A Dare Gone Right

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Dildo shopping in a thin summer dress.
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'Well, Paul, if you're not man enough, just say so!'

'Come on, that's not fair, Isabel. I've never dared you to do anything this risky,' I replied.

'Oh yeah? Walking around the mall in a pink latex micro-skirt and no panties wasn't risky? My balls were swinging around for all to see!'

'Yeah, but it wasn't entirely out of character for you. And nobody did see - I stood behind you on the escalator to preserve your dignity. Besides, you loved it - you practically sprayed the roof lining of my car with cum when we got back to the parking lot.'

Isabel sighed, 'That's the point, Paul. I guarantee you that this will be such a turn-on, you will remember it for the rest of your life.'

And that's how I - Paul Lanson, a hetero (although you might disagree), sporty, musical, A4 kind of guy - came to be sitting in the passenger seat of Isabel's car five days later, checking out my makeup in the sun-visor mirror, before the fright and the adventure of a lifetime.

Now's probably the time for a little background. I'm 32, mostly-retired from IT, and play guitar in a moderately successful rock band. Isabel is 28, and if you haven't worked it out, a transexual. She's also smart, funny, tall, pretty and slender, with cafe-au-lait skin, dark brown eyes and fair hair. And, since the whole point of this story is to turn you readers on by sharing the details, I may as well tell you that she's also got a smooth, fat, seven-inch cock which is always either begging for attention or standing to attention. One thing it never does is refuse attention, which keeps me conscious that if I don't satisfy Isabel, someone else will. And that ain't gonna happen on my watch, because I am in L.O.V.E.

So, back to the car, 7.15 last Saturday evening. During the past five days, Isabel had waxed me, shaved me, spray-on-tanned me, dressed me, undressed me... my cock had been leaking almost constantly with all the attention, but she had me on a strict no-orgasm regime. That hadn't stopped her from cumming in my mouth three times during that period, which didn't exactly help to make me less horny. But the thing that turned me on the most was seeing myself in the full-length mirror at home when she was finished with me. I don't like to brag, but I was... well, a knockout. Not as pretty as Isabel, of course, but well up to my own standards of what to look for in a woman. We (well, Isabel) decided against a padded bra - she figured that as the whole point was a humiliation kick, I shouldn't be too convincing. The effect we were after was slutty transvestite rather than beautiful shemale, she said. I was too horny to argue.

We went over the details of my little 'assignment' one last time, then Isabel wished me luck and I got out of the car. I had to walk for about two minutes to get there. I was wearing a thin, strappy mini-dress in flimsy material, but figure-hugging enough that a gust of wind wouldn't cause any drama. On my feet, which luckily are quite small, I had medium heels which showed off my red-painted toes, and tightened and toned my calves. Apart from that: nothing. No knickers, no stockings, no nothing. I could feel my ballsack tightening in response to the cool air. I received a few stares from guys, but although I blushed, I didn't feel threatened. I know I've got high standards when it comes to women, and I knew I looked hot, if not totally convincing. (The 'convincing' part is, women will be surprised to learn, less important than the 'hot' part for most guys.)

Anyway, I finally got to my destination - a sex shop in the middle of a run-down, boarded-up street. Isabel and I had been there a few times before. They sell the usual stuff, plus a wide range of DVDs, like a porno Blockbusters. I looked around to see if I could spot Isabel's car, but she was gone. I took a breath and entered.

I was beginning to think that this wasn't going to be much of a challenge. Do the things on my mental list, pay, get the hell out and never go back. Shit, even if I did go back as a guy, they'd never recognise me.

The shop was empty, as it was nearly closing time. There was a youngish guy behind the counter, reading a book. He didn't acknowledge me - discretion is the order of the day in these places.

The items on the list Isabel had given me were chosen for maximum embarrassment potential. Number one was a DVD featuring my favourite shemale performer. The section I wanted was at the opposite end of the shop from the guy at the counter - good for me. I walked over and, since the section I wanted was on the bottom two shelves, I bent down to see. My first big mistake. Since I bent over at the waist, and since my legs were slightly apart, my tiny dress was pulled up right over my ass. If the assistant was watching, he had now had a full view of two tanned asscheeks, a pair of dangling balls and very likely a shaved asshole too. I straightened quickly and looked behind me. He was still engrossed in his book - maybe he was acting, but I hoped I'd got away with it.

I now squatted down in the appropriate ladylike fashion and continued looking. I found what I was looking for, and that's when I made my second mistake. The cover of the DVD in question was a montage of this dreamy T-girl in different poses - one showing her perfect tits, one with a close-up of her asshole and balls, and in the middle, a picture of her cock just after cumming, her foreskin and fingers a glistening mess of thick sperm. As you can probably tell from my detailed description, I lingered a little too long on these images, with the predictable result that a five-day orgasm ban will bring. I was hard as a rock, in the flimsiest cotton mini-dress you can imagine. And there was nothing in my line of sight that could distract me from thoughts of sex. I tried staring at the carpet, but getting rid of this hard-on was going to require a few minutes' concentration, and if you stare at a carpet for that long, people tend to ask if there is anything the matter.

The shop assistant walked behind me now and I heard him turning over the 'closed' sign in the window.

'I'll have to lock up in fifteen minutes, miss,' he said.

I decided I would just have to brave it out. This erection wasn't going anywhere - in fact, I was beginning to suspect that Isabel had spiked that beer before we left with Viagra. (It doesn't spoil anything at this stage of the story to tell you that this was in fact exactly what she had done.) I figured I could hold the DVD in front of my crotch when I stood up.

Next on the list was a huge black dildo with a suction cup. It was in a large box which would come in handy for covering my erection, so I took it and walked over to where I saw the final item, a fat buttplug with a horse's tail kind of thing attached, right in front and to the side of the counter. It was high up, on a rack near the ceiling, and I had to put my other purchases on the floor in order to have my hands free. This time I managed to squat in a ladylike fashion, but I wasn't to be spared further embarrassment - in fact the worst was to come. I had to use both hands to unhook the box from the rack, and since it was so high up, I had to stand on tiptoe and stretch my arms up. The girls among my readers will know that this is a no-no. My dress was lifted up by my shoulders, and the hem came up and over the head of my cock. I quickly brought the box down, lowering my dress again, but although my ass was covered my cock was standing stiffly and stubbornly uncovered, the front hem draped over its base. Worse still, in my haste I had dislodged the other boxes up there on the display rack, and if I were to lower my box to the floor and rearrange myself, the whole lot would come crashing down. Burning red with shame, I just had to stretch my arms up again, repeating the whole sorry process, and for longer this time as I had to make sure all the boxes were properly balanced before I let go.

I now knew without any doubt whatsoever that the shop assistant must have seen it all. He was three, four meters away from a practically naked, hot 'chick' who had nearly demolished his shop - how could he not notice? Sweating and hot, I gathered my purchases and put them on the counter in front of him. I tried to avoid his eye, but he smiled at me and said,

'I'm sorry I didn't come to your aid a moment ago, miss, but I was kind of, ahm, uncovered myself...'

He then pushed back his stool and I saw that his pants were around his ankles and his cock was as hard as mine. It was clear that he had figured that since a horny T-bitch had flashed everything she had in his shop, it was perfectly OK for him to drop his pants too and give his cock a crafty stroke behind the counter. And he probably thought, not knowing that I'm straight, that I was now ready for some action. Uh-oh.

He stood up, kicking his pants and shoes off, and looked straight at me as he slowly stroked himself. I found myself looking at his cock as his hand moved up and down. Not at him, just his cock. And the smooth golden skin of his belly behind it. And his shaved ballsack, hanging low in the heat of the shop, swinging lazily backwards and forwards. And then I found myself guided by my own cock, moving around the counter and getting to my knees. He tasted of sweat and his cockhead was slippery with precum. I had barely got started when he flicked a switch behind the counter and the lights went out. He pulled me gently up and went to lock the door. Then he guided me through a door and into an office, where he pulled my dress off over my head and motioned for me to get down on my knees again. I was ready for that cock in my mouth again, so I didn't hesitate. But he moved behind me, and, pushing me forward onto my elbows, stuck his tongue into my asshole without me even feeling his breath on me first. I gasped and he slid his tongue in and out of me as he tugged gently on my balls. I looked underneath me and saw that a string of precum connected my cock and the cool linoleum floor. He then got into a position that told me he intended to fuck me. I breathed,

'Condom!'

'Relax, I've got it,' he said, and waved a packet under my nose. I heard him rip it and put it on, and for my own peace of mind I reached under my balls to feel the rubber with my fingers just as I felt it prodding against my ring. Now, I had never been fucked before, so you might think my attitude at this point was surprisingly nonchalant. But I have experimented with fingers, dildos, vegetables and the like, as I'm sure most guys have (even if they don't admit it) so I knew I could handle it. What I wasn't ready for was just how the mental component of all this was affecting my libido - the taboo nature of it, the 'But I don't even like guys!' going through my head made me hornier than I have ever been in my life.

He had made me wet with his tongue, and I think the condom must have been lubed, because he slid into me with no trouble. He got the angle right after a few strokes, rubbing my prostate on the way in and the way out, and I looked under me just in time to see my cock lurch and spit out a big glob of thick cum. Fuck, I was horny - I supported myself on one arm and, reaching under, scooped it up; then, just as I was transferring it to my mouth, a light came on and the cock in my ass stopped moving.

Someone behind, a man, started laughing uncontrollably. Then:

'Hey, little brother - you finally got yourself some action?'

Some kind of hand signals must have been exchanged, because without further talk, my guy behind me started fucking again, and his brother came into view, unbuckling his belt as he walked. Shit. I wasn't in the position to call any of the shots now - I'd just have to go along with it and try to get out of there in one piece. Where the first guy had been more like an awkward teenager, this guy seemed mean by the way he looked at me. He sat on the floor and positioned his cock right under my mouth.

'Suck, bitch.'

I knew he didn't want any backchat, so I took him into my mouth. His cock was soft, and didn't respond to the simple fact of just being in my mouth, so I had to use my hand to pull back his foreskin while I licked at the head, teasing and tickling. He grew quickly then, but it was more girth than length. I quickly got over my fear and before long all I was aware of was the cock in my ass, the cock in my mouth and my own cock, which was almost buzzing with a pent-up need to cum. Suddenly, I felt the cock behind me slide out and heard the snap as he removed the condom. I then felt the guy in my mouth pull out of me and opened my eyes just in time to see the first guy jerking his cock an inch from my mouth. Stretching my neck, I clamped my lips around the head of it just in time to feel the first ribbon of cum slide across my tongue. It seemed hot - hotter than his cock, is that possible? - and so thick that when the rest of it came, in wave after wave, I felt that I could almost differentiate each strand, each spurt, from the others. He just came and came, and when he slowed and began to pull away from me, I tipped my head up so that I could keep it all in.

I was so fucking horny now that I had in mind to swallow it slowly, savouring the taste while this other guy fucked me, as he was sure to do. But I was forced to reconsider quickly when guy number two's cock was suddenly pressed against my lips again, so I swallowed hard and opened up. No more deep-throating for me, though - his hand was a blur, and all I could do was get the tip of it between my lips, feeling his foreskin bunch up and retract while I waited for seconds. I didn't have to wait long, but he pulled away from me - he didn't want my faggot mouth around his cock, he wanted to cum on my face. Good enough for me. I opened my mouth wide anyway, and managed to catch a couple of spurts, while most of it ended up on my forehead and cheek. He wiped himself off on my chin, and as soon as he had finished I scooped up what I could of his seed from my face and slurped it off my fingers. He shook his head in mock disbelief, and as I rose to my knees, he said,

'If you like cum so much, you'd better clean up the mess you made.'

I looked down at what was an unbelievable amount of cum on the floor underneath where my cock had been. I must have been leaking like a rusty tap the whole time I was being fucked. He grabbed my hair and pushed me down. I didn't need any forcing - my cock was still as stiff as a flagpole, and I could have drunk a football team dry. I sucked and slurped at that floor like the dirty tramp I had become, the remains of my makeup becoming a smear in the process. The older guy walked out with a grunt, picking up his pants on the way. My first guy handed me my dress, led me to the door and let me out, without a further word.

I walked down the street, so dizzy with horniness that I didn't care if my Viagra-reinforced erection waving to and fro under my dress caused a riot. Luckily, I saw Isabel getting out of the car and running towards me. She mistook my cum-streaked face for tears and thought I'd been beaten up. She'd been waiting for half an hour and was worried sick. But when she came closer she saw that I was grinning, and when she hugged me in relief, she smelt my face and hair and the penny started to drop.

'Get me home,' I said. 'You, my darling, are going to give me my fourth cum-load of this delicious evening, and after that I'll be lucky if I even get the tip of my cock inside that fabulous ass of yours before I explode like Niagara'

'I think you mean... Vi-agra,' she said, flashing me the naughtiest of smiles.

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AnonymousAnonymousover 4 years ago
Love them dares

Very sexy story, please write more on this subject

AnonymousAnonymousabout 6 years ago
Heels

You can put makeup , dress, lipstick and low cut blouse on a male, nothing happens! Add heels , "he's a hot bitch "!

MonicaCDMonicaCDover 9 years ago
HOT HOT HOT

I recently visited an adult store in drag for the first time. The clerk was hitting on me but I was too scared to respond. Wish I had now, then I could of had some hot cock too. Next time I go I am getting fucked for sure!!!!!!!

AnonymousAnonymousalmost 11 years ago
More stories please

This story was so hot -- I came in my hand and ate it all up !!! Please tell more stories. I can't wait !!!

AnonymousAnonymousalmost 12 years ago
HOT

made me so horny i had to strip naked and stroke my hard cock. I came all over myself, wish 2 guys would fuck me

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