First, if anyone takes the time to read all of this and reply, thank you. I appreciate it, seriously. I feel like giving up altogether. I probably need therapy rather than advice from AskTRP, but I truly appreciate any insights you guys have.

About me: I'm almost 40. I'm intense and passionate in my professional life. I'm highly successful and a well-known dominant figure in my field. Financially, I'm set for life. I can hold an interesting conversation and I have friends, skills, ambitions and hobbies that have nothing to do with women. Generally, I lead a fulfilling life.

Also about me: First, I'm overweight, technically obese by the medical definition. Although I carry it well, I'm definitely huge. Still (and I know I'm hamstering) I'm 6'4" with broad shoulders, I dress very well, maintain myself, and I've been told I have "classic tall-dark-handsome symmetric features". I get tons of attention from women, all the time. But, I have very little actual experience with women.

I spent 20 years unhappily married, from a young age, and I've been divorced for 2 years. I've pretty much never known what it takes to escalate from a sexually-charged conversation/atmosphere into more. I feel lost when I get to a certain point. I have confidence in my daily life. I have persistence and discipline in my career. I have no problem approaching or talking to total strangers in a professional setting. Yet, when I'm in a one-on-one situation with a girl and she's clearly sexually interested, something blocks me and my confidence crumbles. Almost like I'm waiting for her to physically escalate - something I know will never happen.

Here are the experiences I've had since my divorce. I didn't pursue these women knowing they had boyfriends - they've come on to me and then later dropped the fact they have a boyfriend. Every single one of these conversations happened on a one-on-one romantic dinner date with alcohol involved, that we DIDN'T call a date, but was basically one to me. They never refer to me as a friend and basically never mention their boyfriend, unless it's in a way that she's trying to make herself feel less guilty.

Girl 1) Engaged. Constantly dropping hints about BDSM and told me that "most girls probably wouldn't try stuff, but I'd be up for trying whatever you wanted, no matter how weird or kinky". This is when I started a really bad habit that reoccurs later, of diverting the sexual conversation to be about a "generic" girl rather than asking/suggesting things about her. For example, I'd reply, "oh really? well I like the idea of tying A girl up", rather than her. Didn't escalate at all, and she lost interest.

Girl 2) No boyfriend. Spent the entire night saying how "perfect you are for me" and how she "wish I was married to you so bad. can we work on that?" Didn't escalate that night. Later, I told her I liked her verbally (I know...), and got "I don't see you that way, but we're good friends".

Girl 3) Long-distance boyfriend. She told me she "likes anal", and "want to get a room with you, even tho nothing has to happen". Didn't escalate that night. Got a second chance/date. On this, she told me that she "already can feel how intense you'd be sexually and I haven't stopped imagining us together. I want to be naked for you". Didn't escalate (I know). I asked her how her boyfriend was (I know...) and she said "there's no need to talk about him!" Later, she burst into tears and said "I wish you had kissed me, this isn't working the way I wanted it to", then completely lost interest.

Girl 4) Married. Actually escalated with lots of kino. She asks to come back to my place and get into bed because she's "really cold". Got into bed. Start touching her, and then just couldn't bring myself to go further (because she was married). Asked her to leave, she said "thank you for not taking advantage", then never spoke to me again.

Girl 5) Engaged. She said "I think some girls would be put off by your size in the bedroom, but I think I'd be intrigued by you sexually". Didn't escalate that night. Later, I told her I'd thought about us in that way before, and got "Don't say things like that".

Girl 6) Boyfriend. Constantly staring into my eyes and saying things like "I just love being told what to do". Said "I'd never cheat on my boyfriend but a little kiss on a night out isn't really cheating", and "I'd be really annoyed if you touched any girls that weren't me". Didn't escalate. She lost interest and stopped talking to me.

Girl 7) Boyfriend. Partial success, if you could call it that. Didn't escalate, but later, she moves to a distant city with the boyfriend. Starts sexting me and sending me nudes totally unprompted, revealing her dirtiest fantasies, and saying "my bf can NEVER find out about this". A good time was had by all - by text (I know). Later stops talking to me.

Girl 8) Current girl. Has a long-term boyfriend. Talking about kissing and she says "a really good kiss gets me wet". Later talking about bondage, I do the generic girl thing again of "yeah I love tying up A girl". She still seems intrigued, asking me "what I'm into in bed", here I changed the subject awkwardly. Telling me how amazing and kind her boyfriend is, that he's a good home-maker and provider, but "if something happened and he didn't find out, I can't see the problem with that". Continually touching me then pulling back and saying "sorry". Didn't escalate. Happened to meet her by chance the next day and she was snappy, and argumentative. I could probably get a second "date" with this girl, as she's still texting me and talking to me, showing interest - if there's any point.

One close friend has told me, "there's clearly sexual tension, and these girls are clearly showing the potential for more intimacy with you as long as they have plausible deniability, but caught thinking between whether they should go for it or not, because you aren't showing dominance and escalating... so they feel like they're wasting their time or see them as a friend, and you dry them up worse than the Sahara".

Another close friend has told me, "you can't fight biology, if you weren't so overweight they'd show you more clear IOIs that would make it obvious, they'd throw themselves at you physically and verbally, the fact that you're getting unclear signals is because you're overweight and they can't imagine you hooking up with them. Also what's blocking you is the morality of it, that they all have partners and you know it's wrong".

TL;DR Keep attracting women who are "taken". I THINK I'm getting VERY clear IOIs, but can't be sure because I have no experience and I'm self-conscious about my weight, have never escalated properly, and crash and burn every time. I'd rather even escalate aggressively now and get shot down badly, than continue to hover in limbo for my entire life. Desperate and fed up.