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Need tips, advice, etc. from those experienced with threesomes. Planning one soon with my girlfriend and her former sex partner.

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Question - (1 February 2011) 22 Answers - (Newest, 2 February 2011)
A male United States age , *penmindedandinlove writes:

Ok let me try this again. My other questions wasn't worded like it should have been.

I'm having a threesome with my girlfriend and have given her approval to have a former friend/lover (not as in love, but as in having had sex with him before she and I met) be the third. She and I are very much in love and have agreed to share in each other's fantasies, starting with her threesome fantasy first. We've talked at length about how we feel about each other and how she feels about him, which is just as a good friend. I have no problem with her lusting after him and him giving her the screwing of her life while I'm there watching and joining in as well.

So, I'm asking for any tips from those that have experienced threesomes with their partner and another man, or a woman that has done it with her man and another man. It's our first time together and I've had one before with a former partner that was lacking the fun I thought should be there. Mainly because I was younger and the guy was pretty much a total stranger and my partner at the time was not as sexy, talented and loving as my current one.

Anyone have experience and can share some tips, pitfalls, advice, whatever?

Thank!

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A male reader, openmindedandinlove United States +, writes (2 February 2011):

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

openmindedandinlove agony aunteyeswideopen, Now you feel the need to cast doubt on my post's validity? And you're happy about it too. Geez, you hurt my feelings. I just live for your approval and can't get it. sigh

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A female reader, eyeswideopen United States +, writes (2 February 2011):

eyeswideopen agony auntYou asked: "Anyone have experience and can share some tips, pitfalls, advice, whatever?" You got all of the above with both postings. Here's my positive answer: I'm positive you are going to regret this threesome, that is if this is a real post and not a wind up. Hey you are right, I DO feel better!

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A male reader, openmindedandinlove United States +, writes (2 February 2011):

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

openmindedandinlove agony auntcaptain, thanks for writing. Sorry things didn't work out for you and you ended up having your feelings hurt and feel cheated. I guess you should, you were cheated on and lied to, after all.

That's why my girl and I agreed to not see other people on our own. Actually, it was her idea and I agreed. Why be in a relationship at all if you're going to see people outside the relationship on your own. Might as well just stay single and date and be friends with benefits.

She and I will not become swingers. We're not interested in that lifestyle. When I was younger I thought about it, but never did it and won't now that I'm older. We agreed we will fulfill each others fantasies, or at least some of them as long as they don't hurt our relationship.

I'm giving her this one and letting her choose the guy because she is not a person to just sleep around with anyone. She knows this guy, she's good friends and they have had sex and enjoy pleasing each other and are satisfied with each others "technique" so to speak. Why should I insist on a stranger that would not be as satisfying? To deny her some amount of pleasure to try to make sure I don't lose her? Doesn't make sense. I want her to have all the pleasure she can stand and then some. That's the whole point of this fantasy. And it is a 3some and I guarantee you I will be participating most of the time. Like you, captain, I want to "see" her having her fun to so I plan to step back and watch a little too. She's a sexy, wonderful, sensual woman and I know seeing her please another man and being pleased will only make happy too. After all, she asked me for approval and told me if I wasn't ok with it she would not do it, so my approval that she have as much fun as she can gives me joy too. She also trusts me and I trust her and I trust her friend. Anyone she trusts, I trust. It's just that simple and I wouldn't be in this relationship, madly in love with my soul-mate, best friend, lover and the woman I've dreamt of finding since I can remember dreaming if I wasn't sure that she and I could handle this without jealous issues or damage to our relationship. That's just one of the wonderful things we've found with each other. Unconditional love and best of friends. It just doesn't get any better. We're not doing this to improve our sex life. We have a great time every time we're alone together. I do not feel inadequate in any way with her. This is not about her finding something I can't give her, other than her fantasy of a 3some involves another man. I can't be two men at the same time. So, here we go!

Best of luck to you captain and I appreciate you taking the time to write a detailed reply. All the best to you and yours!

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A male reader, captain South Africa +, writes (2 February 2011):

It seems that you are not getting the answers for the questions that you are asking. I hope that my answer will help you. I was in the same boat a few years back. maybe not 100% the same but more or less.

My wife and I were maried for almost 3 years and desided to spice things up. Our fantacies was much the same as yours. We had it as a fantacy for more than a year before we desided to react on it. The diferance was that she wanted to have sex with a former lover as in "lover". I loved and trusted my wife and agreed to it.

She contacted him and he agreed to it under one condition that I was not happy with but went along with it because she was happy with this condition.

The condition was that since he would feel uncomfortable with me being her husbend and him being her former lover he wanted to first have sex with her alone. Not as a three some but just the two of them. He also did not want to do it at our house but at a motel. After we discust it we desided to go ahead with the arangements. I have never met this man before and as time got closer I was going out of my mind with worries. What if they fall in love again and so on. I did not want to make her feel uncomfortable so I never told her about my fears.

I did tell her that it would make me feal more comfortable if I was informed of everything as it went along and if she felt uncomfortable at any time she should pull out and contact me imedieatly.

As this was a turn on for me even thoug I was wouried I asked her to take some pictures of them having sex. This may seam sick to some people but it turned me on so I dont care what they think.

The day arived and I was so exited to know that it is finaly about to hapen and that she would be banged out of her mind that I was on a high the hole day long. Everything went acording to plan and she came home a very happy women. I was just as happy and could not wait for her to tell me all about her experiance and for when they made the arangements to have the 3som.

It turnd out that the sex was not as good as what she rememerd it to be but she still enyoud the exitment of knowing I knew what she was donig and that I was okay with it. She had a blast and the pictures proofed it. I on the other hand never got to share this experiance with her as the former lover could not get it over himself to have a 3som with me included.

We had uncounteble 3soms and moresomes after that but I still wonder what it would have been like with him as he was a former lover. Whe became full on swingers and that lasted for mor that 4 years.

The only problem we had was that my wife could never get it over her heart to let me have sex with another women. This putt some strain on our relationship as I felt as a outsider. She would let me have sex with someone the she would choose but that would be once every couple of months. In the 4 years that we were swingers I had sex with 3 other women. All of them more than once but I did not have the freadom that she had.

This led to me having afairs behind her back as we were in it together but she got all the action and I got nothing.

She found out about my afairs and desided that we would swing no more. I later found out that she also had an afair behind my back and yes it is who you think it was with. Her former lover. They never stoped having sex. They were having more fun that what I could ever get from her. They had 3soms with her best friend. They had sex in public places to make it more exiting. They even had sex in our house without me knowing about it.

We love each other very much and we wanted fun!!!! But we almost lost each other. We are still together and still love each other but we do not swing anymore.

Up untill today I feal cheated out of a lot of fun but at least we still have each other.

So I hope that this answers your question. Now I must warn you even thoug I know you would not lisen to my advice. Rather not do it. At least not with the former sex partner. Make it exciting yes but rather keep it only a fantacy.

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A female reader, Miamine United Kingdom +, writes (2 February 2011):

Miamine agony auntSorry you don't like the advice given.

I have suggested you look for "swingers" websites where you will find what you need.

I have no problems with people's sexuality. But in your case, from what you have described, I think it's a very bad idea.

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A male reader, openmindedandinlove United States +, writes (2 February 2011):

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

openmindedandinlove agony auntWell, Gamine and Miamine, you could not be further off target, but thanks for your few kind words. Apparently, you don't believe what I've written about this girl (woman of 50 yrs young) or you just want to bash what you don't believe in.

That's ok too. It's your opinions and you have a right to them and to post them here. But, you really missed the mark, I have to tell you.

And, I am proud of myself, my girl, and everything we do together. It comes from a place of love and kindness and unselfishness. Can't say the same about some of your comments.

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A male reader, openmindedandinlove United States +, writes (2 February 2011):

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

openmindedandinlove agony auntHey, thank you very much angelDlite! What a nice reply. Yes, it's kind of like giving her a sex toy that's bigger than me (not by much and I think only a little thicker, which she enjoys!), but it's a live sex toy that is also a good friend of hers and she trusts him completely to not mess up our relationship. My girlfriend is not like anyone I've ever known, so I know it's hard for readers to understand what she and I have.

That's just a little of why I'm sure she will not want him as a boyfriend afterwards. That, and they have been friends for several years and not been a couple in love, only sex buddies occasionally during that time. So, why would she go to him after this? Doesn't make any sense at all.

I want her to have this, and anyone else she might want too. I know she has a good head on her shoulders and will not want to screw every guy she can, but if she has any others that she feels she trusts and would like to give her pleasure, that's fine with me too. I love this woman like you can't believe!

I will definitely write a follow-up once we've had this experience.

Thank you again, and everyone else for their replies!

Namaste

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

angelDlite agony aunthi again,

i am glad you have asked this question again coz i wanted to reply to your most recent follow up last time but the post is now blocked from further replies.. anyway.. i think i can understand a bit better were you are coming from (maybe?) its like a man buying his missus a sex toy for her birthday or something? he knows it will be bigger and last longer and make her cum more, BUT he also knows that she loves him and the sex toy will therefore never take his place in her heart. (or have i got this totally wrong?!) its the only thing i can liken it to, purely because i have never heard anyone express the thoughts and wishes that you are doing.

i wish you well and i hope that this experience is everything you want it to be. and if you can get overcome any weird or jealous feelings you might get; i think it would be good if you could maybe write an article afterwards, to share your knowledge and to help others get over insecurities about threesomes, partners exes, partners having affairs, any sort of sexual jealousy really

xx

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

Miamine agony auntThis Girl????? How old is this woman?

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

Miamine agony auntI've had one before with a former partner that was lacking the fun I thought should be there. Mainly because I was younger and the guy was pretty much a total stranger and my partner at the time was not as sexy, talented and loving as my current one. (openmindedandinlove)

Now your 51-59, it'll probably go wrong because the guy is younger and sexier. She'll spend all her time having sex with him, you'll get left out and probably will have problems with your erection.

You don't have the right attitude for a threesome. You didn't have much fun during the first time, and you won't have much fun this time. You'll find excuses, this time the man will be too young and your woman will be too sexy and eager. People who do threesomes can't afford jealousy and can't blame others for their own short comings.

Yes your open minded, but leave this to fantasy. This woman wants a certain man, that's bound to bring up bad feelings. Watching your woman get screwed by a man she fancies more than you is a very bad idea.

Consider someone a little less familiar to both of you if you really need to do this threesome thing. I bet she'll have problems. Sounds like she's more into the man, than she's into expanding her sexual boundaries.

Look for "swinging/swingers" on the internet. They provide rule/guide books for any combination of people over 3. They will tell you how to proceed in the safest way possible.

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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 auntThanks jmtmj! Funny, sad, informative and personal. Thanks for sharing.

To be honest, I also had my one previous threesome attempt go bad. I mentioned it briefly in my original post. Looking back I can see that it was doomed to be horrible. She (my ex-wife) was not the right woman for me. She was violent before we did anything. She was not passionate, giving, understanding and open minded. She WAS selfish and took advantage of the situation, broke every agreement we discussed prior, and lusted after the guy during and afterwards like a whore in heat. Ok, I'm really not bitter about it. I deserved it, I guess, if anyone deserves that kind of childish, selfish behavior. The guy was a stranger and therefore had no allegiance to either one of us, especially me and he took advantage of the situation too. I could have and should have thrown him out, but I let it go on because she and I were over before that and that just sealed the deal. Shortly afterwards I told her to hit the road.

Ok, sounds cliche, but this girl is different. VERY different. Our connection is VERY different. I won't go on because I know no one believes me, but that's ok. I know her and I know me and this is going to be a blast. Sure, it will be awkward at first, weird seeing her being pounded by another guy, kissed passionately, fondled, licked, nibbled, whatever. But that's what I want her to have because it's what she wants. It can only go wrong if I let jealousy overrule my common sense. It's only sex. I don't own her. I don't want to own her. I don't want to control her, or her me.

So, I'll be sure and post a follow-up with all the details and feelings afterwards and where we plan to go from there.

Thanks!

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A female reader, anonymous, writes (1 February 2011):

I asked an open question on this site once because I was interested in finding out how poeple felt afterwards. Every single on wished they had never done it and broke up with their partner. Be aware that you are introducing a risk to your relationsip.

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A male reader, Jmtmj Australia +, writes (1 February 2011):

Jmtmj agony auntMaybe I'm just biased cos I had a threesome go horribly wrong, but I compare threesomes to taking a leaky row boat out to sea for a bit of fishing... It's raw unpredictable fun, but the more you ride the leaky ship, the more risk you've got of sinking and inevitably it will. There's just so many things that can go wrong.

Personally I wouldn't take anything I valued greatly on board a leaky boat either.... like a treasured booty... ok I'll stop now...

I like pirates :P

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A male reader, anonymous, writes (1 February 2011):

It will all come out in the wash if you launder the sheets twice.

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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 auntEyeswideopen, you comment with such distain for what we're doing, then ask me to do something for you. Can't you find a way to be happy for those you disagree with? Don't you see the value in that? Give what you want to get. Surely you want something in your life or relationship? Maybe simply more happiness or more joy or more kindness or more understanding or whatever. Give it and you will receive it. The universe will provide if you do. Of this I have no doubt.

You don't have to agree with what I'm doing. It would be nice if you found one good thing to say, right? I bet it would make you feel better too in some small way!

Namaste!

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

eyeswideopen agony auntWhatever floats your etc... but please, let us know how it all comes out in the wash.

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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 auntThank you kirra07! Great advice. We have already talked about there not being any "restriction". She can do whatever feels natural and happens naturally. In fact, I want her to kiss him passionately the same way they kissed when they were seeing each other before she and I met. It's important to me that this be from her heart, not scripted, not controlled by me or by him or by her. She and I are both very "natural" lovers. What we feel, we express. We both do not like pre-planned activities or guidelines. Spontaneity brings us both joy and excitement. There are too many rules in this world already. As I think I mentioned, we are not reckless or cavalier and common sense is always applied, but during sexual pleasures there are no rules. If something makes her or I uncomfortable at the time, we say something, just as we express joy and happiness and pleasure openly, we express disapproval immediately if we don't like something and the other immediately responds with respectful, appropriate action, or we talk about it right then.

She actually wants a 3some because she wants to be busy! So, one will be screwing her and she will be orally pleasing the other or one of us will be giving attention to her boobs or kissing her or touching her, etc. We've also discussed double penetration and she wants to try it and so do I, so I think we have covered all the bases including STD protection.

Again, I believe it's better we do this with someone she knows, likes and that pleases her very much than someone that we don't know very well or that is not a good lover. I want her to have this and have it be as fantastic as it can be, or I wouldn't be doing it at all. She feels the same way. We're both in for a pound, if we're in for a penny.

Thanks again for your thoughtful and informative reply.

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A female reader, Adorskable  Mexico +, writes (1 February 2011):

Adorskable  agony auntSometime the threesome are more than a person can handle. Be prepare if the girlfriends decides to go back to her ex since he was great in the bedroom, or that they decide to go behind your back for seconds. Many things can follow a night of fun so be careful and be open minded because she or you might loose respect for each other after this encounter.

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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 auntNo, this is not planned to be a one time deal. She and I discussed at length the type of relationship we wanted very soon after we met and realized we were soulmates and falling in love. We agreed to take it one day at a time, one fantasy at a time and talk about each, discuss the pros and cons and make a mutual decision whether to fulfill them or not. We also agreed that if either was not comfortable or thought it would harm the relationship, we would not proceed with it.

She wants a 3some with a former sex partner of hers that satisfies her very much. If you're going to pick a sex partner, it should be someone that satisfies you, right? So, good for her! He's also someone she met after first getting divorced several years ago that was there for her as a friend too, to talk and listen, not just screw, so I thank him for that. By the way, she told me she does not want to see him alone, just to clarify that.

If, after this first 3some, she wants to do it again with him, we'll talk about it and decide. I think it will go fine and we'll probably invite him to join us again. Even though I don't know him as well as she does, what she's told me and what I've discussed with him by email so far leads me to believe that he is a great guy and has been a great friend to her and has her best interest at heart, so I can't fault that and I have seen why she is so fond of him as a good friend in the way he talks about her and how he wants her to be happy. He also congratulated me for winning her heart and told me she was totally falling for me.

My fantasy? Well, there are many, but the first will most likely be me, her (my girlfriend) and another woman yet to be decided. Standard stuff, but I've never been there. She already said what I said, that it will be a little weird at first and there will naturally be jealous emotions popping into her head as there are in mine about her and her male friend. But we agreed we will rise above pettiness because we know our love and the incredible connection we share, like no other either of us have had before, will endure. She and I are very much alike with respect to having an "open minded" attitude and we both have always hoped to find a partner with the same mindset. We've found it!

If after this first 3some with her friend she wants to visit him or have him visit regularly, we've talked about that too and it just might be something we do somewhat regularly. He has a girlfriend too, so we might get together as couples as well. This is all new to us in reality, but we have both thought about this a lot over the years before meeting each other and now it seems like a dream come true for us both. Still, we know we have to proceed with caution and not get carried away. Neither of us wants to live a swinger lifestyle. A few close friends from time to time? Yes!

Hey, thanks for your reply and your question!

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

Andulikeittoo agony auntHope you know what you're getting into. No matter how much in love couples are, including another person into your intimate life usually ends crewing up the relationship. some things aren't worth it.

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

eyeswideopen agony auntAfter you fulfill this fantasy of hers, and I assume you're thinking it's a one time only deal, I'm curious to know what YOUR fantasy is all about.

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A female reader, kirra07 Canada +, writes (1 February 2011):

Having been in this situation several times before, I have some tips and advice for you.

First of all, generally I would advise against having the 3some with a past lover, but the 2 of you seem to have discussed this. Remember, even if the idea turns you on in your head, this is worlds away from the reality of it. You might experience jealousy afterwards. Just a heads up. It sounds like you have made up your minds, so on to actual tips.

- Discuss beforehand what you want to do with each other, and what she can/can't do with the other guy. (i.e. not allowed to kiss, or he can't take her anally, or use condoms, no cuddling, etc.etc.). Just to confirm whether there are any special things that you want to keep between the 2 of you.

- Realize that as 1 woman with 2 guys, she's often rather busy and doesn't know where to put her attention. Chances are that she will direct more attention to the other guy because he is a guest and she doesn't want him to feel awkward being there with a couple. Maybe talk about this beforehand, and maybe share naughty looks during, even if she is paying more attention to him. Let her know it's okay that she is maybe neglecting you a little.

- Obvious potential pitfall: STDs

- Have a little debriefing section after it happens. Reassure each other that everything is okay, talk about how each of you felt about the experience.

Good luck

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