How to do casual sex?
October 2, 2016 2:11 AM   Subscribe

I'm interested in exploring my sexuality with multiple partners. (37, F, straight-ish). However, I'm a sensitive, over-thinking type with a moderate case of vaginismus. How do i find patient and understanding partners?

I don't have much sexual experience, for my age. What happens of late is that i mentally want to have sex with a guy, but physically i freeze up and detach. I used to think this was because i was looking for something more serious but upon reflection, what i really want is to explore and get comfortable with my sexuality before i find a partner. I do have a healthy sex drive; i masturbate frequently and think about sex. But i can never get comfortable when it comes to a partner and I've never really had satisfying sex with a partner.

I've gotten a pelvic and vaginal ultrasound and everything checked out normally. I am able to be penetrated but it usually needs to go in slowly and i need to feel comfortable. I think that working with understanding partners and learning how to have fun with sex can help me to enjoy sex.

However, how do i find people like that? I'm on tinder and ok cupid and don't have a problem matching wi th interested men. However i am at a loss about a.) How to explain my situation to them, and b.) How to find men that are patient enough.

The other thing about me is that i am quite emotionally sensitive and i get emotionally connected to people through sex. However, I'm not ready for a relationship just yet and want to try exploring with multiple people first. Make sense?

Would love some ideas and guidance for how to go through with this: satisfying sexual exploration wi th an understanding partner.

If i could afford it I'd find a sexual surrogate or similar but surely there are men who are interested in this not as a job?

If it's relevant, im decently attractive and don't really have a hard time finding partners. (Esp. Online; im shy in person though )
posted by anonymous to Human Relations (11 answers total) 9 users marked this as a favorite

Mod note: Just to quickly forestall potential confusion re the first sentence: pretty sure OP is just asking about non-monogamous relations, not, e.g. threesomes, etc.
posted by taz (staff) at 2:12 AM on October 2, 2016 [1 favorite]

Seems like OkCupid would probably work fine for meeting a guy who takes his time with you, especially if you convey that, at least from what female friends and family have told me.

I think, if penetration is problematic, you might want to try receiving oral sex, which seems to be an easier way to reach orgasm for many women.
posted by gryftir at 3:05 AM on October 2, 2016 [1 favorite]

The other thing about me is that i am quite emotionally sensitive and i get emotionally connected to people through sex. However, I'm not ready for a relationship just yet...

This sets off some loud warning bells... It makes me wonder if what you're actually looking for is the connectedness/closeness, and the sex is just the vehicle.

That you are self-aware enough to articulate this point makes me think it needs a bit more attention. Asking "How to do casual sex?" translates (to me) as "How to do non-emotionally attached sex," which, if your propensity for forming attachments with partners is anything like mine, means you are in for some unhappiness. Someone who describes themselves as "quite emotionally sensitive" is not, IMO, someone who is going to ever be "good at" casual sex in the manner you're hoping to be.

I apologize if I am reading you wrong. I definitely understand wanting sex for its own sake, and the sheer physical experience. it's a tough row to hoe, and one that can be deceptively easy. Please be careful and guard your heart.)
posted by I_Love_Bananas at 3:25 AM on October 2, 2016 [14 favorites]

I'd try asking for it upfront before meeting someone. Straight out say that you're looking for someone to help you learn about your body, and you'd like that to be the focus of your activities. You'll get fewer takers (and don't take that personally!) But you're likely to find some people who are into it. Then you'll need to audition them of course, and some will be good and some won't.

Demographically, you may have good luck with poly men and with younger men without a ton of experience who will find it an ego trip, though the latter tend to be less skilled.

Avoiding emotional connections may be especially hard given what you're looking for... you need sex with lots of communication and time, which tends to develop more intimacy than quickies. And you want it to be ongoing so sticking with one-offs from out of town won't work. You could try to focus on people you couldn't take seriously as a relationship partner. Depending on your criteria, that could mean someone significantly older or younger, someone who's married, someone who lives with his parents, someone with vastly different political views, etc.
posted by metasarah at 5:14 AM on October 2, 2016 [1 favorite]

I agree with I_love_bananas - are you sure this is what you want? Casual sex is a catch-22; if it's really good, it's easy to get emotionally attached. If it's bad, why bother?

That said, older men will be much more patient. I wouldn't bother with anyone under 40.
posted by AFABulous at 8:37 AM on October 2, 2016 [3 favorites]

You are going to do yourself and your partners and your headspace a huge favour if you stop thinking that sex = penetration.
posted by DarlingBri at 9:56 AM on October 2, 2016 [5 favorites]

Hi anon, I'm not sure if I'm reading your question right, but I want to try and relate.

In my earlier 30s, I tried what you're trying here... it wasn't for me. The superficial nature of casual sex, and then especially men's attitudes towards women that comes along with it, just simply isn't for me. It was worse than being alone -- it made me feel the pain in my heart over not getting my actual needs met even worse. Plus the quality of the sex was so utterly abysmal the result was not having much desire to return to this western practice. It probably didn't work for me because similar to you, I'm a real and emotional person in relationships -- not a taker or user.

The downside: it sure made me angry at men who obviously want connection too, but are way too messed up to ever admit it that's part of the reason they're there (and then have the nerve to critique your inability to be a perfect sex partner from scratch for them, as if you're supposed to fire up automatically, like a john deer pornstar or something). It just seemed like a world of hurt, and all a woman is doing in pursuing the same thing is brutalizing her heart and soul in the way patriarchy has taught men to. It is a pathetic failing of modern society that women have to wait until their 30s to improve this relationship with their bodies (that is highly forbidden throughout the previous life stages), while men supposedly don't improve their emotional relationship with Self until a similar life stage (you know, until after some horribly immature soul-destroying breakups in their teens and 20s, maybe some date-rapey rebounds, and ultimately treating the best of young women's hearts like a reflection of their inner feminine which has already been trashed by the older generations of men 'mentoring' them).

You're not wrong or a bad person to want a better understanding of your own sexuality. I really feel your pain when you say you've never had a satisfying sexual experience with a partner. I don't know. I would just caution that if you're going to do this, be real about everything you want from the experience -- especially to have your feelings respected and to not be criticized for learning. Tread lightly.

One more thing:

i mentally want to have sex with a guy, but physically i freeze up and detach.

Based on this, I strongly suspect that when you encounter someone who is excited enough about you to not rush it -- and even better, who wants to watch for your cues so that you're not rushing it either, who is willing to understand that women get feeling trapped in their bodies with their sexuality and how to decode it too (not so different from men afterall)... Under those circumstances of patience, being actively listened to, emotional attunement and genuine concern for the quality of your experience, might you find the satisfaction you've been hungering for. You have my permission to ask for what you really want, and my encouragement not to settle for less. Best of luck!
posted by human ecologist at 12:52 PM on October 2, 2016 [8 favorites]

Try this book: "Come as You Are" and peruse the author's excellent blog. Emily Nagoski is a sex educator who makes recommendations based on actual research. I learned a ton from her, and I was already having all the sex with all the people!

I am at a loss about a.) How to explain my situation to them, and b.) How to find men that are patient enough.

Your situation is extremely common and totally normal. Feature, not bug! You take charge and you trumpet it loud. "I'm looking for a patient, understanding playmate who wants to pleasure me orally and focus on creative, stimulating, non-penetrative sex. I'm a bit shy so I want someone who will draw me out AND respect my boundaries!" You're not looking for Regular Joes who will indulge your special request (and stop thinking that, you're entitled to your fair share, girl!) You're looking for Finicky Freds who WANT what you've got and are EXCITED to help you unwind.

Decide ahead of time that any partner who doesn't meet these criteria gets the sack. You're here to explore, not to coddle or teach! That super cute goofy young man who tries to eat you out but fucks it up then goes in for the bone? HELL NO. The older professor who strokes you so gently, but keeps pushing for anal even when you've already said no? FUCK HIM! (I mean not literally.) Keep moving on. And when they text you afterwards wanting more, you say "Once was enough. Thanks!" Delete number.

For your part, don't just sit back. It's your responsibility to be vocal and clear about your desires in the moment... that means letting your partner know what you're feeling, good AND bad, and how you want to be toyed with. "A little to the left! Softer! This isn't my favorite, let's try... Oh, oh, fuck yeah!"

Don't forget to get tested, check your partner's status and wear protection. Skip the sleepover and brunch combo if you're having too many feels. Oxytocin's a drag :)

Pro tip: jack off in session.
posted by fritillary at 2:00 PM on October 2, 2016 [4 favorites]

I did this during my divorce. I wasn't specifically looking for it. I just spent a lot of time online, very frequently logged into a chat program. I was willing to talk with anyone who wanted to talk with me and who wasn't promptly an asshole to me.

Many of these men initially contacted me through the chat program, but not all of them. I also met men who were a friend of a friend. I kept most of these relationships online (and by phone in some cases). I met a few of them in person, but most of these relationships stayed online. One unintended consequence was that the primary emphasis of these relationships was emotional, though they were very sexual relationships in some cases.

Older men are generally a better bet, but not always. You want intelligent men with some experience. Experience and age do not always correlate. The sweetest guy I knew was actually several years younger than me, but far more sexually experienced than I will ever be. He had gotten around.

I was in no way looking for anything. I just was willing to talk with people. I sometimes talked for some weeks with someone before it came up in conversation that I was facing a divorce and then he would change his tune as to what he desired.

I am just very open and honest and tend to lack a specific agenda. I just like talking with people because they are people and that is all there is to it.

The thing that seemed to work the best was learning how to tell my story in a way that did not put any expectation on them. So I learned to talk about the fact that I had been sexually abused as a child and I was going through a divorce and I let them decide how they felt about all that and whether or not that was too much baggage for them to deal with.

Some men really seem to like playing hero and envisioning me as their damsel in distress. This is actually something that dogs my heels to a degree that I find aggravating because I have several years of college and a good GPA and for a time I had a job at a prestigious company. I am a competent human being. So the degree to which men just want to frame me as a helpless victim that they can swoop in and rescue is problematic in my eyes.

The point I am trying to make is that whatever personal issue you have, some men will see it as a feature, not a bug. Some men will get something out of being the guy that helped you with your sexual issue or being your shoulder to cry on or whatever. The trick is to learn to communicate that you need a shoulder to cry on without coming across like you are trying to impose on them in specific.

I just learned to divulge information about myself in as neutral a fashion as possible and let men decide what they thought and felt about that. I let other people's reactions be their responsibility. If they were all "Nope, I am outta here!" that was totally fine. I didn't need to waste my time on them. If they were interested, I accepted their interest if I didn't have a problem with them.

I only worried about if I liked what they had to bring to the table. I let it be their decision if they wanted something I had to offer. And any time I asked, every single man had a different explanation as to what was "hot" about me. There was no one thing that did it for all of them. What they noticed about me said as much about them as it did about me.

I did make the conscious decision that the first guy I had PIV sex with during my divorce would be someone that meant nothing to me. This was not at all difficult to arrange. Doing it that way really helped me not get all bolluxed up over sex + feelings = WE MUST GET MARRIED OR SOMETHING!

My experience has been that men crave feelings as much as I do. What they don't want is a ball and chain. They don't want that "I have feelings for you, so here is the prison you must live in and I have already picked the wedding date."

I am probably saying that really badly. My point is that men I have known craved emotional expression in the context of sexual connection as much as I did. What they did not want was some heavy expectations placed on them just because feelings had happened. If you view feelings more like a theme park ride that you can enjoy and not some sort of evidence that we are fated to be together for all eternity, that seems to work better generally for all parties.

I am the marrying kind. From my end, I had to routinely remind myself that X, Y and Z were in the way of me committing to anyone. It just wasn't realistic for me to "get serious" with anyone. This in no way prevented me from spending the kind of time with some men that is typical of a serious relationship.

It might help to journal to sort out your thoughts and feelings. Some of the issue here is a case of mental models -- that spending X amount of time with someone or having big feelings or some other specific metric = "this must be A Serious Relationship" (by whatever definition you use for real/serious/committed relationship). Several of these men did talk about wanting to marry me. It just wasn't possible. My divorce wasn't even finished and many of these men were in foreign lands.

So, (assuming your internal landscape is anything like mine) define some conditions or parameters or identify why a serious relationship is not on the table and any time you start feeling like "because of x, this has to be A Serious Relationship," remind yourself of the limitations or conditions that dictate that you aren't committing to anyone and then stick with your guns and sort your feelings.

posted by Michele in California at 3:02 PM on October 2, 2016 [5 favorites]

I will add that I made a concerted effort to cleanse my language of commentary that described specifics about past partners such as age, height, profession, educational attainment, hair color, eye color, physical build or any other details that could be interpreted as indicative of my "preferences" in men.

This was something I kind of A/B tested and found that if I talked about (for example) the fact that my husband was blond, then blond men thought they were a shoo in and brunettes thought I was rejecting them, basically. Prior to this experiment, the majority of the men I got involved with had specific traits in common, such as about 3/4 of them being blond. After making sure to cleanse my language of such details about past partners, the variety of ages, ethnicities, professions, hair color, etc. went up dramatically.

So, it might be helpful to you to NOT comment on "most of my partners have been insensitive boors" or whatever. Talk ONLY about "I have a moderate case of vaginismus, thus I need especially patient and understanding men" and that sort of thing. As much as possible, say nothing at all about past partners. Only describe your current situation as neutrally as possible.

Refraining from injecting your expectations based on past experiences makes it vastly easier for people to just be themselves and thereby surprise you by being not like every other past partner you have ever had. Talking about your current situation -- "I tend to freeze up in x situation and I don't know how to get past that" -- gives people the information they need to know to not make some horrible mistake and empowers them find approaches to the problem that would never occur to you.

If you present it as your problem and be matter of fact about it, a lot of people will be happy to problem solve and take some glee in rising to the challenge and being the first person to do X with you or whatever. It's problematic if you get all blamey and accusatory and start with an assumption of guilt on their part because of your baggage. But I have found it to be not very problematic to just own it as my own baggage that existed before I met them and let them figure out how they wish to navigate it. This has a long track record of getting me surprisingly good results.
posted by Michele in California at 4:01 PM on October 2, 2016 [2 favorites]

You may want to focus on people who are already in non-mongamous relationships, in that part of having one of those be successful for any length of time is being receptive and welcoming to feedback about needs and preferences. Also, Nthing "sex != penis-in-vagina".

Also, maybe there is a single male in your friend circle who might be interested in expanding your relationship with them to include sex play? Perhaps it would be easier for you with someone you already have an emotional (but not specifically romantic) connection with?
posted by softlord at 12:53 PM on October 3, 2016

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