Me and my best friend of 15 years hooked up

My best friend and I have been friends for about 15 years. Growing up through middle school and high school we did everything together we basically lived at each others houses. Over the years we have grown apart we still talk every day but we both work now and have boyfriends. She broke up with her boyfriend about a week ago and has been asking me to sleep over I pushed it off up until the other night I knew i couldnt leave her alone she’s been so upset over it we all thought he was the one.

Her and I have never made out or hooked up in the past but we’ve been best friends most of our lives so we would sleep in the same bed both in our underwear cuddle and watch movies. When I got there the other night we wanted it to feel like old times (big tshirt underwear ice cream snacks sappy movies etc) before bed we layed up talking about her now ex bf and I wanting to be a good friend told her we need to hang out more do this more often and that I would make the time for her her whole mood changed she seemed ready to move on.

So I rolled over curled up and wanted to text my boyfriend before going to bed shortly after my friend rolled over and cuddled up behind me which was normal what wasn’t normal was I could feel the top of her hand pushing into my butt slightly moving up and down as I layed there wide eyed thinking maybe she was sleeping? I decided to roll around and yes she was wide awake before I could say anything she started kissing me without thinking I kissed her back she stuck her hand down the front of my underwear it felt amazing I lightly rubbed hers on the outside of her underwear until we both came.

The next morning we hooked up again this time it felt natural she ended up going down on me like no one has before it was amazing I loved it but can’t help now but think about my boyfriend as I lay here next to him sleeping. If I hide it from my boyfriend and he finds out he will be so mad if I tell him I’m not sure how he would feel he has always joked and asked for three somes but idk how he’d feel knowing I did without him especially my best friend. Please help I know I screwed up and I’m not sure what to do now :( ... has anyone had a friend join you and your partner? I have thought about maybe letting my friend join me and my boyfriend but Idk how I would feel about him touching her maybe if she could just touch me?

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Based on 25 votes (19 yes)
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Comments ( 18 )
  • windyleave

    I don't know what's going on with everybody lately, but this is exactly the kind of thing that I can't wrap my head around. It's obviously going to bring harm to the relationship sooner or later, it's going to create suffering in both of you. I disagree with the comment above that monogamy is an outdated concept, I think you couldn't be any more wrong. Monogamy is the foundation of true love in my opinion, it's the highest expression of fidelity and compromise and I don't see why anyone would want to share their bodies like that with someone who isn't the one they truly love, or enjoy that their loved one does so. It would hurt me so much and I couldn't tolerate it if that were to happen to me.
    However, in your specific case I see you don't quite share the same values as me, which is perfectly fine, and as you say your boyfriend may be into threesomes and that kind of thing, so... What I can say is that if you have the absolute certainty that he is only devoted to you and loves you with his heart and soul and he would ONLY enjoy that kind of sexual activity as something unimportant to your overall relationship, I'd suggest that you tell him with regret and depending on his reaction maybe suggest that you make of this an agreed on subject if you want to continue with it. With that being said, I can't leave without stating that what you and your friend did, very, very bad indeed. Interested in it or not, you absolutely broke his trust and didn't even care about him for a second while you were at it and you should be very ashamed of yourself and beg for his forgiveness, and your friend doesn't care at all about you. She didn't think about your relationship (and to you), the damage this could do to it, about breaking your boyfriend's trust, nothing. She just wanted the pleasure of the moment and didn't care. Honestly, I know I can't force anyone to do something they don't want, of course, but I strongly suggest that you review your reasons to want to go on with that kind of sexually open relationship, would it make you happier? Would it add value to your life? To your relationship? If the answer is no, please reconsider your thoughts on monogamy. Also, please reconsider your friendship with that girl, because as I've said before, she didn't quite care about you when she did that.

    Best of luck.

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    • Thank you for your reply and yes i understand your concern me and my boyfriend are very much in love he would never go off and hook up with another girl and I would never hook up with another guy. But we have always been open to the idea of another girl joining us with restrictions and that’s why because it was a girl I didn’t think it was so so bad I know I should have told him before but everything happened so quick. Since then I have told my boyfriend and he agreed he wishes I had told him before but he thought it was pretty hot to hear about and immediately wanted to join in lol. Since then we have had my friend join our sex life again with restrictions he can touch grab and rub her boobs and butt but he can’t have sex with her and she can’t suck him off. The last time I let some things slide and she ended up rubbing him off while he ate me out it was actually a huge turn on watching another girl pleasure him with just her hands but I’m afraid to tell him that because I don’t want him wanting more lol. But again thank you for taking the time to reply if you have any questions let me know. Thx :)

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  • mlenny

    I really don't think it would bother him. Fuck, you could even invite him in if you're both okay with that. But I VERY much doubt he'd be upset with you about it. I picture the response being much more along the lines of "Can I watch next time?"

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    • Yea I don’t really think it would bother him either as long as I tell him asap. I wouldn’t mind having him watch but I don’t think I could let him fuck another girl especially my best friend or let her suck or rub him. I have the ass my friend has the boobs my boyfriend always comments on her boobs just to me so I know he will want to touch those. I’ll keep everyone posted

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  • A-sharp

    Another thing now that you had both experiences. Are you able to pin point the difference between another females touch, kiss vs a male ? ( just curious )..XOXOXOX.

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    • There’s nothing like my boyfriend kissing him is amazing she’s a lot smaller so it could have been that lol and it was pretty hot kissing her but I would much rather my boyfriend. As for pleasuring me they were both very different like I said my boyfriend is bigger has bigger hands face everything and lately he has been into ass play with me so the orgasm is much different. Buuut lol also her going down on me was like nothing I’ve ever felt like she knew me inside and out but they’re both very different I’d have to do a side by side comparisons lmao

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      • A-sharp

        "her going down on me was like nothing I’ve ever felt like she knew me inside and out" ...That's the $M dollar answer ( thumbs up baby) .. I hope the both taste you some day XOXOXOXOX..... Tell them A-sharp said: DO IT !!!

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  • A-sharp

    If you love him & want him to stay Don't tell him. The problem is people CAN'T KEEP THEIR MOUTH SHUT. Somethings are better unsaid.
    Enjoy your friend once a while if you liked it but keep that distance. Don't let her get use to tasting your pussy all the time. I think she's too close for a 3some but you want too set the rules at least until you know for sure everyone feels comfortable & won't go behind your back later on or make it a 1 time deal with her, that way you can then tell your husband later how shit started.

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  • MrToxic

    It sounds like you have an ultimatum. You either have to accept the idea of sharing your significant other with your best friend and vice-versa or you have to choose who you can see yourself continuing a relationship with. What you've done as of now is cheating. At the very least you owe your partner the truth.

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  • Fussmann

    I'd say broach the subject of threesome seriously. Mention her specifically. If he's into that, ask him if he'd be down to just watch at first. And if he's down for that too, and seems really into it, I'd bet you can tell him without any fear at all. He might even enjoy hearing about it.

    Personally, I wouldn't mind if my girlfriend had a female lover. It's obviously not a hunger I could ever satisfy, lacking tits or a pussy. Definitely prefer to be involved, for numerous reasons, but wouldn't mind too much either way.

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    • I don’t think I could ever watch him fuck another girl especially my best friend or even let her suck or rub him. I would rather him either just watch us or at most put a hand on her boobs or butt while fucking me

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      • Fussmann

        So you want to cuck him? Less likely to fly, but clearly I don't know him so who am I to say. Personally I just find that outlook selfish.

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        • Well I would want him to jerk off while watching us or I'll jerk him or suck his dick while me and my friend hook up. We all have hooked up a few times in the past month but I havent let him do anything more than touch my friends boobs and her butt I know he wants to tho I just don't know how to feel after

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  • Mammal-lover

    See monogamy is a broken concept. I would talk to him about it. If my significant other cheated on me I could possibly deal of they told me in a timely manner. But if I found out otherwise I would be pissed and all the trust would be gone. At the very least preserve some of the trust.

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    • I would never cheat with another guy this was my depressed best friend that just sort of happened and yes I’m leaning more towards telling him

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      • Mammal-lover

        It doesnt matter the gender of the person. You cheated plain and simple. This wasn't your best friend. You kissed her back and let things escalate

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  • my_life_my_way

    If you’ve never been with girls before, your boyfriend won’t suspect that you’re cheating with her. Just keep doing it and don’t get caught.

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    • Yes I know but me and him are very sexually active if he finds out in his own then he will be mad

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