Where it happened: Puerto Rico
Langauge: English
Sex: Male
Rating: 8
Category: Straight
The only time in my life I had two girl friends at the same
time was last year. When My “regular” girl friend went off to
grad school in the midwest. I started seeing and making out
with a secretary in my office. I guess I felt a little guilty
about it because I never invited her over to my apartment
where my “regular” girlfriend was living with me when she
wasn’t away at school. But Gina and I would manage to meet
at the office, even on the weekends, or at restaurants and
places. And when we did the sex was hot and heavy, but we never
went “all the way.”
Gina was a virgin, and I hesitated to be the bastard to take
her virginity, since I figured I would never marry her. She
was nic and cute but about the only thing we had in common was
loving to make out with each other. Gina and big boobs and
a cute smile. Except for her tits she was skinny. Mostly
what I liked about her was that I could touch any part of her
body anytime and she wouldn’t mind. I did a lot of touching
at the office and even kissing when I figured no one could see.
She was always ready for it. She never complained about my not
trying to screw her. She, too, was probably a liitle nervous about
it but I could tell she would have fucked me in a minute If I had
asked.
One night at a restaurant we were in this sort of round small
booth. I could have sat right by her and felt her up with my free hand
but I decided to sit across from her. As we ate I slipped my foot
out of its shoe and put my toes up between her legs under
her dress (she was stil dressed for work). It was kinda crude
but I dug massaging her pussy with my toes in my sock. She
had a little smile on her face and was giggling. When the
waitress would come to the table I would talk to her like normal
but Gina couldn’t say much because of what I was doing to her.
We went to the restrooms in the back at the same time. Neither
one of us had to pee. In the dark hallway in the back I
grabbed her and pulled her over into a dark corner. She
was up for anything. I knelt in front of her, pulled her
dress over my head and started kissing her already wet pussy
through her panties. She moaned quietly and grabbed my head
with her hands. She wasn’t pushing me away. I pulled her
panty panel to the side and tongued her clit and slit. I
probably did this for no more that 1/2 minute when she
started moaning a little louder and shaking her pelvis in
short rapid movements. She came for about a minute. She
drew me up for a wet french kiss (she never minded the pussy
smell or sex saliva I would sometimes get on my face when I
was with her) and said “I want to make you come too.” But I
would have felt too weird having her blow me there so I just
kissed her again and we both went into our respective restrooms
to wash up. That was a typical make out session with Gina. I mean
she was hot.
A few weeks later I learned she was taking a long weekend in
Puerto Rico. She had tickets and reservations. I told her maybe
I would take a weekend in Puerto Rico too. As I was able to get
a day off for a long weekend too, I managed to get a plane
ticket at the last minute. I didn’t worry too much about a hotel room.
Gina had flown down a few hours before me. When I flew in I
just got a cab to her hotel–a real nice one on the beach. My
plane had gotten in after midnight and my when my cab got me
to the hotel the lobby was almost deserted. I couldn’t figure
out how to find out what room she was in and I didn’t want
to waste the money getting my own room if I didn’t have to.
I went over to a house phone, picked it up and just asked what
room number Gina _____ was in. They told me, no problem. I called
her up and said I was downstairs and could I come up. She
said sure and so I took the elevator up.
In a few minutes I knocked on her door. It was about 2 a.m.
and I was beat after the trip. I couldn’t wait to see her
but I felt sort of sleepy and didn’t expect her to want any
hanky-panky or me either for that matter. She pulled open
her door and sort of hid behind it. When I had come in
with my suitcase and she had closed the door I noticed she
was completely naked. The room was dark and she was giggling
about being cold and ran and hopped into bed where she
had been before I called. I really dug her answering the
door naked like that.
I used the bathroom to pee and brush my teeth. I came out
in my t-shirt and shorts. I turned out the bathroom light
so the room was pretty dark except for a little light
coming in from the window. I made my way over to the second
double bed that she had used. I said stuff about how I was
realy tired and she said she was, too. I said “No sex” then
we definitely need the sleep and she agreed. After a minute
she hopped out of her bed and came over to mine and said
“Just one good night kiss.” As we kissed I of course pulled
the sheets aside so she could cuddle up for a minute and
stay warm. We did this for a bit and it was real nice.
I couldn’t stay real sleepy though with Gina’s body totally
naked snuglling up to mine. I started getting a hard-on and
getting more alert. I kissed her again and soon we were
hugging each other, kissing and pressing our bodies against
each other. Gina definitely wasn’t sleepy.
She maneuvered on top of me and sort of dangled her big
breasts over my face. I began kissing them and licking on
her nipples which were quite large and which I dug. Gina
started grinding her pussy into my erection. For a minute
I just started playing with her butt with both my hands.
I was nuts that she was just totally nude and I could touch her
anywhere and it would be nude and she had trusted me to open
the door naked to me.
Gina was moaning louder. It was nice not to have to worry about
a co-worker seeing us or a bus-boy coming around the corner.
She could start yelling for all it mattered and I liked her being
vocal during sex.
She reached down and dragged my shorts off me quickly exposing
my hard rod. She grabbed it and put her mouth over its tip
and started sucking. As she did this I sort of sat up a little
and took off my tee shirt. Now I was completely naked too.
I pulled her back up on top of me and kissed her deeply and
she resumed grinding her pussy against my cock.
I put both my hands back on her ass-cheeks and massaged them up and
down. She started to go nuts. I realized I wanted to fuck
her real bad and thought “Too bad she’s a virgin” so I couldn’t.
I started sucking on her nipples again as I squeezed her butt
cheeks and Gina started squealing with pleasure. She held
herself up with her hands so that her boobs hung down just to
where the nipples could play around my mouth. Even in the
dark room there was enough light from outside that I could
see the expression on her mouth was all smiles. I put my middle
finger a little ways into her anus and Gina just about bucked
off me she got so excited. I thought for sure she was coming or
was about too but she just kept writhing in pleasure.
I could have sucked her tits and figured her ass all night
and been happy but Gina had other ideas. She pushed up
a little away from me so I couldn’t kiss her breast any more.
(I liked just looking at those big melons swaying right
abve my eyes.) She positioned her pussy slit right on the
center of my dick and rubbed slowly up and down it. From
her juices and my pre-cum mixed together my cock was real slippery.
Gina sat back up and rested on my thighs. She stared down
at my dick and lifted it in one hand, positioning it straight up
in the air. Then she moved her pussy lips right up over the end of
it and gently lowered them onto my prick. She pointed my
cock tip right to her love hole and moved it back and forth,
back and forth to make sure her lips were totally lubricated.
She gradually poked my hard-on further and further into her
virgin tunnel. At one time she flinched and I could tell she
had hurt her cherry. She just kept doing it and doing it a little
more or a little less. She was determined to go all the
way for the first time in her life. I figured she would
never be more hot and wet again than she was right then. Also
since she was guiding my cock by her own hand I knew the
pain she be about as little as is possible.
In a few minutes she was sitting lower on my dick, very slowly
moving herself up and down on it and I knew she was there.
I let her set the pace and hopefully start to forget the pain and
start to get the pleasure back. After another minute she had
as I could tell by her moans of pleasure starting up again and
her gyrations getting more and more active.
Gina lowered herself down to me again, pumping on my cock all
the while, and I greedily resumed sucking her nipples. Again
I grabbed at he butt and this time managed to insert both my
middle fingers into her asshole. When I did this Gina let out
an “Ohhhhhhh!” of pleasure and started bucking up and down
like crazy. She was getting kind of loud again and that turned
me on. I felt like I would come uncontrollably if she didn’t
stop acting so wild. I came like I’d never come before and pumped
cum into her for about a minute. She could tell I was coming and
it seemed to set her off too as she fell on my, her tits squishing
up against my face and shook her pelvis in spastic vibrations of
pleasure.
Gina and I fell asleep in that position, both exhausted and satisfied.
I woke up a couple of hours later. I got a towel and wiped
off Gina’s body of sticky cum and some blood. I lifted
her to the other bed and tucked her in. Then I balled up all the
stained sheets from the other bed and threw them against the wall.
Then I grabbed a couple of the blankets that had fallen off the bed.
I curled up on that bed with the blankets and went to sleep again
myself.
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