First time anal with 18yo twink
TLDR: had a boy from grindr over and ened up fucking the shit out of him for an amazing first anal experience.
I'm bi, 26 NB but very masc presenting, 191cm 115kg bearded, hairy guy with a kinda fem lesbian haircut.
I've been with a good few guys before, but most were trans guys and those who weren't, we just didn't do anal. I have just broken up with my gf of three years and see this cute boy with long dyed hair pop up on grindr.
I have a thing for androgynous people and he was very attractive to me. A little bit chunky but in all the right places, kind of hairy but he shaved his plump ass. He was like the Wartortle to my Blastoise.
Anyway he pulled up at my place and i smoked a blunt and we started making out. He sucked my dick in the living room before we decided to just head upstairs.
Not trying to brag (I am), but my dick is pretty big and this boy was swallowing it no problem. He actually called my dick "magazine worthy" lol.
We get into the bedroom and start making out heavy with our clothes off. We frot with my big thick dick and his little skinny one and i can tell he really enjoys it. He then asks me to eat his ass.
This was something i'd only done with my ex so i was a little nervous but when his big round ass and tight little hole were in front of me, something came over me and i got really into it.
I have a short tongue but stuck it as deep as i could into his hole. He was on all fours, bucking his hips back and forth, pushing his ass into my face. I played with his cute little dick and balls from underneath.
After i came up for air and saw how open his hole had become, i knew i was going to fuck him. I asked him if he wanted me too and he said yeah. Consent, yk? I had condoms and lube but for my first time anal to be with a cute plump 18 yo ass, i simply had to feel it raw.
I regret it now because this boy was clearly a slut by how well he took my cock. It's 6 inches usually, but gets up to 7 when I'm really horny, which i was. It's quite thick, gets wider in the middle and is straight with an upward curve.
I went slow, but he took it all the way in like a champ. It wasn't long before i was pounding him into the mattress, choking him and biting his neck. Eventually i had to tap out because it's hot out and I'm a little out of practice so my stamina's not all the way there.
I was surprised by how it felt. I was never thar fussed about anal because i don't like poop and i love pussy, but he was really tight. I still think i prefer pussy tho, it has more texture. Maybe i just need to collect a larger sample size.
I'm on SSRIs so i don't really bother trying to cum w people, but it would have been nice to oblige him when he asked me to breed his hole. Instead, he straddled me and he jerked off and frotted with me. I played with his nipples and choked him and put my thumb in his mouth for him to suck.
He ends up cumming on my chest and grabs my hair to try to pull my face into the splash zone. I've never tasted a guy's cum before and there was quite a lot for such a little dick, so i was a little nervous and didn't really want to do all that.
But i couldn't help myself and strained my neck to lick some of his creamy cum from the tip of his little penis. The cheeky wee fucker then pats my head and calls me a good boy. Why was that so annoying yet so hot???
Well in the end i win because he sucks my dick like crazy for another 10ish minutes while i smoked the rest of my blunt in bliss. Feel weird about the age gap and i'm gonna get tested but it was nice to be a bit of a heathen for once.
Posted Aug 14, 2026, 12:31 AM UTC