First Anal

cedarizzo

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First time for me was horrible. But both me and the top had no clue what we were doing. He tried to jab it into me with nothing but a little spit as lube. This does NOT work and I don't recommend it for anybody. If you find an experienced top, one that uses lots of lube and time to work on your hole before he tries to put his dick inside you, it will probably still hurt, but the pain will be much more tolerable and once the pain subsides, the ecstasy will be incredible. The pain goes away as long as the top knows what he is doing.
 

jslates215

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I lucked out. My ex was very experienced in roping and took it slow. It was amazing, at times, but painful at others.
 
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muskokan

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it was fantastic but also after 2 days of foreplay and much teaching from a very gentle and caring older man. He showed me how to please, be pleased and how to open up like a flower, to this day i still think of how he trained me to be the bottom boi i am. I do thank him and would love to be able to play with him again.
 

JonFranklin

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It was AMAZING! I was very fortunate to find a guy that knew what the hell he was doing (because I sure didn't). I don't remember any pain, just remember feeling like I didn't want it to end
 

deine_huendin

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it was fantastic but also after 2 days of foreplay and much teaching from a very gentle and caring older man. He showed me how to please, be pleased and how to open up like a flower, to this day i still think of how he trained me to be the bottom boi i am. I do thank him and would love to be able to play with him again.
"open up like a flower".. sounds so great !!!
 
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MuscledHorse

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My first time taking cock was amazing. My buddy had me top him first, so I knew what to expect. I was hungry and nervous at the same time and the sensation of feeling his hard cock sliding into me was surprisingly pleasurable. I came so hard from him fuking me, I turned into an instant pig and wanted it some more.
 

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My Frist time being a bottom was unforgetable.
What started off as a date ended up going back to his for a night cap and one thing lead to another, we end up but naked in bed ok we had a few beers but oh my god the sex was great I came hands free while he was in me and then he didn't stop till he came. After we finished we both fell on the bed and I fell asleep with him in me.
Only to be woken up early hours of the morning with him fucking me slowly
 

Marcbow

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My first time was scary but a experience that I never forgot..
The feel of the first time he enters you painful to start but after a few seconds it felt great the sensation of him trusting his cock inside me his body pressed against mine his breath against my neck the sound of my buttocks slapping against him the warmth of his cock inside you if he cums inside you the feeling of him cumming is a experience in its own right sounds silly but somehow I felt at that point we became as one.

that was my first experience
 

HungBtmVegas

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THANKFULLY it was with a guy much older and more experienced than me, so he knew how to be patient, ESPECIALLY bc he has a really thick cock, so it was painful, but not TERRIBLE and I was taking him balls deep by the 3rd time
 

geekcub

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there was a big age gap for my first time. he took time to get me warmed up and i was dying for it. It hurt alot but was totally amazing at the same time. he was quite big and thick and liked to fuck hard. So gave me a rough raw initiation to getting fucked, but thats how I love it now!
 

Luis33172

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Tongue play right on my hole and BOOM there go the legs. It also helped I took an ecstasy that just brought any walls I had up.

I have trust issues. If something isn’t right, the hole seats itself tighter than the pressure that makes coal into diamonds. NOTHING not even a microfiber thread. Dick limps. It’s like “danger Will Robinson!” Or Whoopii in Ghost “u in danger girl”. HEY sounds crazy, but I’ve weeded out some bad guys who sounded good and cute as fuck. The vibe body language was NOT! If It’s inside, colon contracts and starts pushing it out like a bouncer. It.does help sticking a toy a few days before and leaving it in. Relaxes me the day of. Just to be extra sure ..I’ll stick one in on the way there that way ur pre-lubed LOL
 

Brodie888

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I had anal play as part of my masturbation routine from a young age. I was playing with my hole long before I even admitted to myself I was gay.

So the first time I had sex with a man was easy. My only regret was that I did it with someone I didn't know. Being the first time it would have been reassuring to have been able to talk to him later if I wanted to.

He wasn't very good, he had as much personality as my dildoes. I came because I made myself cum really.
 

Andrue

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My first time taking a dick was amazing. But it wasn't my first time putting things up my butt so that helped me a fair bit. I had made a dildo out of clay, essentially a copy of my own dick size-wise, and varnished it. That, along with some household items, was what went up into me first. And fingers of course.

The first actual real dick I had in me was at a college classmate's place, let's call him "G". It was on New Year's Eve, 1973>74 and G's mom was out babysitting the grandkids until the morning so we had the house to ourselves.

After a bit of booze, we retired to the bedroom and the games started. He was experienced and I was not, at least not with another person. G knew it was my first and he was willing to instruct a well as being conscious of taking it slow and easy.

We did everything in your basic vanilla gay sex repertoire. Sucking, fucking, jacking each other, lots of kissing and fondling. It was pretty damn sweet.

As for the fucking itself, he fucked me first. Fortunately, he was not big so taking him was not an issue. He was basically very average in both length and girth. There was lotion in use here - this was before lube would be easily available anywhere. But things went in rather smoothly. G fucked me for a while and, eventually, I fucked him too so I got to play both ends. We held off cumming until much later in the session.

I'd rate that, for my first time, as pretty much 100% success. G was aware, didn't rush anything, was careful not to go too far and too fast. He wasn't selfish, inconsiderate or other qualities that might make the first time a regrettable thing. Plus he wasn't huge so it all went really well.

Helped to set me up as the happy bottom / versa-bottom that I am today.