It's not as simple as it sounds. There are technical issues to be considered. Women can easily accommodate two cocks at the same time, but men only have one dick...and it can only go in one soft, tight warm place at a time. And there are emotional issues. Seriously, it can be an emotional minefield.
I'm not going to tackle the technical issues here. The porn industry has done that for us. I'll focus on the emotional and relationship issues since those are the ones that cause all the problems.
Since I've had the pleasure of enjoying more than a few three-ways over my lifetime, I thought I'd share some tips to help you get it right. There are variations to the 3-way theme, of course - two women and one man, two men and one woman, three women, etc. Most of my suggestions will apply to most situations, so I'm going to focus on fmf, two women and one man, the subject of thousands of porn movies and millions of wet dreams.
- Talk about it beforehand. Discuss with your lover how you would like it to go. Discuss any limits you have for playing with a third. Are you ok with him kissing her? Will you be ok if she doesn't want you to have vaginal intercourse with your new friend? What makes you nervous about the idea? Do you both feel comfortable with it?
- Expect the unexpected. No matter how well you may have planned it, something will not go as you expected. Maybe one of you wants to stop and leave in the middle of it or maybe you (speaking to the men, here) can't "perform." Ladies, what if your lover gets so into the other gal that he completely ignores you? Seriously, these things happen. Have a plan for them. Know what you'll do so you don't end up in a panic.
- Remember that emotions are unpredictable. Your partner may be telling you that she's fine with it, that she is really excited about it, that's she's looking forward to it, and all of that is probably true, but it doesn't mean that she won't become an emotional mess as soon as things get started. I am assuming here that you and your partner have a romantic or love relationship. If you're just fuck buddies, go for it! By the way, guys, sometime you think it's a fuck buddy relationship and she thinks it's more. Just a heads up. But as I was saying, the reality of seeing someone you love having sex (or deeply kissing, or...or...or...) someone else can be very hard to take, even if you agreed to it. The first time I tried a 3-way with Hubby was a disaster. I had already been part of several before then, so neither of us expected that there would be a problem. However, the second I saw him kiss her, I burst into tears. I experienced an eruption of emotion that overtook me completely out of the blue. To his credit, Hubby called a halt to everything and he and I left, which is exactly the right response to the situation. If he had kept going, hoping I would get comfortable with it eventually, I would have had to leave. And it wouldn't have been pretty when he got home later.
- Be prepared for even the most confident woman/man to experience some insecurity. I've known some absolutely gorgeous and sexually free women who avoid 3-ways because of their own body issues. And if porn-film-body women have body image issues, you can be certain than the rest of us do, too. And this isn't just a female issue. Men worry about the other guy having a bigger cock or perfect six pack abs or...or...or.... Until you all get to know each other and are comfortable with each other, body image issues will be "the elephant in the room." Handle this upfront by reassuring your partner (Oh, Baby, I *love* your tits, etc.) during the act.
- Focus more on your partner than the third player. Men, this means you should focus three times more on your partner than the other woman. Otherwise, she will perceive it as you giving all the attention to the other woman. Women, you need to give your partner at least twice the attention you give to the other man. Three-ways that go bad usually go bad because of this issue - the woman feels that she's being ignored. Not only will it piss her off, but it will light a match to every insecurity she's ever had and an emotional eruption is likely, either right then and there or later.
- Guys, show some discipline. I know you're excited. I know this is a dream come true. Yes, maybe your new playmate has a much better body than your partner and all you want to do is play with that sweet fresh pussy all night, but show a little bit of discipline and focus on your partner. It will pay off. Besides, it's just polite.
- Focus on comfort in the beginning, then pleasure. Gentlemen, here's a hint to help you navigate the emotional rapids I've just described. Spend the first half of your time together focusing on your partner. That doesn't mean ignore the other person, of course, but devote most of your attention to your partner. Make sure she has a really, really good time. Make sure she has no doubt in her mind at that moment that you care about her very much. Once she feels secure, she will probably direct you to play with the other woman or she will encourage your activity in that direction.
- Take your time. Unless it's a mutual masturbation session, it's going to take longer for three people to be satisfied than for two. Don't rush it. It's supposed to be fun and pleasurable. Enjoy the foreplay. Enjoy watching your partner and the other person play with each other. This doesn't happen every day, ya know! Savor the moment.
- Debrief afterward. After it's all over, the third party has left, and you and your partner both have your clothes on, talk about how it went. What worked for each of you and what didn't? Check in with her about how she is feeling. Don't just assume it was great for her. Be honest about what you would like to do differently next time (if there is a next time). Most importantly.......
- Be Grateful. The reality is that most women will not be interested in having a 3-way with you, Gentlemen. It's not because they are not interested or curious, but because of the body image and emotional security issues I mentioned above. If you are in a romantic relationship with a woman who is willing to try it with you - even once - you are very fortunate. Women like that are rare. Be sure you say "thank you" and that you demonstrate your gratitude to her in whatever way is appropriate given the parameters of your relationship.
After the disastrous first try at 3-way that Hubby and I had, we talked about it and tried again. That time we set some rules (no kissing her, etc.) and it went better. I was still an emotional wreck afterwards, but at least I made it through. Eventually, I became secure enough that he wasn't going to leave me for one of those other women that I was ok with it. None of it was logical or rational, but that didn't matter. Emotions are what they are. At another time we played with one of his friends (a man) and he (Hubby) made the rule that the other guy wouldn't be allowed to fuck me. Yeah, men have their issues, too.
The reality of a 3-way rarely lives up to the fantasy, but that doesn't mean it can't be great. It just means that you should moderate your expectations, go with the flow, and be prepared for the unexpected.