A
female
age
30-35,
anonymous
writes:This is a bit embarrassing but I have two male friends who I've been friends with for a long time and we spend a lot of time together. Sometimes I sleep over at either of their houses when we can't be bothered going to our own houses. They're both amazing friends. We even share a bed on occassion (to sleep). One is 28 the other is 32 and both very attractive and single. As am I. A few weekends ago we were in a bar and I was sat between them and we were drunk and being a bit flirty and I joked that I bet we could all have a wild time together. To which we all laughed and flirted some more. We went back to one of their houses like usual but we went to sleep because I was drunk and tired. Now we've all been talking on our group chat sober about wanting to have a threesome together. We are all really up for it. I'm not sure how to broach the situation? How to be safe while not killing the vibe. What positions work. I'm excited but nervous. I want to make sure everyone has a really good time.
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drunk, flirt, threesome Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, Honeypie + ♥, writes (21 November 2019):
 OP,
I don't think people are suggesting it might NOT be a good idea BECAUSE you are a woman.
But because fantasy is fantasy, reality is reality and reality RARELY measures up to fantasy.
We have had PLENTY of people writing to DC regretting doing this, mostly women. THUS you get the answers you have gotten.
It's your life, your choice.
A
female
reader, anonymous, writes (20 November 2019): Have you considered getting together and stuffing a turkey..instead of you.
That way you can keep the friendships clean.
And have a happy xmas.
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A
female
reader, anonymous, writes (19 November 2019): I'd never do this with anyone. It would devalue me as a person. Call me old fashioned but what's wrong with sex with one man? Any woman can feel special if she chooses to be a porn star but after the moment is gone, can you live with yourself? Two friendships will never be the same. Don't confuse fantasy and reality. The aftermath has consequences b
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A
female
reader, Andie's Thoughts  +, writes (19 November 2019):
 Oh, something to add:
http://www.dearcupid.org/question/i-initiated-a-threesome-with-a-guy-friend.html
http://www.dearcupid.org/question/im-married-but-starting-to-get-obsessed-with.html
http://www.dearcupid.org/question/we-had-a-threesome-things-went-wrong-and.html
http://www.dearcupid.org/question/a-threesome-with-my-wife-and-another-male.html
http://www.dearcupid.org/question/threesome-gone-wrong-and-i-feel-so-cheated.html
http://www.dearcupid.org/question/threesome-gone-terribly-wrongmy-husband-is-in-love.html
http://www.dearcupid.org/question/threesome-gone-wrong-hes-always-told-me-he.html
http://www.dearcupid.org/question/can-you-get-over-a-threesome-gone-wrong.html
Whilst most of the threesome posts are about married couples having threesomes, it still shows that reality doesn't live up to fantasy and emotions don't stay clear cut after threesomes.
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A
female
reader, anonymous, writes (19 November 2019): Op here. I'm surprised considering men see it as a normal fantasy to sleep with two women that a woman wanting the same fantasy with two men is so looked down on. I've had bfs in the past I think most of which had had threesomes previously. I guess it's one of those things that I didn't think it could become a reality. And rather than with strangers I figured with people I trust would be better. The men aren't interested in each other but say they like the voyeurism of it. Everything will be safe. No drink involved as we don't want it to be a total disaster. Agreed certain things I will not do. And for the sake of future relationships with other people none of us is wanting to advertise the fact. We've been friends a long time and until now haven't all three been single at the same time. But there's definetly always been an attraction.
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A
female
reader, Youcannotbeserious + ♥, writes (19 November 2019):
 The stuff of porn fantasy. Is this post real or a wind up? Everyone needs to decide for themselves. Leaving it there as I suspect the latter.
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A
female
reader, Honeypie + ♥, writes (18 November 2019):
I think mixing sex with friendships is a bad mistake, that you will regret.
Friends don't have sex. (generally speaking)
And like Aidan said, Fantasies are NOT reality, reality RARELY lives up to fantasies.
You CAN NOT "ensure" that everyone has a good time when it comes to sex. What you can ensure BEFORE you all get started is to have CLEAR boundaries for what you all are OK with and what is a total no-no.
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A
male
reader, no nonsense Aidan +, writes (18 November 2019):
You want to make sure everyone has a really good time? Good luck with that.
You’ll probably find that they get competitive with each other. You’ll probably find that one of them feels left out. You’ll probably find that you enjoy one of them more than the other. You’ll probably find that once you’ve crossed that boundary, both will want sex with you again and may not take the rejection well if you refuse.
If you want to put 2 friendships at risk, go ahead. But I’d say proceed with caution. Fantasies are sometimes best left as fantasies.
I wish you all the very best.
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A
male
reader, anonymous, writes (18 November 2019): Don’t want to sound sexist but have you thought about your reputation.
Most guys will be getting high 5’s at that bar after checking [X] Spit Roast Judy on their Bucket List.
Now my otherwise June Cleaver like wife wouldn’t care, but I do. She had a near 3 someone with an old boyfriend and his buddy , but chicken out – wish she hadn’t. But you’re single – tell the guys this is a hush hush thing. Hold a repeat performance over their heads. Ask about STD history.
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A
female
reader, anonymous, writes (18 November 2019): You are about to turn yourself into a human produce of sexual fantasy and you may find the reality to be far less appealing.
The worst kickback would be that the friendship is destroyed or that they just want a repeat performance until they tire of it.
And you, dear soul are worrying about will they enjoy it.
Redefining your friendship in this way could become a fast track route to your own unhappiness.
So I hope you will consider saying no.
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A
female
reader, Andie's Thoughts +, writes (18 November 2019):
Are they bi or will both only want to be with you?
Have you set out boundaries to avoid ruining the friendship?
Have you discussed what you all do and don’t want sexually?
Have you agreed on a safe word that means stop no matter what?
Have you confirmed that nobody has feelings for anyone else in the threesome, so they won’t get jealous or fall for anyone?
Where will it be done?
What will happen afterwards?
Are you all prepared for how this will change your friendship?
Will you have enough condoms and use them responsibly?
Have you all agreed that, for safety reasons, none of you can be drunk?
Positions can be worked out in the moment, but the above things MUST be agreed on by all three or it could go horribly wrong.
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