Category: Shemale Sex Stories

I was going home after a long day’s work and didn’t feel like driving in the crappy weather. It was raining cats and dogs, anything was hardly visible and roads were flooded. In that weather, I found a girl looking for lift. I had to stop and I watched her as she slowly walked towards my car. She stood at the window hesitating. I assured her I am not some kind of psycho. She smiled and slowly got in. I turned on the blower, she was dripping wet. I started the car and slowly drove around. I didn’t know an unexpected surprise on a road trip like this is awaiting for me.

I am Natalia, a shemale and I have enjoyed rough sex a lot. I like fucking both men and women as long as I am satisfied. This one night I was literally made to get pleasured by my neighbour and I enjoyed it a lot. He had just jumped me and entered my apartment forcefully. I got scared and resisted but the minute he kissed me I relaxed.

I was a student by day and a firefighter by night. I had joined the team two years ago and was trying to get a college degree by attending classes at night. I often used to silently masturbate when I would go to the library, as I was alone in the evenings, at the almost closing time and it would take the edge off a bit. During one of these times, I saw the local librarian and oh she was hot. Perky tits, tight ass and a low cut blouse. Wow. She would probably feature in my fantasies for a while.

Sheila was going to see Dr. Dray. He was a supposed gynaecologist who specialised in herbal medicine. “What was that?”, Sheila had thought, but she went anyway. When she arrived at the clinic she was met by the nurse and told to lie down with her legs open and panties down. As she lay, she saw that the nurse was watching her and her eyes were glued to her cunt. She was going to meet the horny doctor there.

I was at my friend’s bachelor party in Vegas and was going to experience something different. We were hitting up several clubs and in one I met Irina. I saw her dancing over the bar. Great body and amazing tits. I looked up and smiled when she caught my eye. She smiled as well and came down towards me. I am well built and was 27 when this incident happened.

I had met Josie at a bar and she had no qualms in letting me know that she was a shemale. We both were drunk and horny, so she let me feel her up. I had had gay encounters and considered myself bisexual, so I wasn’t afraid of touching another penis. It made me hard. I was too drunk for sex so I shared my contact information with her and when we met, there was a porn flick made on my camera while having sex with a shemale.

Shana was sitting on the bed with a sultry look in her eyes. I was going to fuck her, fuck a shemale. “ I am going to suck your cock and fuck your ass,” I tell her. “Yeah, I will do the same to you. Now come here. I want to suck your lollipop,” she says and licks her lips. The tone itself makes me go wild. I go closer and let my naked and hard dick hang in from of her. She takes it in her hands and rubs it between her palms.

I am a lonely man in his forties. I love to travel, dine and explore new places by myself. But I often wish for a partner. I got divorced early, so the little chance of being with someone was also ruined in my memory. So, each morning I would go to work, do my mundane bank job and visit my nearest LGBT bar. I am sharing my memory of sex with a Shemale and how I found pleasure in it.

It was typical lazy afternoon and I was lounging on my couch trying to jack myself off. I was fantasising about my neighbour, but I didn’t know if he was into fucking shemales. I was a shemale, with a great set of boobs and a dick. And then the bell rang.

Laura was married, happily married to Matt for a long time. But today she was nervous, she had no idea how to tell this to Matt. Her phone pinged. The message was from her husband asking if she is excited about tonight. She was, but she was nervous and little scared as well. She finished cooking the dinner and went to take a long hot shower to calm her mind. She slid into the bathtub and started soaping herself. For some reason, she was feeling particularly hot tonight. Matt has been away for two weeks on a business trip. She thought about him as she touched her hardened buds and swollen breasts. She moved her hands down her abdomen and then further down until she was holding her throbbing erection. Yes, you read it right, her husband had a wife with a cock.

My friends and I were planning a weekend getaway to my lake house where I experienced orgy with a shemale. I didn’t know that they were planning my birthday party too. I packed up and all of us headed to the house. Soon it was evening and I hear the doorbell. “Surprise delivery!” my friend Sean shouts. I go to the door and see a tall blonde walk in. She is dressed well, some cleavage too and heels. She has a large paper bag in hand and she sets it down on the coffee table.