• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Ragdoll

Ragdoll

I'd always assumed I was 100%, no exceptions, one-track-minded Gay; as gay as the day is long. Pretty damn gay. Really, nothing's happened that should technically directly challenge that, there was still plenty of cock involved... but I can't deny the fact I was attracted to some very feminine features. It's not even like he (or rather she) was crossdressing in an inherently sexual way, perhaps a bit racy. She was just having a laugh, but god she was so damn sexy! I never really meant to fall for a Drag Queen, but let me tell you it's a hell of a ride.

It was a cold winter in London, cold enough for there to be snow on the ground, even in the heart of the city. I say snow, it was the half-stuff; melting and sooty, yet freezing and also brilliant white. The cars at Piccadilly circus trudged on heedless of the weather, robotically pressing onwards. I was alone in that bleak midwinter, standing in tiny road lit by a sliver of the giant advertisement screen, gazing onto a glimpse of the eternal traffic. My boyfriend had just dumped me: my dick was too big. Nah, just kidding, I'm never one to brag really; he'd actually broken up with me because he said I was too thoughtful, I never made decisions, and I could never be impulsive. Hm. He could be right, I thought.

I gazed around me - to my left my favourite cocktail bar (until my now ex-boyfriend dumped me there) and behind me, the gateway to Soho. Hm. I'd show him impulsive, I thought. I walked towards the square, the slush-snow turning slightly whiter as I advanced, then dirtier and dirtier as I got nearer to Soho proper. I passed my reflection in the darkened glass of a sex shop as I walked through the village. I looked really cold, my straight nose gone red, contrasting my pale skin and watery brown eyes. My hair, sandy blonde, was being whipped about in the wind. My ex would probably regret it, I thought; I was tall, and reasonably toned - I had been called a 'twunk' before. I was a switch, so it made sense. That was one particular decision I could never make that drove my ex insane. Top or bottom, top or bottom: maybe I should have been more assertive in that department. I looked through my reflection at the sex toys, barely visible behind the glass. Maybe I should go in? But then, why? Dammit! I was being indecisive again! I tugged my scarf up my pale, frost-bitten lips and stormed off in a huff.

I was wandering round Soho for a while, looking for something impressively 'out-there' to do when I looked up and saw an angel. A neon angel, welcoming people in to a hip and trendy little club, a gay bar for people who didn't really know the town and just wanted to do something. Which was me - I wanted to do something. I turned to the door and was greeted by another angel: Ragdoll. From tonight until the end of January, the bar had Ragdoll performing every night, an up-and-coming Drag artist who could sing, dance, and crack jokes like a mad-woman. I was nearly up-and-coming just looking at her poster. Everything was over-elaborate, sure, but it was fun, cute, sexy! Huge winged black eyeliner and bright red lipstick, with a little bit of pink blush on the cheeks, and the rest made up to accentuate feminine features. Her make-up was on point, and her hair looked so authentic - a beautiful brown wig that flowed behind her. She looked like a very pretty, if a bit eccentric, girl. I decided to go in, not on the face of a pretty girl, no! Of course not, I was gay after all. I mean, I'd always loved Drag anyway, fun and camp and kitschy - it was also a great fuck you to the expected gender roles which is always a plus. I was going in simply in the expectation of a great Drag performance. Well, I certainly got a great performance.

The room was tolerably lit, you could see, but it was definitely on the lower side - ambient. There were deep reds and light blues that gave it a very romantic feel, emphasised by the petite round tables hugging each other, and the low stage - it was what the theatre buffs call 'intimate'. A normal looking guy, with a brown beard and a red flannel shirt, came up to me with a friendly smile - the type of guy that reminds me why I switch.

"Hey" he said, with maybe a Scottish accent? Though it could have been Irish "this your first time here?" He was so friendly, so hot and he smelt so nice. I was distracted, and could only nod mutely. "Shy, are we? Haha, no worries, Ragdoll doesn't bite. Take a seat at the front, someone will be along to offer drinks." I walked to the table he pointed out, placed touching the stage with one solitary seat on it. This was a really interesting place, I'd definitely come up this way more often - and hey, they had cocktails!

By the time the show started I was already at the bottom end of my third (Number one, a coffee martini, number two, a Pina Colada, number three, mojito) and as I'd drunk them fairly quickly I was at least a little bit tipsy. I was snapped out of this stupor by the show's start. Aerosmith started blaring on the sound system - I spotted beardy-flannel-guy playing the guitar in the background - and Ragdoll came cartwheeling on. Oh, and I say Aerosmith, don't worry, she wasn't so cliché. She came on to the song 'Ragdoll' which I'm guessing was a favourite of hers. After a few more impressive flips she landed with hardly a noise, graceful and light footed, in a bright white spotlight. It flattered her, it really did, she was absolutely 'sickening', as they say. Her make-up was similar to the advert, but her hair was streaks of bubblegum blue and pink, and she wore a tight red mini-dress that shone under the light, latex maybe. Along with this she had black, elbow length, fingerless gloves of a similar material although far more matte - it didn't shine but it hugged her slender arms - and thigh high white cotton socks, with cute little black bows. The contrast completed the outfit, especially when those socks were slipped into black seven-inch platform heels. Her legs, her arms, her body - the ensemble was gorgeous, and I found myself questioning my sexuality. Surely this was supposed to go the other way round? Regardless, I settled down into my mojito as she began her show.

"Ladies and gentlemen, intersex, omnisex, drag queens and kings: welcome to my show, so graciously sponsored by my Glaswegian friend in the unflattering flannel over there" she said, indicating the beardy-flannel-guy with a chuckle and a flick of her head. She proceeded to ask how everyone was feeling tonight, everyone was feeling a variety of 'woo!', 'yeah!', and a few who were feeling a little 'AAAAHHH!'. I for myself was very woo, though drunk me was tempted to yell horny. "Well you know what else you are?" she asked the slavering crowd "You're all beautiful!" I've got to admit I was jealous. No they weren't. There was a particularly ugly looking bear in the back - oh shit, I thought, I bet she likes bears. Or at the very least otters.

"So, I'm guessing I've got a big gay crowd in tonight!" a big cheer went up "What the devil are you doing perving on an innocent gurl like me?" she gasped, feigning shock, with a wink at the crowd. I blushed into my drink. "Nah, I'm kidding, I'm kidding! Unless you're not, then call me. No, but seriously, very big gay crowd. So you might get me when I say this: what the fuck is up with us and labels? Bear, Twink, Twunk, Otter, etcetera etcetera. For a group of people who hate being labelled, we fucking love labels, right?" She was funny, she was as likeable as she was hot. "and why bear, why otter? Do we want people to think gay marriage leads to bestiality, come on guys! And what the devil is a Twink!" she was a crowd pleaser, that much was certain. After telling a few jokes she gave us a lovely rendition of 'I want to break free' by Queen and a certain Lady Gaga's 'Boys Boys Boys'. She was the one singing, and she had an excellent voice. Great breath control. Naturally, whatever she did in the show, I somehow related to sex: something which was very easy when she started dancing on my table - I could see up her skirt! She was wearing cute heart-stamped white panties, that concealed all due to expert tucking; this really confused my boner.

By the end of the show, that confused boner had swollen and stayed firm. It knew what it wanted, even if I didn't. The audience clapped, and went on its way as closing time neared. Some people remained behind in dribbles as they finished their drinks, and then went off. I stayed sipping my sixth drink (a Capirinha) and beardy-flannel-guy came up and tapped me on the shoulder.

"I'm sorry dude, I've got to rush off. Could you tell Lewis to lock up when he's done?" I just nodded mutely, and he ran out. But who the fuck was Lewis? I was left alone on my table by the stage, reluctant to leave my drink and go back out into the cold. My glass was half empty when I got a reward for my indecision. Ragdoll came out onto the stage, completely in her drag outfit. I stood up, and was about to start some sort of apology but she interrupted me:

"Oh hey, sorry!" she said, smiling "I didn't realise any customers were still here! Hey, did Adam rush off?"

"Adam?" I asked, dumbfounded I was talking to the beauty.

"Yeah, the scotsman in the flannel?"

"Oh right, yeah, he had to dash. Told me to wait here, for Lewis?"

"Of course he did" she sighed "that was mean of him, to leave you here like that. I could have been ages!" Oh! Right! Of course, Ragdoll was Lewis. He was a guy after all, and no doubt a very cute, good looking guy... but a very sexy girl.

"It's no problem, it's cold outside, and I wanted to say thanks for the show anyway, and-" I paused, mid-sentence, a thought suddenly occurring to me "Hey, wait a second, you're still in your drag"

"Oh?" she replied sarcastically "So I am!"

"My point is, why are you still in your drag? Like, what took you so long?" At this point, I could have sworn to any god, she blushed.

"Well, I alwaysgo home in drag, as a symbol of my defiance! As for why it took so long..." she paused, then looked up smirking "I'll have you know I was masturbating" I'll admit it, I took the bait.

"To what?"

"Have you seen how sexily I'm dressed up there?!" she cried "and..." she added, walking towards me "had you seen the cutie in the front row?"

I didn't even have the time to be startled before she locked her red lips with my now less-pale and more-pink pair. I moved my body into hers, an attempt to be the assertive one. I was greeted with the sensation of her dick hardening under the tight red dress, rubbing against my own.

"are you fucking serious?" she moaned with her lips dragging against my face "I literally just got rid of the last boner you gave me." The dirty talk was making me diamond hard, cock throbbing like my lustful heartbeat. I grabbed her round the waist and pulled her in tighter as I drove my tongue into her mouth. This was met with her darting her tongue into my mouth, and leveraging me onto the stage, with her on top of me. I think Ragdoll was a Queen used to her subjects obeying, even though she was generous with them anyway. She had sat up and was grinding her ass on my crotch - the dress had ridden up slightly and the outline of her own impressive dick was moulded by the tight fabric. She wriggled down so she was kneeling in front of me, and unzipped my jeans. My 8 inch dick came flopping out, another half inch off full hardness. She gaped open her mouth, and looked at me, shocked - she was funny even as she was preparing the hottest sex I've ever had. She shrugged her shoulders, and dropped her red lips to the cock. She slid her lips tightly all the way down the shaft - at about half way my head came into contact with her tongue, at the back of her throat, and she bobbed back up again. She then proceeded to bob and lick, moaning as she went, giving me the second best blowjob of my life (after my ex, but right then, he'd left my mind).

She continued to bob her head up and down, as she stroked the lower half as well, kissing her fist every second or so, perfectly synchronising. My dick was feeling thoroughly and pleasurably worked, and I would have been happy to orgasm and die right then, but she came up for a gasp of air. Still stroking me lightly and maintaining perfect eye contact, she groped for her little purse. Reaching it, she pulled it towards her as she gave my cock one or two more licks on the underside. She pulled out a small bottle of lube, and asked me if I was clean. I nodded vigorously, and she started to apply some lube to my already wetted cock. She then raised herself up and pulled down her panties, and lubed up her ass. She stood, and fully removed the panties, then she slid the dress up so I could clearly see her hard cock and flat stomach. It was all clean shaven, her ass too, and she slowly and seductively lowered her whole body onto my throbbing dick. She put her hands on my chest, holding me down as she sat in my lap, with my dick squeezed by her surprisingly tight ass. It looked so loose, being completely shaven. My cock was trembling, and I was worried she wouldn't cum, so I reached out my hand and started stroking her - she smiled, and started getting into a bouncing motion in time with my strokes, but then she grabbed me hand away and placed a finger in her mouth. She sucked it seductively, then bit it lightly.

"uh-uh-uh, don't you worry about a thing, I've got this under control" she whispered, before going into a wild frenzy, slamming her butt down hard. After a couple of times she let out a hard cry that resounded round the empty bar. I saw her cock shudder as she continued to land on her preferred spot, and glanced to our imaginary audience, somewhat pleased with myself.

"Ugh, do you have a name?" she moaned, a word at a time as she picked up the pace, my cock so near the edge I was shocked I hadn't cum yet.

"Fred" I huffed, sitting up to look at her as she rode my cock. She was still beautiful.

"Aww, fuck Freddie, let me ride your hot cock" she moaned, doing her most excellent impression of a professional whore.

"Ragdoll you beauty, take it, take it all from me."

"Oh, Freddie" she responded. She bucked her hips backwards as she landed on my lap this time, and my cock which had been sailing on edge, sped over a wave into a jet of cummy ecstasy.

"Fuck, Ragdoll, Lewis, fuck." I stuttered as I shock, and sat up. She just pushed me down on my back and rode the wave. She took the cum and continued to pleasure my dick even as it came, hitting my head against her g-spot. After a couple thrusts she came, mostly on me though some hit her dress. She started to clean off her dress - it was a nice dress - and then leant over to lick me clean, laughing and half-apologising. She smiled at me when she was done, then kissed my nose.

"I'd be glad to do a show for you anytime" she laughed "and if you ever wanna go for a coffee with Lewis, I'm sure he'd love to too." I liked both ideas. Maybe I'm bi then, maybe I'm still just gay. It doesn't matter too much to me right now, I'm just happy to have fun with Ragdoll.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Ragdoll

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 53 milliseconds