Suppose I might as well greentext the first time I went all the way
>in high school
>me and this buddy of mine have been fooling around for a couple years
>we're "not gay"
>so we've got all these boundaries
>no kissing
>no sucking dick
>no taking it up the butt
>stuff like handjobs and frotting were okay though
>and eventually we relaxed enough to start "fucking" each other between the thighs
>this inevitably leads to us doing "just the tip", teasing each other's limits
>one day I'm doing this to him
>and we're both super fucking horny from like an hour of messing around
>I keep working my dick deeper and deeper
>and he's not stopping me
>he's blushing and hiding his eyes with one arm
>but his dick is still hard
>and he's making noises like he likes it
>next thing I know, I'm balls-deep
>fuck this feels amazing
>ask if he's okay
>he mutters that it feels weird, but doesn't hurt
>I start rocking my hips
>he whimpers a bit
>but doesn't tell me to stop
>I pick up the pace
>whoa, this is it
>I'm actually fucking someone
>I'm losing my virginity... I'm taking his virginity... holy shit
>try to hold out, but I don't last very long
>maybe a minute at most
>when I start cumming, the thought of pulling out doesn't even cross my mind
>I *need* to push my dick in him as deep as I can
>I *need* to fill him with my cum
>after I finish and come back to earth, he's looking up at me with huge eyes
>says "did you just cum in me?" in a shocked voice
>oh fuck, I took it too far, he hates me
>start apologizing and moving to pull my dick out out
>he makes a strangled sound and stops me, holding my hips in with his legs
>tells me to just wait a second
>he starts jerking himself off
>with my half-hard dick still up his ass
>only takes like 20 seconds before he cums
>and he shoots like a fire hydrant, all over himself
>clenches on my dick so hard it kinda hurts, tbh
>makes me feel like a fucking stud though, realizing he got off on what I just did to him

Been hooking up with this hung twink lately. We started out as gym buddies. Then one day I invite him over to my place for a post-workout joint.

I legit was just trying to be friendly, not trying to pick him up. Didn't even know he was into guys. But I guess he got mixed signals... once we got high and relaxed on the couch, he just casually starts kissing and touching me. I was surprised, but... he's a good looking guy, and I'm horny, so I roll with it.

He's not the first guy I've ever hooked up with, I had a buddy I used to trade BJs with back in high school. But this guy is better at pushing my buttons... or maybe I'm just more mellow or less insecure about trying gay shit than I used to be. Cause after our first couple hookups, he talked me into bottoming.

He's hung like a fucking donkey... looks fucking massive on his short twink frame. Honestly I didn't think he'd be able to fit it in me, not with me being an anal virgin. But he promised he'd pull out as soon as it got to be too much, so I let him try.

Turns out he really knew what he was doing. Took it really slow, spent like an hour edging me while patiently working his dick in a little bit at a time. I thought I'd maybe be able to handle him halfway at most before I wimped out... but before I know it he's balls deep, and it still feels fucking good. Then he starts rocking his hips, and I realize holy shit, I'm really getting fucked by another guy and loving it. He kept jerking and edging me, and while I didn't exactly have a prostate orgasm, he managed to time it so that I came at the same time he did.

So yeah. Been hooking up with him for a few months now, and feel like he's moved me at least a notch or two up the Kinsey scale and is turning me into a full-blown bottom. If you saw us together you'd totally guess it was the other way around cause he's shorter and got a smaller frame than me, but I just can't get enough of his dick.

>>29262335
>I've tried sitting on it
There's your problem. Riding dick is a rookie mistake... virgin bottoms always often start out that way cause the position gives them maximum control and the ability to easily back out. But it also makes you tense up; it's impossible to fully relax yourself when you're balancing and supporting your own weight.

Best bet is to try a position where you can fully go limp. Prone bone is easiest for the bottom IMO, but more effort for the top. Missionary (like picrel) is a bit more awkward on angle, but lets the top relax and take his time slowly working it in. Any position where you're bent over a table or bed can work too... the main thing is you want to just go floppy and focus on relaxing your ass.