My Peak Of Being Gay

I spent the 80s in my teens and early 20s…as confessed before I was in the closet. I used to wear lingerie and dress girlie when I had sex with men, usually much older. It wasn’t as readily available as it is now but I would have probably transitioned. Sadly I ended up loosing my feminine and boy band good looks to aging and testosterone. By 30 I didn’t feel sexy anymore and dress up didn’t have the same appeal in my opinion and was relegated to being a closeted gay man for the rest of my life. Even if I came out now what’s the point. I still occasionally hook up but in hindsight I would have been happier being who I was.

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# 64838 - by Mikey / August 14, 2025

- Gay Confessions -

Bi-Sexual Male / 50

Turned Out Part 2

The following summer I resumed working for my dad. It had been months since I had any sexual encounters with a man. The guy who worked for him was obviously still hot for me, every chance he got he was playing with my ass and feeding me his cock. Being a submissive fem boy I happily indulged him. My dad thought he’d have this guy man me up and instead he was turning me.

Since my dad was usually at the shop late he suggested this guy drive me home…so he tells my dad he’d take me bowling. Instead we’d go to his house on the way we stopped at a drug store and he bought some nude small panty hose. He said these are for you! I had spent the school year masterbating about men and it was exciting to have the real thing again. He had not fucked me yet but that would soon change.

I’d put on the panty hose and my tee shirt and I’d get in bed and suck him all the time. He’d rip a hole in them and finger my butt. Sometimes he’d play with my little dick at the same time and I’d cum. I’d go home and she’d ask how I liked bowling and in my mind I thought about the things I was doing then my mouth would come some story.

Next time he drove me home we were kissing and he lifted me up and asked if I wanted him like a girl, I said yes please. I had a new pair of panty hose and this time a tank top which he tied in a knot around my waist. I said should I wear lipstick? And he said well it’s hard to get off but if you want I makeup I’ll get some for you. We got in bed and he ripped a hole in the panty hose while I sucked him. He put lube in my hole and worked my boi pussy and told me how to relax.

He wasn’t huge around but it was kinda long. He was patient, I was nervous but once it was in it felt good. I rode him and could see myself in the mirror I looked sexy. He came and it was such a turn on that I did that. All summer we did it and my collection of girl stuff at his house grew. He took me to meet a friend of his and he had me too. I was really taking to this life but no one knew it was my secret.

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# 64829 - by Mikey / August 10, 2025

- Dark Desires Unleashed -

Bi-Sexual Male / 50

Turned

My dad owned a shop and I started going to work with him. He assigned one of his guys to help me find something to do. He was a older man I never met actually.

I was walking in front of him in one of the storage buildings and he was grabbing my ass. Then not long after he sat me in a chair and pulled his cock out and tried to get me to suck it…I really didn’t know what to do, I never did it. It seemed at the time I was maybe fem, I was cute , smooth and all but inexperienced for sure. Then I ended up getting my shoes wet, dad told him to take me to I think k-mart and get me new ones. All thru the store he was up my butt. I didn’t say anything I was just submissive or whatever. On the way back we got caught at a train and he whipped it out and wanted me to lick it…he slipped his hand in my shorts and went to town on my butt.

I never told anyone what happened…the aftermath was that my attraction to men went into overdrive.

I started going to work with my dad more often that summer the guy who worked for him was relentlessly wanting me. I started giving in a little more. By the time school started back up and I had done quite a bit short of anal sex but he did hump my butt n came all over.

First time I admitted this, I think this was the thing that really cemented my sexual identity more than anything.

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# 64828 - by Mikey / August 10, 2025

- Gay Confessions -

Bi-Sexual Male / 50

Closeted Regret

I have been bi my whole life and living 2 separate lives for most of it.
When I was a teen I liked girls but I also was attracted to men…older men. I fit into the perfect twink appearance cute face, nice butt etc.
No one among my friends, family, girlfriends knew I had a penchant for wearing hosiery and getting fucked by men in motels or in their beds. Once a couple occasions I was gang fucked. I loved it all and I was torn about just being completely gay or go the other way. From my teens into my 20s was the most fun I had in my gay life, when I got older I stopped all that, got married and all that. From time to time I hooked up but it was never the same as when I was younger. My biggest regret is that I just didn’t live how I think I was meant to. At the time we didn’t have the access to things like now. I would have taken hormones and feminized myself as much as possible because I just loved the idea of men using me as a fem. Just born at the wrong time I guess.

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# 64827 - by Mikey / August 10, 2025

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