So since I got a good rating for my first sex story, I shall write another one about my first time with a tranny. This happened last year. She was 25, and I was 21. So I am Ash, I am 22, I pretty good and masculine looking. I am mostly a bottom though. I have always been a huge fan of shemales and ladyboys. Respect them and also lust for them :p anyway, so I was in dubai last year and I thought that there might be much more shemales and easier to meet since the place was quite forward with a lot of foreign nationalities. I was on pr and other channels, looking for shemales whom I can meet, especially top or besatile ones. One fine day I came across a beautiful looking tranny on the site, who from the looks of her profile seemed a very fashionable one and also a hair stylist herself. She told me she worked in a saloon and that she liked me. She told me that she has a massage room for massages and…. . I instantly signed up after asking the rates and all. The saloon was all the way across the city, so I went there after calling her in the evening, took me some time to get there. After finding the place I called her and she came out to escort me, and helped me to a chair and after deciding on the hairstyle, she started her work and was standing really close to me. She was styling my hair and my attention was all over her body which she kept rubbing against me, once she puckered her butt to my face, and once she rubbed what seemed like her boner on my torso. Once she was almost done, she blew a little air on my face, to blow of some hair, her face really close to mine. She asked me if I was ready for the massage and I barely could say “Uh..You..Yeah”. She escorted me to an inner section and we were in a small massage cum spa room with a table in the middle. She came close to me after closing the door and asked me @are you alright honey? Did you like that haircut?@ and we conversed a little, all the while heating up the room. So then she asked me to get on the table and relax and that she will be back in a minute. I stripped and put on the towel, trying to hide my boner. I laid face down with the towel still around my waist. She came in, checked me out, and pulled off my towel to a bit below, exposing my butt cleavage hehe. She did that while gently fondling my boner and smiling as she did that. She kept talking to me as she started to massage my back. I kept my legs a bit open, hinting at my readiness. Anyway she was massaging my lower back, after which she reached down and started rubbing my thighs, and reaching up and up. My boner struggling already, she reached up and grabbed it, and pulled it between my legs, letting it loose. I gently patted her hand away, as she remembered how I had told her that I am sensitive and also mostly a bottom. She realized that, and started kneading my buttocks. And I just moaned out a little, she then reached closer and gently fingered around my rim and I moved my legs and gently rubbed it against her thighs. After a while she came near my head, and started massaging my lower back as she bent forward and her crotch cloose to my face, inching closer and finally rubbing on my face. I looked up and kissed it over her pants, she immediately looked down and let her oriental dragon free, right onto my lips and then in between them. And then started a lot of sucking on her lovely cock, as I turned around and she face fucked me. Then I moved onto her nips, those supple breasts so so yummy, and she loved it, as she shifted my head from one breast to the other and then eventually her lips, kissing and making out. Once we were done eating each other’s faces, she whispered that she is going to take my sweet sweet ass but that she liked a smooth ass and I was hairy as fuck. She laid me down and got me into doggy pose, and soon there was this warm spread on my butt cheeks, as I tuned and saw her applying wax on my ass. She looked at me and whispered “This one’s on me”, once done she pushed me down on the table, I was kissing her as she raised my legs and placed her cock on my ass as she liplocked me and then docked me. And then fucked me for a good amount of time before starting to jerk me off as well as she fucked me hard. I asked her to let go of my cock and just fuck me harder, she was loving it and tried a couple of poses as kept kneading and rubbing and gently spanking my butt cheeks while fucking me. She was getting close and holding me tight while she fucked me and then I came right with her as she oozed in me and I squirted on myself. Once we were done, she cleaned us up and then kissed me, finished the massage. And then I was a regular client for her for almost an year. And she made sure to fulfill both of us every time. I even fucked her once, when we were way too horny. But still finished with her fucking me, as she always said that she loved my ass. Hope to go back soon and my superhot tranny hairdresser again. If you do like this, do comment and like, cause that acts as motivation to write more, and I have some fun stories in store people and I shall share more. If you want to contact me, then get me on [email protected]
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