stories men caught crossdressing

I had the will to live happy, that’s what my Nana had said. Today at 28 with a body on the heavier style, I still am sassy and outspoken. Sometimes I do feel let down by my body but I feel I make it up with my will to stand proud and strong. One day, I chose to visit some adult dating websites portal and signed up to see what it is about. What did I know that I would meet someone special from a dating website.

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.

I had met Faheem, at a sex club a few months ago. He was young and attractive and looked like he had expensive taste too. His attire and attitude reflected that but at the same time he was a sex fiend. We got talking that night as we watched a woman tied up and get whipped on her ass. She was leaking and then her master fucked her with the whip’s handle. Faheem liked BDSM and that’s what brought him here. After that meeting, we had gone to his hotel and had wild sex.

I had a maid working for me for a year now and often I had caught her masturbating. She didn’t know yet, but when she thought I was away, I would secretly watch her as she cleaned my bedroom. And one day when I caught her masturbating on my bed, I gave her a good pounding – in her pussy with my cock. Now she would sometimes shamelessly walk around only in an apron, showing me her cunt. So, one day I brought James, my friend, over to watch my juicy maid.

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.

This happened four years back when I joined a new office. I was 26 years old at that time with fresh mind and body but inclined toward lesbian sex. My boss cum manager there was Betty. She was a 52-year-old lady with a little chubby body and a figure of 38D-38-36. She was a very strict lady, and I have often seen her shouting at other colleagues. But she was a little soft in the approach towards me. During my initial days at the office, I had only a few interactions with her, but after a couple of months, we started to talk more and she often dropped me at my house. She led a happy family life with her husband who works in the Government sector and two sons working in MNC’s.

Alessia was always a wild child and that what attracted me to her at first. There was this need to subdue her and fuck some sense into her, may be a wild sex session with my maid. I had made her my submissive and I could fuck some sense into her on a regular basis. I loved doing that – fucking her, especially if she resisted me. I smile at that thought and enter my apartment.

Joanne has made me cum just by using her mouth and I couldn’t imagine what I would get once I fucked her. Jofre was very happy with my performance and was waiting eagerly for the proper shooting to start. He had shared the script and it was completely in detail. Every time I had to touch her, the place I had to touch her – pinching, biting and caressing, everything was in the details. While reading the script I began to imagine it and instantly my dick got hard. Actually, anyone can get an orgasm from script reading itself as it is described so nicely.

I was a forty something married woman, but I didn’t enjoy my sex life. My husband was always too busy and often away on business trips. I needed sex and for the first few years I used vibrators and other toys to manage. But I had always dreamt about fucking a boy toy, a young one and riding him till I was satisfied. And one day an opportunity knocked at my door.

I am Sagar, a 24-year aged man, or woman you might say. I started loving the clothes of the woman since my teenage and I like turning into a woman. I always use to wear women’s nightwear while sleeping and even during the day I used to wear a bra and panty under my men’s wear. It used to give me immense pleasure. One day, I went to watch a late night movie. Beside me, a handsome man was sitting. After half an hour or so, I felt his hands caressing my thighs. I was a little confused but I was enjoying his touch. So, I let it be. His caress deepened and my erection was getting stronger with each stroke. Slowly his hands touched my hard cock and I sucked in my breath.

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 had strict instructions from Darren. No underwear in this house. I had started as his housekeeper but now I was his sex slave. I was only allowed a thin negligee and I was to be bare for him at all times. I quite loved that role and every time he was around in the house I felt so horny and hot for him. I did my best to get him to fuck his slave.

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.

I was 21 when I met Jo – Josephine actually, but she preferred Jo. She was all of 18 and a very spunky girl. She was Fran’s daughter. Fran – my father’s wife. I hadn’t seen her before although Fran and Dad were married for more than four years. Maybe because I was at university and hadn’t come home in a while. But this summer, I saw her. She was a tiny brunette who was interested in astronomy. What I didn’t know was that she was untouched and I discovered about my virgin stepsister soon.

I was in my second year at law school, when a new teacher joined the faculty. She was in charge of teaching us Criminal Law. Five-foot-six, slender figure, dark brown hair with a few loose curls, our teacher Serena, was mesmerizing to say the least. She had a perfect cleavage and her ass was tight. As she stood in front of the class, doing her job, all I could do was stare at her. I imagined all the things that I wanted to do to her. I wanted to hold her and lick her into oblivion. So in order to get close to her, I approached her after class with the request to help me with the subjects personally since I was having difficulty in understanding the theories. I was just taking my chance but didn’t know I was going to experience bliss- my first lesbian experience with my teacher!

I had a high-flying career and was married for the last 10 years. But my husband was mostly away on business most of the year, saying that right now was the time to earn. I agreed with it. We could earn now and relax later. But lately, I had been feeling lonely and quite horny. I was angry and frustrated as I missed sex with a person. But because we had mutually decided to live like this, I couldn’t say much on it. I couldn’t say I changed my mind. So, I waited for things to change. I wanted get banged hard because I’ve been missing sex.

Dating sites have become the new to go places to look for partners. These partners could be for a long-term romantic relationship or for something on a short term. You don’t have to frequent places such as bars or clubs to try and find that person. All you need to do is get online, create that profile and get started to find a real hookup partner.

It was dark in the hall, with dim lights. The only light that shone brightly was at the center, on a raised platform. A woman was screaming in pleasure. Tied up, suspended from the ceiling, she was spread out and we could all see her pink cunt. A man was penetrating her with a whip handle and drawing her juices out. The very way the voyeur was doing things, made me feel hot.

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.

I had never thought about BDSM as a sexual act that would appeal to me. So, I never even thought about trying it. But the first step into BDSM sex, for me was with someone so sensuous and beautiful, that I enjoyed it thoroughly.

Hi, guys, this is Andrew. I have always been attracted to mature and older women. I used to stay with my family in Miami. But recently I had to shift to Orlando for my post-graduation. To start with I am a 23-year-old guy. I am an average looking guy but quite friendly with people. I started with my course, and I used to stay in a rented flat. I had a classmate named Ugaan who used to live just near my home. So we both used to spend time together playing or roaming. Once he invited me to his place for dinner. I also agreed and went there. He used to live with his Mom Roslin, though she was 45 years old, she was a pretty and attractive lady. One day I went to his place. As she gave me a glass of water, she bent to put it on the table. I saw her cleavage which got me hard. I knew it was wrong, but this made me think about her in another way, and destiny had something else defined for us that led me to have sex with my friends mother.

I have been exploring my sexuality for a while now and while I cannot confirm that I am a straight man, I am still not sure which category I fall into. But a trans person is living right next to my apartment – Benny and I feel like doing dirty things with him. I mean like he dresses so well and rocks a full face of makeup with a slight beard. He does have generous boobs and I have thoughts of my trans neighbor, every time.

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.

My name is Diago and I am just 18 years old. I am currently in my senior high and I belong to a very rich family. My parents both works very hard to provide me with all the luxury I want. My father owns a steel factory and my mother is a fashion designer. Before getting into the story of the sexy servant, a brief intro about us.

Daryl was supposed to be my one night stand, but instead he took pleasure in fucking me again on a secluded beach. It was the attraction that I blamed for this. We met on the night before but couldn’t get to fucking because he had a medical emergency…yeah, he couldn’t get his dick up. I laughed and laughed. But he found me the other day, when I was lounging on the beach. That’s my story of how he fucked me on an open beach!