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I reluctantly agreed to a phone call last night with that 20-something dude I met once in fall of 2014. I shouldn’t have. Hell, I shouldn’t have even responded to his Facebook message in the first place. I regret it.

I was a completely different person then.

In fall of 2014, I was newly separated and finally free from the tethers of a sexless marriage. To put it lightly, I was on a sexual fulfillment rampage. I met this dude on OK Cupid; he agreed to drive up from the peninsula to my office for a quick sexual encounter. It was the only time I’ve ever done such a thing and I’m not proud of it.

He texted me when he arrived into Oakland and I met him outside my office building. I hopped into his car when he pulled up. He was a cute 26 year old attorney but was immature and nervous. We drove to a parking garage. He parked on the top floor where there were fewer cars. I gave him a blowjob while Depeche Mode’s Violator album played on the car stereo.

Afterward, he drove me back to my office building and we chatted for a few minutes before saying goodbye.

He reached out a few times after that but I mostly ignored the texts due to his immaturity, i.e. he went on and on about how hot our encounter was. Enough already! Move on from it, dude.

When he reached out recently on Facebook, I asked him why he was contacting me over 2 years later. He said he wanted to chat, catch up, and have some closure.

I shouldn’t have agreed to it. He tortured me with ridiculously immature texts beforehand.


Him: Can I ask you a question?

Me: For fuck’s sake. What?

After I answered that, he kept going.

Him: Can I ask you another question?

Me: WTF. Just ask already! You don’t have to ask to ask a question. Jesus.

I didn’t have time for this. So I reluctantly scheduled the phone call just to get it all over with. I told him I only had a few minutes last night; he balked. Dude. Why the fuck do you need more than 15 minutes of my time?

Before he called, he bombarded me with texts again. He said he was excited and deliberately left work early so he could talk in peace at home. That was a red flag.

He called at 6. We had some basic catch up chit-chat, then he wanted to talk about our meeting over 2 years ago. He told me it was the sexual highlight of his life and he’s been trying to match it ever since. He also said that for about a year afterward, he deliberately only sought out older women. He shared some of his experiences with me. I was not amused because, frankly, I didn’t care.

He asked me a lot of questions, including:

Is that the craziest thing you’ve ever done? Yes.

Would you have had sex with me? Yes.

Do you still think about it? No.

Would you do it again? Hell no.

Did you tell your friends? Hell no.

If I still lived in San Francisco, would you let me come over to your house right now for a repeat? Hell no.

What did you think of my cock? *I was overly annoyed at this point* Are you serious? Your cock is fine.

He pushed for details… asking if I was pleased with its size and if it was one of the largest I’d ever seen. Are you fucking kidding me. I snapped, “Look Jay, I’m not going to stroke your ego. Your cock is average, okay? I don’t know why you’re asking me this.”

I ended the call quickly after that. I’d already given him more time that I’d agreed to.

I was agitated and unsettled by our conversation. His number is now blocked.

I didn’t hear back from the repeat canceler last night so I gave his allocated time slot to someone else. I have a date tonight and a date tomorrow night. Both are named Matt.

Stay tuned.