I’ve never had sex but have been invited to a Foursome. Should I do it?

Triangular_Triangle asks:

I’m 21 years old and have never had sex. I’ve been invited to have a foursome, it’d be two girls, my friend, and I. My friend is extremely experienced when it comes to sex. He and I talked about it and he’s very down, understandably so. We’re also on the same page since we’re both straight. However, should I let his experience affect my decision? It was a girl’s idea, so, clearly (I think), she wants both of us. My inexperience deters me as does the thought of performing inadequately compared to him; but I feel like these opportunities don’t come by often. I’ve had opportunities to have sex before but, for one reason or another (e.g. saying no to a close friend’s best friend or not wanting to be the side dude when a girl is in a relationship), I haven’t. Also note that my friend is encouraging of me to do this, saying that because one of the girls is into me (us) that it’s okay if whatever happens, happens. I’d rather not make a fool of myself, though.

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Demetrius says:

Part of me is a bit skeptical based on the “Dear Penthouse Forum” nature of your question but stranger things have happened. I turned down a threesome at 20-years-old, so anything is possible. No that’s not a humblebrag, I’ll get to the relevance of that later.

This is quite the situation you’re in. On the one hand, the idea of group sex and having sex with multiple partners is something a lot of people want to do. I’m sure the allure of being able to say you were in a foursome is cool to you, and by all means feel free to think it’s cool, but I think you need to get some sexual basics down before you start taking a dive into the deep waters of sexual exploration. There isn’t anything inherently wrong with group sex assuming all four of the proposed participants are above the age of consent and not being coerced. With that said, this might be the wrong time and place for you to have group sex.

I understand the allure, and I also understand the appeal of not only losing your virginity, but also to be able to lose it in the best way you can conceive of. With that said, do you really want your first sexual experience to be in a group setting? I don’t want to get all Debbie Downer here but let’s be really real. Most people suck at sex the first time they have sex. Sex, like most things in life, requires practice and experience to get better. Chances are good that you’ll be less than the best at sex the first time you have sex. I’m not saying this to inspire fear, I’m just trying to ground your expectations. A ménage a quatre sounds good in theory, but do you really want your first time to be so public? Many people feel inadequate after sex, and that’s just with one partner. Imagine feeling inadequate about your sexual prowess while you’ve got a crowd. I wouldn’t worry too much about your friend’s proficiency at sex so much as your own comfort level.

If I were in your shoes, I’d go about having sex for the first time with A SINGULAR PARTNER. Not that a foursome should be completely off the table, but you definitely need to be comfortable with sex, and your skill level at it, before you start having group sex. It’s sort of like learning to swim. Some people would throw you in the deep end, personally I’d start you off in 4 feet of water with floaties. You can go try to learn to swim in the deep end if you want to, but it’s probably better to learn the basics first. Just my opinion. Hell, if one of the women in this proposed foursome is keen on sleeping with you in a group setting, why not sleep with her prior to the foursome? If she wants to have sex with you with an audience, see if she’d be down to get in some practice beforehand.

Now, if you do plan on going through with this ménage a quatre, which obviously you do because you’re a 21-year-old guy being offered sex with two women, here are some good rules to live by. First, consent is required on all parts. Second, figure out everyone’s boundaries and expectations before you have sex.Maybe your guy friend will want some contact between you both during sex acts, or maybe he has a no eye-contact rule during a foursome. Who knows! Same for the ladies. They could have certain expectations and boundaries that you have no way of knowing until you ask, so ask ahead of time.Third, bring lots of condoms and use them! If you plan on switching from partner to partner, or even from orifice to orifice with the same partner, you need to change condoms. Lots of reasons why, number one being that you don’t want to potentially give anyone a bacterial infection. In general, you should wear a condom when engaging in any penetrative sex acts. Yes, that includes the mouth, anus, and vagina. If you plan on performing oral sex on one of the ladies, use dental dam. Since most people don’t have or buy dental dam, you can MacGuyver a condom into a dental dam. Fourth, have fun! If you’re doing this, you’re doing it for the fun, right?

Now, remember that threesome I mentioned above, well here’s why I wanted to bring it up. Here’s the scenario. Two women are hanging out with me in my place. We’re drinking, we’re flirting, and as the night goes on it’s clear that the ladies would like to have a threesome. Imagine how cool that sounds to 20-year-old Demetrius! Even at 20, I knew the tips I mentioned above: Consent, Boundaries and Expectations, Condoms, Have Fun, so I try to go through each one. I progress through steps #1 and #2 and start talking condoms. I’ve got some ready to go and then one of the women in this potential threesome tells me she doesn’t use condoms. Apparently she has an allergy to latex condoms and has decided the best thing to do is to not use condoms. When I mention that there are alternatives, though they aren’t as effective at preventing STD transmission, like lambskin condoms, she then says “I know, I just prefer sex without a condom”. Weighing risk versus reward, I have to turn down this threesome. Not just because of the risk of STD transmission, but also because it’s not something I’m comfortable risking. If a sex act sounds appealing but you feel uncomfortable doing it, don’t do it. Simple as that.

Hope this helps and trust me, you might not get another shot at a foursome, but if you aren’t comfortable engaging in one it’s not worth it to try.

Good Luck Out There.