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Should I go for it or just pass?

7

7-inch

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So I met this one older guy on Grindr and we kept on exchanging a lot of messages for like 2 days, and then he told me he wants to meet up, but he's partnered and he has to let his partner know. I was totally OK with that, but the only problem was that his partner insisted on joining us while having sex and he's around my age whilst I only like being with older guys.

I had to tell the older guy that I won't be able to have a threesome when someone my age is included, and he replied saying that he won't be able to meet me.

A couple of days after, he said that he and his partner would like to casually meet me somewhere as he claimed that his partner would want to get to know me and if he feels safe enough around me, he'd let the older guy and I have sex without him. I know this sounds crooked on so many levels, but I just went with it and the younger guy actually said he wants to have sex with me and he's afraid that I might "steal" his partner.

I told the older guy that I won't be able to have sex with his partner no matter what the circumstances are, and then he started talking about us meeting secretly. I haven't yet gotten back to him, but I was wondering what would you guys think I should do.

The older man is pretty fucking hot (in my eyes at least) and I feel like we're gonna enjoy ourselves so much in bed.
 
It really depends.

For me, I know I wouldn't be comfortable aiding in someone cheating on their partner. In part because cheating is about not respecting another person's boundaries. And if they're not going to respect their partner's, I can't feel secure in them respecting mine.

But I've said this before, I don't think it's anyone else's responsibility to maintain other people's relationship. That's their job. It doesn't matter how much someone pursues the other person, it is their responsibility to say 'no.'

However, you need to evaluate if you're okay with hurting the younger guy. Because you're playing a role in something that would hurt them. And would it be acceptable for someone to do that to you, cheat on you? Because if not, you'd be a bit of a hypocrite.
 
I totally get your point.

It's just that at this part of relationship when a couple start meeting others to have sex with (at least to my understanding) it's a means to make cheating sound less harsh. I don't think they have a healthy relationship to begin with, which of course is sad, but then again you could very well sleep with someone while they have a partner and not tell you, so it's not objectively wrong to do that as the older guy is totally aware of what he's doing, and I'm not even the one texting him or asking him to find a way around.

He keeps texting me and he says that he knows that his partner does it with other people and they're at this point in the relationship where everything is falling apart. I actually explicitly told him I don't want to be the bad guy here, but he kept convincing me that it'll be a one time thing and it won't affect the already deteriorating relationship.
 
My first thought is 'What if you're being lied to?'
It's not as if there isn't some reason to be suspicious. They're trying to do stuff behind their partner's back after all. I mean, why not just break up if things are this bad in the relationship?

I'm primarily concerned about you. You seem to be looking for strings free sex, and this situation seems to have a lot of strings attached; just not in the typical sense. Consider what your expectations for this encounter are, if they match up with your expectations for any other encounter, if they DO differ why (Is it special pleading?), and does the situation you're entering seem to match those expectations?

I think it's worth noting, you haven't even DONE anything yet and you're already feeling some anxiety over the whole thing. This feeling may not subside after going through with having sex. Is the sex worth the price? Because if not, you ARE taking a gamble–that's fine–but it needs to factor into your expectations.
 
7-inch said:
So I met this one older guy on Grindr and we kept on exchanging a lot of messages for like 2 days, and then he told me he wants to meet up, but he's partnered and he has to let his partner know. I was totally OK with that, but the only problem was that his partner insisted on joining us while having sex and he's around my age whilst I only like being with older guys.

I had to tell the older guy that I won't be able to have a threesome when someone my age is included, and he replied saying that he won't be able to meet me.

A couple of days after, he said that he and his partner would like to casually meet me somewhere as he claimed that his partner would want to get to know me and if he feels safe enough around me, he'd let the older guy and I have sex without him. I know this sounds crooked on so many levels, but I just went with it and the younger guy actually said he wants to have sex with me and he's afraid that I might "steal" his partner.

I told the older guy that I won't be able to have sex with his partner no matter what the circumstances are, and then he started talking about us meeting secretly. I haven't yet gotten back to him, but I was wondering what would you guys think I should do.

The older man is pretty fucking hot (in my eyes at least) and I feel like we're gonna enjoy ourselves so much in bed.
Click to expand...

I know it sounds tempting and I have been in your shoes before. However, Keep in mind that if this man doesn't respect his partner--what makes you think that he'll respect you. Emotions are involved.
 
Just reading through the first couple of paragraphs of the opening post, it brings to mind the rule that "if it sounds too complicated, it probably is too complicated".

It's not worth the time and effort. There are plenty of other guys who don't come with this much baggage.
 
What's your gut telling you? Go with it or pass? Mine would tell me to pass, but we are, neither of us, the other. I have, however, one thing you do not: a hell of a lot more years of experience. Your curiosity (and other parts) are saying: "go for it." And likely you will. Let us know how that plays out.

A guy who's worried about you "stealing his lover" is not very secure, and the older lover is telling you the relationship is "already deteriorating." Why, then, is he concerned with what the younger partner thinks? And why, then, would he even present to you the condition that, in order for you to have sex with him, you must also have it with his lover?? If the relationship is deteriorating and he knows it's going to fail, why present a situation that will only add to the younger lover's dismay? And what "younger lover" worried about you "stealing his man" is awake enough to know that the relationship is on the rocks already? How can you steal (an absurd notion: Love cannot be stolen. It's Love. It's GIVING, not TAKING AWAY. Jeez.) something from him he has already lost (according to the older lover, anyway).
This is whacko on so many levels, but your curiosity is like a mole burrowing into the ground. So maybe, for you? Have the experience and learn from it. Just make sure you learn from it.
 
Thanks a lot everyone for your replies! I have read them long ago, but been too busy to get back to you.

Actually after what you guys said, I thought I should just block the guy and so I did.

I didn't have sex with him, and I feel good that I had made that decision.
 
Good. That was a lesson in itself, one of deception and betrayal. What is mind boggling is how common (in the sense of low morals) this is becoming nowadays. Wow. What a world. (I mean, here in the US.)
 
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