Turning over a New Leaf (and Then Quickly Blowing It): Dates 31.1 & 31.2

Okay. Now I know why I’ve been avoiding writing about my dates. Looking at where I left off, a guy I (still) *really* like is first on the list. Also, to truly explain why I like this particular fellow so much, I’m going to have to get a little explicit. But whatever, right? It’s anonymous, and you’ve been warned.

So anyway, I was the one who initiated contact with Date 31. We were both on a certain (very large, quasi-expensive) dating website, and I saw that he had visited my profile. Something about him struck me as extremely familiar-looking, so I clicked on his photo to view his bio. Turned out, he lived in my area, so I messaged him, saying I knew he was too young for me but asking where I knew him from (my cousins? the grocery store? the gym?). He immediately wrote back and we struck up a conversation that transitioned to texting.

Now, Date 31 isn’t that much younger than me–only one year. Because he’s never been married or had kids, though, I kind of dismissed him as being someone I couldn’t take seriously. And as you might recall, I started off the year on a vegan-no sugar-no alcohol-no caffeine-no sex fast. Yeah, I was probably being a little too ambitious, but I was super determined to see it through. I had resolved not to have any more meaningless sex, wanting to save myself for a real relationship. And that first week of the year, I was very chaste!

By January 6, however, I agreed to meet Date 31 in person. He took me out to lunch at a nearby Thai restaurant. Going into the date, I told myself I was going to be good, that this guy was kind of a goofball, and no way, no how was I going to have sex with him. And then he showed up.

Not sure if I’ve mentioned it, but I seem to have a thing for Jewish boys from New York. It’s getting to the point where I suspect I can tell the difference between accents from Queens, Yonkers, the Bronx, Brooklyn, and Long Island. So when Date 31 walked in, reminding me (in a positive way) of the Beastie Boys? I could barely talk I was so nervous and taken with him. And he seemed to like me, as well, since at the end of the date, he asked if he could see me again.

Before I get to the juicy parts, however (i.e., Date 31.2 and beyond), which will tend to highlight how sexually compatible Date 31 and I are, here’s Problem Issue No. 1: Date 31, while never married, has been engaged. Two years ago, at age 39, his 29-year-old fiancee, a gorgeous, blonde fitness enthusiast (no joke–I’ve seen pictures), was killed in an auto accident. Now, I feel super bad for him, because that’s a horrible tragedy no one should have to endure, but as a potential girlfriend, I could see some difficulties inherent in the whole setup. As in, no one would ever be as perfect as this guy’s dead 29-year-old fiancee.

Since her death, he had settled into a friends-with-benefits relationship that lasted a year, but now he was ready (he said) to find a new relationship, anxious to get married, settle down, and have children. Perhaps I should have ended things right then and there with that admission, since I can’t have children (at least not without the help of a surrogate), but I figured it was too early to jump to any rash conclusions. And besides, he was so cute!

It’s been a few months, so I’m foggy on the details of how it happened, but Date 31 immediately started texting me after our lunch date, saying he wanted to see me again. Eventually, I said okay, come over, so he did.

Things started out vanilla enough, but there’s a certain energy that starts combusting when you match someone dominant with someone submissive in the bedroom. It didn’t take long for him to give my ass a playful slap and discover that the harder he did it, the wetter I got. Add to that the hair pulling, the firm grip he placed around my neck, and the bevy of dirty talk he laid on me, and I couldn’t get enough.

And we got along! Both before and after sex, conversation was lots of fun. Basically, the more I got to know Date 31, the more I knew he was a sincerely nice guy. So nice, in fact, that he said he understood if I wanted to still date other people, but that he’d like me to only have sex with him if we were going to see each other again. This puzzled me at first, but then I was like, Okay! Because if I was getting my sexual needs met, I wouldn’t be tempted to jump into the sack with guys I barely knew or knew there was no future with.

After Date 31 left that night, I looked in the mirror and discovered just how enthusiastic a spanker Date 31 was–my ass was covered in splotchy red and purplish bruises. Um, no problem staying away from other guys, I concluded, since I didn’t want anyone to see me that way!!! I knew he was strong (he’s played sports all his life), but I’d never had someone mark me up like that, and I’ve been with some pretty rough folk!

The next day, I got a series of texts from Date 31 that made me think he’s either been in extensive counseling or has an incredible mother who brought him up right. Yeah, it’s kind of dorky to get a text that says something like, Thank you for having sex with me last night. I really appreciated how wet you got for me and how hard you were able to take it. But after all the callous guys I had dated in the last year, Date 31’s little thank-you texts made me smile, my heart becoming increasingly tender toward him.

I knew we were both still dating other people, but I was anxious to see where things between me and Date 31 were going.