a squirting second date

A two-year wait for date #2

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Jake’s profile had appealed to me for a few reasons. It was well written and honest and had intellectual depth. He was tall and bulky and while not conventionally attractive I liked his look. Obviously, I liked that he’d followed up with me each time I came back online.

He asked me when I wanted him to come over with a bottle of wine. I told him I didn’t lead with sex anymore and perhaps we could go out for dinner. He was good with either but reminded me we’d already had sex and he knew we were both sexual people.

At some level I believed it wouldn’t make a difference with him. From the beginning, I think he was more like Jason and Andrew, where even if you have sex with them early they still see you as relationship material.

I’d been out every single night that week. I didn’t expect Jake to show up much before 8pm; he had his son and was taking him to his ex’s after dinner. I debated whether I wanted to go out for drinks versus stay in. It was less about sex and more about wanting a quiet place where we could talk about anything, and I was tired of being out.

I ate alone (Maggie I now think of you every time I eat by myself!), tidied the house, had a glass of rosé, prepared a cheese plate, got caught up on some reading and writing. He showed up when he said he would, bottle of wine in hand. It’s sad when those are notable things, isn’t it?

I poured us the wine and we sat on my couch and talked. And talked. And talked. About kids, trips, what happened the times I flaked out on him, communication styles, why he was initially intimidated by me, work, exercise (he used to be a personal trainer), and lots I can’t even recall.

Until he reached over and grabbed my arm and pulled me into him for a kiss.

It. Was. Great.

We didn’t stop, the intensity grew, and he pulled me over to him so I was straddling him on the couch. He said “when did you decide we were going to have sex?”

I was sincerely puzzled, so said “what makes you think I decided we were going to have sex?”

He thought because I invited him to my place it was a foregone conclusion for me (and he wasn’t being gross about it). I explained I hadn’t assumed either way, I simply wanted a quieter place to talk and was tired of going out. I reminded him I am skittish about jumping right into sex with anyone anymore, because to have sex with a man right away means he takes me out of the “relationship potential” box and puts me into the “sex only box.”

He told me he was different and I said I tended to believe it based on his profile and his interactions with me. He told me his last two long term relationships started with sex right away.

We kissed some more and he asked me if I wanted to take him upstairs to my bedroom or if I wanted another glass of wine. I said “both, please”, so that’s exactly what we did.

I have another post in progress about how each sexual experience I had that week, and Jake was different yet again. Unlike the emotion-free sex on Monday and Thursday, or the entirely emotionally laden night with Tony, this was somewhere in between. Jake took his time playing and undressing me. He was affectionate.

And then he was crazy hot. Once I was naked he expertly went down on me. He then hooked his fingers into my g-spot and I was cumming in seconds. When he then started to slam the heel of his hand against me at the same time, even through my orgasm haze I knew what he was doing. Seconds later I squirted all over my bed and him.

Simultaneous thoughts went through my mind but the one I managed to get out in a stutter was “did… did… you… do that to me the last time?”

“No Ann, I didn’t.”

“Wow, that doesn’t happen very often.”

“Well babe, it will happen every time from now on.”

And with that his cock plowed into me.

Without a condom.

I should have freaked out but didn’t. Later, he pulled me on top of him, commenting he was surprised he’d been able to last so long since it had been such a long time. He was in control the whole time, he put his hands exactly where I wanted them and helped guide my motion back and forth.

He came with a flourish and a shudder. Afterwards, I chastised him for not being safe. We lay in my bed drinking wine and talking for over an hour. He made me soak my bed a few more times.

Almost succumbing to sleep, I told him he was welcome to stay but he said “oh no, it’s too soon for that just yet”. It didn’t feel emotionally distant, it felt like he was appropriately pacing himself. And yes, I know I just described us having sex on our second date after two years of not seeing each other, but staying over is a different level of intimacy I suppose.

All in all, it was good. He’s easy to talk to and we are physically compatible. He seems emotionally mature and he’s ready for a relationship. He’s almost a decade older but it’s not obvious to me. We have fairly different lifestyles as a result of where we live (I’m in the city and he’s in a distant suburb) and our jobs (he’s blue collar, I’m not), but I don’t know enough to know if that will be a barrier.

He’s not a “slam dunk” in the way that someone like Kyle appeared to be – but it was just appearance, nothing else. Perhaps there is something deeper here, perhaps with a few more dates something will reveal itself to not work. If there’s one thing I’ve learned with dating there are surprises waiting around every corner.

I keep hoping the next surprise is a good one.


[Image from the movie “Night of the Living Dead”]

39 thoughts on “A two-year wait for date #2

  1. How can you compare Jake and Kyle’s “slam-dunkedness” when you’ve only had sex with one of them? Or did I miss something?

    • I wasn’t referring to sex at all. I was referring to some men checking all the boxes on the surface (tall, handsome, good job, well-spoken, etc etc) where others may be ultimately more compatible and emotionally mature but you don’t always see that up front.

      • I didn’t mean to say that I believe that sex is the main factor you consider in slamdunkedness. Just that is an important factor. Now I know that slamdunkedness is something different completely…..I think…,

  2. I agree, sleeping in is a different level of intimacy. One we didn’t get to achieve until last weekend. 15 months later 😛
    It doesn’t mean anything.
    And you know I’m not a big ‘no sex’ girl, because it somehow worked out OK for me.
    So yeah, take it one day at a time, and keep seeing the positive outcome you wish for (someone who supports and loves you and shares his life with you, if I understand correctly). Don’t put a face on him just yet, but… keep focusing on that image. One day the surprise will be good 🙂

  3. takes me out of the “relationship potential” box and puts me into the “sex only box.”

    I love this quote Ann. I’ve not heard you mention it before. I was going to suggest this. How long have you being following this theory?

    This guy is correct. The odd guy is the exception to this rule.

    • It may be the first time I said it that way, but definitely not the first time I’ve talked about it. It started to become real for me in the first year I became single, when I met guys who swore up and down they were looking for a relationship, we’d have sex on the first date, and then that’s all it was.

      It was actually Lewis where it really crystallized… I opened up to him about my sexuality early on and then he faded away. While the two may have had nothing to do with each other, it certainly felt that way at the time. I can’t help but wonder if I started differently with him if things would be different now.

      I have experienced the exception and been lucky – Jason, Andrew, even Tony, all fell into that category. But while men say they want a woman with the full range of madonna to whore, they don’t seem to know how to deal with it when they get it.

      • Ah, yes, the all too common jarring disconnect between the idealized abstraction and the tangible reality.

        • but I think it’s because the majority of men have not evolved to a maturity level to embrace this type of woman – it takes a specific combination of intellect, passion, and maturity to rise to the level required for our type of woman lol

  4. “But while men say they want a woman with the full range of madonna to whore, they don’t seem to know how to deal with it when they get it.”

    A truer statement has never been spoken. And of course I speak only for myself.

  5. I’m personally torn by the early sex too….I’ve waited and not waited and either way things have been great or not. Currently seeing a guy who I have slept with on the first date and things so far are going well, but it’s only been two dates since he’s back working in a different city and I’ve been on call more nights than not. We didn’t talk about sex at all until we had sex and it’s not currently the focus of our current conversations but now it comes up. I can’t wait to see him again and somewhere in my cynical soul I want this to work out, at least a bit longer, to see if we truly are compatible.

    Dating is hard. I hate rules and fake rules and the games!!

    • I rail against what I consider to be fake rules, just like you. But when I experienced over and over again what happens when I lead with sex, I couldn’t ignore it. So now I try to at least hold back on the first date, maybe the second, before we have full-on sex. I don’t know that it makes a difference but at the very least, it took away the worry that perhaps something didn’t work out because I had sex with someone right away… That ultimately was the worst part of it.

      I hope it works out with him!

  6. As a man the Madona to a Whore is also true. Men do need that I believe. Your onto something with the above.

    Also to continue the type of dating site sets a tone for what happens next. Vanilla or not. There are exceptions. I do hope you can get to the gallery and concerts with someone one day. AND have great sex afterwards. That’s the holy grail.

    • I would love that. It’s what I had with Tony in terms of varied interests…but those interests didn’t always translate into actions, but that wasn’t what killed the relationship. You know the rest of the story.
      But that is the holy grail for me. It’s the thing that has me interested in Lewis, for example.

  7. Thanks for letting me be your virtual dinner companion. 😎

    I like this guy. He’s straightforward and doesn’t sound like a BS’er. I think the majority of men of men prefer the thrill of the chase when it comes to sex or no sex during the first couple of dates. Sorry guys, but even though I’m very guilty of first date sex (my first date with the Ex ended with sex), I think you engage better when you have to work for it.

    • I like him too, he’s very much a straight shooter and boy do I appreciate that given the other men who’ve been in my wheelhouse recently.
      And I completely agree with you about the chase.

  8. Not to indulge the prurient interest, Ms. St. Vincent—only for tutorial and self-improvement purposes 😉— please consider clarifying “slam,” “the same time” and the site of said hand heel “slamming” in the following:

    [H]e then started to slam the heel of his hand against me at the same time[.]

  9. Glad you had a good time. But..

    >Afterwards, I chastised him for not being safe.

    Ahem, that’s both partners’ responsibility, not just his, young lady.

    • Of course it is!!
      What I actually said was “well I guess it’s too late for us to have a safe sex discussion” and he said “hey when you squirt on my hand like that I’m not stopping to talk”… And that’s when I playfully punched him.

  10. Your quote: But while men say they want a woman with the full range of madonna to whore, they don’t seem to know how to deal with it when they get it.
    Resonates deeply with me Ann for many reasons I won’t get into now.
    Yes, ride the waves so to speak with this one and forget Kyle! He obviously has something else going on or something. Who knows? And no time to waste trying to figure out why he ghosted. I know it’s hard to get the ones who check off all the boxes out of our minds, but the real prize may be in box #2. 🙂

  11. Re the madonna/whore thing (ugh!) for men who HAVE that attitude, I think they can combine them, but IF they do, what they want is the madonna FIRST which allows them to imagine that the whore is *just for them* because they have a magic penis.

    If they get the whore first, they think ‘whore for anyone’ and that squicks their tiny male ego brains (the ones in their dicks) and puts the woman in the ‘not relationship material’ box.

    Either way, if a dude thinks like this, he’s got some fucked up opinions about women which are probably going to show up in other ways sooner or later.


    • I think you’ve nailed it, Ferns (not a surprise!). I’ve definitely had men say they like the idea of me “being a slut” but it only works when they think I’m slutty for them. Which of course doesn’t make any sense at all practically.

      I’ve certainly met a lot of men who like the idea of their partner being a little “dirty”. I’m not sure this is a messed up idea inherently, but I’m not sure what the right balance is in attitudes. I mean, if I’m going to find a good partner for me, won’t they have to embrace my full spectrum?

  12. I love that he “hooked in to your g spot” – so many dudes are oblivious that it’s not all about the old in-out / that there’s some manoeuvring to really hit the spot hehehe!

    In other news, I’m glad to see you having some fun experiences 🙂

  13. YES to “I’ve said to myself “what would I do if I believed he was actually interested in me?” and so have reached out a few times proactively.”

    Opens up worlds of possibilities.

    • I can’t get pregnant. You know that. I wrote about removing my Fallopian tubes two summers ago. The risks *I* take (mr pull-out and rhythm method, as evidenced by your blog) could never produce another human.

What do you think?