Him: "I'll Be Your Sex Guru"

Me: "Did you just lick my butthole?"

It was 6:30pm on Wednesday, and I was making tacos. While stirring the ground beef, I opened the Feeld app to see if there were any promising new leads. I was about to be kid-free for a few days, my A/C repairman has been out of town, and I’ve been hungry (for more than just tacos).

An extremely cute 35-year-old popped up. Shaggy hair, blue eyes, amazing body, merely ten miles away. He wasn’t exactly my type — blond, and I like darker guys — but he was cute enough. I “liked” him and went back to my meat.

30 seconds later, my phone buzzed with a notification. He’d liked me back — and immediately sent me a text.

“Where oh where is 10 miles away? North, South, East, West?” he wrote.

We bantered a bit. He said he was in the area for a week because he was pet-sitting, but as it turned out, his actual home wasn’t that far from me, either. I realized time was of the essence if I was going to schedule something for the weekend, so after just a few texts, I wrote: “Well. Are you free at all this weekend?”

That upped the ante. “Yeah, I would love to do all sorts of things bad and good to you, absolutely,” he replied. We made a tentative plan to meet on Saturday morning — he’s a daytime hook-up guy, apparently, preferring to romp in the glow of natural light.

That night, when we texted about sex, it became clear he was a lot more experienced — and adventurous — than I was. He asked me if I had tried certain things and my answer was usually “no.” I got the distinct sense he was turned on by my lack of experience and that he wanted to be the one to expand my sexual horizons — which sounded fun and more than a little terrifying. He also asked me specific questions about my preferences, from “how do you like to cum?”(me on top!) to “would you prefer I vocalize anything risky I might escalate toward, or just escalate slowly?” (vocalize please!).

Although it can be awkward to discuss one’s sexual history and preferences with a stranger over the internet, I have grown to love these conversations because it’s easy to set expectations and ground rules via text. This is when I always communicate that condoms are non-negotiable, that I don’t do sleepovers, and that I will murder them if they bite my nipples. They must agree to the hook-up on my terms in advance, which makes the in-person stuff so much better once we get there.

That night, I dreamt that the 35-year-old produced copious amounts of saliva and licked me everywhere in a van after we escaped from a mutant reptile that had been stalking us. I woke up and texted him about it, and it turns out my subconscious mind was right: He admitted that he loves bodily fluids and grossness. After a few texts, he said that my neighborhood was actually on the way to his afternoon work commitment… Would I like him to come over right now?

I did the math. By the time he got to my place, we would only have an hour before I would need to kick him out to get ready to meet a friend for lunch.

“Let’s wait until Saturday,” I wrote. “Although I’m probably going to regret saying that in 3… 2… 1…”

An hour later, he rang my doorbell.

He was hot. Like REALLY HOT. He had intense blue eyes. He walked into my house, said hello to my cat, and wandered into my bedroom.

“Oh, I didn’t mean to walk right into the bedroom,” he said, but yeah right.

“That’s okay,” I said. He picked me up. What was happening? He instructed me to wrap my legs around him. He kissed me and then threw me on the bed and undressed me.

The foreplay and sex were intense. He knew his way around a clit. He told me what to do and when to do it and moved my body around himself. (Did I mention he was muscled? Omg.) He thrusted deeply, in many positions. He slapped my butt. But when he did things I didn’t like — like when he put his hand around my throat at one point and I told him no — he immediately stopped.

This was different from the other sex I had been having. It was fun and thrilling — and also scary. Physically, I liked being dominated. Mentally, though, I had some trouble with it. Haven’t men controlled women’s bodies enough already?

After he left, he texted: “Was any of that too much for you?” I told him no — I mean, except for the choking. Then he asked if there was anything I wanted more of. I admitted that I missed having build-up — we had gone straight to the bedroom without building any sexual tension in person. So we agreed to meet again on Saturday for brunch, first, and then he could come over. I wanted to converse with him, observe him, undress him with my eyes before he ended up back in my bed.

There is a certain type of man I’m encountering on Feeld — and this guy is one of them — who likes to be a teacher. Oh, middle-aged woman who has spent a lifetime in a sexless marriage, let me introduce you to all the forms of pleasure you have missed. They are quick with cryptic and arrogant comments like “you have so much to discover” and “I might just change your life.” I am ambivalent about these men, to say the least. On the one hand, yes — I openly admit that my sexual experiences so far have mostly been pedestrian. And sure, I’d like to change that. On the other hand, I don’t appreciate their patronizing comments and the implied sexual hierarchy. At one point during our Thursday morning hook-up, the 35-year-old licked my butthole and I squealed, mostly out of horror. Later, he texted: "You’re so squeamish, it’s so cute.” Mmm. No thanks.

On Saturday, he and I went to brunch. The food was delicious; the company, not as much. He talked a lot about himself. He engaged with the wait staff in an affected and entitled way. He was a little too flamboyant. He touched me a lot.

But did I still want to fuck him again? Yes! Because this is the thing about post-divorce sex, at least for me: red flags are fine. Red flags are good. I’m not looking for a husband, or even a boyfriend. The fact that this guy is somewhat insufferable is a gift, because it ensures I won’t get too attached. So yeah, I’ll still sleep with him, if the sex is good and I want to. (Of course, there’s a point beyond which insufferableness blunts the libido.)

In the parking lot of the restaurant, he said he would follow me home but that he’d drive slowly — and that I should go inside my house, undress except for my underwear, lie on my bed and wait for him.

I did as directed.

This time, he was bigger and harder. The sex was more animalistic and acrobatic. There were moments when I felt like my entire existence had been consumed by deep, full-body sexual sensations. We did it standing up, we did it with me squatting on top of him, we did it all the ways.

Not that it was perfect. The low point — and boy, was it ever a low point — was when he unexpectedly and very vigorously spit into my mouth. I started dry heaving. Suddenly there were tears streaming down my face as I tried my best not to vomit chicken and waffles all over my bed.

“Well I guess we now know you don’t like that,” he said. We both laughed. But also…. why didn’t he ask for my consent first? What about “vocalize, please!” did he not understand? I shrugged it off and we kept going, but many hours later, I would come to realize I felt violated.

Once we finished, he showered. I pointed out the large red handprint on my butt in my bathroom mirror. “I do like seeing you wince,” he said. “But I don’t know how much of it you’re enjoying, and how much if you’re just tolerating.”

“I don’t really know yet, either,” I admitted.

It’s true. I like that the 35-year-old is introducing me to new kinds of pleasure and new ways of experiencing sex. And I get that, as with any new and slightly risky experiment, there will mistakes and moments I dislike or regret. But it’s hard for me to wrap my head around just how far I want to go, which and whose lines I want to cross, and how to discern when I’m doing things for the wrong reasons.

I have always found it hard to tell the difference between wanting to try something because I’m curious, and wanting to try something to please the person I’m with. I never want feel pressured into doing things for a man’s enjoyment — and I’d like to think that I would not, at this point in my life, give into such coercion if I felt it. But as a woman who’s spent a lifetime sacrificing my own needs for others, I can’t always be sure. Old habits die hard.

I’m hoping I can find a happy medium between exploring new things and respecting my own limits. And although I’ll say yes to sex even when I don’t want or need everything else a man has to offer, I want to explore my blossoming sexuality with men who treat me as an equal — not as a project.