Category: Cross Dresser Sex Stories

When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. The onlookers at the store, would often look at me in astonishment and wonder, “How is this little boy handling pencil heels so well”?. My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male.

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.

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.

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.

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 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?

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.

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.

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.