Warning: This fic has been written by a slightly tipsy twenty-something with a heavy crossdressing-kink. Enjoy.
Sherlock liked dressing up since he had been a child. One of the few advantages of his parents' effort to get him befriended with other children was that he was able to put on several costumes for theme-birthday-parties, Halloween or other events. Most of the time Sherlock wanted to go as a pirate but sometimes he went for the classic cowboy costume or an impression of a historic person – which of course non of his forced friends would recognize.
He could still remember clearly one incident though that had left his mum slightly baffled and angry: The seventh birthday of Daphne, one of his female classmates. She desperately wanted to have a medieval times party, so all of the guests had to dress up as knights or princesses.
Mummy Holmes was relieved her little boy was invited to another birthday party even after deducing the parents of the birthday girl were about to split up at the last one. She pushed Sherlock into a small costume store at their home town and went straight for the knights costumes. After several minutes of rummaging through dozens of suits, armours and swords, she swirled around with a red and white costume but couldn't find her son anywhere. "William? Billy? Where are you? I think I've found something you might like."
A muffled voice came from behind the curtain of the changing room.
"I've already got something, mummy. Just wait a second."
Mrs. Holmes made her way to the back of the store and was shocked when Sherlock pushed away the dark blue curtain and stepped into the light.
"William! You can't wear that.!"
"Why not? I look nice in it, it fits the theme and it's comfortable."
"But it's a costume for girls."
Sherlock had turned around to face the mirror. He still thought he looked wonderful in the light green dress, which made his eyes sparkle. It was a typical princess-dress, with glitter all over it and he even wore the small plastic diadem that came with it.
"Now get out of it and try this one here on. You'll look amazing and the kids will like you."
"But I don't need the kids to like me. They're dull. And I like this dress."
"Stop. No more talking. Get out of the dress. Now."
It was the only time his mother would use a voice of commanding and the first time he felt a strange sensation in his stomach. 21 years later, he finally knew what this sensation meant.
When John entered the club, he was deeply impressed by it's space and style. Of course he had been to several swinger clubs before and there had been good ones as well as bad ones, but none of them could reach the level of the "Sinsation". A young woman with black hair had greeted him and he was given a small bracelet with a key for a locker in the changing area and a number on it. No need to carry cash around. Not that there would be a convenient place for cash in the outfit he had chosen for the day.
The club had three floors: The main floor with a lounge and bar, a classy looking restaurant area and even a small dancing space; the top floor which where only couples had access (also including the couples that had just met that evening) and the basement with showers, whirlpools and some bdsm-areas. John gulped at the sight of all the people gathering at the bar and getting their drinks. There hadn't been many occasions when he would go to a club on his own, in fact he rather preferred the nights for couples. But somehow he didn't want to explain to one of his casual dated that he liked to suck a cock once in a while and that he had a strong kink for cross dressers.
He made his way to the basement and quickly got out of his jumper, his jeans and his underwear. The clothing was thrown into a locker and John opened the backpack he brought along to retrieve his club-outfit: Tight black leather shorts, a matching tank top and knee-high boots that resembled his military boots but were slightly higher and had a special pocket attached to the side where he could store his riding crop.
One last look into the mirror and he decided to check the club for any potential play partner.
As expected the lounge area was already crowded with guests who were chatting, flirting or making out. John walked up to bar and felt several people staring at him. Though he wasn't as fit as in his military days he was still one of the most handsome men in the club and his clothes underlined his firm body perfectly.
"What can I get you, sweetheart?", the tall bartender asked. The guy was obviously gay and winked at John. "It's a shame I'm not allowed to have fun with our guests."
The doctor smirked, happy that he was still able to turn someone's head.
"A Glenfiddich. Without ice.", John demanded while scanning the room. "Nice club you've got here."
"Oh, is it your first visit here? You'll like it for sure. Give the crowd another thirty minuted and it's getting really hot."
The single malt was served to John who smiled and turned around, ready to have some fun.
With the glass in his left hand he quickly walked to a couple he had spotted while waiting for his drink. The two of them looked rather shy but they were quite beautiful. A tall woman in her late thirties with short brown hair and large natural breasts and in her company was an obviously submissive Sissy in a maid-dress with a collar around her neck.
"Good evening. Looking for some fun? I'm John."
The female part of the couple was the one to answer.
"Oh, hi there. I'm Melissa, this is Lola. You're probably a nice guy but we're rather looking for fem doms and other Sissies, sorry."
"No need to feel sorry.", John smiled. "How do you like it here so far? Have you been here before?"
"Yeah, we have. Pretty often, most of the tranny-nights we're visiting. What is it, Lola?" she asked, when the Sissy had nudged her and pointed at the dancing area. The music was growing a bit louder a lot of guests had gathered on the leather sofas or were standing around the small space. In the middle of it was a single pole and a long and slender figure was making her way towards it.
Melissa gasped and happily announced: "Oh fuck yeah, she's finally here again."
John turned around and eyed the woman, who was standing with her back to the crowd. Not a biological woman though, the shoulder part looked rather male but the body was indeed quite feminine. She wore a short red dress made of lace and velvet, black hold-up stockings and red high heels. No jewellery, only a small velvet bow in her black curls. The way she moved was intoxicating and she hadn't even started dancing yet.
"Wait till you see her face and she starts her dance. She's probably the most wanted person in this club. I haven't seen her in some months, I thought she stopped coming at all. I wish we could spend just one night with her.", Melissa told John.
"Well, why don't you? The two of you are very pretty so that shouldn't be an issue. Or is she just into men?"
"She won't have sex with anyone here. Just comes around to dance, take a drink and let the guests admire her. She's not a professional though. But one day she told me her heart belongs to someone else."
In this very moment the woman grabbed the pole with one hand and swung herself around until she faced her admirers. Her eyes were cast to the ground but John didn't need to take a second look.
"Oh bloody hell."
"What is it? John? Do you know her?"
"Fuck...yes. Well. At least her male part. It's my flat mate."
John had to admit: Sherlock was the sexiest thing he had ever seen. He, or rather she, wore red lipstick, matching her dress, rouge and black eye-liner. Still it was unmistakably Sherlock – with the sharp cheekbones, the perfect plush lips and the sky-coloured eyes.
A new song started and Sherlock started dancing. In an instant the crowd was cheering and clapping. From what he could hear and see John deduced his best friend had an incredible talent for pole dancing and was obviously called "Sherly" when he wore this kind of stuff. John took a few steps towards the dancing area and his eyes grew wider every second. Sherlock was obviously totally lost in his thoughts when he moved like a fucking goddess around the pole, making the most sexy poses. Long limps wrapped around the cool metal and the red dress revealed a nice view on his bum as Sherlock slid down the pole.
None of the guests got too close though, everyone seemed to admire Sherlock but no one would try and grab that glorious body.
The song went on for what seemed like several hours to John and he already felt his trousers becoming way too tight. Of course he knew Sherlock was an incredibly handsome man but this was more than he had ever imagined. And damned, he had imagined a lot when it came to the body of his "married to his work"-flat mate.
As everyone around him started clapping furiously, John was torn from his thoughts and realized the song must have ended. Sherlock left the pole and friendly declined every offer to "have fun" or "get it on". He look long strides to bar, eyes still locked on the floor, when John cut off his way.
"Sherly.", John said, not wanting to address Sherlock's male side right now.
The woman froze on the spot, not moving any inch forward. People around them started to whisper, some of them chuckled or pitied the man, who obviously had no idea about that Sherly would turn him down as well.
"Sherly, look at me." Though his voice sounded warm and full of affection, it was still spoken as an order.
The younger one did what he was told, lifting his gaze and meeting John's eyes. Shock, fear, embarrassment, hope – all these emotions were visible on Sherlock's face and John had a hard time not to launch himself forward to pull his friend into a tight hug.
Instead he extended his hand and smiled.
"Ready to have a good time with me?"
A simple question but it tore down several walls in Sherlock's mind palace, making him rebuild the "John"-room in a couple of seconds, as a shy smile spread on his face.
He took the offered hand and the crowd around them went nuts with joy and envy as they heard the reply.
"Of course I am."