Another Craigslist Hookup- Warning Graphic

Regular readers may remember my disastrous craigslist hookup from last December. I have made other attempts at that but didn’t get anything going until this week.

I put up my own ad, without a picture; replying to ads is pretty much a waste of time as the ones that aren’t bots designed to collect email addresses get at least 50 responses, for average women or worse, God knows how may for hot women (which are most likely to be bots anyway.) I posted under “casual encounters” for “NSA (no strings attached.)” I get a response, I send her my picture, but I didn’t get hers.

I met her Monday  afternoon. I suggested one place; she looked it up and told me it was closed Monday, so I told her to meet me at a place a couple doors down. She had described herself as very short, chubby, with glasses.

She shows up late and she’s as described, more or less, sort of cute in a funny looking way. We get some coffee and sit down on a couch; this turned out to be a stroke of luck, as the other place only has hard chairs and tables. We chit chat a bit; I remember this is not a date, we are meeting for casual sex, so after a few minutes I put out my hand to hers, and ask her if it’s OK to touch her. After a little bit of hand stroking I pull her up next to me and we cuddle a bit.

We are still talking a bit, and I describe my employment situation as “between contracts” (i.e. unemployed) and staying with friends, as I have just got back into town (i.e. living with my dad.) I see her working this over furiously in her brain; looking quizzical, nodding, and eventually deciding, yeah, I guess I can live with that, as she didn’t deescalate and leave. We kissed some, I furtively groped her, but we had to keep it a bit cool as we were in a coffee shop by a picture window, not in a dark booth in a bar. She told me she had the week off although she still needed to do a few work related things.

I ended our session, and we parted ways outside. I told her I’d call her the next day.

She sent me a very nice email saying how much she’d enjoyed herself, and mentioned various other disastrous meetings. I do at least have manners and a certain amount of savoir faire.

So, at this point it appears I’m good to go. My big problem with having sex with a woman for the first time is anxiety; and as you can read in my previous hookup post, not even ED drugs overcome this. Anxiety must be confronted; I decide I’m going to meet her at her apartment, but plan on just groping like we did in the coffee shop, only with less clothes on.

I called her the next day about noon, and arranged to meet about 1:30; I told her I needed to see somebody at 4 to establish a time limit. I go over. She told me she had a cat, and I was afraid the place might smell bad, but it was fine. We settle on the couch and pick up where we left off. After awhile I say let’s take our shirts off; she says just shirts? and I tell her whatever she’s comfortable with, so she takes her bra off too. We keep at it, she straddles me, and asks me if I want a massage. She works on my neck for a while and then says it would be better if I would lie down.

All this time my mind is racing. It occurred to me my mind is my biggest enemy; it’s my biggest source of pride, as one of the few things I’m fairly confident of is my intelligence, and yet the thoughts I think also fuck me up and cause all kinds of problems.

Was the suggestion we go to the bedroom her escalation? I suppose so, but I was just going to go with the flow, do what I wanted, and not worry about what happened. She massaged me awhile there, and then I move us into a normal position for more groping.

I’m not getting much of an erection at this point, but again not worrying about it. I get my had to her crotch, caress her clit a bit, and then go inside for the G-spot. I worked her over good and she was going crazy for a long while. Eventually my finger tired and I stopped.

She had her hand on my dick the whole time and starts to work on it a little more, and it’s getting harder. I ask for some lube and she goes to work with that. I close my eyes and think about some other woman doing it, and I’m really getting off. It gets very intense,  I come, but she keeps going and I have to tell her to stop, out of a combination of excessive pleasure and discomfort.

It’s getting very close to 4, so she gets me a towel and after cleaning up I put on my clothes and head out. I thanked her for a very enjoyable time and suggested we get together later in the week.

It had gone farther than I had planned, but not all the way to intercourse, which I’m still nervous about. I don’t think I can maintain an erection with a condom on, even with ED drugs; but I have to recondition my body to respond differently. (Christine O’Donnell is right, masturbation is bad for you.) It’s a low-risk way of practicing so the only thing to do is decide how long I want to wait to try it again.

As Assanova says, nightclubs undervalue men; online contact way undervalues men. If I was employed and any kind of game I would be doing way better than this. But I have crippling approach anxiety which I have to deal with somehow.

13 Responses to Another Craigslist Hookup- Warning Graphic

  1. NMH says:

    I don’t pork any woman unless I think that there is the possibility of an LTR, but that’s just me…..

    Anyway, ask her to lose some weight if she wants an LTR with you.

    Good luck, dude…………

  2. MackDamage says:

    Interesting read, I think you should never risk taking off ‘the jimmy’ for good sex bruh! . I feel you man I like going raw but first I make girls take a std’s test and then I put them on birth control .

    Besides getting them pregnant you can get some sort of disease .

    Keep it Mackish !

  3. Sheila Tone says:

    No way, there’s really a G-spot?! No there isn’t. Is there? How come you know about it?

    Re the condom troubles, well, what did you do with the pros? You used protection with them (I hope).

    Maybe you just need a no-intercourse rule. Say it’s your morals or something. I predict most women won’t mind.

    It’s a lot of pressure to put on yourself to meet someone you don’t know for the purpose of having sex, then just have intercourse with them. I always thought half the fun was at least pretending you weren’t sure.

  4. raedawn says:

    there’s no G-spot, he’s making it up. like Louie on Taxi about that spot on women’s left feet.

  5. Omega Dork says:

    I don’t know how you would rate yourself on the 1 – 10 scale, but I was wondering if it wouldn’t be a good idea for men with poor social skills and/or approach anxiety to make approaches to women 2 numbers lower than themselves over and over again. These women shouldn’t cause anxiety to kick in as even to an omega they wouldn’t be seen as anything really worth catching. What do you think?

    • jacobus says:

      Nope. It hurts worse to get rejected by a 4 than an 8.

      • Omega Dork says:

        Well, the point is that you are less likely to be rejected because you will be more relaxed in your approach, and because you are asking someone inferior to you. And the bonus is, that after lots of these types of encounters you will get better at doing them.

      • See my earlier post “Fat Chicks and the Omega”. Shooting lower is no guarantee of success.

  6. Jake says:

    There’s no need to be a socially inept nerd. Manhood101’s free ebook teaches men how to be socially competent. Anyone who is omega stops being omega after digesting his ebook. How do I know? I used to be one:

    Click to access principles101.pdf

  7. Candice says:

    Thanks for sharing! 🙂

    I agree with Sheila about having a no intercourse rule – I would actually prefer a man that took things slow. I also think that being anxious about getting close and personal with someone you don’t know is quite normal! Also, some of my male friends say they have difficulty gaining an erection with someone they are not attracted to and in love with.


  8. Anonymous says:

    Look just be confident a craigslist hook up is easy you dont know her she dont know you who cares what she thinks goin with a big head fuck and leave if she wants it again go for it if not find another Craigslist hookup

  9. George Miele says:

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