Entered By Cock For The First Time - How Was It?

[Chowderbomb]

Describe your 1st bottom experience (real cock), the leadup and maybe subsequent ones.

 

[Jamsion]

I was a teenage boy when I received anal for the first time. In my opinion the first time was the best. I took my friends cock inside of me-anal sex. The sensation of it was unbelievable. I cannot describe the eroticism of how it all felt. We were new to the experience and we really didn't know what we were doing. It is hard to believe that those times were the most sensational. Sharing this experience may not be as descriptive as you would like. But sometimes it is best to keep things toned down to a certain degree.

 

[Beanie]

For me the first time was quite indescribable. It was like I was missing something until then. Have you ever gone too deep underwater and lost your breath and raced to the surface to get some air? That first breath is what it felt like. Like a massive relief, a wave of pleasure, a warm embrace.

 

[Chowderbomb]

For me the first time was quite indescribable. It was like I was missing something until then. Have you ever gone too deep underwater and lost your breath and raced to the surface to get some air? That first breath is what it felt like. Like a massive relief, a wave of pleasure, a warm embrace.

That is quite a description. I'm glad it was so satisfying for you

 

[Onetimeuser4]

For me it was a bit painful and bloody but I dont think I would have chosen any other way lol I had just turned 19 and was finally exploring sexuality in college.. I was a pretty shy guy in high school so no action there. I met this guy though craigslist and was ready to have my cherry popped. So I met him and did oral, which was also my first time. Unfortually I was unable to go through it due to the sheer anxiety I was getting. Ended up texting him though, we ended up hanging out and actually going out but only went as far as BJs and jacking off. Couple months later maybe like 3 or 4 of going out be asked me to be exclusive as to be his BF. I really liked the guy and was absolutely amazed he did not rush me so we got together. Less than a week later he ended up taking me to the beach for a date and we went up a lonely road with no cars and made out. He then proceeded to undress me in the back of the car and pull my pants off in a very romantic and delicate way. He told me that he was going to go in slowly while he lubed up his cock and if I needed him to stop to squeeze him lol he started by kissing me while rubbing some lubed on my ass and then I could feel the tip of his cock rubbing against my ass. Then proceeded to go in very slowly. As it was my first time, I was used to fingering myself but had not experienced anything bigger than like 2 fingers. I moaned In pain while clutching onto his ass. He slowly pulled out and began to kiss me down my neck, to my nipples, down my stomach and began to suck on my dick. The pleasure helped me quickly forget about the pain. The grabbed the lube again and said he was going to try again. So proceeded in the same way. This time after I got through the first Mr. LPSG penetration pain, I was able to withstand the sensation better. It still hurt while he slid his cock deeper and deeper. Me holding onto his ass but telling him to keep going. My cock dripping of precum as he slowly thrusted his cock in my tight ass. I could see his face full of pleasure as was mine. I had never experienced anything like it, pain and pleasure mixed to create a euphoric sensation. He continued and fucked me a little faster while I tried to keep myself from cuming. He told me to cum as he was getting close and feared it would hurt me and make me lose my hard. I came as I had never before, full forse sending my cum all the way to my face. He kissed me, grabbed me tight and began to pound me. He was right, it did hurt and quickly lost my hard. I moaned in pain for a bit as he was going at it. Perhaps maybe less than a minute he thusted in one last time deeper than any other time and saw his face full of pleasure. The pull out was almost as painful as the first penetration. Grabbed an old tshirt that was in the back to wipe us and noticed some blood on it. He told me that the wait was so worth it and told me he loved me. We just sat in the back of the car for a little while trying to catch my breath. Lasted with the guy for 6 years until fate just tore us appart. Good memories though.

 

[indyfrat79]

I'd had several oral experiences before and during college and, while in college, had a few opportunities to top. I wasn't out so all play was on the DL. After graduating college, I moved to a midsize city and discovered gay.com. This was the best way to meet people back in the mid 2000s. Fairly quickly I developed a handful of regular chat buddies and soon made plans to meet a guy. I was 24 and he was late 30s. He was very closeted and really masculine - a guy's guy. He was about my height - 5'10" - but well-built, short cropped hair, and a nice hairy chest with a 7" cock. Like me, he was a top but we enjoyed drinking beers together, watching movies, the evening would usually end up in swapping head or jerking off together. Our relationship evolved over the course of several months and we'd chat almost daily - he was like a big brother/confidant/and sexual mentor all in one. We'd chat about other hooks up we might have, dates we went on, etc but would still hang out once a week in person.

He always gave me a hard time about being a top when he knew that I'd never before bottomed. One Friday night I hung out at his place, we had a few drinks, and he told me that I could crash if I wanted. This was a big step and the first time we'd ever discussed spending the night. We had a few more drinks and around midnight we went to bed. We started fooling around and I said to him "Tim - can I bottom for you for the first time?". Being a smartass, he started laughing and said "I thought you'd never ask". It was the most perfect experience imaginable. He was gentle and told me step by step what he was going to do - kissing, sucking, fingering to loosen me up. It was an incredible experience. We'd both just gotten HIV tests so I told him I wanted to feel him without a condom. It hurt a little but was also such a good, foreign feeling. He told me he was getting close and I clutched him in my legs and told him that I wanted it inside me. Hearing him orgasm and feeling his load inside me caused me to shoot a huge load that hit me in the eye - his orgasm caused mine (no hands!). We cleaned up and I spent the night in his arms.

Despite being a country boy from Northern Indiana, he was a total gentleman and made me breakfast the next morning and asked me how I felt about it. I let him know that I was still a top but that it was an incredible experience. That was the only he ever fucked me and our relationship never changed. He continued to be my "big brother" with benefits and I was heartbroken about 18 months later when he told me he was in a relationship and we could no longer play. Nonetheless, I'll never forget this awesome experience.