Asking for a Friend (with Benefits)

[sexpositivity94]

Hi,

First I want to say how much this site has helped me through the years. I've asked questions that have received awesome answers, but just reading the site's articles and answers to other people's questions have been invaluable in my life. I feel secure knowing I have a resource I can fall back on for help.

I'm a 23 yr old cis girl in college. I'm a "virgin" (which Scarleteen has helped me navigate, come to terms with and see as no big deal, and something I'm no longer self conscious about). My question is about asking someone to be a friend with benefits. There's a few different questions that need a little backstory first:

The person I'm thinking of asking (let's call her M) is a 20 year old trans woman who I know from college. I am the treasurer of the club that she is President of (our campus' Transgender Alliance). While I don't know if I'd call her my best friend, we are certainly very close friends and our physical (platonic) intimacy is definitely some of the closest I have with anyone. We cuddle regularly, we've spooned, and we touch/kiss each other on the face. We are super comfy with each other.

She knows I've never had a sexual experience with another person before (my sexual frustration is a running joke in our friend circle ) She also knows I'm not interested in a romantic relationship, just a physical one that hopefully also comes with friendship. I would be comfortable asking her (and I am to a point), however, we had one conversation back in November/December that gives me pause. We were talking about relationships that we would want and I talked about wanting something casual (more like an FWB, with a bit more F than B). She voiced her support of my wishes; said it sounds great and that she doesn't know/think she would ever be capable of that. It didn't seem like she was shutting down the possibility of me asking her, but she told me how her physical relationships are based in romantic feelings and loves romantic relationships (she's poly and bi. I'm bi and not sure about the poly/monog thing. Also I'm not fully aro, just romance indifferent right now).

What complicates this, however, is that at the time of this conversation, she was in three loving, committed relationships with people she either loved for a long time or had growing feelings for. Two months later, in January, she lost all of those relationships in the course of 2 weeks. It was really rough for her. She seems to be better now (I would never ask if she wasn't) and at the present moment she is in no relationships. However, we have been bonding over our shared sexual frustration. She hasn't had sex in a long time (for her)- even before her relationships ended, she hadn't been active with her partners for a while) and she and I joke about just being straight up horny and our humorous/unsuccessful masturbation stories, etc.

I was thinking, in the next few weeks, of asking her if she would be interested in starting an "arrangement" like the one I described above. I have been going over what I might say, and I came up with something like this.

"Hey, can I ask you something? I just wanna warn you, it's personal. And please be honest with me. No matter your answer, you absolutely won't hurt my feelings in anyway and if you don't want to talk about it, we just move on like it never happened."

Then if she is open to discussing it, I would say something like:

"I consider you one of my closest friends. I'm super comfortable with you. You know that I'm looking for a physical, more casual relationship, and I know we both have been kinda frustrated lately, so I was thinking, what would you think if I suggested us starting a friends with benefits type thing?"

If she says no or hesitates or just isn't into it, I'd be like

"That's totally fine. I was just asking because I know we're really comfortable together. Don't feel bad about it. It's totally cool. Resume Friendship." and then I'd ask her if she wanted to get some food or something, to lighten the mood.

If she says yes or wants to think about it, I would start communicating with her what we both want out of it or answer any questions she may have. It would hopefully be an ongoing discussion.

Now that I got ALL that out of the way, I have some questions:

1) Knowing the conversation we had in November, do you think I should even broach this subject? Or is it insensitive after she said that's not something she would want or be able to do. (I'm only asking her because her situation has changed).

2) Do you think it is (or would come off as) exploitative, like I'm using her being single and sexually frustrated as a "solution" for my "virginity"/sexual frustration.

3) If it isn't, but still could come off as it, how can I present it as I intend it (as a mutually beneficial thing)?

4) If all of the above is good, and I do go forward, are the scripts that I drafted adequate? Am I missing something I should include or am I including too much?

I apologize for my extremely long post. I also overthink things a lot and have been debating this for over a month, that's why the post is so comprehensive. If I'm going about this totally wrong, or if I can improve in any way, please let me know. Any advice would be appreciated. <3

[al]

Hi there sexpositivity94,

It's great to hear that Scarleteen has been so helpful for you over the years.

So it seems like you've already done a lot of thinking this situation through, which is usually my first advice to anyone who's considering what it might be like to introduce potential romantic and/or sexual stuff within a platonic relationship. I usually ask them to try and consider all the different possibilities- what if this person says no? What if this person says yes, but on slightly different terms? What if this person says yes, but the experience turns out to be less satisfactory than you expected? What if this person says yes and you love it and end up developing deeper attraction/feelings than you anticipated?
So I think you're off to a really good start in that you've already asked yourself a lot of these questions.

In terms of your specific questions to us,
1) I don't think that it's insensitive for you to ask this - what you're essentially doing is checking in about what she wants. Even though M said that she didn't think she'd want to be a part of a casual/FWB situation back in November, like you said, her romantic/partner situation has changed since then. Also, people's attitudes about who they're attracted to, what kind of relationships they want to engage in, and the emotional depth of those relationships is a pretty fluid thing, especially in younger years. You might even bring what she said in November up - "I know a while ago you said you wouldn't be into that kind of thing, and I was wondering if you still feel that way". Asking someone how they feel/what they're comfortable with is the best way to begin a romantic and/or sexual experience!

2) What makes you worry that you're being exploitative? In what you planned to say to her you address your reasoning as to why you thought of this, and you say that you're both fairly comfortable with each other, that you are both experiencing a good amount of sexual frustration, you're fairly physically intimate already, and so on. It's not as if you are falsely suggesting that you want to be her committed partner while only really wanting to have sex with her. That's a situation that wouldn't be okay, rather than here, where you're literally asking about what her needs/wants are to see if they match up with your own.
As for the virginity part, it seems like from what you said earlier, you've come to terms with the fact that not having had whatever type of sex you think of as a "virginity-ending sex" is nothing to be ashamed of. If it's not about shame, is virginity playing any significant role here? I think there's a big difference between you saying "I need to lose my virginity because I'm embarrassed and I don't even care who it's with, so it might as well be you", and, "I haven't had sex before but I would really like to, and I think I would like it with you".

3) That being said, people are unpredictable, and there's always the risk that the person that you bring this up with is not receptive to the idea. But, you being the thoughtful and smart human that you are, have already thought about what you'd do about it. And the response you came up with was awesome - if M were to say she wouldn't want that/wouldn't be comfortable with it/etc, you respond by validating, respecting that boundary, and moving on. I think that's perfect! It's hard for me to imagine anyone getting mad about you asking about their wants/needs and then fully respecting the choice they make, even if it's turning you down. I would encourage you to think about what it might be like should that be the case - there may be a little bit of awkwardness afterwards. But, like you said, food! Playing it cool and demonstrating that you're still there for your platonic relationship and that things don't have to be weird just because she said no makes you a really good friend and helps smooth out any tension that she might feel. And know that, if things do feel awkward, it's okay, and as long as you keep being respectful and kind, it will pass!

I think what you've come up with is awesome! The only other thing I might encourage you to think about is this response to this question: "Hmmm. What would that look like?"
Whenever I'm figuring out wants and needs in relationships with others, I find that being as specific as possible really helps (or at least having those specific ideas in mind). The Friends With Benefits title is a pretty loose one, so it's up to the people in that relationship to figure out what that looks like - (We get together and hook up, but don't see each other outside of that, We are very close friends and sometimes snuggle/kiss/mutually masturbate/whatever, We hook up with each other but don't talk about any other people we're dating/hooking up with, etc.). I guess what I'm saying is that she might ask what exactly you're suggesting or thinking of, and that you might want to think a little bit on that before starting that conversation.

Those are my immediate reactions to those questions. Thanks for reading my long post!