Bi-Sexual Male / 34
First Time Bottom
I had never been with a guy but wanted to try. Was talking with an older guy on-line who wanted to be my first and I needed the guidance so we met at his place. He was a gay guy who often played with bi-guys and clearly enjoyed being the first to top a new bottom. The first try was mostly me giving him head, getting used to pleasuring a guy, him fingering me, loosening me up, then we tried and it was too painful. Instead I was able to finish him off with my mouth. I was regretting getting with him first because he had a very thick dick.
The next time we went slow, lots of sucking and fingering, stretching and it was again just too painful. He was an understanding guy. He asked me to trust him, got me on all fours, ass up at the edge of the bed and he blindfolded me, said he's done this before but didn't want to see until after. I felt his hands massaging my ass, multiple fingers sliding in, heavily lubed, pushing firmly, uncomfortable but not painful.
Then he slid something hard and thin up my ass. A little at first then deeper and deeper. The deeper it went the wider is was. It was stretching me out but not in a painful way. He withdrew that and slid something similar in which was the same texture but wider. He pushed it in slowly, at first it was uncomfortable at its base then it began feeling good. Then again with another which was wider at the base still. Four times he fucked my ass with the same shaped item which was a little longer each time and wider at the base stretching me out. Then a different shape, thicker initially, a little painful at first then it was in and filled me. I could feel it sliding deep inside, my ass stretched, very uncomfortable but no longer painful.
The guy slowly fucked me with it. I assumed it was a dildo. He fucked me a little faster and faster and it started feeling really good. Still uncomfortable but no pain and eventually it was very pleasurable. I felt if he fucked me harder it would make me cum.
He finally withdrew it when I was close to cumming. I was moaning and enjoying it when he slid it out with felt like a big release. Then immediately I felt pressure and something bigger was pushing in. I said to myself oh shit then felt a painful stretch that made me gasp, I said hold it, he said "trust me" and he pulled my ass up and the pressure grew worse. I could feel me ass stretching around what turned out to be his cock. The head was pushing in, my ass was resisting, I nearly yelled stop but held on and then it was in, sliding deep, stopped, a little back and forth and then balls deep. He held my hips, slowly drew all the way back then all the way in, over and over and soon he was going faster and then faster and he was fucking me and it didn't hurt. It was uncomfortable for the first few minutes but once he was pumping faster I realized it just felt good. Very good.
He fucked me for about ten minutes and had gotten into it, started slapping my ass, pumping me hard and fast, stroking my dick, then he was committed, fast and hard, his balls slapping with each plunge, I felt my orgasm rising and as i started cumming, he thrust slow and as hard as he could, filling me with cum. He slowly finished, staying inside as long as he could, leaving every drop he could in me before finally withdrawing.
After, I saw that he had used a serious of carrots, each bigger than the last, followed by a large dildo to get me ready to fuck. That's right, carrots. He laughed and said he's done it before but didn't think I'd go for it if I knew.
So I'd managed to bottom a guy with a huge cock and it took a little while to recover but I went back a bunch of times and he never used carrots again but each time was a struggle at first then bliss. It eventually turned into an uncomfortable couple of minutes initially followed by awesome sex.
The best part was he arranged a threesome with another guy once who had a smaller dick. He was only about six inches long and not nearly as thick as the other guy and when he fucked me it just slid right in, no pain no discomfort just pure pleasure.
Occasionally I'll get with a hung guy now and then. Yes it's still starts out uncomfortable at first but I can handle it and it becomes very enjoyable. Regular sized guys are no problem at all. They can easily fuck my brains out.
The next time we went slow, lots of sucking and fingering, stretching and it was again just too painful. He was an understanding guy. He asked me to trust him, got me on all fours, ass up at the edge of the bed and he blindfolded me, said he's done this before but didn't want to see until after. I felt his hands massaging my ass, multiple fingers sliding in, heavily lubed, pushing firmly, uncomfortable but not painful.
Then he slid something hard and thin up my ass. A little at first then deeper and deeper. The deeper it went the wider is was. It was stretching me out but not in a painful way. He withdrew that and slid something similar in which was the same texture but wider. He pushed it in slowly, at first it was uncomfortable at its base then it began feeling good. Then again with another which was wider at the base still. Four times he fucked my ass with the same shaped item which was a little longer each time and wider at the base stretching me out. Then a different shape, thicker initially, a little painful at first then it was in and filled me. I could feel it sliding deep inside, my ass stretched, very uncomfortable but no longer painful.
The guy slowly fucked me with it. I assumed it was a dildo. He fucked me a little faster and faster and it started feeling really good. Still uncomfortable but no pain and eventually it was very pleasurable. I felt if he fucked me harder it would make me cum.
He finally withdrew it when I was close to cumming. I was moaning and enjoying it when he slid it out with felt like a big release. Then immediately I felt pressure and something bigger was pushing in. I said to myself oh shit then felt a painful stretch that made me gasp, I said hold it, he said "trust me" and he pulled my ass up and the pressure grew worse. I could feel me ass stretching around what turned out to be his cock. The head was pushing in, my ass was resisting, I nearly yelled stop but held on and then it was in, sliding deep, stopped, a little back and forth and then balls deep. He held my hips, slowly drew all the way back then all the way in, over and over and soon he was going faster and then faster and he was fucking me and it didn't hurt. It was uncomfortable for the first few minutes but once he was pumping faster I realized it just felt good. Very good.
He fucked me for about ten minutes and had gotten into it, started slapping my ass, pumping me hard and fast, stroking my dick, then he was committed, fast and hard, his balls slapping with each plunge, I felt my orgasm rising and as i started cumming, he thrust slow and as hard as he could, filling me with cum. He slowly finished, staying inside as long as he could, leaving every drop he could in me before finally withdrawing.
After, I saw that he had used a serious of carrots, each bigger than the last, followed by a large dildo to get me ready to fuck. That's right, carrots. He laughed and said he's done it before but didn't think I'd go for it if I knew.
So I'd managed to bottom a guy with a huge cock and it took a little while to recover but I went back a bunch of times and he never used carrots again but each time was a struggle at first then bliss. It eventually turned into an uncomfortable couple of minutes initially followed by awesome sex.
The best part was he arranged a threesome with another guy once who had a smaller dick. He was only about six inches long and not nearly as thick as the other guy and when he fucked me it just slid right in, no pain no discomfort just pure pleasure.
Occasionally I'll get with a hung guy now and then. Yes it's still starts out uncomfortable at first but I can handle it and it becomes very enjoyable. Regular sized guys are no problem at all. They can easily fuck my brains out.
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