The Part-Time Job

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."