My first attempt at bottoming was at 25. I had fooled around with other guys in college, including topping them but never bottomed. There was a fear there - not so much about the act but more about what it would say about me, what it meant - you guys know what I mean. I also chalked up all of that play to “experimenting” - I know, the things we tell ourselves!
Anyway, there I was at 25 in one of those old AOL chat rooms, started having direct convo with one guy who turned out to be a guy from another college I knew - our clubs used to play rugby - and yes we had fooled around after matches. I’m excited as he was pretty hot - hairy, thick muscled redhead. We make plans to meet up at a gay bar down in the Village, and we’re all over each other from the get go.
All very familiar territory until he starts paying attention to my ass - he’d never done that before but I liked it. All this play continues as we have some drinks and talk. I remember thinking “holy shit! I think he wants to fuck me!” and while excited at the thought, was nervous both as a virgin and because his dick was/is super fat. Later on we’re making out and his hand slips down my shorts and undies and his finger starts stroking/rubbing my hole - at that point I just broke the kiss and asked if he wanted to come back to mine.
We went, get naked and we’re on my bed reacquainting ourselves with our naked bits for awhile. When it came time for the main event, he asks about lube, condoms. Having not had any gay sex since the “experimenting” in college, I had no lube! I remember him giving me this sexy smile and saying “don’t worry, I’ll get you ready” and he proceeds to rim the motherfucking life out of me! I am literally begging for his dick now and he obliged.
Yes it hurt going in, but I was so keyed up I didn’t care. Eventually the pleasure started to overcome the pain. We fucked a few times that night, I can still picture him on top of me - our hairy chests all sweaty and tangled, his thick bush against me, making out and moaning into each other’s mouths. It was a wonderful night and it was thanks to him I got over my fear of bottoming. He and I continued to play on occasion and actually wound up playing with different rugby clubs which always included some after match play - usually in his truck before the drink up.
Most guys still wanted me to top (I’m 6’3” good looking hairy blonde jock with a fat piece) but thanks to my buddy, I could now add “bottoming” to my repertoire. But the more I did it, the more I wanted it!
It was about 6 years later, I had been playing with a new buddy - tall really muscular smooth Latin who was into hairy white guys and was all top. He did not have a huge dick as one might think a Latin would but what he had, oh my did he know how to use it! It was thanks to him I experienced my first hands free cum and my first cum when soft. My interest in topping waned with him and I enjoyed being a bottom. I still would top, but always made it clear I much preferred it on the bottom.
Now at 47, I’ve experienced a good variety of men as hook ups, friends with benefits, and boyfriends. I can tell you bigger is not always better - it’s all about the skill of the captain vs the size of the boat. I’m happy being a bottom and now a daddy and am thankful to be able to report there are plenty of guys out there who want a daddy bottom. And no, these are not paid companions.
So, first time bottoming at 25, last time bottoming at 47 - last weekend with a younger friend with benefits who loves daddies who bottom. Who am I to deny him?
