When I left my high school, I decided to go on a gap year and travel the
world to see lots of interesting people and ways of life. My first stop was
Thailand which was great and I had so much fun partying with my friends as
around 5 of us went on the trip.
After Thailand the next stop was in Brazil and due to the time of the year
the nightlife was truly amazing. We had decided to stay in a rather swanky hotel
as this was a dangerous place from what we heard from the guides and people
there. The first night out was great and we drank a lot and got to know the
clubs nearby before making it back to the hotel to pass out. The second night
however is one that has been imprinted in my mind for a long time...
We went to the first club and I split from the group of us to talk to others
in the bar, I started talking to a woman and she was so funny and really rather
attractive like no one I had seen before, there was something special about her.
ANyway we carried on talking all night and she explained that she lived quite
far away, so in the mood for a bit of action I invited her to stay in my place
that was right round the corner. She followed me round the streets and up the
lift in the hotel before we reached my room.
As soon as i opened the door she was all over me and i wasn't going to stop
her because she was incredible looking. WE continued to kiss passionately before
I pushed her onto my bed and got on top of her removing my shirt. She removed
hers and I couldn't believe I hadn't noticed but she had amazing tits so round
and really quite big but I new she must have had implants for those sort of
breasts. I buried my face in them and we continued to laugh while I slowly
slipped in some dirty talk, explaining that I was going to shove my cock deep
inside her dripping pussy. The foreplay had been and gone and so she rolled me
over and kissed her way down my chest towards my now firm, throbbing cock. She
pulled down my shorts and started to suck me off. It was amazing and she had
clearly had lots of experience as she was so damn good and I can remember it to
this day. She continued to suck going from my dick to my balls and I could feel
I was close to cumming so I said that I wanted to pleasure her and hold it in
She turned over and got up and started to do a sort of strip tease. She
pulled down her very short skirt and revealed her nice white thong, I couldn't
believe her ass it was so damn good. Then something strange happened. While
still turned round she said 'promise you won't be angry or upset', obviously i
asked why, but she was insistent I promised and so I obliged. she pulled down
her thong and turned round. There it was right in front of me was a big floppy
cock, it even challenged mine in size at around 7-8 inches. I thought about what
had happened but then I pushed it aside, why not I told myself. I grabbed hr
hips and pulled her towards me, while she was still standing I took her cock
deep into my mouth, I was surprised at how far down her shaft I made it. It was
surprisingly good I loved to suck cock, especially as she had tits also.
She asked me if i was daring and i said yes, in a flash she flipped me over
so my ass was straight in the air and she started to spank me. It was such a
good feeling and my cock was so hard I thought it was going to shoot off. In the
moment and the horniness that had overcome me I shouted out ' stick that cock up
my ass'. Next thing I knew was a 7 inch cock being rammed up my incredibly tight
asshole. at first it hurt and i screamed in pain but after only minutes i was
enjoying it so much. We changed positions and I sat ontop of her using my legs
to draw her dick in and out of my ass. I then felt a warm jet right into my
asshole, she had cum inside of me and the feeling was great, I almost came
myself at the feeling. She said it was my turn and so got up and pushed me over
again she stood over me and bent down until her ass was right over the tip of my
She forced her ass down over my cock and it was a great feeling I came after
only 4 rams up her ass but continued to go. We were now on the floor and I was
all over her kissing her neck and playing with her tongue with my own. Just then
all my friends walk in, they had had a key from reception, I didn't even notice
but kept on ramming her, luckily they saw that I was in the middle of something
and left, to this day most do not know it was a tranny.
I took my dick out of her ass and went down on hers, we got into the 69
position and continued to suck. She came all in my mouth and i came in hers, I
swallowed every drop and it actually tasted great. I then pretty much passed out
on the bed. When I woke up it was like we were a couple, wrapped round each
other in an embrace her tits right next to my face. She then said 'this holiday
will be great and maybe your friends would be interested in me and my friend.'
We continued to fuck every night trying new things in different positions until
the last night when my friend joined in also. All three of us kissed each other
and we fucked like a sandwich, I penetrated my friends asshole and took his cum
in my mouth, talk about a holiday.
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