So I've been fucking this girl, 19, quite hot, but I want to push her over to my roommate, who's quite bad with women in general, and has a bit of a crush on her. I don't mind, since I've never been too into her and he's one of my best pals. Guy needs some pussy soon too, still a virgin and nearing his mid-20s.

A bit about her personality: She is pretty shy and pretty much a push-over. Not alot of sexual experience but I got the kinky out of her quite nicely. She's pretty into me, but knows that nothing serious is ever gonna happen. She tried to "quit" our thing a couple of times, but I haven't had any trouble getting her into bed again. She's one of those girls who tells you all sort of shit about how she never does "things ,like that" and isn't sure if she wants to do this and that and still ends up doing whatever you pressure her into. You know the type.

So far she doesn't seem to have a thing for my pal. But I've a feeling it's still gonna be easier to get him laid with her, than with cold approach. Guy has some serious social anxiety and is amazingly uncomfortable around women. I pushed him into trying to kc her during New Years Eve and he fucked it up big time (way too drunk and just really nervous and shit). But I think I can still salvage that.
My gameplan: I've been uptalking my guy in subtle ways and insinuated that I might be jealous if they were to hook up. The idea is that I go out with them and fuck off with another girl, making the first one jealous and therefore more receptive to him. She thinks she might get my attention if she hooks up with him and he is pretty much in.
Whats your guys opinion on that plan? I know it's kind of a convulated way to get him laid, but the guy is really far behind in terms of getting women, and I'm no master PUA myself.

Won't work. Your friend is socially awkward. At most he will be the shoulder she will cry on.

It's a pretty fucked up way to treat her. If you want to pass her around amongst friends, you should let it be her choice and not manipulate her. There are women out there that are willing.

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Well, it's the best shot he has right now. And I really think getting some experience will accelerate his progress by alot. Alright, it sounded way worse than it was in real life. I was always upfront with her, I gave her enough chances not to sleep with me and I talked with her about the whole thing way more than a fuckbuddy should. I don't think it's my fault if she keeps coming back for more. She's a grown woman, I really think, as long as youre being upfront and honest, I should be able to play game on her. And jealousy is part of game, why should I not use it, even if it's not for me.

Hey man.
To be honest, if he is really awkward and shy, it can fuck him more than do good in my opinion.
Even though, from personal experience, the best way is to bring him in when you are in the middle of having sex.
say something like "hey, my roommate know how to please a woman the best way possible!" and then call him, but in a playful voice.
(it would help also if you are like trying to do something to her and make a bad job lol...)
when he enter the room be like "oh fuck...LOL he is here..." laughing about it. (like you didn't expect it)

but-you need to calibrate and see how your girl reacts to even the idea. I had girls who would flinch just by hearing somebody walking outside the room...


In my experience, girls are much much more prone to 3somes than you might think. LOL... your chances of getting him in are much higher with you around.

But again-it can really fuck him up if you do it the wrong way...you don't know his mental state so if he is a virgin i would advice against it (:

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Why dont you just ask her to fuck him ? lol or is that too upfront and im missing the point ? I've asked a few girls to fuck my mates one nights out and its worked a few times lol !

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That's like asking why I don't go to every girl and ask her if she wants to fuck me. Sure, maybe 1 out of a 100 might say yes. But I think the odds aren't that great.

Not atall actually. I'm not daft lol. You clearly have some kind of connection to this girl if shes willing to fuck you therefore being up front and honest may work in your favour instead of manipulation.

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Btw. The two of them got together in the end, and now I lost my wingman. Thats what you get for helping a brother out.

What happened?

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So at first I told him to meet up with her and they did and he finally got around kiss closing her, and even slept over at her place (no sex though). But the next day she told him she only wants to be friends with him. He was pretty hurt, but I told him to play it cool and he froze her out for a while. Since I am kind of friends with her and they liked each other before too, she also didn't take the whole thing too lightly and me and her kept in touch through out. A couple of days later when my pal and me went out I "drunk texted" her and told her, that he was having a grand time and insinuated that he was making out with another girl.

As I had hoped she got second thoughts about the thing and a couple of days later she wanted to meet him again, but I told him to blow it off, which he did. All the while I was texting with her, and subtly notching her in his direction. I was kind of her go to guy, to talk about the whole thing. So I used that to give him some value and get her thinking that he actually might be the right guy after all.
Anyway, long story short, in the end he got her. And I definitely need to give him some credit, it's not like I manufactored the whole thing. But I notched them both in the right direction. Unfortunatly I got nothing good out of the whole thing. Motherfucker is happily in love and has forgotten all about me.
I mean I'm happy for him, it's cool that he finally got a GF and laid and everything, but I swear to god, the second he smelled some pussy he forgot about everything else. 10 yrs friendship mean nothing as soon as you find the right pussy. All our goals about pushing each other and that stuff, forgotten in an instance. Not that I can really blame him, I mean I know what I was like when I started having sex regularly.

Shit, dude, you're a phenomenal wingman.

You should've expected this to happen though. Can't really blame the guy, we've all been in his shoes at some point. You should probably smack him over the head a few times and don't let him invest so much.

Eventually he'll suffocate her and it won't end well for him.

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I know my place. It's me on top of the world.

My in depth texting & dating guide.
There's no such thing as shit-tests.
How to keep a girl.

Thanks man, I'm really proud of it too. I mean they are both pretty happy. She got treated pretty poorly by guys in the past, and my guy is a solid dude, so it worked out well for both of them. I got to admit, on some level I want him to just get it out of his system and move on. And I was pretty pissed off that he forgot about all our stuff so fast. But yeah, as you said, what else did I think was gonna happen? I mean we are both close to our mid-20s but he had no prior experience with girls, so for him it's probably more like it was for us in our teens. I mean I've been sexually active for almost a decade now. A decent number of girls, a big LTR that ended badly, so of course I'm far more jaded. I guess he just needs to experience all the ups and downs himself. Better late than never.

Bad thing was this was a chick you had slept with multiple times and who likes/liked you so both of them probably aren't gonna want to be around you. Doubt this guy will be fine hanging with the guy who was fucking his girl and who she may still like. Have you tried hanging out with him?

Exactly. The whole experience is amplified for him since it's so late.

_________________
I know my place. It's me on top of the world.

My in depth texting & dating guide.
There's no such thing as shit-tests.
How to keep a girl.

Oh yeah, I forgot to mention, he is my flat mate.
What happened was, she actually wanted to hang out with him and me and I told her that I'm not gonna be their third or fifth wheel or whatever. At first he didn't want me too close to her anyway, cause of her previous crush on me, but I think that's fine by now. They are pretty solid, so I don't think he sees me as a threat or anything, especially since I made it pretty clear I wasn't into her (honestly I just fucked her because she is hot and I could, not because I was particularly attracted).
Mostly I was being kind of dickish, cause I didn't want her around. And he feels more comfortable with me not being around too, for obvious reasons, so most of the time he is at her place. She was at our place once but I stayed at my room.
I was pretty restistant about hanging around with her, cause I mean, who wants to hang out with a former fuckbuddy and watch her messing around with your pal. Even though I don't have any feelings towards her, that's just not something that sounds too appealing. But yeah, I am warming up to the idea of her being part of our social circle. But all in all, I've got to say, I didn't benefit at all from the whole thing. I mean, she threw a party a couple of weeks ago, where I made out with one of her friends, so I guess that's at least some consolation. But I already told her, she owes me at least one lay with a hot friend of hers.

Oh yeah, another thing that pissed me off hugely is when he started telling her, about my sex life. A couple of weeks back I fucked a 17 year old and I really didn't need him to tell her something like that. Also I'm pretty sure he told her about most of what I did to notch her in his direction, which is stupid as well as dickish if you ask me. Really smart move to tell your girlfriend of like a week, how you and your best friend manipulated her into getting together with you.