her panties until she realized that the disappearing and reappearing coincided with Martin's schedule. "I don't know." he said with a trembling voice. "Listen, I know it isn't easy. My brother is a crossdresser too. How about this; whenever you're here you can wear anything of mine that you want. Ok?" He didn't know what to say. "Martin, I remember how difficult it was for my brother and I want to help you anyway that I can. My closet is yours, but don't stain anything ok?" "Uhhh... ok." "Are you wearing my panties right now?" He nodded again. "Let me see" Martin nervously unbuttoned his pants and let them drop to the ground. Jessica recognized the green lace panties that he was wearing. Martin was utterly humiliated. Nobody else had ever known his secret, and he had hoped to keep it that way. "They look good on you. Ok, now pull your pants up and follow me." He did as he was instructed and followed Jessica upstairs to her bedroom. She gave him a tour of the room, walking him though all of her clothes. "Here are all of my panties and bras. And over here are my slips and nighties. This drawer has my stockings, pantyhose, and socks." She then led him into her huge walk-in closet. "On this side are my suits and dress clothes, but I'm sure you're more interested in my dresses and skirts over here. In the corner is where I keep my lingerie and my shoes are in these drawers. Remember; feel free to wear anything you want as long as you do your job. Deal?" A million thoughts raced through his head as he heard himself say "deal". "Ok, I'm already running late so I've got to go. Please be sure to put things back where you found them and have fun Martin." She turned on her heels and rushed out to her next appointment. Martin stood in her closet for several seconds absorbing the magnitude of what just happened. Not only did he get caught wearing his boss's panties and she didn't mind but she actually gave him permission to wear her clothes. As soon as he heard her car pull out he tossed his clothes to the floor and perused her wardrobe wearing nothing but her green lace panties. He spent an hour going through her outfits until he came across a black silk nightie with matching panties. When he was younger, he never got a sexual thrill from dressing up but this time was different. he felt a tingle in his cock as soon as he put on her lingerie. He couldn't bear to be seen by her in one of her outfits so he put it on and put his other clothes back on over it. He went back to the basement and tried to make up for lost time. Jessica returned home before his shift was over and seemed surprised when she saw him. "I thought you would be wearing something different." "Uhh..." "Didn't you find anything that you liked?" She sounded almost insulted. "No. I mean you have a lot of nice clothes but.." "But?" She cut him off. "I don't know..." "Martin, you don't have to be uncomfortable around me. Ok?" "Ok." "How about this, let's just start slow and if you ever feel like wearing one of my dresses you can. Sound good?" "Sounds good." Martin left for the night and as soon as he returned to his apartment he torn off his clothes and frantically jerked himself off while still wearing Jessica's silk nightie and panties. The next several workdays passed by with the same routine of him picking something silky to wear and jerking off as soon as he got home. After a few days her found himself rubbing his penis through his panties so that he could feel the silky material rubbing against him. After rubbing himself for a little while he was getting uncomfortable in his pants and decided that he wanted to wear something a little less restrictive. He took a break and went up to Jessica's closet and picked out a pleated skirt instead. he finished the rest of his shift wearing the skirt over her panties and a nightie ticked into the waistband. Occasionally he caught himself involuntarily rubbing his cock through the panties and was enjoying the freedom of his new outfit. Over the next week he continued to wear more of her clothes without being seen by her. One day, however, she did come home earlier than he expected and walked in on him wearing a loose fitting brightly colored summer dress. She was overjoyed that he was branching out and felt like he was finally getting more comfortable. She told him how pretty he looked before letting him change to go home. The compliment didn't exactly make him happy, what self respecting straight man wants to hear that he looks pretty, but for some reason he felt himself blushing a little. While Martin continued to work his way through Jessica's wardrobe over the next several weeks he noticed that she was around much less often. Jessica had suspected that her husband was cheating on her and had even heard from several of her friends that they had seen him around town with different women. One thing that she couldn't tolerate was a cheating husband so she got herself a lawyer. He told her that her best bet in a divorce would be to have solid evidence otherwise it was a he said she said thing and that could get ugly. She knew that her friends wouldn't lie to her, but that didn't count as solid evidence. He also told her that some women would set their husbands up so that they could catch them in the act and suggested that one of her friends might be willing to help her out. She wracked her brain but all of her friends were married and knew her husband too well for that ploy to work. On the way home from her lawyer's office another idea popped in her head but she knew that it would require some work. Jessica arrived home to find Martin wearing a purple jersey dress while typing away at the computer. "Hi Martin." He stopped typing and turned to her. "Hi Jessica." "It's getting late, why don't you call it quits for the day." "Well, I was just finishing up this last entry." "Finish that one and then come up to my room before you go ok?" "Ok" Five minutes later Martin met her in her bedroom. "You have good taste Martin. Purple looks good on you." "Thanks." He didn't want to admit it, but it was one of his favorite colors. "Come over here." He walked over to Jessica who was standing by her closet. She held out a pair of high heels and pantyhose for him. "Every time I wear that dress I wear these heels and I find that the pantyhose ties it all in together. Have you ever worn pantyhose before?" "No." "Ok, let me show you how." She took another pair from the drawer and walked him through putting them on while demonstrating on herself. Martin was shocked that she felt so comfortable lifting her dress up in front of him. He even caught a glimpse of her bright yellow panties. He followed her lead and then slipped his feet into her heels. His feet were a little bigger than hers so it was a little uncomfortable but he managed to squeeze in. "How about heels? Have you had any experience with them?" "No." "It's ok. Just stand up for now. They take a while to get used to. You should start wearing them around the house from now on." "Ok." He said as he wobbled in her heels. She walked over to him and ran her hand across his thigh. "This won't do. You should also start shaving your body. You will feel much more feminine, trust me." He never thought about shaving himself before but felt like he was under a spell. "Ok, I'll shave my legs." "No, I mean your whole body. And then use skin lotion to make your skin feel nice and soft." Jessica lifted up the bottom of his dress and pulled back the pantyhose so that she could see which panties he wore. "Hold on." She said as she let go of the dress and turned to her drawers. She came around his back and pushed the dress off his shoulders before helping him into the bra that matched his panties and took a minute to show him how to put it on himself. "Now you look much more put together. Doesn't that feel good?" Martin couldn't deny that he felt incredible. He loved the way that the air felt as it slid across his legs covered in pantyhose. The bra wrapped tightly around his chest made him feel more womanly than ever before and the heels, while awkward, completed the outfit. He was grateful for everything that she was doing for him and had developed quite an affectionate bond with her over the past weeks. "Thank you Jessica." "You should take this outfit home with you and practice wearing everything. Remember I want you to shave every inch of your body before you come back." "Ok, I'll see you on Wednesday" Martin quickly changed into his clothes and raced home. He spent the night practicing walking around in the high heels and ended up jerking off in her dress twice before finally going to bed. He couldn't wait for his next day on the job. He showed up shaved and ready to go, but was disappointed that Jessica was already out on the road. He didn't hesitate to pick out another dress and made sure to wear the works. He picked out a matching set of bra and panties, pantyhose, and heels before getting to work. After a few hours Jessica called to check in on him. "Hi Martin." "Hi Jessica." "How's everything going today?" "Not bad, the phone has been ringing off the hook." "Good, maybe we can get some new business. Did you do what I asked you to?" "Yes, I'm all shaved." "How does it feel?" "It feels much better." "I told you. You should listen to me more." "Anything you say." "Anything?" She said coyly. "Sure." He shot off without thinking about it. "Well, I did have something in mind." "What's that?" "Well, I figure that if you're going to be answering my phone dressed like a woman maybe you should answer the phone like a woman too." The Part-Time Job "What do you mean?" "Have you ever tried to talk like a woman?" "No." "Give it a try." "I don't know." "Come on. You said anything I want!" "Ok. How is this?" He increased the pitch of his voice but sounded too much like a falsetto. "I think you need to work on it. There is a list of names and numbers on the desk. I can never get past their secretaries, so why don't you call every name on the list and say that you would like to do survey about the environment. I can guarantee that none of them will talk to you, but at least you can practice your voice." "I won't get much else done if I do that." "It's ok, I think this will be a good thing for you. I guess we need a new name for you to use too. How about Marsha?" Martin liked it right away. "Sounds good." "Alright, good luck!" The phone went silent as Martin stared at the list in front of him. He spent the next several hours calling every number on the list. Jessica was right that none of them wanted to do the survey but eventually he was getting more comfortable talking like a girl. Before going home for the night he went into her closet again and picked out a pink silk nightgown to take home. Slowly he found that he was wearing Jessica's panties everyday and even wanted to sleep in her lingerie too. The next several days progressed with him doing his work in full attire while answering her phone as Marsha. He had gotten much more comfortable wearing heels around her house and his balance had become much better with practice. The next time that Jessica came home during his shift she had a big smile on her face and a bag in her hand. "Come upstairs with me Marsha, I've got something for you." In her bedroom, Jessica handed him a bag of makeup and a brown wig. "Let me help you get this on." She fidgeted with it for a few moments and then stuck a couple bobby pins in it to keep it in place before stepping back to examine her work. "Now let me show you how to do makeup." She sat him down at her vanity and proceeded to show him the finer points of makeup. She walked him though the eye shadow, blush and lipstick and even applied fake eyelashes. Martin was surprised to see the transformation before his eyes. With every second that passed he realized that he was less like Martin and more like Marsha. After the makeup, Jessica reached into the bag and pulled out another package. She pushed the straps of his dress off his shoulders, revealing his bra, and stuffed something into each cup. Martin looked down to find that he now had a pair of rubber breasts tucked into the bra. After putting the dress back in place he realized that he look much more like a woman than he ever expected. They both looked him over in her mirror before she showed him how to remove the makeup so that he could go home. The next day Jessica was there when he arrived and helped him with his makeup again before she left. He wore a tight black mini skirt and a silver sleeveless button down blouse. She gave him a pair of very sheer pantyhose and a pair of black high heels. He finished the outfit off with the wig and got to work. He was startled to hear the doorbell ring and decided not to answer it. Whoever it was kept ringing the bell and Martin's curiosity eventually got him to peer out of the basement window to see who it was. When he saw a delivery van he decided to answer the door thinking that it might be an important delivery. He didn't like the idea of someone else seeing him dressed like a woman but he knew that he had practiced the voice enough to be passable. He nervously opened the door and caught himself staring at the delivery man. He looked to be in his early thirties with short blond hair and covered in a sheen of sweat from the heat. He was wearing a short sleeve shirt that was unbuttoned enough to show off his tan chest and his shorts were both very short and very tight. He realized that he was staring, but didn't know why. He had never been interested in other guys before but he realized that he was now standing in broad daylight dressed from head to toe in women's clothes. He felt like it was only natural for him to respond that way to a handsome young man while he was dressed like a woman. What really surprised him was that he felt his cock slowly coming to life under his skirt. His hardening penis strained against his panties as he signed for the package. He wasn't sure, but he thought he caught the delivery man checking him out before he turned to walk away. The whole experience left Martin shaking. It took him several minutes before he could calm down enough to get back to work. After a little while the phone rang again. "Good Afternoon, this is Marsha. How many I help you?" "Very good Marsha." "Oh, hi Jessica." "I just wanted to call to let you know that a package should be coming today. If they won't leave it I will need you to sign for me. Ok?" "Don't worry, it already came." "Great. Was it the hot delivery guy again?" "Uh..." "You know, short blond hair, huge muscles. He always has his shirt open." "Yeah, that was him." "My god, if I wasn't a married woman..." Martin felt his heart racing just hearing Jessica gushing over the delivery guy. He didn't know why but his cock was responding too. He felt it growing between his legs. He felt ashamed. "Thanks for signing Marsha. You're a big help." "No problem." "I'll be home late tonight but can you come by on Saturday morning? I have something special for you." "Sure, what time?" "How about 10am?" "Ok, I'll be here." "Great, I'll see you tomorrow." Martin finished out the day with thoughts of the delivery guy racing through his confused head. When he got up to change his outfit he decided to walk home like he was. He figured that nobody would recognize him and he was surprised how excited he got being out in broad daylight. He stuffed his regular clothes into his bag and braved the long walk home. He didn't run into anyone he knew until he was walking into his apartment. "Excuse me." A familiar voice spoke up from behind him. Martin turned around startled and just smiled. His heart pounded in his chest when he saw his neighbor Alex. He knew we would get caught for sure. "Hi, I'm Alex. I haven't seen you around before." "Uh.. I'm Marsha" He nervously blurted out. "I didn't know that the dorms were co-ed now." He joked. "Oh, I'm Martin's cousin. I'm staying with him for a little while." "I see. Well it's nice to meet you Marsha. This place could use a few more pretty faces like yours." Martin's nervousness melted away with the compliment. "There's a party on Saturday, would you like to come?" "Like a date?" "Yeah, like a date." He said smiling. "I don't know if I can on Saturday." "How about this, I'll give you the address and if you can make it I'll see you there." "Ok." Alex handed her a piece of paper with the address on it. "I hope to see you there." Alex turned and walked down to his room while Martin stood overwhelmed by the interaction. After Alex was in his room he was finally able to breathe again and entered his apartment. He practically ran to his bedroom and hiked up his skirt revealing the large bulge in his panties. The excitement from the day, not only passing as a woman but as an attractive one twice, had his juices flowing. He reaching into his panties and found that he had already left a wet spot. He pulled his cock out with his mini skirt hiked around his waist and jerked himself off in an instant. Saturday couldn't come fast enough for Martin. He spent all of Friday night thinking about what the surprise was. Martin showed up at Jessica's house bright and early ready for whatever she had in store for him. Jessica led him up to her room where she spent the next hour getting him dressed for his surprise. She picked out a bright yellow summer dress that hugged his torso and flowed off of his hips. She matched it with a pair of matching green silk bra and panties with a pink floral design and a pair of red high heels. She applied a thick layer of light pink lipstick and took her time on her face, making sure that it was perfect. For the first time Jessica didn't give her pantyhose with the outfit. When she was finished she said that it was time to go. "Where are we going?" "It's a surprise. Do you think you're up to going out in public like that?" "Well..." "Out with it." "I did walk home like this last night." "Very good Marsha. You're very brave woman!" She said excitedly. On the car ride he told her about running in to Alex and about their conversation. Pulling into the mall Jessica said "I think that it's about time we got you some of your own clothes. Maybe something special for you to wear to the party." "Who said I was going to the party?" "You said he asked you out right?" "Yeah, so." "Well, is he good looking?" Martin felt a little uncomfortable being on the spot but he was honest. "I guess so." "Do you have anything else to do tonight?" "No." "Well, it sounds to me like you should go out with Alex then." "I can't even afford to go shopping." "Don't worry, it's my treat!" Jessica led Martin to a teen shop first. After Jessica talked to the salesgirl they led Martin to a chair where before he knew it he felt a sharp pain through his ears as the woman pierced him. He looked up to find two small fake diamonds pinned to his ears. "Next stop, shoes! It's time we got you some that actually fit." Walking into the shoe store Jessica told the young salesman that her friend Marsha needed some new shoes but first she needed her feet measured. He led her to a chair and pulled up a stool between her legs. Jessica went off on her own to find some shoes for her while he took her measurements. He lifted up Martin's right leg and with one hands wrapped around his calf he slipped his shoe off. This was the first time that Martin had ever been touched by another man like that and the intimate contact sent a shiver through his body. The saleman positioned his foot into a metal device and made a few adjustments while measuring his size. It took a little while for Martin to notice that with his legs spread apart and his one foot held up in the salesman's lap he was openly flashing him his panties. His initial reaction was embarrassment when he noticed that the salesman was looking up his dress but that quickly turned to excitement at the thought of this man getting turned on by what he saw. He felt his cock stirring and realized that he had to end the show before he really gave him an eyeful. Martin discreetly pushed his legs together as the salesman told him that he got the size and would be right back. When he returned Martin was more careful with his legs as the salesman slipped each of his feet into several pairs of shoes. The new size was much more comfortable than Jessica's, but more important to martin was the fact that the salesman was letting his hands linger on his calves as he helped him into each shoe. His cock almost ripped through the thin material of his panties as he felt the salesman's strong hand gently squeezing his leg. After he tried on a few pairs Jessica came over and said that they would take them all. Martin left the store wearing a pair of his news heels and a raging hardon between his legs as they headed to a salon to get their nails done. After the pampering she took him to buy scented lotions and perfumes. Their next stop was the department store where she bought him several dresses, skirts and tops. Their last stop was a lingerie store where she pulled out all the stops and bought him everything under the sun. After their shopping trip Jessica drove him back to his apartment and helped him get ready for his big date. She told him to shower and shave, making sure that he didn't miss a single hair. She instructed him to use his new scented lotion all over and then helped him pick out an outfit for the night. They picked a red halter top and a loose fitting black skirt that ended just below his ass. Jessica chose his new pair of black high heels and watched as he did his makeup, giving him tips along the way. Underneath the outfit, Martin wore a light red push-up bra and a pair of matching silk red thong panties. To finish off the outfit, Jessica surprised him with a pair of very realistic silicone breasts that she had purchased earlier. She had purchased several pairs in different colors and held each one up to his chest before settling on the closest match to his skin tone. She covered the flat side in a special adhesive that was meant to work on skin and had him hold them in place until it dried. Martin was amazed at how realistic the fake breasts appeared to be. Jessica did such a good job matching the skin color and applying the glue that he couldn't even see where the silicone ended and his skin began. The push-up bra combined with the new silicone breasts gave him a very attractive cleavage that was partially on display through the front opening of the halter top. After getting him ready for the party Jessica suggested that they go out for a drink beforehand. But before they left she asked if he could stop by her house again the next day. She told him to wear the outfit that she had already set aside for him in his bedroom. He didn't hesitate to say yes. The two of them went to a campus bar, and even though he was only eighteen, he had no problem being served as Marsha. Jessica ordered for them and several martinis later she suggested that she drop him off for the party. "I would love to stay and watch, but I would stick out like a sore thumb." "Thanks for everything today Jessica. It was too much." "It was nothing. Don't forget tomorrow. I need your help with a very special project." "Ok, I'll be there." "And be careful tonight, college boys only have one thing one their mind!" It wasn't until he heard Jessica's car driving off that the full impact of what was happening set in. The drinks had gone right to his head and it slowly dawned on him that he was standing outside of a frat house dressed to kill and ready for a hot date. He debated turning around and going home, but the excitement and alcohol clouded his better judgment. Walking into the party he immediately felt people looking at him. It took a little while for him to realize that guys were looking at him not because they suspected that he wasn't really a girl but because he looked good and that's when he ran into Alex. "Hey beautiful!" Alex swooped in and gave Martin a big hug drinking in his perfume. "You smell delicious." He whispered into his ear. "Hi Alex." "I'm glad you came out tonight. Let's go get a drink." Martin followed him to the bar where Alex ordered several shots for them. It was a sweet shot that went down easily and helped him loosen up a little more. "Do you want to dance?" "Sure." Alex led him into the middle of a crowd of dancing bodies and they danced to a fast song. After several songs, Martin was beginning to feel more comfortable and started to lose himself to the music and the combination of the darkened room and the anonymity of the crowded dance floor. Lost in his own thoughts Martin felt Alex's hands on his hips. "You're look good moving around like that. You have a very sexy body." Alex tilted his head into Martin's neck to compliment him letting his lips gently brush against Martin's skin. "Thanks." At first, Martin was surprised by the sudden contact but then was even more surprised by his reaction to it. He felt his cock slowly responding to Alex's touch by growing in his silk panties. Alex's hands remained on Martin's hips while they danced but before long they had moved around to his ass. He felt Alex's finger tips resting against his upper thighs just below the hem of his skirt while the palms of his hands gently massaged his ass through his skirt. Alex pulled Martin closer and leaned in to kiss him. Martin felt a rush of excitement course through his body as Alex's lips pressed against his. He felt Alex's crotch pressing against his through the thin fabric of his skirt as he tasted another man's lips for the first time. Martin had kissed plenty of girls before and he always loved how sweet their lips tasted but Alex was different. With the roles reversed on him he felt his body melt into Alex's hands. As they kissed Alex moved his hands under Martin's skirt and explored the soft skin of his bare ass occasionally rubbing his fingers along the edge of the silk thong tucked between his cheeks. A low moan escaped Martin's lips as his date felt him up on the dance floor, parting his lips enough for Alex's tongue to enter his mouth. His body shuddered at the forceful entry of Alex's tongue. Instinctively Martin raised his hands up and locked them around Alex's neck while allowing his date to have his way with him. After a long kiss Alex moved his mouth away from Martin's and kissed a trail down his neck into his cleavage before pushing his lips to Martin's ear and whispering "Let's go upstairs." Alex led Martin through the crowd and up to an empty bedroom on the second floor. He didn't bother turning on the lights as he lifted Martin up and tossed him onto the bed. Martin lay on the bed waiting for his date until he felt the bed move as Alex crawled on top of him. Alex worked his way up Martin's body, slowly kissing up his calf and then his thigh until Martin realized that he had to react before Alex found out his secret. Martin pushed Alex off of him and onto his side and then worked his way over to him so that their bodies were pressed against each other. Martin finally realized that Alex was naked when he felt the heat of his rock hard cock pressed against his bare thigh. Alex's lips found Martin's and they continued where they left off downstairs, but this time Martin took the initiative and explored Alex's body. He ran his hands across Alex's hard chest and back memorizing every curve and contour in the dark. His hand moved down the front of Alex's body until he found himself holding onto another man's penis for the first time. He had played with his own cock enough times that his fingers naturally wrapped around Alex's cock but he was amazed at how hot his skin felt in his hand. Martin's fingers ran up and down the length of Alex's cock as he took in how soft it was on the outside while at the same time being as hard as steel. He played with the tip and then followed his thick vein down the side until he grasped the base of his date's cock in his hand. Alex's kissing had become more passionate as he played with his cock and he had begun to massage one of his fake breasts through his halter top. Feeling all of his inhibitions disappearing he started stroking Alex's cock. After a few strokes Alex rolled onto his back to give Martin a better angle and grunted his approval while Martin jerked him off. Martin's paced quickened until he felt Alex's cock expanding in his hand as he shot ribbons of cum across his bare chest. Martin kept stroking as Alex came, using the slick liquid as a lubricant he stroked his hand from the tip down to the base of his cock. He kept stroking Alex until he felt his cock shrinking in his hand and then he stopped. Alex panted next to him while Martin still held his soft cock. Remembering the last blowjob that his ex-girlfriend gave him, Martin slid down on the bed and positioned himself between Alex's legs. He took his soft cock in his hand and guided it to his mouth as he lowered himself down. Martin was put off by the taste of Alex's cum at first but soon found that he liked the musky flavor as he licked him clean. He ran his tongue all over Alex's cock and pulled his flaccid penis into his mouth while he swallowed his juice. "Oh baby." Alex moaned with Martin's lips wrapped around his cock. The Part-Time Job Martin kept licking and sucking until he felt Alex's cock slowly filling his throat with his now erect cock. Martin repositioned his head and managed to take most of him into his mouth without gagging. With each thrust of his mouth he found that he was able to take more and more of Alex's cock inside of him. By now his own rock hard cock was straining against his silk panties begging to be freed. Martin wrapped his right hand around Alex's balls while his left hand, which was still covered in Alex's cum, pushed his panties to the side and released his own raging hard on. His cock was quickly coated in Alex's cum as he pumped away at his own meat while sucking Alex's cock at the same time. He couldn't take it for very long and blasted his cum into a puddle on the floor. He tucked himself back into his panties and focused all of his attention on the cock in his mouth. He didn't know if Alex would be able to cum again so quickly but he was determined to try. His hands rubbed Alex's thighs and balls as he took him fully into his mouth. "That's it. Don't stop Marsha." Martin worked his mouth up and down as fast as he could until he felt a hot liquid against the back of his throat as Alex unloaded his cock into him. He swallowed as much as he could and felt two more shots of his sticky cum enter him before he had to pull his mouth away just to breathe. Martin pushed himself back and remained on the floor at the foot of the bed while he swallowed Alex's cum and caught his breath. "That was incredible Marsha. I've never had such a good blow job before." "I'm glad you liked it." He had never anticipated that he would find himself in a dark frat house bedroom with cum dripping down his face but he couldn't deny that he enjoyed his new persona. Martin looked up and saw how late it was and decided that he needed to get home. He told Alex that he had to work the next day gave him another kiss and then left. On his way home Martin felt like a real woman and enjoyed the cool night air blowing between his legs and across his cum soaked panties. Back at his apartment he finally saw the outfit that Jessica had picked out for him and wondered what her special project was. The next day he showed up at Jessica's house wearing a short floral chiffon skirt with a thin purple satin tank top that draped loosely across his new breasts. He also wore a pair of bright red high heels and a pink lace bra and matching panties. Jessica answered the door wearing a pair of spandex pants and a loose t-shirt, apparently she wasn't planning on making any client calls. "I'm glad you're here. Come on in." Jessica led Martin into the living room and sat down on the sofa. "I don't know how to say this..." She seemed nervous and upset as she spoke. "What's wrong?" "I know my husband is cheating on me." "What?" "I've suspected it for a long time, but two of my girlfriends saw him in town with someone else." "What are you going to do?" "I'm going to divorce him but first I need your help." "You know I'll do anything for you but I don't know how I can help you." "My lawyer told me that in order for me to make sure that he doesn't get half of my business in the divorce I need proof that he's cheating on me. He suggested that I try to use one of my friends as bait to set him up, but he knows all of my friends. You're the only person I can think of that I can trust." "You want to use me as bait?" "All I need to do is get a picture of you two kissing. He comes home early on Sunday's and if he drives you home I know he'll make a move. I'll follow behind you with my camera and get the evidence." Martin thought it over nervously. He didn't like the idea of setting up her husband but he owed her for everything that she had done for him. "What makes you think it will even work?" "How did your date go last night?" The question made Martin blush as he pictured himself on his knees with Alex's cock in his mouth. "Marsha, you look beautiful. Any guy would kill for a shot at you, especially a horny bastard like my husband. I know it will work." "You've done so much for me, how can I say no?" "Is that a yes?" Martin nodded. "I'll help you." Jessica spent the next ten minutes on the phone with her husband telling him that she had to go out but her employee Marsha would need a ride later. After everything was all set she left and promised to stay close behind for the ride home. Martin spent the rest of the day working in the basement until Jessica's husband Eric came home. He walked into the office to find Marsha typing away at the computer. "Marsha?" He asked as he pushed the office door open. Martin turned around in the chair. "Yes?" "Hi, I'm Jessica's husband Eric." He walked over to Martin and took his hand. Martin stood up extending his hand into Eric's. They stood silently for a few seconds holding hands while Eric took in the sight of the hot young co-ed before him. "Jessica said that you were pretty, but I had no idea. You really are a beautiful little thing Marsha." Martin blushed at the compliment and stood frozen like a deer caught in headlights. Releasing Martin's hand, Eric stepped forward and lifted Martin's chin with his fingers while leaning into him. "You smell nice too." "Thank you" Martin nervously retorted. His heart pounded in his chest as he realized that he was being seduced by an older married man. "Can I kiss you?" Martin nodded and waited. Eric moved in and slowly pressed his lips to Martin's. He wrapped his arm around Martin's waist and pulled him closer. Martin's cock was ready to explode in his panties. After a few seconds he broke away and whispered. "You taste like peaches... Let's get you home." Martin was a little disappointed that the moment was over, but he knew he had a job to do. He followed Eric out to his car, a vintage Cadillac with bench seating, and they took off. Eric parked down the street from Martin's building and killed the engine. Without missing a beat he had his hand on Martin's bare knee and was caressing him. "Your skin is very soft Marsha." Eric adjusted himself in the seat so that he was facing Martin. "Does this make you uncomfortable?" Eric asked as his hand slid up Martin's thigh. Martin knew that he had to play along, but at the same time he couldn't help but enjoy having Eric's hand rubbing him. His cock strained against the thin material of his panties. "No." He whimpered. With one hand still on Martin's thigh, Eric reached for Martin's breast and kneaded his silicone flesh through the satin tank top. Eric's hands slowly rubbed Martin's body while his body slid down in the seat. Martin closed his eyes letting his legs spread apart while the older man fondled him in broad daylight. Martin snapped out of it when he felt the backside of Eric's hand brush against his hard cock as he worked up his thigh. He knew he needed to act quickly. Martin turned his body towards Eric and lifted himself up until he was straddling the older man. His head fell forward and he planted his lips onto Eric's. They kissed while Eric's hands explored every inch of Martin's quivering body. Martin was so horny he began grinding his hard cock into Eric's crotch. After several minutes of making out Martin felt Eric's hands between his legs and then felt Eric's hard cock spring free slaping him against his own panty covered cock. After a few moments of shifting around Martin realized that Eric had put a condom on and instantly got nervous that he couldn't possibly get out of this without him finding out. Martin kept his tongue buried in Eric's mouth while he reached between his legs and grabbed Eric's penis. First he stroked it for a moment and then he guided the tip between his legs. With his other hand he pushed his panties out of the way and then pressed the tip of Eric's cock against his virgin asshole. Grateful that the condom was lubricated he pushed down until he felt the tip penetrate him. Martin let out a gasp as Eric's cock entered him. The initial penetration surprised him because of how big Eric's cock felt as it pushed into him but the feeling of pain quickly faded into pleasure as he felt Eric's hard cock splitting him in half. Martin's head fell back as Eric's hard cock filled him inch by inch until her was fully inside of him. He paused briefly before grinding his hips into Eric's lap so that he could feel him moving inside of his ass. Eric didn't waste any time and was already thrusting up into Martin's asshole encouraging him to fuck him back. Martin pushed up with his knees until only the tip of his cock remained inside of him and then dropped back down onto him. Martin developed a good rhythm while awkwardly fucking Eric the front seat of his car while Jessica slowly cruised past snapping pictures of the two of them. Every time that Martin lowered himself into Eric's lap his own panty covered cock pushed into Eric's stomach bringing him closer to the edge until he felt himself explode. Martin grabbed onto Eric's shoulders and slammed his body down pushing Eric's penis deep inside of him as his cock erupted in his panties. He continued to grind himself into Eric while his own cum dripped down from his panties and covered Eric's crotch. After he finished cumming he resumed riding the older man's cock until he felt it expanding deep inside of him. He knew Eric was cumming and slowed his pace while he came. After Eric's cock finished unloading itself Marin could feel him growing limp inside of him. He leaned into Eric for another kiss and pulled on the handle of the car door to make his exit. "Thanks for the ride." He whispered into Eric's ear before pulling himself up and closing the car door behind him. Martin practically ran up to his apartment, his head spinning from thinking about the fact that he just fucked another man who thought he was really Marsha. In the hallway of his building Martin ran into Alex who looked like he had been through hell. He was apparently just coming home from the party the night before and appeared to still be very hung over. "Hi Marsha." "Hi Alex, thanks for bringing me out to the party last night. I had a good time." "So did I. I hope we can get together again sometime soon." Still feeling incredibly horny from the encounter with Eric in the car Martin walked up to Alex and pushed him against the wall before planting his mouth against Alex's. Martin aggressively kissed Alex while rubbing his cock through his pants. "Let's go inside." "Sure." Alex fumbled with the door and led Martin into his apartment. Once inside, Martin dragged Alex to his bedroom and pulled off his pants and shirt before pushing him back onto the bed. Martin climbed up and straddled Alex until they were chest to chest. While distracting Alex with his mouth, Martin used his hand to collect his cum from his panties and used it to lubricate Alex's now rock hard cock which was already sliding between his thighs. Once covered in his cum Martin guided Alex's cock to his already stretched out asshole and pushed back against him. "Ohhhhh" Martin moaned as Alex's plunged deep into his ass. Alex was still in a fog from the night before and barely reacted to what Martin was doing to him. Martin bounced up and down on Alex's cock as fast as he could enjoying the sensation of driving Alex's hard cock inside of him with every thrust. "Fill me up Alex. Don't stop fucking me." Martin yelled as he rode the half awake Alex. Martin reached around and played with Alex's balls while he rode him. Seconds after he began rubbing Alex's balls he felt the first shot of cum escaping his cock filling him with Alex's hot sticky cream. Alex's cock kept shooting cum inside of Martin's ass until it was dripping down his leg into a puddle on the bed. After he finished cumming, Martin collapsed on top of him and stayed there with Alex's soft cock still buried inside of him. They remained like that silently for a while until Martin realized that Alex had fallen asleep. Martin lifted himself up, allowing Alex's cock to finally slip out of his asshole, and looked down at the naked man in front of him. His cock twitched in his panties and he knew he needed relief. Kneeling between Alex's legs, Martin released his cock from his panties causing the front of his skirt to tent out. He scooped up some of Alex's cum that had dripped out of him and collected on the sheet. He rubbed the warm cum onto his cock for lubrication and jerked himself off while Alex slept. He couldn't risk Alex waking up to the sight of him stroking his cock so he rubbed himself as fast as he could until he felt like he was about to cum. Just before he came, Martin leaned forward and rubbed his cock against Alex's taking both of there cocks in his hand. He stroked both of their slick cocks together until he lost control. Martin's cock erupted, shooting his cum all over Alex. The first blast of his hot sticky cum shot up and hit Alex on his face, followed by several more shots that landed on his chest. After emptying himself, Martin paused with both cocks still in his hand. He took in the sight of Alex's naked body covered in his cum before standing up and tucking his penis back into his panties and leaving for his own apartment. Later that day, Martin met up with Jessica who was thrilled with the pictures. She told him that her lawyer said that she had a slam dunk case thanks to Martin. She flipped through the photos, which started with them kissing and ended with his head leaning back and his mouth agape as her husband's cock first entered him. Martin told Jessica everything that happened at the party, in the car, and in Alex's apartment and she was thrilled that Martin was finally living the life that he always wanted.