Many men I’ve slept with have asked why I switched from topping to bottoming. Here’s the real story.

My first gay sex was with a kind, gentle top. The first few times he fucked me were uncomfortable; soon it felt good. He offered to switch, I topped him once, felt that incredible tightness and heat, and never wanted to bottom again. I loved seeing a man’s face as I entered him, feeling him clench around me.

Twenty years and many bottoms later, I met Frank, a science professor. We’d traded blowjobs a couple times. One day, while he sucked me, he secretly teased my hole with a dildo, then slid it in. Memories of the stretch and prostate pressure flooded back. When he asked to fuck me, I nodded. His fat 6-inch cock stretched me more than the toy. He lasted 20 to 30 minutes, stroking me while hitting my prostate over and over. I came harder than ever, full-body contractions, cum everywhere, orgasm lasting a full minute. After that, I was hooked on bottoming again.

In my late 60s, erections softened and load size dropped, but my hole grew more sensitive. Touching or licking it got me craving penetration. Now in my late 70s, I prefer thick cocks, about 6 inches long, 6 to 7 inches around, for the best stretch and prostate pressure.

I hadn’t seen Frank in 10 years. Out of nowhere he sent me a text, asking where I had been, what I had been up to. I responded, “Frank, so nice to hear from you. I’ve since moved about 40 miles from where I used to live, got divorced, moved in with a lady friend from years ago.”

After a few messages, Frank and I started sexting. It didn’t take many texts for it to get pretty nasty. Frank was talking about how he loved to eat my ass and watch it relax, pushing his tongue then fingers into me, thinking and wondering if I could take all five fingers and maybe his hand.

We never did try that, although he wanted to. We chatted about how I used to moan and my whole body would jerk and shake when I had an orgasm, with his cock buried balls deep in my tight hole. How he just loved to fuck me long and hard while watching my expressions, how when he came in me it felt so good.

Frank often took photos after fucking me of his cum dripping out of my hole, photos he still has, which he was supposed to share with me but never did. I was telling Frank how I had a FWB but hadn’t seen him in a couple months. Frank told me of his young college-age fuck buddy, how he usually fucks him, but is training him to be a considerate top man. As it turns out, Frank has gotten old also, and now enjoys the bottom bunk, like myself!

Frank and I started talking about getting together again. He still had his beach condo. The plan was to meet there like old times. We planned on a weekday, in two weeks, on a Wednesday. Why a Wednesday? Because that is commonly called hump day. Just an inside joke.

Frank texted me on Monday of that week to ask if it was okay to invite his fuck buddy to join us. I of course said, "Yes, sounds like fun!" On Wednesday we met. His name is Greg. A handsome young man in his 20s, nice build, probably 5’10”, not real muscular, awesome cock, 7” and thick. Bigger cock than Frank or myself. When I saw him I was really hoping today would be a training day for him to fuck me.

After introductions, we started off with a glass of wine and some nice conversation about his studies, Frank’s involvement with him, my lady friend, and my FWB. As we became more friendly, Frank suggested we all get naked and touch each other. I was getting excited to see both of them naked and taste some cock.

When Greg dropped his pants, his already hard cock was pointing up at a 45-degree angle. Damn, I sure do miss having a cock that will do that. As he sat back down on the chair, I moved in quickly and engulfed his cock. Frank’s comment was, “Once a cock hound, always a cock hound.” I sucked him and worshiped his cock, then moved down to his balls, lapping at them like a dog in heat, then on down with my arms under his knees and lifting his legs up so I had a straight line to his hole.

His hole was a little musky, just enough to make me want to taste him outside and inside. I licked and licked all over his rosebud, nibbled on his cheeks, stabbed my tongue and fingers inside him. He tasted good. I could have eaten his ass for hours, but Frank interrupted me by smearing lubricant all over my asshole. Frank pushed my face back into Greg’s ass and pushed his cock inside me. He just stretched me out in one fell swoop, actually took my breath away.

After a few minutes of Frank pumping into me, Greg said he wanted to watch. So onto my back Frank put me. Now with Greg sitting on my face and slowly licking my balls and sucking my cock, Frank fucked me for all he was worth. Finally we both orgasmed, me shaking and moaning with my face in Greg’s ass and squirting cum in Greg’s mouth, Frank going stiff as a board and ejaculating in my ass.

Frank was still inside me and Greg was still smothering me with his ass while also licking around my balls and flaccid cock. When Frank slipped out of my hole, followed by a stream of his white slimy cum, Greg watched all that cum drip and slide out of me. Finally he rolled over onto his back, letting my legs down to rest. The only one not to cum yet was Greg.

After another glass of wine and some conversation, Frank brought up that Greg still had a fresh load of cum to unload. Being the slut for cock that I am, I immediately offered my ass, which Greg quickly accepted. Greg wanted me to ride him, so he was on his back, holding his cock vertical. I just climbed up, lined my hole with his shaft, and settled down onto it.

Man, it slid right in. I stretched out to fit him snugly inside my ass. Greg was a slow pumper, just going in and out slowly. That felt really good. He was all the way inside me when I felt him stiffen and then felt his cock jerk like 6 or 7 times. From the look on his face I could tell he orgasmed.

He pulled me down for a wet kiss and whispered, “Just stay here. Leave me inside you. I’ll be ready to go in a few minutes.” We stayed kissing and rubbing. I actually started to get a hard-on also. Unbeknownst to me, Frank and Greg both took a Viagra. They planned to fuck me into oblivion.

I could feel Greg getting hard and he started to pump into me. Frank stood up on the bed and offered his hardening cock to my mouth, which I happily let him push inside. I ran my tongue all around the glans and up and down his shaft while listening to him tell Greg to keep me bent over and kissing. We had been engaged about 10 minutes, Greg’s cock in my ass, Frank’s cock in my mouth.

Frank pulled out of my mouth. I saw a smirk and wink towards Greg. Then Greg was frantically kissing me and rubbing my back, actually hugging me to him. I felt Frank grab my hips. He poured more lube on me and on Greg’s cock. Greg had paused his pumping. When I felt Frank’s cock nudging against my already stuffed hole, I pulled up from the kiss and asked, “What’s going on, you guys?”

Greg whispered, “Don’t worry. If it hurts too much we’ll stop.” Frank was lightly pushing into me, his cock on top of Greg’s cock. I could feel my hole stretching and a slight burning sensation. More stretch, then I felt Frank’s cock’s head slip in, then push in a little more. It was definitely painful, not so much that I wanted them to stop. I finally felt Frank’s pubic hair brush up against my ass cheeks. Then they started the alternating pumping.

The feeling was strange at first as I had a cock fully penetrating my ass all the time. I could feel the one go in all the way and the other one retreat just to the entrance, then all over again and again, until I could hear both men start to make a moaning noise, Frank saying “I’m going to cum,” then Greg the same thing. They both pushed in all the way at the same time. I felt it, both hard cocks pulsing, flexing, squirting, filling me up with cum.

After they both orgasmed, I could feel their cocks start to soften. Frank slid out first, then a few moments later Greg came out, followed by a stream of cum. I just stayed lying on Greg, exhausted from taking cock for the past hour. I know my hole was hanging open, gaping, as I could feel the cool air.

I just lay there and relaxed in Greg’s embrace, dozing a bit. Finally I felt it was time to move, so I just rolled off and lay between Frank and Greg. We all just chatted about the experience. They were apologizing for talking me into double anal penetration. I told them no problem, as it was something I always wanted to try, just never had the nerve to try it. We talked some more about getting together again.

In the end I still prefer men close to my age, with cocks in the 6” to 7” length and fat. Still a confirmed bottom.