Tranny Stories

Though I am very active in having sex with men as a closet tranny, I never tried anything in public and wanted to try at least once. So, I decided to grab the opportunity on my train trip to Delhi. Though I was not fully dressed up like a tranny, with my attire, tattoos, and glossy lipstick, anyone on the platform or train could easily make out that I am a gay or a transgender and that thought gave me an instant kick. It happened on my train journey to Delhi a month back. I was wearing a lady v-neck slim fit t-shirt a thigh-sized shorts and slippers with my sexy lady specs on. I also had ta... Read full Story

The first time I ever cross dressed was when I was seventeen years-old, so not to long ago. I was in my freshman year college and my roommate I was invited to a party thrown by a fraternity on campus. However my roommate was kind a of skeptical about a fraternity inviting a bunch of freshmen to their party. Me being an over zealous teen persuaded that they might want us to join their fraternity. He agreed and swallowed his fear and off we went and feeling like proud men getting ready to join a fraternity. When we drove up to the frat house, we were amazed on how big and beautiful it looke... Read full Story

I was on CL the other night checking out ads. I came across one by a CD. He wanted to fuck Bareback outside by the front door of his apartment. It sounded hot, He told me it was dark and no one could see us. I imagined a porch with no neighbors near by. I get there and is a regular house in the suburbs. The only shadow there is created by the garage of the house. I was a little scared. As soon as I got there he told me to get on my knees and start sucking him. The house faces an empty lot so there couldn't be any one seeing us from a window but anyone driving by could see us. I start ... Read full Story

I've been having Urges to Get Fucked. The thought of a Dick in my mouth gets me so Hard... I masturbate to Sissy videos at least 2wice a week; I'll laydown on the bathroom floor to spread my legs to finger misf while I stroke my Cock w/ my right hand. Sometimes I wish there was a Strong man to watch me and help me get off ... During the week, I go to the weightroom gym to workout and then I see this one particular Guy; Strong & focused. I pictured myself in the shower room hoping he'll catch me Naked and try to Force himself to me. I wouldnt mind his friends joing in t... Read full Story

Ok so not only was this a mistake. Kind of. I'm but ik I regret it but at the same I didn't. Im not gay or anything but god when it was in........So I was on meet me. And got semi catfished by this dude. On the profile he was a beautiful Hispanic female who could have been my baby mother ????????????my dick getting hard just thinking bout it. So anyway we start talking and he says can I eat your ass. Now No I was not sure if he was serious so i was like wtf ???????? then he proceeded to say he was a Tranny. Btw that was a lie. So I played along he semt a dick pick i sent my ass and h... Read full Story

In my city there are several transsexual brothers where there are usually a good amount of attractive girls working. It had been quite a while since I've visited one but on a hot sunday night I decided to pay one of them a visit. Even though I had been here before I was nervous, the place is on the top floor of a regular apartment building and there is always a chance of running in to somebody who lives there. Luckily that didn't happen and I made it to the top floor unseen. I was introduced to around 10 ladies and made my pick, a tall and slim Brazilian girl called Yasmin. Ver... Read full Story

West Palm Beach didn’t have many cold snaps, but when one did rake the city the weather seemed twice as frigid as it actually was. Virginia Stanton sat alone in her office on the third floor of Prism Design’s building overlooking the Intra-coastal Waterway. She had been chilly all day, mainly because of the dampness in the air; Forty-eight degrees outside wasn’t all that cold. Factor in the wind and cold breath of the Atlantic Ocean, however, and chilly became outright icy. The tall blonde set down the file and her ballpoint pen, wearily reached up to unfasten the simple c... Read full Story

Just a true story, first of a few telling how I got where I am: First Time With A Man: Ok, pretty tame but here goes... One night when I was about 14 or so a strange thing happened. I ran out of smokes... that's not weird but if you're a smoker you know it sucks. So I walked up to the 7-11 to get a pack and was burning one outside when this guy pulls up on his motorcycle and runs in for some shit. He comes out a minute later and asks if I want to smoke a number. Sounded like fun so I said, cool, and hopped on the back. We tooled around the neighborhood for a bit and he pu... Read full Story

Cara's First Time This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in my showgirl sister's outfits and feel the soft touch of her dresses on my skin. It's just felt right to me all my life and I guess that's the way I'm programmed. After many years of just dressing in the clothes I eventually began using make-up and wigs to complete the look a... Read full Story

I hear a knock at my door and go to answer it even though I'm only wearing a little black see through lace top, black lace assless panties, thigh high fishnets and stiletto heels. I open the door to see all the men from this group I started on kik. "Guess this is my lucky night. Come on in", I say as I turn around and walk towards my bedroom walking as sexy as I can so my butt wiggles for u. I barely make it into the room b4 I feel hands on my waste pulling me back to feel a cock push against my hole. I bend over for easier access and feel it slip inside. I feel it throb as it s... Read full Story