Matt looked exceptionally young for his age and blessed with a complexion that meant he wasn’t all that troubled by facial hair. Spots were non-existent, always had been, even in his teens. Yet at twenty-eight years old you could never classify him as normal. His slim body, born out of long legs and a standard-sized upper torso fulfilled all his needs. He couldn’t be described as ripped at all. In fact, with the right hair, makeup and clothes he would pass as a woman.
It wasn’t that he hadn’t tried either. One of his girlfriends once made him dress up in her clothes so that she could pretend to have lesbian sex. It backfired on her, Matt liked the feel of the stockings on his long legs far too much. The basque and suspenders felt even better, and the long black dress she made him wear looked spectacular on him. It was her best black evening-wear dress, the one she would wear to parties. The only things he couldn’t wear were her size four and a half heels. They were far too small.
She even made him wear lipstick and bought him a blonde wig. It was her fantasy after all; Matt would have chosen a black wig as he always liked brunettes better. By the time he was dressed for her, he looked delectable. Ready to eat, as she put it. The sex turned out to be unbelievably hot especially when she simulating fucking him while his stockinged legs were wrapped around her waist.
Let’s just say that when they split up, her dress got misplaced when she moved out of his flat, a tube of her nicest red lipstick also fell behind one of the seats of the sofa and her stockings were caught up at the bottom of the washing basket. It was unfortunate that he couldn’t keep the basque, but once she had vacated the flat he did buy a size eight pair of heels and a suspender belt. Why wouldn’t he, seeing as he enjoyed dressing up so much.
At first, it was just the dressing in the comfort of his own home. He looked the part and masturbation sessions soon turned out to be far more exciting than they had ever been. For four months he never actually bothered to find another girlfriend or partner. He was happy to play the tart at weekends and have fun on his own.
The more he liked the feel of his new clothes the more he experimented. Wearing knickers out in public became the norm, sometimes he would even wear hold up stockings but they didn’t feel the same under jeans or trousers. There was something about the feel of fresh air as it brushed past the nylon or silk fabric that made his skin stand on edge.
He even shaved his legs; no big deal, he thought, loads of cyclists shaved their legs.
Women were attracted to him though, and he did slip into a few relationships, however short term they were. One girlfriend felt disgusted when he asked her whether she would like him to dress sexily. Apparently, that wasn’t what men did. Men fucked. Needless to say, she didn’t last long. There were one or two that entertained the idea but he could see that they weren’t really into it.
That’s when Matt bought his very own wig. A black-haired one, and that’s when he started to shave as close as he could, buying a proper shaver rather than those electric ones that only got half the job done. He even bought more female clothes so that he experiment with dress styles such as jeans and tops. He would parade around his flat in whatever gear he fancied, wear lipstick and his wig and get used to walking in heels. He masturbated whenever he dressed up and that amounted to about four to five times a week.
Meeting the outside world was a gradual progression, but it happened. He eventually left his flat and walked outside to the bus stop where he caught a bus and rode ten miles to a pub on the outskirts of town. He reasoned that someone in a pub close by might recognise him.
He felt quite cool sipping a Gin and tonic, after stopping himself from ordering a pint of beer, not that that would have been stupid but it was certainly less prevalent where he lived.
He was enjoying the evening on his own. Just being someone new, someone different. He liked his reflection in the mirrors behind the bar, he loved the feel of the clothes he had on and for the first time in a long time, he didn’t feel like he had to make excuses to anyone. This was him.
The pub visit was to become a regular haunt with him. That all changed one night when a bloke started to chat him up. His voice still resonated with deep tones and he could feel the tension between them. He wasn’t sure whether he should try and squeak a little higher or just be normal. He went with normal and after about ten minutes of attempted conversation, he finished his Gin and tonic and made his excuses to leave. The other thing he noticed while he finished his drink was that his cock had grown. Luckily he was wearing ripped jeans, otherwise, it may well have embarrassed him in a short skirt.
The bus home was a time of reflection, but the one thing that he couldn’t stop thinking about was the reaction he had to the guy standing next to him. The fact that he got chatted up at all indicated that he must have come across as very feminine. Female even.
When he reached home, he had decided that change was needed. At least for a while.
Matt started to look at some different websites; yes, they still included porn, but the others concentrated on cross-dressers, transexuals and gay people. He had decided that he would be better off with like-minded people rather than have guys come on to him that would get offended. Better to be safe than sorry.
In a relatively short time, Matt had questioned his sexuality, questioned his liking for wearing women’s clothes to the point that he actually passed as one, questioned his relationships with other women and men. He was still a resolute male when it came to his work but he wondered whether that could change too. His life was in turmoil that lasted a good few weeks.
The breaking moment was when he received a message from another crossdresser on one of his many websites. One that lived quite close, and one that wanted to meet him. That was when he started to question his life all over again. Did he want to go through with it? Did he want to meet another crossdresser? Would he/she expect anything to happen?
Try as he may, he couldn’t get the thought out of his head and that’s when the conversation started between Mattea and Stephie. It started with words, a few at first and then several sentences were strung together and then stories started emerging. Stephie was adamant that she should be regarded as a gurl. Pictures were added and emails sent with those famous paperclips that made both Stephie and Mattea excited. From the images, Mattea could see that Stephie’s breasts were real or at least enhanced in some way. She was much further down the road than Mattea was.
It was no surprise to him that Stephie wanted them to meet and once he had looked at her profile pictures and viewed the images that had been emailed, he too felt the same. It had taken a long time though and the journey was fraught with questions.
At first, there was nothing sexual that was driving his reasoning, just that two like-minded people could get together have a drink and laugh at a place that accepted them for who they were.
They met at a place called “The Church”. As its name suggested it was a disused church that had been made into a new-world bar with the highest ceilings that any bar could have. Seating was comprised of high bar stools and tables together with some comfy leather sofas. The décor was chic, the ambience was just right and Stephie was chic too as she stood outside the bar waiting for Mattea to arrive.
The greeting was not that of a normal couple, there was no kiss on the cheek, no handshake, just the obligatory nod of the head and the rise of a hand to indicate that they should go inside, which they duly did. Drinks were ordered, seats were chosen and then coats removed. Mattea smiled when he saw that Stephie was wearing the same yellow dress that he had thought to wear that evening but changed it to a little black number.
Stephie was also tall, with blonde hair, blue eyes and with much larger breasts than Mattea had. Breast sizes turned out to be a common topic of conversation throughout the night. Mattea wore his black number and made every effort to look smart and attractive.
Stephie’s hand reached out to him and stroked his face. “You look beautiful,” she said.
“So do you,” he replied.
The soft-touch of affection seemed to relax the tension in the air quite considerably. They were both thankful for it. For Mattea, it had been a long journey. For Stephie, a long wait.
The conversation was brought around to gender and Stephie questioned Mattea as to why he always referred to himself as he rather than she or a gurl. He shrugged, not knowing the answer but just accepting that he identified as someone that liked wearing women’s clothes rather than being a woman. It was a lifeless excuse and he knew it. In his heart, he knew it was more than that.
The topic of conversation was promptly moved along and there was no end of paths that they followed, and dead-ends they finished in. It wasn’t long before Mattea found himself wondering what a hot gurl did with her penis.
He had already found his to be stiffening but this time it was secured tightly in his knickers.
Stephie suggested that she buy the next round of drinks and Mattea agreed. Left to his thoughts he considered what to do next. He turned to look at Stephie by the bar and couldn’t help but find his cock stiffening as he drank in the swell of her bottom and her slim waist. Of course, he could already see what the barman was looking at which caused an amused smile to appear on his face.
Stephie carried the drinks back and Mattea couldn’t have been more surprised to see that her cock was pressing against her dress making it tent ever so slightly. When she took her seat Mattea leaned in to whisper in her ear.
“Was that show for me? Or did the barman turn you on?”
Stephie smiled. “A little of both actually, I love it when a bloke regards me as a woman and can’t help but leer at my assets. But in all honesty, it was stiffer when I made my way to the bar, if only you had noticed.”
Mattea changed seats. He sidled in beside Stephie and took a big sip of his drink. He needed Dutch courage for his next step. And there it was. His hand on the edge of Stephie’s dress and snaking its way upward beneath the table. He looked into her eyes but her eyes were lowered as they watched his hand get closer to her sex.
Stephie’s lips quivered as Mattea’s fingers brushed her cottoned covered cock. She looked up at the people on adjoining tables but they were all engrossed in their own little worlds. Not giving a fuck or not noticing that her cock had grown and that Mattea had encircled it with his hands. He leaned into Stephie.
“I want to suck it.” The request just came out of his mouth. He never gave it a second thought. It seemed that all the dressing up, the wigs, the lipstick were all leading up to the moment when he would make that remark to someone.
She looked at him, surprised but excited. “Really?”
“Yes, really,” he replied.
And he did. He did. He wanted his mouth around her warm hot cock. He wanted to suck on her bulbous head and let it slide into his mouth and as far down his throat as he could get it.
Stephie reached down and pushed his hand away.
“Is something wrong?” asked Mattea.
“It will be if I stand up right now, and we need to go somewhere.”
Mattea smiled and licked his lips.
Stephie looked around the pub. The toilets were upstairs, but she shook her head; they would be too small and would be too busy at this time of night. The outside would be too cold, although there was an alleyway not that far behind The Church that she had used in the past but that was a much warmer night.
“My car?” she suggested in the end. “It’s parked in the multi-storey. Yeah?” Mattea nodded silently and they quickly finished their drinks.
It was an effort, to say the least. It took all their strength to leave the place without their cocks giving them away. Stephie had to adjust her knickers and push her cock back as far as it would go. Both of them were relieved to get out of the place without being noticed and they giggled as they stumbled down a small alleyway and out onto the main road.
It was Mattea that slipped his hand around Stephie’s waist, drawing her closer to him. They cuddled together as they walked towards the direction of the cold air. They caught the lift to the fourth floor of the car park and Mattea’s hand once more found the curve of Stephie’s cock, bending downwards and between her legs – it was unnatural and he couldn’t wait to release it.
They came upon Stephie’s car and she had just unlocked it when Mattea pushed her against the car door. His hand stroked her cock underneath her yellow dress. His eyes locked onto hers and his lips opened.
Stephie was on him like a Tiger. Her lips clashed fast to his and her tongue darted between them. They battled each other as their heads twisted and turned as their feverish kisses took hold. Mattea’s hand had risen beneath Stephie’s dress and was slipping effortlessly down her knickers; pushing them down as his hand descended further and further until they were around the tops of her thighs. Her cock sprung free and Mattea sighed when his hand caught it, stroked it and relished the feel of it.
The kissing only stopped when Mattea broke off. Stephie’s cock was upright and firm; holding her dress up all on its own. Mattea sunk to his knees and looked up into her eyes.
“You don’t have to if you don’t want to,” Stephie said.
“I want to, very much,” he replied, before sinking his mouth over the head of her cock.
Mattea sucked on it. The most remarkable first memory was the heat. The stiffness and the silkiness of Stephie’s cock was the second most memorable feeling. Mattea pulled it downwards with one hand and allowed himself to slip it further into his mouth. His other hand caressed her thighs paying particular attention to her stocking tops. Before long both hands were caressing a mix of skin and silk as Mattea bobbed his head and sucked on the bulbous end, willing it to spurt into his mouth.
He could feel Stephie’s cock twitch and he sucked with hope and excitement. His hands came upon her bottom and he pulled her towards him.
A deep sigh left Stephie’s lips. She looked down on her new lover and relished the thought of her cock disappearing between his lips. Her hands could not deny her feelings and they soon rested on the back of his head. Mattea breathed deeply through his nose as her gentle hands caressed his hair and her bottom eased itself forward in slow motion for a few sensuous strokes.
With a single push of her cock into his waiting mouth, Stephie spurted. She held his head still and lifted her bottom towards his head. Her cock pushed slightly upwards into the roof of Mattea’s mouth and gush after gush was released into it. Not a drop was lost and she could feel Mattea swallow when he had the chance. His hands clenched her fleshy bottom as he relished the smell, the taste and the heat of Stephie’s white cream.
It wasn’t that long before Stephie released her lover’s head. She grabbed him by the shoulders and pulled him to his feet. Planting a passionate kiss on his lips was just a ruse to get her tongue between them and share her sperm.
Mattea’s butterflies bruised his insides. It was the most passionate kiss he had ever received, a most intense and lustful kiss where two people shared more than just moments of lust.
“I want to take you home with me,” said Stephie.
Mattea broke off the embrace, pushed Stephie back towards the car and walked away from her. It had taken him only a few steps to circle the car before he opened the passenger car door and sat down.
“Come on, get in and drive,” he shouted through the windscreen.
Stephie smiled to herself, bit her lower lip and with fire in her eyes turned and opened the car door.
“Off or on?” she asked pointing to her knickers that lay at half-mast and collecting the remnants of sperm that leaked out of the end of her cock.
“Off,” he replied.
She lowered her panties to the floor and stepped out of them, throwing them into Mattea’s face as she sat down in the driver’s seat.
“Home it is then,” she said.
Mattea took no time in smelling and sucking on the panties before reaching out with his hand to feel Stephie’s flesh-covered gear stick.
It had been a long wait, and the relief was written all over her face. Yet the wait had been worth it, and here he was, in her car, fondling her cock, with her driving home to a night of passion and wanton lust. Stephie couldn’t wait to feel his sperm sliding down her throat. It would be blissful. But thoughts of all those other things started to excite her.
Before long, she would be driving like a maniac, a record-breaking attempt to get home as quickly as she could.
