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First time you had anal sex

Same. We were pretty young as well. Our research (i.e. friends' porn mags) helped us to know we needed some kind of lubrication. Vaseline was all we had access to and was plentiful, so that is was what we used. I actually liked Vaseline because it was slick enough to allow his dick to enter without hurting (too much), but viscous enough to allow me to feel the friction. And it kept his dick and my hole lubed for a very long time without the need to reapply.
Shelby29 said:
my buddy and me were pretty young too but we knew we needed some help and good old fashioned Vaseline was our lube of necessity He was hung better than me, too.
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sweet_taboo said:
Same. We were pretty young as well. Our research (i.e. friends' porn mags) helped us to know we needed some kind of lubrication. Vaseline was all we had access to and was plentiful, so that is was what we used. I actually liked Vaseline because it was slick enough to allow his dick to enter without hurting (too much), but viscous enough to allow me to feel the friction. And it kept his dick and my hole lubed for a very long time without the need to reapply.
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Since Vaseline was my first lube and used for many years that when I tried other thin lubes, no matter how slippery they claimed to be, I realized it was that VISCOSITY that was so great. You're right, stayed lubed without the need to reapply. And LOVED that friction too in my opinion unmatched with any other lube. The problem was Vaseline was not good with condoms or with some toys.. Great for bareback, though.
 
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He was nice and let me ride him so I could get used to his cock, but man I was so happy he came in 2 minutes because it still hurt!
 
Shelby29 said:
Since Vaseline was my first lube and used for many years that when I tried other thin lubes, no matter how slippery they claimed to be, I realized it was that VISCOSITY that was so great. You're right, stayed lubed without the need to reapply. And LOVED that friction too in my opinion unmatched with any other lube. The problem was Vaseline was not good with condoms or with some toys.. Great for bareback, though.
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Vaseline worked great when we first started out - the problem was it was messy as hell to clean up! And no way to explain it away!
 
It hurt the first time. His cock was way bigger than mine and I thought I was average and could "take me". I shoved household thing up my ass. Broom handle, mop handle, etc. Thought I could take it. It hurt like hell when he fucked me the first time. By the 3rd time I found I liked being hurt, and let guys fuck me all the time. I get off on knowing they are enjoying themselves.
 
Met him on grindr. I was a little nervous since it was my first time but i enjoyed it so much. He wanted me to ride him but my ass was tight so we did missionary instead. It felt amazing. After, he said that he couldn't believe this was my first anal experience cuz i took it like a pro and he could tell how much i enjoyed it. He told me to hit him up again when I wanted to get my ass pounded again but it never happened. Sometimes when im horny, i'll think about it and shoot massive loads.
 
ronboy said:
It was a while after I had first given Vincent his first sucking from me.

We were both young, and knew little about gay sex other than how to kiss, suck cock, and enjoy the feeling of touching each other.

I had read about straight anal sex in a Playgirl magazine I had nervously bought one time. I figured that if a guy and girl could do that, why not a guy and a guy?

Vincent was game to try it, so we did...

I gritted through the initial pain, and then enjoyed the feeling as he wrapped himself around me and pumped...(we were doing it doggy style)

He came inside me. I was jacking myself off and came on the bed.

Eventually, we figured out how to do is missionary style. And I loved looking up at his sexy face, and into his eyes as he and I were making love.
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This was written ten years ago.

But the memory of my first love, Vincent, will always be with me.

It hurt the first time...wish I had known then what I know now!

But our love was pure, somewhat naive, and new!

I grew to crave Vincent's cock inside of me. He was always clean, and ready for me.

He always gave as much as he took.

And when he left me for Heaven, It was a long time before I even wanted that intimacy with anyone again!
 
The one thing that I do wish is that I told the guy who fucked me first that it was my first time.

But even with only spit...I had no problem taking it.
 
Cumming quickly is a curse and a gift. Curse because as soon as his fucking starts to feel good, he's done. Gift because at that age the refractory time is virtually non-existent, so he can keep fucking you and cummimg for long periods of time.
hurl3y said:
He was nice and let me ride him so I could get used to his cock, but man I was so happy he came in 2 minutes because it still hurt!
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Same!
It's truly one of the best hurts to experience. From the very beginning I knew I liked it very forceful - the more aggressive the better. Lucky for me, I had a very close circle of neighborhood friends who were overflowing with testosterone, horny 24/7, and always very happy to oblige me. Lucky for them, I was always down to get fucked and they knew they could have it anytime.
MemphisShowOff said:
It hurt like hell when he fucked me the first time. By the 3rd time I found I liked being hurt, and let guys fuck me all the time. I get off on knowing they are enjoying themselves.
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I was in a steamy affair with my 45 year old married neighbour, id been sucking him off for a few months and i asked him if he wanted to fuck me, i remember it hurting so much but he showed no mercy and forced himself balls deep, i screamed and yelled in pain for about 5.minutes until the magic happened and there was no more pain only heavenly pleasure. I slept with him for 4 years before he moved away.
 
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An older man was also a significant part of my sexual awakening. He was the dad of one of my friends..and although he wasn't the first guy to fuck me, he was certainly the best at the time. According to my friends I had a very alluring quality about me and a hard yet soft body that made them just wanna touch me - a pretty boy. Apparently this man also felt the same way too. Sex just really seemed to kinda happen. He was gentle, but his sheer size, his urgency, his skill, and the relentless power of his stroke made sex with him so very different (and better) than the endless sex with the other boys. It hurt, but it felt so good. I wanted to have sex with him all the time, but of course that wasn't exactly possible. However, we did manage a couple times a week for years until I went away to college. Much later, he disclosed to me that he didn't intend for our rendezvous to become a thing, but he had become captivated by me and craved our intimacy.
MrAss said:
...and in a steamy affair with my 45 year old married neighbour, id been sucking him off for a few months and i asked him if he wanted to fuck me, i remember it hurting so much but he showed no mercy and forced himself balls deep, i screamed and yelled in pain for about 5.minutes until the magic happened and there was no more pain only heavenly pleasure. I slept with him for 4 years before he moved away.
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My first time, Yes it's painful and my heart beat is beating so fast. My partner used Sex toy first to loosen up my butt hole. :)
 
MrAss said:
I was 12 and in a steamy affair with my 45 year old married neighbour, id been sucking him off for a few months and i asked him if he wanted to fuck me, i remember it hurting so much but he showed no mercy and forced himself balls deep, i screamed and yelled in pain for about 5.minutes until the magic happened and there was no more pain only heavenly pleasure. I slept with him for 4 years before he moved away.
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Even if you have grown up without difficulty, and even if you were the one who proposed, this 45 yo guy should never have sex with you this young... This means he was not in his mind. Pedophilia is not fun : imagine you were a girl, could you consider this relation as something acceptable ?
 
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