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

0010661

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My first time fucking a man in the ass was with a guy who would blow me regularly. Nothing but a blow and go friendship for the most part. He was similar build and size to me but I would say was twink like. He was blowing me head on, his ass up and I reach over and grabbed it, pulled him into me and he moaned asking if I wanted to fuck him. I was nervous and very turned on and slowly slid my cock in, but he could take me as he’s bottom before. I began increasing my thrusts, my balls touching his and I came, continuing a bit after I came and felt it all over me. He turned around and licked me clean and I have never forgotten that time. I love fucking a woman, but sometimes a mans ass is great too
 

CaptainGrey

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My first time fucking a guy in the ass was also my first time with a guy and I really keep a good memory of it because it turned out to be really good and also quite funny.

We met on Grindr, he was a bit older and very experienced but he was very kind and respectful (which is quite rare on this app). It happened in his apartment, he was extremely tender and patient which made the sex so sensual. There was a lot of foreplay going on and when I finally penetrated him, it wasn’t to hard to get in since he already bottomed several times in the past but he still was very thigh inside. Loved the softness and warmth of his ass. We fucked for a while and probably could have lasted even longer if someone hadn't knocked on his door forcing us to get dressed.

I believe it was his accountant or whatever he had a meeting with. I didn't know what to say at that moment as it was obvious he was living alone and my presence was suspicious. But he immediately lied and said that I was his cousin, which made me burst laughing because we were absolutely not alike at all. I ended up leaving before it got even more awkward.

We saw each other again the next week and started hooking up quite often until he had a boyfriend and both decided to respectfully stop seeing each other. He is still to this day one of the best male hookup/sexfriend I ever honestly had. Loved how kind and very kinky he was at the same time !
 

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Still to this day I’m yet to enjoy penetrating a guy. I’ve got a thick dick, I find that most guys are so tight they squeeze the hard on away. Or the other side, guys that can easily handle it are... um... shall we say... loose? So it put me off. I don’t try penetration any more.

anyone else in a similar situation?
 

KevinOso

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Still to this day I’m yet to enjoy penetrating a guy. I’ve got a thick dick, I find that most guys are so tight they squeeze the hard on away. Or the other side, guys that can easily handle it are... um... shall we say... loose? So it put me off. I don’t try penetration any more.

anyone else in a similar situation?
Same here! I mostly bottom by choice but I love to top. Every guy I have been with can’t take my girth. It really sucks.
 

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My first time...fireworks went off in my head. I was 29 and he was a young college guy. We got a room, showered, fooled around and he wanted me to fuck him. Condom, lube and i entered him in one push. I yhink i lasted 5 mins. He squeezed his ass as i came. More fireworks went off in my head. They heard me cum in the next room thats for sure. First time with a guy and i discovered im loud when i cum in a guys ass.
 

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I can relate. Fucking a girl is ok. I’m married to one and enjoy it but with a guy things are amazing!! I do prefer to bottom today but I’ll take a guys ass anytime and be completely fulfilled.

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.
 
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I was 22. He was an older guy around 45, that I met months back at a bar. He had already gave me a couple of blow jobs on the beach . All I can say it was amazing ,very tight and he did a lot of moaning ,not like pussy the long you fuck the looser it gets, but pussy it’s fantastic also yes I am.We did it a few more times and I moved on. often wondered what It felt like to be a bottom
 

brandon38

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I was 22. He was an older guy around 45, that I met months back at a bar. He had already gave me a couple of blow jobs on the beach . All I can say it was amazing ,very tight and he did a lot of moaning ,not like pussy the long you fuck the looser it gets, but pussy it’s fantastic also yes I am.We did it a few more times and I moved on. often wondered what It felt like to be a bottom
Sound hot and fun sir .
 
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fuckyeah

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A man's ass is very different from a pussy. It's smooth and tight and stays tight for the most time as you fuck it. There are no bumps or crevices as in a pussy, so you won't get the same feeling, but the tightness tends to make up for it. For me, however, knowing I'm fucking a man's ass is enough to send me over the edge. Looking down and seeing is ballsack when I'm fucking doggy style sends my milk shooting straight up his ass.
 

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Same here! I mostly bottom by choice but I love to top. Every guy I have been with can’t take my girth. It really sucks.
I have a 2" dia x 9" silicone dildo that I can take. But it takes to so long to get to the full stroking mode... Most guys by then I'm sure lose the stimulation waiting. Maybe work him with a toy first?
 
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manunlisted

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Unfortunately my first time was not that great! I was cruising for oral and this guy begged me to top him. I wanted to and he turned around and bent over. He had lubed up and I entered him easily. That was the problem- he was so loose that I barely felt anything. I couldn’t cum. It was disappointing and I’ve never tried since.
 

bi2

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Physically - much the same as a girl’s ass.

Mentally - pretty powerful in a strange way, there’s something dominant about it (‘it’s me penetrating you, not the other way around’)
Good comment.

I have had male partners that have shared the same thoughts as you, they enjoyed overpowering and taking me from me behind. Mentally they told me it makes them feel very masculine and strong. I actually enjoy the power play and the role I take as a totally submissive bottom, so its been mutually enjoyable for both of us.

The power dynamic is interesting as before (foreplay) and during sex, my partner will be very much in control and dominant. Post sex, we are very much equals. If anything, my partner is very sweet and caring in case he crossed a line with me by being too aggresive or rough with me during sex.
 

midwesthubbi72

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The first time was great. It felt heavenly and natural. We fucked on a lounger next to his pool. Prior to me fucking me out at the pool, he took me up in the shower and the master bed. We spent the weekend breeding each other.
 

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It was a guy I’d sucked off at my gloryhole for a while. He’s married but really liked a close male bond. He asked if I’d fuck him. I still remember the way I mounted him. He was warm, moist and tight.
since I’m uncut and 7 1/2 inches and over
5 around it felt great. As I rode his ass I slapped it a few times and continued to ride him until I busted . Shooting all over his ass.
 

brandon38

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It was a guy I’d sucked off at my gloryhole for a while. He’s married but really liked a close male bond. He asked if I’d fuck him. I still remember the way I mounted him. He was warm, moist and tight.
since I’m uncut and 7 1/2 inches and over
5 around it felt great. As I rode his ass I slapped it a few times and continued to ride him until I busted . Shooting all over his ass.
That hot