How Did It Feel The First Time You Penetrated A Guy's Ass?

[pnwboy]

My first sexual experience was with a straight man who had never messed with another guy. Our first time together was incredible beyond words. He told me that no woman had ever felt that amazing and has been addicted ever since. Does it really feel so good that you'd choose a guy over women now?

 

[halcyondays]

lol... it was like pushing up against a wall until he relaxed his hole and my head popped into his tight sphincter... I think we both said something like "oh fuck!" It was like someone was squeezing my head in a fist.

I learned later he relaxed his sphincter by pushing like he was defecating. Only difference was that something was on the way in, not out.

BTW he was on top controlling how much of me he took how fast. He squealed when he pushed down and took a little more of me. My head slid into his rectum which was not as tight but still quite snug. The tight band of his sphincter slid further down on my rod as he worked his way on. He got off several times and applied more lube. I had to hold the base of my cock to keep him from injuring me.

Took a while but he worked his way all the way on. With all the squealing, whimpering, gasping and moaning I wondered if he was dying. Once he was comfortable enough he bucked and romped until he squirted all over my chest and belly.

I was 22, he 20. It was 1984. HIV/AIDS was hitting planet sex hard. The body count grew by the day. Reminiscent of covid today.

Men over women because of it? No, but I did start topping guys now and then when opportunities presented themselves.

 

[diver6]

It was the best thing ever!! It was the first thing my cock was in and felt amazing! My buddy and I fucked each other for years before we ever experienced a pussy. Been trying to get back into an ass ever since!

 

[thomas200]

like a vacuum

 

[1NiceRod]

I loved it. It was a nice tight hole that milked my cock for 15 minutes before I blasted my load deep in his ass. The slickness of my cum in that tight hole was even better.

 

[gsoler]

It was both amazing and terrible at the same time. I loved the tightness of the annus I got to fuck, but he was so dirty (he hadnt rinsed before I fucked him) that I end up vomiting when I went back home. Because of that I thought fucking men wasnt for me so I married a woman.

 

[Lakeshore]

It was amazingly tight and felt great, better than any pussy I'd had up to that time. I slowly pushed my penis head against his lubed hole and it was a bit of a struggle to push in. When it went in I made sure he was fine and penetrated him fully with slow insertion and plenty of lube. I blew a load deep up inside his butt and we continued to do it all that summer.

 

[curtdude]

Michael and I were changing from swimming in the pool we were both naked he put his hand on my shoulder and balls we fell on the bed I was on top he lifted his legs up I looked into his eyes he nodded his head I put my penis against his hole it was tight I pushed in I saw him grimis face pain my head popped through his hole it felt tight and warm I inched in balls deep did him until I injected my load deep inside him we did it many more times through the summer

 

[BlackIsKingSize]

Straight sex was actually disappointing for me. I thought maybe there was something wrong with me or sex just wasn’t as great as people say. I’d get off but it was like ‘jerking off is easier and gets the same results.’ But I did enjoy foreplay and getting the girl off. Fucking I could take or leave.

But the first time I fucked a guy was life changing, it felt like nothing I’d felt before right from the start of penetration. I’m sure it was a combination of the tightness of an anus and the psychological element but I knew right away this was what I’d been missing.

 

[Philly swords]

I HAVE to know what it feels like sliding in a dudes ass fucking raw!!

 

[Ohiojohn]

Took a bit to actually get my dick in my friends butthole. He was a virgin so he was very tight and didn’t know how to relax. Once I popped in it was so tight and warm on my dick. He let out a big moan.

 

[davecray]

first time I topped it was with a man with a smaller build - he led the entire experience. after we showered I lie on my back and he was between my legs getting me hard - he slipped a condom on and lube me up then just sat on it - most amazing tight feeling as he slowly lowered his ass down my shaft - I had just fucked my girlfriend the night before and his ass felt tighter - after he got use to my thickness he bounced up and down moaning with pleasure while jerking his own cock - after about 15 minutes of him riding me in this position the friction was too much and I shot my load up his ass while he came on my chest - he slowly climbed off and cleaned us both up then, much to my surprise, he had me sit on the edge of the bed and got on his knees between my legs and slowly sucked another load out of my sore cock - great first experience topping - my preference is to bottom but have topped a handful of guys and it has felt great

 

[elklindoxxx]

Sticking my dick in a rubber tube. Very tight.

 

[lowhangers]

Hav't tried at the moment. We only strike

 

[thongboy]

The first time was a disaster. I thought it was macho not to use a lube.

 

[svendiff44]

It felt amazing. He had only bottomed a few times and never for a guy my size. I loved how tight it was especially how it stayed really tight the whole time we fucked. I came like crazy

 

[Jar12]

It hurt at first. But after extra lube, felt amazing. Does give you an illusion that might have to use the bathroom

 

[Tight_End_SC]

It was amazing. He really wanted my dick inside him and was not new to taking cock, so really no issues with getting balls deep inside him. As I recall, I kinda teased him a bit at first and did not just ram it in. It was truly a case of nature taking it's course. Never had I screwed a woman in the butt so I was excited about taking his ass. It was TIGHT!

I don't think I lasted five minutes, it was amazing.

 

[Boombox]

That moment when you enter him and you go over the hilt and it's almost like a pop, it's like heaven

 

[deleted1338543]

The first few times I was with a guy, I bottomed. And I'm apparently significantly tighter than most guys, or so I'm told. So one night I hooked up with a guy after a night at the bar. He's a 200 percent bottom, LOL. And, uh, loose. Slid right in. That's the point where I learned that usage matters.