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My Best Friend’s A Shemale free porn video
I had known her all my life, even before she became a girl.
My name is Johnny and I am eighteen years old. I am not the most handsome guy around, but I good looking enough to hook a sexy girlfriend. That girlfriend used to be my best friend, a guy.
Jesse was always an effeminate guy. He was soft spoken with soft features. He was always shy, but not with me. He always had long hair and when it wasn't tied into a man-bun he looked very much like a girl.
Shortly after his sixteenth birthday, he told me about his plans to transition. It came as no surprise to me and I hugged him close for the last time as a guy.
Jesse dropped out of school shortly after and he seemed to go off the radar. He never went off the radar with me though, sending me pictures and texts all the time. Over the next year or so, with the aid of the pictures she sent me all the time, I watched as shy effeminate Jesse turned into the gorgeous soft breasted Jessica. She looked amazing and when she sent me her first fully nude pics I was amazed by her amazing body and large erect penis.
She told me that every day she thought of me and in a few short months she would be ready to come out of hiding.
She wasn't really in hiding, it's just the way she put it. She had gone over to America where people didn't know her, and it made her transition easier. I loved her more than I did when she was a guy and felt myself get hard every time I looked at her pictures.
Finally, the day arrived when she would come back. Her mother called me and asked if I would like to accompany her to the airport to pick her up, I jumped at the chance.
We waited at arrivals for her to walk through the doors. I knew she would have a little trouble at customs and watched as everyone walked past us. Finally, I saw her walk through the double doors and I could not help but get hard right there and then. She was wearing tight jeans and a white top, I could clearly see her bra under her top. Her face seemed to light up when she saw me and walked right up to me. We hugged each other tightly and I could not help myself but kiss her. We made out slowly right in front of her parents, her breasts pressing up against me.
We parted and Jessica hugged her mother and father. We all went out to the car and Jessica and I climbed into the back seats. We held hands the whole way home, and I knew we were meant to be.
Over the next week, we spent a lot of time together. It was great getting properly reacquainted. We hugged and made out a lot and both our parents didn't seem to have a problem with it. We went on dates nearly every day and no one batted and eye at us. For everyone it just seems like teens going out together. We had really become boyfriend and girlfriend.
We were sitting in Starbucks one evening sipping cappuccinos when Jessica turned to me.
"Johnny, I love you."
I could not help myself and leant forward, giving her a soft peck on the lips. She smiled at me and slid her hand over my thigh.
"I'm still a virgin. I want you to take my virginity." She blushed at me. "You know what I mean, I want you to be the first to put your cock in my ass. I want to feel you inside me and make me cum."
I knew what she meant, and I wanted it too. We both decided that we would do it the following week, the eve of her eighteenth birthday. As much as we had sent pictures to each other, I had yet to see her naked in the flesh. The thought turned me on and at the same time made me nervous. I had never had a problem with guys, and knowing Jessica as I did, I definitely didn't have a problem with her. The thing was to me there were boys and girls, I had had fun with both. I had never been with a ts before, I knew it was no biggie, I was just nervous.
The day arrived, and I had arranged with my parents that they would be out the house when she came around. They had agreed with me it was something they would rather not be home for. They decided to go to a restaurant and not get back till late, by which time Jessica and I would have done the deed.
Jessica arrived at my place about eight thirty wearing a sexy revealing dress and thigh high socks. She looked amazing and I got hard right away. I took her to the living room where I opened a bottle of wine for us. We drank and talked, kissing each other every few minutes. It was about nine thirty that we realised that we had finished the whole bottle and she suggested to take her to bed.
Up in my room, we lay on my bed kissing. We held each other close as our hands roamed each other's bodies. I pulled down the zip at the back of her dress and slid my hand over her bare back.
She pulled away from me and slid out of her dress. She looked amazing in her underwear. I could see the bulge in her panties, which only seemed to make me get harder. We both stripped out of our clothes and lay together naked. Her soft breasts pressed against me as her cock pushed up against mine.
We kissed as her hand wrapped around both our cocks and stroked them both at the same time. Her lips left mine as she started to plant kisses down my chest and over my belly. I felt her lips wrap around my cock and I groaned loudly. She was an amazing cock sucker and seemed to know every trick in the book. Her tongue slid over the underside of my cock head, giving me maximum pleasure.
After a good few minutes sucking, she looked up at me and smiled.
"Johnny, would you like to suck mine now?"
I had never sucked a cock before, but I wanted to suck on hers. I nodded at her and she stood up in front of me. Her cock was bigger than mine and I seemed to salivate as I took it into my mouth.
She groaned as I started to suck her cock, her hand resting on the back of my head. I sucked her hard, paying close attention to the underside and her pee hole. She seemed to love it and started to fuck my mouth. She made me gag as her cock hit the back of my throat.
I felt her ass start to jerk as she fucked my mouth and I knew she was going to cum. I tried to pull my head away, but she held it in place as she fucked my mouth hard. She groaned loudly, and I felt her hand let go of my head. She came in my mouth. Jets of thick gooey ooze shot from her cock into my mouth and I by mistake swallowed some of it. It didn't taste as bad as I thought it would, in fact, it tasted good. I lapped up the excess cum and sucked the tip of her cock clean.
She lay back on the bed and smiled up at me. I lay on top of her, kissing for what seemed an age.
" I want you to fuck me now. Fuck me till you cum in my ass."
She rolled over giving me a full view of her feminine hairless butt. She looked so amazing and I don't think my cock was ever so hard. She spread her ass cheeks for me, and I pushed my cock against her waiting hole. She groaned loudly, pushing herself back against me. I started to fuck her butt as best I could. It was the most intense feeling I ever had. My cock was made for that ass. It was not too tight but not loose. It was perfect.
I pounded her butt as best I could, making her groan and whimper into my pillow. I could feel her arse clench around my cock bringing me closer to the edge. I pushed her down and lay beside her, spooning. I wrapped my arms around her, cupping her soft breasts. She groaned and pushed back against me as I groaned in sheer pleasure. It didn't take long for me to go over the edge. I slammed a few more times and shot my load deep into her butt. I held her close feeling her body shake next to mine.
I slowly pulled my cock from her butt, seeing some of my cum ooze out with it. She wrapped her hand around my cock, squeezing out the last drop of cum from my cock. She then licked her hand clean which almost made me cum again.
I could feel her hard cock against my thigh and she smiled at me.
"Johnny, as you can see I am pretty hard again. Can I fuck you now? You're the only person I have ever been with and have never fucked anything before. I would love it if I could feel your tight ass around my cock."
I couldn't refuse her, she just looked too good. I was about to roll over when she grabbed my legs to stop me.
"No Johnny, I want to fuck you missionary. I want to see how you look whilst I'm fucking you. And I want to be able to kiss you."
She took my pillow and placed it under my hips. She sort of pulled my legs apart, moving as close to me as possible. I could feel the tip of her penis push gently against my sphincter. I closed my eyes and braced myself as I felt her push forward. With one hard thrust, her cock was inside me.
"Oh my god Johnny? Your ass is so tight. It feels so good, I'm not sure how long I will last."
I couldn't really talk. It felt like I had the wind knocked out of me. It wasn't so much painful as u comfortable. She started to slam her cock into my ass, pulling all the way out and then slamming it home. After a minute, I felt a strangely pleasurable feeling. With her every thrust my pleasure seemed to increase. It wasn't the same sort of pleasure I got from fucking, it was like something was going on in my core.
I closed my eyes as Jessica leant forward to kiss me. I could feel her breasts on my chest as she fucked me for all she was worth. I could feel her struggling to keep a pace going as she got closer to the edge.
"Johnny, I'm going to cum. Fuck, you feel so good, I'm so close."
She lifted my legs and pushed them so I was nearly doubled over. I could feel her cock slam even deeper than before. She started moaning loudly and then I felt it. First, it felt like a small squirt of hot cream in my ass and then she flooded me. I felt her pull her cock from my ass and her cream ooze out with it.
Jessica collapsed on top of me, her body heaving. I held her close for a good twenty minutes before either of us said anything.
"Jessica, that was amazing. I love you and want you to be my girlfriend."
She looked at me with those beautiful big eyes and gave me a peck on the lips.
"I love you too Johnny, I have always loved you. Since I got back you have been my boyfriend, I have thought of you that way anyway."
We kissed each other passionately, lost in our own world. It didn't take long to fall asleep and it was one of the best night’s sleep I have ever had.
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Jessica and I have been going steady for more than ten years now and life is bliss. She has blossomed into a gorgeous sexy woman and we often make love to each other. For the most part, she's a bottom, but every once in a while, she likes to fuck me. I have gotten used to her beautiful cock in my butt, especially when she cums inside me.
Jo
- 14.04.2020
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- Trans
