Tag Archives: BDSM

Context: Dates 31.6-8, 35.1-2, and 14.4

Before I get to telling you about Date 37, who deserves a solo entry, just a quick update on where I was at in the dating arena. As you might recall, Date 31 was the sadistic nice Jewish boy who loves country music (and the way I give head). He would be so appalled if he knew I was writing this! Hehe. Anyway, he and I fall into the friends-with-benefits category since we love having sex but know we’re not right for each other based on where each of us is in life (i.e., he wants kids/I *don’t* want any more kids).That said, like me and Date 5 (whom you might recall has porn-star-worthy anatomy), Date 31 and I have an understanding that if we find someone we think is a serious contender, the benefits part of our friendship will be put on hold (hopefully indefinitely, but, you know…this isn’t our first rodeo).

Anyway, here’s the sequence of my dates just prior to meeting Date 37:

Date 31.6–He comes over to my place in his work clothes because he has client meetings afterward. All I can say is, yum! I love seeing a hot man (especially one I know is going to give it to me and hard) in a suit. Have I mentioned that Date 31 is a financial adviser? Well, he is. He works for a nationally known investment-banking conglomerate, so we always chat about the market and such. So there we are, on the clock, at my place. He’s hot, I’m hot for him, and he spanks the living daylights out of me until my ass is various shades of black, blue, and red. Which means I’m out of commission for at least a week with anyone else if I don’t want them to know what a slutty freak I am.

Date 35.1–Coffee date with a guy I met online. Even though I’d sworn off dating Hispanic men, since my many friends who are married to them consistently deal with all sorts of jealousy and possessiveness issues, Date 35 was super hot, over six feet tall, already had kids (boys–which are my theoretical stepkids of choice), and worked in lucrative field (yet another guy from the profession that must not be named, actually), so I made an exception. After meeting him in person, however, I was on the fence. I detected an angry undertone to Date 35’s words–especially regarding his ex-wife–but he was definitely hot and I couldn’t help wondering how the sex would be with him. Being that I was still all bruised up from Date 31.6, though, I knew I’d have to take things slow with this guy if they were going to go there, giving my ass time to look innocent. But what do I do? Instead of taking my vitamins and laying low, the next day…

Date 31.7–On my way to meet a romance-writer friend (of the sweet, chaste variety–yes, there is such a thing!) to attend a literary event, there was just enough time to meet Date 31 for a quickie. Right beforehand, he sent me this text: I’ll leave the door unlocked. Please lock it behind you. I’ll be naked in bed waiting when you arrive at 4:45. Please don’t say a word. Simply take off your clothes and start sucking my dick. After sucking it GOOD for a little while, ask me nicely if I am ready to fuck you. If I say yes, just turn over in the doggie-style position and wait for me to whip and fuck you. See you soon!

Oy. What can I say? I think Date 31 liked the idea of resetting my clock on getting close to anyone else. But that didn’t stop me from going out on a second date with Date 35, since I figured I’d be waiting until at least the third date with him anyway, but…

Date 35.2–When Date 35 showed up in his luxury SUV at my place to pick me up to go out for a sushi dinner, I was wearing a skirt, high-heeled sandals, a dressy top, and a very pretty cardigan (no, guys aren’t that far off base when they say I’ve got a “librarian thing” going on). Date 35, however, was wearing nylon gym shorts, shower shoes, and a grungy T-shirt. I almost didn’t get in the car. “Oh, sorry!” he exclaimed upon seeing me all dolled up. “I should have told you–because I have to wear a suit all week for work, I don’t dress up on weekends. At all.” No shit, I wanted to say, since he’d looked really nice when we’d met for coffee. “Want to go up and change?” he asked. I hesitated, wondering if I should just call the whole thing off, but honestly, I hadn’t had sushi in a long time, and I was super craving it. “Sure,” I said. “I’ll just be five minutes.”

Mistake!!! To make a long story short, the sushi was great, but the conversation was questionable. Date 35’s deep-seated anger became more and more apparent as the night wore on, but at the same time, he kept ordering drinks for us and touching me in ways that were turning me on, despite my better judgment. After dinner, he said he needed to sit in the car for awhile before he felt like he could drive responsibly. Now, the right thing to do would have been to tell him to walk me home, since the sushi restaurant was reasonably close to my place. Instead, I said okay and hung out with him in his car, where he proceeded to maul me like a sex-starved teenager. No, I didn’t have sex with him, but he got way too up close and personal with my business. Luckily, it was dark, though, so he didn’t see why I was fighting so hard not to remove my clothes. In the days afterward, he texted me incessantly, wanting to take me out again. Because of his angry attitude, I hesitated to say no right away, kind of giving him the run around, but within a week, I manned up and told him sorry, I just wasn’t feeling it, and he left me alone.

Date 31.8–Knowing I was about to have oral surgery and my dick-sucking prowess would be impaired for at least a few weeks, Date 31 made a special late-night visit to my place mere hours before I was slated to show up at the periodontist’s office. It was the third time I had seen him in ten days, and I have to say, even though we were clear on not being serious with each other, it felt way too comfortable, like if we did ever decide to take things to the next level, we’d actually be pretty happy together. We talked about pre-nups, my kids, the stock market, after-hours trading, and whatnot. He ate my leftover Chinese food, then devoured a bunch of my homemade oatmeal-craisin cookies, exclaiming how fat he’d be if we were married. But what can I say? Different goals. At any rate, we parted on a good note.

Date 14.4–Have I mentioned that I’m a sucker for men in golf clothes? Not sure what it is, but I can’t help it–I get totally wet when I see hot guys in polo shirts, visors, and golf shorts or pants. Date 14, who was still 27 at the time, works for a major golf-equipment manufacturer and golfs a lot as part of his job. I was probably way too loopy from the painkillers I was on after my surgery, but for whatever reason, when he texted asking if he could stop by for a little while, I said okay, sure. When he showed up still wearing his golf clothes, however, I was like, right on!!!

What a mess. So, all that to say, I’m somewhat lacking in the self-control department. Both Date 31 and Date 5 had been telling me forever that if I liked a guy, I needed to NOT sleep with him right away, instead making him wait a bit. With that bit of wisdom in my pocket and my recent experiences–which proved I was going nowhere fast in the relationship department with how I was behaving–a couple days later, I went on a first date with a new guy: Date 37.

Advertisements

Dates 31.3-31.5: The Sweet Spot

From the beginning, it was pretty clear that Date 31 and I had it bad for each other in terms of sex. Starting with Date 31.3, however, I realized it was more than that, which was a problem. Basically, Date 31 wants to have kids, while I don’t. He also wants someone ten years younger than him, but I’m two years older than he is. Add to these two dealbreakers the fact that I’ll never be as perfect as his dead 29-year-old former fiancee and that I have both an ex-husband and three kids from my prior marriage, while Date 31 wants a girl with a clean slate, and you can imagine how my being so taken with him is more of a liability than an asset.

ANYWAY, Date 31.3 was the first time I went over to Date 31’s place. Granted, his best friend from Long Island was about to arrive from the airport, so I’m sure Date 31 had worked hard to clean up, but here were the first things I noticed: (1) a shoe rack by the front door, meaning he cares about keeping his place tidy; (2) real (as opposed to particle-board) furniture, showing me he either appreciates living amongst comfort and beauty or his dead fiancee had great taste and he still has the same stuff; and (3) a mix of tasteful (again, dead GF’s picks?) and comics-oriented kitschy artwork (most likely his), showing me that he truly does have a golly-gee sense of humor that’s surprisingly squeaky clean, despite his mad sadistic streak and penchant for dirty talk in the bedroom.

The other thing I couldn’t help noticing was that his apartment was directly above the complex’s pool. It was an unseasonably warm afternoon (Santa Ana condition, making it in the 80s in January), and Date 31 lives in the same suburb as I do (which is known for its schools), so it sounded like there were about forty kids in the pool, all screaming and splashing and generally having a great time. I complimented Date 31 on his place as he showed me around, noting how nice the floor plan was and such. He thanked me, then said (in total seriousness), “Yeah, the other thing I love about this place is how quiet it is.”

I started laughing. “Really?” I asked.

“It’s like there’s never anyone around,” he said. “Always so quiet.”

I pointed toward the balcony overlooking the pool. “You don’t hear that?”

A chorus of shouting pre-pubescent voices wafted upward: “Marco!” “Polo!” “Mom! Jaden’s splashing me!” Etc.

He shrugged.

“Seems like there might be a lot of kids in this complex,” I said.

Date 31 laughed, conceding I had a point. “That’s funny,” he said. “I never really noticed.”

I could tell he was being honest–he truly hadn’t noticed. Basically, I chalked up his acceptance of kid noise to the fact that he wanted kids of his own so badly, which made me doubly nervous. Because what if I got super attached to him? What if he talked me into giving a shot, having one for the road. Even though I’ve had a hysterectomy, I have eggs. Lots of couples in their forties are using surrogates these days, so it wasn’t like it was beyond the realm of possibility–but it wasn’t a future I envisioned for myself when I left my ex-husband.

Before we headed to the bedroom, the last stop on my tour of his place was the kitchen, where there were five piles of goodies laid out on the counter, with a nice variety of all the junk-food groups represented: salty, sweet, gooey, greasy, and crunchy.

“I bought snacks for the game for each of my buddies,” he explained.

I know it may sound silly, but I was almost moved to tears. Because, what a sweet guy!!! From his thank-you texts, I had suspected he was a considerate man, but now I had proof.

[Side note: Have I mentioned The Five Love Languages, by Gary Chapman? If not, it’s a book that describes how each of us has a way we most often express love and enjoy having love expressed back to us. The five “languages” are Physical Touch, Gift Giving, Quality Time, Acts of Service, and Words of Affirmation. All these are great, but the one that really gets my heart racing is Acts of Service. Like, want to *really* impress me? Wash my car, or fix the little piece that fell off the valance to the living-room blinds. Load the dishwasher, or bring in the trash cans (without being asked!). Diamonds, flowers, and massages are awesome, but it’s these little day-to-day efforts that truly make me feel loved and cared for.]

All that said, I knew I had found an amazing guy. Was he perfect? No. Over the course of Dates 31.3, 31.4, and 31.5, I learned that he enjoys country music–the pop kind–because “it’s just so happy.” Also, the TV in Date 31’s bedroom is taller than I am (and I’m 5’6″). Yeah, I’m sure it’s cool to watch movies on, but he likes to leave it going (with the volume silenced) while we’re having sex. Not to rain on anyone’s parade, but the flashing lights from having a TV on are kind of distracting. Also, isn’t that kind of a waste of electricity? If the sex hadn’t been so consistently stellar, I’d suspect him of watching TV while we were going at it, but he wasn’t, so I was left wondering, Why???

No matter, though–I was hooked. I couldn’t get enough of Date 31, and he seemed to be pretty taken with me, as well. We texted each other on a daily basis, constantly on the lookout for opportunities to steal a few moments from our respective busy schedules to spend together. Our first five dates spanned eleven days, if that gives you an idea of how caught up in each other we were.

And the sex? Good Lord!!! Date 31 loved to do all the nasty things I fantasize about but am too shy to voice. He used his belt, I used my mouth, and the things he said to me? Makes me blush just to think about it! So incredible, I found myself thinking, Yeah, I’d have another kid (and enjoy raising him/her) if it meant making this guy happy!

Which was right about when I realized, Oh, shit. Right after I almost blurted the words I love you.

In a last-ditch attempt at self-preservation, I didn’t tell Date 31 about my near slip-up in person, but I did admit to it via text a couple days later. The result? We didn’t see each other again for a week and a half. Could have been longer, but I’ll get to that in a later post. At any rate, the damage was done: I was supposed to be playing it casually, but I liked Date 31 too much to lie to him about the nature of my feelings. For better or worse, I knew I had to tell him the truth–even if it wound up costing me.

 

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.

Viewing Myself through the Lens of Date [-4]: Domme Potential?

Although I mentioned Date [-4] briefly in my last post, I was kind of pissy about it, since I highly suspect “he” was actually Date [-1/-3], and not a new person. That said, I didn’t want to give him/her the satisfaction of my detailing their dishonesty, lamenting over why they wouldn’t just meet me in person and get it over with already. But here’s the thing: in this incarnation of his/her online dating persona, s/he pretended to be a submissive guy who wanted me to take charge and basically show him the ropes.

Interesting dilemma, that. As a deeply submissive woman, I know what kind of charge we subbies crave. Out of curiosity’s sake, while planning for our “date,” I tried on several outfits, trying to cultivate a stern yet sexy look that I suspected would make Date [-4] cream in his shorts. Taking it a step further, wondering if he really, truly wanted me go there with him, I got out my flogger and waved it around threateningly while making nasty demands. All the while, I watched myself in the mirror to see if I could really pull off being so authoritative in the bedroom.

Oddly enough, I got rather turned on by the whole process. Imagining myself whipping his bare, pinky-white ass, leaving angry red marks from the thin strips of pliable leather, I felt somewhat empowered. Could I really do this? I wondered. Should I start dating submissive guys?

I’ve heard plenty of stories about this particular breed of men. How they’re usually high-powered executives. How they’ll pay $500 an hour to have a hot chick stomp all over them in stiletto heels. Joking around with my sister, I asked her what she thought the practical applications of dating such a guy could be like.

“You will buy me dinner,” I said in a bossy tone of voice.

“We’re going out of town for the weekend,” I continued, “and you’re going to book the reservations.”

“I need diamond earrings. Now!” she barked, and we both dissolved into laughter.

Joking aside, I have to ruminate over whether that submissive side would bleed into other aspects of a romantic relationship. Would the dominant person always be responsible for planning dates? Would she have to pay the bills (albeit out of his checking account!)? Would she always have to initiate sex? Does submissiveness in a guy translate to laziness?

Maybe, maybe not. I’m submissive, but I’m a total go-getter in terms of achievement. At work, I’ve always been an exemplary employee, taking charge when the job requires it and deferring to orders as needed.

Anyway, we’ll see. There’s a younger, somewhat submissive (real) guy I’ve been messaging with on the dating site for awhile now, and I think we might finally go out. True to stereotype, he’s a financier who probably has an MBA or something. Way too many years between us for me to take him seriously, but I have to say this: when we finally go out, I hope it’ll be on a cool night, so I can wear my boots.

Dates 12 and [-4]: The Telephone Is Your Friend

Last night, even though I shut my dating-website profile down (again), I received a call from a guy I’d briefly traded messages with a couple weeks ago. I felt kind of bad about not remembering him better (“What’s your name again?” “How old are you?” “Oh, yeah–the straight-edge/agnostic/vegan guy with the one-hit-wonder-’80s-band screen name. Now I remember you!”), but we had a nice conversation anyway.

Although I kind of doubt we’re ever going to embark upon an actual date, we had an interesting discussion regarding the peculiarities associated with online dating. When I related to him how I’d been stood up on a coffee date this week by Date [-4] (who, in hindsight, I’m strongly suspecting is actually that same lesbian chick who played me twice before), he asked, “Didn’t you talk by phone first?”

“Um, no,” I was ashamed to admit. But then, about half of the dates I’ve gone on haven’t involved phone conversations beforehand, just an exchange of email and/or text messages. Not to mention I have talked to certain guys beforehand, but then meeting them in person was a total bomb (see Date 1.1). Some guys just aren’t as comfortable chatting by phone, so the fact that Dates 2, 4, 5, 7, 8, 9, 10, 11, 12, 15, 18, 21, and I didn’t converse telephonically before our respective first dates didn’t strike me as odd. Now, however, I’m starting to learn.

Better late than never.

Because, let’s pick apart the above situations…

Date 2 – If I’d insisted on his calling, he’d have declined, because I’m pretty certain (after the fact) that he’s married, so sharing his cell phone number (because I’m also pretty sure he’s an amateur, part-time cheater, not a guy with a secret disposable cell phone for extramarital escapades) would have been a no-go. Now that I’ve moved back to my previous suburb (where Date 2 also happens to live), I’m just waiting for my opportunity to make him sweat. One of these days, we’re going to run into each other at a school or social event. I won’t rat him out, but I will say something like, “You look familiar. Where have we met? I can’t quite place it…”

Date 4 – Extremely resourceful and horny, if I’d insisted on a phone call, Date 4 would have made it happen, so maybe he’s not the best example of why this should become a nonnegotiable dating policy. Plus, he called and face-timed me after we were already dating, so even though he wound up being kind of a flake, I really don’t think he has anything to hide. Then again, maybe he’s still married, too, and not in the process of getting a divorce, like he said. Never can tell, especially when someone just up and disappears.

Date 5 – Just in case he happens to be reading (since he’s one of the two guys who know about this blog), I’ve got a message for him: I love you, babe, but you’ve got intimacy issues. Had I insisted on a pre-initial-date phone call, I might have been able to sniff out this fact. Maybe it’s just me Date 5 doesn’t want to get close to, but his hardcore avoidance of real-time phone conversation makes me wonder what’s going on beneath the surface. Could be why a great guy like him is in his late 30s and has never been married. Just saying.

Date 7 – If I bored (or overwhelmed?) him so much he didn’t want to go out with me again, and all we did was have drinks, appetizers, and conversation together on our first date, perhaps we could have scheduled a phone call beforehand and skipped a step? Again, just saying–everyone’s time is precious.

Date 8 – Guy was legit, so a pre-dating phone call wouldn’t have changed anything. However…he was late to our first date, and we’d only been communicating by email prior (and I didn’t yet have a smart phone), so it would have been nice if he’d called to let me know he was caught in traffic but on his way.

Dates 9, 10, & 11 – They probably would have called if I’d insisted, and then I’d be more clued in about their personalities and priorities. Not a dealbreaker, since I’m usually up for meeting new and unique people, but also not a bad thing when you’re agreeing to meet a stranger off the Internet for the first time.

Dates 12, 15, & 18 – Could have saved myself some trouble if I’d talked with these guys beforehand. Dates 15 (communication-scrambling accent/rotten tooth) and 18 (sex maniac/control freak), you know about. Date 12, I’ll get to in a minute.

Date 21 – Not sure a phone call would have changed the outcome, but at least I’d have been forewarned about how passive he wound up being, which didn’t ultimately wind up giving me what I was looking for that night.

If I had engaged in a longer telephone conversation with Date 6 (he kept catching me as I was running out the door, so we never got to talk much before meeting in person, though I have to give him credit for trying), I would have known that (like the guy I chatted with last night), he laughs like Scooby-Doo. I also would have gleaned how freakin’ boring his life was (like another random guy I’ve met online, talked with on the phone, but have no plans to ever meet in person), so I might have nixed our plans and saved him a drive from East County.

But let’s get to Date 12 already, shall we?

All right. This is going to make me sound like kind of a mean person, but I want to tell it like it is, so here’s the thing: Date 12.1 was probably my worst date ever.

Before I get to what made Date 12.1 so bad, let me just say that, as an nonphotogenic individual (almost all my dates have told me I’m better looking in person–still trying to decide whether this is truly a compliment, since I think the pics I’ve posted are accurate and decent, but whatever), when I see guys’ pictures online, I tend to give them the benefit of the doubt. That said, on paper, Date 12 sounded like a stand-up guy: good job, already had a kid, my age, reasonably active lifestyle, etc. His photo, however, wasn’t the greatest. In fact, it made him look downright ugly. Because he had only posted one picture, though, and it was kind of blurry, I just figured he must be new to the online dating scene, not realizing the importance of a flattering image. Aw, I thought, that’s kind of sweet how he’s so clueless. I’ll bet it’s just a bad angle.

But it wasn’t. He looked exactly like he did in that picture when I met him in person. In fact, he almost looked worse, with deep wrinkles crossing the bridge of his nose, making me positive he’d lied about his age, since there was no way this guy was in his early 40s. Late 40s is more like it, I thought, but really, I was prepared to hear he had already begun his 50s.

Compounding my issues with his looks was the fact that he had way too many buttons unbuttoned, revealing (get this–I’m not joking) a gold chain around his neck. Now, in his defense, he grew up in New Jersey. But here’s a tip for any East Coaster guys who might happen to be reading: we don’t do this in Southern California. Not since disco was popular, anyway.

I’m generally a pretty friendly, nonjudgmental person, though, and in his pre-date texts, he’d asked me what kind of wine I liked. I told him, and he said he’d have a bottle ready for us when I arrived. Nice gesture, right? So even though he wasn’t Prince Charming, looks-wise, I figured we could still enjoy a worthwhile evening.

But then he opened his mouth. Within two minutes of meeting each other, we were already fighting. How do you start an argument with someone you’ve barely met? you might ask. In this case, it started with a discussion of public-school API scores (a standardized testing measurement employed statewide in California). I don’t want to call out where I live, but the schools in my area have the highest scores in the county. This is a fact, one backed by data available on the California Department of Education website. But this guy wanted to argue with me that the schools in his neighborhood were better (although his ex-wife lives in my district, so let’s all do the math here).

Moving on, conversation got creepier and more skeezy, with Date 12 alluding to the fact that he knew I was sexually submissive based on the dating-website personality questions I’d answered. Only with people I like, I wanted to point out, but I just kept changing the subject. In the course of finding benign things to discuss, the reason he looked vaguely familiar to me was revealed: we had been part of the same scout troop, meaning we had tons of mutual acquaintances.

Talk about making a bad date worse! Now, instead of just being able to get up from the bar and leave, channeling my inner bitch, I had scores of people to answer to for my behavior. This is why I enjoy online dating so much–if it goes badly, there aren’t any real-life social repercussions. In this case, however, I had to find an alternative means of escape.

I decided to broach all those subjects people aren’t supposed to talk about on first dates: my divorce, my custody battle, the kid from scouts who died of cancer, the heart-crushing details of his funeral. Yeah, I know it was wrong for me to exploit that kind of information, but I kept shooting pleading glances at the bartender at the same time, trying to telepathically send him the message, Check, please! Only the bartender kept ignoring us, finally bringing over the tab after three grueling hours of disastrous date time.

The worst part, I have to admit, though, was when Date 12 asked me about my astrological sign. “Yes, I’m a ________,” I admitted.

After asking what my actual birthday was, he wanted to know, “And you’re really 42?”

No, I’m really 36, I wanted to say. I just tell people I’m 42 so they’ll think I’m more mature.

“Yes,” I assured him, then asked, “What about you?”

“You’re not going to believe this,” he said, digging into his back pocket for his wallet, then producing his driver’s license for my inspection.

Know I don’t like to cuss, but, Fuckin’ A!!! Dude had the exact same birthday as me. Exact same year and everything.

You, me, and [insert name of goofball hair-metal-era lead singer who’s repeatedly been kicked out of his band], I couldn’t help thinking. No one cool ever has my birthday!

Date 12 tried to get me to go back to his place with him after we left the restaurant, using smooth lines such as, “I really didn’t think I was going to like you.”

Yeah, well, thanks but no, thanks, I wanted to tell him. Because we had so many mutual friends, though, I made excuses about having lots of work to do and drove away vowing never to see him again. He did, indeed, wind up asking me out again, but I pulled the Date 17 card, saying someone from high school had recently come back into my life, and I wanted to see where things were going. True, that, but still–sometimes it’s best to just shut up, be diplomatic, and chalk the whole thing up to being a learning experience.

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.