The Hot Pink Mini Skirt

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Guy in a hot pink mini hooks up with NYU Drama Queen.
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I sat panting. My cock was limp and covered in cum. Alex was lying next to me lightly chewing on my ear. I could feel her body, spooned on my backside, breath going in and out. Her semi hard cock danced about my slick hairless ass. She purred in my ear, "I am so happy to have brought you home tonight."

It was funny, there was no guilt. There was no shame. I was happy as I lay beside this sex kitten. My skirt, the PVC leather one that barely covered my ass was still hiked up on my hips. It was my first night with another transvestite. It was the first time I had anal sex. It was the first time I had given a blow job to a transvestite and had her cum in my mouth and on my face.

We have all read about nights like this, those of us who read stories about cross dressing. I was out of town at a conference for a week. I left my girlfriend behind. I also drove 5 hours to avoid the risk of security checking my bag full of feminine clothing. After arriving at a midtown hotel, I had unpacked. I had plans for the first night in the city as it was a Saturday. I had brought clothing for a night out, the plan being to go out on my own to a TV bar dressed in some really sexy clothing. I brought my favorite pink PVC mini skirt, garters, a black vinyl corset, nylons and red thigh high fuck me boots. I had some make up and an old pink party wig, but also planned to visit a boutique I located on line prior to the conference.

The night started there, at the boutique where I bought a new black haired wig in kind of a gothic style. I had brought all my clothing in a back pack and got dressed at the boutique. I had an 8:00 p.m. appointment for a makeover, and had my make up done by Denise, a girl/girl who knew what she was doing. To me after the make up, I looked hot; at least at the time in the mirror at the store.

I was twenty nine years old and had fantasized about going out dressed all my adult life. I assume I was bi-sexual, but had only had sex with a guy once the summer before. I had been on a phone sex hook up line, driving around wearing a pair of satin panties one Saturday afternoon. My live hook up request had been something like, "good looking guy, trim, 150lbs, 5'10", 6" cut, who likes to wear panties and is bi-curious. Wants to chat or hook up." A guy had come on live to talk to me and after we talked I agreed to stop by his street level apartment. He asked me if I had a pair of panties for him to wear. I told him I did as I had just stopped and bought a few pairs.

I walked into the apartment to find a muscular guy with short hair. He told me he had never worn panties, but I sounded nice, attractive and he was willing to give it a try. He locked the door and undressed, asking me if I brought the pair of panties I wanted him to wear. It was a bit awkward but I had worked myself up in the car so much that there was no stopping me. I shyly handed a brown pair of silk and spandex panties to him from my shorts pocket. He put them on quickly. I stared down at his cock outlined and hard in the tight shiny material. It looked like something from a panty boy site I guess and it did turn me on.

The man began to unbuckle my belt. I let him. He found that I was wearing a tight light blue pair of silky panties with frill. A wet spot marked the tip of my cock. I could see him start to lick my cock through the panties in a mirror. My slender body looked good in the panties I thought. I had such little body hair, and straight silky brown hair on my head. I saw myself as effeminate for the first time that day. He pulled my cock out of the panties. It was slick with pre-cum and moist from his lips. When he began to suck on me the sensation was too much. I came quickly. I assume it was a bit of a let down for him and was embarrassed.

He let me play with his cock through the panties I had given him. I took it out and had tried to give him a blow job. I was nervous and uncomfortable though. After a bit he pulled back and began to masturbate. He came into the air, some landing on my chest, as I stood still.

On this occasion I had felt huge amounts of shame. I was on my way to a bachelor party that night and felt sick to my stomach the entire party. I was not sure how to deal with it. I trashed my entire hidden collection of panties the next morning and stayed away from the internet for months.

So here I was in NYC alone more than a year latter. I arrived at the club about 10:00 p.m., taking a cab from the boutique. I was clearly early because the club down by the lower west side was mostly empty. I had no choice as to where to go after the boutique because it was closing and I was uncomfortable going about town dressed and alone. I did not know the city well. I suppose the cab driver may have guessed what I was up to, but he never let on. I never spoke other than to offer him the address of the club. He addressed me as Miss, commented I looked sexy tonight, and then picked up a cell phone. He talked the whole ride in a foreign language I could not identify.

The guy at the door looked me over and whistled. He let me in without a cover. Heavy techno music played through a loud sound system. Red lights marked a tall bar with red leather bar stools, mostly empty. The floor was concrete. The walls were black. Some red leather booths lined one wall. Another room with lights appeared off the side of the room I was in. Lights focused on a dance floor in this main room and in the back there was a small stage with mettle polls at various places on the stage like a strip club. A few TG girls walked about but no one approached me immediately. I walked to the bar, my leather boots clicking on the cement. I was getting worked up just being there. I ordered a Captain and coke and a shot of tequila. Then I took a seat at the bar and waited.

The bartender would stop down and talk. He was clearly a gay man, well defined and probably thirtish. He told me the club would not really get hopping until after 11:30. I told him I was from out of town and new to the scene. He did make me fell good when he told me I would do well tonight, dressed like that. He warned me to be careful but have fun. One of the door men stopped by. He wore leather pants and had tattoos on his arms. His tongue was pierced and he had long wild hair tied in a bun. Getting right to the point he told me I was hot, and that he would love to "bump with me." This was a new term, though I assumed it meant he wanted to fuck me. I tried to avoid letting him know I was not sure what he meant. I responded that I was flattered but that I was really into other Tgirls. There is no doubt I enjoyed the attention however.

Alex came in around 11:40. I saw her come through the door. She had tight sequenced mini dress, black stilettos, back nylons with a sharp black stripe up the leg, blond hair, pink Barbie lipstick and looked so convincing I was not sure if she was a girl or guy. She had a group of other girls with her, some of which I could tell were Tgirls, so I guess I was immediately smitten. I was also a few drinks into the night and decided the best way to start an introduction was to send a drink her way. The bartender was down talking to me a few moments later and I asked him if it was OK to send her a drink. He whistled and said I had good taste.

Moments later Alex and I were talking. She told me I looked great. She was out with a group of girls from a sort of Tgirl society. She was at NYU and a drama major. I told her my story in summary that I was in the city alone for the week at a conference. I had arrived that day and immediately gone out shopping. I told her that I was bi curious, inexperienced and attracted specifically to other Tgirls. We talked for a bit and she asked me to dance. She whispered in my ear that she bet I was one hot guy when I was not dressed.

I love my fuck me boots but I cannot walk that well in them. Dancing to techno was a challenge, but I had fun. A slow song came on and I started to walk off the floor but Alex grabbed my hand and pulled me back. She began to sway like we were back in 7th grade. We were about the same height. I loved the feel of her body on mine, the feeling of our pelvis rubbing, of a bulge touching together.

She let her hands wander to my ass. My gaff was straining to contain my cock. I ran my hands on her ass and she gasped a bit in my ear. I began to kiss her neck. A strange feeling kissing a guy dressed as a girl that you know is a guy but who looks like a girl. We were both on fire. A new fast song came on but we kept our embrace for a bit, panting.

We found a booth in the corner, allowing for some heavy petting and more kissing. Her legs were curled up on the bench seat, her body facing me, leaning into me, with the legs behind her. This left her dress hiked up a bit and her crotch slightly exposed. I rubbed her cock under her dress, running my hands up her nylons on the inner thigh. Her cock felt so smooth and small through her panties and nylons. Her eyes watered as she looked at me. I remember thinking she was beautiful no matter what she was.

She finally asked me if I wanted to leave and have some more fun in private. We discussed briefly going back to her house, and I tried to make her feel safe even thought it did not seem to be a concern at that moment to Alex. Honestly, I was so ready to go. I had never been that ready. The feelings I was having made anticipation of straight sex with a high school girl seem boring. I wanted to get into her pants as they say, but I also wanted her in mine. I felt like we were equals and both so needy, it turned me on.

We got a cab to her apartment, a 4th floor walk up in Chelsea. She kicked off her shoes as we entered and through her arms around me. The tiny room had a couch, pillows and that's about all I saw. She whispered in my ear she wanted to fuck me so bad. I told her I needed to suck her first, asking her to cum on my face. I had never spoken this way to a girl. I had never spoken to anyone this way. It felt so free to talk to Alex.

I unzipped her sparkling dress and it fell to the floor by her nylon clad feet. She had the hottest corset I had ever seen around her waist. It was hot pink with black silk ties, and balk silk material outlining the ribbing. Her panties were hard to see under the nylons so I quickly began to peel the nylons down finding hairless legs.

She wore hot pink satin panties, which while I may have loved were quickly ripped aside. I found her gaff and undid it by untying a string on both sides. There I found the most beautiful small cock I had ever seen. It was hairless, and could not have been more than 5". It was cut and straight, smooth as silk.

Only knowing what felt good to me, I licked the shaft from the underside and tongued the tip roughly. I did this for a few minutes, and then easily slide the whole cock into my mouth. Alex took a deep breath and began to shake. I could feel him tense and then his hands came to my head. I held her ass with my hands and pulled her into my mouth. Alex's hands held my head there on his cock. He began to cum. Surprising amounts of cum hit my throat suddenly. I did not gage but I was shocked by the feeling. I felt empowered and so incredibly good at that point, cum entering my throat and falling out of my mouth.

Alex's knees buckled and she fell out of my mouth, her body sinking back on a couch. I looked straight forward at her slick cock, and her face. She had her head back for a moment in ecstasy. I climbed on to of her and kissed her, her cum still on my face. She kissed me back hard, hungry for my tongue. She then rolled me over, and I was on the couch sitting. She pulled up my skirt and down my nylons. She quickly and expertly exposed my cock and dove for it, tonguing the tip and shaft quickly. She darted over it, the warmth of her mouth surrounding me. Her hands found my balls and she lightly, so lightly clutched them. Her fingers continued to walk to my anus, finger the outer ring. My orgasm grew in my hips, my stomach and my toes. It grew until I was gasping for air and arching my back.

I came in huge torrents. She pulled away and watch cum fly across the room, landing on her dress behind her. I kept spurting and she dove back in, catching some in her mouth and licking the rest as it oozed out of my cock.

She was hard again, after this show. She rolled me onto the floor, on a big pillow. I complied without hesitation. My hot hairless ass was exposed to her. She grabbed a tube of gel from somewhere. She stuck first a finger than a thumb in my ass as I whimpered in delight. Her thumb felt so good in there and she moved it around. I could feel cum still coming up out of my cock but it was hard again as well, rubbing against the silk material of the pillow.

Alex's 5" slender cock entered me in one motion. It was pure pleasure. There was no pain due to its size. She began to fuck me slowly, with smooth short strokes. I realized it was hard to breath in this position a bit. I felt so submissive in this position and loved it. Her speed increased a bit and soon she was slamming my ass, her pink finger nails gripping my hips as she pulled herself deeper and deeper into me. My cock continued to rub on this silky pillow and I could feel another orgasm approaching. Before I came, however, I felt Alex slam me one last time and then hold herself in me as deep as she could.

Her cock twitched in me and I could feel cum leak from my ass. I came into the pillow below me and collapsed forward with Alex still in me. We lay like that for a few moments, quietly catching our breath. Finally she rolled me on our side into a spooning position, her cock shrinking and sliding out of my pussy hole.

And this is where I sat, fulfilled. No guilt, nothing but pleasure, unbelievable pleasure.

What a night it was.

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5 Comments
AnonymousAnonymousover 13 years ago
HOT HOT HOT

Wow, Micky - so nice. The idea of being fucked the first time by such a sexy T-girl and cumming like that on the pillow. It was very hot.

Kisses.

AnonymousAnonymousover 14 years ago
Great detail and hot sexy story - I am dripping

Very hot girl. Very hot. I loved it.

AnonymousAnonymousover 14 years ago
Two crossdressers

There i was,pantyhose, panties, at the adult shop,looking thru a glory hole at stay up nylons,sheer panties and a hard cock.I went hard,i whispered when i knock on the door come to the room at the end.I paid for the room, picked up any movie and the guy put it on,i knocked as i passed and entered the room.Short skirt entered,i was just in pantyhose and panties,the skirt was lifted,down i went on the semi hard cock, a hand on my head, sucking as it sprang to attention in my mouth.Moved away, forcibly turned around,hand on my hosed arse,tracing my crack, pantyhose lowered, turned my cock sticking out,panties lowered as my cock was taken in the warm mouth, a finger pushing into my hole as my cock was sucked, then two, my cock swelling, cumming, yes as i empty into the offered mouth.We stop, i am turned around,forced to kneel on the foam bed,the hard cock at my hole,entering me all the way, my hips held as the fucking begins, in, out of me, yes, do me, thats it as the cock comes nearly all the way out before it is pushed all the way back in.My cock still hard, leaking as my hole is fucked,until i feel it, hotter seems bigger then the familiar jerks as i am filled with your seed, yes dont stop ahh, yes as i push back so the seed can be forced all the way in me.You slowly pull out,aaghh,my hole closes,i pull up my panties and my hose as you leave a wet stain already on my panties.Bliss.

AnonymousAnonymousover 14 years ago
Very good very real

A good realistic story. This is one od the best of this kind. Keep writing you are good

AnonymousAnonymousover 14 years ago
Lovely in pink

Micky doll. I loved your story and hope you write more. I too am a part time gurl that really loves to suck another gurls cock as she is still dressed sexy. I know the rest of your week was just as wild as your first night out. I have the first 2 parts of my first night out in Hollywood posted here as Sally's first. God how I love sucking cock while dressed like a slut and getting fucked is just too tooo good, esp with another gurl, hopefully with a big hard cock. Keep writing and I'll keep cummmmming back for more. Feel free to write me at sally_spandex69 at yahoo dot com,,,XOXO Sally

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