I Prefer To Date Women, But I Want To Try Sleeping With A Man.

How do you ask a guy friend to sleep with you? I used to date guys but figured out a few years ago that I would much rather be with women. I am 30 and have never slept with a guy. It’s something I want to do, just to try.Guy friends have offered. My issue is they think either I just need a good guy to convert me (it will not happen) or they want a relationship. I don’t think I’m that much different from straight women in that all I want is to be taken as I am and have what I say, be taken for what I mean.

Also, I’d really rather this experience be with someone I know, but at the same time, I keep wondering if someone more anonymous would just be much less complicated. I don’t quite know who best to approach, set the expectations and trust that I would like and then go about asking for thisfavour. J

This is why I keep blogging, y’all. And while I don’t profess to be a sex expert (hopefully my wife disagrees), I will do my best to earnestly tackle your question. No snickering. (Snicker) Okay, so you pretty much want the same thing that most men want, sexual experience, with no strings attached, with someone who is familiar and safe and attractive. Yeah, it doesn’t work like that. So let’s parse out your options, from least feasible to most feasible:

Throw a dart in a crowded bar, and you’ll hit a guy who is willing to sleep with you. If it doesn’t sound ideal because it’s, well, random sex understand that there are tradeoffs for wanting to use a man like a disposable human dildo.

Male prostitutes – I think Heidi Fleiss started a stud farm in Vegas. Seems a long way to go and a pretty penny to pay just to get laid, but, for a nostringsattached experience, you can’t beat a prostitute. (Correction: Heidi’s stud farm never actually got it up.)

Close guy friends -You already pointed out the problems. They think they’re going to convert you, or they actually want to date you. Both are fraught with danger because there’s an emotional set of expectations. Moreover, if these are close guy friends, don’t you think it could get kind of weird? Not just between you and him, but between you, him, and the whole crowd of people that know you. If there’s a guy that you actually don’t like, that would be perfect. Lots of women have pioneered the ‘sleep with someone you hate to watch him disappear from your life’, but I still think it’s too risky.

Random guys at bars – I don’t know how old you are, but I’m pretty sure it doesn’t matter. Throw a dart in a crowded bar, and you’ll hit a guy who is willing to sleep with you. If it doesn’t sound ideal because it’s, well, random sex understand that there are tradeoffs for wanting to use a man like a disposable human dildo.And this is where it really, comes down to you, J. Do you really just want to have the experience of screwing a man just one timelike the person who tries Ecstasy once just to say he did?

If so, I would think you’d go to a straight bar with a girlfriend, find the cutest guy you could find, and let nature take it’s course. Or, even more directly Go on Nerve.com, or Adult Friendfinder.com or SexSearch.com or even Craigslist Once again, it’s not hard to find someone to take your male virginity, it’s a matter of figuring out your comfort level with the whole process. If it sounds a bit cold, like Erica Jong’s ‘zipless fuck,’ well, that’s pretty much what you’re asking for. It’s certainly less complicated than being with a friend, no feelings or relationship to ruin.

…if any readers disagree with my advice, I’m all ears. Sometimes, the answers don’t quite come easily.

But if you can separate sex from feelings, and you’re not too creeped out by the anonymity of it (personally, I was) I say go for it. Talk to him first on the phone. Build up a comfort level. Use protection. Avoid snuggling. And make it clear that you’re out for a onetime good time. And if any readers disagree with my advice, I’m all ears. Sometimes, the answers don’t quite come easily.

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  1. 1

    This is going to be a fun thread 🙂

  2. 2


    Just ask.

    Men are not women.

    They will not want a relationship if you tell them ahead of time it is a one time thing for a curious Lesbian. They will not get attached. They will accept that you have not switched teams if you don’t ask them again and say “no” when they ask.

    Have fun!

  3. 3

    I don’t think I’m that much different from straight women in that all I want is to be taken as I am and have what I say, be taken for what I mean.

    This has to be the most mistaken statement I’ve read in this comment section. In *general* this is not true at all. Straight women want you to read between the lines of what they say and/or read their minds.


    “No, really. I’m *FINE* ”

    “I shouldn’t HAVE to ASK”


    No offense and good luck with your sexplorations 🙂

  4. 4

    Shouldn’t “sleeping with Lance” be listed on here somewhere? Also, I’m assuming J is a woman??

  5. 5

    @Lance, post #2

    Good answer!

  6. 6

    Walk into a bar. Go up to a guy you find attractive. Ask him if he wants to fuck. Repeat, if necessary. But you should be successful fairly quickly.

  7. 7
    Kat Wilder

    J, Evan is right it is very easy to find a guy online (Nerve is great for this) who wants NSA sex.
    It’s better than going to a bar (I believe) because you can pick the most attractive man (OK, I’m shallow), far from your hometown (this might be good; it can be awkward bumping into a hook-up at your local Piggly-Wiggly) and get to know a a little more about him without booze and other distractions. Like, is he safe?
    Yes, I have done that, but for different reasons. 😉
    Good luck!

  8. 8

    Personally as a hetero woman I can’t have sex with someone I’m not attracted to, so as a lesbian woman wouldn’t that be your first criteria? Picking someone that you wouldn’t be repulsed exchanging body fluids with?

    Since you feel doing this with your straight male friends could present problems afterward, doesn’t that lead you to doing the experiment with a stranger? And by definition there won’t be any trust (or positive expectations?) with a stranger. I just don’t see how you can have it both ways – the trust and comfortable-ness (as you would have with a friend), but with the assurance there would be no further expectations or awkward feelings on either part after the experience.

    I think you are going to have to decide which is the lesser of two evils. And perhaps in the process give more thought as to why you think you should have this experience… and why (and how much) it is important to you.

  9. 9

    If a hetero woman friend of yours wanted to experience lesbian sex to see what it was like, how would you advise her?

  10. 10

    All I’m going to say to the OP is that actions have consequences. @ Steve – you are wwwwaaayyyy too giddy over this, lol!!!

  11. 11
    Jack Strawman

    Life is short. Don’t grow old with regrets. If you really want something, go after it. Have a few drinks, quiet the voices, and take what you want…assuming he wants to be taken.

  12. 12

    @starthrower68, post #10

    Consequence: using a condom, problem solved.

    Yah, women talking about going out for NSA sex will definitely get a reaction from men. At least I didn’t offer my “companionship” like Lance did :).

  13. 13

    I think the person who said you should just do what you’d advise a straight woman wanting to experiment was pretty right on. Also, maybe you have a friend who doesn’t live in your same city/state that you could visit? Then you wouldn’t have to worry about how it would affect your daily interactions but could still get the comfortable-ness.

    I have a lesbian friend who went on Adult Friend Finder when she wanted to experiment with “straight sex.” She had tremendous success with it (actually, she did decide she liked both types of sex more or less equally as a result of the experience!).

    @Steve, #12 – there are lots of consequences, physical and emotional, that a condom won’t protect against. Though it is good to bring that up since lesbian sex is not nearly as risky as straight sex. And FWIW, from a year’s worth of personal experience, I HIGHLY recommend Lance’s “companionship.”

  14. 14

    I have turned plenty of lesbians into lovers of c*ck. Just kidding, no I haven’t. But I’m better than Adult Friendfinder and you NEVER have to worry about any sticky entanglements with the Lance Option.

  15. 15

    When I read the post, I was confused. Is J a man or a woman?

  16. 16

    Wow! I just discovered this blog a week ago and I can already tell I like it here 😉
    At the end of all of this, I think the guy you end up having sex with is going to be wanting to know how he did in bed. If you know the person, they are probably going to ask you about it. And what if by chance you didn’t care for it? That’s just awkward. At least if you sleep with someone you don’t know, you won’t have to tell.

  17. 17

    Some men drive hummers, SUVs or sports cars to “compensate”. FWIW, I drive a Honda Civic. Ahem! 🙂

  18. 18

    wow!! You get all kinds of questions don’t you Evan. lol!!

    I’d go with the friend option over the 1-night stand option. You aren’t going to know how you feel and there might even be some pain(although without knowing what you’ve actually done in the past that’s hard to say). You may not like it, or you may want to stop.

    Yeah, I’d definatley go the friend option, and if he’s a good friend, and knows the deal, IE you just want to try it one time then some blokes will be fine with that.

    A stranger in a bar? hmmm… I wouldn’t go with that option for your first time.

  19. 19

    Selena #8
    I agree with selena. I think it’s a better option to find someone online, get to know him enough to be comfortable with him and never see him again. 😀
    Why ruin a friendship for experience. I don’t think anything good will come out of it. And you might regret it in the end.
    And since you are not attracted to men i think it might be more awkward if you ask a friend, try it and still find it too awkward to go ahead with it.. It’s natural that you might not feel like doing it in the end since you wont be attracted to men. Think about what will happen after that?

  20. 20

    Wow, I thought J was a guy. But either way, there’s something about this letter that bugs me or just doesn’t ring true for me. [Full disclosure: Like Evan, I’m not a sex therapist, nor am I a lesbian, although I am female.] I suspect that nothing Evan and the rest of us suggests is anything J doesn’t already know. Which is what makes me think that what she really wants is permission to explore with a man. Which then makes me suspect — yes, I’m a suspicious sort — that she might not be as totally confident in her sexual identity as she wants us to believe. Like others have said, finding a guy who will turn down a NSA offer of sex from a 30-yr-old woman is really not one of life’s great challenges, at least not in this country. And why all the concern about up-front disclosures or guarantees? Sure, if J chooses to make it known to the guy that she’s a lesbian who’s just out to experiment, he mayarrogantly think he’s going to convert her (power of the penis, and all that), but so what? It’s not uncommon for men to have this belief, but I’ve never known a guy who, once he found out he was wrong, felt all that shattered and destroyed by it, turned into a small, weeping pile of woe at the foot of the bed. Har! No, more likely he says, “Oh well, at least I got laid,” and moves on quickly to more pressing matters, such as:” What’s in your fridge?” My guess is that J fears that maybe she’s actually bisexual and that she’ll have sex with a guy and …OMG….like it! Or feel attachment. Or feel confused. All of which will make life and future relationships more, uhm, complicated. Sorry, J, there are no for-sure answers here, and even purely experimental relatioships have the potential for complications. What can I say? That’s life, and it’s a jungle out there, but don’t let that stop you.

  21. 21

    J, I have the same issue, except I wish I was in your situation it would be so much easier. I’ve been in a monogamous lesbian relationship for ten and a half years, and now I’m 30 and I think my sexuality is changing. I really want to have sex with a man! I think about it all the time! But I love my girlfriend. So I don’t know what to do. If I were you I would jump on adult friend finder instantly and go cruising with no regrets. If you want to try it you should, especially because you are not committed. I can’t hurt my girlfriend, so I might never get the chance to have other experiences. I’d rather have her, than have the experience… but I do have regrets about getting into this relationship so young before I tried everything out. Anyway, that’s my issue. Go for it J. I think Adult Friend Finder is the best idea for no strings sex. Good luck, have fun 😉

  22. 22

    Very interesting Quincy work, but I think you are assuming too much about J from her email. I’ve know women who have lived lesbian exclusively all their lives. They can really be ignorant of men to the point of assuming they will react like women, as per J’s concern that her friends will get emotionally attached from one romp in the hay.

  23. 23

    @ Steve #22 — Good point. To be honest, maybe the letter bugs me just because it seems so damn whiny…and implies “I want it all, but only if it’s fun for me with no guy blaming me if he gets hung up on me.” Of course, it’s possible I’m just projecting.

    @ Bess #21 — I certainly have no answer to your predicament other than that tired old saying: “The grass is always greener. . .” The unknown always seems so tempting, yet in reality can often be an incredible dissappointment. But I admire your loyalty to your woman & that you’ve weighed the price of the experience against the possibly of losing your current relationship. I think all of us go through this struggle at some point, the “what if?” syndrome, regardless of sexual orientation.
    Just a thought, but one thing you might consider is a threesome — you, your current woman, and a guy. Whatever works.

  24. 24

    Thanks Steve – I appreciate the stand up. Lance & Marc – lol. Selena, Jack, Honey, Annette, Shalini, Kat – I appreciated the thoughts…they hit the spot for me. Bess – I really admire that you know what you value. Suzanne – you’re pretty straight up but yeah, you projected. Cheers 🙂

  25. 25

    @J and Steve:

    Condoms do not take care of all of the problems for women.

    The most common STDs are HPVs for which there are no cure, though many people are able to “clear” these  infections themselves.  For those who can’t, many women go on to develop cervical cancer.  I was “lucky” because I got it in time.  

    Female condoms provide more protection, but I find them very difficult to use, so not safe.

    Finally, J… buy some condoms yourself.  If you think you might be with a big or tall guy, for goodness sakes buy some large or extra large trojans.  They are much less likely to break if you are with a bigger guy.

  26. 26

    I vote for picking the best looking guy who gets you going and who you mesh with in conversation.  The rest will take care of itself.  Barring that, you could do, um…. nekkid interviews. 🙂

  27. 27

    I had a similar thing happen to me this past weekend. I’m a straight guy and one of my lesbian friends had sex with me. I guess she felt comfortable with me. I’m a nice guy and try to get along with everyone. Anyways we talked the next day and she asked me not to say anything to our friends. I told her I wouldn’t and not to feel weird around me. If she wants to do it again I’m here for her but if she doesn’t that is fine too. She is a good friend and I told her either way I don’t want to lose her as a friend. Maybe she wanted to experiment so I went with it. I would rather her have sex with me than a stranger and have her catch something. I would be lying if I said I didn’t have any feelings for her but I know better than to try and change her. She is who she is and I love her for that. I have another lesbian friend who always gets jealous when I hang out with other lesbians or straight women. I can’t figure that one out. She is a close friend and I love her too but again I know she’s not interested in me that way. If you have a close guy friend that you feel comfortable with give him a shot. But its up to you if you want to experiment with a guy you know and trust or a stranger who could have an std or if the condom breaks disappear and leave you with a kid or be a dead beat dad. Either way if your allergic to latex tell them ahead of time I speak from experience. 

  28. 28

    Hah, I always identified as a lesbian and I ended up hooking up with a guy who is part of my friend group, although I wouldn’t say we’re close. For me, it was good to try with him because I knew him well enough to trust him to respect my boundaries, but not so well that it’s awkward. Granted, this only happened two days ago, so it’s hard to see how it’ll play out. But for me, it’s because I’ve been questioning bisexuality more than just a for the hell of it kind of thing. I don’t know if I walked away with any real answers to that yet though.

    As for the actual sex, it was alright. Some of it was enjoyable, but it also hurt. I’ve hooked up with some girls that were worse, but some that were way, way better. And, you do have to worry about pregnancy, which when sleeping with another women is never an issue. If you’re just curious about it, I’d say it’s probably not worth it. 

  29. 29
    Mrs Happy


    quality is important here.

    Some men are fantastic lovers, and some are dreadful, and most are average.

    The last thing you want here is inadequate or even average sex.

    If you want the best one-off heterosexual sex you can access, this is what I would suggest:

    ask your straight girlfriends who their best ever in bed was, and why; make a list, and start calling/meeting/propositioning. Hopefully one of those men will be able and willing.

    NB You cannot rely on a man’s self-evaluation in this regard, so don’t ask the men how good they are.

    And be safe – tell someone where you are and who you are with, and use condom/s.

    I wish you luck and enjoyment. One of my ex’s made love like Mozart wrote music, seriously I have never experienced anything like it, and 15 years on I still smile every single time I think of sex with him. I have recommended him to one or two single female friends. That’s the sort of experience you want!

    1. 29.1

      Waw Did U lke it??  for myself  :- I ve been with a lady whome I married but did not like sex so I had my time with others till my daughter found some messages on my phone ..

      Now we are divorced I got another wife had a young boy with her and still sex hungry so I wanna try 2 lesbians maybe I like it & they do too !!

  30. 30

    Well since we have much more gay women now than ever before nothing surprises me anymore.

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