Tag Archives: Spanking

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.

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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.