Rebeccas Insel
- 3 years ago
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Rebecca's Back-Door Lover free porn video
Rebecca's Back-Door Lover
Hello again, my dears! It has been far too long since I wrote my last
story, about my very first sexual experience with a man - which was also my
first sexual experience with anyone! This story is about my second time
with a man, and my first experience with anal sex.
To re-cap, I started dressing in mom's clothes when I was 12. When I was 15
I started to pick up some items of my own, and when I was 17 I dressed up
for a man I met online and sucked him dry. This story takes place about 3
weeks after the first time.
I had just had my first experience with a man, and I loved it! I had never
been as happy as I was when I was in a dress and on my knees. I knew I
liked oral, but I still had to try anal. I had been talking to an older man
on IRC in the room #gaydads4sons who loved feminine boys like me. He lived
in New York City, and I lived on Long Island. As luck would have it, my
parents had gone away on vacation and left me home alone. I was logged into
the chat room, and my older online friend happened to be logged in too. I
told him the news that my parents were away, and he said he could come over
that afternoon and he wanted to bend me over. I was thrilled and nervous,
but not too nervous to prevent getting a little bulge in my panties!
I had about an hour until he arrived, so I quickly ran into the shower and
made sure to clean myself very well. Then I toweled off, and grabbed some
clothes from my mother's dresser and my own. I borrowed a dark blue, plain
knee-length cotton dress from mom's closet, but I wore my own black bra and
matching panties underneath. I didn't stuff the bra, choosing to fill the
cups with nothing but my chubby teenage boy boobs (which are now chubby
adult boobs). I finished off my outfit with a cheap shoulder-length red wig
from a local costume shop, and a pair of low-heeled black mules from
Payless (size 12 wide - curse my big feet!). I put on some brick red
lipstick that matched my wig (and would also match my natural red hair),
and sat in the living room by the back door waiting for my man.
I heard him open the backyard gate and come up the wooden stairs to the
gate. I stood when he got to the deck, and I opened the door to let him
into the house. I was so nervous, until he stepped into the room and took
me into his arms and kissed me deeply. I melted, and I returned his kiss
and blushed a deep red. I took his hand and sat down on the couch with him.
We smiled at each other, then he leaned in to kiss me. We made out in each
other's arms, and I was in heaven! I loved, and still love, kissing men.
After maybe 10 minutes of fantastic French kissing, he pulled away and said
"I heard daddy's little girl likes sucking cock."
Without any hesitation I replied "Yes daddy!" and got down on my knees in
front of him. I smoothed my dress under my bottom as I rested it on my
legs, and I unbuttoned and unzipped his jeans. I pulled them down, and
freed his cock. My first man had a fairly small one that was very easy to
suck. But this guy had a real man's dick - a solid seven inches! I didn't
know if I'd do a good job sucking it, but I also knew I desperately wanted
to try! I kissed the head, leaving a faint mark of lipstick on it - the
rest having rubbed off on his lips from all of our kissing. I licked his
penis from base to tip, and then I put the head in my mouth. I softly and
slowly sucked on it, making him harder and harder. I gradually started
sucking a little harder and faster, taking a couple more inches of his meat
into my mouth. I was hoping I was doing well, since it was only the second
blowjob I had ever given. But I needn't have worried - he was smiling and
moaning, and held my red wig as my head bobbed up and down. He said "Good
girl!" which are the two words that turn me on the most. I had a growing
wet spot in my panties as I was drinking up his precum.
However, he told me to stop, because he didn't want to risk shooting his
load into my eager mouth. He wanted my virgin ass. He stood me up, kissed
me, and slowly lifted my dress up over my head. Now I was standing in front
of him in just heels, bra, and panties. He kissed me again as he unhooked
my bra, slid the straps down my shoulders, and removed it. Then he kissed
me a final time as he pulled my panties down and I stepped out of them.
Then he bent me over a chair in the living room, and he got down on his
knees and licked my virgin hole, giving me my first (and only) rim job. It
was a strange feeling, but rather pleasant. But after a couple of minutes
came the moment of truth.
He stood back up, told me to relax, and positioned the head of his cock at
my waiting hole. I was already nervous, but now I was even more so because
the only lube he was using was his own saliva. He told me it would be okay,
and to just relax. From the sex stories I had read online, it seemed like
it would hurt at first but then slowly give way to pleasure. So I relaxed
my hole as best I could, he put his hands on my thick curvy hips, and
slowly entered me.
In all honesty, even though this was my first ever fuck, it didn't hurt at
all! I had practiced a couple of times with a bottle of moisturizer and a
hairbrush handle, but that was nothing compared to his thick long cock. But
there was no pain at all! Then he told me "I'm all in!" and I honestly
could not have felt prouder. Then he said "Congratulations. I made you a
woman now." I let out a low moan, and told him "Make me your woman, daddy!"
He started slowly thrusting in and out, making my own rock-hard but small
clitty bounce all around. Then he moved me over to the couch and put me on
all fours as he knelt behind me and thrusted a little faster.
He was moaning and grunting, and I was softly whimpering as sissy-boys do
when their cherry is taken. I started pushing my ass back into him to meet
his thrusts, and he started fucking me faster and harder. Soon he had me
flat on my stomach as he was pounding my ass on my parents' couch. I was
steadily leaking precum onto the couch, and he was steadily leaking into
me! He told me he was close to cumming, and I begged him "Finish in me,
daddy! Fill me up! Fill my ass!" That sent him over the edge, and he gave
me my wish. I felt him flood my no-longer-virgin ass. He stayed in me for a
few seconds, then slowly pulled out.
We kissed again, then both got re-dressed. We kissed some more, and then he
opened the back-door, went back down the stairs, out of the yard, and back
to his car. I got my bra, panties, and dress back on and went into my room.
I re-applied my lipstick, then sat on my chair feeling his cum leak out of
my hole and into my panties. I held my stomach and briefly imagined being
pregnant. I started to turn myself on thinking about breastfeeding, and
giggled realizing that I was thinking some seriously feminine thoughts.
Maybe he really did turn me into a woman! I opened the windows, then opened
my dresser drawer and pulled out the ashtray and pack of Capri 120s that I
had hidden away. Smoking has always turned Becky on, even when I wasn't old
enough to legally buy my own.
I reflected on the afternoon. My first time three weeks earlier could be
considered just an experiment in oral sex. But now not only had I gone all
the way, but I had enjoyed it. I never thought I'd lose my virginity to a
man when I first hit puberty and got interested in sex. But now at 17 I had
done it and loved it. I could not call myself straight anymore. I was
definitely very much interested in men and taking the feminine role.
I never did meet up with him again, but I did remain in contact with him
online. We still talk to this day, ten years later. And while I have
certainly had (and enjoyed) sex with some handsome men, I still haven't had
the final experience of true femininity - a stable, loving relationship
with a man. Maybe in the near future my next story will get to be dedicated
to my boyfriend...or perhaps even husband. But until then, Rebecca is
still on the market. Kiss kiss!
Emely
- 28.10.2022
- 37
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