Tag: older men

Sorry I haven’t been posting very much recently, I’ve been busy being out of control. A life update: my boyfriend and I broke up which means I’m now ~single~. A side effect of that means my blog will probably be more exciting in the coming months, because I’ll no doubt be getting up to more ridiculous/tragic sex stuff now that I live a life without rules. It’s weird–we broke up right around the time I quit my restaurant job, so I suddenly feel very “free.” That sounds cheesy, but it does feel significant that for the first time in my life I don’t have a boss, I have no obligation to be anywhere at any specific time, I don’t have to tell anyone what I’m doing or where I’m going, and I don’t feel tied to anyone or anything. Everyday I wake up and think, “I can do whatever I want.” It’s sort of cool, except recently the “whatever I want” has been getting drunk on vodka martinis and having accidental group sex, which is not very productive, I know, but I just got out of a 2.5 year relationship so give me a break.

I have lots of things to tell you (and by “you” I mean a group of random internet people I don’t know–blogging is weird), but I’ll limit this blog post to two stories. Story 1: I was recently set up on a blind double date by a friend of mine–I’ll call her “Kate.” Kate is dating this older rich guy who she really likes, and she asked if she could set me up with his friend–a funny, handsome, divorced entrepreneur. She said, “He’s fifty but he doesn’t seem fifty. He seems, like, young.” I said a young-seeming fifty year old sounded fabulous, and that as long as there would be martinis (low carb) I was down. Plans were then made for a Monday night double-date at a restaurant in the West Village. Unexpectedly, the night before our dinner I got a text from my blind date saying, “What’s your address? I will be sending my driver to pick you up,” which was an early positive sign. I couldn’t help but think of Big from Sex and The City, who (embarrassingly?) was my only mental reference for a person with a personal chauffeur.

When I got to the restaurant I was sort of nervous because I’d never been on a blind date before, but the guy was totally hot–tall, dark haired, Jewish (my fave)–and I immediately thought, thank fuck. So we were drinking at the bar and the three of them were sort of drunk already, and I was like, “How did you guys get drunk so fast?” and my guys says, “We took Quaaludes, you want one?” So obviously I said, “Uhh… I thought those stopped existing in the 80s” and he responded, “They did, but I have my own chemist who makes me whatever I want.” At this point I thought, score.

So we ate dinner and drank more, and by the end of the meal things were sort of fuzzy in a good way. Then suddenly Kate’s boyfriend suggested we get a penthouse suite at the St. Regis hotel to “hang out” in. I thought that was sort of weird, since both guys have apartments in Manhattan, but I was like whatever. So we get to the hotel and they ask for the penthouse and the hotel guy says, “That will be $5,500” and they pay for it like no big deal. Meanwhile I’m standing in the lobby drunk and barefoot, holding my high heels, with my eyes 75% closed because of all the downers.

In the room suddenly more pills and champagne appeared, along with casual stuff like chocolate covered strawberries and silver platters covered in miniature cakes. And then we got more wasted and had an orgy (duh) which at one point involved me getting fucked and sucking dick at the same time (life goal achieved), and I don’t know… a bunch of other stuff happened that I can’t really remember, but I know it was fun. And then in the morning Kate and I woke up alone because the guys had both gone to work, but since we both don’t have “real jobs” we just laid in bed all day and ordered room service. At one point Kate said, “God, isn’t it so much better dating guys who aren’t indie?,” and I laughed and agreed and then we high-fived in slow motion.

But moving on, story 2: I have also been dating a girl. (OH MY GOD I’M GREY AREA.) I suppose it’s not that weird, as I’ve been sleeping with women casually for years, but this is different because it’s not just a one-off sex thing–it’s been going on for months, and there are “feelings” (eww) involved. Seriously though, I never thought I would actually date a girl. I just couldn’t imagine myself being into the dynamic, because both in sex and in sexual relationships I tend to be ultra submissive and crave male dominant energy. However, this girl looks and acts like a boy, so it works out! (Actually she sort of looks like my ex–awkward.) What’s cool is that she has all the qualities I look for in guys (dominant, tall, in control, wants to bend me over stuff and spank me, etc.), except she has the sensitivity of a woman (good), and is just generally less of an arrogant dickhead than most men (also good).

For real though, she does make me feel “confused.” Like for the first couple weeks, every time we would hang out or have sex, I couldn’t get rid of this constant voice in my head going, “I’m dating a girl, I’m dating a girl, I’m dating a girl.” It was like I was too hyper-aware of what was going on to be fully present in the moment. But I got over that and now all I think is OH MY FUCKING GOD THE SEX IS SO GOOD. Seriously, having sex with a girl makes sex with men seem so dumb. It’s like duh, obviously girls are going to be better at making girls cum, because they know what they’re working with. I cum every time we have sex, usually multiple times. That’s craaaazy to me. (Sex and orgasms TOGETHER–what the!?) Like I bought a strap-on because I was like, “This is what lesbians do, right?” but we barely even use it because I legit don’t miss dicks when we fuck. And if I really missed what it felt like to be fucked by a dick, I could always just go to the bathroom and insert a tampon :)