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First Time Anal

Fellowship

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A weird mix of both pain and pleasure for me. My first time was totally unplanned (on my part), but I think the guy I was with had intended on talking me into it because he came fully prepared. He wasn't forceful, but not all that patient either. I remember him saying, "I'm not taking it out. You just gotta get used to it." He gave me only like 30 seconds to get adjusted to him before he started stroking. He hit my prostate several times which I didn't like AT ALL, but still I managed to stay hard throughout the entire thing and I even came twice! When he pulled out, I was relieved but also felt so empty inside.
 

towhead5

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A weird mix of both pain and pleasure for me. My first time was totally unplanned (on my part), but I think the guy I was with had intended on talking me into it because he came fully prepared. He wasn't forceful, but not all that patient either. I remember him saying, "I'm not taking it out. You just gotta get used to it." He gave me only like 30 seconds to get adjusted to him before he started stroking. He hit my prostate several times which I didn't like AT ALL, but still I managed to stay hard throughout the entire thing and I even came twice! When he pulled out, I was relieved but also felt so empty inside.
How long before you liked it
 

Adventure86

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Was your first time planned
It was planned, I had been flirting with the oldest son of my next door neighbor. My mom was out of the country and I was left in charge with my cousin, my cousin went on a date with his girlfriend and the guy who I was flirting came over. We were watching a movie, one thing led to another and holy shit it was amazing
 

curtdude

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it was great not having done it before I was nervous. he put his head on my hole and gently pushed in I relaxed and it popped inside me there was pain he was still until my ass got used to him he inched in slowly until his balls were on my ass he started
pumping g and it felt fantastic feeeling his Co ck filling me up he ejaculated in me and collapsed on me sweat all over he got soft and slipped out of me all day long thoughts of his cum inside my ass I had a part of him in me
 

Luvcutdick

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I love anal ..........................

However, the first time was rough. My partner was hung like a horse; long, thick and had a mushroom head. It just didn't work for me.

I prefer "right sized" cut cocks over large cocks.

There is only one "first time". It is best to fully understand anal because done right, WOW !.
 

WilliamG

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painful, he wasn't huge, around 7 - I'd played with a dildo my size (8) so I thought I was ready. Took me a few times before I got the hang of it. I love fucking pussy, with guys I prefer bottom, unless i find a smooth twink ass :)

Hit the nail on the head with trying out dildos first! I'm always shocked when I read about guys getting fucked for the first time... And having never tried some toys first! I've not had a guy in me yet... But I have a LOT of toy experience!
 

Fellowship

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How long before you liked it
I've bottomed less than 10 times; I much prefer to top.

Each time has more or less been the same experience as the first, a mix of pain and pleasure, which I chalk up to not bottoming (or using toys, engaging in anal play, etc.) consistently. So I can't say that I've ever come to like it in the sense that I would convert to being solely or even 50% a bottom. I only do it for guys that are 1) Bigger than me (both body & cock size), and more masculine than me. I'm a fitness buff and present masculine, so they have to be more "alpha" than me.

I will shamefully admit that several times were with random hookups and without protection. But there is indeed some weird/euphoric feeling as @curtdude pointed out about letting a guy cum inside you, sweat and collapse on top of you, and then pull out with his cum still inside you. He has marked you with his DNA, literally leaving a part of himself inside you. For me, that experience is the "pinnacle" of sex.

I experienced it really only once in 2018, but as you can tell it has left a very strong impression on me. It was with the second guy I bottomed for, a fit, masculine 25 year old Black guy, 8 inches, and sex with him was so good that it made me realize why girls get crazy/obsessive over guys or put up with their BS. I would become a full time bottom if he were my partner. I was only planning on giving him a blowjob but he kept taking off my clothes and positioning me for sex. Once he pushed inside of me (in missionary) and stroked a few times, he smirked and sarcastically said, "And you're a top, right?" :rolleyes: His strokes were very gentle, more along the lines of making love than simply pounding for the sake of pounding.
 

4D2020

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My first experience was rather unpleasant.

Had someone with pearl beading/piercing/implants (or you could imagine it like a bumpy cucumber lol) penetrated me.

It was my encounter with a stranger at gay Sauna for the 1st time.

Neither did he let me adjusting to his dick in me, nor did he slow down in thrusting into me. I was trembling due to the pain while cumming and peeing afterwards, unable to control my lower body. Maybe there was pleasure in it, but all I felt during the session was pain.

Fortunately no bleeding, but then I never want to be penetrated again after that.
 

towhead5

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My first experience was rather unpleasant.

Had someone with pearl beading/piercing/implants (or you could imagine it like a bumpy cucumber lol) penetrated me.

It was my encounter with a stranger at gay Sauna for the 1st time.

Neither did he let me adjusting to his dick in me, nor did he slow down in thrusting into me. I was trembling due to the pain while cumming and peeing afterwards, unable to control my lower body. Maybe there was pleasure in it, but all I felt during the session was pain.

Fortunately no bleeding, but then I never want to be penetrated again after that.
Did you ever bottom after that
 

HornyBlower

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My first experience was rather unpleasant.

Had someone with pearl beading/piercing/implants (or you could imagine it like a bumpy cucumber lol) penetrated me.

It was my encounter with a stranger at gay Sauna for the 1st time.

Neither did he let me adjusting to his dick in me, nor did he slow down in thrusting into me. I was trembling due to the pain while cumming and peeing afterwards, unable to control my lower body. Maybe there was pleasure in it, but all I felt during the session was pain.

Fortunately no bleeding, but then I never want to be penetrated again after that.

sorry. this sounds like a horrible experience.
 
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goldscorpguy

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What I remember most about my first anal was that I had no doubts at the time whatsoever. I've described the scene on other threads but I've never mentioned my state of mind. I was with a guy who knew he was my first. He had built me up to it so slowly and patiently. There was one moment where I felt the head of his cock brush across my hole and that was when I knew it was time. I could feel myself rhythmically contracting, like uncontrolled kegels. He brushed across me and then around me several times more, and each time it felt like I was physically opening for him. I had only ever used toys on myself but had never experienced anything like this. By the time he pushed inside me I was yearning for it. Yes, there was a little pain at first, but still no doubt, and the pain soon gave way to a feeling of deep connection and trust. That first time was over twelve years ago now, still no regrets, and many more experiences.
 
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My first time being fucked in ass was while I was tied up and gal started to play with hole than she did it slipped that vibrator in at first I didn like it and again I was tied up. After that she ate my asshole for a good 10 minutes I rather enjoyed that. Lol
 
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lrnbnt94

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My first time getting anal felt very natural for me. He did have a nice bigger than average cock, which was also very delicious. He was very gentle and I felt more pleasure than pain.

I guess my ass was very hungry for a cock.

We did try a few positions. My favorite was riding him, because I could control the pace, we looked at each other when doing it while holding hands.

He also asked to move a bit so we coukd see ourselves in the mirror, which was a very nice touch. Needless to say a lot of cum came out from both of us.

My first time actually set a very high bar for sex with men.
 

ilovetowatchcs

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For my first time, I made sure they guy did not have a thick cock. He was about 7" hard, circumcised, with a nice mushroom head. But for your first time, the guy has to go slow. Has to be patent. Have him put it in 1-2", then slowly pull out. And keep doing this until at least half his cock is in you. Because your ass will accomodate him - but slowly. Your real reward will be when he is all the way inside you and says he's cumimg - and you feel his cock pulsating.