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Regrets
There were 3 times in my life that if I had the opportunity to relive, I absolutely would and do things differently.
First. Growing up, there was a boy down the road who was maybe 3 years older than I was. I was (maybe) 8 and he was 11-12. He wasn’t particularly attractive, but he wasn’t exactly unattractive. What he was though was hot for younger boys. He was larger than me enough that I know had he wanted to he could have dominated me. I wish I had known enough to seize the opportunity to suck him off, which may have led to anal sex. But it never made it past him stripping me and making me stand still while he inspected my genitalia. How I wish had perused it. I’m 56 and have still never been sodomized and I think to this day I crave a larger man to have his way with me, me being in complete submission because of this older boy.
Second. I had a best friend around that time who I had regular sleepovers with. He liked for us both to lube our fingers and explore each other’s anuses. I was too young to consider having him put his penis in me. I wish I had known more then.
Finally, in highschool, a number of us were at a friends house drinking. One of the guys (who turned out to be bisexual) got really hammered and took off all of his clothes and offered to swap blowjobs with one of us. Nobody took him up on it but I’ve wished I had isolated him somewhere, blown him for a while then mounted him up and ridden him. He had the second biggest dick I have ever seen in my life.
I’ve spent my entire life wondering what impact all 3 of those incidences may have had on the trajectory of my life.
And I still want to get butt fucked by a very large and physically superior man.
I was 10 an gave up my anal virginity to a 15 year old boy and was a little confused but basically enjoyed it. I'd been being groomed by the older boy next door but he creeped me out too much to let him do it. He'd been always sticking his dick in my mouth since I was 5 and tried fuck'n me when I was 7 but he couldn't keep it in my tight little butt because the penetration hurt and I'd wiggle about so much he couldn't get more than an inch in.
I don't have many regrets in my life but I guess everyone has some. First regret would be that I was Molested and raped by a family member starting when I was 10 years old. Second would be that I only had sex with guys until I was 19 years old when I met my wife. I am thankful that she knew that I was bisexual before we got married and she was expecting to that. I don't regret are open marriage we have together but I often wonder what it would have been like to have a normal marriage with her. I do enjoy having sex with black men only because they are more sexuality opened minded and love fucking white men in the ass. All in all its been a good life I guess.
I had a sleepover with a friend in middle school. He kept scooting closer to me and then finally asked if I wanted to sleep in the same sleeping bag. We ended up naked and fooling around. He gave me my first blow job.
We both ended up dating girls, getting married, and having kids. But for a few years in school I enjoyed his mouth around my cock. He offered me his ass once but I didn't feel comfortable. Looking back on it I wish I had fucked him.
I was a cute little assfuck of a kid from 4th grade. I moved from the city to the suburbs when I was 12 and the necessary showers in school were so scary. I was worried about what the older boy's said about me and how I looked naked "cute I just gotta hug you, especially that butt that looks like a fuck'n butt!" I never really understood what a "fuck'n butt" looks like but I thought "Can they tell what Willy, Joey and Nicky's been doing to my butt?" Definitely, I was attractive to them but only a few were attractive to me and I became fast friends and at sleepovers I became the "go to" to spoon. Jamie's like the nerdy'est kid ever but the most developed of the already past puberty boys I seemed to like. He was the one who spit on his hand twice, rubbed it on his dick while I pretended to be asleep in my tighty-whitey underpants wrapped quivering boycheeks. Yes, I wanted it and his spoonful of an erection had me whimpering and pushing back against him as I shyly pretended to be asleep...
The only time I ever had a threesome was with him. I guess I felt comfortable with it because we had been naked together and he had sucked my cock multiple times. We spit roasted the girl down the street when we were all in high school. Took turns fucking her mouth and pussy back and forth until we put her on her knees and both came all over her face.
Pot's availability in high school seduced a lot of cute new freshman boy's ass's and I was one of um. I guess that's why they called us "freshies," fresh smooth little ass's and fresh faced rosey cheeked little wide-eyed pouty lipped suckers.