When she stand up straight she looked at me dead in the eyes and put my hand on her semi hard cock and told me "start getting comfortable with it, touch it, make me hard" and so I did, feeling it grow in my hand. I couldn't even move, she crouched, kissed me and took my hand. It didn't take long until she pushed very gently my head back a little and took her panties off, and then I saw it for the first time, a dick that wasn't mine own.
I went down to my knees and stared at her, She chuckled again and said "touch me trough the panties, feel me", and I started touching her cock through her underwear, and just like in a movie started licking her through the panties. It was a mix of feelings I was scared but so much exited. The moment I had dreamed about for so long it was about to become true. She went on for a minute or so and got up, kissed me and whispered to my ear "your turn, get down to your knees". She went down to her knees and lowered my boxers, I knew what was about to happen and couldn't be happier, she started sucking my dick like no one had ever sucked me before, it was awesome. I started touching her boobs and butt and she also was touching me, my cock was rock hard, she started touching it gently. We started kissing, very wet and passionate kisses. When she came back she was no longer wearing the dress, she had on lingerie set. She told me to get naked and that she will be right back, and left the room.
The light was dimmed, a big bed, it was quite high, on the TV was playing a porn movie, and I saw by the night stand a big bottle of lube, condoms and a roll of toilet paper. Come on, come with me" she took my hand and led me to her room. I'm only afraid it may hurt a lot", she chuckled and told me "don't worry, it won't hurt.
She asked what my fantasy was, and I answered "I want to be bottom. Invited me in and we sat on the living room for a little while, gave a glass of water and we started chatting. About my height (5'9"), big breasted, she was wearing a tight black and very short dress, showing all her curves. When I got to her apartment she was even more beautiful than the pictures. Rang the door bell, it was an intercom of a building with no doorman she opened the door for me and told me to go in. I jumped into the car and drove to her place. She laughed a little, and told me to come over, that she had experience with "first timers"
The phone rang a few times until a very sweet voice answered, she sounded sexy and friendly, we spoke for a few moments and I told her that I was looking for my first time, not only with a shemale but as bottom all together. I dialed her number on my phone, but for some reason I had a hard time pushing the "Dial" key. I spent a few minutes checking and decided for this brunette, long haired, girly, big breasted and with a big dick shemale. So the idea came to mind, Why not go for a tranny? Went on Google and searched for tranny escorts on my area, and to my surprise the market was huge!!! Beautiful shemales offering sex (of course it was not for free, but who cares?). But the idea of having a man on top of me was not what I wanted, I didn't want to have sex with a guy, I just wanted to have sex with a cock. So this one night, I was jerking off and then i thought to myself "why not?” Went into the local gay chat room and started looking for someone to "get together with". The idea of having a beautiful woman fuck me was very exiting for me. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the tranny porn was the best. I had the fantasy about sucking dick and getting fucked.
For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc.) but I really wanted the real thing. I was 18 and wanted to try being a bottom. So this is the story about how I got my first experience being a bottom, and why it was with a tranny