The Day I Lost My Virginity

I lost my virginity to a guy on my 21st birthday

I was out at a restaurant with a few coworkers. I don’t drink so we were just getting food. One of my coworkers friends was there. A guy who had just recently turned 43.

The guy was a runner in excellent shape. I went with him to another place then eventually wound up at his apartment near downtown Columbus

There in his apartment he fucked my virgin but with his big dick. I’d say it was 7 inches or maybe a tad longer. He knew my butt was a virgin so he was taking it easy at first.

Eventually getting me into doggy and giving me a proper pounding. His balls bouncing off my butt. He cummed in my butt. The feeling of a man cumming in me felt weird. Like I gave up my masculinity to him.

But afterwards we showered then headed out for a late night pizza. Afterwords I decided to head home.

A few weeks later I ran into him again and we had sex again.

I haven’t had anal sex since but I really crave it now

That's Juicy! 25
Remove It! 4

# 79915 - by Jon / June 21, 2025

by Anonymous on Jun 21, 2025 at 9:03 AM

I was a kid not even close to puberty when I gave it up to a boy that I liked in his mid teens. He was wonderfully gentle and talked me through it with lots of patience. On my tummy too shy to get naked he knelt between my smooth gangly legs slowly arranging my Calvin n Hobs underpants to expose my well shaped cheeky bottom.
The sight of my favorite underpants which he actually drooled on before he slid the back down got his excitement maxed as he hurriedly coughed up gobs of phlegm to use as lube. He'd never fuck'd ass , he was totally a panty wearing sissy and had a friend well into his twenties that broke his barely pubescent 12 year old boypussy in. That's a thing that I liked about him, his sweet defined taste in cute pretty panties which was my secret thing. Here I am in my cute little boypanty's being topped my first time by a beautiful twink in pink lace panties making me tingle all over. He coughed up phlegm three times trying to get in and then soothingly got me to relax and push back as instructed.
The tip of his thin boycock wiggled in and exploded a warmth that I'd never ever experienced and he slipped into my innocence till his puff of pubes nestled with my smooth quivering flesh. "Did you pee in me?" I shrieked and clamped down tightly. "NonoNo it's not pee it's cumcream!!!" He said excitedly. " What's cumcream?" I whispered seriously looking back over my shoulder.
He was all in still hard and here we were having a conversation about what cumcream was... "Sperms, jizm, man's milk " he said calmly, "You'll get some too when you get older." He said a matter of fact like. "I don't want any!" I replied making him laugh and ask again "Does it hurt at all?" "Uh ah, nope." I replied weirdly enjoying the strange feeling being fucked, the rocking motion pushing rhythmically making me feel the cool wet grass soak through my underpants wetting my little erection. He fucked n fucked answering my questions and then he came a fabulous ejaculatiom filling my tight boypussy with warmth making me feel so relaxed. My tight little boyc**t quivering in dry orgasms. He slipped out, kissed both cheeks and rearranged my Calvin's...
" Can I get underpants like you got now," I asked making both of us laugh "Really pretty one's too!"

(3) (0)

by Anonymous on Jun 21, 2025 at 1:11 PM

1st time I rolled over and got on my hands and knees all i could say was "you've got me" over and over that and " my ass belongs to you" since then ive gone to my fuckers house to suck his cock and he knows all he has to do is softly begin spanking my ass and I roll over and wait for him to impaled me on his hard cock again.
He rolls me over and I watch as he thrusts that cock in and out of me while I grab my legs and take it missionary style

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Comments

by Anonymous on Jun 21, 2025 at 8:30 AM

yep once you cross that line and find out how pleasurable it feels you crave it. Same with having a cock in your mouth and cumming on your tongue. I love pussy but at times crave cock.

by Anonymous on Jun 21, 2025 at 8:40 AM

I love bottoming, and I’m not a sissy, please hammer my ass.

by athensgold124 on Jun 21, 2025 at 8:52 AM

You had a nice first time with a nice man and a follow up can't get any better than that, some men get really rough like the want to tear you in two.

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