Threesomes and Groupsomes

By S.

Sometimes you wish that you had an extra hand, or mouth during sex. Maybe bringing more than one friend to bed (or couch, floor, shower, etc.) lets you play with different gender dynamics, or maybe it satisfies your voyeurism or exhibitionism. Maybe you want to bring some more friends into your fun and play with some new types of relationships, or maybe you just want to try something new and would like a little extra help and a little more party in something that is good with two, but could be better with three, four, or more.

So here is the Oberlin Fucks step-by-step guide to having an amazing three-way, and mind-blowing group sex without having to have a really awkward cup of coffee the next morning.


1.  Make sure you want a threesome or group sex. And by you, I mean you. Not you and your lover, not some boyfriend you want to give a birthday present to, not a group of friends, YOU. You need to decide if this is something you want to do your self, and if this is something that you would enjoy. Sex in any form should be something that you do because you enjoy it that way.

When it comes to pushing boundaries, fuck compromising.  Do what makes you happy and make sure everyone involved is fucking by that philosophy. So think it through before you are in the heat of the moment, because you never know when a party might take a turn for the pants-less.

.          Are you possibly turned on by another set of eyes seeing you in the act? What about seeing others?

.          Would you feel comfortable with some same gender play? Different gender play? Or do you want to keep it a boys night or a girls night only?

.          Would you get jealous, possessive, protective or feel threatened?

.          Would you feel dirty? Would you like that?

.          Would you want this to be with people you know well and trust? Or do you want to add in someone you don’t have much of a connection to that can stay separate from you day-to-day life?

.          How far do you want to go? Penetration with one person but just oral with the rest? No penetration? Pants on? Or do you just want to watch the first time?

.          Is this a one-time thing, or do you want to have this party every Thursday while eating dinner?

Whatever you decide, keep reevaluating it and remember that you can change your mind. Keep partners posted on what you’re okay with (“I love sucking your hard cock and want to see someone else suck on it too, but I don’t think I could watch you fuck another girl in the vagina with it–I like that too much for me, so could we play with other guys? Or could my friend Latisha come over and just suck you off?”).

It’s totally okay to admit that you want to keep you partner just for yourself and don’t think you could see them with someone else in the mix. A lot of great cooks don’t share their kitchen well but still make delicious savory meals. No shame in that.

2.  Make sure you’re with the right people. This is a key step in avoiding an awkward or uncomfortable situation and will make your night as sexy and rewarding as it can be. Maybe you want to get together with people you don’t know that well so that you are going into it without any baggage. Maybe you want it to be your two best friends (but be careful with that one). You could join up with a couple as an extra hand, or bring someone into something you have going already. Maybe you walk into a party and realize that they are all sexy, cool people and you want to be sandwiched between that redhead who was in your freshman seminar and that guy who might have lived down the hall from you.

Whoever it is, make sure that they are chill with the situation, want to do what they’re doing, and are down with USING PROTECTION. As long as they are people who understand your boundaries, turn you on, and won’t blow the situation out of proportion, they should make great play-friends.

3.  Get excited for the occasion. Group sex doesn’t come around every night for everyone, so why not get excited about it? This is one of those occasions that you can make an evening out of getting ready and wearing something sexy. If you are falling into a convenient situation as it comes, look at it with the same amount of excitement.  Don’t be afraid to seize a good opportunity when one lands in your lap.

4.  Take the awkward out. It’s only awkward if you make it awkward. If you walk into something totally chill about it, it is easier for everyone else to relax and act as if this is something normal. You don’t need to justify what you’re doing, and it is okay and expected that you won’t look you’re most suave at all times as you try to not trip over six legs.

If you have all consented ahead of time, and agreed on what you are doing, it might help to split a bottle of wine or champagne (why not celebrate it?) to take the edge off. Introduce yourselves, talk about turn-ons and joke around a little bit. What fun is sex if you can’t all laugh together?

5. Three-way foreplay and more play should be about SAFER SEX. Show off how you can put a condom on with your mouth, take advantage of the extra hands to lube you up, and once you have you latex out and on, have a little fun with each other. Have your nipples sucked by two different experienced mouths, or try a sweet and spicy massage, with one person caressing you as another bites down your back. With enough people, everyone can be pleasured, even while giving.

6. Great positions for groups take advantage of that extra hand or mouth. Giving head with a friend means one person can suck the tip while the other can focus on the balls.  Let one person work a clit, while someone else takes care of penetration.

To start out, you can take turns focusing your attention on one person. Kiss them and pull their hair, while someone else sucks on nipples and a third explores further down or revels in the role of holding someone down for a little bit of human bondage play.

Once you all are involved, use free hands to pleasure whoever is not getting in on genital action. In a three way, it can be most relaxing to have the penetrating partner lean back with a second partner riding him/her in a reverse-cowgirl stance. This lets the third person sit facing whoever is being penetrated for either some penetration of their own (MMF sex, or with some toys into the game) or to be played with while passionately kissing the friend being penetrated, and everyone has a good view. One of the most erotic things I have found is kissing someone going through an orgasm. When bringing more people into the picture you don’t have to all chain, or circle up rather switch positions and partners as much as you all find satisfying.

7. Leave on a good note. When everyone is satisfied and exhausted, check in and tell each other what you loved and if you want to do it again some time.  You should always have a plan for where people sleep so there is no awkward or jealous vying for the bed. Try not to overstay your welcome and keep things on a light and friendly note as you walk each other home. All good sexual excursions come to an end, and it is the truly desirable that everyone recognize that point and move on with grace. Be cool with people the next day and whenever you see them afterward. You had a great experience with them and a casual “hi” in line at Stevie should be okay, but nobody outside of that night needs to know that you fucked them in every hole, rather than having just met over a group project for class. Nobody wants a strained or uncomfortable relationship, so if you keep it chill, they most likely will too.

Play nice with the other kids,

Xoxox