So, I got divorced this year. The up side is I'm happier. The down side is I used my ex-wife's clothes and shoes to dress up. So, I ordered some online. They arrive Saturday. I'm super excited to start my own wardrobe. Especially since things will fit better. I'm taller and have a bit larger feet than my ex-wife. Nothing was ever uncomfortable but I'm excited they'll be my own. I'm ready for my own sissy life to blossom.… Read more

I had an amazing dream last night that made me wake up with my sissy cock hard as a rock and my sissy as aching to be pounded. I woke up sweating, with a hard cock leaking pre-cum and an ass that needed to be filled. I took out my dildo and rode it until I came and ate my load for a hot sissy breakfast. This is the dream that made me so horny: I was dressed up in a tight black dress with black stockings on, a pair of sexy black patent leather heels. Like a good sissy I was plugged and caged. I was talking to a muscular daddy. He was so buff and tan. He kept telling me how his wife so soooo… Read more

I've been having a new fantasy lately. I have been fantasizing about being owned by a muscular daddy. He keeps me dressed up 24/7, plugged, and caged. He makes me keep up his house like a wife, and then he fucks me silly every night. I imagine feeling his strong hips pumping his cock into my ass. I dream of kissing and licking his neck and whispering "oh please cum in me daddy" while he's fucking me. I think of how great it will feel when his cock explodes in my boi pussy and then my tiny sissy cock leaks in a sissygasm. He feeds me my own cum and I lay there satisfied to have made my daddy fe… Read more

The first time I crossdressed was both amazing and confusing. I was so excited. I had worn a pair of pantyhose and black ballet flats. My little middle school cock had spurted the biggest load of cum I had ever produced. I felt so turned on. I knew I absolutely had to do it again. But I was also really confused. I was a boy. I wasn't a girl. Why was wearing girls clothes so exciting? I absolutely loved girls. I jerked off thinking about the girls from school and their cute skirts and ballet flats every single day. Why was I as turned on by me wearing the flats as them? Did that mean I was ga… Read more

I have a new fantasy I've been jacking off to. I get turned out like a whore by my wife. She takes me to a hotel room and dresses me up like a sissy. Then invites men to pay her money to fuck me. Man after man ramming my asspussy and mouth. Cumming in me and on me. Servicing dozens of stranger's cocks all day and night until she has enough money. Then make me sit in the car covered in cum as she drives me back home from the sleazy hotel. My mouth and ass still loaded with hot man sperm. She'd tell me "You're finally worth something to me you tiny dick little faggot! You earned your keep to… Read more

I grew up out in the country. Which isn't the best place for a young man to explore cross-dressing and becoming a sissy. But it was a nice place. And we had lots of open space, which is lots of open space to disappear and masturbate. About a quarter mile from our fence line there was a highway overpass that crossed a large creekbed. I had stolen and hidden some of my mother's clothes. I had a dress that buttoned up the front, a couple pair of pantyhose, and one of her pairs of black flats. I kept those hidden in a duffel bag in my closet. I would take that bag, sneak out and go to that overp… Read more

I've been watching a lot of pegging videos lately and a lot of videos where the man is being bottomed by the trans girl. I need to experience this. I really need to get fucked up my sissy ass. My tight hole is just craving being filled by cock. It's all I can think about. I finger myself in the shower and it's just not enough. I need to get pumped full of hot cum.… Read more

I've written before about how one of my oldest fantasies was to get caught crossdressing by one of the boys from school and then he and the other boys would make me their sissy. They'd gangbang me to make me buy their silence. So to keep the whole school from finding out what a sissy I was I had to fuck and suck them all. That fantasy used to make me cum so hard. It still does, really. But I had another one, too. One of the boys I fantasized about had a hot girlfriend. They were the school's "perfect couple". He was the good looking football player. She was on the dance team. She was beautif… Read more

I've been watching videos on here all day. I rubbed myself a little in the bathroom earlier and I am just dying to cum. I can't wait until I can blow this load and lick my cum. I wish masturbation wasn't so taboo. Especially in places like public bathrooms. Isn't that really a perfect place to let off some relief?… Read more

I'm a cocksucker. Some of the verbal humiliation videos that have been making me cum lately make me say it. And saying it out loud while you think about sucking cock really drives the point home. I'm a cocksucker. I just *LOVE* sucking cock. Short ones, long ones, thick ones, thin ones. cut, uncut. I don't care. I just love sucking cock. and the best cock is anonymous cock. I love sucking cock through glory holes. At least I used to. There aren't many around anymore where i live. The place I used to go to closed. It was an adult video store that had booths. Now, the only place I know that ha… Read more

A while back I posted about my "double life". i started watching some of the verbal humiliation videos. I didn't expect to love them but I do. I love those beautiful women telling me to be a cocksucker. Anyway, in one of them the woman tells me that the whole world would be so surprised that "one of the guys" is just a cocksucker. And it kind of clicked: I like the fact I have this secret. My crossdressing has been a secret forever. And I think the fact that it was something that no one knew that made it better. More exciting. More fun. Since watching that video I've been more conscious of… Read more

I'm going to have the whole house to myself this weekend. I'm trying to decide if I should go to the gay bathouse and suck some cock. Or just make crossdressing masturbation videos. What should I do?… Read more

Every time I watch my own shoe cum videos I can't stop thinking about how badly i want to suck my own cock. I wish I could clone myself and suck my clone's cock every day.… Read more

In college i had started experimenting more. My girlfriend at the time loved it. we'd invite some of her male friends and have bisexual threesomes. She just loved watching me fuck guys. She loved it when we'd suck a cock and share it together. She loved pegging me too. Because I was living alone at the time I had also made some clothes purchases. I had bought a cute little dress, some thigh high stockings, some lingerie tops, a couple different pairs of heels, and I bought my first dildo. I'd spend a lot of time dressed up, toying my ass, thinking about that cute boy from her dorm that used to… Read more

I've been sitting in my office watching videos of sissies riding dildos and getting fucked my men. I've been fantasizing all day about what it would be like to be a pretty sissy. To wax my body smooth, to put on makeup, to wear sexy girly clothes, and then feel that dildo sliding in and out of my tight asshole. I want it so badly. I want that to be me. Every sissy video I watch i want to be the girl in the video. Nobody knows this about me. Everyone who knows me thinks I'm a straight male but really I'm a cock hungry sissy on inside and she's dying to get out. I need to know what that sissy… Read more

My laundry machines are in a detached garage. I just went outside and then back in totally naked with just a pair of patent leather flats on while my neighbor was in his back yard. I'm pretty sure he didn't see me but the fact he could have makes me so hard.… Read more

I spent the long weekend toying my ass, jerking my cock, wearing hot heels, and eating my cum. And I had this question in my mind: How did I get here? I mean, it's kind of rhetorical. Did sissy porn make me the sissy cum loving bitch that I am? Or was that sissy bitch always in there wanting to get out and I saw the sissy porn and realized that was the way? I don't know. But I guess it doesn't matter does it? Either way, I'm crossdressing and eating cum and loving it and not going to stop now.… Read more

The cleaning lady is here at the office and I have my hand in my pants jacking off while she walks around the office emptying trashcans. She has no idea what i'm doing… Read more

So many cute outfit ideas! I've been wasting my work day shopping online. So many cute heels and outfits. I'm so horny right now imagining myself wearing these cute girly outfits and masturbating. I get so horny thinking about making videos of me and posting them here so others can see how much of a sissy I am.… Read more

I think the best part of being a crossdresser is when I see a sexy (trans or cis) woman I have to decide whether I want to fuck her or dress like her.… Read more