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FIRST TIME

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  • FIRST TIME

    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.


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