Asking male friend for casual sex

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I'm a female in my mid-thirties. I've been single/celibate for over a decade (mainly disinterest and I like being alone). Recently, I've begun feeling the urge to get back out there, so to speak, but am pretty anxious and overwhelmed due to the time that's passed. I have a single, older male friend whose personality I find attractive; we always have a good time together. He's pretty similar as far as intimacy/relationships go - doesn't get around, loner. There's not much to complicate things that I can see - no kids, no exes, no health issues (mental or otherwise). Not looking for a full blown relationship here, but I feel comfortable with him. Maybe a safe bet? What do you think? How should I proposition without coming off as desperate, or scaring him off? Should I bring it up at all?

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@jft7,

Short answer, yes! You should have sex with him. In middle age, casual relationships are normal. Go for it.

You could ask him directly. I would say yes if you are reasonably attractive and I weren't dating someone else, but it would be awkward and seem contrived.

Why not just have a normal fling? You flirt with him, make sure he knows you are interested. Have dinner, and then invite him to your place or ask him to invite you.

Sex should be fun. We all understand casual relationships, and we are all playing the game. Just go for it.

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@jft7,

Do you have any sexual interest in him? at all?

I can't imagine ******* someone I have zero sexual interest in.

__

Is he someone you can laugh with? Talk to him. Find out how he feels about fwb in general before suggesting it as a specific option for the two of you.

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@ehBeth,

Sure I do. Wouldn't consider the thought if I didn't, though it's taken a long time for me to get to this point. He's good company; funny and a decent person - little odd, but so am I. We have fun.

Thanks for the advice. I'll work on that.

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Are you getting any vibes from him that he wants to go into another level with you?

You could lose a friend if this backfires.

Start flirting and see what happens. If there’s no response, back off and find another lover somewhere else.

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@PUNKEY,

The fact he shows up every single time we plan something together, is genuinely excited, then will walk me home (out of his way), spending ridiculous amounts of time talking when he could just go home gives me some indication. He's not the type to give his time away, and he's not a touchy-feely person (neither am I), but with me, it's different. He will touch me/hug me, and doesn't recoil if I do the same. Still, based on the responses here, I'll keep feeling it out.

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@jft7,

He is a typical middle aged nice guy. It's quite simple, he just needs a little pronpting.

The next time he walks you home, invite him up for a drink. Offer him a seat on the couch and sit next to him. If he doesn't make a move then, tell him you are cold and want to snuggle, or just kiss him.

If he isn't interested, he will refuse your invitation no big feal. Middle aged people don't judge

Most likely he will get the hint and the dance will start.

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@jft7,

jft7 wrote:

He's good company; funny and a decent person - little odd, but so am I. We have fun.

Thanks for the advice. I'll work on that.

sounds good Smile

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@jft7,

Why not? You should feel free to feel good. I don't think you sound desperate and he shouldn't get scared. Just stay safe and go for it.

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@jft7,

Just remember to use protection,venereal diseases are common.

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@jft7,

As the older man I had a quick fling with a woman 20 years younger. I asked why she would and she told me she was comfortable with me and trusted me. It was some of the most amazing sex I ever had and she told me I made her whole body tingle. I actually had to google that and it is a thing. Don't worry about the time off. Be upfront and ask. If he spends time with you when he could be doing something else I would just about guarantee he would be happy to oblige your desires.

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No,it's not like that.

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@jft7,

Given that you have been celibate for so long mainly because of disinterest, then a casual sex relationship is better, because what happens if you suddenly start feeling disinterested again? Men are not like a garden tap that you might turn on once or twice a year and forget about the rest of the time.... unless its a casual arrangement!

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@mystikmind,

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@jft7,

That's putting the benefits before the friendship. You may have started out thinking that the FWB label was a good idea, but since the territory can be so uncharted, yours and your friend's feelings may change in myriad ways, and the label can quickly become a hindrance.

Asking male friend for casual sex

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