This is a long one, so brace yourselves.

This boy has just left my house, I’ve grabbed my laptop and there are a few things that are clear:

1. I’m chugging water to make sure I pee again and don’t have a UTI.
2. I think I tried to pressure this guy into having sex?! ME?! I’m the bad person in this scenario?!!
3. I’m pretty pissed atm. (As in drunk)

I drank the wine that was gifted to me and my housemate by neighbours and now I feel bad about this. I’ve also learnt a lesson about consent from tonight. And also I acted as a therapist for this guy, who had recently broken up with his girl friend, so hopefully he learnt lessons from me too.

Meeting him

I just sent a couple of messages to my recent Bumble matches just asking them for a date. To this guy, it was:

Hi Jack*, I’m a little jaded from using dating apps so do you want to go for a drink and see if we vibe?

And in the meantime, I was setting up a booty call and a back up just in case. But it was looking like my first option wasn’t going to work so after organising a date with Jack, I then asked if he was free tonight and wanted to come over. And he was keen! So I sent him my usual screener questions that I use on my hook-up app. He passed the test and came over.

He just hard warm friendly vibes and I felt comfortable around him as soon as he was here.

Sex: round 1

Okay, it wasn’t great and I had to ask him to go down on me and guide him loads about what I liked. It was surprising because he had mentioned he got out of a FOUR FUCKING YEAR relationship TWO MONTHS AGO, so I thought he would know what to do down there, but nope.

I asked him to keep going with tongue and fingers until I came, but omg he really needed telling twice or more. Worth it though, so ladies, I urge you to do the same because you deserve orgasms. It was interesting because I usually have sex with men who also have lots of sex so they’re usually better at it. Also I’m glad I did ask him to keep going because he came VERY QUICKLY when we got down to p in v.

Then he asked if he could leave! Wtf?! It was really demoralising. He said he felt weird. I was the first person he had sex with since his ex and he said he just felt strange. I was in a weird needy mood though, because my housemate and her boyfriend were out watching a film and I wanted some company! So I was like, “should I get our wine and we can talk about it?”

Being his therapist

To be fair to Jack, I was the one to offered to talk to him about his issues because he was really really nice and normal and I didn’t want him to leave just yet. I liked that he listened to my hot takes about women and sex. Hopefully he went away realising that women have more agency than he realised and we’re cool with just casual sex. He was previously under the impression that women want to be in relationships and that men are in a difficult position if they just want casual sex. I set him straight by telling him that women just want to fuck too, and men in general should trust us more to know what we want instead of thinking we need to be falsely treated like wifey for life-y for sex. I hope he goes away and tells his straight male friends this.

Turns out he broke up with his girlfriend because she realised that she didn’t want kids, but it was something they had initially agreed on. (Good for her for being brave and standing her ground.) He said it was an amicable break up. I told him it might take him more time to get over her, but that’s okay.

I spoke to him loads about my sex life (it was almost as if I was reading my blog to him), and he seem genuinely interested. I even told him he was option number 3 for sex tonight, and he took it like a champ! But I wasn’t phrasing it as a “hey-I’m-so-hot-I-can-fuck-who-I-want” it was more “yeah-when-you’re-single-organsing-casual-sex-is-a-ballache” kind of description. But seriously, I’ve never slept with someone and then helped them come to terms with their recent break up, and have them listen to my sex-positive views of dating.

He also told me about how he’s sure he doesn’t want a relationship anymore, just casual sex. I told him I’m glad I could help him overcome the physical barrier of being with someone new, but also he should just spend more time learning what he’s like outside of a relationship. Then I was like, “I’m so excited for you, you’ve got all these new things to look forward to now you’re single, you can try all sorts of new things with all these new women.” I did actually mean that sincerely.

Fucking weird.

We both kept feeling guilty

He kept apologising for coming too early and wanting to leave. I said it was fine and he didn’t need to. I apologised and said I felt bad that he wasn’t that into it. I also told him I felt bad because I felt like I had lured him into my place, but he reassured me he wanted this and wanted to come and that he was into me. But no matter how much someone tries to tell you this, you still can’t help take it a little personally when someone you’ve just let into you vagina is like ‘mmmm…’kayyy byeee’. Similarly, even though I said it was okay, he kept apologising to me for not wanting to go again. We both needed to stop but we just kept apologising. So many apologies.

I told him that we need to stop defining sex through male pleasure.

One of the things he kept apologising for was coming so quickly. I told him to stop because I made him go down on me for a fairly long time so I came first, and it was bad that we define sex in terms of male pleasure. Why is it that he thought my enjoyment ended when he came, and that it even started when he penetrated me? I also emphasised to him that it’s stoopid to think of sex that way, because what about lesbians? Do they not have pleasure until a man cums? (LOL)

I got him drunk?

I was also getting drunk on this wine and our conversations moved on to music and morality and house plants. It felt like I was talking to him for an hour but I have no idea how long it really was. But a horrible thought did cross my mind – maybe if I got him drunk he was chill out a little and be up for round 2. I just think if a man thought this about a woman, I was could be PISSED. Am I a hypocrite? I mean he wasn’t slurring his speech so he was sound enough to consent, and he was the one who put his hand on me first. But still, I gave him two large glasses of wine in the hopes he would have sex with me again…

Sex: round 2

Like I said, he put his hands on me first and did want to go again. I asked him a few times just to be sure. But again, he came quickly. Fair enough; like I said, I was his first in four months. It was more intimate this time though because we had spent a lot more time talking to each other and we were enjoying each other’s company.

This is why I’m a bit concerned about my own behaviour though. I asked him maybe three times if he was sure he didn’t want to go for round 3 because I was SUPER up for it. He insisted he was tired, I said “okay of course, I shouldn’t be forcing you” but I should have listened to him the first time!! I just feel like I’m a super fucked-up product of our own society that tells us that men want sex all the time. I also feel bad because I should have known better and not have made him tell me three times. Fuck, I do feel like a dick. I’m glad he was a nice person and was patient with me. I did apologise for asking him again once he already said he was tired.

Leaving

He called his Via Van. I took this time to clarify where we stood. Maybe it was the booze, but I said I would like to see him again, but it’s against the “rules” and its for the best we don’t. He said agreed (damn, I wanted him to fall in love with me) and also asked me to keep him posted on my next STI check, which I agreed to.

He then actually patted my shoulder as he was leaving. HE PATTED MY SHOULDER. He left around 1 am after I (kind of) fucked him twice and he bid farewell like an awkward uncle. Da fuck?! I made a joke out of it and was like “it’s okay I think we’re past that now” and I got my make-out kiss goodbye, but I have to admit, it was fucking hilarious.

Closing thoughts

I am feeling rather guilty that maybe I was pressuring him into having sex. Although I didn’t cross any actual boundaries, it did take me longer than it should to accept his answers of “I’m feeling tired” and stop pursuing anything further because clearly this fucked up view of “men want sex” – which even Jack acknowledged was a misconception he held – has ruined my understanding of male sexuality. I’m going to definitely take some time to think about this more for the future.

Hope he got his cab home okay!

 

 

* He had some other classic white boy name IRL.