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

Tight_End_SC

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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.

It's good to be tight. Part of staying that way is not to let everybody get it. ;)
 

brandon38

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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.
Sound amazing .
 
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deine_huendin

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It's good to be tight. Part of staying that way is not to let everybody get it. ;)
so right ! stay tight ;-) !
for HIS but also for your pleasure
i always avoided big dildos, or more than two fingers...
so it stings and hurts almost like at the beginning;-)
but i enjoy it to enclose and wrap his dick warm and tihgt
 

DiamondJoe

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I was 17/18 and friends of mine, a MF couple, came to stay at my parents' house. On grounds of propriety he was billeted in my room with her in the guest room.

So, fast forward to the night time, me and the bf were in my room watching some film and I still to this day can't remember quite how it started but soon enough he was sucking my dick and I eventually fucked him on my bedroom floor. I remember biting the back of his neck as I came strongly inside him.

Yeah, bit of an eye-opener and most satisfying.
 

erpap

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so right ! stay tight ;-) !
for HIS but also for your pleasure
i always avoided big dildos, or more than two fingers...
so it stings and hurts almost like at the beginning;-)
but i enjoy it to enclose and wrap his dick warm and tihgt

Love hearing these tops stories! As much as I talk about being a bottom and getting a good fuck on this site I don’t get fucked that often. I like being tight. Still wondering what a super thick cock would feel like. Maybe not so tight afterwards?
 
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kutag

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My first time was after I had been to a gay sauna a few times, only played and had my cock played with before.
It was a side room very dark and a few men in there, on my left was a guy fucking another doggie I bent down for a good look seeing his cock up this guys arse. Very much a turn on and I pulled my cock, it was hard, to my right a bloke was bent over and was waiting for a cock. Put a condom on and entered his arse and pumped him, don't know why, it could of been thinking about cheating on my wife as this was the first time my cock had been in anyone else, anyway after a very short time I went soft. I did blow a load later in the porn tv room where a guy milked my cock by hand not arse. I did better in later visits to gay saunas.
 

WebMale80

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I didn’t love fucking guys asses as much as I like fucking pussy but nothing makes me orgasm harder than getting fucked.
I like to keep it complicated LOL
 

bigunzippedstudent9

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Just did for the first time last week (in my late 30s for ref). Hes a hot gay younger guys whos been stroking and sucking me on and off for about 3 years. Lots of back and forth emails about me topping him but we never went there, until this time. I sat down on a chair, put on a condom, lube amd then he just sat on it. Slowly at first, then a pop when it went it. He took about 3/4 of me and was saying how good and huge i felt... well i basically blew in like 1min total.
 

Philly swords

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Just did for the first time last week (in my late 30s for ref). Hes a hot gay younger guys whos been stroking and sucking me on and off for about 3 years. Lots of back and forth emails about me topping him but we never went there, until this time. I sat down on a chair, put on a condom, lube amd then he just sat on it. Slowly at first, then a pop when it went it. He took about 3/4 of me and was saying how good and huge i felt... well i basically blew in like 1min total.
God damn that sounds good
 

bigunzippedstudent9

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God damn that sounds good
It was crazy hot. It happened it the backroom of his retail store on my lunch break haha. Total porno setup. Still digesting that it happened. Hey keeps messaging me that it wants to take it all soon. I'm sure we'll try it again, I really want to go balls deep next time.
 

fuckyeah

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It was crazy hot. It happened it the backroom of his retail store on my lunch break haha. Total porno setup. Still digesting that it happened. Hey keeps messaging me that it wants to take it all soon. I'm sure we'll try it again, I really want to go balls deep next time.
Go get ‘em man! Fuck his ass deep! Make him moan! Enjoy!!!
 

Stephenmass

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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.
He obviously didn't know how to clean properly. That should not have happened!
 
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thongboy

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He was an older guy, and an experienced bottom. He knew that I'd started fucking a girlfriend in the ass, but he said he could still give me some tips. He wanted me well lubed and to work my cock gently past his sphincter and to enjoy the tightness. Once I was getting in, he'd tighten his grip and told me again to enjoy the way he was working my cock. He also warned that if you're topping you must always listen to your partner and slow down or withdraw if asked. He said this is really important with a big cock that is going balls deep.
He said the other important thing was to angle my cock so it was effectively hitting his prostate. He said a lot of tops forget about this, but it's really important for a bottom. He said he would be feeling pleasure at being "filled" and having his prostate stimulated. He said I should enjoy the feeling of being gripped and having my entire cock worked over.
It felt different from being in my gf's pussy or her ass, and that was partly because of his prostate and also because he was a power bottom who knew how to work a top. A few weeks later when I started fucking a buddy who wasn't experienced, it didn't feel the same until he became more comfortable and we started getting in synch.
This first time with an older dude I was so excited by the stimulation that I came sooner than I wanted — and I normally can last as long as I want. But he said not to worry, we'd fuck again in half an hour and he told me to try to relax. The second time it was an awesome extended fuck.
A lot of guys expect the earth to move the first time. But anal fucking needs time and patience. I guess I was lucky to have a good teacher.
 

bi2

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The first time it happened, I was totally shocked and speechless.

It happened with an older and larger neighbour that gave me massages ongoing. He had oiled me up and in particular my arse, really good and proper while I was laying on my stomach.

I have had several massages with him beforehand and trusted and enjoyed everything we did previously. So going down this path felt a natural progression of our relationship.

When he asked me to flip over, on this particular occasion he strongly lifted me up and turned my arse towards him with my legs hanging over his shoulders. I smiled and quietly asked him, "What are you doing?", he smiled back and kept quiet then proceeded to enter his dick slowly and carefully into my hole, telling me to relax and breathe.

After he entered and slowly thrusted away, I felt so hot, desired and sexy, I couldnt stop groaning, while he was grunting away with each thrust.

I have said it before on here, I was lucky that my experience was with a very kind man.