tagTransgender & CrossdressersIt All Started Innocently Enough

It All Started Innocently Enough


It all started innocently enough for Marcus. He had been dating Christina for six months. They spent nearly every free moment together and missed each other whenever they were apart. At first Marcus was just happy having sex nearly every night. Over time though, he started to fall for her.

Christina was the type of girl that could easily be described as out of his league. She was far too pretty to be wasting her time with such an ordinary guy. Their relationship began as a one-night stand. She was drunk and horny and he was there. She went home with him, even though she never would have normally given him so much as the time of day. The next morning, she struggled to remember where she was. Disappointment quickly turned to surprise as he mounted her and proceeded to fuck her brains out before she could even remember who he was.

She had often gone home with random guys, but had never found someone who fucked her with such passion. She ended up spending the weekend with him, which eventually led to their relationship.

She was an incredibly horny girl and he was eager enough to do whatever she asked. As her request he became a pro at talking dirty. They even experimented with tying each other up. The true turning point for him though was when she encouraged him to try on a pair of her panties.

It was a pair of sexy red satin panties. He had never considered wearing women's underwear before but couldn't say no to her. Much to his surprise it got Christina really turned on. They fucked immediately, while he still wore the panties, and then she encouraged him to keep them on for the rest of the night.

He enjoyed the soft fabric against his skin, but more importantly he enjoyed the effect it had on his girlfriend.

One night, she came to his apartment with a bag from Victoria's Secret. It was filled with several pairs of panties just for him. Over time, Marcus would only rarely if ever wear boxers. Wearing sexy panties had become second nature to him by the time Christina dumped him. She had moved out of his life just as quickly as she had moved into it.

After she left him, Marcus buried the panties in the back of his underwear drawer. He had reverted back to his old wardrobe until one lonely night. He had come home from the bar alone and drunk. Sitting on his couch, watching a porno, he reminisced and decided to fish out a pair of panties. He stripped off his clothes and slipped on a yellow satin thong. His cock responded to the soft fabric. His mind flooded with memories of Christina and her naked body pressed against his.

Standing in the middle of his bedroom; Marcus' imagination took over. His hand began to rub his hard cock, encased in the thin panties. He pictured her in front of him while rubbing himself. It took mere seconds before his body tensed up and his cock filled the panties with cum. The sounds of moaning came from the living room.

He cleaned himself up and then put on a fresh pair of panties. Marcus spent the rest of the night wearing nothing but a silk thong. The next day he fell back into his old routine and wore panties under his clothes. He wore them under his suit to work that week and jerked off in them every night.

Nearly two weeks after he began wearing panties again, Marcus went to a happy hour with some co-workers. After two hours of beers mixed with some shots he decided to get home before he ended up staying out all night. Walking to his apartment from the subway, Marcus passed a Victoria's Secret store. Pausing in front of the store, he wondered if that was where Christina had bought his panties. The bright lights of the store called out to him and his piqued his curiosity.

Marcus gathered his nerve and tried to appear confident as he strode through the door.

"Hello. My name is Sara, how can I help you today?" A chipper young woman approached him as he entered.

"Uhh..." His words froze in his throat. He never expected to have to talk to anyone. He still wasn't sure why he was even there.

"Are you looking for something special?"

Marcus cleared his throat and mumbled that he was looking for something for his girlfriend.

"Panties, she loves panties." He continued, hoping that he wasn't being too transparent.

"I can help you with that. Follow me."

Sara led him to a corner of the store that was filled with every type of panty imaginable. With her help he decided on several pairs. She noticed that he had been drinking so she figured that he would be an easy up-sell. After picking out the panties she led him to a rack filled with lingerie. He seemed uneasy as she showed him the sexy outfits but she pressed on.

"This one is actually on special this week. It is our number one seller so it won't be here long."

She held up a purple chemise.

"Just feel it." She was trying her best to rope him in.

Marcus reached for the material and marveled at how soft it was.

"We normally sell this for $79.99 but this week only it is $49.99 and it comes as a set." She pointed to a matching silk robe and a g-string panty.

"Wouldn't you like to see your girlfriend in this?"

He nodded absently while still rubbing the material between his fingers.

"Should I wrap this up for you then?"

He couldn't make the sounds to say no.

"I... Uh... Sure."

A skilled saleswoman, Sara didn't hesitate. She took the panties in his other hand and the outfit and turned to walk towards the cash register.

"How about a few other accessories? I know she will love them."

"Umm.. Ok." He didn't know what he was agreeing to anymore but he couldn't stop himself. The drinks had gone to his head and the sensation of being in a lingerie store, buying panties for himself, was too overwhelming for him. He had lost all control.

Marcus followed Sara, who took the scenic route to the register. He watched her hands expertly plucking items from racks and bins as she led him to the back of the store. After fumbling with his wallet he fled the store as quickly as he could manage.

His heart was pounding in his chest until he was safely back in the sanctuary of his own apartment. He dropped the bag at the door and ran straight for the shower.

After drying himself off, Marcus gingerly walked into the front hallway. He hoped that it had all been his imagination but the bag was proof of what he had done.

It had been ok when he wore panties with his girlfriend. He even rationalized that it had been ok recently because he was lonely and thinking of her. But this? This was clearly different. What had gotten into him?

He took the bag into his bedroom and placed it on the floor. Sitting on the edge of his bed he slowly pulled the items out one-by-one and made a mental inventory. He recognized each of the panties that he had selected. Next he pulled out the purple chemise. He was again amazed at how soft it was. His cock began to stir as he draped the lingerie across his naked body.

After laying the chemise out on his bed, he continued his inventory. Next he pulled out the matching robe. The silky material danced across his flesh as he spread it out next to the chemise. The next item was the matching g-string. The front panel consisted of a small purple triangle with a thin silky black ribbon extending from each corner. They looked like stripper panties to him. His cock continued to respond.

He paused to look down at his new collection and without thinking about what he was doing he stepped into the purple panties. They could barely contain his hardening cock. The thin ribbon disappeared between his legs and slid between his ass cheeks. The sensation was new to him. He had several thongs but the material mostly stayed on the outside of his ass. He was embarrassed to admit to himself that he liked the feeling of the silky strip of fabric tucked between his cheeks and nestled against to his asshole.

Marcus felt the effects of alcohol wearing off and didn't want to get a headache so he decided to make himself another drink. He reached down and pulled the robe over his shoulders. His body shivered as it was encased in the soft silk material. He tied the sash in the front and went to the kitchen. The robe danced across his skin with every step.

Marcus poured himself a large, stiff vodka cranberry. He took a large swig before returning to his bedroom.

Still wearing the g-string and robe, he continued to sort through the bag. The next thing that he reached for was light and delicate and was wrapped in pink tissue paper. He laid it out on the bed and opened it up. He found a tangled mass of purple lace straps. He couldn't quite figure it out so he did his best to untangle it and rested it next to the other lingerie. He then pulled out a package with two pairs of thigh high stockings. He opened the packaging to examine them and was amazed at how thin they were. The stockings were nearly transparent.

Next he pulled out a small bottle of Victoria's Secret perfume called Tease and then finally a small tube of bright red lipstick.

It was still early and Marcus had finished his drink so he made himself a fresh one and then surveyed his new collection. What now?

He untied the robe and let it fall to the ground in a delicate flourish. He felt as though his mind and body had detached from each other and that he was merely watching the scene before him. He pulled the chemise over his head. The sensation of the silk against his skin as it covered him was electric.

He next picked up the purple straps. Upon closer examination, he deduced that they were in fact a garter belt. He had seen them worn in pornos but never had he seen one in real life. After a little trial and error he managed to get it strapped around his waist. The four garter straps dangled teasingly against his bare thighs. Sitting on the edge of his bed, he slowly pulled the stockings up his legs and figured out how to connect them to the garter.

He felt ridiculous but at the same time his cock was straining to be freed from the panties. He hadn't been so excited in a long time.

Marcus pulled off the cap from the lipstick and twisted the tube. A dark red shaft emerged from the silver tube. He closed his eyes and trying to remember how Christina had done it he ran the tube across his lips. He finished by puckering his lips together as he had seen her do it. He then reached for the perfume and sprayed it into the air. Thousands of droplets landed against his face and neck. His knees weakened as he was consumed by the delicate feminine aroma.

For a moment he felt like Christina was standing in front of him. He took another large swig of his vodka.

Marcus pulled out a porno DVD and walked to the living room. The air flowing across his stocking clad legs was incredible. He couldn't wait to jerk off.

He pushed the movie in the player and plopped down onto the couch. He reached for a bottle of lube and watched the movie.

It was one that he had watched many times before. The plumber shows up to help a hot blonde in a skimpy dress. Before long she is on her knees sucking his cock. They move to the bed room and he throws her down onto the bed.

Marcus was rubbing his cock through the panties as he watched and was ready for the main event. He tried to pull the panties down to free his cock and realized that they were stuck beneath the straps of the garter. Instead he pushed his lube covered hand inside the panties and stroked himself. His other hand was also between his legs rubbing his thighs and balls.

The plumber pulled off the woman's panties, a g-string much like he wore, and climbed between her legs. Marcus rubbed himself while watching a close up shot of the man's cock sliding into her pussy. A brief moment of panic hit him as he caught himself wondering what it felt like to be fucked like that. He felt ashamed as he imagined a cock sliding into him. He managed to shake off the thought and chalked it up to the vodka.

Marcus slid down into the couch and propped his feet up on his coffee table as his legs were pushed wide apart. He watched the woman getting fucked by the plumber while stroking himself. His right hand stroked his cock as best as it could with the panties on and his left rubbed his inner thigh. His fingers slid along thin ribbon that extended between his ass cheeks and he felt a strange pleasure in touching himself there.

His hand was still slick with lube when his middle finger slipped beneath the ribbon and made contact with his flesh just above his asshole. His finger moved in a slow circle until it came into contact with his soft opening.

On screen he watched as the plumbers cock pounded into her pussy. Again the thought drifted into his mind. What would that feel like? Marcus felt so incredibly feminine. He was dressed like a woman in lingerie while wearing lipstick and perfume. He felt a pang of jealousy that it wasn't him on that bed getting fucked by the plumber's big hard cock.

As these thoughts raced through his head his finger pushed just hard enough to slip inside of his asshole. He froze as the couple moaned on screen. His finger was pushed inside of him up to the first knuckle. His right hand still gripped tightly to his cock. He knew that he shouldn't like it but he did. He wiggled his finger and felt a wave of pleasure wash over his body.

Slowly he pushed his finger deeper into himself. When his finger was finally fully inside of his warm soft hole he gently fucked himself while stroking his cock. The plumber pulled his cock from the woman and stroked himself. The camera zoomed in on his hand and glistening cock. Marcus kept rubbing himself while he watched the plumber jerk off. His cock exploded in slow motion, sending a stream of milky white cum through the air. It landed on her pussy just as Marcus came himself, filling his new panties with his own sticky hot cream.

He filled his new panties with cum with his finger still buried to the hilt. The DVD continued in slow motion switching between the plumber's cock and her cum covered pussy. Marcus basked in the most intense orgasm of his life while watching the close up shot of another man's cock.

Several minutes later, Marcus had still not yet moved, the screen cut to a new scene. Marcus snapped himself out of it and decided that he needed to go to sleep. He was drunk enough that he didn't bother thinking too deeply about what had just happened.

He woke up the next morning with a severe hangover. He rolled out of bed only to find that he was still wearing the purple chemise, garter belt, stockings and g-string from the night before. His pillow had a bright red streak from his smeared lipstick as well.

He touched himself and noticed that the once soft silky fabric of his panties was now hard from his dried cum. His mind raced as he pieced together the events of the night before. He reached for his phone and called in sick to his office and then got up to make some coffee. Standing up in his room he suddenly felt self-conscious and wrapped himself in his new silk robe.

While sipping on his coffee he couldn't help but to feel horny again. He was ashamed of himself but he couldn't help it. He pressed play on the DVD that he left in the player from the night before and watched the familiar story of the plumber and the slutty housewife.

Marcus' cock sprang to attention as she unzipped the plumber's pants and unleashed his cock. Marcus pulled his cock out from his cum-stained panties and slathered it with lube. He stroked himself while his eyes fixated on the cock in her mouth.

With his hand rubbing his cock and his eyes fixed on the housewife's lips wrapped around the plumber's cock, Marcus' own mouth opened involuntarily. His tongue slid across his lips as the image of the cock on the screen entering his mouth briefly flashed through his head.

He suddenly remembered what else he had done the night before and considered it for a moment. Marcus wasn't ready to concede that he enjoyed it; so in an attempt to prove to himself that it didn't turn him on, he lubed up his finger and pushed it between his legs. He knew that he wouldn't like it as his finger penetrated his ass. Much to his dismay, his own body betrayed him. He immediately felt his sphincter contracting around his finger. He came almost as soon as his finger was fully inside of his body.

It wasn't a dream after all. He not only enjoyed dressing up in sexy lingerie but he also liked having something inside of his asshole.

Marcus looked back up at the screen as a ribbon of his cum arced across his living room floor. He eagerly stroked himself while watching the close up shot of the plumber's cock sliding out of her mouth. He surprised himself by again feeling jealous that it wasn't him sucking the plumber's cock.

There was no more denying it. Something had definitely changed.

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