15. Finding older women on Craigslist
“33yo male, I’m into older women, like middle aged or more, always have been (sorta). I’ve found and met up with 4 over the years, all from Craigslist, 3 resulted in sex with 1 becoming a relationship.
The first was 59 (I think), I was 28. We initially met for breakfast, then went back to her place for sex. This led to weekly meetings that lasted 3 or 4 months before she decided to completely stop talking to me. I think I got too close, but she also had her own issues. She had similarly cut off several people in her life including her sister and her parents who both died before she ever spoke to them again. The sex was all right and I learned a lot about women. I was only into men up until that point but had always been curious about women, specifically older women, and she was my first. We didn’t use protection as there was no chance of pregnancy, which was not smart, but I don’t regret my time with her, only the way it ended.
After a yearlong dry spell I met another woman at 29, she was 64 very fit and had implants (they were rock hard). She was crazy but not cut-your-dick-off crazy. She had this need for cock, she almost exclusively would come by to blow me which consisted of her almost desperately gorging herself on my cock trying (successfully usually) to get me to cum three or four times in a row. I ate her out a few times and we had maybe eight or nine thrusts worth of vaginal sex but for her it was pretty much all about fellatio and her doing things to me. She had all kinds of toys, mostly vibrators she liked to tuck here and there while she blew me. She would also often ask if there were any weird things I’d like to do to her. She’d often suggest things like putting a speculum inside her to spread her open, and using other toys on her. She moved several states away after a couple months and before things could get too freaky.
The third one a few months later was an erratic late 50s woman whose life revolved completely around her dog, it was one of those service dogs that soothe the elderly and the terminally ill. She had some kinda semi regular spot on the local news with her and her dog. Anyway we never had more than a couple dates and it was pretty clear to me that any other human in her life would have to compete with that dog and that likely had to do with why she was single. She was also the daughter of a fairly famous singer from the 60s. She lived with her and I got to meet her, her bathroom was full of old pics of her mom with like Sammy Davis Jr. and other celebs of the time. Hallway had gold records and whatnot, pretty surreal. Her mom who I shall not name, once told me ‘good luck’ with regards to our dates. Ha.
Last one was later that same year after I turned 30. She’s 29 years my senior and we’ve been in a loving relationship for almost 4 years. I intend to be with her until she leaves this earth. I’m an atheist and have always been a huge skeptic, but I felt almost right away like we had known each other for centuries and that feeling was mutual. Life is a crazy fuckin’ ride, and the rules of society are not set in stone. Do what’s right for you.”
16. Meeting guys and girls on Tinder
“Met 3 guys (that I fucked) and I think 4 girls? I’m a lesbian, wanted to see if I liked guys, so I got with 3 guys from these apps. First guy I got lucky, he was so great at sex. I was like I might actually be bi, I kept seeing this guy for a month until I hurt his dick on accident while riding him. Gave another guy a try and it was so awful he was being so pushy until I was like fine, clearly he wasn’t used to getting some cause he didn’t know where my clit was and he came within like 5 mins, couldn’t get me very wet. Third guy I actually liked, foreplay was great and he made me cum, then when we ‘fucked’ he lasted like 3 mins. Even he was shocked and I was like uh, it’s all right. Didn’t feel like fucking again and I’m sure that I’m gay from those experiences.
From the girls I met, those are interesting. Two of the girls I got with were clearly straight girls that were experimenting. They told me they were bi and when I got with them they also could not find my clit, and didn’t do anything that felt good. So now I’m weary of getting with a straight girl, and if I do, I need to know that she masturbates with her hands, otherwise when she’s trying to get me off she won’t even know what feels good. So another girl was just a hookup, but I liked her, never talked to her again though ’cause I got with her on vacation. Last one, well, actually the first person I fucked from Tinder was actually my first time with a girl, took things slow like one would with dating, things were going so well with this one, I liked her a lot and was feeling optimistic, started catching feelings. But later she told me it wasn’t fair how she’d been treating me, and that she had a girlfriend, and she was cheating with me. This kind of pushed me off the deep end, I went a little crazy temporarily, I started smoking more weed than ever, and got fucked up 3 days straight on Nyquil…clearly my reasoning wasn’t great in this time so I said a lot of shit I shouldn’t have and she basically thought I was insane and told me that. So yeah, basically average experiences. I’m addicted to the weirdness of meeting people off apps.”