Dear Anonymous,

I think the answer is a definite no.

She Won't Enjoy It

You've said you will only enjoy a threesome if your girlfriend is enjoying it
too. She's not interested in being sexual with a woman, so how is she going to enjoy it?

If she's as insecure as you say, she'd be going into the experience with a whole pile of worries, on top of the fact that she doesn't want the experience itself, only the effect it would have on you. Inviting someone else into your bed is a pretty big step.

It Can Lead To Upset and Regret

I agree. I did it, but now I regret it.

Even if both partners are really up for it, it can backfire nastily. It looks like your girlfriend, as you said, would be doing this just for you to enjoy it. I am of the opinion that threeways are a really bad arrangement to introduce into a relationship, especially in terms of sex. It can lead to regrets, feeling upset that one did something one didn't really want or like, and feelings of resentment. Let's not even start on the feelings, wishes and needs of the potential third person involved!

Just Fantasize Together

Maybe, instead of taking this big step which could lead to serious problems for you both, you could explore the fantasy instead, without involving anyone else. Perhaps you could talk about what you would be doing if there were another woman there.

Give Her Reassurance

It also sounds like you need to reassure your girlfriend a bit, that despite your differences in sexual experience and boundaries, you like her for herself, and she doesn't have to engage in ay particular sexual practice to win your approval.

She might well be having a hard time with your previous history, feeling that she has to become a wild girl so that you won't get bored with her. Feeling pressured, even if the pressure is unintentional, is never a good background to any sexual act or relationship.

So, to summarize: in my opinion, to have a threesome when you know your girlfriend is not interested in sex with other people would be a really bad idea, and you might need to reassure her that you won't reject her if she doesn't live up to your wild past.

Good luck.

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