Me, personally, I would fuck the fat girl for a confidence booster.
I've found throughout my life that if I don't have any girls to bring over, I can always get a fatter girl over if I need some. I'm not attracted to fat girls, but I can still have sex with them.
I think the further along in life you go without having sex, the more you fantasize about that "perfect" situation, and the situations in your head are never as perfect as the fantasy; it's always different. Here's a quick example:
This dude I knew, a 23 year old virgin, he goes back to Michigan for his brother's wedding. He needs to fly back to Texas, so his sister's friend drive's him to the air port, an hour away. His flight is canceled, so the girl tells him he can stay at her place.
He goes there, he then ends up laying in bed with her, both of them in their underwear. What happens? Nothing. He made out with her, but didn't push it any further.
I asked him why in the hell he would not fuck her, and he said "I didn't get any signals."
I then asked him why he ended up in her bed in the first place, he said it was because there wasn't a T.V. in the guest bedroom.
So I asked him this "Dude, let's say the exact same scenario happened with me instead of the girl, and I told you that you could stay at my place, which is fine. Would you take it as a signal if I told you to lay in my bed with me because the guest T.V. didn't work?"
It's all about perspective. His fantasy never told him that he may end up in this situation, so he ignored all signals that didn't align with his fantasy. Opportunities for sex pop up out of nowhere, and when you accidentally turn it down, only afterwards do you realize that you missed a sure thing.
Anyway, I would suggest having sex with the bigger girl. It will break your cycle, you can have good practice at getting used to the situation. I STILL have a hard time coping with the awkwardness of sex for the first time with someone. Two nights ago I got this smoking hot girl in bed. It was a sure thing way before it even started, I knew there would be no resistance, I knew what was going to happen. . . But it was still awkward, it's hard to explain. Once I get going, it's no problem, but the initial buildup still gets me.
Having sex with a girl below your standards will actually help you with something. See, the fat girls know that you are a 8 or 9, while you know they are a 4 or 5; so naturally you are going to be the attractive one, and they will work for your affection, and you will treat them like you don't give a shit, which you don't. You should keep this mentality for when you are bagging 8s, 9s, and 10s. If you're a virgin at 26, then I think getting an 8,9, or 10 in bed could possibly be too much for you. Not that you shouldn't try, I just think you could accidentally blow it. You'll be less likely to blow it with the girl below your standards. You'll break your virginity cycle, you'll enjoy the sex, and so will she.
I do fuck people below my standards when I need to. I tell myself that I'm doing them a favor, I'm their reward (I actually am, truly, no game involved), so I think of it like a humanitarian thing. . . I'm giving a 4 or 5 the gift of having her fantasy of being with an 8/9 for a night.
As for the escort. . . Don't do it for your first time, man! I have had sex with prostitutes before, but it was totally out of novelty. It doesn't make me better, I'm just saying that prostitute sex is not the way to improve your mentality towards the subject. It could actually harm you. Fact is, they are there for the money, and they don't give a fuck about you, and you know it. I'll tell you what will kill it for you: When she first shows up, she is going to be somewhat friendly but not really. She's going to get her money. As soon as you give her the money, she is going to turn into the nicest girl in the world. She is going to call you "honey" and "sweetie" a lot. She is going to act for you. This is disheartening. The problem is that you know her affection is not real, so all social dynamics are so off, it's not even funny.
I've enjoyed sex with prostitutes, but for me I am able to accept the social dynamic because my brain is used to how it should be, so I know what is real and what is not. I will tell you, that I'm able to flag the fakeness of the initial interaction, and on two occasions I've changed her faked pleasure into knowing she's enjoying the sex so much, she's glad she came to fuck me. I considered one time that she should be paying me, because she was enjoying it more than me! I wouldn't have been able to identify that if I hadn't had sex with plenty of girls before hand.
So yeah man, stay away from the prostitutes. If you want to do it later for fun and novelty, I'm not judging. But you really gotta naturally get a girl into bed first. Even if you are "practicing" on a few fat girls, I would say do that so you can really get your mind right with the situations that pop up. These girls will leave you so in control it'll blow your mind, and I really think it'll improve your game with who you really want to be with.
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