My First Man

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My First Taste of Man
1.1k words
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I started cross-dressing at a very young age. I believe my first time was in a pair of my moms tan pantyhose and high heels. It was a joke that my sister did on me but ever since that I kept doing it in secret. I use to wear my sisters panties, hosiery, bras, and make up. I got very good at making myself look like a woman. At 5"11 and very slim it wasn't that difficult to believe I was a fine piece of ass. After getting in college I started to purchase thigh highs, heels, wigs, and everything it took to become a sexy cross dresser. One night I decided to take my dressing to the next step. I took a warm shower and shaved every inch of my body. I then proceeded to put on a pair of lacy black panties and black pantyhose. With that I slipped on a stuffed red bra and red 5-inch heels. I finished the outfit with a very short red minidress. After finishing the make up and wig I looked in the mirror and saw that I was one of the best looking women I had ever seen.

I really didn't know what to do once I went out to the club. I never have thought of being with a man or what I would do if I were approached. I hesitated if I really wanted to go out, but forced myself to do it. On the drive over I kept getting a nice boner to the thought of the soft touch of a mans lips on mine. I couldn't believe what I was thinking, but decided that tonight was the night I was going to try it. As soon as I walked into the club I got sexy smirks, stares, and ass smacks from every guy in the room. If only they knew what I was hiding underneath these cloths. The night proceeded with dances and shots of vodka. I danced with a lot of guys and grinded my tight ass on everyone of there cocks. It was such a turn on and as the drinks kept being brought to me I knew that I was going to get lucky tonight. One guy caught my eye the most. He was very buff tan with short black hair. His muscles seemed to be popping out of his shirt, which turned me on so bad. He danced with me a lot and grabbed my hips as hard and as sexy as possible as I grinded his ever growing member in his pants. I wanted him bad and he knew it. After the last song he grabbed my hand and took me to the bathroom.

My heart began to pound so fast and I got very nervous but the alcohol was telling me to just do it. Once inside he pushed me against the wall and began kissing my neck. His hands began to grope my ass and legs. I could feel his cock against my leg. As he kissed my neck harder I slowly moved my hand down his waist. I started to massage it through his jeans. His kisses got longer and I knew he wanted me. I never would have imagined being able to do this to a man. After a solid two minutes of this he pulled his head away and kissed me on the lips. His eyes sparkled and I knew what I wanted. I kissed him hard and our tongues wrestled against each other. I wanted do anything and everything with this guy I didn't even know. I began to undo his pants as we swapped spit over and over.

I was so hungry for his dick I couldn't wait any longer. I kissed him hard and dropped to my knees. I pulled his 8" cock out and kissed it on the head. I quickly started to licked it all over the base. His moans from above told me how much he wanted me. I was so turned on I didn't even hesitate shoving it in my mouth. The feeling was amazing as it slid in and out of my mouth. I sucked it so hard he twitched multiple times. I stopped every once in awhile and licked his nuts and kissed his waistline just so it would last as long as possible. Before I could begin again he pulled me up and kissed me. I tried again to go down but he wouldn't let me. Instead he whispered in my ear how much he wanted to fuck my ass. I never thought that I would want this, but I was too horny to decline.

I walked over to the sink and bent over and stared at him and winked. He followed and pulled my wig hair back and kissed my back and neck and then lifted up my dress. I looked in the mirror and saw him staring at my pantyhose covered ass and he instantly pulled them down to my thighs and began to insert his cock into my ass. It hurt so bad at first that it was hard to not cry. After a few attempts it finally fit all the way in. I let out a loud moan and he began to fuck me. Slow at first because of the pain, but as he continued I started to not only like it but love it. I yelled faster which he of course did. I loved it so much; I started to thrust my ass back into his movements. We moaned together over and over. His balls were smacking my ass and I started to massage myself. As we did this over and over I felt myself cum in my panties. I was praying that he didn't see the stain or the boner I had in front of me. I wanted this straight man to never know what he was doing. It made things so much hotter.

He thruster a few more times and I felt him tense up, and all of a sudden his cum shot straight into my ass. It was a feeling I had never felt before. Everything seemed to slow down and I felt euphoric. He rested his dick there for a few seconds until finally pulling it out ever so slowly. This gave me enough time tuck my now limp cock away, and then turned around and sucked the rest of the cum off his cock. He moaned as my tongue played with his over used cock. I got up and fixed my dress and pantyhose and then kissed him on the cheek and told him to call me for round two sometime. I handed him my number from my purse and walked out of the bathroom knowing I would see him again.

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AnonymousAnonymousover 6 years ago
FIRST OF THE MANY

I took my first buggering at 17 in a public toilet in the town of Woking in the UK in June 2006. I was wearing normal male top clothes but had on seamed stockings, a deep six suspender belt (garter belt in the US), matching bra (with false tits) and a tiny G-string, all in black. Once in a "trap" (cubicle) I put on my 4inch spike heeled "Fuck Me" shoes and clip clopped about to attract attention. Soon I saw someone looking through a peep hole from the next trap and made sure he saw what I had to offer (my virgin arsehole) and we passed a note back and forth until he came into my trap. I sat on the throne and took him into my mouth to get him really stiff for me, then got up, bent over and pulled the string out onto my left arse cheek. I had prepared my "Pussy" for use, with an enema and KY jelly before leaving my flat, I may have still been a cherry boy, but I wanted to get my sex life REALLY started. He fingered me a bit and KYed his cock, then started to work it into me. It hurt and took some time, but with him pushing forward and me pulling my cheeks wide and pushing as if to remove a turd, he suddenly popped in, and I yipped. My de-flowerer began to slowly ride himself into me and after a while I picked up his rhythm to push back to force him deeper into me, the pain turned duller and then the feeling started to be enjoyable. When his balls slapped my arse, he rested a few tens of seconds, then began a full length tip to balls stroke as the FUCKING began in earnest. He rode me for quite some time to our mutual enjoyment then sped up on the short strokes and dumped a full load into me. He slowly shrank and then slipped out of me, followed by a large part of his load. As it was before noon, a invited him back to my flat, and he screwed me another couple of times that day. He still comes around regularly to service me, along with many others. They often buy me the kind of clothes that they want to fuck me in for their own fantasies, from vintage lingerie to the latest (usually the third or so time around) fashions. But the most requested is to have me in their daughters school uniform and/or teen styles.

AnonymousAnonymousover 12 years ago
Really sweet story

Sounds like my first time with someone that I wanted it to happen with. I hope that you find the time to tell us more about any other encounters you might have had.

Lumpy26Lumpy26over 12 years ago

Good first timer story, very well written.

AnonymousAnonymousover 12 years ago
Begining

Was there any more further adventures for you along the way?

sally_spandexcdsally_spandexcdover 12 years ago
Love first times

Great story that I'm sure most of us gurls can relate too. I KNOW I'LL NEVER FORGET THE FIRST TIME A HARD COCK SLID PAST MY LIPS, INTO MY MOUTH. Just knowing that this is the night you finally become the slut you always wanted to find. A slut who loves to grab cocks and grind their hot asses into it, hell in general one that lets you know she just loves a good hard cock. I have posted part 1 and 2 of my first time out and about as Sally. [Sally's first by sally_spandex69] OH what a night. I hope you write more and more and am going to check your other stories too...Sally

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