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Taking It Deeper Than Deep

Posted by a straight man:

May 26, 2026

By bifi4u

I have been playing with guys for about 20 years. I never dreamed that guys could be so good and I was totally turned off by the prospect of having sex with a man, until I had it.
Early in the bi days I had an adventure. I had many oral encounters with guys but relatively few anal. I had been fucked maybe twice. I was feeling the need for a guy to suck me so I put an ad on Double List. I got a reply from a guy several miles away and ended up inviting him over. He was a bit older than me, about 6 ft and kind of thin build.
We decided to get naked and suck each other off.
When he took off his pants I immediately saw a nice 7 to 8 inch cock that was just average girth, nicely shaped and closely trimmed with shaved balls. But what was most noticeable was how his lower abdomen protruded at the pelvis behind his cock and pushed his cock and balls way out front. I had enough experience to know that most of the chubby guys I had been with had leg muscles or bulk that protruded out past their cock and balls making about half the length unusable for anal.
This could be interesting I immediately thought. I had not planned on getting fucked but figured that I wanted to try this one on for size.
We sucked each other for a bit and both were rock hard. I asked if he wanted to fuck me. He agreed and said yes.
I got out a bottle of lube and put it on his hard rod and my hole. I got on my knees, head down and he started to rub on my hole. I pushed back into him and felt the head pop inside of me. I started to rock back and forth and soon felt him deep in me. Sure enough, I could feel his balls rubbing on my hole. He had every centimeter of that cock inside of me. It was a little uncomfortable but not bad. After a few minutes he pulled out and I lay on my side with one leg up. He lay on his side behind me. He slid the head of that magnificent cock against my man pussy and it went in so easily! I could feel the head pop out inside. It was magnificent! I know that I gasped when he started to stroke it deeper.
Immediately I felt something totally foreign about this. Every stroke brought a wave of mini orgasms thru my lower body. I finally recognized that he was massaging my prostate with the head of his cock. It was so different and so pleasurable! I wanted more. After a minute of so of that I could feel my cum rising. As he stroked in and out I gushed great ropes of cum all over the bed and shot it as high as my mouth. I had a glob of cum on my lips. And at NO TIME had my cock been touched!!! My first prostate orgasm and man was it good! When I was finishing my orgasm I heard him gasp and reach over and grab my cum drenched cock in his hand. He pulled me back onto his cock and shot a huge load inside of me. He jerked and moaned, crying out as he spent his load inside of my tightened hole. We were both wasted. It took a little while but we got up and agreed that this was more than an exceptional fuck. We met again the next week and did it again, just as intensely as that first time.
We would meet when time allowed at least once a week or more for several months. We would sometimes fuck and other times suck each other to orgasm. It was all good! He always buried every fraction of an inch of that hard cock inside me when we would meet. That protruding pelvic area was the first and only one that I have ever seen but it was better than fantastic for getting deeeep inside.
He moved away about a year later. I have not felt another like that since.

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