Casual sex/Friends with benefits?

[KittyPink]

So, I've come along awhile and figured some stuff out.

So, I'm good to have sex in my opinion. I know how to have it comfortably, now, with less gender dysphoria. But like I want to have sex for my first time, but I don't need to lose my virginity with someone who I'm in a committed relationship with. (I'd prefer it, but I don't require it.) I don't know how to ask or initiate a conversation about having sex with like a friend or something like that. So I dunno? Advice would be appreciated?

[Sam W]

Hi KittyPink,

It sounds like you're already thinking about what you are and are not ready for or interested in when it comes to sex, which is a great first step (it may also help to define for yourself what losing your virginity looks like, since that's an idea rather than a concrete thing, and can mean different things to different people). In terms of talking about this with potential sexual partners, is there a particular person (or more than one person) who you have in mind as someone who you'd feel comfortable and eager being sexual with? Or is it more that you want to be sexual and are looking for the right person to do that with?

If you haven't already read it, this article has a lot of good advice on how to navigate casual relationships in a healthy way: Casual...Cool? Making Choices About Casual Sex

[KittyPink]

Hi KittyPink,

It sounds like you're already thinking about what you are and are not ready for or interested in when it comes to sex, which is a great first step (it may also help to define for yourself what losing your virginity looks like, since that's an idea rather than a concrete thing, and can mean different things to different people). In terms of talking about this with potential sexual partners, is there a particular person (or more than one person) who you have in mind as someone who you'd feel comfortable and eager being sexual with? Or is it more that you want to be sexual and are looking for the right person to do that with?

If you haven't already read it, this article has a lot of good advice on how to navigate casual relationships in a healthy way: Casual...Cool? Making Choices About Casual Sex

To be honest, it's kinda confusing for me, virginity to me means like literally nothing, I just see it as an arbitrary descriptor of how much experience someone has with sex. There's a couple people I wanna ask, mostly all friends, which I happen to be comfortable talking about sexual stuff with. But like I haven't asked any of them about a friends with benefits / casual sex relationship. I'm not having sex with total strangers for personal reasons, so hook-ups are out of the question unless I know them a little.

[Siân]

Virginity IS a weird concept, I totally get why it's confusing. I mean, we don't have a special word for someone who hasn't done literally any other kind of activity. Even as a placeholder for sexual experience it doesn't tell us that much, since one person might have a whole bunch of sexual experience but consider themselves a virgin due to the types of sex they were having, and another might have just once experience and no longer feel that they are a virgin.

Perhaps a more useful question - and I think what Sam was getting at - is thinking about the kinds of things you'd like sex with a partner to involve, and what that means to you.

In terms of asking people if they're interested, I think probably the best thing to do is just ask in a really simple way that gives them space to say yes or no. If they are a yes then you can go on to talk about the specifics (more here: Be a Blabbermouth! The Whats, Whys and Hows of Talking About Sex With a Partner). The important part, I think, is to be ready to hear a "no" if that is their answer. How do you feel about that?

[KittyPink]

I mean my first time, I wanna do some kinky stuff, but I don't think I want everything I'm interested in the first time. And I also would prefer to receive penetration and stuff, but I'm open to other things. I'd want a little bit of foreplay, and more likely than not, I'm going to require aftercare and maybe post-sex cuddles.

[Robin]

It sounds like you're pretty clear on what you want.

You've mentioned several specific needs and wants, as well as a few things you might or might not end up wanting.

Do you think you'd feel comfortable telling your wants and needs, just like you did here, to any of the friends you mentioned in your previous post?

[KittyPink]

Yeah, probably, I have no problem with discussing with friends as it's not much different between talking about sex with them vs my sexual wants and needs in general.