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I finally take the plunge

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2011-03-24

 I finally take the plunge - a crossdressing story

 

I'd been crossdressing for a few months at this point but I'd never gone outside while dressed in women's clothing. I'd been to the shops once, wearing one of my outfits under my normal male clothes; that's the closest I've ever been but even that gave me an intense thrill. Even under a fairly loose coat, I'm sure people could make out the outline of my breast forms. Since that little trip to the shops had got me so aroused, I was determined to do it properly next time so I decided that the following Friday I would go clubbing in town.
 
Friday came and I'd bought a new outfit just for the occasion. I slipped into my low rise boy shorts (black with white spots and white lacing), tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my C cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd been blessed with an arse that any woman would kill for so I could pull off wearing a skirt this small. The skirt had suspenders which I connected to my stockings. I finished off my outfit by putting on a tight black chiffon top with a scooped neck. I adjusted my breasts so that I got some pretty good cleavage, one that would put most women's to shame.  
 
Next I had to put my make up on. The good thing about having been crossdressing at home in private for so long was that I got a lot of practice putting make up on, so it was no trouble for me to put on some foundation, eye shadow, mascara and lip gloss to make me look that bit more feminine. I had already shaved so all I had to do in this department was pluck a few stray hairs that my razor couldn't get to. I sprayed on some of my best perfume then got my wig out to put on.

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   It was a wavy auburn coloured wig with slight black streaks that reached down to just past my shoulder blades.
 
After this I was done, so I went downstairs and to my front door. I reached for the handle but stopped for a second. I took a deep breath and thought to myself that I was about go outside dressed like a woman, something that I'd never done before. I composed myself, opened the door and stepped out into the outside world. Luckily, it was a warm night so I didn't need to wear a coat and could show off my assets. I spotted the taxi that I'd phoned for earlier and walked over to it. As I got in I could see the taxi driver looking at me through his mirror. He was looking me up and down with lust in his eyes. So far so good I thought to myself. I told the driver where I wanted to go and we set off.
 
On the way there, I noticed the driver kept glancing at me hoping I wouldn't notice. I blushed a little and smiled to myself, apparently I make a hot woman! We arrived at the nightclub about ten minutes later and I got out, paying the taxi driver, then walking over to the entrance. As I got there, the bouncer gazed at me with a look that said he wanted to throw me down and have sex with me right there. Of course he couldn't so he just let into the club and I stepped through the door and into a large building full of drinkers and dancers and pulsing with club music.

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I walked over and sat on a stool by the bar. I was only there for what felt like seconds before a guy strolled on over to me. He looked like he was just a shade under six foot, had an average build and short brown hair. "Hey, can I get you a drink?" he asked me. "Sure. . . " I replied, my heart racing with excitement. He ordered a drink for me and himself and as we sat their drinking, we began to talk. We talked about the usual things, where I'm from, what I do, what I like. After a few more drinks, the conversation eventually took on more of a sexual nature.
 
I told him I wasn't that experienced in sex which he said surprised him as he thought I looked that good that I'd be beating guys off with a stick. I giggled, putting my hand on his leg, which he seemed to like as I could see him grow in his pants. The alcohol was helping me lower my inhibitions and the more I had, the more I flirted with him. We moved onto the dance floor and danced for a bit.

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   After a while, he moved his head in towards mine and whispered into my ear. "So, you wanna go have some fun?". I had a feeling about what he meant so I nodded and he took hold of my hand and led me across the dance floor and towards the male toilets as my heart pounded at the thought of what was about to happen.
 
He opened the door to the toilets and pulled me in to join him. He leaned me against a row of sinks in front of a large mirror and began to kiss slowly up and down my neck, my eyes rolling into the back of my head from the pleasure. He moved up, kissing my cheek as he went along, before moving onto my lips which he gently caressed with his, slowly moving his tongue in and out of my mouth. I returned the favour and allowed my tongue to enter his mouth which gave me great pleasure. After a couple of minutes, I broke off the kiss and I think he knew what was coming as I knelt down on the floor and seductively licked my lips.
 
I reached over, unzipped his fly and carefully pulled out his penis. It was pretty big even though it wasn't even fully erect yet, about five inches I'd say. I leaned forward and started licking and sucking down the side of his shaft as I heard a soft moan. I slowly moved back towards the tip which I licked around in circles a few times before I couldn't wait any longer and finally put my lips over the head of his penis and began to suck his shaft down towards the back of my throat. I started off going about halfway before moving back to the tip while stroking the rest of his penis. I continued to bob my head up and down his uncut penis for another minute or two before I got the courage to start deep throating, gradually moving my mouth all the way down to the base of his penis so the top was touching the back of my throat and my mouth was touching his crotch.
 
He began to moan loudly as I fought the gag reflex for a second or two.

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   It calmed down and I stayed in that position for a good ten seconds before I gently drew back along the length of his shaft and allowed it to leave my mouth with a slight popping sound. I looked up at him with a cheeky grin on my face. "You like that?" I asked while stroking him off. A low groan was all he could reply with but it answered my question well enough. "I thought so".
 
My attention was then drawn to his balls, which were smooth and completely hairless. I leaned in towards them and, while continuing to stroke his manhood, took one of his balls into my mouth and set about rolling it back and forth over my tongue. I kept sucking on his ball for another minute before I let it slip out of my mouth. I could see by the look on his face that he was disappointed I'd stopped but he wouldn't be for long as I stopped stroking his now fully erect penis and instead pointed it towards my mouth and took the entire length in straight away this time.
 
I moved my mouth up and down his throbbing member, each time taking it in all the way to the back of my throat before withdrawing so far that only my lips and tip of my tongue were touching it. After a while, he gently put his hands on my head and began to slowly push downwards each time I was going down on him. I took this as a sign he was getting close and I increased the speed of my sucking to which he responded with louder moans. As I stepped up the speed further, his moans got even louder and more frequent. I could tell he was on the verge of an orgasm so I started sucking as fast as I could, deep throating each time. Very quickly his hold of my head got tighter, his legs started to tremble and his manhood quivered as he orgasmed in my mouth.

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He came in large spurts, each one hitting the back of my throat, giving me no choice but to swallow. He slowed down after another few squirts and, thinking he'd finished, I pulled his slowly softening penis out of my mouth when he unexpectedly squirted two more jets of warm cum, one onto each cheek. I was taken aback for a few seconds as I wasn't expecting it, but then I ran my fingers along each cheek and licked off the stray cum before swallowing it with a smile. He was breathing heavily now, clearly exhausted from an intense orgasm.
 
"God, that's the best blowjob I've had in ages. " he said, in between his deep breaths. I was pretty shocked at his comment; before tonight, I had never even done anything with a guy before. Sure I'd fantasised about it and practiced with toys, but I'd never had the real thing and here he was saying that the first blowjob I'd ever given was one of the best he'd had in ages!
 
"There's more to come yet. " I replied playfully as I got to my feet and leaned over the nearby sinks. I hiked up my skirt and pulled down my underwear just a little bit, sticking my arse out seductively. He took the hint pretty quickly and strolled over to my waiting arse with a grin across his face. I could see by his reflection in the mirror that he was already getting hard again just at the thought of having anal sex with me.
 
I'd tried using a dildo anally at home, it was about the same size as the real thing that I'd just been sucking on. Even with lube, I only ever managed to get it in just past halfway. I was so caught up in the moment of having my first time with a guy that I was about to try taking the whole thing without anything to make it slide in easier and I didn't care!
 
I braced myself on the sinks as he held his growing manhood and probed around the outside of my hole teasing me while I grew even more aroused.

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   I couldn't wait much longer so I backed into him to show that I wanted him to give it to me now. He duly obliged and slowly started pushing into my hole and my legs began to tremble. He kept pushing further, eventually getting in further than I had managed with a dildo which is when it started to hurt. I think he could see it was starting to hurt me because he forced in the last couple of inches to get it over with. There was a sharp pain for a few seconds but this was quickly replaced by an amazing feeling as his cock was inside me.
 
He started thrusting, slowly at first, allowing me to get used to the feeling. He quickly sped up as he got hold of my hips and increased the force of his thrusts. His balls were slapping against my arse with each thrust and I couldn't believe how much hotter his made me. We were both moaning with pleasure, I'd never experienced this much bliss before now. I started backing into him each time he thrusted to increase the force and this nearly put me over the edge. I was so close to cumming that I had to slow down and only back into him every few thrusts.
 
He moved his hands to my breasts while still pounding me. It was a good thing I'd spared no expense with my breasts forms as he went to town on them, grabbing them with some force. I pretended to moan with pleasure at his treatment of my breasts which seemed to please him. He started to use my breasts as leverage, pulling on them with each thrust to add more force.

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   It hurt the first few times before a feeling of pleasure again over powered any pain I was feeling.
 
The pounding he was giving me got to its fastest yet and his moans the loudest and I guessed he was getting close to cumming inside me for the second time. He moved his hands back to my hips and I started backing into him hard with each thrust to help him over the edge. Within seconds, his grip on me tightened, he gave a loud moan and I could feel him start to fill me up with his cum as large amounts of his seed flooded me with each thrust. This pushed me over the edge and I had one of the best orgasms ever, shooting stream after stream and my legs almost collapsed from the intense pleasure. It was a good thing I was over a sink and my cum landed there otherwise he might just have suspected something!
 
We both stayed like that for a couple of minutes panting heavily, exhausted from the powerful orgasms we both just had. I could feel him slowly softening inside me and, before long, he gently slid out of me and we could both finally regain our composure. He had shot so much of his sperm into me that I could feel it running out of my hole and down my legs. I pulled my underwear up so I could keep the juices inside me and wiped up what had leaked out with my finger and licked it off. It seemed to taste better after being inside me, maybe it was because it was a stronger orgasm than when I had sucked him off.
 
I adjusted myself as he'd pounded me so hard, my breasts had nearly fallen out of my bra. I neatened my hair a little and, as I turned around, he was zipping his fly back up. He leaned in and kissed me on the lips while grabbing my arse. He then stopped kissing me to say, "That was the best sex I've had since I can remember. You've got some talent.

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  "
 
"I'm glad you enjoyed it. " I said, blushing as he flattered me once again. "Shall we go back then" I asked, glancing towards the door leading to the dance floor. He agreed and he led me out of the toilets and to the bar area. We had a few more drinks and danced for a while when he said he had to leave. "Give me a call sometime. " he said to me as he handed me his phone number. I nodded and we left it at that. I didn't stay much longer after that having had more pleasure than I'd expected before I came out tonight.
 
I arrived home at about 3am and it didn't take me long to fall asleep, dreaming about what I'd experienced that night. I was sore for a couple of days after that but it was well worth it as I had some of the best sex I'd ever had; I never expected I'd enjoy it with a guy so much. I decided that this would definitely not be the only time I did this and planned to make it a weekly thing.

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