When it rains… pt 2

(You can read part one here.  Quick summary: I slept with my best friend, Stephanie, while she was visiting, might have messed up that relationship.)

After I broke up with Stephanie last year I realized I wasn’t in a place for relationships.  Mentally, emotionally… with the impending move and everything, I just couldn’t do it.

But I didn’t want to be celibate either.

Enter Jane.

A few months after I broke up with Stephanie and she moved away (months apart), I put up a Craigslist ad for a FWB.  I met Jane, who is one of the most fun and interesting women I’ve ever been with.

What was so fascinating about being with Jane right after Stephanie was that they were so opposite.  I mean, opposite in almost every way you can think of except they’re both nice people and have good curves.  Tall, short, dark, light, hard, soft, easy, difficult, etc.

One of my biggest frustrations with Stephanie was that she was a novice in the bedroom.  She wasn’t a virgin but about as close as you can get and still break the hymen.  Not only was she new, she was difficult.  The kind of girl that’s so self conscious and in her own head that she can’t relax and have a good time.  I worked with her and she gained a lot of confidence but I’m… miles beyond her experience level.

Jane is the opposite.  She’s this tall, bouncy, outgoing woman who knows exactly what she wants, doesn’t have a problem getting it, and is a freak between the sheets.  And she was easy in the way that probably makes everyone jealous, she could basically cum on command with almost no effort.  She’s a lot of fun.

Jane and I had a good time for about a month until she met her current boyfriend.  We broke off the benefits part but stayed good friends.  She’s wacky and fun… and part of me was pretty sure it wasn’t going to work out with the BF.

Anyway, while Stephanie was here I told Jane that I slept with her and wasn’t sure if that was a good idea or not.  Jane’s my friend, I tell her most things.  We hadn’t been involved in six months and she was the one that broke off the sex when she met her guy.

I wasn’t expecting her reaction; she got jealous.

She didn’t do anything too out there, and she wouldn’t admit it, but she reacted all week.

What’s weird though was as soon as Stephanie flew home…  I found myself craving Jane.  Weird, right?  Maybe it was something to do with tapping the keg and wanting more sex, maybe it was because last time I stopped seeing Stephanie I moved on to Jane, maybe after a week of fun-sex part of me was really craving some dirty, wild, sloppy, nasty shit.  I don’t know why, but it definitely happened.

And then Jane started talking about how poorly things were going with her BF, she’s unhappy, and how every relationship she’s ever been in she’s cheated.

This was less than a week after Stephanie left.

Jane went on about how she’s really not getting what she needs, and she’s ready to leave the BF.  She started getting really flirty with me and it’s only gotten worse.

This weekend, Jane was hanging out with me on my couch in a long t-shirt and nothing else.  Long story.  The first night we met up as FWB started in almost exactly the same way.  We’re drinking, we’re having a good time, we’re flirting a bit…

Before anyone loses their mind, I didn’t sleep with her.  It was plainly obvious that that was on the table if I wanted it but I didn’t want to put myself, or her, in that position.  I gave her a ride home instead.  I’m actually friends with her BF, I’ve been making a very concerted effort to not be that guy.  That said, it’s not easy.  And, like I said in the previous post, I’m bad at not sleeping with women.

The problem with Jane is that she’s just like my ex-wife, if she can’t have something she wants it even more.  Me not having sex with her ramped up her flirty texting to NSFW level.


Another strange fact, both ladies have a sixth sense for when the other texts me.  I can’t talk to just one, the other almost always pops up halfway through.  Can’t even finish one reply before I get a new text from the other one.

So, this morning I was chatting with Stephanie who was going on about how she might have to buy a body pillow because she misses the cuddling, while Jane is texting me about the new sex toy she bought and how she’s going to have to do laundry because her sheets are soaked.

I felt like I was losing my mind.  I got nothing done.

I have exactly two close personal friends and right now they’re both trying to sleep with me.  This probably isn’t going to end well.

14 thoughts on “When it rains… pt 2

  1. omg. How????? How did you get yourself into this? Lol. I think it’s time you get married. Not even kidding. You clearly need a meaningful friendship with lots of sex. And sounds like neither one is your type of wife. Stephanie = too much. Jane = just ….no. Although I think you might be a little in denial about Stephanie. I think you care for her more than you’re letting yourself admit. She sounds like a really smart chick who’s picking up on stuff that you’re (not consciously) putting out there. Jane just needs to have an internet sex channel and she’ll be fine.
    And don’t knock almost virgins, man! Women are stuck. You have a ton of sex, you’re a slut. You don’t have much sex, you’re frigid. Not fair.
    Lots of things to say here about Johari’s window, too … Just get married!!

    • Yes, obviously the solution to a complex situation is to inject religion and the government. Lol

      And I never said there was anything wrong with the almost-virgin thing… or the easy thing… I tried not to judge either of them, just illustrate their differences, because they’re both important to me in their own way.

      And, honestly, without tooting my own horn too much, I’m about the best partner for someone who doesn’t have much experience. I’m experienced, patient, kind, I’m easy going… The only reason Stephanie has any confidence in the bedroom at all is because I helped her get there.


      • Yeah. I thought you’d like that. Lol. Whatever. You got yourself into this, I’m just trying to be solution oriented! Oh, and I’m sure you are the best everrrrrr . You were probably all, “don’t worry. I got you.” And she was probably all, “its so big. It’ll never fit!” Newsflash: it always fits, Id.

      • Sounds like you’re focused on my cock for some strange reason. Would you like a picture with a ruler so you can check for yourself?

        It fits, obviously, or there wouldn’t be much to post about, would there? 😉

      • Is that the same kind of avoidance where you pretend to ignore the valid points I make? I’ve heard that’s also called D-nile.

  2. I’m pretty sure I’m injecting myself into what appears to be an inside-joke conversation, but all penises aside…
    It sounds to me like you need a new Craig’s List ad. If I remember correctly, you’re relocating (or did you already do that?) and so any commitments aren’t going to fly right now?

    • Yeah, I’m insanely busy for the next six months and through the move. That’s why I haven’t been advertising anything, I haven’t been looking for anything. I had basically given up sex/dating for the rest of the year and then this stuff happens, talk about spiraling out of control.

  3. Step 1: Sell the Couch of Plausible Deniability. Seriously, none of what you’ve described “just happens” or even “accidentally” happens. Stuffy, upright, uncomfortable-for-sexytimes wingback chairs are the furniture of choice if you’re trying to get better at not fucking women you shouldn’t be fucking.

    Step 2: Admit that Jane isn’t the only one in this situation who wants things extra-hard or even only because she knows she shouldn’t have them. Sounds like all three of you have a bad case of that going on.

    Step 3: Make an excuse and then ghost on these ladies like it’s an Olympic event. Because your phone is full of Text Messages of Veiled Encouragement, and the only thing more appealing than a Bad Boy is a Bad Idea. (If Ben & Jerry made that a flavor it would fly off the shelves at twice the price.)

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