“One day I’m going to spank you till I come,” he threatens. He gets behind me, close enough that I can hold on to his dick while he lays into me. The Spanking Man wants to try out his new cane. We start making out and he asks if I’m ready for “discipline.”ħ.30 p.m. At the Spanking Man’s apartment, which is extremely nice - immense, penthouse, beautifully furnished. The Scruff man and I exchange pictures, at which point he says, “Oh, sorry - too old for me.” I sort of knew from his profile he’d say that, but can also be a bit of a glutton for punishment.ħ.15 p.m. “In a relationship,” I hinted back, maybe I’d consider it. This hard limit has been an issue for a lot of guys, including R., who hinted the time we hooked up that in a “relationship” he’d need that. I haven’t had anal sex in years, and my last experience with it was unpleasant. I come across a Scruff profile that is appealing - older guy, aggressive, visiting, not looking for, ahem, butt stuff. I told him I was growing my hair out is it a good sign that he wants to see what it looks like? Does it actually look terrible? Oh God.Ģ p.m. has texted, asking for a new picture of me. It feels a lot like having a big brother come visit.Ħ a.m. I put them on my calendar and am happy there’s something to look forward to. At home, I take a shower, order dinner, message D., who has dates for his next work trip to New York. I have tried several places to find the least annoying one, and at least the music here is good, though.ĩ p.m. We settle on hanging out tomorrow after work.ħ p.m. He texts me, asking why I messaged him on “one of those apps.” I say I broke my phone, but the truth is that I deleted his number a few months ago, after I asked him point-blank to go on a date with me and he waffled. It never rains but it pours: Grindr tells me that the Spanking Man - another guy in his 50s - is nearby, and I send him a message. Stuff at the office has piled up, but the overload works for me I like being busy. Scrolling through Meetup groups, signing up for things I know I will never actually do.ġ0 a.m. I wash my face and check my work email.Ħ p.m. Soap will get semen off ceramic, right?ġ p.m. Eventually we compromise and I get a bowl from the kitchen. Unfortunately, I know exactly how clean my floor is, and as much as I hate saying no to him, I’d rather not. is like on a bad day, I’m here for it.ġ2.40 p.m.
![older men trying first gay sex stories older men trying first gay sex stories](https://media-cldnry.s-nbcnews.com/image/upload/newscms/2021_25/1740944/the-old-gay-te-main-210625.jpg)
As soon as the door closes, he puts his hand on my neck and pushes me down on all fours, and makes me crawl to the couch while he kicks me. is here - this is the only way I know his name, and for all I know it’s fake. My job may be the only source of meaning in my life - I work as an associate at an international nonprofit media company- but practically speaking, most of the team that I deal with is not even in this time zone, so half of them are asleep anyway …ġ2 p.m. Yes, I will totally bail on work for this. He’s near my apartment and wants to meet on his lunch break because he’s mad about something. I want him more than he wants me, and both of us probably enjoy the power trip. We’ve hooked up a handful of times over the past few months - he comes over, I blow him, he smacks me around - but lately he is a hard man to trap I don’t know if he’s playing hard to get or if he’s just busy. This reopens our usual discussion about why in my head and bed those things are entirely separate.ġ1 a.m. K would run too wild with, so I just say that I love D. Start the week off right: therapy! My doctor keeps trying to convince me I’m into D., who is straight, and I find the idea ludicrous, although I did briefly have a crush on him in high school.
![older men trying first gay sex stories older men trying first gay sex stories](https://m.media-amazon.com/images/I/51lzMwSP7GL.jpg)
lives far away, so things like this are important to me - low-key, regular communication that makes me feel like we are still part of each other’s lives.Ĩ.30 a.m. Wake up to a message from my high-school friend D. But if you are going to be isolated, New York is not a bad place for it.Ħ a.m.
![older men trying first gay sex stories older men trying first gay sex stories](https://m.media-amazon.com/images/I/513sjz0B50S.jpg)
Having lived here two years, I am beginning to worry that this is just what life is going to be like - entirely silent weekends. I am pretty sure I did not exchange actual, out-loud words with anyone today. There’s nothing wrong with starting to drink by yourself at 5, is there? I send a message to R., open-ended enough that he will at least have to reply.ġ0 p.m. Suddenly it becomes very important to get specific groceries from a store in Queens.ĥ p.m. It’s been a useless day I haven’t accomplished much.
![older men trying first gay sex stories older men trying first gay sex stories](https://www.history.com/.image/ar_16:9%2Cc_fill%2Ccs_srgb%2Cfl_progressive%2Cq_auto:good%2Cw_1200/MTU3ODc5MDg3MjQ3MjA1NzA1/campaign-for-homosexual-equality-rally.jpg)
We went on a date once, when I lived in his city a couple years ago we hooked up once last year when he came to New York and now we have a semi-regular, slow-moving exchange.ġ2 p.m. The “relationship” with this man (he is a gray-haired man in his 50s, which is apparently my emotional jam) exists entirely inside my head. This week, a single man trying to work through his intimacy issues: gay, single, Harlem, 30.ĩ a.m.