A
female
age
41-50,
anonymous
writes:Hi all. The live-in boyfriend and I have been together for 5 years. We are very solid, trust each other completely, with little to no jealousy whatsoever, and we have a great sex life. So after about 6 months of discussion, we've finally decided to have a threesome. I'm not being pressured into anything; in fact, it was my idea. Obviously he's been on board since day one.So now we've found our girl, the date and venue has been set, and arrangements have been made. It happens a month from now. We have done every shred of reading and planning and talking to set rules, boundaries, expectations, safewords, and all that important stuff.A few things confuse me very much though. Like the condoms. Obviously we want to practice safe sex, so the condoms are a must. As I understand, he has to replace the condom every time he penetrates a new girl. I just can't wrap my head around the logistics of the whole thing.Question 1: Switching condomsSay for example she and I are laying on our backs next to each other, legs wide open, and we create some sort of porn star scenario where he penetrates me for say, 2 or 3 thrusts, exits me, and penetrates her for a few thrusts, and then return to me, etc... He would have to change condoms everytime he moves from one girl to the next. Wouldn't that be kind of a mood killer? Or does everyone just lie there waiting for him to make the switch because they understand the necessity?I'd also love to give him the experience of a double blowjob, because, I mean, come on. Every man has fantasized about this, and if I'm giving him his ultimate threesome fantasy, he HAS to have this. Does he wear a condom when we do it? I'm thinking it kind of defeats the purpose, because he'll be desensitized, and won't be able to feel the full sensation of two mouths and two tongues on his d*ck?Question 2: Condoms neededWe have this lady for the entire night. We are really planning an all night f*ckfest. With all the condom switching going on, how many would we use in a five/six hour period? I have no idea how many to take with. ??Question 3: JealousyThis has been my main concern from the start. Yes, by nature I am not jealous or possessive at all (unless there is an actual threat and the situation calls for it), but I think we feel very secure in our relationship, and we trust each other absolutely, and that leads to neither of us ever feeling threatened. Just the idea of watching him have sex with another woman to the point of orgasm, turns me on more than any other scenario ever has (I've concluded that I have somewhat of a serious cuckquean fetish going on here). As a test run, I took him to a stripclub, and got him a lapdance while I watched. To see what my reaction would be. I was ecstatic when I didn't feel any pangs of jealousy while watching a gorgeous girl wave her naked hoohah in his face. My main worry is the fact that fantasy and reality are two vastly different things. Yes, thinking of it now makes me all happy in pants, but what if I get to that moment and it's just too much to handle to see him make love to another woman? I doubt that it will have me freaking out completely, but I do expect to feel somewhat jealous. How do you deal with this? Just channel it into my hoohah?Last question: InitiationMy last question is about the initiation. Our unicorn has agreed to the threesome, and will be spending the night with us for the sole purpose of all three of us having sex with each other. So there are no secrets, and there will be no surprises. Thing is, I have no idea who has to start what, who initiates what, who kisses who, and that stuff. Obviously this will be my first experience with a girl, so as excited as I am, I'm a little terrified too. I don't want to pounce her the moment she gets there. And I don't want the boyfriend to, either. Obviously you want it to be slow and sensual, savour every touch and all that stuff. But I have no idea what to do, and I'm scared of being so nervous, that I'm too afraid to make a move. I don't want it to be awkward because I have a case of the stagefrights. It's a real possibility, because I have no idea what to do with a girl. I can suck d*ck, I have no idea how to eat p#ssy.We have a huge penthouse suite, with a jacuzzi for the evening, so I thought we could all get into the jacuzzi, have some champagne, have some soft music playing in the background, but then what? What do we do here, and how do we make it not awkward? (I just want to add here that our number one rule from the very start was that we should under no circumstances be drunk at all. As we are getting a bottle of champagne with our room, we decided that it will be the only alcohol we will be consuming, because one glass will help with the nerves, and more booze will ruin it. Drunk sex is already a mess when it's only the two of you, it can only be disastrous when you add a third person to the mix. :D)Footnote: CommunicationI feel the need to mention that we do have a very open and honest relationship, and the lines of communication are always flowing. We discuss every detail surrounding this decision, are setting ground rules and boundaries every day, and it's a continuing discussion about our feelings and our expectations. We've arranged to meet our unicorn a few times before D-day also, so she could give us her rules and boundaries too, what she allows, what she doesn't, and to make sure that there is attraction from all parties and everyone feels comfortable around each other. (I opted not to go for any friends or close acquaintances, cause I felt it would be a bad idea. I don't want awkwardness or suspicion between friends when we happen to be at the same party afterwards.)Anyone that has done this who can give me some tips and advice on the things I'm unsure about? Please help me! ??
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blow-job, condom, drunk, jealous, lapdance, orgasm, period, porn, sex life, sex with another, threesome Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, anonymous, writes (29 November 2016): I agree with the male anon that many people on this site are against threesomes but in the main that's because we've all lived a long while, had a fair amount of sexual experience and/or tried out threesomes so feel qualified to respond. It's not because we're all a bunch of killjoys or prudish.
A
female
reader, anonymous, writes (29 November 2016): You sound like one incredibly organised woman. Going in to this level of detail is impressive. BUT emotions cannot be planned and you, your boyfriend or this other woman may get feelings during or after that were not accounted for. I guess you know that risk. Do post back and tell us the outcome.
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A
male
reader, anonymous, writes (29 November 2016): Hi. I am impressed with your question-- you are a very good writer!
In my opinion this website is biased against threesomes, so take our advice with a grain of salt.
However, If you want to spend the rest of your life with your BF I would think long and hard about whether a threesome is worth the risk. It sounds like they have no negative after-effect in maybe only 5 to 10% of cases.
I should also add that I have never had a threesome. I'm kind of a jealous guy so am lucky that my wife shot down one I proposed years ago!
Best of luck!
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A
female
reader, anonymous, writes (28 November 2016): "Obviously he's been on board since day one". I'm sure he has. He will get a real taste (quite literally) of another girl whilst being in a relationship with you. It's legitimised cheating. I doubt very much you can control the boundaries in his mind. Good luck with your quest.
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A
female
reader, Youcannotbeserious  + ♥, writes (26 November 2016):
 Only three words of advice:
DON'T
DO
IT.
The end.
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A
female
reader, Anonymous 123  +, writes (26 November 2016):
 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
Just a sneak peak into threesome gone wrong scenarios. Do read these and the many, many others like these before you take the plunge
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A
female
reader, mystiquek  + ♥, writes (26 November 2016):
 I will start off by saying that I've been on DC almost 10 years now and these threesomes never work out too well. Its usually the woman who winds up getting jealous and hurt. At least 75% of the time a threesome leads to a breakup. Don't believe me? Go look in our archives. Let's be honest, a 2 woman/1 man thing is a man's fantasy, and a big seller in porn. Fantasy and reality are not the same thing and what looks good on film or as a fantasy is NOT the same thing. I hope you will consider what everyone has said. We certainly can't stop you but I hope you truly have thought this all through because once you have the threesome, you can't go back. Many women tell us that the man isn't happy with just once and wants to start have threesomes on a regular basis..so there you go...another potential problem!
IF you chose to go through with this, take more condoms than you think you will need...at least 3 boxes just in case.Both of the ladies should wear dental dams and I'd also suggest female condoms. You just CAN'T be too careful! EVERYONE should be tested first...wouldn't even consider it if that's not done. The three of you need to sit down and talk, make sure everyone is on the same page, no surprises. I've read where sometimes the guy gets so into the new woman that he ignores his partner and she winds up feeling very jealous, insecure and hurt. Your partner and you should have some code word for "stop" in case things don't feel right for one of you. Make very sure you want this OP. I don't mean to sound like such a downer, but this whole experience could change your relationship forever and NOT in a good way.
I wish you luck...be sure this is REALLY what you want, and what you can handle. I'd never even consider this my first husband wanted to do this (with my sister!!)..uh yeah..he got the boot!
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A
female
reader, debsray +, writes (26 November 2016):
I've done it with my boyfriend of, at that time, 4 yrs. I felt some jealousy pangs, not while the sex was happening, but before that when he seemed to make me disappear. He felt some jealousy also, as he felt she was too much into me. Remember, the new girl is the new toy and he will want to pay more attention to her. Make sure your boundaries are very clear and that they apply to the before, during and after.
Btw, both of us decided we did not want to do that again. The aftermath was too emotionally draining and almost ended our relationship
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A
female
reader, Andie's Thoughts +, writes (25 November 2016):
 I think "make love to another woman" says it all. Threesomes are sex, not making love. However, your natural thought process was to call it him "making love" with someone else.Personally, I think that's where your common sense and desire to keep your relationship is kicking in.You need a few boxes of condoms, all three of you STD checked beforehand (not weeks/months ago), both women on birth control for however long it takes to become effective and to never get so lost in the moment that you forget to put a condom on properly, tear it by accident or one of you goes too far with the addition. Sounds less fun when you can't lose yourself in it because the risks are too high.Ultimately, it may work for a few, but not for most, and it ruins relationships easily. I'd never recommend trying it, unless all 3 are single and have no partner to lose.
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A
female
reader, Ivyblue  +, writes (25 November 2016):
 Condoms may protect you and him but you do need to consider just how you are protected if you decide, or get caught in the moment even, have oral sex with her. You can still catch an STD so I would consider using a dam. ( like the dentist do, that square piece of thin rubber). Not entirely sexy but nothing screams mood killer than-Gonorrhoea,Hepatitis B,Chlamydia etc. later on down the track. Now also remember these thing can be transferred via toys and fingers etc. How many condoms do you take - a couple of boxes and as for switching, it is what it is. Jealousy-thats when you use you exit word because you cant undo what you see if you dont. Initiation, If she is a professional I would assume she will take some charge of the situation if still in doubt why not discuss this with her prior.
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A
male
reader, Garbo +, writes (25 November 2016):
 I wish to address your question number 3, but from the man's perspective.
There was a time when I was open to the idea of a 3-some with my woman. We were together for a long time, loved each other, and 3-some porn as in FFM used to get me off on days when me and her could not get it on.
Sometime later, we were at a bar with a girl who had a huge crush on my woman, and the girl made lot of effort to get me to want her. After some drinks, her desires took better of her and she started making passes on my woman: words, body actions... affectionate, erotic and desiring of my woman. The scene was strong that she pissed me off. She was moving onto my space, my woman... something only men do ... but men even know the limits.
That's when I realized that my woman is my woman and no other woman can have her. Yes, it looks hot in porn, but in reality that woman was like any other guy moving into my territory. It will never happen.
Just sharing my experience.
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A
female
reader, aunt honesty  +, writes (25 November 2016):
 Okay first off I think you need to make sure this girl is clean, if that is the case then why all the condom changes? Are you worried you might get a bacterial infection? Or was it to protect from STI's?
Me personally I don't think it is a great idea, as a fantasy yeah but in reality what if he looks at her with lust and passion that you have never saw before? What if he focuses on her a lot more? Shows more interest in her? What if he is so turned on by her that once is not enough? These are things that can and do happen when a third person is invited in.
It probably will be awkward to begin with anyway but hopefully the champagne will ease you all up.
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A
female
reader, like I see it +, writes (25 November 2016):
 Full disclosure, I've never brought a third person into any of my relationships, although I did have an ex who really pushed for this. It's not something I'm personally interested in and frankly I can't think of a faster way to put trust issues into an otherwise healthy relationship. I think there are a select few situations where it can work, but overall the odds of it going successfully and leaving no discord in its wake are overwhelmingly outweighed by the odds that one partner will end up jealous (either of the unicorn's physical attributes, or of how attention is divided during the encounter) or that the other partner may try to revisit the unicorn on his or her own time or may push for future threesomes with others on the grounds that the cuckold or cuckquean has already agreed to opening the relationship before.
It's a huge step in a relationship, and one you can't undo once it happens. I highly recommend you search this site for some examples of people, male and female, who have written in desperate for advice after threesomes didn't go as planned or fantasized. All the instructions in the world don't necessarily prepare you to see your partner in the flesh being intimate with someone else.
Not to rain on your parade here, but the fact that you're already worried you might be jealous would be a huge red flag to me. There is a world of difference between watching and touching, so the fact that the lapdance didn't bother you doesn't mean watching your boyfriend physically having sex with someone else won't cause a different reaction. I think you already know this. In your shoes I'd be weighing the best case scenario (ticking a sexual fantasy off your bucket lists) very carefully against the worst case scenario (ruining a 5-year relationship for a night of pleasure with a near-stranger).
If you do go through with this, bring all the condoms you expect to need and then some. And use them, even if it doesn't feel as sexy. Your post is somewhat vague about how you found this girl, but I'm going to take a wild guess that someone who agrees to this sort of thing (after all, there's not a lot in it for her unless you two are paying for the experience) has a reasonable amount of past sexual experience under her belt. Which is more concerning, the prospect of having a condom between your boyfriend's dick and the blowjob he's getting, or the possibility of this girl bringing a little something extra to the encounter (like herpes, or worse) and one or both of you ending up with it? That's something the two of you really have to weigh if you're thinking of bareback at any point. Even if the unicorn has a copy of clean, RECENT test results in hand as part of your preparations for this, you are better off using protection for EVERY act no matter how low the risk, including dental dams if you or your partner plan on giving her cunnilingus or having you receive it from her.
Speaking of protection... what is the backup plan if a condom fails, especially with all the condom switching? Is this girl currently on birth control pills or some other form of reliable contraception? Would she be willing to take the morning after pill? Is abortion legal and available in your country? Would she be willing to have one? The time to find out about this is before the threesome, not in panic mode after the fact.
Just some things to consider. Good luck if you do go through with this, and best wishes.
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A
female
reader, anonymous, writes (25 November 2016): I can only give one suggestion regarding your query on constantly changing condoms - why not have you and the other girl use female condoms?
I would caution you against going through with your plan though - you have a great relationship as is,why spoil it?
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