More Hooking Up

I had a meet with the craigslist hookup for Friday afternoon,  but she had to cancel. I told her I’d call her on Monday. I checked the email account I use to troll for hoes late Sunday night, but not before I had choked the chicken.

She again gave her regrets for Friday and said she could see me Monday afternoon or Friday afternoon. I have been avoiding jerking off a day or two before seeing her to try to improve my sexual performance, but I didn’t want to wait until Friday. So I called her and told her I’d come over.

I have used Viagra in the past to overcome the erection-killing effects of condoms, but I have been trying to get to where I can have intercourse with a condom on, orgasm, without any ED drug. I had not actually successfully penetrated her and I was getting tired of it so I took half a 100mg Viagra. I got some LifeStyles Ultra Thin condoms and went over.

Long story short it still wasn’t working. Without the condom on, erection, put it on, the erection dies before I can get inside her and won’t come back. It’s got me pretty discouraged.

I talked to my friend about this. He gets a fair amount of sex, but mostly from fairly unattractive women. He said sometimes the little man in his brain says “No, I’m not going to do this” when he’s with an ugly woman, and it pisses him off, but there’s nothing to be done. He says I need to find a better-looking hookup.

I have been meeting various other women off the internet, mostly a few years older. I took one to dinner Friday night; she is a little shy but I’m sure she wants to go for it. I’m meeting another tomorrow who seems pretty eager. I think I won’t know how it will go until I actually have sex with them; but my friend is probably right, you may intellectually want to have sex with an ugly woman, but if your brain says no, it won’t happen.

One thing I have noticed about guys who get a lot of sex is that usually they will have sex with anything- they may get hot women, but if there is not hot woman at hand they will do an undesirable one. I suspect guys who get a lot of sex typically have a high level of testosterone, and this trumps money, looks, game, or anything else. And also allows a guy to have sex with unattractive women.

So I’m going to keep working on this.


9 Responses to More Hooking Up

  1. Oh Megatron! says:

    so did you “practice” with those condoms? I’m serious. I’ve had similar issues and managed them by only jerking off with condoms for a month or so. It was super frustrating but it achieved a few things. First, I think I started to associate sexual pleasure WITH wearing a condom. Second, because I had to use lube everytime I jerked off, my “happy alone time” became more like simulated sex when compared to my classic dry jerk method. Third, it allowed me to try a shit-ton of different condoms so I know the 2 or 3 brands that work for me now. Try it for a week and see. At first you will end up wasting a lot of condoms because you will get hard, put a condom on, jerk and not be able to keep it up but give it a few days and it WILL start to get easier. Just grab a sampler from one of the online condom sites and get to work. This is kind of crazy but now I kind of like jerking with a condom every once in a while…when i want to try a new brand of condom (or lube) or when I just feel like mixing it up. Good luck and hope this helps.

    • For a long time I masturbated just by rubbing up against something. I got nothing from using my hand. That obviously is nothing like a vagina so I only used my hand for a while and got so that worked pretty well. Then I started using a condom and got to where that worked pretty well.

      I have also used the Fleshlight, but I can’t use the Fleshlight with a condom. I think I need to try a different Fleshlight; the one I got was the only non-vibrating one the store had, and it has a smooth interior, which may be part of the problem. Also I was most recently trying it with the Skyn condom, and the polyisoprene doesn’t seem to work with the Fleshlight material very well, even with lube there is too much friction.

      Fleshlight sells devices in which to place it to simulate different sexual positions, so I think I’m going to try it with a different one in the missionary position box. It’s a matter of adapting the body to a different form of stimulation and I guess I have a way to go.

  2. Mahoney (the key board warrior) says:

    Mr Omega, don’t take this the wrong way please but this just all seems so pathetic. I am also irredeemably sexually inadequate in such a way that far surpasses whatever troubles you have in that area. So I am not coming at you from a position of contrived superiority. I think for certain unfortunate men (I am such a man) sex can mostly only offer them pain, suffering, humiliation, self loathing, envy and constant exposure to those feelings will ferment deep feelings of bitterness and general misanthropy. Sexuality is potent stuff and as wonderfully rapturous and ecstatic as it can be it can also offer pain of the same intensity. I don’t know how much your sexual inadequacy bothers you, mine makes me feel like a walking corpse 24/7, from my perspective you have repeatedly displayed great courage to face the constant shame and humiliation of erectile dysfunction. By the way have you ever been mocked by women for this failure? For that is truly my worst nightmare, I actually have literal nightmares about it from time to time, I cannot possibly imagine anything worse than that.

    My question to you is, is it worth it? Is the pleasure you derive from having sex with these women worth the pain and the shame, or doesn’t it effect you as deeply as it effects me? What do you value more about having sex, is it the pleasure (seems unlikely to me) or it the sense of social validation, the sense that you become a normal, worthy human being? I see so many men go through such pain and agony just to get a whiff of pussy, just as so many men endure untold, searing emotional pain during divorce. Was that lackluster, flimsy, illusorily sense of companionship and “love” which only stays for a season then wilts, worth having a deep emotional scar which takes decades to heal and renders you dysfunctional in various ways? Is it worth the pain man? It just seems to me that for men with an extremely low sexual market value it couldn’t possibly be worth it.

    I am coming from a position of never having had sex (due to my sexual inadequacy) and I’ve never falling in love either. I know that R Don Steele said, without reservation, that love is the greatest thing in the world, do you agree with that assessment Mr Omega, is it worth that kind of pain? The sexual escapades you report remind me of the part of the novel 1984 where Winston Smith had sex with the prole prostitute, he described it as filthy, dirty and disgusting yet he did it anyway. If a man has to exert extreme levels of concentration just to get an erection doesn’t that make the sex truly more work than pleasure?

  3. Mahoney (the key board warrior) says:

    Mr Omega, I have a request and I want to put it to you in the strongest possible terms. I have a film that you absolutely MUST watch. This is a film of the ultimate prototypical beta male, reveling in his status of humiliated sexual loser, in love with his own agony, yet amazingly actually seems to pull chicks. I think this is the kind of film that should be discussed and dissected by the manosphere heavies but I think you should start it off. It is a true portrait of today’s modern emasculated male who is more than willing to undergo humiliation in order to stick his nose in the crevice. This beautifully illustrates and expands on all the questions I asked in my above comment. It also details his struggle with erectile dysfunction. The film is called A Complete History of My Sexual Failures. You will not regret the decision to watch this film so please obey my request. Here is a link to the full film:

    • My internet connection is often very slow, so I can’t watch that now, but I’ll try to watch it soon.

      The whole thing is pretty discouraging sometimes. Nevertheless I feel like I have a problem, and I want to solve it. So I’m going to keep working on it.

      There are a lot of things that can cause unsatisfactory sexual performance. Anxiety; lack of experience or recent practice; dysfunctional conditioning of the arousal response; or maybe other things. The thing I fear most at this point is I’m getting old enough to where it’s physical. But even that can be overcome with ED drugs; if you’re taking ED drugs and *still* can’t get it up then it has to be a matter of fear or conditioning.

      I would recommend looking into surrogate therapy- You can talk to a sex therapist and practice some things with an actual woman which should help. This helped me a lot; it’s not cheap but worth the expense.

  4. Eurosabra says:

    I would recommend the excellent essay “How Do You Fuck A Fat Woman?” by Kate Harding in the _Yes Means Yes_ anthology, as well as “Towards a Performance Model of Sex” by Thomas MacAulay Millar, and the YMY blog as a whole.

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