First time with a man.
As a straight guy, I’ve often thought about bottoming, and then finally, one night, I showed up to somebody’s house. This is that story.
A few days ago, someone reached out to me on this app. Said they saw my post/comment about being interested to be turned. And they wanna help.
We chatted a little bit, and exchanged photos. He asked he if I had ever tried dildos? I said NO. But I’ve tried plugs. He said well that might be a problem, cause he’s 8 inch BBC.
We both agreed that it would be a big problem. But at the same time, i said that it would be a wonderful first time welcome if we can make this work.
He said, he thinks we could. Then I asked him gazillion of questions about preparation and stuffs. He told me it ain’t his first rodeo. He has all the accessories for clean up and stretching. all i need to do is, show up.
I asked him if he likes cages on bottoms. Cause i personally like the hung top and locked bottom dynamic. The difference is very hot. He said he’s into that too. So it was decided that I’d get my cage with me.
So we decided to give it a shot. He lives in the same borough (NYC), and not far from me. So he gave me his address, and we decided to meet later that night.
So i finished my work, took a shower, and showed up at his place at around 11.
He welcomed me. We sat on his living room watching YouTube and talking about random stuffs. Getting to know each other. And we were vibing good.
So after a while, i said let’s get to it. I asked him if he has ever put anybody in a cage before? He said no. So I gave him my cage, and told him to put in on me. He undressed me, and tried to put that thing on me, but he couldn’t cause i kept getting hard.
So we finally managed to get it locked with me helping him.
Then he gave me enema bulb, and the bottle of lube, and told me what to do.
I went to the bathroom, and took forever to get it done. As it was my first clean. I cleaned myself, and also took another shower in panic mood.
Then i told him I’m ready, and he said let’s move to the bedroom.
Once in the bedroom, he told me to get on all four. And when i did, he stated rimming me. Which felt awkwardly good. But i was still nervous.
After a while, he took some lube, and started with a small prostate toy….
It was little, and pretty soon it was going in and out without any issue. Although i was making lots of noises cause i had pushed lots of air in me with that enema bulb.
Next, i laid on my back, put my feet up, and he was positioned about my ass. And taping my cage, and ass with his effect di**, which was pretty hot. The whole dynamic of a caged long, and a BBC next to it is super sexy. Wish we had taken a photo. Both of us could that hot.
we moved onto the next toy, it was regular 5 inch dildo with balls and suction cup at the base. We had some difficulty getting it in, and had to use fingers to coordinate the opening.
It was difficult, so we decided to try the riding position, that way i control the pace.
And it worked, i just sat on it. Slowly, and we got it in. All the way. And he told me to just lie there and let my body get used to it.
I did, and it was painful, and strange. Cause the body just wanna push it out.
After a while, i took it to the floor, and rode it for a while, trying to get used to with the back and forth movement inside.
By this time, we were one hour into it, and used gallons of lube. I was the one pushing, and doing the work as i know my body and angles better. He was just sitting very close to the hole, and enjoying the show, making comments like yeah, it’s opening up. Push, close, open. Etc
The other thing he was doing is, providing lubes, as much as i needed. And by then, we had used gallons of it. I was leaking a lot in my cage, and him, every once in a while, would just take my pre cum with his finger and rub that onto the toys, or my hole as lube. Which was pretty hot. Haha
Onto the next toy, which was an ultra realistic 7 inch dildo with 3D veins and an upward bend. It’s probably the closest to the real thing I’ve ever seen for a dildo. Soft, thick, and suction cup works really well.
It was close to his 8 inch BBC, but still less both in thickness and length. But we decided if we can get this in, next is him.
So we started once again with the tip, it all seemed like we went back to the beginning again.
Despite trying different positions, and loooots of lube. We just couldn’t get it in more than the tip.
I thought if the tip is in, we’re good. But something inside (he said it’s the second ring) just seemed to be closing. And not letting anything in.
So we tried for a while, but it just didn’t work. By then it was more than 2, so we decided to call it a day.
Ending:
I wish he had set up plugs, that way we could work our way up. But man was an advanced player, and all he had was big toys.
In the end, i took off my cage, and we stroked each other, my dih was ultra sensitive from being locked and shrunken through multiple erecting. So i came within minutes.
While I managed to get him hard by stroking, but he lost it midway. And couldn’t cum. Which he said, happens, don’t worry about it.
Then went to the shower, and washed myself, and got dressed. He was vacuuming, and had tons more cleaning up to do.
We then talked a few more minutes, laughed, and said our goodbyes.
I felt bad stepping onto the street, thinking we could have succeeded if it was any average 6”, cause after all the work and time we put in, not getting the deed done was a big L.
I have learned a lot about body, bottoming, lubes, toys and sensations that night, which i could have never from all the reading, and watching videos. You learn by doing. That’s the only way.
Anyways, that was my story. If you’ve made it this far. Hope it was worth your time. Cheers.