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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 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.
