Tag Archives: Sexuality

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.

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.

Dates 0.1 and 1.1: Places I Shouldn’t Have Gone

You shouldn’t have sex before marriage. You know that, right? I tell my kids this, and, increasingly, I tell myself the same damned thing (for all the good it does me). But why not? the kids inevitably ask. Doesn’t everybody live together before they get married?

That’s beside the point, I generally say, not wanting to cop to the fact that their father and I did, indeed, live together for almost three years before marrying. The point is, I attempt to patiently explain, sex will attach you to someone you may not end up wanting to be attached to, making it harder to leave them, even when you realize they’re not right–or even downright bad–for you.

So there it is, my lecture on abstinence. Unfortunately, I’m not very good at taking my own advice, even when I know it’s right. But that brings me to the subject of Date 0.1.

Date 0.1 (I’ll let you decipher my numbering system as we go, but really, it’s pretty simple) was what I now like to think of as a practice date. One of the aforementioned choice exes who wheedled his way out of the woodwork (admittedly, with some help from yours truly), Date 0 was a guy I’d been in love with for years. He’s a fellow writer (also legit, of the ilk that speaks at Comic Con) I’d known before my ex-husband. Anyway, not going to say anymore about that except that, while married, we never cheated on our spouses with each other (even though they both believed otherwise). We did carry on by email for awhile, however, roundabout a decade ago, until the whole thing blew up and we went our separate ways, since he was ultimately just as stubborn as I was about making a failing marriage work. Afterward, we went without any contact whatsoever for years. That is, until I left my marriage.

So…I have to say–that friendship with the college ex? It got me through some hard, dark times. It also put me through some even harder, darker times, but whatever. With him living over a hundred miles away, our “relationship” seemed a safe space and, really, a moot point. But the question eventually emerged: Do we still have anything in person together or not?

Eventually, the day came to find out.

Without giving away too many telling details, we made plans for him to stop by my place for a brief visit on his way to somewhere else. And he did. While at my place (keep in mind I hadn’t been with anyone since my ex-husband at this point, and my ex had a problem with impotence he blamed on me, leading to our having sex only three times during the last five years of our marriage), all we did was talk. The college ex looked great, as I had suspected from the pictures I’d seen of him, and I was just as attracted to him at age 42 as I was back when we were both 18-year-olds (and 30-year-olds, for that matter). So I sat there, lusting after him, studying his hands and forearms (did I mention I have a thing for piano players?), wanting to climb onto his lap and get busy.

But I didn’t. Instead, I minded my manners and sat across the room from him, painfully aware that he was now married to Wife No. 2. After a couple hours of chit-chat, he left. Here’s the kicker, though–he left without so much as giving me a hug!!! Talked nonstop, couldn’t even look me in the eye without seeming sheepish or guilty, yet he didn’t even use the socially acceptable touch-excuse of a hug to determine whether we still had that mind-blowing sizzle between us??? I was floored.

In subsequent email communication, when I asked why he didn’t even hug me goodbye, he told me he didn’t get a “physical vibe” from me, and he’s not much of a hugger. Sorry, but I call BULLSHIT on that! Guy gave me one of the best hugs of my life back when we were 30, so no way I was buying that excuse. But whatever. Obviously, it wasn’t happening between us. Problem was, I worried maybe my ex-husband was right–maybe it was my fault that he didn’t want to have sex. Maybe I just wasn’t sexually attractive to anyone anymore, so I should just give it up and become a cat-lady spinster. At least I’d already had kids, so it’d be easier to forget about romantic love and just increasingly center my life around my offsprings’ upbringing.

Instead, though, on my 24-year-old half-brother’s advice, I joined a dating website. To my little bro’s horror, however, I immediately got hit up by a bevy of seemingly eligible guys, one of whom was only 25.

Yes, I knew it was wrong. That even if things worked out between us, I’d be using him at best. But there are worse ways to be taken advantage of, right? And he seemed down with it, actively encouraging me to go there with him. Quickly, our website communication led to texting (which can get out of control with these younger guys, but I’ll touch on that in another post), then some actual phone conversations.

In my defense, he had a great sense of humor, and our sexual propensities had some key overlap I was eager to explore. Plus he looked cute in his pictures. So I agreed to meet him, leading to Date 1.1.

Now, even if you totally ignored what I had to say above about how you shouldn’t have sex before marriage, don’t ignore this: Meeting someone you’ve never met before around midnight in an empty mall parking lot is not a good idea.

Duh! you’re probably saying, and that’s a beautiful thing. I’m glad you’re wiser about these sorts of issues than I was. But I was horny, and he was 25, so I went for it. And it turned out badly.

Luckily, I didn’t get attacked or date-raped, but things weren’t exactly smooth sailing, either. First off, he showed up wearing a ratty old concert t-shirt and saggy jeans. Second, he was more overweight than his pictures led me to believe. Third, he had a total baby face–because, do you realize how young 25 actually looks when you’re 42??? Trust me–it’s not good. Made me feel like I belonged in jail, not his arms, which were too pudgy anyway.

So I got out of there as fast as I could. Playing the age card, I told him he reminded me too much of my son (even though he didn’t, as my son is way thinner and more mature looking). That didn’t stop the guy–this stranger I never should have agreed to meet so late at night–from planting a juicy kiss on me and running his meaty hands up my skirt. He grabbed my hand and put it on his junk, too, which turned out to be quite sizable.

But that was where it ended. To his credit, when I said no, this wasn’t going to work for me, he left my car and drove away in his truck. Didn’t stop him from continuing to text me weeks later, but he eventually gave up since I wasn’t responding.

So, yeah–Date 1.1 was probably a HUGE mistake in many different dangerous ways. But it taught me something: Even if my ex-husband and my ex-college guy didn’t find me attractive or sexually alluring, someone else did. I was still sexy, and I still had it. And if a guy 17 years younger than me thought so, there had to be others who shared his opinion.

Now I just needed to find some more appropriate candidates from whom to receive that sort of attention.