I often wonder what it’s like to be a woman. I fantasize about it a lot.
This isn’t so much a story rather than my own fantasy. Unlike the other stuff I’ve posted here, this is actually true. A little dive into my mind I guess.
I was an only child raised by a single mother. I was always a loner and didn’t have many friends and my mom and I were kind of close. I didn’t so much fantasize about having sex with her but I was curious about seeing her naked. I would spy on her in her room as she dressed or when she’d shower. I would try to sneak peaks at her as she slept. The few times my dad was in the picture I would spy on them while they had sex. My mom was a dirty sex talker and the things she said turned me on in multiple ways. The obvious one in that I was a male and it sounded hot hearing a woman saying things like “oh God, you’re cock is so deep!” Or “lemme ride that big dick!”
There was another part of me that was curious as to what it was like to be her. Having my dad’s cock deep inside her. What did it feel like?
Around the age of 12 I started snooping through her closet and dresser drawers. I loved finding her nightgowns and lingerie. At first it was just out of curiosity on seeing it on a person. Holding up a see through lace piece of lingerie doesn’t do it justice, but seeing it on a body does. So I’d put it on and stand in front of the mirror. I’d get so turned on by the sight.
By the time I was 14 I had taken a few of her nightgowns and lingerie that I knew, or assumed she didn’t wear anymore based on how deep in her closet they were. I would sleep in them. Just once in a while at first but the more I did it, the more I liked it and the more I did it. I loved the feel of the silk nightgowns on my body. I loved wearing her panties. It felt more comfortable to wear women’s clothing than it did mine.
When I was 15 my friend came out to me. When he told me he was gay, I wasn’t shocked. Everyone knew. Once it was in the open, I started thinking about it more and more. It wasn’t long before him and I were fooling around. We’d have sleepovers almost ever weekend and we’d sleep naked together and just blow each other. It was exactly what I needed at that time of confusion. I got both of what I was feeling. I got to feel like a man when he’d suck my dick and I got to feel like a woman when I sucked his.
I always thought about, and we always talked about trying anal sex together but it kind of scared both of us. Me more than him, he was a very feminine gay guy, I was, well I don’t know what the hell I was.
I eventually told him of my cross dresser fetish or whatever it was. It got to where I’d wear nightgowns and lingerie to bed when I was with him. It was eerily satisfying to wear lingerie and suck his cock. I’d even gone as far as having him call me a woman and I had a woman’s name for myself. Stephanie.
We eventually got to where we had anal sex but I always “topped”. I never worked up the courage to let him fuck me. Not long after that, the whole thing fizzled out as I found a girlfriend and didn’t think about him anymore in that way. I still dressed up as much as possible though.
When I was 18 I found a dildo in my moms dresser drawer. I was shocked at how big it was. Granted my mom was a thicker woman and probably needed a bigger dick than a skinnier woman would. I worked up the nerve to try to insert it inside my ass one night when she was out on a date. It didn’t go so well. It was WAY too big. I did go to the sex shop and buy a smaller one and got used to inserting it in my ass. When I was used to it, I bought a male blow up doll that had a dick on it. I’d blow it up, put some lingerie on and lay in bed next to it, and eventually have sex with it. I’d even say dirty things I remember hearing my mom say to my dad.
As I’ve gotten older the cross dressing has stopped. Especially now since I have a wife and kids and my wife wouldn’t understand anyways. I’ve been thinking a lot about it though and how if I were a woman with the sex drive I have now as a man, I’d be getting fucked constantly.
I have fantasies about being a woman, having a man playing with my tits. Running my fingers through his chest hair as I he slides his cock inside my wet pussy. The feeling of his cock deep inside me going in and out. Then I think about how one man just wouldn’t be enough. I have a pussy, an asshole, a mouth and two hands. It’d take five guys to get me off completely. I’d let them do anything they wanted to me however they wanted to do it!
Now would be a good time to explain that I have ZERO interest in a sex change. That’s definitely not who I am. I love being a man. I was blessed with an above average size dick and I know how to use it. But sometimes I just wish I could be a woman for a day and just get fucked all day long. I’d have so many dildos and vibrators. I may never leave the house if I had a pussy and tits.
I’m not sure what any of this means. What am I? Who am I? I don’t know. The only conclusion I have is that I am a man that enjoys fucking women and I wish I could be a woman sometimes so a guy or 5 like me could fuck my brains out.
All of this is true, and if anyone has any real advice or suggestions, by all means, please leave them in the comments. I could use any help available. Thanks for listening.