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I'm giving my girlfriend her fantasy to be with a former lover/friend. Will I regret it?

Tagged as: Sex, Three is a crowd, Trust issues<< Previous question   Next question >>
Question - (31 January 2011) 13 Answers - (Newest, 1 February 2011)
A male United States age , *penmindedandinlove writes:

I would appreciate any help and comments on my situation.

I met a wonderful woman last year and we had an immediate connection. Stronger than any I've known before and she said the same thing.

On our third date we were talking openly about fantasies and she told me of her fantasy to be in a threesome with two men. I told her some of my fantasies and that I'd love to share in hers. A months or so went by and the subject came up again. By this time we were deeply in love and I told her it was ok with me and I would love to help her fulfill this fantasy. She said she would like to ask a former friend/lover of hers since she was comfortable with him and they were good friends, to join us in the bedroom. I said that sounded good since she knows and trusts him and would rather have him make love to her than a stranger that we find online or somewhere else that we hardly knew. She told him and he said he would be happy to join us and is scheduled to come here in a week.

My questions is this; is it best to have a former lover of hers join us and let her have her way with him and him fulfill her needs sexually or should I suggest that we find someone that she has no former ties with? I know fantasies feel differently once they become a reality, but I love her and want her to have this. I also think it could lead to she and I having more fun and making some friends for occasional fun too and it will open up the possibilities for her to help me make some of my fantasies a reality. I know she loves me and does not love him other than as a friend, but I'm wondering how I'll feel afterwards?She's told me that he makes her feel good, makes her come several times and he does as well and that he is a little better endowed and has better stamina than I do. Also, I asked her to tell me how she sees it unfolding in her imagination, and she mentioned him screwing her several times while she plays with but said nothing about me screwing her while he's there. I'm not really jealous. I just don't want to have any weird feelings while he and her are having their way with each other, or afterwards.

Thanks in advance.

View related questions: jealous, threesome

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A female reader, celtic_tiger United Kingdom +, writes (1 February 2011):

celtic_tiger agony aunt"She could have just gone to see him without telling me, right? But then it wouldn't have been a threesome with two men she feels strongly about, would it?"

No, then it would have been called "cheating".

What she wants to do is screw him. By having a "threesome" she is doing it with your permission, so she cannot be accused of being unfaithful.

I suspect if you wanted to do this to another woman, she would probably have a different attitude.

If you love someone that much, as you proclaim she loves you, then you could never imagine wanting to be with anyone else, and that includes having sex with other men. If you are so deeply attached to someone then you wouldnt want another man touching you.

Just a question - what would you do if after this experience she then continued to have sex with this guy, without you?

What if she then decides actually, I want to be with this other guy instead?

You have obviously made your mind up, I just hope you do not live to regret your rose coloured view of group sex.

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A male reader, openmindedandinlove United States +, writes (1 February 2011):

openmindedandinlove is verified as being by the original poster of the question

openmindedandinlove agony auntAs I said, I have accepted that he might be better at screwing than me. There are many that are better than me and many that are worse. She's told me many times that I make her feel in ways she's never experienced too. I am an excellent lover and very passionate about it. Since we are very much in love, that love shows and comes from my heart. She feels it. I feel hers. This former FWB (friend with benefits as she calls him) has more stamina than I do and a slightly larger cock.

If I have issues about another man having a bigger cock and having more stamina, what kind of person am I? I don't have any or I wouldn't give him and her my blessing to screw each other. And if I did have issues about it, that's an entirely different thing unrelated to having a threesome.

I find it hard to believe, but not surprising, I guess, that so many write about him being larger and better in bed as a problem for me. I think this shows the poster's insecurity on the subject.

Why do I want her to have a former FWB knowing he can make her feel things I might not be able to give her? BECAUSE I LOVE HER THAT MUCH! Geez, is that so difficult to grasp?

How many women want a better lover in bed, but don't want to divorce their husbands? Yeah, millions most likely. How many men can accept another man has a bigger cock and is better in bed? Not many. What is the real issue? Should I accept the "norm" and stop this from happening because I might not be able to have healthy, mature feelings about it afterwards and be man enough and secure enough within myself to keep jealous emotions out of it? Or, should I go with my beliefs, that society coddles and actually promotes unhealthy attitudes, rise above this childish bullshit and let her have all the pleasure she can stand? She's a woman, after all, and adult woman, we're not married (which wouldn't matter to me if we were) and she as well as I, have a right to do with our bodies and minds and hearts what we choose. That's where trust comes in. I trust that she has her heart in the right place, and me in mind foremost in it. Her body is hers, not mine to control, dominate, rule over or condemn her for how she chooses to use it. Will her body be different after he screws her silly? No. Will her mind? Yes! She will be happy and content beyond what I can give her. GREAT! That's what I want for her and for me, should the time come and opportunity present itself, I will do the same with her blessing.

I should have worded my original question better. I'm not concerned about having regrets about letting her have this pleasure of the body and mind. I wanted advice on how I can be a mature, loving, secure man and not let human emotions and ego play any part in this. I also hoped some with experience could chime in and tell me how to make this as fun as possible for all of us, but that's not happening here.

Seems all her are doom and gloom, take no risk, play it safe, conservative and unexperienced to boot, but not shy about expressing their opinion none-the-less.

No disrespect meant. Just my opinions. One thing the replies have shown me, she and I are not "normal". GREAT! We don't want to be. She and I are mature and love each other unconditionally. She, after all, has agreed to let me do what I want with whomever, knowing that I will also not be reckless and stupid and choose wisely as she has done for her first experience. And she chose me to love and asked me to share this with her. Regardless of how good this guy makes her feel, regardless of how enthralled she gets in the throws of passion, I know I'll be happy for her to have had this long-time fantasy fulfilled and even more happy that she asked me permission to do it and to share in it.

She could have just gone to see him without telling me, right? But then it wouldn't have been a threesome with two men she feels strongly about, would it?

Hey, thanks to all for taking the time to share! I will definitely write a post-threesome report about how it went, how it made me feel, how she tells me she felt, and where she and I plan to go from there.

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A male reader, openmindedandinlove United States +, writes (1 February 2011):

openmindedandinlove is verified as being by the original poster of the question

openmindedandinlove agony auntAs I said, I have accepted that he might be better at screwing than me. There are many that are better than me and many that are worse. She's told me many times that I make her feel in ways she's never experienced too. I am an excellent lover and very passionate about it. Since we are very much in love, that love shows and comes from my heart. She feels it. I feel hers. This former FWB (friend with benefits as she calls him) has more stamina than I do and a slightly larger cock.

If I have issues about another man having a bigger cock and having more stamina, what kind of person am I? I don't have any or I wouldn't give him and her my blessing to screw each other. And if I did have issues about it, that's an entirely different thing unrelated to having a threesome.

I find it hard to believe, but not surprising, I guess, that so many write about him being larger and better in bed as a problem for me. I think this shows the poster's insecurity on the subject.

Why do I want her to have a former FWB knowing he can make her feel things I might not be able to give her? BECAUSE I LOVE HER THAT MUCH! Geez, is that so difficult to grasp?

How many women want a better lover in bed, but don't want to divorce their husbands? Yeah, millions most likely. How many men can accept another man has a bigger cock and is better in bed? Not many. What is the real issue? Should I accept the "norm" and stop this from happening because I might not be able to have healthy, mature feelings about it afterwards and be man enough and secure enough within myself to keep jealous emotions out of it? Or, should I go with my beliefs, that society coddles and actually promotes unhealthy attitudes, rise above this childish bullshit and let her have all the pleasure she can stand? She's a woman, after all, and adult woman, we're not married (which wouldn't matter to me if we were) and she as well as I, have a right to do with our bodies and minds and hearts what we choose. That's where trust comes in. I trust that she has her heart in the right place, and me in mind foremost in it. Her body is hers, not mine to control, dominate, rule over or condemn her for how she chooses to use it. Will her body be different after he screws her silly? No. Will her mind? Yes! She will be happy and content beyond what I can give her. GREAT! That's what I want for her and for me, should the time come and opportunity present itself, I will do the same with her blessing.

I should have worded my original question better. I'm not concerned about having regrets about letting her have this pleasure of the body and mind. I wanted advice on how I can be a mature, loving, secure man and not let human emotions and ego play any part in this. I also hoped some with experience could chime in and tell me how to make this as fun as possible for all of us, but that's not happening here.

Seems all her are doom and gloom, take no risk, play it safe, conservative and unexperienced to boot, but not shy about expressing their opinion none-the-less.

No disrespect meant. Just my opinions. One thing the replies have shown me, she and I are not "normal". GREAT! We don't want to be. She and I are mature and love each other unconditionally. She, after all, has agreed to let me do what I want with whomever, knowing that I will also not be reckless and stupid and choose wisely as she has done for her first experience. And she chose me to love and asked me to share this with her. Regardless of how good this guy makes her feel, regardless of how enthralled she gets in the throws of passion, I know I'll be happy for her to have had this long-time fantasy fulfilled and even more happy that she asked me permission to do it and to share in it.

She could have just gone to see him without telling me, right? But then it wouldn't have been a threesome with two men she feels strongly about, would it?

Hey, thanks to all for taking the time to share! I will definitely write a post-threesome report about how it went, how it made me feel, how she tells me she felt, and where she and I plan to go from there.

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A male reader, Capri2 Argentina +, writes (1 February 2011):

You and your girlfriend seem pretty sure about doing it. I think that's why you should do it. But you asked how will you feel afterwards. And we don't have even the roughest idea. But you already know two things can happen.

You can come to enjoy the whole thing, feel comfortable with the group sex and everybody will be happy.

Or, you can come to see that this guy is better in bed than you. What would happen if they start having sex and you see her enjoying in some way she have never enjoyed with you?

Well, I guess the only way to find out is doing it.

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A female reader, eyeswideopen United States +, writes (1 February 2011):

eyeswideopen agony auntLook in the archives, we've received hundreds and hundreds of posting from participants of threesomes asking how they can recover from the devastation their poor judgment has caused. Let us know how yours turns out.

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A female reader, angelDlite United Kingdom +, writes (1 February 2011):

angelDlite agony aunthave you done threesomes before? i just don't know why you are putting your self to this mad test of trying to prove to yourself that you can suppress your jealousy. i mean .. just .. why..? to what end? prove your mental/emotional strength or something?

as you say, it is scheduled so no one is gonna or is trying to talk you out of it, you post seems to be asking though is it preferable to have her hot, well endowed ex involved, who is obviously not likely to fail to please her or would it be better to have some randomer from the internet, and now you tell us that hot ex has got his ticket and probably his luggage packed already too?? and you don't want to feel weird, it sounds like you are expecting to feel weird though (?)

i agree with you that it would be useful to speak to someone who has been in the same situation and ask them how did they cope with the after effects of watching their beloved partner having great sex with their ex.

i have never had a threesome, not a prude or anything but that just 'isn't my thing' BUT if i was going to do this it would be within a more casual fling, and NOT with someone i am in love with, coz i HAVEN'T got the emotional strength for it, i don't mind admitting it to you and i have no wish to go out of my zone to find it. that's just my opinion though. maybe small minded(?)

when this episode is over, is there any plan for a threesome- your partner, you and a woman of your choice?

x

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A male reader, openmindedandinlove United States +, writes (31 January 2011):

openmindedandinlove is verified as being by the original poster of the question

openmindedandinlove agony auntI just want to add a little more to what I should have included in my original post. This is going to happen, it's already scheduled, her former lover has airfare, I've talked with him about this and she and I have decided to move forward after weighing all the pros and cons. WE DECIDED, not just her. Sorry if outsiders can't believe that it's a mutual decision and if one is not on board, it won't happen. Nay-sayers will always take the negative, less risky, less rewarding road, so no offense taken.

In many ways, this is my fantasy too. Not the least of which will be two of us men will be making love to and pleasing one sexy, very talented woman. But also that she and I will share this very intimate experience with each other AND someone that has been a good friend to her over the years, showing once again, that our love contains no jealousies, that I value her and her past and accept her for what she is and what she has lived before meeting me. And yes, not being jealous is a challenge for me and would be for any man, I admit it. It will be difficult to not be jealous and put my ego aside. Ego, by the way, is the root of all evil, not money or fame or pride or jealousy or envy...

But in the end, once I have shown her and more importantly myself that I can keep the physical pleasures world and its pleasures of the flesh separate from our love and commitment for one another, I will have grown beyond anything I could have imagined before meeting her. So, she is actually sharing in my fantasy, to be a better man, one that does not judge by worldly standards or need to possess and control his mate. I wager that most men would love to be in my shoes, knowing this wonderful woman will do for him and herself what she has not done for any other, and let him do whatever his heart desires without consequence. Therein lies the responsibility to not be reckless and cavalier about it. And that is the real reward to me. Overcoming my own fears, jealousies and society-based standards for someone I love. Ok, bring on the negative comments from those of you that have no experience in this at all.

I wish someone that was in or has been in my position with my goals would respond!

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A female reader, angelDlite United Kingdom +, writes (31 January 2011):

angelDlite agony aunthi

are you kidding me? you are already feeling jealous and it ain't even happened yet! you are clearly only doing this to make her happy, it is not for you really is it?? and she has TOLD you that he has better stamina and is bigger than you and it sounds like her fantasy just involves you standing around, waiting (a long time)for them to finish!

oh come on! no, pal, i don't think you are in for a fun night to be honest, but if you insist on going along i would suggest you take a crossword or sudoku book with you

xx

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A male reader, openmindedandinlove United States +, writes (31 January 2011):

openmindedandinlove is verified as being by the original poster of the question

openmindedandinlove agony auntShe and I talked about this at length. I plan to participate and told her my concerns of feeling left out. She said she wants it because there will be two of us, not just one, and I believe her. She also told me just today that if I wanted to change my mind, she would gladly keep this just a fantasy. Those replying to my post cannot possibly know her as I do, so I understand your doubting her and I'll just ignore it. I know she loves me. She's proven it many times since we met. I mainly want to get feedback from those that have been in this situation, experienced the emotions and dealt with it in a healthy, non-jealous, non-judgmental way.

I will probably be jealous to some degree, but my goal is to not express it, ever. I believe this will show that our relationship is not based on conditions, does not involve jealous, petty emotions in any way, and is stronger than any I've ever known. I've been in those where one or the other fantasizes and never gets it realized. What's the difference between actually doing something about fantasies or keeping them a secret desire? The difference is that keeping secret desires will destroy a relationship. Been there. It's also not fulfilling, very boring and lacks uninhibited sexual expression most of the time. I don't expect this is for everyone, but it is something she and I both want. And if I am man enough to admit I can't give her the same sexual release and joy, doesn't that say something about my character? Most are too immature to even admit it, much less do something other than be controlling and jealous. I will not deny her anymore than I want to be denied and wanting. Thanks for the replies none-the-less. Any that have been in this situation?

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A male reader, openmindedandinlove United States +, writes (31 January 2011):

openmindedandinlove is verified as being by the original poster of the question

openmindedandinlove agony auntWell, what good could come from it is she gets her long-time wish fulfilled, there are no petty, jealous emotions on my part, we share something very intimate and giving and we have an even stronger bond and prove that there are no jealousies involved in our relationship and our love is true and unconditional. That's pretty darn good, and rare, in my opinion. Of course, it could go the other way too, but denying her or myself what we truly want leaves the relationship as so many are...boring, unfulfilled and lacking true, uninhibited, sexual expression and more importantly, unconditional love. Been there. But thanks for the replies and look forward to more. Especially from some that have been in my situation.

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A female reader, celtic_tiger United Kingdom +, writes (31 January 2011):

celtic_tiger agony auntTo me, this sounds more like she wants to have sex with him and you just happen to be there, rather than a threesome.

I think you will end up feeling left out, confused and lost. She has already told you this guy makes her come more, is bigger than you, and is generally better at satisfying her than you.

She wants to have sex with him. Not having sex with YOU AND HIM.

I would never consider a threesome because it is essentially cheating with permission. To my mind its wrong and if you love someone you wouldnt want to make them feel small and disrespected by screwing someone else whilst they watch. Thats just mean.

From all the questions I have read on here about threesomes and making fantasy into reality 90% do not work out, and jealousy, paranoia and cheating sets in. Often with one party getting majorly jealous, the other not understanding, and usually results in the relationship ending. They just dont work.

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A female reader, Honeypie United States + , writes (31 January 2011):

Honeypie agony auntI don't see anything good coming from fulfilling this particular fantasy, sorry.

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A female reader, eyeswideopen United States +, writes (31 January 2011):

eyeswideopen agony auntOh brother, I hope the fantasies you want fulfilled are truly worth this and more importantly are really going to result from this threesome. What happens if you can't handle this and you guys break up over it...what a waste.

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