trannie stories

That night was burned into my brain. I had broken up with my boyfriend, my dom, but I couldn’t get him out of my mind. His pleasuring skills still tormenting me day and night. It had been only a week and here I was rethinking going back to him. One of these days I was remembering one kinky night we had where we did it and it was so memorable. I had orgasmed so hard and he had seemed so proud to give that to me.

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.

After my semester exams were over, I was heading home to spend a couple of days of my holidays with my family. I was waiting at the airport for my flight which was due to depart at around 7:40 pm. The boarding call started around 7:00 pm and I boarded the flight and was adjusting my luggage. Suddenly, a sweet and melodious voice hit the walls of my eardrums. I turned back and saw a girl of nearly 5’3” inches with a thick bottom and average sized breast asking me to help keep her luggage. I helped her and prayed that she sits next to me. However, the luck was not in my favour, and she sat in the next row. My luck was good enough when I had a girlfriend and I was lucky enough to have sex with a virgin girl during my relationship.

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.

I am Neila. I will share my story of how I my boss had BDSM Sex with Domestic Servant who worked with her. I was 19 years old when I signed up a job for a domestic servant. When I reached the place, it was an empty room. All it had mirrored walls and in the middle was a metallic table. I had no idea what to expect. I signed up because the pay offered was good and they were offering food and lodging. I had to pay for my student’s debt. While I was deep in my thought, I jumped up from my place when I heard someone walking in. It was a middle-aged woman. She looked sexy in her leather cat suit. She was carrying a cardboard box and a riding crop. Her long thick hair was neatly tied in a high ponytail and her heels made a clicking sound when she walked.

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.

I was a pretty horny guy and my wife was ok with my sexual desires. She never said no whenever I wanted to fuck, even if we were not at home. She understood my hunger for sex. Once we were at a friend’s party and I got the desire to have sex. I found her and locked ourselves in the guest bedroom. There was no talking as she knew what I wanted. I pushed her on the bed and tore her panties. I pushed my penis in her channel and gagged her mouth with my palms before I began to fuck her. That evening was hot and dirty as we fucked in someone else’s house.

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 working for Ash for a few weeks now and I knew the way he looked at me. He stared at my ass way longer than an “employer” should. And I was attracted to him, horny at times, masturbating to his thoughts, to an image of his naked body. I will tell how the attraction moved ahead and he spit cum in my panties.

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.

I have been into cross dressing for a while now and have kept it a secret from my wife. She likes to play and is a dominatrix. Usually, we go into dom and sub mode where I worship her cunt with my tongue as she flogs my ass. I like getting dominated by my wife. But tonight, she saw me, in my female form. I was at a local club, which she doesn’t frequent, with my gang and we were all dressed up as pretty women. I was wearing her glitziest dress and had a full face of makeup with a wig. Yet she recognized me. Now I am going home and I am not sure what awaits me.

I was completely attracted to my swimming coach. He had a physique to die for. I felt like exploring the different parts of his chest and abs. When he used to wear his swimming trunks, I felt like eating him up. I used to have fantasied about him. Also, he was just 5 years elder to me. This story is about how we got close and had anal sex for the first time.

I live in Florida with my girlfriend of 2 years. We are very happy together. She works at a travel agency which often gives her the opportunity of travelling around the world. When she travels, she ensures that I am taken care off. She would often cook for me, or keep my clothes ironed, or even dry clean my shoes. The latest addition to her ‘care for Simon’ routine is hiring a maid. So, she hired Tressa. The story is about my romantic session with her and how I got the best blowjob I got from my maid.

Varun was my boyfriend and we were in a relationship past the three years. Although, lately we were doing a lot of long distance as he had to travel for work. Soon, it was going to be his birthday and I wanted to plan something special for him. Also, I did not want to spend it away from him. That’s when I had anal sex for the first time.

I came out as gay to my parents when I was around 25 years old. I knew that I wasn’t attracted to girls, but I was finding it difficult to have a meaningful relationship. I wanted hugs and cuddles, quiet nights with my partner just watching a movie and hot sex of course! I did meet attractive men of my age, but most were just wanting to have fun or wanted to explore. I wanted more, something more long term. And I guess it was because of this, that I didn’t find many partners. My sex partners were also reducing as I would start checking if he could be the one. I badly needed a passionate night with a gay partner soon.

When you are married for 10 years, your sex life tends to get a bit boring. It is the same old missionary followed by doggy or little suckity-suck here and there. Sometimes, even the thought of having fun with a new partner, runs through your mind. But, it’s all the same. You will spend the initial years of your relationship, discovering the body of your new partner and then it all goes back to where you left from. So, the question is, does that make it a wise investment? Well, in my head, its not worth it. So, I tried to put in a bit more effort of making our marriage interesting. I started off by re-observing everything Ronald did on everyday basis to keep sex life active.

I was late! I was running for an internal meeting and when I burst into the conference room, I saw it was empty? Only Sean was sitting there looking amused. “The meeting is cancelled,” he said in an understanding voice. I take a breath of relief and sit on the nearest chair. I had a lot to do, so I thank him and start working there. It was a Friday so most of the staff leave at around 3 and it’s only me and him working. We didn’t disturb each other at all while working but now I feel something change and it became a fantastic night.

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.

Shana was my aunt – my dad’s stepsister. She was a little different from my stiff collared family. She was visiting this week and I was going to see her after five years. I was eighteen now, ready to join college. It was my last week at home and Shana who was 30, was visiting. Destiny had different plans and I had sex with my aunty.

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.

We had a huge garden which had been walled on all sides. But because it was so big, we had difficulty in maintaining it. Dad would be away on business a lot and I had school. My stepmother tried to manage it but it wasn’t easy work. She often nagged me about it and it irritated me and one day I just gave it back to her.

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 a normal Friday during the summer month of the year. Me and my friend had decided on visiting a strip club far away from the city which was famous for 5 strip dancers who used to run it. The strip club was very popular because of the variety of themes that the boys incorporated in their dance and strip shows. I had never seen their pictures but had heard a lot about these strippers. I was excited to visit this strip club as I had never been to a male strip club. I had never thought in my wildest dreams that I would end up having sex with a stripper during my first time at a strip club. Once we reached the club, we saw that the crowd was full of women and some gay men dressed in short and kinky clothes.

My girlfriend and I have an explosive relationship. We love hard and we fight hard as well. And sometimes the makeup sex is rough, but it works for us. We have been together for 5 years and it’s the same story. We will have an argument; we will scream, shout and fight. Then proceed to have the most amazing and rough make up sex. This story is about a night I tied up my girlfriend and paddled her ass to make her feel the bdsm pleasure of sex.

Sheila and I had been seeing each other for two weeks now and she is my lesbian partner. I was waiting for her naked in the bathtub. I press my nipples thinking about her as I take my bath. Soon I am dressed for bed and its then that she comes in. She sees me in see-through nighty and a naughty grin overtakes her face.