First Time

By if.tenep.nona@065292na

Published on Dec 7, 1995

Transgender

Controls

Message-ID: 011351Z07121995@anon.penet.fi Newsgroups: alt.sex.stories X-Anonymously-To: alt.sex.stories Organization: Anonymous forwarding service Reply-To: an292560@anon.penet.fi Lines: 171

****************************************************************************** WARNING! This story contains graphic description of a sexual encounter. If such material offends you, please don't read it. *****************************************************************************

FIRST TIME The guys in school always used to give me a hard time. My hair has always been long and combined with soft features, they felt obligated to tease me to "prove their manhood". I've always been smart enough to know that the guys who gave me the hardest time were the ones who were most insecure and probably turned on by me (classic homophobia). I was always very social in school and had a lot of friends (mostly girls), which probably irritated the "tough guys" even more. In my junior year (i was 17), a friend of mine invited me to a halloween party. Jill was a friend of a friend of a friend and had recently moved to another town. She was a cool artsy kind of girl who although wasn't overly attractive, had a great personality and was always a lot of fun. She was big into theatre and had big plans to attend acting school in NYC next year. The party was in a house just down the street from hers and her parents were going to be away that weekend. Jill asked me to come over in the afternoon so we would have plenty of time to put together costumes and catch up on things. When i got to Jill's house, she was wired. She had costumes, makeup, and props all over the house and was running around in a frenzy. "This party is going to be great.", she said. "It's going to be huge! I'm so glad you're going with me because i won't know many people at all!" This of course was not a problem with Jill. She would probably know everybody by the end of the night. Jill picked out this Victorian gown type thing to wear. It was huge and even though i thought it was a bit much for a crowded house she was determined. "This is a beautiful dress and probably the only opportunity I'll ever have to wear it. You better start putting something together yourself." "What should i go as?" i said. She started chanting,"vamp, vamp, vamp....". "I asked what's a vamp?" She said "you know, that 20's look." "Long tight dress, black satin gloves, cigarette holder, MataHari, Orient Express, GET IT!!!!" " I asked her if she thought that I could pull it off and she said "no problem, i have everything here from a play we did last year." She went through the pile and produced a beautiful black satin dress; floor length with a slit to the crotch and low cut with spaghetti straps. She also pulled out a pair of 4" high heel sandals and of course a pair of elbow length black satin gloves and a black and gold 12" long cigarette holder. I said OK, but you'll have to make me up (knowing that she loves to do makeup). "This is going to be great! i took a shower and washed my hair. Jill loved my long hair and wanted to fix it up. She blowdried it all straight and fixed my hair up in a 20's style. she pulled it back and put it in a beautiful shiney french braid. the sides were slicked back and decorated with little hair combs with rhinestones on them. Very vamp! Then came makeup. She got all excited over my hairless face. First a little foundation and blush, then the eyes. She did my eyes in a 20's style too. False eyelashes and heavy liquid eyeliner. Then she did my lips. "Very important." Jill said. I have full lips and she spent about 15 minutes lining them with a dark red lipliner pencil. Then with a lip brush, filled them in with dark, blood red lipstick. The effect was amazing! I really looked hot and didn't recognize myself in the mirror! It was getting late and we hurried into our costumes. She in the "big gown" and me in the vampy dress. Jill loaned me some black pantyhose and giggled at my smooth legs when i put them on. she also handed me a strapless bra which produced even more giggles. The dress fit ok and i added some tacky dangling earrings, fake pearl necklace, the gloves and the cigarette holder. The slit in my dress came up to my crotch and provided an incredible leg shot as i walked. Oooops, the shoes. Jill handed them to me with a smile. "I dare you to keep these on all night!" They also fit ok (i think), but wow, when i stood up and walked in them i understood what Jill meant. I loved them but no way would i accept her dare. We walked down the street to the party and it was going strong! The house was packed with over 100 people and you could hear the music from Jill's front door. We walked in, i looked around and got nervous. I was expecting a highschool crowd but it was older. Mostly college age and up to mid 30s. Jill and i found the keg, poured some beers and walked around. I got stares from everybody and a few lewd remarks too. A bunch of guys called me "Madamme X". A cute girl dressed as "Wonder Woman" with a chest to match came over and flattered my look. Jill ran off with some friends and Wonder Woman and i went to the kitchen for beers. It's a good thing i was getting buzzed because the crowd was getting real loose and "very friendly". I didn't realize it at first, but i was passing real well. It was kind of scary. Older guys were coming on to me and getting bolder and bolder with each beer. Then some real rude "jocks" came in the room. Somebody tipped them off about me and they were real rude. The said things like, "you look real comfortable in that dress honey" and "you like that cigarette holder in your mouth don't you". Just then Jill came by and pulled me away. "Lets go downstairs and smoke a joint in the pool room." We went downstairs and a couple of "hippy types" were rolling a bone. We decided it would be cool to smoke it in my cigarette holder. It was good weed and we all got real stoned and decided to play pool. I forgot about the jocks upstairs and started to relax. The party was thinning out and soon it was only myself and a cute girl i met earlier. Jill came down in the middle of a game and told me she was going home and asked if wanted to stay. I said "sure, but i'll be leaving soon". Then the "jocks" came down to play pool. Three of them. Jeff (not his real name) put his name on the scoreboard and claimed "next game!". i won my game and the girl i was playing with left. i was going to leave too, but i thought i would deal with the jocks a bit. they had intimidated me earlier, but a few beers and the pot had loosened me up. All night long people were blown away by my appearance and i had a lot of confidence in "my look". I realized that these guys were just like the guys in my school, just a little older. They were turned on by me and felt threatened by it. I knew they wouldn't hurt me at a party and i would probably never see them again so i decided to go with the flow. Jeff and i started playing and the other two teased me. "i know you like dick honey". "when's the last time you took it up the ass", "you didn't get those round lips from eating square meat". the last remark cracked me up and i tried to hold back a smile but they caught me. Jeff said, "you always wear your hair like that?" I said "no, usually i wear it down." With that, i reached back, removed the combs, undid the braids and shook my hair out loosely beyond my shoulders. For added effect, i fixed my lipstick. You should have seen the looks on their faces. "you guys like it don't you", i said. i knew i was pushing my luck but i was prepared to act on it a little bit. i had never done anything with a guy before, but i liked the "role play" and was curious about what it might be like. Jeff said, "you want it, don't you. that's why you have long hair and dress like that". "Bullshit" i said. "It's halloween and you're the one with the hard-on!" "I'm going up to the bathroom and getting a beer." i said. The house had pretty much emptied out and the keg was empty. Time to go home. I went to the bathroom and took a pee. I looked in the mirror and checked myself out. With my hair down, i looked totally different. OUT was the 20's look, IN was the hooker look. I shook out my hair some more and borrowed some hairspray on the shelf and sprayed my hair out big. I fixed my lipstick again and headed for the door. Just as i opened the door, Jeff walked in and locked the door behind him. "Hi Baby". All of a sudden i got real nervous and regretted not leaving with Jill. Jeff noticed my hair and said "making yourself pretty for me?" I said no and he asked, "well then, for who?" I said "nobody" and tried to move past him. Jeff blocked the door and "i know you want it". Even though i was scared, the situation was turning me on. Jeff was a football player or something at University of New Haven and had some sort of "Rambo" outfit on to show off his body. "I'm sorry i was rude downstairs." "Come on, i think you would really like to suck me off", he said as he started to undo his pants. I knew i was in a tough spot, but i guess i really had "asked for it". I had never blown a guy before and i wasn't really sure i wanted to. i guess he took my silence as a "yes" and pushed me over to the toilet, closed the lid and told me to sit. i started to protest a bit but i realized that the only reasonable way out of this was to blow him. He stood in front of me, undid his pants and pulled out his cock. At 17, i hadn't seen too many cocks before. His was almost purple, rock hard and had pre-cum dripping from it already. He had a huge wet spot on his underwear from being hard for so long. He touched my closed mouth with the tip and smeared my lips with his sticky pre-cum. "Open up, baby, i know you want it." he said. I parted my lips a bit and flicked the head of his cock with my tongue as he pushed his cock about halfway into my mouth. He groaned deeply and grabbed my hair as he pumped his dick in and out of my mouth. I really didn't know what i was doing, but he didn't care. He ran his hands through my hair as he fucked my mouth, all the time saying things like, "that's it baby", "you like to suck, don't you", "you live for it, don't you baby". The reality of sitting on a toilet in an evening dress with a football player's dick in my mouth was a bit more than i could handle and i tried to pull away. "Not yet, honey." he said. he grabbed the back of my head with one hand and grabbed his dick with the other. With just the head of his cock in my mouth, he started jerking off. "oh yeah, oh yeah" he said as he tightened the grip on the back of my head and pumped his hand faster. I knew that there was no way avoiding a mouthful of cum and as he started to yell "that's it, that's it" i closed my eyes and braced myself. just then he yelled at me. "look at me!, look at me!" "i want to see you looking at me!" Just then he started spurting in my mouth as i stared into his eyes. he just stared back as the last of 5 or 6 jets of hot cum emptied into my mouth. then he said "i want to see it" as he pulled his cock from my mouth. I wasn't sure what he wanted but he was obviously into "visuals" and i was relieved that he didn't want me to swallow. I looked up into his eyes and parted my lips a bit as he stroked his cock over my face. Then as he watched i let the cum flow out over my bottom lip and over my chin and down my neck. He smiled and said, "thanks baby, i knew you wanted it" and left. I cleaned up and headed for Jill's.

THE END

I hope you enjoyed the story. write me if you did. thanx, kris --ATTENTION--ATTENTION--ATTENTION--ATTENTION Your e-mail reply to this message WILL be automatically ANONYMIZED. Please, report inappropriate use to abuse@anon.penet.fi For information (incl. non-anon reply) write to help@anon.penet.fi If you have any problems, address them to admin@anon.penet.fi

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