Your reaction to first-time anal

heirtothewind

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With few exceptions, the penetration of anal sex for the first [few] times hurts. Did you stop because of the pain, bite the pillow, scream or cry, or just put up a macho front and took it. I myself screamed but remained determined to take it to reciprocate out courtesy for the great blowjob he gave me. But it still hurts and I still get off to screaming.
 

Infernal

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No screaming, but it was fairly uncomfortable and took forever to actually get it in. When he finally got it in he finished pretty quick. It was a lot of buildup for not much in the way of pleasure. I turned the tables on him and pounded him into the mattress, so I guess it worked out for both of us.
 

theplayerking

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We were teenagers. He was straight and had never done anal or been with a guy before. I'd never even kissed someone before. We didn't know what we were doing. All I knew was that I wanted a cock up my ass; he was bored, horny and curious. It was awkward and a little painful (fortunately he had a small cock) but I just bit my lip and took it like a champ.
 
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In the end I really enjoyed my first anal, though it was a little painful in the beginning. There were several reasons: the guy was gentle, relaxed and took his time, we used plenty of lube and, not unimportant, his cock wasn't too big; it must have been 7x5 or something.
 
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alexiscd

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Nervous scared and excited all together,, I put it off so long I chose a man i had been seeing and giving oral too for 6 months i gave in to him one night he gave me plenty of foreplay fingering and lubing me using plugs and toys until he got me in position I felt him touch me with his cock he gently pushed it in opening and stretching me going deep it did hurt but i was also getting pleasure i had longed for he was gentle but very thorough,, he did not use a condom and filled me for my first time also it was amazing and i knew i was complete that night
 

Mister2101

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Nervous scared and excited all together,, I put it off so long I chose a man i had been seeing and giving oral too for 6 months i gave in to him one night he gave me plenty of foreplay fingering and lubing me using plugs and toys until he got me in position I felt him touch me with his cock he gently pushed it in opening and stretching me going deep it did hurt but i was also getting pleasure i had longed for he was gentle but very thorough,, he did not use a condom and filled me for my first time also it was amazing and i knew i was complete that night
Very hot Alexis. Thanks for sharing.....
 
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Samantha Hopkins

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My first time was not horrible or overwhelmingly painful. I didn't really want to do it, but I wanted to make my friend happy. We did it at his parents house, in the basement playroom. He lubed me up with a ton of vaseline. I leaned over an ottoman and watched TV as he slowly pressed himself inside of me.

Any time he felt me tensing up, he would stop. He would not remove himself from me but he stopped pushing in. Once the head of his cock was in me he held still for a long time. He coached me and encouraged me. Time seemed to vanish and the next thing i realize feeling was his pubic hair on my ass. At that point I knew he was all the way inside me.

Knowing his cock was all the way inside me made me feel really uncomfortable. Not because it hurt but because I didn't want to be gay. Finally he slowly started pumping, and just sort of hung on until he finished.

We did that almost every day after school after that.
 
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My first time was not horrible or overwhelmingly painful. I didn't really want to do it, but I wanted to make my friend happy. We did it at his parents house, in the basement playroom. He lubed me up with a ton of vaseline. I leaned over an ottoman and watched TV as he slowly pressed himself inside of me.

Any time he felt me tensing up, he would stop. He would not remove himself from me but he stopped pushing in. Once the head of his cock was in me he held still for a long time. He coached me and encouraged me. Time seemed to vanish and the next thing i realize feeling was his pubic hair on my ass. At that point I knew he was all the way inside me.

Knowing his cock was all the way inside me made me feel really uncomfortable. Not because it hurt but because I didn't want to be gay. Finally he slowly started pumping, and just sort of hung on until he finished.

We did that almost every day after school after that.
I love the image of the ottoman and watching tv while he entered you :) My first time was horrible, hurt like hell, gave me no pleasure at all, not one volt of desire - and I decided then that if I was going to carry on having sex with men, I'd have to be the top.
 

CraigS41

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My first time taking dick was Amazing and Beautiful. He was an older man, about 59 or so. I was 31 (Late Bloomer) His dick was about 7.5 x 5.5 cut, BIG low hanging balls. He lubed up his dick and my ass really good and put the head of his dick against my virgin hole and gave a gentle pressure and held it there while kissing me and coaching me to relax and breath. Very slowly and with a constant and gentle pressure on my tight hole, his dick SLOWLY slid inside me. The second I felt his balls touch my ass, I shot a HUGE load of cum between out bodies. He smiles and giggles and started to pull out. I grabbed his waist and pulled him back inside me. His eyes lit up and he resumed his kissing and slow fucking. I really have no idea how long he lasted. I do know that I shot another 3 loads before he finally filled me with his cum. We laid there (With his dick still buried BALLS DEEP inside me for a LONG time before his dick slipped out naturally. I was HOOKED from that night on. I came back to him for 2 months, every 2nd or 3rd night for more of his AMAZING fucking.

Unfortunately, his job was moved across the country and we lost track, but I will NEVER forget what he gave me, the appreciation of dick ;P

Craig
 

Jonlovesjizz

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My first time was exciting, I remember his putting loads of lube on my ass, he fingered my hole for a short time, he was slow in inserting, I got an instant erection, I remember saying to him that I needed to piss, it didn't take him long to erupt in my ass, I came also, it felt so intense, he stayed in me until he went soft.