Mailbag: Should I Tell My Boyfriend That I Used To Have His Cousin’s Penis Inside Me A Lot?

Jared Borislow8 years ago

The fact that people solicit me for genuine advice just because I write for TFM baffles me. Don’t get me wrong — I’m flattered, and I love helping you guys out, but what is it that qualifies me to serve as your ad-hoc life coach? I’ve gone in-depth, on multiple occasions, about how gross and despicable I am, so I’m not too sure why my guidance is considered to hold any merit. That’s the power of the internet for you. It can turn an average guy with an age of 23 and a BMI of 27.4 into Dr. Phil.

Lay it on me, mysterious stranger. I’m here for you.

Names have been changed for anonymity purposes

Hi, I’m Carrie and I’m 23 and I have a problem. I have never asked for advice and I’m a little bias in the fact that I prefer tsm but they can’t help me with this. I saw your advice on the lesbian sex story so I thought why not write.

I have been dating this guy, let’s call him Jim, for close to a year now. We met after I graduated college and moved to a new city for my new job. Anyway, everything has been great. We get along, sex is good and I see a future with this guy. At least I did, until a couple of days ago. Jim has this cousin named Peter. They’re practically brothers and grew up together. Up until a few days ago, I had never met Peter. Peter is unconventional and he decided to go backpacking around the world for a year. Jim showed me a few pics of him but it was always him in a group and if he was alone, it was kind of hard to see his face since he has this big beard and his hair is like shoulder length. When I saw the pics, Peter looked familiar but I thought it was a coincidence since I knew a Peter but the one I knew was always clean shaven and got haircuts religiously.

Last week, Jim told me that Peter was back and he wanted me to meet him. I was up for it since Peter’s one of the most important people in his life and I wanted him to like me. We met Peter at a bar and his beard was now gone but even with the long hair, I realized that I knew this guy. I didn’t just know him. I have fucked him. This isn’t just a simple fling, where we hooked up a couple of times. For my first two years of college, I hooked up with this guy alone. Everything I know about sex, I know because of him. Peter was my first everything: virginity, anal, oral, everything. The trick I do with my tongue that drives my boyfriend crazy, Peter and I saw it in a porn video and I practiced it on him till I mastered it. I mean, I have literally had this guy’s cum on my face multiple times. He has pics and videos of me, doing things that I can’t even type out, that I let him keep. And the thing is, we ended on good terms. Peter really helped me love sex and just be comfortable trying new things and it’s the reason my sex life is so good now.

Anyway, as soon as I saw Peter at the bar, his face just showed he recognized me. I played it off and acted like I didn’t know him and he followed along. A week later, Jim has a little party at his house and Peter was there. He pulled me aside and told me that he wasn’t comfortable lying to his cousin, and that he deleted everything he still had of me but that one of us would have to tell him. I know I’m so fucked. Jim is going to flip out when he realizes that I knew Peter and didn’t tell him. Most guys wouldn’t be okay with this situation and I don’t want to lie to Jim. He’s a good guy and he doesn’t deserve this but I love him. I really do and losing him would destroy me.

So basically, I’m asking for a guy’s perspective. Should I tell Jim and hope for the best? Should I just break up with him and not tell him why? I think if I tell him and he stays with me, it’s going to bother him and it will change our relationship, especially since Peter and him are so close. I’m leaning towards just breaking up with him, even though I really don’t want to, because I don’t want his opinion of me to change and I don’t want to fuck up the relationship with him and his cousin. Would you stay with me if you were Jim? Thanks for the advice.

Nobody wins in this situation. If you tell Jim the truth, there’s a chance he never looks at you the same way again, depending on how jealous of a dude he is. But if don’t tell Jim, and he finds out you and his cousin used to bang and neither of you guys ever told him, he might never trust either of you again — which is much worse, in my opinion.

Question answering time:

Should I tell Jim and hope for the best?

Yup. It’s not like you did anything wrong. You used to bang this dude before you even knew Jim was a person. Him getting mad at you for that would be like me getting mad at a dog I bought for having a previous owner. On second thought, that sounds wildly misogynistic, but you get what I mean. Anything that affects Jim that you did before you knew he existed was clearly not done with malice. You definitely hurt your cause by not telling Jim about you and Peter right away — if you had, you’d be in the clear — but you can still hopefully salvage this situation.

Should I just break up with him and not tell him why?

Definitely not, for two reasons.

1. That’s the worst way you could ever end a relationship. If you do that, Jim will always wonder what is wrong with him since you won’t have given him an answer.

2. Just kidding, he would wonder it for maybe two hours before he talked to his best friend Peter who’d spill the beans (which, from how you make it sound, he’s probably going to do anyways) and then you will have broken up with Jim for no reason.

I think if I tell him and he stays with me, it’s going to bother him and it will change our relationship, especially since Peter and him are so close. I’m leaning towards just breaking up with him, even though I really don’t want to, because I don’t want his opinion of me to change and I don’t want to fuck up the relationship with him and his cousin. Would you stay with me if you were Jim?

Unless Jim has banged one of your friends/family members as collateral, you’re right. He will be bothered by it. But if he’s a good dude, it won’t change your relationship. All he has to do is keep reminding himself that you didn’t do anything with malice aforethought, and that if he gets mad at you for it, then he’s the only person in the wrong. I’d stay with you if I were Jim, but if I were Jim, you wouldn’t be with me in the first place. Trust me.

And remember, if you tell Jim, which you should, you run the risk of him asking for a threesome. This is the second time in a row I’ve given this advice, but that’s just because it’s very good advice. You’ve been warned..

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