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Attracting some attention

"A night out catches the eyes of a stranger"

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Like most people in their late teens and early twenties, I enjoyed going out to pubs and clubs. I would go out with my friends and my girlfriend, always in guy mode. I was still in the closet pretty much back then. I would dress up at home when I was alone, never venturing further than the back garden to have a sneaky cigarette in the cool evening air, but that was as far as I ever got.

I would watch my girlfriend getting ready before we would go out and always feel a little touch of jealousy as she applied her make up, did her hair, and pulled on a sexy dress and heels. I'd always wanted to dress up and go out.

A friend of mine who knew about my dressing had suggested a few things but I'd never been able to do it. He was gay and into the fetish scene, and always said I should go to this club or that club with him, just us two, but I never did.

Then an opportunity arose. I used to work as an area trainer for a national retail store and they needed me for a new store opening. This wasn't really unusual, however they needed me there for two weeks instead of the normal one.

When the details were sent to me I found I'd been booked into a hotel as normal but because of some error I had not been booked in for the Saturday night. I decided to pay for the extra night myself but couldn't get one in the same hotel so had to choose another, for one night only, and that was enough to get me thinking. Staying in one hotel for two weeks and being dressed for one night was a little obvious, but a single night in a different hotel would be ideal.

When it came to packing I swear I had a suitcase for my stay and then a whole other suitcase with lingerie, shoes, dresses, and make up! Every time I thought about it I wanted to wear a different outfit, so I figured I would take everything and take everything I did.

Work for that first week was a long and tedious experience, and I was so excited on Saturday as I checked out of my first hotel and drove to the second. I arrived and checked in with little fanfare and, upon arriving in my room, I set about deciding what to wear; little black dresses, corsets, mini skirts, long dresses, short dresses... over the years my collection had certainly built up!

Then I saw something I'd bought myself but had never worn. It was red, bright red, and a beautiful soft satin, fitted pencil dress, almost retro in styling. I think I'd been watching too many Marilyn Monroe films when I bought it but seeing it then I knew it had to be worn for my first time out.

From there the outfit put itself together; the red basque, the matching satin panties, the lace top stocking, the high heels, the cherry red lipstick with smokey eye shadow, the curly hair. I savored every minute of preparation and over the years had mastered the art of crossdressing. Hair and make up learned from various places, how to walk, how to talk, even the best way to... erm... tuck everything away.

I felt fabulous as I looked in the mirror. The basque cinched my waist while the breast inserts gave me just a hint of cleavage. My hair cascaded over my shoulders in full dark curls. My long legs covered in their nylon finery.

I had done a search online and found a bar nearby that seemed like it would be busy. The more people the less I would stand out, although looking the way I did it was hard not to stand out! I called for a taxi and headed to my destination, nervous excitement running through my body.

As soon as I got there I went to the bar and ordered a wine. It was busy, and while I turned a few heads the world didn't come juddering to a halt, so I felt a little more relaxed. I walked outside to the smoking area with my drink and stood alone. This lasted about three minutes. As anyone who smokes knows the best place to make a friend is in the smoking area at ten o'clock on a Saturday night.

Three women approached me and asked about my dress and my shoes and how I did my hair. I was overwhelmed by these slightly drunken inquiries and couldn't help but feel self conscious as they took me apart with their questions.

At one point someone mentioned my voice and I thought I had given myself away, however they were simply noticing my southern accent standing out. I finished my wine and my cigarette and decided I would head back to the hotel so as not to push my luck too much. As I went to leave the women all protested. It was someone's leaving party and I just had to go to the club with them. I decided to stay a little longer. A little longer turned in to more wine, more talking, more laughing.

Later that night I found myself in a club, a little drunk, dancing with the girls, boys, and whoever was nearby. A few guys had groped my bum and tried it on with me. While I turned them down I'm not ashamed to say I enjoyed the attention.

What surprised me, however, was one of the girls I was there with. Hannah was incredibly pretty, not over the top, mid-twenties, brown hair, very petite. Over the evening she'd become quite attached to me, dancing when I danced, smoking when I did and so on.

We talked a lot and she told me about her work and her boyfriend and many other normal conversation points. It was during one of these conversations when, while in a quiet corner of the smoking area, I felt a hand on my bottom.

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I turned to shoo it away and found it to be Hannah's hand. I looked at her a little surprised and she sheepishly took her hand back. As she mumbled an apology I took her hand in mine and guided it to my side, running it down to my hip.

"Isn't satin just so sensual?" I smiled at her. Her eyes lit up as she pulled herself closer to me. She looked around us quickly to see if anyone was looking and stole a quick kiss. For the briefest of seconds our lips met. A spark between us.

"Let's go fix our make up," she whispered as she took my hand.

I tried to protest, to explain that I wasn't quite as I appeared, but she was already leading me inside, across the noisy club and into the ladies toilets. I was still trying to explain as she pulled me into one of the empty cubicles with her and locked the door. I think I got as far as, "There's something you should know," before our lips met again.

Her tongue hungrily sought out mine as she pressed her body against me. I kissed her back, my hands holding her to me. I was lost in the moment, that passionate embrace. I didn't even notice her hands run down my back, or her fingers as they lifted the back of my dress. By the time I felt her hands on the bare skin of my backside I was so turned on I didn't want her to stop.

I kissed her harder as I wrapped one of my stockinged legs around her. Her hand moved up from my bottom and traced the line of my basque around to my stomach. I could feel her fingers caressing the soft satin and lace fabric of my lingerie as she moved down further. Her fingers danced down to the soft fabric of my panties.

I knew I should stop her but I just wanted her to carry on, and carry on she did. Down between my legs where her fingers stopped. She stopped kissing me and looked my in the eye. The confusion in her face as her fingers found not soft and wet but expertly tucked away, my cock.

"... is that...?" she looked at me a little shocked.

"I'm so sorry, I tried to stop you but then..." I began to blurt out.

"Do you have a...?" A moment of silence passed between us. She'd taken a step back away from me and was watching me. I tried to start explaining again when she waved me silent.

"Show me," she said sternly.

"Pardon?"

"Lift up your dress." At that point I didn't know what to do other than to do as she said. I lifted my dress up to just above my waist. Looking down I could see where, despite my best attempts at tucking back, there was a noticeable bulge in the soft fabric of my panties.

Before I knew what was happening Hannah was crouching in front of me as she pulled my thong down to my knees and my cock sprang free. For a moment I stood there, terrified. What would she do? I should have told her. I waited for her to react for what seemed like forever when suddenly.

"Oh wow!" she whispered, a split second later I felt her warm lips envelop the head of my cock. The surprise almost made me lose balance as I teetered on my high heels. I rapidly hardened as her tongue worked it's way over me, guiding me into her mouth and down her throat.

As she knelt there she ran her hands over my stockinged legs, over my bottom, tugging at my suspender straps as if to pull me further into her throat. She pushed her mouth as far as she could down the length of my hard cock before falling back breathlessly. She looked up at me.

"Oh my god! Fuck me now!" She sprang to her knees and lifted her skirt, bending over as she did so. No panties! I could see her wet pussy glistening between her legs as she presented herself to me. My cock, wet from her saliva, stood proudly as I stepped behind her.

I pressed the tip of my hardness against her wet hole and slid inside her with one fluid motion. Her pussy wrapped around me, hot and wet. I began to fuck her, slowly and purposefully. In less than a minute I fell her spasm beneath me as her pussy flooded with her orgasm. Breathlessly she fell forward, stumbling to keep her balance.

"Sorry, I cum really fast when I'm horny." She looked back at me, my long dark curly hair pulled forward over one shoulder, my dress hitched up, panties now around one ankle, and my hard cock glistening with her wetness. "I need you to feed me!" she said as she positioned herself on the toilet in front of me.

She spread her legs wide and with one hand began teasing her clit. With the other she reached out to my cock and guided me into her mouth. Her hand worked the length of my cock as her mouth sucked hungrily on me. In no time I felt my cock swell inside her as I breathlessly said I was about to cum I heard her muffled squeal of pleasure as she brought herself to orgasm. I filled her mouth with cum and she swallowed every last drop.

We waited a little while to gather ourselves before re-entering the club. No one had even noticed we were gone and soon it was time to head our separate ways. Hannah and I exchanged numbers for if I was ever in the area again. In the taxi on the way home the cabbie asked if I'd had a good night. Right at that moment a text from Hannah came through.

"Fancy a night cap?" it read.

"I'd say it's going to go beyond good."

Published 
Written by Jess_cd
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