My Threesome from Hell and How to Avoid One

When she approached me she claimed she didn’t usually approach women she didn’t know, but a few drinks had her feeling “spunky” that night. She expressed to me that she found me attractive and loved the way I carried myself. We worked in the same club, so we’d seen each other plenty of times, but never spoke. That night, she built up the courage to invite me to a threesome with her and her boyfriend, and immediately I knew it wasn’t a good idea. Although I’m a big fan of threesomes, I don’t guest-star. By this I mean I don’t enjoy being the invitee; I’d rather do the inviting. I explained this to her, and told her I wasn’t comfortable with the idea. I know what I’m capable of sexually, and I have no problem allowing the entire party to get really “hands on” in my own threesomes without any arising insecurities on my behalf afterwards. I like to have threesomes for ME, and not because I was pressured by my partner; but not many other women possess this confidence. Many women participate in these ménage à trois to please their boyfriends. However, she continued to pursue me over the next couple of weeks, and insisted she was not one of these women. Since I was single for some years, and the couple was attractive, I decided a little fun wouldn’t hurt.

We agreed to meet at a small Dyckman bar to break the ice. I had patron over ice; they had henny. The vibe was great and conversation between her and I flowed. He was nervous and couldn’t drink as much as she and I since he was the driver, so she asked me to make him comfortable. I did so by simply including him in our conversations and maybe a little dancing. She and I had already discussed boundaries, but I was still careful and avoided being too flirty although it was just dancing. Once the drinks crept up she and I became the attention of the party. We laughed, danced on each other, and flirted. All healthy appetizers before the main course. We felt good and ready and made our way to start the three-way.

By the time we reached the apartment, the liquor had completely hit us and everyone seemed ready. Since I’m sexually aggressive when I drink, I took the lead and initiated things. Naturally I started with her before moving on to him. I won’t get into details because that’s not the purpose of this post (won’t get Zane over here), but not even 15 minutes in, my hostess gets up from the bed and attacks him. I get up from all fours and sober up quick, preparing myself to fight…..naked! Fortunately, she stormed off to the bathroom in tears, slamming the door behind.

Needless to say, the threesome was over but the rest of the night wasn’t. I hurriedly, put my clothes on and the next 20 minutes or so were filled with a screaming couple, a stream of tears, and landing fists. She wanted to fight everyone in that room. That was the last time I guest-starred and I don’t think I ever will again.

Not all of my threesomes happened this way; I simply made the mistakes of going against my gut and joining a party I didn’t know well. Couples who participate in threesomes should both be secure in their relationships, and should both want to have one. Everyone is different, but you should know yourselves and each other well enough to know what you can and cannot handle before inviting a third person into your web.

This isn’t a complete go-to-guide, but these general rules lay a good foundation that help ensure an enjoyable and drama-free party of three. Here are the basic ins and outs of the business (no pun intended.)

Rule # 1: Establish the rules.

Threesomes are best when they’re spontaneous, but unless you’re comfortable with going out and recruiting someone in public places, most couples plan theirs in advance. You don’t have to plan everything down to the move, but make sure you hash out the do’s and dont’s to avoid jealousy and a civil war in your bedroom. Discuss these rules amongst yourselves, then make sure the third party understands and agrees to them. Maybe you’re not comfortable with them kissing, or maybe you don’t want your partner giving the third party oral sex. Whatever it is you don’t think you can handle should be a rule. These don’t have to be permanent and can always be revised. Personally, I never have any. I’d rather have a fully organic experience and let things flow, but everything ain’t for everyone. This generally isn’t a good idea if it’s your first time. Whatever you decide, make sure everyone is on the same page.

Rule # 2: Let the woman take care of business

This rule generally applies to men as it is a classic rookie mistake. Most guys who never had a threesome express their interest far too eagerly when it comes to suggesting a girl(s) he has in mind. This can lead to insecurities that cause his girlfriend to cancel the whole thing. Fall back and allow her to handle things. The woman should suggest who will join the couple and she should also be the one to approach the other woman. In my personal experience, having a man approach me about a threesome with him and his lady is creepy anyway. I rarely guest-star, but whenever I did, I was definitely more receptive to the woman’s invite. Whether you decide to invite a friend or a stranger is up to you both, and each comes with their own pros and cons* (I’ll elaborate on this a little more), but BE COOL. If she shows you a picture of a prospective gal toy, respond nonchalantly; something like, “yeah, she’s cool” NO MATTER HOW ATTRACTIVE SHE IS. Again, both parties should be secure in their relationships before deciding to play with someone else, but it’s natural if your girl gets a bit uneasy if it’s her first time with you. It’s also natural for the man to feel excited, but this is a sensitive step, so proceed with caution. Additionally, don’t even think about exchanging contacts with her after it’s all said and done. Allow her to maintain the relationship with her; there’s no need for you to be in touch! I’m sure it’s innocent (*side eye*), but you don’t need to build insecurities where there were none. Now if your girl is too shy or uncomfortable with approaching another woman, then you may need to take the first step. But I’m having a hard time picturing a good threesome if this is the case, because this is not for the faint of heart.

Rule # 3: Make sure everyone’s hands (or mouths) are busy

This is the rule that ruined my aforementioned threesome. When she and I discussed our likes and dislikes respectively, I expressed how much I enjoyed watching my man get it on with other women. In what I assume was an attempt to sway my decision in her favor, she agreed that she did too. Though everything seemed to be going great the night of, I mistook her jealous glare for lusty voyeurism. I realized (a bit too late) that his focus while having sex with me caused her to feel left out, which hurt and enraged her.

With that being said: Make sure everyone is involved! There are more than enough mouth and hands and it’s called a threesome for a reason. The only other reason for leaving someone out (aside from voyeurism IF you’re REALLY into that) is if the man is left out while the women familiarize themselves and are warming up. I promise they will come back to you….and if they don’t, well, maybe your girlfriend is a lesbian.

Rule # 4: Mind your alcohol tolerance

Another broken rule that potentially led to the detriment of our little sex party: I hold my liquor pretty well, but apparently, she doesn’t. Although she should’ve been honest about her feelings from the start, the amount of alcohol consumed was the true cause of how the night went down. I understand the need to loosen up before hitting the sheets (or sofa), but getting too drunk isn’t the best idea. Aside from uncontrollable emotional outbursts, you don’t want to risk getting sick or even worse…..a penile malfunction. I have a friend who got too drunk for his threesome and fell asleep, missing the entire thing. Additionally, you’d want to be able to actually recall the night before, or else what’s the point? Know your limit and know when you’ve had jusssssst enough.

Rule # 5: Decide in advance whether you’re having a sleepover or not

So your threesome was a success! GREAT!!!!! Now what? Is she staying? Where will she sleep? Should she go home? This detail is often forgotten, but you don’t want to decide these things out right after you’ve finished. Decide in advance if she’s staying, and if she isn’t, be sure to accommodate her transportation back home.

Rule # 6: Oops…almost forgot….don’t forget protection!

Honestly, this is the most annoying part of threesomes (besides being too nervous to get it up)- the putting on and taking off, and putting on again. Using condoms in threesomes can get messy, literally and figuratively, but you want to do it. If you decide to pick up a stranger, you don’t know their sexual history. The same goes for best friends, but even if you do trust her, what if your boyfriend gets her pregnant? The list of complications are endless. You should use condoms and never double dip! Some couples go as far as using finger condoms and dental dams and while it’s not a bad idea, I get how you might not want to feel like you woke up in a plastic recycling center. However, be cautious and play it safe.

*A note on choosing a third heel (see what I did there!?)

Deciding whether you’ll choose a friend or stranger is entirely up to you, but you should keep some pros and cons in mind. Pros of inviting a friend: approaching a friend is usually easier than approaching a stranger, and you know her history better than some random, but some of the cons include (but are not limited to) the effect this threesome will have on your friendship after and the arising of insecurities after witnessing said friend please your man. Will these images haunt you? Will the three of you be able to sit in the same room again? You may want to approach a stranger, and though the cons include not knowing their rap sheets and the possible extensive search until someone says “sure,” the pros can benefit your relationship in the long run. You can easily send your sex slave away and enjoy the memory with your man until you feel you want to do it again.

However it may go down, keep in mind that threesomes can be a healthy way to rediscover yourself and your partner, and is also a good way to spice up the relationship a bit. There is nothing wrong with exploring your sexuality, and fulfilling your fantasies. Just be sure you’re both on the same page, and always keep your partner’s needs and feelings first. There’s no need for anyone to walk away with a sore jaw. Trust me; it doesn’t feel good.

Have any of you had any bad threesome experiences? How did you ensure an enjoyable night for you and your partner? How do you feel about guest-starring? Did I leave any major rules out? Comment below and tell me your thoughts!