First Time Anal

bijockfl

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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!
@WilliamG can I be your first
 

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
 

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.
 

bijockfl

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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.
Hot @ilovetowatchcs like to experience your tight hole
 
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