Unexpected Anal

This took place quite a few years ago in my late 40's. I had been bisexual since a sleepover when I was 14. I married at 27, but still would secretly suck cocks. You could say I was a bit of a cock sucking slut. I posted an ad looking for a gay couple so I could suck more than one cock during a hook up. I got a reply from what seemed to be a nice gay couple that invited me to meet them at their place. I accepted we set a date. I arrived at their house which was somewhat secluded so they were outside naked. This kind of shocked me, but I enjoyed being naked outside as well, I live in the country no neighbors. They invited me in so we could chat before getting started. They made me feel very comfortable, and soon we were off to the bedroom. I stripped then got on the bed. Ben joined me asking me to suck his cock. I took him in my mouth sucking him making him moan with pleasure. "Oh Bob your really good at this". I just kept sucking. Then I felt a tongue on my ass. I pulled off Ben's cock, and told Frank I don't do anal. Frank replied relax i just want to eat your ass I'm not going to try to fuck you. It did feel good so I said ok keep going. I returned to sucking Ben's cock. Frank stuck a finger in my ass asking if I was with it. I just moaned around Ben's cock because it felt nice. Soon Frank added another finger then another. Frank had 3 fingers in my ass, and was pumping them in and out in a fucking motion. Suddenly Frank pulled his fingers out , and my ass felt empty. Then Frank inserted a small dildo in me again using a fucking motion. I have to admit I was loving the sensation. After a few minutes of this Ben pulled out of my mouth. "Bob I think you're ready for your first cock in your ass and it's going to be mine". At this point I was still nervous, but my horniness won out. I replied " yes Ben give me your cock" . Ben wasted no time as Frank pulled out the dildo Ben's cock was there to penetrate my ass. Ben's cock was bigger than the dildo , but he was lubed up good and he slowly started to slip in. I was amazed how good it felt once he was all the way in. Ben let me adjust for a minute then started fucking my ass. I loved the sensation, and I got impatient. Ben was going to slow for me I started fucking back on his cock. Ben picked up on this and started pounding my ass. Frank had somehow gotten underneath us taking my dripping cock in his mouth. Frank knew how susck a cock because I exploded in his mouth within a minute of him taking me in his mouth. This caused my ass to clinch as I was cumming driving Ben over the edge. Ben grabbed my hips and buried himself deep in my ass as he came. I never thought getting fucked in the ass would feel so good. I continued to meet them for a few years, but somehow we drifted apart.

Comments

Anonymous

by Anonymous on Sep 30, 2025 at 9:35 AM

My first man fuckn happened at the tender age of 18 after highschool graduation with my bestie's gay uncle Jake. He was so great gently fuckn my tight cherry ass Jimmy my friend had been trying to fuck me unsuccessfully since 8th grade. Now I really wanted it more Jimmy. Talk about going through a boyslut stage I was suddenly a insatiable
Panty boy ditching my white cotton underpants for satin and lace.
Talk about a profound effect one cock can have on a cute cherry ass???

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Anonymous

by Anonymous on Sep 30, 2025 at 9:50 AM

I’m a bottoming cock sucking whore. You don’t even need to return the favor as long as I get fucked and full of juice.i love leaking as I drive home.

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Anonymous

by Anonymous on Sep 30, 2025 at 2:03 PM

My neighbor fucked me. I'd been secretly sucking his cock for a few months. I'm a mature DWM turned cocksucker, seems rather common. When we first stated he dais he was going to train me to be a good cocksucker.
Last week I went over and he told me to get face down and ass up, that I needed to be fucked.
Hurt for a bit but what a feeling. He is a masculine top man, and seems now I am his bottom.

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Anonymous

by Anonymous on Oct 1, 2025 at 9:24 PM

I found out at 19 that those unexpected cocks shoved in my ass were like the best fucks ever. I'd been Gary's fresh faced boy squeeze since I entered my teens and he being a few years older he easily seduced me. Gary wasn't the best lover but I felt obligated for some reason. He likes replaying our first intercourse where he literally ripped the ass of my underpants to stick it in hurtfully. I have to tell you that those hunks in our lakefront condo kinda rule my panty wearing boypussy for sure. I never thought quickies were so good but they really are.

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