Crossdressing Freak

by Getoutofmymind

13 Sep 2023 1898 readers Score 8.2 (11 votes) PDF Mobi ePub Txt


I have a huge cigarette fetish. I have had it since I was seven or eight. I’d sneak into my mom’s cigarettes and pretend to smoke them. I would also sneak into my mom’s things, her bras, panties, and most of all her tall boots. So now, being grown I’ve become a crossdresser, passable too, and when I dress, I smoke. These two fetishes have made me a complete freak and an exhibitionist.

I began dressing when I could. I got very good at it. The makeup, the hair, the walk and talk, even big tits. I also started smoking when I was alone especially when I masturbated. And because of this I almost can’t cum without being dressed and smoking, unless I’m being fucked by a sexy man with a hard dick, then I can’t stop it. I don’t even need to be sucked or jerked off, I just cum…a lot!

Men kept telling me how much I looked like a woman. Even my face, hands, and feet look like a woman and not a man. I began believing them and looking in the mirror I could see they were right. I wanted to see how right we were by going out which not only was scary but extremely exciting.

I did little test runs at night. The first time driving with high heels is challenging. I smoked and drove around soaking myself and the seat. The feeling of the seat belt between my big tits and them bouncing when I hit a bump sent my head spinning with excitement. When I got home, I fuck myself like crazy.

A few weeks passed before I gained the courage to do this during the day. I dressed a bit more conservatively, not showing as much cleavage and legs.

Driving around in the daylight hours was the most exciting thing I’d ever done to that point. I made sure to wear panties under my skirt, but I’d soaked them so much that after about ten minutes it looked like I’d pissed myself.

I drove to a park I knew about. I drove right up the pavilion and got out and walked around under it because it had begun to rain. With the sound of my heels on the concrete and being outside, I fought not cuming.

I was smoking like mad, hornier than I’d ever been in my life when a car pulled in and parked at the pavilion near mine. I sat down quickly when I saw the door begin to open. I peeked over my shoulder and saw a man walking to one of the tables under his pavilion. I couldn’t tell if I was more horny than scared. I was literally shaking so badly that lighting my cigarette was difficult. I sat there with a million thoughts running through my head. I realized if he thought I was a woman he might try a come over and talk to me. That was both scary and exciting. I lit a new cigarette and got up and walked around under my pavilion. The rain was still coming down but lightly. I’d look over his way and he’d look away. I made sure to stand so he could see my big tits. But after several minutes he made no moves to make me think he was going to come over.

With the darkened skies of the rain, I felt bold. I sat back down only this time on top of the table with my feet on the seat and facing him. I lit a new cig. and spread my legs so my hot pink panties could easily be seen. He was pretending not to look but he was and so I put the cig. in my mouth, stood up, and slowly pulled my panties down to my knees. Then I sat back and took them off completely. I made sure he saw them in my hand and put them on the table. I spread my legs wide open and when he saw I had a dick and not a pussy he didn’t hide the fact he was looking now. This was a fantasy come true for me and I was going to let him see how horny I was.

First, I played with my tits then I stood up, pulled my skirt, and began humping the corner of the table. He had pulled his dick out now and was stroking and watching. I wanted to invite him over to fuck me but this was too hot as it was. I’ve always been an exhibitionist but not dressed as a woman. This was much hotter than the “normal.”

I sat back down like I’d been sitting, lit a new cigarette, and started slowly running my long nails up and down my dick. He was still stroking his. I wrapped my hand around my dick and started stroking mine in the rhythm of his hand. I’m a very noisy fuck and I made sure he could hear my little girly moans which weren’t faked. I was so close to cuming and I managed to keep it from happening for a minute or so. The situation, me smoking, and him watching was too much and I exploded shooting cum straight up and on my skirt. I came so hard my legs shook and I couldn’t keep the open. When it was over, I looked, and he was zipping up. If he came, I didn’t see it because I was in my own little world.

by Getoutofmymind

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