Story Warnings: Whore!Matthew, cross dressing, partial gender change in later chapters, yaoi, language, sexual events. More may be added later depending where I take this story.

Chapter Warnings: Cross dressing, masturbation

Disclaimer: I don't own anything in this story but the idea.

Also, if anyone is interested I enjoy doing role plays over PM on this site. I am up for most pairings so feel free to PM me!

Chapter One: Panties

Matthew had always been a shy boy. So shy that he was barely noticed by adults and children alike. His parents barely noticed him even though he had no siblings and he had never made any friends since the children in his classes growing up had never taken notice of him. His only friend had been a stuffed polar bear that his parents had bought him when he was still a toddler and they had still noticed him every once in a while. Eventually they stopped noticing him as well and Matthew ended up living by himself in a small apartment near his high school. Luckily his employer noticed him enough to give him a pay check each week so that he could pay for rent, food, and other items such as clothing.

As Matthew had entered Middle School and then High School the few times he would get noticed was when someone mistook him for a girl. Matthew knew he had a feminine body and face but it was still a bit offending. Over time he grew to accept that he was feminine and maybe that was what brought him to the store he was currently standing in front of.

Said store was a lingerie store and Matthew had come here because over the last year he had become curious as to what women's clothing and undergarments would feel like. Would they fit him better because he looked feminine? Matthew wasn't sure, but he was determined to buy something.

Matthew was pretty sure he wouldn't get noticed while browsing but he would have to get noticed when he wanted to make a purchase. So he decided to make himself look like a young girl of about thirteen or fourteen. He was wearing a baggy red hoodie to try and make it seem like the reason he didn't have breasts was because his clothing was too baggy. He was slightly smaller than most boys his age – 17 years old – so he could pass for a slightly tall girl. Matthew had also brought his stuffed polar bear Kumajirou along to make himself seem more childlike.

Taking a huge breath, Matthew headed into the store. A small bell rang as the door was pushed open and then closed behind him. Matthew's eyes nervously glanced back and forth, watching the other people in the store, but no one seemed to notice him. Sighing in relief Matthew slowly wandered over to the display of panties that had a large SALE sign above it.

On the display table were multiple boxes of different types and sizes of panties. Lace panties and non-lace panties were spread out in sections labeled XS, S, M, L, and XL. There was also a small chart on the side of the table saying the waist sizes for each lettered size. A measuring tape that Matthew often saw seamstresses on TV wearing around their necks was there as well. Glancing around once more Matthew took the measuring tape and bunched up his hoodie a bit so he could measure his waist.

After getting his size he placed the measuring tape back down and checked his number on the chart. Seeing that he was a size S, Matthew started to look through the size S boxes. He had decided ahead of time to get seven pairs so that if he liked them a lot he wouldn't have to do laundry very often. The sale was quite cheap as well so even though he was buying seven pairs, if he didn't like them he wouldn't feel as if he wasted too much money.

Matthew looked closely at the different types of panties in the boxes and decided, with a small blush on his cheeks, that he wanted the lace panties instead of the non-lace ones. He took out three pink lace panties that had a small pink bow on the front as well as three of the same ones in black.

After a moment Matthew decided he would get a more adventurous type for his last pair and picked out a black thong. Matthew then made his way over to the counter, his face bright red. The lady at the cash register barely glanced at him as she rang up the seven pairs of panties and placed them in a small silver bag. He quietly thanked her before hurrying out of the store, clutching both the bag and his polar bear to his chest.

It took Matthew fifteen minutes to get home on foot and by then his face was crimson. Even though he was never noticed it still felt as if everyone he had passed was staring at him. As if they knew where he had been and what was in his bag.

Placing Kumajirou down on the couch in his small apartment Matthew made his way down the hall to the one bedroom. The bedroom, even though it should be the master, was the size of a small guest bedroom. It was able to fit his double bed, one bedside table, and his dresser. A small closet was on the wall to Matthew's left as he entered the bedroom and there was a window on the right wall. His bed and bedside table were against the wall across from the door and the dresser was beside the door.

Matthew almost always has the blinds to his bedroom window shut since it looked right into the bedroom of a very sexual couple in the apartment building beside his. Today the blinds were open and Matthew moved to close them before nervously taking off his pants and briefs. Letting out a shaky breath, Matthew pulled a random pair of panties out of the silver bag that he had placed on his bed. The pair pulled out was one of the pink lace panties. Slowly he placed his feet through the leg holes in the panties and pulled them up until they were half way up his thighs. Letting out another deep breath Matthew pulled the panties up the rest of the way, tucking his penis into the crotch area.

Once on Matthew noticed how tight the panties were on not just his crotch but also his ass, compared to the briefs he usually wore. It felt uncomfortable since he wasn't use to it, but Matthew was surprised at how much he liked it. The tightness felt good and Matthew blushed happily at this. Looking down he noticed that his penis made a large bulge in the panties since they were meant to be tight on women, let alone men.

After admiring them for another moment longer Matthew slipped his jeans back on over top. Glancing over at the small alarm clock on his bedside table he noticed that he needed to leave for his job at the bookstore. He quickly rushed out of his room and back to the front door. After slipping on his shoes Matthew rushed out of the apartment, quickly locking the door behind himself.

0o0

Work had gone fairly well for Matthew. He had been a bit scared that his jeans may go down a bit when he bent over to grab a book or something, but since no one noticed him no one noticed that he was wearing panties if they had shown.

Matthew had enjoyed the feeling of the panties against his penis and ass as he moved around. They rubbed sensually against his skin and Matthew had been a bit worried that he would get hard but he luckily hadn't. He was sure the panties would become painfully tight if he did get hard.

After five hours of work Matthew headed back home to his apartment. It was seven fifteen by then so Matthew decided to make himself a quick dinner before working on the last of his homework that was due for school tomorrow.

By ten PM Matthew was lounging on his bed in just his panties while finishing the last page of Romeo and Juliet for his English class. Smiling to himself Matthew closed the book and placed it on his bedside table. He had already brushed his teeth so he clicked off the lamp that was also sitting on his bedside table before rolling over onto his stomach.

A soft thump was heard and Matthew realized that he had knocked Kumajirou off the bed. Frowning slightly Matthew started to move on his stomach towards the edge of the bed when he felt his crotch rub against the bed through the panties. It sent blood rushing to his penis and made Matthew let out a quiet moan.

Forgetting Kumajirou, Matthew started to move slowly back and forth against the bed on his stomach. He could feel his penis harden and grow in his panties, making them tighten painfully against his crotch. Surprisingly, Matthew enjoyed the pain and he started to hump his bed a bit more roughly. His erection continued to grow and become more painful as it tried to fit in the tight confines of his panties

Moaning with need Matthew decided it was too difficult to hump his bed. Grabbing his two pillows Matthew stacked them on top of each other before climbing on top of them. He put his knees on either side of the pillows and started to hump them at a fast pace. After a moment Matthew stopped again, disappointed that the pillows weren't hard enough to give him relief. He didn't want to just stroke his erection because he wanted to feel the fabric of the panties rubbing against his erection so he decided he needed something else to hump.

Matthew gets off his bed and leaves his bedroom. He heads into the living room and is glad that the blinds are closed on all of the windows. He usually did that because he didn't feel comfortable having people stare into his apartment.

He looks around the living room before his eyes rest on the arm of the couch. It was rounded and had little padding since it was a cheap couch. Matthew walks over to the couch and straddles the arm. It was a bit awkward since he had one knee on the couch cushion and one foot on the ground, but he knew it would work the best.

Matthew glances down at the large bulge in his panties, seeing that his erection looked like it would pop out at any moment. Matthew just hoped humping the couch arm wouldn't wreck the panties. Oh well, he could always buy more if it did.

Matthew then started to hump the couch arm, slowly at first but soon the amazing pressure on his erection as well as the texture of the panties against it made him start to hump at a quicker pace as lust clouded his mind. Loud moans spewed from his mouth as he humped the couch arm as quickly as possible, grinding his erection down against it.

The pleasure continued to build and after only a few minutes Matthew came harder than he ever had. Gasping for air as he came down from his orgasm, Matthew glanced down at his panties. They were soaked in semen and some had even leaked out onto his thighs, couch arm, and he could feel some back near his ass.

Matthew's face goes bright red as he realizes that he just humped his couch. He quickly grabbed some paper towel from the kitchen and then used it to clean the semen off of the couch arm. Once he threw out the dirtied paper towel he realized how tired he was. Not even bothering to change out of his panties or clean himself in any way, Matthew curled up under the blanket on his bed and fell asleep.