I Liked It From The Very First Time

I went to college at a small rural college in the Texas Panhandle. It was a 'kicker' town and the only fun there was playing pool at this pool hall. No one ever checked any form of ID at that time, if you had pimples you were a kid, if you had sideburns you weren't. It was that sort of place. Beer came in a bottle, no self respecting kicker drank beer out of a can. I was a good pool player, better than most and hung out there most weekends.

I'm playing pool and there is this guy who is not a college student. He is older and looks like a pool shark, he brings his own cue. He's hustling. Some of the guys put me up to it and tell me to take him on, and they put up the money. I lost and he told me he would go double or nothing. If I lost again I gave him my ass. To be honest who ever heard of that in my growing up and didn't even know what he meant by that. I lost. He got his 'ass' out in the parking lot.

I had to suffer the humiliation of having been fucked by the pool shark. I got a lot of questions about what it was like, did it hurt, how did he do it. I told the truth, why lie about it. He did it over the tailgate of his pickup, it did hurt. I didn't tell them that I liked it. I didn't even know I would like it. Or that I wanted it again. No one where I grew up ever saw or knew a gay guy. I was pretty sure I was after loosing to that pool shark.

My next big step was confronting a dick head on. In my face, opening my mouth for it. That happened with a man that worked at the feed store. I would guess he was in his sixties, but men like him age because of the sun and work. Either way he was 'old Army', and he smelled that I was a likely cocksucker. He held my hair in his hand to lift my face up and forced his dick down my throat in one big shove. I gagged and spit up. He gave me a rag to wipe my face and shoved his dick down my throat again. Holding my head with both hands he face fucked me and I guess you can say I swallowed. Now I had taken it both ways. I was gay, I knew it. I liked it. I went to the feed store and hung around until he came to get me.

I left college with my degree in business and went to work in the finance department of the John Deer dealership. The old boy there, a guy named Russel, worked in the parts department. He 'nailed' me up against a stack of tires and got my sweet ass for it. He was the fuckboy and I was the sweet ass boy in the relationship. I worshipped him, I guess I was in love with him, and I went to his place and played around naked. I sucked his dick with pleasure and spread my cheeks with pleasure. He called me 'Chrissy', like a girl. It's the first time I wore panties, that he stole from his sister who stilled lived at home.

I can go on, I went to the West Coast and boyfriended to this man who wanted a boy in panties, I sucked his dick and gave up my ass to him. I told him my name was Chrissy and I wore panties. He dressed me up as a girl and took me out to bars and kissed me. It was his way of testing the establishment by kissing a boy in public. I guess it was a good thing that I wasn't a big guy, 5' 7" and weighed around 140 at that time. And I could get made up real easy. I liked being a girl, dressing up as a girl, opening my legs like a girl (he fucked me like a girl, on my back with him between my legs). Sometimes I wished I was a girl.

This became a real problem as I grew older and had to stop dressing up as woman. I just didn't look like a woman, and since I had grown up in cowboy boots I didn't walk like a woman. I went straight gay and met a 'sailor', he was divorced and liked having me around. That was my first 'long term relationship'. It's hard for me to maintain a relationship like that now, I am more of a man that looks for casual relationships, I know all the gay bars and places, and hang out there and go off with some stranger. I take precautions, but truthfully everyone takes precautions now. I'm still Chrissy when I have a man pounding my ass, or I'm sucking on his dick.

Comments

Anonymous

by Anonymous on Mar 30, 2025 at 10:20 AM

My brother in law wears panties every time we get together. They are his wife’s and are always dirty ones.

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Anonymous

by Anonymous on Mar 30, 2025 at 6:43 PM

I've been a cute panty boy since I was a kid who was teasing the boy's without trying. Momma always dressed me kinda girly and the neighborhood boy's had me suck'n in 3rd grade and one particular nice highschool boy sweetly and delicately started fuck'n me at 9. Moving at 12 opened my horizons needing the same thing that I'd become accustomed to, passionate loving. I'm 18 and I recently met my first ever boyfriend and I came in my lace panties just hugging abd kissing him and so did he gosh isn't like especially great!

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