8 “Ultimate Fantasy” Sexual Situations I’ve Been a Part Of

Caitlin Jill Anders 10-12 minutes 5/31/2021

And whether or not they’re worth the hype.

Caitlin Jill Anders

Photo by We-Vibe WOW Tech on Unsplash

I’m a very sexual person, so whenever an interesting, unique, or just downright hot sexual opportunity presents itself, more often than not, I’m all in. I love trying new things when it comes to sex, and if all goes well, I’m likely going to want to keep trying it over and over again.

When I’m gathered together with a group of friends and they start talking about sexual fantasies they really want to take part in, I’m always that annoying person who raises her hand and says, “Oh I’ve done that!” Then everyone rolls their eyes and I giggle to myself about how slutty and wonderful I am. It’s pretty great.

I’ve been a part of a bunch of “ultimate fantasy” sexual situations. The things tons of people have on their sexual bucket lists. The things people fantasize about when they’re alone. The things people watch porn reenactments of. Am I bragging? Maybe a little.

Of course, there are definitely people who are way more adventurous and experienced than I am. There are still plenty of sexual situations I haven’t had the chance to be a part of yet. The ones I have though, for the most part, have been pretty damn great. They’re not always exactly what you might expect them to be, which is interesting to discover. I think that’s why I love talking about them so much. I love letting people know what those “ultimate fantasy” situations are really like, and if it’s actually worth trying to get involved in them.

Getting a private dance at a strip club with a partner

A few years ago, a partner and I found out that one of our favorite pornstars was performing at a strip club nearby, and we decided we needed to go and see her. It was my first time going to a strip club and I was definitely nervous, but it also felt kind of empowering. Sex work is work, and I respect the hell out of it. We got there super early and, after some discussion, we decided it would be fun and adventurous to get a private couples dance.

We talked with her for a while out on the floor before heading back into a private booth together. Some highlights were chatting with her about life in Los Angeles, seeing my partner's face light up when she touched me, and when she saw my tits and said, “Oh my god, these are yours, aren’t they?!” It was definitely an experience I won’t forget.

Would I recommend it: Honestly, I think it depends on your relationship. As someone who’s non-monogamous, sharing my partners sexually and even romantically is something I’m practiced at. I loved getting to share my partner with someone else and support sex work at the same time. However, I would definitely say to make sure that you and your partner are on the same page before going forward with it. Is one of you just doing it to make the other one happy? Cause that’s a bad idea. This is one of those things where you both need to be enthusiastic participants, otherwise, it’s just going to be awkward for everyone involved.

Having multiple threesomes

I’ve lost track of how many threesomes I’ve had, but if I had to venture a guess, it’s probably around 12 or so. Not an all-time high, but definitely a respectable number. I’ve partaken in threesomes that involved two men and one man and another woman. A few were fun with moments of just ok, but most of them were pretty great. I love getting to experience two different, wonderful people at the same time.

For me, the best way to ensure a successful threesome is to be aware of the dynamic. Spend a little time hanging out together before you get into it and make sure everyone is on the same page. There’s often going to be a little awkwardness, that’s just how it goes, but if the dynamic is right, you should be able to move past it fairly quickly.

Would I recommend it: Yes, absolutely — with the caveat that not every three-person dynamic is going to translate well to a threesome. Again, it’s all about feeling things out.

Flirting with people out at a bar with a partner

I practice non-monogamy, so flirting with other people isn’t a forbidden thing in my relationships. In fact, in a lot of cases, it’s encouraged. There have been a few times where I’ve been out with a partner and we’ve met people who one or both of us found incredibly attractive, so we flirted, sometimes together and sometimes separately while the other person watched coyly from another conversation. I’ve watched a partner get someone’s number in my presence and vise versa. For us, it brings us a lot of joy watching each other act on our attractions to other people and seeing those flirty smiles.

It’s definitely not for everyone — but I’m damn glad it works for me.

Would I recommend it: Only if it works for you. If you and your partner are flirting with the idea of flirting with other people, make sure you have a lot of conversations about it beforehand. While it’s happening, keep checking in with each other. Don’t just assume things are fine. Stay communicative. If it’s something you love the idea of, though, and you both think you could handle it, then yes, I very highly recommend it.

Having a foursome

I’ve only had a foursome once, and it was with three other people with who I was already very close. The other woman and I hadn't hooked up yet, but every other combination of hookups within the four of us had already happened, so it was a sexual situation we all had at least some familiarity with. She and I were pretty nervous, and we showed up around the same time and walked in together. We were figuring the four of us would probably hang out for a bit beforehand, have some drinks, and ease into things — but as soon as we walked in, the two guys were ready to go. So, we did.

Sometimes it’s weird hooking up with your friends, but in this case, it wasn’t at all. The four of us had a pretty fluid dynamic, and we all had a really great time lounging around naked together. Sometimes we all fooled around together in a group, sometimes we split off into pairs, and sometimes three people would play while one person would watch (and maybe film it with everyone’s consent). We just went with whatever felt right in each moment.

Would I recommend it: Yes, 100%, but again, be mindful of the dynamic. I will say that foursomes can actually be a little easier than threesomes because there’s an even amount of people involved. More people can in theory be more overwhelming, but it can also help dilute some of the awkwardness by having the ability to pair off if you want to.

Going to sex parties

To date, I believe I’ve been to five sex parties. The pandemic put a stop to that streak for now, but as soon as it’s safe and comfortable again, you can bet I’ll be back at it. I went to my first one with a guy I met on OkCupid for our third date, and I loved it so much, I just kept going back and playing with the same group. There were usually anywhere between 10 and 30 of us, hanging out in various stages of undress in a hotel room and having lots of enthusiastically consensual sex. What could be better?

Would I recommend it: Yes. Yes. Yes. For me personally, sex parties are so empowering and validating. I’m an exhibitionist and I practice non-monogamy, so being in a space where I can just be naked and express myself sexually in whatever way feels most comfortable in the moment is oh so lovely. I’m sure sex parties aren’t everyone’s cup of tea and not every group dynamic is going to be perfect, but if it’s something you’ve ever wondered about, I can assure you that they’re definitely worth a try.

Using a sex swing

I met a guy at a non-monogamy meet-up one night and we immediately vibed super well. He mentioned where he lived and I was hesitant because it was a bit out of the way for me. Then he mentioned he had a sex swing — and I was like, yeah ok, I can swing it (pun very much intended).

We didn’t see each other for very long, but the experience of dating someone who had a sex swing was super interesting and unique, and it’s still a story I love to tell. Being in a swing while having sex is a bit of a balancing act, but I’m glad I got to try it out at least a few times.

Would I recommend it: Honestly, I could take it or leave it. It’s one of those things that might be a little overhyped. It’s also possible I would enjoy it more with a different kind of sex swing or a different partner. It was very novel, but maybe not something I need to experience all the time.

Hooking up with roommates

In porn, a lot of the “roommate” scenes tend to be about one person hooking up with their partner’s roommate without their partner’s knowledge. For me, that’s not how it went down at all. I started seeing a guy in a non-monogamous capacity and was immediately attracted to his roommate as well. Before long, I was hooking up with both of them — sometimes separately, sometimes at the same time, and sometimes with one while the other one watched. What can I say, we liked the variety.

Would I recommend it: Only with the right dynamic. Before you initiate this kind of situation, make sure everyone is very squarely on the same page. Have a conversation about what might happen if you stop seeing one roommate but still want to see the other. Make sure everyone’s thoughts and feelings on the subject are very clear. This kind of dynamic can be insanely fun, I know it was for me, but it can also be a fragile situation if you’re not practicing very open communication.

Meeting a pornstar

I’ve met favorite pornstars of mine on a few different occasions, but the one that sticks out the most and is a bit more sexual in nature is the time I went to see a pornstar I like perform at a strip club, and she ended up making out with me while she was on stage. Afterward, we got to talk for a bit about how much she loved her job, and interacting with her on that level was honestly my favorite part of the experience. I’ve also hooked up with a couple of men who work in porn at various sex parties I’ve been to, and talking with them was always a wonderful experience as well.

Would I recommend it: Yes, as long as you recognize that sex work is work and these people are humans just like you and me. Yes, they have sex on camera, but that doesn’t mean you’re entitled to cross any boundaries they’ve set. It’s fun to meet people you’re attracted to and admire, and asking them about their line of work can be super fascinating. Just remember, porn is only their job, and there’s a lot more to them than just that.