First anal

erpap

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It hurt but I loved it! Wasn’t planned was wrestling around and his cock hit me right smack on the hole, saw stars, he begged me to let him fuck me after I calmed down and I agreed! Been hooked ever since and getting fucked.
 

muskokan

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it was beautiful! he took his time and over the course of a weekend had me stretched out enough and begging for his cock to enter me. That was over 30 yrs ago and am still loving that feeling when a good top uses my hole like he owns it!
 

niagarachatter

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It was on my 18th birthday, I went for a trip to Toronto and was searching for a exotic massage. I came across a guy claiming he was a gay 18 year old Chinese masseuse so I went to his place as it was just up the road from where I was. He had me lay naked on my back while he got undressed. He gave a good rub to my upper body and then to my legs and feet and then asked me to turn over while it was difficult laying on my hard cock I did and then he reached under and pulled it between my legs. While rubbing my back and legs he kept hitting my cock making it stay hard. He put some more oil on my ass and started fingering it. I guess he could tell I was enjoying his fingers in me by the moaning I was making then he started sliding his naked body on mine and next thing I knew his cock was inside my ass and he fucked me real good. After he finished fucking me he got me to flip back over and he sucked the cum out of my dick which only took a few seconds once it was in his warm mouth. I have been hooked on getting fucked ever since.
 

worshipbig1s

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In high school my regular "suck buddy", (I would always suck him off almost daily!) - loved his curved up cock. Once when I was getting ready for work, he joined me in the shower, totally unplanned. He was behind me and started lathering up my back and ass and his cock and he just pushed it in - it hurt like hell and I had him get out of the shower! I wish we could try it now!!!!

The actual first complete experience wasn't until I was 24, fortunately I had a few drinks but the guys was rough and it felt like I was getting stabbed - I don't know how I turned into the hungry bottom I am today with those two experiences - but now I can't get enough!
 

cedarizzo

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My first time was with one of the twin boys that lived behind my grandparent's house. I was all alone at my grandparent's house so he came over. One thing led to another and we were busy doing our usual play. We were playing with each other and sucking each other. He asked me if I had ever been fucked. I hadn't even thought about it and told him I don't know. It really didn't sound appealing to me at the time. He started sucking my dick and would get a finger wet and start rubbing it on my hole. It felt good and I let him continue. He kept getting more spit on his fingers and would rub it on my hole. He never put a finger inside my hole, but I was pretty naive and didn't know better. He turned me around and bent me over. Next thing I know, he tried to jab his dick into my hole with no lube. His dick wasn't very big, maybe 5" long and pretty skinny, but DAMN, that hurt like a mother fucker!!! I jumped forward to get away from him and told him that he wasn't going to try to fuck me again. I was in horrible pain and told him that he needed to leave. He got mad because he still hadn't gotten off, but I told him that wasn't going to happen.

I didn't try anal sex for MANY years after that. The next guy was my first boyfriend. He asked if I was a top or bottom, and I had to tell him the story about my first time. His dick was MUCH bigger than the guy from the first time and I wasn't sure if I really wanted to bottom. He told me he would take it slow. He worked my ass for a long time with lots of lube and spit. He started to push his dick in and it was pure heaven! I'm glad I tried it again, it was so worth it!
 

hvdude

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It honestly wasn't all that it was cracked up to be. It was a friend and we had a condom (not that we needed it, it was pre-HIV). He slipped it on and slid his dick in. Three pumps and he came. One and done.
 
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RowanB

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Was okay . Was with a guy I'd been hooking up with for a while. I always fucked him and we sucked eachother, but I'd never bottomed before (or had any backdoor action at all, not even a finger brushing over it...)

Anyway, he wanted to "introduce me to something new" one night and I reluctantly agreed (probably just because I was super horny), so he turned me over and started eating my ass. It was fucking spectacular! He must've been back there for a good 30mins while I just lay there gasping and moaning and loving every second.

Because that was so amazing , and he wasn't very big, I thought I'd give dick a try.
It didn't hurt (probably relaxed from the rimming) but it felt pretty damn weird having something up there. Not unpleasant but not super great either.

It was only after I started dating a vers guy and we started taking turns on eachother that I came to appreciate the wonderful joys of getting pounded.
 

Unk Papi

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Mine was lame, I had turned 18 and felt like i needed to ditch my fake love for pussy and be a full grown "i love myself" homo. I went on a hooking site and met someone by my home, He was cute and his dick looked appealing. He fucked me and i realized i liked to top.