This happened as a result of a challenge. A dare to be specific. It was a Hen Party and we were at a place with many other girls, some of whom I didn’t know. I am Jennifer, 26 years old. We were drinking and having fun. There were games and one of them was truth or dare. Feeling brave I took a dare and I had to kiss a girl. I didn’t knew this would lead ahead to a beautiful lesbian sex experience.
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.
I had been working for Perez for a year and had seen his roving eyes watch me. I knew what he thought of me and wanted me to sleep with him. But I hadn’t given him that opportunity yet. As a result I did get secret gifts and requests to give in to him. The truth was, I was attracted to him and was just about to give in. That mutual attraction with my master would lead to a blasting sex, I didn’t know.
I was meeting a group of guy friends at a bar. It was a renowned gay bar where drag shows were held on Tuesdays. So I went there, a woman. I was bisexual and enjoyed dallying with both sexes. I was enjoying the show, singing along when I went to get a drink at the bar. Max was serving drinks and the first thing I noticed about her was that she had heavy eye jewellery. Piercings and heavy makeup made her eyes pop even more. I didn’t know I would end up sleeping with the Waitress I met there.
Andy knew me like no one else. My likes dislikes he knew everything. No wonder I was smitten with him. We were dating and going strong now for 6 months. Our sex life was explosive and we couldn’t get enough of one another. However, he hadn’t touched me anally. He hadn’t gone there and fucked my ass. So I decided to surprise him. I wanted him to claim me in every way. I was planning for a session so he can claim my anal hole and fill me up.
I remember being stuck inside my apartment during those rainy nights. Boredom and frustration lead me to chat with strangers online and suddenly my rainy nights weren’t so depressing anymore. I saw Katya that night and just loved the way she responded to me. Even though we were physically apart she definitely lit my fire.
His eyes were following her every move. Katya was serving the drink in the billionaire’s party, moving graciously, heads down, shying away from anyone who made a pass at her. His gaze had so much intensity that even I could feel them from a distance, the strength of kinky sex and roughness. I had no idea what he has in mind but I was about to find it out soon. I, Anaita, am 24 years old, just the same as Katya. We have been friends for quite some time now and we even work for the same catering company. Katya is a shy woman of 23 years of age who thinks she is not beautiful enough. She would have a fit if she knew she was the centre of attention of a billionaire prince himself.
This is the final part of my story Gay Experience with a stranger. I will write in continuation of the cross dresser sex and how he fucked my Asshole.
Hi, I am Shail and I am 21 now. The incident I am going to narrate happened in high school when I was 16 and became slut of my friend. My parents wanted a daughter but I was their only kid so, my mother often used to dress me up like a girl when I was a child. That stayed with me as I grew up. I used to dress up as a girl in the solace of my room as my parents strictly ordered me not to dress like a girl ever. I had no idea this will change my entire life. One day I was dressed up as a girl when a friend from my high school came banging in my room. It was then that I realised my room wasn’t properly locked.
It was one night when my cousin Joe had come over to our house. We had all turned eighteen over the summer and the way he was looking at me was making me shiver. I knew it was wrong with him being my cousin and all but the attraction between us was something. I wanted to have sex with my cousin and my body was electrified when I was near him.
They always say, the first time is shocking, the second surprising and the third, well, there is no stopping. I have been a very adventurous and rebellious girl. I like to question things and people quite often, which earns me, quite a reputation. With this typical characteristic of mine, I was asked to leave my home and never show my face again, by my own father. They said that they have tolerated my gypsy spirit, but they can’t anymore as they were answerable to God. How did everything change and how unconventional anal sex brought back pleasure in my life is what I am going to share in this story.
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 had the hots for my gym instructor. He had a good body and I often had erotic dreams about this man. He had a little stutter that would show up when he was nervous. How did I know this? I was at the gym twice in a day, so around him for a lot of time. He had a very prominent accent and I could spot him anywhere by his voice. Then things changed. I had sex with my gym instructor and I felt wonderful.
I was a part of our college football team and had practice that afternoon. I arrived at the locker room to change and saw this skinny older guy. He was wearing spectacles and talking to coach. That was the first time I saw Laurent. Later I found out that he was a visiting Maths professor. He taught at the university. We slowly became friends, even though we were from opposite spectrum. I was a jock and he was more interested in theorems. Everything seems so good so far right? It went way too far from just studies and I ended up having sex with my maths professor.
I am 45 years old and my name is John. My wife is a socialite. She has so many friends that she is invited to various weddings and parties all the time. I am a person who likes to stay indoors after a long day of work. Although, this one time she forced me to attend a wedding with her. I had come home early from work and so, I agreed. Didn’t know this would turn into an affair with wife’s friend.
BJ was my first boyfriend and I had met him at a party with common friends. It was strange how I, a virgin at 26 met another virgin who was 24. He was nice and while friends at first, we moved into the dating territory soon enough. The first kiss was weird and sloppy, wet almost. I wasn’t sure if I had wanted to kiss him and he wanted to very much. Soon our relationship progressed and we experienced first sex soon.
This was the third time I was meeting Xena. I was having an affair with her and I had kept it a secret from my wife. What do I say? I was addicted to her or rather my cock was addicted to her pussy. And she was naughty as hell so I enjoyed doing things with her of sexual nature. I don’t feel bad having an affair with a hot escort like Xena.
Hi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire.
I was practicing as a general physician in a rural community and would often see cases that were out of my scope. However, as I was the nearest doctor, I would see a lot of local patients with various ailments. One day, a skinny and heavily pregnant woman came to my office and boy did that session last. She seemed young and was unmarried. And when she came in, I oblige to her request and I fucked my pregnant patient.
In my family, women are always covered in a Burkha. It is believed that covering up a woman’s body keeps them safe from evil eye be it from their own father or even their husband’s ninth wife. Like in the western world, when I was a kid, we were never exposed to a woman’s body, apart from their eyes or their feet. Clean beautiful feet with mehendi design or alta dye stain, often made me wonder about what lied under it. Destiny had something else defined for me and I sharing my story of fetish seduction on my wedding night.
I met Lisa in college and then we also had some steamy webcam sex. But that’s not the end. It was because she wanted to relax sexually and didn’t want the hassle of dating a guy. I wanted her. Oh, I so wanted her. But she kept denying me. And now we are stuck together on a plane. Right next to each other, in economy. Why, you ask? Because we are on a freaking college trip or an educational trip if you prefer. That was it. I had some sexy moments up in the air itself.
I am recounting this tale as it happened when I was in college. I was still discovering my sexuality and wanted to try everything. So, I ordered some sex toys online, keeping it for future use. I had a girlfriend and I would fool around with her. We had had sex occasionally but I was a young horny guy, wanting to explore more – try toys and some kinky acts. And I was preparing for it – a sensual and sweaty night.
I had a different sexual relationship with my husband Jan. He liked being the cuckolded husband and it added spice to our sex life. We had experimented with many kinks and one was when I had tied him up put him inside the slotted cupboard. From there he watched me getting fucked by a bouncer that we had found at a nightclub. He came just by watching us and I had a lot of fun getting rammed by a big black dick. That was a fun night.
This is the second part of my previous story. I will write about how I had rough Cross dresser Sex with him.
My name is Aryan and I was posted in Chickmanglur, an area with a lot of hills and coffee plantations. I was sent there for handling the production work. I was given a guesthouse to stay and a house-help, a man named Hari, who helped me with basic things I needed. His wife used to prepare food and do cleaning stuff for me. His wife, Rekha, was a very beautiful and desirable woman. I am going to share my story of how I came closer to her and had sex with the wife of caretaker of my guest house.