cross dress stories

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.

My marriage was a peaceful one, devoid of stressors and shouting matches. But sexually, I wasn’t too satisfied. I was looking for something, wanting something more and this actually showed in my acts. Once, I was fucking my wife and although her pussy was squeezing me in the right ways, I wasn’t feeling excited enough. So much so that in the middle, my cock suddenly went limp. It was then that I thought that maybe I needed a second partner in my life to make more excited.

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.

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.

Alyssa is my sexy servant. Not literally but I like to dominate her sexually. It isn’t BDSM – our relationship, but just that we like role play where she is at my mercy and I can do all kinds of things with her during playtime. But that time I invited a common friend Walter to enjoy playtime with us.

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.

If you haven’t read the previous parts of this story read part-1 and part-2 to get the glimpse of this virgin sex story. BJ and I had been seeing each other a lot now. Ever since having sex on that day, it was difficult to be apart from him for more than a few days. We would talk on phone and I would wait for his call every day. I was loving this part of our courtship. We would still steal kisses whenever we got a chance, but I hadn’t had sex with boyfriend again. I was dying to try new things with him and soon the opportunity arose.

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.

Hello friends, my name is Ricky and this is the story of how I became a paid cross dresser two years back. It was during the Christmas holidays when I was in need of some money. I called my friend Kris and asked for his help. Though he agreed, he asked a favour in return. When I met him, he told me that his job was in danger and that the only way to save is by pleasing my boss. He told that his boss was a bisexual who had a thing for cross dresser. I used to dress like a girl at times but never showed it to anyone. Kris came to know about it when he once caught me in a floral maxi dress, masturbating myself. That small incident changed my life and I became centre of attraction for rich gay men.

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 was feeling horny today but that doesn’t mean I should think of fucking my stepmom. Cassie my usual was out of town and in this sweltering heat, my chances of finding a new girl to bang were almost zero. Anyway, I was still hoping that some girl would walk in through the door as I waited in the ice cream parlour. It was hot outside. Then the door opened and in came my stepmother.

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 watched Mrs. P for over a year now, the hot MILF next door and I knew she was quite horny. She had many suitors who would visit and then I would hear banging on the wall followed by moans. I fantasized about her and then one day I met her in person. Her glance was quite lascivious and I knew this lady wanted a good banging. I proposed to her that I would bang her if she would make a porno with me. I would hide her face of course. She agreed.

My name is Justin and I am a 22-year-old guy with a good height and an average physic. This incident is about an encounter about how I got fucked by a neighbour. I was alone at the home once. I took advantage of the opportunity of being alone and had a couple of glasses of whisky. After that, I sneaked in my sister’s room, took one of her dress, wore it, applied some makeup and started roaming in the house. Then, I pulled my dress up a bit and swayed my ass like a sexy woman. However, I forgot the window of my apartment was open. When I went to close it, I saw that the 63 year old neighbour of mine was staring at me and was clicking my pictures. I closed the door, undressed and slept.

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 an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a policeman and dad played a nurse. It seemed they were role-playing, but mom was a man and dad was a woman?

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 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.

There was this fantasy of mine where I wanted to experience kinky sex with my man and push ourselves for further fetish sex. We had already done it outdoors and were exhibitionists. Now I wanted something new to spice up my sex life. I had asked Adam to surprise me and I was looking forward to it tonight. I am Christine 32 years and Adam is 36 now but we manage to have an active sex life.

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 never believed in online dating. Although, I had been single form quite some time now. So, a friend nagged and tricked me in to registering on one of the sites. I did not use it for almost 8 days. However, it was the weekend and I had no plans. So, I thought of checking the dating site if there’s something interesting. I found out quite some good options and thought that connecting with them is not going to cause me any harm. Little did I know that I was going to experience something crazy and it ended up having the best sex but was dramatic at the end.

Do you often orgasm before your women? You probably have, most of the time. There could be two reasons for that. Either you are suffering from premature ejaculation or your woman is the kind who takes longer to orgasm. We will discuss about how to cope up with Women’s orgasm time but first thing first, let’s talk about premature ejaculation.

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.

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.

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.