Tag Archives: Anal

Date 4.1: Let’s Talk about Kink

Now, I realize there are different levels of kinkiness. What some consider tame, others think makes them a wild and crazy guy. For example, Date 2, while we were having sex, kept remarking, “You are so submissive!” (Did he do anything about it, however, other than slap my ass a couple times? No, unfortunately, but I hadn’t been planning on going there with it, so the sex was still rockin’.) Date 3, on the other hand, straight out informed me that he was a little kinky. “Put on your shoes,” he ordered before proceeding to fuck me standing up in front of his mirrored closet doors. Eh, whatever. Not my thing, but I could see it–they were an awfully sexy pair of high-heeled sandals.

Maybe I’m a little blasé about the world of kink, but you have to understand, even my high school boyfriend and I (my first real love, when I was 16 and he was only 15–yikes! I know) had somewhat of a D/s relationship. (Side note: at the beginning of my senior year of high school, this bf dumped me, leaving me emotionally devastated. As I found out later–remember how I mentioned those exes coming out of the woodwork on facebook?–he thought he could do better, that every girl was like me, enjoying sex two-plus hours at a time and more than willing to indulge his fantasies. But guess what? No such luck! Because he’s a total player, I find this shocking. Apparently, though, I’m more unique than he figured, leading him to lobby a quasi-proposal of marriage at me. I told him we’d need to meet in person first, to see if the chemistry between us was still there, but on the inside, maybe I’m immature, but I couldn’t help cuing Nelson-from-The-Simpsons’ voice: HA HA!)

Anyway, Date 4 and I had chatted a little by email regarding our mutual interests in the bedroom. We seemed to be hitting it off, so we made plans to meet at Starbucks for coffee. When I showed up, I recognized him from his photos immediately, but he was little older than I expected. Although his online profile listed him as 45, I’d just been out with a 43-year-old (Date 2), a 42-year-old (Date 3), and my ex-husband is currently 45, so I know what that looks like. This guy was definitely older. Hot in his own unique way (I go for geeks, as you might expect, and he was a complete brainiac, as well as fit, so I was totally onboard with his package), I didn’t have any problem with his potentially being older, but something else gave me pause: his lips were blood-flush red. Because I (very unfortunately) have extensive experience with penile dysfunction, my mind immediately flagged the red lips as being a possible side effect of Viagra.

Maybe I’m wrong, and he just had a sunburn (on his lips!) or whatever, but I was flattered. I thought, At least he thinks I’m hot enough to spend a blue pill on me. Those suckers aren’t cheap! So we chose an isolated table and sat down to talk. As it turned out, he wasn’t 45, he was 49 (or at least that was the age he admitted to, since I have a subscription to one of those snooper services, and there’s a guy by his name who owns property in the same areas he does who’s 54).

After we’d gotten through the conversational niceties, discussing our respective kids, divorces, and professional backgrounds, Date 4 matter-of-factly laid out his intentions. I listened in fascination as he casually explained how he’d like to spank me over his knee, eat both my pussy and my ass, then have both regular and anal sex. “We don’t have to do everything right away,” he assured me, “but I’d really like to spank you today. Shall we go to your place?”


Yeah, I’ve done some kinky stuff, and I’m probably naïve, but I’m not used to going there with someone I so recently met! And the ass-eating? What was up with that?!? No way I was kissing him after that business. But still–I was curious, so we indeed went back to my place, and it was fun.

Not sure I’d want that much variety every day, every time, but we definitely clicked, and I’ve seen him again. I just need to make sure I have an opportunity to rest in between.


Date 3.1: Guys with Game, Part II

So I have a confession: I’m kind of a nerd (as if you hadn’t already guessed!). Being the geek girl I am, though, I have this sort of, well, “policy,” for lack of a better way to put it. The deal is, if I’m going to get serious with a guy, he has to be smarter than me. Now, does this mean I haven’t dated guys to whom I knew from the outset I was intellectually superior? No. Definitely not. I just realize things are never going to go anywhere with those particular individuals. However, that doesn’t mean I can’t enjoy myself in the meantime, especially if I can learn something from someone (e.g., about their travels, culture, profession, quirks, and sure–their sexual proclivities, if we end up going there).

Anyway, with all that in mind, I knew right away that Date 3 was a terminal case. What I could ascertain from his online profile was quickly confirmed when he insisted on calling me to make small talk before we embarked upon a real-life date. Conversation-wise, I have to say, it was somewhat of a struggle to stay awake.

So why, exactly, did I agree to go out with this guy, if my standards are so cerebrally driven and lofty? Glad you asked! Did I mention that Date 3 was a scorching-hot South American dude who turned out to be from a wealthy, half-Spanish/half-Italian family? Um, yeah. As in, yum!!! As in, the second he hit me up by email, I knew I had to tap that.

Don’t let anyone convince you that all women ever want is security and cuddling. Because sometimes, a good pounding in the bedroom fits the bill oh-so-much better. And if a swarthy-looking South American from an aristocratic family is available to do the job? So much the better!

So, yeah–I met him for drinks at a wine bar near his place. He didn’t live too far away from me, meaning the location turned out to be pretty convenient. Not heeding my own advice about skipping meals and going straight to drinks, however, once again, I got my lightweight self good and schnockered, so he drove me back to his condo with the promise of returning me to my car later in the evening.

Still suspicious that Date 2 might have been married, it was a relief to be taken home to Date 3’s nice little one-bedroom/one-bath bachelor pad. Interesting, too, since I got to see what type of decor he favored, as well as ascertain his financial acumen, based on his choices in furniture and electronics.

Not bad, I thought, wondering how much he paid for his place, trying (without success, I might add) to remember the address, so I could look it up online later. And he wasn’t a slob, I noticed. After being with someone for twenty-three years who couldn’t see fit to put his laundry in the hamper, let alone use a coaster (even if ignoring said usage caused irreparable damage to antiques that came to us from *his* family), the fact that this guy was meticulous enough to still be wearing his retainers (saw them on the bathroom sink–ha!) was more than a little refreshing.

And then there was that gorgeous face. That soft, wavy hair. That amazing surf-and-cardio-chiseled body. Needless to say, my tour of his place ended in the bedroom. And he didn’t disappoint.

Not sure how many condoms he went through, but we eventually had to stop after a couple hours when he got too hungry to keep going. Now, Date 3 was a skilled lover, to be sure, but here’s what I didn’t like about him: he took me anally without permission. Because he knew what he was doing, it didn’t hurt me, but I was still like, Hey! Not cool!!! Especially since I told him not to go there when he first tried.

Anyway, even if he hadn’t been such a sweetheart when I got all maudlin during our post-sex pillow talk, as we discussed our respective families and I lamented how much I missed my mother-in-law (to the point of my being in tears, because I miss her terribly–she was a better mother to me than my own parents), the anal invasion was a deal-breaker. No way would I ever agree to seeing this guy again, since I obviously couldn’t trust him.

Not that he’s called or anything.

But you know what? Despite knowing he was headed to South America the following week, I didn’t tell him about the raging sore throat I had at the time, either, which ultimately wound up requiring antibiotics.

Hope it didn’t mess up his trip too badly.