A meeting in Leather Part 10
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Kerin free porn video
When I was in college I had an ex girlfriend, Colleen, who I stayed
friendly with. We'd hang out time to time, but secretly. I'd go by her
place and she'd leave her bedroom window open just a crack. There were
things under her window which I could use to climb right in. We did that
so I could easily avoid her parents who hated me.
One day I came by the house, glanced inside through the mostly closed
blinds, saw her, and did my quick entrance. Only once I got in the room I
freaked out her brother Kevin who was in the room. Mostly I freaked him
out because he was in there wearing his sister's clothes. I'll admit it
took me by surprise. Kevin was pretty scared because he had nowhere to go.
I just happened to be in between him and the door.
The first thing he said when he realized it was me was, "Brett please
don't beat me up." I asked, "Why would I do that? Of course I won't beat
you up." He quickly explained to me that nobody knew about this, including
Colleen whose clothes he was wearing. He begged me not to tell anyone. Of
course I agreed to keep his secret. It was the right thing to do.
He was visibly shaken. I told him to go change in to his own clothes and
I'd take him out to calm him down. After he changed we went out to grab
some burgers and to hopefully chill him out. Plus, I had questions too.
The typical stuff. Was he gay? He said he didn't know. How long had he
been doing this? He was 18 now and he said he started around 12. He
actually used Colleen's clothes because they were the sexiest between his
2 sisters and his mom. His mom being a bit frumpy and his sister Dierdre
being a bit of a slut.
But today was his greatest fear come true, getting caught. I could tell
how scared he was despite the fact that he was calming down. I told him,
in the future, come dress at my apartment. I live alone and I already
know. But I told Kevin, just don't hit on me and all is well, and then we
laughed at my joke.
How was I to know I had just invited a teen girl to move in lol. Kevin was
at my place constantly. Some times he dressed and went out, Other times he
dressed and just wanted to hang out. This was the 80's so no internet. But
Kevin found magazines that had all kinds of stuff he was interested in. He
really started to amass quite the wardrobe. Some times she would buy
things and somehow, I got recruited to pick up her clothes, shoes and
makeup other times.
Colleen had yelled at me when we were together for not paying attention to
how hard she worked to look good for me. So I paid attention to her
clothes and makeup. I would help Kevin by pointing out if he overdid or
underdid his makeup. I'd give him examples for what his sister did. I'd
advise him on clothes so he would look more authentic. I even gave him
advice on lingerie. I told him if he was moving or talking in a way that
would make people figure him out. I did everything I could to help him be
as much like a woman as possible. I even convinced Kevin he needed to
start shaving ALL over. Kevin caught me off guard one night though. He
wanted to be smooth all around his cock too. He said he knew I might say
no, but, would I shave him. He couldn't see well there or use 2 hands.
Don't ask me why, probably because I just saw him as a girl, but I said
yes.
There he was sitting in a chair in a bra and thigh high stockings while I
shaved him. He had a smallish cock. It got red, actually almost purple. It
was really hard. He said it was just his nerves. I don't know why, I
couldn't look away. It sounds strange to say about a cock, but, it somehow
looked so feminine all shaved smooth. Once I was done shaving I ran my
hand all around. You know, just to make sure I didn't miss any spots.
Then one night there was a shift. We were hanging out just watching TV.
Kevin was all dressed up. Heels, mini skirt, crop top, make up. He'd grown
his hair long and started talking so he sounded like a girl. I looked at
him and said, "I can't keep calling you Kevin. It's messing up my head.
You need another name." That's when he... I mean she, told me her name was
Kerin. The family was very Irish, Black Irish, Black hair and blue eyes,
simply gorgeous. She told me her name was Kerin. It meant "Ireland; dark"
and she thought that was perfect.
From that point on my house guest was Kerin. I will admit, even though I
didn't want to admit it then, Kerin was a cutie. We live near NYC. Later
that year at Halloween Kerin said she was going to the parade in the
village. It would be packed with crossdressers. Kerin told me Halloween is
a crossdressers New Years Eve. But Kerin was small, and I didn't want her
going alone, I thought she wouldn't be safe. I would tag along as her
protector. Her costume was Miss America. Long gown, sash and Tiara. This
way if she passed people thought that was her costume. If she didn't pass,
her costume was a woman.
The parade was fun. The whole area was jam packed. The costumes were great
and Kerin and I were having a great time. But, something else new
happened. We got caught in the middle of a crowd with Kerin in front of
me. Kerin leaned back into me while we watched the parade. And all of a
sudden, my cock got hard. Nobody was more surprised then me. I thought,
Kerin can't know. But she just kept backing in to me. It almost seemed
like she was wiggling her ass on my hard cock. And umm, she had a NICE
ass. I was supposed to be there to protect her but, now I was horny and
confused. I don't remember much more about the parade. I do remember
trying to make sure Kerin didn't discover my hard on.
We made it home that night with no event to speak of. A couple months
later, something none of us saw coming happened. Kerin came by my place,
changed and headed out. She would always tell me where she was going just
in case. I was sitting home watching tv when I got a call, it was Colleen.
She knew her brother and I were friends and he hung out at my place a lot.
Colleen and Kevin's parents got into a car accident and were at the local
hospital. Nothing too serious, but they were getting the family together
to go over there. She wanted Kevin, but he wasn't here. She didn't believe
me and said she was coming over. I'll admit I sounded like I was lying,
because I was. In minutes Colleen was at my door.
She was pissed at me and worried about her parents. She wanted to know
where Kevin was NOW. I said I'd go pick him up and bring him back here.
She said no, she was going with me. I tried everything to keep
Kevin/Kerin's secret but, I had no choice. We drove to pick up Kevin.
Kerin was at a field at a high school in a neighboring town where nobody
knew Kevin, drinking with some other kids. I convinced Colleen to wait in
the car while I got her brother. It wasn't easy.
Kerin and Kevin both weren't happy to see me, or to hear what was going
on. Kerin was about to have someone else who knew her secret. We climbed
into the car and Colleen wasn't really looking at Kerin, she was too busy
yelling at me asking where her brother was and who was this girl. Then
from the backseat Kevin said, "I'm right here Colleen." I thought she was
going to pass out. She could barely recognize him. We made quick
conversation as I drove back to my house for Kerin to change back in to
Kevin.
It had been a couple weeks and I hadn't heard from Kerin or Colleen or,
even Kevin for that matter. But I did know their parents were ok and back
home. Then one night Colleen stopped by with Kevin. Colleen asked Kevin to
leave us alone to talk. So he went in to the room where he usually
changed. Colleen said she had talked to Kerin and heard about EVERYTHING.
She was happy I watched over her little sister. She said they had a thank
you for me. Colleen came over to where I was sitting on the couch and just
unzipped my jeans and reached right in and started stroking me. We had a
good sex life when we were together and she knew what I liked. I was hard
immediately. She said that she and Kerin had talked about how to thank me.
Plus it would be doing something for Kerin too. That's when she dropped
the bomb. Kerin wanted to suck my cock and have me fuck her.
I was shocked. The only reason I didn't get up and leave was, it was my
place, well, and the fact that Colleen was making me feel great stroking
my hard cock. I said Colleen, I can't have sex with a guy, I'm not gay. So
she called Kerin to come into the room. She looked amazing. She was in a
black bra and thong, garter belt and black stockings, heels higher than I
think I'd ever seen with her long hair all done up and perfectly done
makeup. I swear I got harder. Colleen said, "Does that beautiful creature
even look like a boy? I choked out a no. But I said what's in her panties
says she is. She had Kerin turn around and lower her thong. She said,
"Does that look like a guys' ass? She has a better ass than me, and you
always liked fucking my ass." I said in the front is where the problem is.
She asked Kerin how big her cock was. 5 inches was the reply. She asked if
I'd pass up on this whole woman because of 5 tiny little inches. Colleen
asked if I would pass up a night with her if I told her all we could do
was oral and anal sex. I said of course not. So she asked why would it be
any different than what I could do with Kerin. I had no answer.
Collen said, "You're going to pass up on this beautiful babe when you're
both already crushing on each other?." I asked what she was talking about.
Colleen got up and said to Kerin, "Take this while I explain," and passed
my cock into Kerin's manicured hand. Colleen explained that Kerin had
started falling for me a while ago but never forgot the very first night
when I said not to hit on me. She thought maybe I felt the same after
Halloween. I acted dumb and said what about Halloween. Colleen explained
that Kerin did feel my hard cock against her ass. And, that it wasn't my
imagination that she was wiggling her ass against my cock on purpose.
Colleen looked me in the eye and asked me point blank if I had a hard on
for Kerin. I was trying to say no. Colleen said look, Kerin's been
stroking your cock for a while now. You didn't go soft or pull away. In
fact you look like you got harder. Colleen said, "I'll make you a deal.
Let Kerin lick your cock a few times, if you get soft, I'll give you
relief. If you stay hard, I'll leave you two alone." I should have said
no, but with Kerin looking gorgeous in front of me, I wanted her full lips
on my cock."
I felt her tongue lick up my length and I let out a loud long moan. After
that I vaguely remember hearing Colleen's heels click across the floor and
my door close. I was fully distracted by Kerin giving me a world class
blow job. I had been worked up for a while and came quickly in her skilled
mouth. Seeing her looking up at me after having so lovingly sucked my
cock, I got hard again quickly. Kerin reminded me she had two desires, the
blow job and... me fucking her in the ass. I asked her what position she
wanted. She replied, "Doggy style, for the first one tonight." I slid her
thong to the side. She had already lubed herself up some. She said she had
put a tube of KY in my night stand a while ago waiting for this moment. I
reached in, grabbed it and lubed myself up and added some more lube to her
ass. I put the head of my throbbing cock at her entrance and she was
backing on to me before I could start pushing into her. The pressure
increased, little by little by little, until my head popped inside her. It
gave us both a thrill. I waited there for a bit, not moving just letting
her get used to it. Then we both pushed against each other. Than before
you know it we were banging away. I had a feeling she was close. I had my
hands on her hips. But I took one hand off and slid it inside her panties.
When I touched her, she EXPLODED. That made her grip my cock so hard
inside her and I started cumming like never before.
We made love a few more times that night. Each trying things neither of us
had done before. I woke up in the morning, spooning my beautiful girl. My
cock nestled between her ass cheeks. Once I awoke, my cock began to do the
same. That was the beginning of a great relationship and of me helping
girls like Kerin embrace their feminine side.
Eisley
- 28.11.2022
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