This was asked by an anon. His ask was too long to fit in one submission, so this is just me putting them together. Anon asks:
“Last week I was out of town and a guy started talking to me on grindr. He didn’t have a profile pic or any information at all but I gave him a shot. It turned out he is 34 and he seems to be into much younger guys. I told him I’m just looking to chat with other gays since I’m new to the whole community, but he keeps calling me shit like cutie, honey and pretty and it’s getting really awkward. (See next message for the full text, please.) (See previous message for the full text, please.) Everyday he’s asking me multiple times how I’m doing, what I’m up to and that he wants to skype or meet me, even though he’s living about a 100 miles away from me. I’m not the kind of person who blocks people out of his life and hurts them intentionally, especially if I might see him on the streets (not sure if I’m moving to that town). It starts to freak me out and I don’t know how to proceed. Any suggestions?”
I’ve encountered things like that before, in which someone I was not interested in at all was just overly nice and talked to me very sweetly. My best advice is just to bring it up that you are only interested in being friends, and nothing further. Some older men (40’s and even 50s) who I have talked to have become pretty good friends of mine, and they have been around the gay block many more times than you or I have. They are usually pretty good about listening to your problems and giving you advice. And a lot of the time, they are not very judgmental. Now trying to meet you and skype you might seem a little weird to you. And if you’re not comfortable with that, let him know. (I don’t even like skyping with friends.) If he takes it badly, then whatever, he was after something that he wasn’t going to get. But I believe if you’re mature about it, he’ll be mature as well.
I don’t know if I’d really consider it a hookup. But here we go: I was going out with this 18 y/o a few weeks during the summer and he made it clear to me that he was a bottom. We had talked dirty, he blew me in his car, etc etc. So my parents are out of town the last week of July (I’ve moved out since then) and I invite him over to stay the night and do whatever. After a movie, we go to my bed and he begins to blow me. 5 minutes in, I recall him mentioning that he likes to be face-fucked, so I grabbed the back of his head and began thrusting a bit. Whenever he started gagging too much, I’d slow down and allow him to catch his breath. After a few times, I got really into it and thrust really hard, which triggered a loud gag, and then him throwing up on my bed spread. I sent him to the bathroom while I threw everything in the wash. After he had recovered and I laid out new bedding, he decides he wants to bottom. So we get warmed up again, I lube him up, and I get about halfway in when he basically yells to pull it out because it hurts to much. I lubed him up some more, and tried again, to the same reaction. We tried a couple more positions until he wanted to try no more. So he ended up just jacking me off and we called it a night. Needless to say, we didn’t mess around again.