Adventures of a Cross Dresser Ch. 01

Steve had slowly found a love for cross dressing. He'd come across it by accident, surfing round porn sites when he'd come across a scene with a guy in women's clothing. From then on, he'd realised how much it turned him on. The thought of being dressed up as a woman, being seen as a woman got him hot, the danger of being caught, the illicitness of it all.

To begin with he'd only done it at home, ordering clothes online, and then spending the day going around his chores in bra and panties, over which he'd wear a skirt and blouse. He'd then taken it further, watching you tube videos on how to apply make-up, practicing until he was an expert at applying all the layers. His cheekbones were almost ready made to accentuate the makeup applied, his features soft, almost feminine so that when he looked in the mirror after finishing, it was almost as if a lady was staring back at him.

Slowly, building up his nerve he began to venture out of the house, only short distances, blending in with the general public who had no idea of his true sex. But this wasn't enough for him, he wanted to combine his love of dressing with sex, like a real-life porn scene.

That was how he found himself online, chatting on a forum of like minded people. Slowly, he perused the forum, getting to know people, and starting to chat with some of them. One guy in particular, user name Big Daddy, he got on really well with.

"You should send me some pictures of you," he'd sent one evening, and Steve happily obliged, spending time to look his best, applying wig and make-up before posing in some lacy underwear.

"I'd love to treat you like a true lady," big Daddy had sent after seeing the pictures, much to Steve's delight. Over the next few days, they sorted out the logistics, Steve would go down to London and they'd spend the day together. What remained unsaid would be what happened at the end of the day, both knew where it would end, and for Steve he couldn't wait.

He'd decided to spend the whole weekend as a lady and so, on Friday afternoon after finishing early at work, he packed all he needed, and slowly transformed himself into Stephanie. His travelling outfit was nothing outlandish, simple cotton panties with a plain white bra, padded to give him a reasonable bosom, over which he put skinny jeans and a tight white t-shirt. He did his make-up to be understated, a small amount of eye-shadow and demure shaded lipstick to complete the image. He then affixed the blonde, shoulder length wig securely to his head, and headed out the door.

His journey down had been uneventful, but enjoyable, he had to stop smiling to himself as people went about their business on the train, unaware of who, or what, he was. The tube journey to his hotel was soon over, and he found himself checking in.

After giving the name of the booking, all sorted by Big Daddy, the receptionist handed over the keys. Another hurdle passed, Steve had been practicing putting on a feminine voice, but this was the first time he'd interacted with anyone as a woman. And he'd passed. She may have given him a funny look but hadn't said anything and Steve took that as a success.

"Do you want any help with your luggage?" the lady asked, pointing in the direction of a young bell boy loitering nearby.

Steve was about to refuse when he saw that the bell boy, no more than 19, was looking at him, 'her', in a hangdog way of someone who liked what they saw.

Maybe I could have a bit of fun here, he thought to himself, and so replied "Sure".

With a wave of a hand from the receptionist, the young man came forward, sweeping his blonde hair out of his eyes, head down as if scared to look into Steve's face, and picked up the suitcase. Smiling to him, Steve followed him into the lift.

Minutes later, they were in the suite and the young lad put Steve's suitcase down in the luggage rack, as Steve gazed around the suite. The bed was massive, and there was a doorway leading into the bathroom.

Steve realised that the young lad was still standing there, staring at him. Steve raised one eyebrow, as if to say "Yes, what?"

"Erm, is there anything else I can do for you?" the lad managed to utter, eyes still downcast.

"No, I think that's all" Steve said, smiling at how he was making the lad nervous.

Still the lad didn't move.

"Was there something I can do for you?" Steve asked moving closer to the boy.

"Well, usually I get a tip for bringing bags up," he replied.

"Oh, well, I don't have any money on me" Steve replied in an innocent tone, closing the gap to him, "but maybe I can give you something else instead?" he added as he placed a hand, complete with painted nails, flat on the uniformed chest, and gently rubbed his body through the material.

The bellboy couldn't talk, eyes fixed on the hand rubbing up and down his chest, all he could manage was a jerked nod.

Gently, Steve closed the gap, his lips gently caressing the boy's lips, as his other hand reached downwards. Finding the belt, he swiftly undid it and loosed the trousers, reaching under the pants and grabbing hold of the rigid dick below. Effortlessly he ran his hand up and down the shaft, whilst placing soft kisses on the bellboy's face. It didn't last long, with a shudder, he felt the body tense and then hot cum spurted out over is hand and soaked into the material below.

Pulling his hand out of the underwear, he provocatively licked the cum off his fingers, revelling in the salty taste on his lips.

"That will be all." He smiled again at the lad, who hadn't moved from his initial position.

A small nod was all he got, before the boy finally moved, swiftly pulling up him trousers and fleeing out the door, much more flushed than when he entered.

Smiling to himself, enjoying the start to the weekend, Steve finished the rest of the cum on his hands, before flopping onto the bed.

A couple of hours later, refreshed from a cooling shower, Steve was ready to head out again. His agreement with Big Daddy wasn't to start until Saturday morning, so he'd decided to head out into London and see what the nightlife could offer him. Or offer her, he corrected himself, planning on being Stephanie again.

He was blessed with not being overly hairy, and so maintaining shaved arms and legs, to give a more feminine appearance, had not been hard. Similarly, he didn't grow much of a beard and regular shaving kept him looking clear shaven. After his shower, he reapplied the make-up, going a bit more over the top this time, heavier eye shadow, bright red lipstick, until he was bordering on too much. But it gave the right impression, a girl on a night out looking for a good time. He applied the perfume he'd brought, Chloe, and moved into the bedroom to get dressed.

This time, he put on more racy underwear, the lacy feel causing tingles through his body as it rubbed against his skin. Over it, he put on a short shiny black leather skirt, barely enough to cover his ass, and a floaty, summery halter neck top, which left a little of his midriff open.

After putting his keys and money into a small clutch bag, he took out the heels he'd brought with him, and stepped into them. This had been the hardest part, getting used to walking in heels, and he still hadn't mastered it, meaning he'd gone for a strappy pair with only a small heel.

Stepping out in the night, he started down the road. The gay club he'd identified wasn't that far away, and as luck would have it, there was a cross dressing night on, which suited him fine. He could have got a cab, but instead he wanted to walk, feel the night air on his legs as he wandered down the street.

Following the map on his phone, he was making good progress, and was lost in his own world as he walked, until he heard a shout.

"Oi love, looking for a good time?" the coarse voice cried from over the road in a broad cockney accent.

Turned to where the voice had come from, Steve saw a guy in his mid-twenties, leading up against a wall.

"What makes you think that?" Steve called back in his feminine voice.

"Your outfit, either you're on the pull, or you're working, if you know what I mean" the man lecherously said.

It was a dangerous thought, but Steve decided to have some more fun.

"So, which do you think it is?" Steve demurely asked, moving across the road to the other side.

"Well, classy bird like you, can't see you being a street worker" the man smiled, knowing that by crossing the street he was getting something.

"so, what you offering?" Steve replied smiling sweetly up at him

"Why don't you come back to mine and see?" the man said.

"Oh, I'm not THAT kind of girl" Steve said, knowing the dangers of going to a random guy's house alone, "but maybe I can give you a little something here and now?" he added, rubbing his hand over the bulge forming in the guy's jeans.

"now we're talking" the guy grinned pulling Steve towards a nearby alley.

Once out of the streetlight, the guy pulled Steve into a kiss, his rough stubble rubbing Steve's jaw. He tasted of fags and booze, the taste bitter to Steve's mouth. Quickly, not wanting to taste any more, and conscious that the guy's roving hands were in danger of finding out the truth, Steve dropped to his knees.

Deftly, her undid the belt and pulled down the jeans and underwear, letting the guys rock hard cock spring free. At 7 inches it reared in front of Steve face.

"Like what you see?" the guy said, thrusting his crotch forward so the dick slapped Steve in the face.

Without answering, Steve took the dick in one hand, and slowly ran his fingers along it, letting the nails lightly dig in to provoke a hiss of ecstasy from the guy.

His other hand slowly massaged the guys balls, as he stroked up and down. After a minute he started to lick the outside of the cock, his tongue flicking out of his painted lips, moistening the shaft as he continued to stroke. Then he finally opened his mouth and took the guy's cock into it. Suddenly, almost forcefully, the guy thrust forward again, causing Steve to gag as the tip pressed onto the back of his throat.

"Yeh, take that dick, take it all" the guy urged, thrusting forward again. This time, Steve was ready and moved his head in time so it wasn't so bad. Slowly, teasingly, he massaged the guy as he bobbed his head back and forth, allowing him to nearly fall out before ramming forward once more.

He could taste the pre-cum now, his tongue darting over the slit as it oozed out, lapping it up. The guy was increasing his speed of thrusts now, and Steve knew it was almost time.

"Fuuck" the guy cried, with one final thrust as he came. Wave and wave of cum fired into Steve's mouth, thick and glutinous as it filled his mouth. Steve kept the cock in his mouth until no more came, not wanting to spill anything. Slyly, almost shyly, he looked up at the guy, and made it obvious as he swallowed the whole load.

"Dame girl, you can suck." The guy replied, pulling his dick out of Steve's mouth with an audible pop, strings of saliva and cum trailing after it. "Are you sure you don't want to come back."

"I think that's enough fun for one night." Steve replied, a little out of breath.

"Have it your way, you don't know what you're missing" the guy replied, tucking himself away before sauntering off, leaving Steve alone in the alleyway.

After a minute or so to regain his breath, Steve stepped back into the light of the street. He'd only gone a few steps when he caught sight of his reflection in the shop window. His hair was a mess, ruffled from where the guy had been holding his head, and his lipstick was a mess, smudged all over his face.

Reaching into his bag, he got a compact out, and slowly, with great care, reapplied the lippy and made the best job he could of the hair. Looking vaguely presentable now, he put the mirror away, and continued to the club.

The club was amazing. Steve had never seen so many guys dressed as girls, girls as boys, men and women not dressed up, but still enjoying those that were. The music was loud, drowning out any chance of conversation, and so he'd had a few drinks before heading onto the dance floor. There he'd danced with some men who were women, and also some men who were men, but none of them had really taken his fancy.

Now it was nearly 1am, and he was a little bit tipsy and considering heading back to the hotel, needing a good sleep before meeting Big Daddy tomorrow. Slowly, he made his way towards the exit, when he felt a hand gently grab his arm. He felt a mouth press near his ear, which sounded like a whisper, but was probably a shout.

"Not leaving already?" it asked, "I haven't even had chance to have a dance with you."

Steve turned, ready to beg off that he had to be up early in the morning, when he took in the person speaking to him.

This was a man. Not one of those dressed up as a woman, but a real man. His bulging muscles looked to be trying to escape from the tight white t-shirt he wore, his face looked deeply tanned, his short hair sparking form the sweat formed from the humid interior of the club. All in all, a hottie Steve thought.

"Well in that case, let's dance!" he smiled back, allowing the guy to pull him by the hand onto the dance floor.

In two songs they were grinding up and down each other, in three they were passionately making out as the music blared around them, and in five they both agreed it was time to go elsewhere.

Laughing as they existed the club, Steve hailed down a passing cab before the other guy pulled him into an embrace for a deep kiss. Their tongues entwined briefly, only interrupted as the taxi pulled up.

Breaking for air, they climbed into the cab, and Steve gave the cabbie the hotel address.

Minutes later, they arrived in the deserted lobby of the hotel, barely keeping their hands off each other. They stepped into the lift and Steve pressed the floor button, before turning back to the handsome guy, their lips pressed together one more in a wild passionate kiss. The doors opened and they almost ran to the door, pausing briefly as Steve opened it, before turning to each other once again.

They fell into each other, Steve leaning up against the wall as the other guy kissed him again. The short beard the other guy had rubbed against Steve's skin, but unlike earlier in the alley, this time he didn't seem to care. Tongues entwined as they mashed up against each other, Steve's arms wrapped around the guys strong body, the guy's hands reaching down to squeeze Steve's ass.

"oh baby, I'm going to fuck you so hard" the man growled into Steve face, almost as if this was a man and women, rather than two men.

Keeping with the moment, Steve replied "yes, take me, I want you're cock inside me."

Continuing the kiss, the guy reached up behind Steve and quickly untied the halter neck, allowing it drop to the ground. He then reached down and undid the skirt, pulling the zip down so that it too fell to the floor. This left Steve standing there, in just his bra and panties, the black lace standing out against his white skin, his dick bulging the panties, straining to be free.

"So hot," the man whispered, running his hands down the side of Steve's abs.

"My turn," Steve smiled back, reaching out and pulling the t-shirt over the man's head, revealing a well-toned body. He must spend a lot of time outside, Steve thought, taking in the tanned body, the washboard abs and the bulging arms. He felt himself pulled forward once more, and they kissed again, Steve running his hands over the man's body, feeling the outline of ever muscle, the strength of the arms holding him.

After a minute he broke the kiss, and reached down, pulling the trousers and pants down, leaving the guy naked. The large cock, semi erect caught Steve's attention, and this time when they kissed, he reaches down, hands gently massaging the cock to larger proportions as they continued to explore each other's mouths. The guy's hands continued to massage his ass, gently squeezing and probing, causing him to moan into the other man's lips.

For the second time that night, he knelt down, catching sight of himself as he did in the full-length mirror. How hot was this, he thought to himself as he saw his own lithe body, scantily clad in women's underwear, reaching for a hard cock to stick into his mouth.

Running his tongue down the whole length, he went all the way down, and took one of the balls into his mouth, before trailing across to the other and doing the same. Cupping them in one hand, he slowly trailed his tongue back up the shaft, before darting it into the tip, tasting the pre-cum oozing out, causing the guy to gasp in delight.

"Suck that dick, you dirty whore" the guy panted, his hands roughly pushing Steve's head into his groin. Opening his painted mouth, Steve took the top half of the cock into his mouth, allowing him painted hands to run up and down the lower half, moist with his saliva.

He was bobbing his head back and forth now, mouth and hand in perfect time, as he slowly increased his pace. Letting go with his hand, he took more of the shaft in. The hands, both of them now were behind his head, forcing him to take more into his mouth. Luckily, he was able take the full length in with only minor gagging, before drawing his head back, allowing the cock to almost fall out, saliva and cum dribbling out of his mouth and down his chin as he did.

The guy rocked his hips forward, and pushed Steve's head forward, causing him to take the full length into his mouth again. Steve had his hands on the other guy's ass now, partly to steady himself and partly to feel the lovely mounds between his fingers. He squeezed the taut muscles, which flexed under his touch as the guy thrust.

The end came suddenly, the guy cumming as his full length was impaled in Steve's mouth, causing waves of goo to hit the back of his throat. Steve gagged as it came, swirling the cum around in his mouth, savouring the taste.

The guy pulled his cock out, cum and saliva trailing behind, before shoving his slimy dick in Steve's face, covering it in the juices of their passion, smearing it over his cheeks, eyelids and into his hair. Steve swallowed the cum, before standing up.

Face a mess, he kissed he guy forcefully with an open mouth, pulling him tight with one hand around the back of his neck, and their tongues met once more. His cock was rigid under the delicate material of his panties, pre-cum smearing the inside of the delicate material.

"Fuck me!" he whispered into the other guy's mouth, panting from their endeavours.

In return the guy maneuvered them towards the bed, lips locked, before pushing Steve backwards onto the mattress.

Swiftly, he leant over Steve, and with deft hands pulled his panties down, allowing Steve's cock to spring out, down over the legs before dropping them carelessly to the floor.

With a practiced motion, he flipped Steve over onto his belly, and Steve assisted by burrowing his face into a pillow, offering his ass to the ceiling.

He gasped out load as he felt a warm tongue dart around his hole, followed by a moist finger that gently probed his tight asshole. Moaning out loud, he encouraged the guy.

"Yes, that's where I want you to fuck me, deep into my ass."

The guy slowly inserted one finger into Steve's ass, his other caressing and toying with Steve's ass cheeks. Then the tongue was back, exploring all around the hole, tongue then darting into the hole, before a second finger followed the first.

The caress of the hands was getting Steve harder, his now rock-hard cock pressed between his stomach and the bed. Expertly, the guy continued to twirl his fingers, thrusting them in an out, like a practice for what was to come, slowly opening the hole.

Steve looked over his shoulder at the other guy, watching as he finger-fucked his ass. After some time, the guy stood up, and pulled Steve backwards, until his ass was on the edge of the bed, legs dangling off the edge. He saw the guy give his shaft a couple of tugs, getting it erect and hard once rock-hard more.