Dates 4.2 & 4.3: Hanging with the Anal-Sex Fan Club

I know it’s been awhile since I wrote in chronological order, but I think I was kind of waiting to see how things resolved with Date 4 before detailing the stuff that’s happened between us. Anyway, a few months have passed, so now the time feels right.

That said, considerable time has passed since I last mentioned him. In case you’ve (understandably) forgotten who Date 4 was, he’s the guy who’s super into anal sex, rimming, and spanking me. He’s also kind of a nerdy science guy who I totally get along with on an interpersonal level. Beyond that, he runs marathons, climbs mountains, and takes long hikes and such, so he’s super fit, meaning he doesn’t tire easily in the bedroom. Yes, he’s also blind enough that he keeps his glasses on while having sex, and he occasionally forgets to take off his socks before we get busy, but whatever–I actually think we’re pretty compatible.

Both Dates 4.2 and 4.3 were at my apartment. Because Date 4 and his ex-wife do the “nesting” thing, where their kids always stay in the house and the parent who’s not on duty sleeps elsewhere, he made it clear to me from the beginning that we would never be meeting at his place. That was fine, I assured him, since his coming to me meant less driving on my part and, quite frankly, sheer convenience. However, later on in our dealings with each other, I stopped feeling the convenient aspect of our dates, as I’ll relate below. Anyway, here’s a quick blow-by-blow of our history with each other:

Date 4.2 – On his way to the airport for a business trip, Date 4 makes plans for a quick lunch date with me that we both know isn’t going to involve either of us eating any actual food. With only two hours to spare, we don’t waste any time getting with the program. I go down on him, he goes down on me (front and back), he spanks me (both with his hand and with the belt, leaving marks that last a week), he fingers me (again, front and back), and we have both anal and regular sex. Along the way, we both climax, leaving us two very happy campers. I send him on his way afterward, and off he goes on his business trip.

Date 4.3 – Once again, we make plans to meet for “lunch” at my place. While not quite as frantically paced as our last date, we again have marathon anal sex that leaves me wondering what kind of damage I’m doing to my body. And speaking of damage, because my back had been acting up that week and Date 4 has bragged about being formally trained in massage, after we’re done having sex, I ask him for one. He obliges but seems kind of stingy about it. I’m thinking, Hey, dude–it’s not like I’m asking for much here. How many other 40-something chicks you know who’ll let you ride them anal for over 30 minutes a pop? As he’s leaving, I tell him I’d like to actually go out to lunch with him next time, so our relationship isn’t only about sex. He agrees and promises to take me out on a “real date” next time.

About a month later, Date 4 texts me, asking if I can FaceTime with him, so I do. While talking, we make plans for him to take me out the following day. The next day, however, he never texts, calls, or emails. I text him but receive no response. Because Date 4 had been pretty good about keeping promises to call, text, and see me up to this point, I was kind of worried about him. Did his son have to go to the emergency room? Did one of his parents die? Was there some sort of work emergency that necessitated his flying back to the home office on the East Coast ASAP? But he never told me what happened.

A couple weeks later, he finally texted me again, asking if we could hook up. My reply was terse. I told him how my time is valuable, so if he’s going to make a date with me, I’d appreciate his keeping it or, alternately, letting me know if he needs to break it. Message received loud and clear, he wrote back, not saying anything else.

I kind of wanted to tell him I wasn’t trying to put an end to things, just letting him know how his blowing me off had made me feel, but I didn’t. Instead, I just let it go. Because really, sex with him is a tad much. My sheets get all messed up, I have the runs the next couple days, and there’s no way I can picture being with someone long-term who insists on that much anal. I really, truly liked Date 4, though, so I was left somewhat at a loss by the way things ended between us.

The other day, however, I was trolling my favorite dating website and a new profile with a very familiar face came up. I clicked on it, knowing Date 4 would see I’d checked him out and kind of curious what he’d say about it. Sure enough, he messaged me on the site. Hey, gorgeous! he started off, saying some benign stuff about summer vacation and that he hoped I was well.

Softie that I am, I wrote back, wishing him well in return. At this point, he knows what I want–to be taken out for real, not just taken, period, at home in the bedroom–so if he cares to ask me out and start things over from scratch, I’d be open to the possibility. If that’s too much trouble, all I can say is, Good riddance.

4 thoughts on “Dates 4.2 & 4.3: Hanging with the Anal-Sex Fan Club

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