From theory to practice with Leo.

Leo and I booked a date after our big talk. A full-on dinner and activity weekend date. I was cautiously optimistic.

It was going to be a beautiful day so at the last minute we modified our plans. He came to my house just after lunch and we planned to do a day trip to a nearby wine region, visit some of the quaint towns in the area, and have dinner. If anything was going to be an issue, it wasn’t going to be our itinerary!

I asked if we could take my car, as she sorely needed her legs stretched, and it’s more comfortable than his van. But I asked if he would drive home since I wanted the freedom to have a couple of glasses of wine if desired (he’s not a big drinker) and I don’t love driving at night.

He agreed.

We stopped for wine and whiskey tastings. We laughed at each other’s jokes. We kissed spontaneously and passionately in the street. 

It was fun. I was having a good time. And while the restaurant would not have been my choice, I’m no petulant diva. It was just fine. He paid. 

All in all, it was a great time. We didn’t talk endlessly about the new information we’d shared, but we did clarify a few things. 

I asked him about what was still bothering me. The first was how he was able to make the transition from casual to meeting me, and whether he was having sex with others after he met me. He explained about six months prior he’d gotten tired of the casual sex with rotating partners (after six years!) and had really slowed down his engagements with others.

He reiterated he’d been honest when he said he wasn’t seeing anyone else on our third date. He said his number was lower than I probably thought: around 250. I told him I didn’t care either way.

We talked a bit about his ED and what he and his Doctor thought contributed to it – a combination of weight gain (the biggest factor) and his mental worries about sex. 

I continued to be satisfied that he was telling me the truth, not just what he thought I wanted to hear.

I was very curious what it would be like once we got back to my house. 

The outcome? For perhaps the first time, I am genuinely excited for what could perhaps happen with Leo. How’s that for caveats?

He was more verbal. He talked to me during sex, told me dirty things, and encouraged me at just the right time (“that’s it, baby. Cum for me, Ann.” Despite some ED issues, we tried different positions. 

It was much closer to what I’d been hoping for this whole time. He woke me up in the middle of the night for sex. He’d wake up and wrap his arm around me. We lay in bed the next morning and he made me cum some more. I insisted on doggy style, and it worked for a few minutes. We laughed and talked and cuddled and kissed.

I asked him whether he’d used condoms when he was on his great casual sex mission. He said no. We talked about how dumb men (and women too, I suppose) are when it comes to such things. He reminded me that shortly after we met, he’d been tested for everything, as he underwent a medical donation procedure which required it.

I told him if he was to have sex with anyone else I expected him to use a condom. He chuckled and said “Ann, I’m not going to have sex with anyone else. I’m not interested in anyone else. And anyway, I’m not going to do anything which risks me losing my unicorn 🦄 .”

I have hope. Still tempered with a lot of hesitation, but it’s there. 

It’s a really nice feeling.

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