Reading Time – 10 minutes

A special treat today. I’ve decided to continue the series I started many years ago at the prior version of this blog. The series is called The Story Of My History with Women. It’s excerpts from a book that I half-wrote but never published, documenting my entire woman life from high school in the 1980s all the way until 2009 when things started to get really crazy in my dating life two years after my divorce.

I published 16 installments of this series on this blog before I put the blog on an almost permanent hiatus. You can read them all by going to the “Dating Techniques” section of the blog archive here. I strongly recommend you do this since this installment picks up right after part 16 ends, around the summer of 2009, and I refer to specific women whom you won’t know unless you’ve read the prior installments.

The entire point of this series is to show you where I came from (beta male virgin) to what I eventually became (divorced beta male dad in his mid-thirties) to what I ended up becoming by 2009-2010 (guru-level online dating/non-monogamy expert) so you can learn from what I did. Each installment includes lessons that I provide along the way so the stories are for training and not just for entertainment.

If this article is popular I will continue to write future installments well past 2009 when the book ends and I’ll just keep on going. After all, 2009 was crazy amazing but that was a very long time ago (15 years ago… damn I’m old) and I’ve had a hell of a lot more dating adventures since then. Just let me know if you want more of this kind of thing.

As always with this series, everything below is all 100% true and factually accurate to the best of my memory, journals, and extensive spreadsheet records, though all the names of the people described have been changed.

Part 17

Summer, 2009

After years of starving in the desert, I was like a kid in a candy store at this point, now that I knew I could attract new attractive women into my life whenever I wanted. I had previously had four women on rotation but now I was down to two:

HBM – 19-year-old inexperienced Asian FB I saw every week who also cleaned my entire house when she came over.

Darci – Blonde 23-year-old FB college student I saw about twice a month.

Sadie (highly intelligent blonde Russian MLTR, age 23) and Emma (physically fit 25-year-old single mother MLTR) were gone, temporarily, due to the jealousy problems I discussed in the prior installment in this series. So no problem, time to go get more women!

I hit my usual dating sites back then, Match.com, Plenty of Fish, Yahoo Personals (which was getting much worse at this point), and MySpace (not a dating site but one that worked just like one if you knew how to do it, which I did, though it was on its way out at this point) and racked up a more first and second dates.

One was a 19-year-old, very tall virgin (yes, a virgin) with extremely long brown hair and very dark eyes. We met at a Starbucks and she was extremely nervous. I was as nice as possible and made her feel at ease. We even went outside and spoke for a bit out there to enjoy the sun. I was surprised at her height; she was 6’1”, a good three inches taller than me if I was barefoot (I’m 5’10” and a half, just under 5’11”). The fact that I was a little shorter didn’t seem to bother her; she was a Type 2 and interested in older men.

Her ex-boyfriend had “played around” with her sexually (oral sex, some external some fingering), but she had never been fully penetrated.

On our second date, she came over to my house and I followed my standard model, talking to her on the couch for a while, getting her comfortable, before we started getting sexual. I had never had sex with a virgin so I wasn’t sure what to expect.

Eventually, she was almost naked on my floor but still wearing her underwear, which she would not remove. None of my techniques worked. She was not losing her virginity and that was that.

Which was fine. We still did a lot of other sexual stuff and it was quite enjoyable and definitely a learning experience. Though to be honest, kissing her while we were both standing up was weird. I actually had to tilt my head upwards a little bit to do it; a very weird feeling since I’m used to leaning down to kiss women.

We saw each other several more times, always getting sexual but never getting to actual intercourse. She was a very sweet person.

The next woman was another unusual case. She was one of those rare instances where, when we messaged online, she said with no prompting from me “Just come over to my place!”

So I did, very happy and fully expecting sex. She cleverly made sure that I came over 30 minutes before she had to leave for work, giving her an excuse to wrap things up before they got sexual.

She had long, dark blonde hair. She was cute, but a distinctly masculine edge to her personality. She even moved like a man.

She lived alone in a small apartment where I was surprised to see posters of superheroes on the walls like the Incredible Hulk. Never seen a woman’s home decorated like that!

When I asked her what she did for work she said, almost unsurprisingly at his point, that she was a corrections officer at the local woman’s prison, matching her masculine demeanor almost perfectly. She had just broken up with her long-term boyfriend of three years and was looking to quickly get back into the game.

Nothing happened of course since she was quickly off to work within a half an hour. However, the very next day she texted me and requested that I come over to her apartment again and that I should bring a bottle of wine. I don’t drink alcohol but back then I had some in my house because that’s what women liked, so I grabbed a random bottle of $8 wine I had previously picked up and headed on over.

After some wine and chitchat, we were very quickly having sex in her bed. I was half expecting her to have a penis with all that masculine energy, but thank goodness she was all woman.

That being said, it was the strangest sex I’ve ever had. I make a lot of noise when I have sex; during lovemaking I sound like a retarded T-Rex. Women usually like it. She did not. She kept repeatedly telling me to be quiet. “Men shouldn’t make noise!” she kept saying. Of course, I just kept right on making noise and enjoying myself.

When I tried to make her orgasm, she stopped me. She said she was unable to orgasm no matter what men tried and wouldn’t even let me attempt it. She did, however, ahem, return the favor, though after sex she complained yet again about how I should not be “noisy and dominant like that.”

Lesson 29: Always be aware of masculine and feminine polarities in women.

Some women are very feminine, some are quite masculine (though still heterosexual), and some are in the middle, what David Deida calls “balanced.” Women will always be attracted to the opposite of what they are and repelled, turned off, or irritated by men who are similar to what they are. So if you’re a very masculine guy, really feminine women will like you but more masculine women will be turned off by you, at least sexually. If you’re a more feminine guy (though still hetero), more masculine women will love you and more feminine women will be turned off by you. If you’re a balanced guy, very feminine and very masculine women will tend to not like you but more balanced women will be attracted to you, speaking in general.

She was extremely masculine for a girl, and I’m an extremely masculine guy, so even though we were just physically attracted to each other to have sex, the experience wasn’t enjoyable for either of us, and that is to be expected.

When I texted her a few days later just to be nice, she did not respond, and I never heard from her again. For the first time in my life, I had been “one-night-standed” by a woman. She was, up until that point, the only woman I had only had sex with once. Which was probably for the best.

Weird ones come in threes I guess, because next woman I met was yet another unusual experience.

Unlike the first two women, this one was extremely hot to me. She was only 4’11” which I absolutely love (I have a short woman fetish), blonde hair, sharp features, very feminine demeanor, super cute, and 22 years old. Exactly my type.

We went to get a quick drink at a Mexican restaurant. She had no car so I picked her up at her apartment and took her there. As she talked both in my car and at the restaurant, I felt her sexual power wash over me, like it had many times with a few other women. By this point, I had plenty of practice controlling my outcome independence and my frame when sitting across from a super attractive woman, but I still wasn’t perfect at it, and several times I had to remind myself to control my breathing, not say anything stupid and don’t compliment her. It was hard with this one; I was super turned on.

Her life was a fucking mess. The man she called her “ex-boyfriend” was a steroids addict and was often violent with her. She also had numerous cancer and kidney stone problems despite only being 22. Worst of all, she had a bitchy edge to her that I knew would be a problem, even if she ended up just being an FB. But she was so damn hot, I didn’t care, at least not yet.

The date ended and I took her back home. I was happy to see that she texted me again the next morning on her own, this always a big indicator of interest (what I call the Ultimate IOI).

Later that week, I drove out to pick her up from her apartment again, very excited, knowing that the odds of sex were high. Even if I had to relegate her to only an FB, I was fine with that.

Her apartment building was the kind that was always locked so you had to have the resident buzz you in. When I buzzed her room, a man answered. The conversation went something like this:

Him: Hello?

Me: Hi. Is Trinie there?

Him: Who the hell is this?

Me: Caleb. Who is this?

Him: Uh, I’m her fucking husband, bro.

Me: Her husband?

Him: Yeah!

Me: Huh. Alrighty then. Well, you might want to ask your sweet little angel what she does when you’re not around. Oh and tell her Caleb was here to pick her up for our DATE. Have a nice day!

I turned around, got back in my car, and went back home. I wasn’t upset because I never get upset, but I was disappointed that I wouldn’t be signing her up as my next FB. She was so hot! What a shame.

About two hours later she texted me, absolutely blowing up my phone, apologizing and making excuses. I don’t remember what I said to her in response, but I wasn’t going to see her again. I don’t do drama, and she was not only hip-deep in it, but she was also married and lying to me to the to the point where she was putting me in physical danger. Homie don’t play dat.

Around this time, while HBM was over at my house, Shelly texted me out of the blue (she’s the one who posted about our date on my Facebook page in the last installment, upsetting Emma). I had only seen her a few times, each time with many weeks in between, which was not my typical pattern. She wanted to meet up again, and I did so.

The first few times Shelly and I had sex I had to be careful because I was the first man she had sex with after a cervical cancer diagnosis (she was only 29), but soon she got the hang of it. She had a more dominant personality but she was friendly and feminine and we got along well. We would talk about business quite a bit and she was already making over $100,000 at her job in the financial sector.

One time she said to me, “I make a lot of money, and I come from a family that has money, so if I ever get married, he’s going to have to sign a prenuptial agreement. I lot of men won’t like that, but I have to do it.”

Oh Darling, if you only knew who you were talking to. When she said that, I had a huge, ear-to-ear smile on my face that she did not understand (though later she did when I explained it to her).

She became an infrequent MLTR and my third regular woman on rotation, replacing Emma (who left because of her).

Three regulars plus a few random ones on the side wasn’t enough for me though. I wanted more, and I was about to get it.

To be continued…

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Question Of The Week

Long-Distance Women and Spending The Night

E.B. Writes:

I have two questions so hopefully you can answer both of them. If you can’t do both in one go then I understand.

First, I’ve had two different women who live in different parts of the country hit me up and “I’ll be in <my town>  from x to y.  Let’s get together.”

I never know what to make of this.  Are they looking for a random vacation hookup (paydirt for me), a sucker who will wine and dine them while they are in town, or something in between? How would you suggest I handle these women if I just want to hook up?

Second, I’m a little confused about the spending the night thing. You say FBs should not spend the night, but MLTRs and OLTRs can. But you’ve never talked about the restrictions of these women spending the night with other men. Is it the inverse, so FBs can spend the night with other men but MLTRs and OLTRs can’t? Please set me straight on this.

(Just to be clear, I don’t mind answering two questions in one submission as long as they are both very brief. These are, so I’ll agree to it.)

Answer 1: If she’s someone you’ve had sex with before, absolutely I would take her up on it. Do it correctly though! Schedule her in, meet her at your place (best), her hotel room (2nd best), or a bar (3rd best), and escalate right to sex. Bail out fast if sex is clearly what she doesn’t have in mind.

The only exception to this rule is if she’s well over age 33, meaning her ASD has kicked in. In that case, do your best to schedule a meet but sub-communicate strongly that you’re going to “hang out in her hotel room” or your place or whatever rather than going out to dinner or something like that. If she demands dinner, politely pass.

If it’s a woman you’ve never had sex with, skip it unless it’s clear she visits your town often (like for work reasons) and she’s under age 33. If this is the case, meet her at a bar with good logistics (very close to your place or her hotel room) and get as far as you can.

Answer 2: FB can do anything they want, including spend the night with other men, and shouldn’t bother you at all and you shouldn’t care. They’re just FBs.

MLTRs can spend the night with other men, however, if this man is her full-on boyfriend that’s not a good idea. There’s no rule against dating MLTRs with boyfriends but I strongly recommend against it. The possibility for drama, miscommunication, and hurt feelings on both sides is too high.

Your OLTR absolutely can not spend the night with any other man except you, and you can’t spend the night with any other woman except her. It’s sexually open but emotionally exclusive. Spending the night with other people is a line neither of you should cross.