First ever shemale in Amsterdam
I'm 18 and I've been attracted to transsexuals as well as girls for a long time, so when I went to Amsterdam with my friends I was constantly thinking of how to create an opportunity for myself to slip away, visit a prostitute and lose my virginity.
I got my chance on the very first night, but I blew it. There are a couple of streets where shemales can usually be found, but the first time I went down one, the only girl who I was certain had a cock (sometimes it's hard to tell) was not feminine enough for my liking, so I kept walking. Down a nearby street, a girl in a window beckoned to me. I didn't think she was trans but she was so attractive I didn't care and I went in.
I was correct, she wasn't the shemale I was looking for, and what with me being an extremely inexperienced and nervous 18 year old, I came whilst she gave me head and never even saw her pussy. It was a waste of 50 euros and put me off badly.
But the next day I was checking out some girls with my friends (we were all curious about the prostitutes but none of us could have openly visited one, which is why I did it in secret) and we passed a window with a blue light, which means shemale. An extremely glamorous asian on a stool opened her legs to show a perfectly formed penis under her skirt. I was instantly aroused and knew I couldn't miss this chance to fuck a shemale. I promised myself I would come back before the end of the holiday.
I spent as little money as possible over the next few days and eventually I got another opportunity. I snuck away in the night and went back to the street with the blue lights. A cute little asian tapped on her window and I went up to her. I asked what I got for 50 euros and she said told me she would suck me off and I could fuck her in the arse. I asked if I could suck her dick as well and she said I could.
I followed her up into a bedroom where I undressed as she talked to me. When I told her I was 18 she got extremely excited. She spanked my bare arse and seemed genuinely aroused, unlike the female prostitute who was distant and cold. With all the excitement, my recollection of the details is slightly hazy but I remember most of it.
She was wearing extremely sexy black stockings and a little frilly bra, which turned me on instantly. She started to suck my cock, but I asked if we could start with me sucking her, as I was still wary of cumming early.
Her penis was fully functional but very small, but at this point there was nothing I could do about that. I had never sucked a cock before but I threw myself into it, and it was amazing. I still remember the feeling of her pubes on my top lip as I pleasured her whole cock with my tongue.
There was a mirror next to the bed, so I could watch myself as I fucked her arse. I felt magnificent, riding her from behind, going as deep as I could into her tight hole, rubbing her smooth back and arse cheeks. I was more turned on than I have ever been but I kept going.
While she was sucking my cock, I asked her if she wanted to fuck me. She was clearly having almost as good a time as me, and I could tell she wanted to. I told her I had no more money and I couldn't pay her extra, but she didn't mind and fucked me anyway. It was unbelievable, the whole thing was like a dream. We went through a whole range of positions, my favourite being 69 - sucking a cock and having mine sucked, absolute heaven.
When I could tell we were both going to cum soon, I asked her to do it on my face. She took off her condom and stood over me as I lay on the bed. Her hot juice went all over me, some of it in my mouth. It tasted delicious and I was ready to return the favour. I asked if I could cum on her face, but she didn't want to spoil her makeup so I knelt above her and released my huge load on her stomach, then collapsed on the bed with her, cum covering my face and her belly.
I'm planning my next trip already...
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