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A sex question

gotaquestiongotaquestion Registered User
edited December 2008 in Help / Advice Forum
Ya, this is an alt. RL ppl know my alias and I don't want them to find this question through a google search as they can put 2 and 2 together.

Here's my problem. I'm 27 and I've never kissed a girl, let alone had sex.
I've recently told friends about this. One of them...mabye two, have given me the idea that I might get some practice with them if I ask.

Here's my dilemma. One of them is engaged. However she has also been the most vocal about lending me a hand. She has a very open relationship with her fiance and is openly bi-sexual. She has done it with girls and her fiance knows about it and is cool with it(who wouldn't?). She's basically told me that if her fiance found out she gave me some practice he would be cool with it.

The other girl, not engaged but does have a boyfriend. Who may not be so cool about it if we're not discreet enough.

Plus, apparantly, the girls have discussed having a 3-some with me.

So, am I being too uptight about this? Both of them are cool with it. But I'm still looking at the "both of them are in relationships" angle and it makes me a little uncomfortable. I suppose if I'm reading this situation correctly and something actually got started then I may not be uncomfortable anymore.

But what do you guys think? Should I be hitting it without a second thought? Should I continue to put it off? Would it be as bad if it was non-intercourse play?

gotaquestion on
«134

Posts

  • SarcastroSarcastro Registered User regular
    edited November 2008
    I believe the 'teach me while you learn from each other' stance is gold, and you should run with that. Hit the ground running. Mach 5.

    Apparently I am to add a disclaimer about how you should find your own girlfriend and do things with her instead, have a journey together etc, but Ima punch that guy- you go have fun.

    Sarcastro on
    Edcrab wrote: »
    "See," said Lucifer, "God's an asshole."
  • WillethWilleth Registered User regular
    edited November 2008
    I would find out - subtly - if the partners are cool with it for certain before doing anything else. "He would be cool with it if he found out" implies that there's something to keep quiet about, which in turn implies that no, actually, he wouldn't be cool with it. As an aside, if I was in a relationship with someone I would also be not cool about them sleeping with anyone of either gender.

    If there's any doubt don't go with it. This is the kind of thing you don't fuck around with no matter how much you want to.

    Willeth on
    @vgreminders - Don't miss out on timed events in gaming!
    @gamefacts - Totally and utterly true gaming facts on the regular!
  • ShogunShogun Hair long; money long; me and broke wizards we don't get along Registered User regular
    edited November 2008
    My friend, all systems are go.

    edit: goddamn you sarcastro

    Shogun on
  • LailLail Surrey, B.C.Registered User regular
    edited November 2008
    Go for it.

    Lail on
  • admanbadmanb unionize your workplace Seattle, WARegistered User regular
    edited November 2008
    ... you have unusual friends.

    I would get more confirmation from the fiancee first. It's up to you how you want to handle the girl with the boyfriend -- there's not a small chance that he'll eventually find out, so if you're afraid of that coming back to you play it cautiously.

    Otherwise... Christ man, are you sure you didn't post this after a dream?

    admanb on
  • Kate of LokysKate of Lokys Registered User
    edited November 2008
    Man, if you've never even kissed a girl before, the last goddamned thing you need is a three-way orgy with two women who are already in relationships. That's kind of like saying "I've never driven a stick shift before, so I was thinking I should talk my way into the next F1 race at Monte Carlo."

    There's nothing wrong with being inexperienced. I had never kissed a guy until I was 25; now, a year later, I'm in a loving, healthy, highly sexual relationship. And yes, I had to learn how to do a few things, but I had fun doing it because I was learning with someone I loved who was patient and indulgent and really not all that experienced himself.

    Why do you want to have sex? Is it a rite of passage for you? Do you just want the physical stimulation? Are you terrified that when it comes time to do it with someone you're actually in a relationship with, you'll somehow do it wrong and end up curled in the fetal position with your dick shrivelled nervously up into your body while your partner points and laughs? If it's the first of those, wouldn't you rather share such an important moment with somebody you felt deeply about? If it's the second, well, welcome to the world of not being in a relationship - find one, or deal with it. If it's the third, relax! When you're having sex with somebody who cares about you, there's no such thing as doing it wrong. Even mistakes can be fun, or at least funny.

    Kate of Lokys on
    I'm here to tell you about voting. Imagine you're locked in a huge underground nightclub filled with sinners, whores, freaks and unnameable things that rape pit bulls for fun. And you ain't allowed out until you all vote on what you're going to do tonight [. . .] So you vote for television, and everyone else, as far as your eye can see, votes to fuck you with switchblades. That's voting. You're welcome.
  • SheepSheep Registered User, __BANNED USERS regular
    edited November 2008
    I'm reading the OP here and I keep looking for the part you need help with.

    Sheep on
    QlBGc.jpg
  • acidlacedpenguinacidlacedpenguin Registered User regular
    edited November 2008
    All's fair in love and war.
    Yes, I'm that guy.

    Just don't be a creep about it alright?

    acidlacedpenguin on
    GT: Acidboogie PSNid: AcidLacedPenguiN
  • DemerdarDemerdar Registered User regular
    edited November 2008
    I'd say go for it. Despite what others may tell you, being 27 and never having really any physical contact with a woman is abnormal. This will be a good experience for you.

    Demerdar on
    y6GGs3o.gif
  • noir_bloodnoir_blood Registered User regular
    edited November 2008
    I don't know man...

    I mean, if two girls are willing to have sex with you, then you aren't a total uglo or missing any limbs, so you figure you could possibly snag a girl without help from friends. Friends that are already in relationships that might lead to big time drama.

    noir_blood on
  • RUNN1NGMANRUNN1NGMAN Registered User regular
    edited November 2008
    noir_blood wrote: »
    I don't know man...

    I mean, if two girls are willing to have sex with you, then you aren't a total uglo or missing any limbs, so you figure you could possibly snag a girl without help from friends. Friends that are already in relationships that might lead to big time drama.

    Yeah...here's a not-so out there scenario. You hook up with one or both girls. She realizes that she liked the sex with you more than with her significant other. Crazy relationship drama ensues for all involved.

    RUNN1NGMAN on
  • DemerdarDemerdar Registered User regular
    edited November 2008
    RUNN1NGMAN wrote: »
    noir_blood wrote: »
    I don't know man...

    I mean, if two girls are willing to have sex with you, then you aren't a total uglo or missing any limbs, so you figure you could possibly snag a girl without help from friends. Friends that are already in relationships that might lead to big time drama.

    Yeah...here's a not-so out there scenario. You hook up with one or both girls. She realizes that she liked the sex with you more than with her significant other. Crazy relationship drama ensues for all involved.

    Considering this will be his first time, I find this very hard to believe.

    Demerdar on
    y6GGs3o.gif
  • Mmmm... Cocks...Mmmm... Cocks... Registered User regular
    edited November 2008
    I never had any female contact really till late in high school. It was real awkward for me at first.
    Just because through high school I guess pressure started building in my conscience.

    Getting that first go or so out of the way can really help your self esteem and confidence.
    Though, with a friend it could be strange unless they were 100% understanding and down to earth.

    I'm half way in the boat of saying go for it, but also what you could do is try some internet dating.
    You could post ads and stuff and even post your information you posted here. Perhaps you find a women in the same situation as yourself and they end up being your soul mate.

    Hm, best bet is maybe try that and if nothing comes of it at a certain point talk to those girls.

    Mmmm... Cocks... on
  • wasted pixelswasted pixels Registered User regular
    edited November 2008
    Here's the pool:
    _________________________
    \_                       | 3  ft
      \_                     | 6  ft
        \_                   | 9  ft
          \_                 | 12 ft
            \_______________| 15 ft
    

    Here's you:
    o
    X
    

    Here's you in completely over your head:
    _________________________
    \_                       | 3  ft
      \_                     | 6  ft
        \_                   | 9  ft
          \_     OH NO!!  o  | 12 ft
            \____________X__| 15 ft
    

    That's exactly where you're going to be if you try to learn to have sex with two nearly-30-year-old women who are already in serious relationships, let alone simultaneously. Kate is right on all of her points, you're just asking for all kinds of trouble here.

    wasted pixels on
    BTW, I got a message from Obs that equated installing OS X on a PC with car theft, murder and rape. Is he normally like that?
  • JohnnyCacheJohnnyCache Starting Defense Registered User regular
    edited November 2008
    I don't know how this can be but I agree completely with both kate and sarcastro.

    JohnnyCache on
  • ChanceChance Registered User regular
    edited November 2008
    I kinda' have to agree with Kate. The more sex you have with more partners the less important it becomes. It may sound douchey and old-fashioned, but if you end up saving yourself for the person you want to spend the rest of your life with, you've done something pretty incredible (and incredibly positive).

    I understand you'd be less embarrased to go into a sexual situation with your first major relationship with experience - but if you do this thing you will go into it with the expectations your spectacular 3-way has ingrained in you. You will go in comparing her to This Friend or That Friend. You will have baggage, and you were never even in a relationship.

    Again - listen to Kate. Kate's right.

    Edit: This is almost harsh, so I'll spoiler it.
    You will be much happier knowing your first partner is playing with your bits because she's so damn attracted to you and only you, than if your first partner is sleeping with you because she's feels she needs to help out her virgin friend.

    Chance on
    OuFrYk0.jpg
    'Chance, you are the best kind of whore.' -Henroid
  • RUNN1NGMANRUNN1NGMAN Registered User regular
    edited November 2008
    Demerdar wrote: »
    RUNN1NGMAN wrote: »
    noir_blood wrote: »
    I don't know man...

    I mean, if two girls are willing to have sex with you, then you aren't a total uglo or missing any limbs, so you figure you could possibly snag a girl without help from friends. Friends that are already in relationships that might lead to big time drama.

    Yeah...here's a not-so out there scenario. You hook up with one or both girls. She realizes that she liked the sex with you more than with her significant other. Crazy relationship drama ensues for all involved.

    Considering this will be his first time, I find this very hard to believe.

    The enthusiasm of the inexperienced is not a thing to be discounted.

    RUNN1NGMAN on
  • proXimityproXimity Registered User regular
    edited November 2008
    If you are already feeling awkward because the others are in relationships, and that is the biggest thing stopping you, then that's not going to resolve by just jumping in and doing it. It will just come back to haunt you if you don't get explicit okay from your friends' male partners.

    proXimity on
    camo_sig2.png
  • noir_bloodnoir_blood Registered User regular
    edited November 2008
    If you can get assurance somehow that their partners won't mind(which I imagine would be hard), then go for it.

    Or if they're hot.

    noir_blood on
  • ProPatriaMoriProPatriaMori Registered User regular
    edited November 2008
    I'm going to have to say go for it. If the partners aren't cool with it, the girls have to answer for that.

    By way of allegory: when I was like, 4, we were having a pool put in at our house, and the friendly guy using the little Bobcat tractor would let me drive in it with him. I had never driven anything before ever and loved construction equipment (I was 4) but to do this I would have to put on shoes and I didn't want to put on shoes (I was 4!) so it did not happen.

    I regret that to this day.

    ProPatriaMori on
  • noir_bloodnoir_blood Registered User regular
    edited November 2008
    I'm going to have to say go for it. If the partners aren't cool with it, the girls have to answer for that.

    By way of allegory: when I was like, 4, we were having a pool put in at our house, and the friendly guy using the little Bobcat tractor would let me drive in it with him. I had never driven anything before ever and loved construction equipment (I was 4) but to do this I would have to put on shoes and I didn't want to put on shoes (I was 4!) so it did not happen.

    I regret that to this day.


    So what you're saying is that he needs to make sure he's wearing shoes?

    noir_blood on
  • ProPatriaMoriProPatriaMori Registered User regular
    edited November 2008
    noir_blood wrote: »
    I'm going to have to say go for it. If the partners aren't cool with it, the girls have to answer for that.

    By way of allegory: when I was like, 4, we were having a pool put in at our house, and the friendly guy using the little Bobcat tractor would let me drive in it with him. I had never driven anything before ever and loved construction equipment (I was 4) but to do this I would have to put on shoes and I didn't want to put on shoes (I was 4!) so it did not happen.

    I regret that to this day.


    So what you're saying is that he needs to make sure he's wearing shoes?

    You wouldn't think it makes a difference but it does.

    ProPatriaMori on
  • JohnnyCacheJohnnyCache Starting Defense Registered User regular
    edited November 2008
    hey PPM

    just so you know

    Driving a bulldozer is so fun sometimes I tell a 25 buck an hour bulldozer driver to just take a break on the company because I want to drive the fucker.

    I did have a point to add to the main thread as well: Everyone here is assuming the three way will be AWESOME if he takes it. I've had an awful lot of threeways for a guy that looks like me, and they go about 1 awesome one to 2 where you're just basically having sex with one person while touching some extra boobs or something to 1.5 that go totally screwy - and that's DURING. Afterword they are like 1 good aftermath to 3 weird aftermaths.

    You

    JohnnyCache on
  • ProPatriaMoriProPatriaMori Registered User regular
    edited November 2008
    ITT everyone causes me pain.

    Seriously, though, it's one of things where if you don't you'll always wonder what it would've been like. I fly planes, I've driven forklifts (all kinds of fun), skydived, driven over 100 miles per hour on highways in several states, but that little Bobcat will always haunt me.

    Edit: Also PPM is the approved abbreviation. Go Johnny.

    ProPatriaMori on
  • ilmmadilmmad Registered User
    edited November 2008
    Yes but PPM have you flown an airplane which you then skydived (skydove?) out of and landed in a forklift in which you proceeded to haul ass at 100mph down a highway?

    On topic though, I think the OP should wait. Both these women are attached and as awesome as a threesome sounds you probably aren't ready yet. Mentally and physically.

    ilmmad on
    Ilmmad.gif
  • oldsakoldsak Registered User regular
    edited November 2008
    Man, if you've never even kissed a girl before, the last goddamned thing you need is a three-way orgy with two women who are already in relationships. That's kind of like saying "I've never driven a stick shift before, so I was thinking I should talk my way into the next F1 race at Monte Carlo."

    That analogy almost works, except driving in a F1 race could get you killed or injured while the worst that could happen learning and experimenting with two friends is things are weird for you and you feel a little embarrassed.

    As for their significant others, if they're not really cool with it you're really a friend then you probably don't want to do anything that will mess up your friends' lives. On the other hand, they're big girls and can make their own decisions. If the significant others are indeed ok with it, well all the better then.

    oldsak on
  • ED!ED! Registered User regular
    edited November 2008
    As to whether you should engage in sex with one or both of them: yes. As the poster above stated, the WORST that can happen is you pop quickly and are a bit embarrassed. However if this isn't a one-off thing it COULD be a good boost for your self confidence without having to actually go through the motions of finding a female to date, and then have sex with.

    The significant other issue - unless they are toughs who WILL come after you, then its their problem not yours.

    ED! on
    "Get the hell out of me" - [ex]girlfriend
  • Ziac45Ziac45 Registered User regular
    edited November 2008
    Do not do this, It sounds amazing I can't honestly say if I was in your shoes I wouldn't do it. But they are both attached and it really can only lead to problems, I doubt both of their significant others would be okay with you having sex with them. The fiance who doesn't have a problem with her having sex with women could very well have a problem with her having sex with a man.

    Though you should start looking for someone to get in a real relationship with. It is slightly abnormal to be 27 and have no experience but like others have said it will be more worthwhile when its someone you care about and not just friends pitying you.

    Ziac45 on
  • gotaquestiongotaquestion Registered User
    edited November 2008
    Hmmm, I'm kinda leaning towards not doing it. As awesome as it sounds to lose virginity via threesome it might simply be too much at once. And their current relationships do make me a a little nervous.

    gotaquestion on
  • JohnnyCacheJohnnyCache Starting Defense Registered User regular
    edited November 2008
    You could you know

    Focus more on one of them at first . . . It's unlikely they will then decide they hate you and you can make a more informed decision on kinkier stuff later

    JohnnyCache on
  • ProPatriaMoriProPatriaMori Registered User regular
    edited November 2008
    Hmmm, I'm kinda leaning towards not doing it. As awesome as it sounds to lose virginity via threesome it might simply be too much at once. And their current relationships do make me a a little nervous.

    The girls are your age, right? They can make the call on what their relationship means and how they can act in it.

    I can't say I've personally had a threesome, but you're already asking for something more talky than usual (they're trying to "teach you," right? So you're going to want feedback) and it seems like having a third person there can only help that. I can't help but imagine one of them giving you a tip and the other going "wait, really?" and the best type of science experiment ever ensuing.

    But it's not like we'll hate you if you don't.
    I will totally hate you if you don't.

    ProPatriaMori on
  • AltyMcAltAltyMcAlt Registered User
    edited November 2008
    If you do decline it, that's your choice and we'd all respect you for it- for considering the consequences rather than just screaming "yes". You shouldn't pursue it unless you're completely comfortable. If you're not too sure about the reactions of their significant others, don't feel pressured into participating just because they offered to organize it.

    But for my two cents, I only had penetrative sex when I was 23. Discounting one incredibly intense handjob when I was 14 I had no contact with any women, not even kissing. Assisted jerking-off, nine years, sex.

    And I mention this because, uh, there was another participant, the woman's 31-year-old flatmate. It was incredible, in a flushed, slightly embarassed, holy fuck is this actually happening sort of way. For the most part she just watched, until uh, the climax. And some activities afterwards.

    I'm only saying this because I very nearly turned down the opportunity and it ended up being one of the few experiences in my life that I can say I'm entirely happy with. If not my all-time favorite, hah.

    What I'm trying to say between the lines is that your mileage may vary, especially given the circumstances. But hell, you waited even longer than I did, you'd deserve that kind of opener if you ask me.

    AltyMcAlt on
  • TrowizillaTrowizilla Registered User regular
    edited November 2008
    Speaking from the point of view of someone who is in an open relationship:

    Talk to the first girl and ask if she's comfortable with you talking to her fiance. If she isn't, I'd steer clear, because that sounds suspiciously if she's hiding something. If she does, just ask the dude if he's cool with it. Don't get explicit, just make sure he knows what's going on and doesn't object. After that, if everything works out, go for it.

    DON'T do anything with the other girl. If her boyfriend wouldn't be cool about it if he found out? That's called "cheating" and it's not something you should be involved with.

    Also, the whole "the more people you have sex with, the less special it is when you have sex with someone you care about" this is, in my experience, a load of horsecrap. Other people may feel differently, but figure out how you feel before you get into a whole "I want to save my virginity for my truuuuuuue looooooove" thing.

    Trowizilla on
  • WiseguyWiseguy __BANNED USERS
    edited November 2008
    Man 27 years old and you got maybe 53 years left of your life - little bit less or more. This is an opportunity to experience something completely unconventional (for most people) and truly exciting. I say if the possibility of this happening is there, just go for it. Possible ensuing drama may cause a headache, but jesus, man, this will put a goddamn sweet smile on your face when you're all old and reminiscing.

    Plus you will get sexual advice from two women simultaneously. It's a good start.

    Wiseguy on
    [SIGPIC][/SIGPIC]
  • RubberACRubberAC Sidney BC!Registered User regular
    edited November 2008
    Ask for a beginner course with one girl first.
    Then say you are ready for both of them.
    its foolproof

    RubberAC on
    raneasig.png
  • wasted pixelswasted pixels Registered User regular
    edited November 2008
    Trowizilla wrote: »
    Also, the whole "the more people you have sex with, the less special it is when you have sex with someone you care about" this is, in my experience, a load of horsecrap. Other people may feel differently, but figure out how you feel before you get into a whole "I want to save my virginity for my truuuuuuue looooooove" thing.

    I fooled around a bit before settling in with the girl I'm planning to marry, but I don't think it's cool to patronize people who earnestly want to wait for the right person.

    wasted pixels on
    BTW, I got a message from Obs that equated installing OS X on a PC with car theft, murder and rape. Is he normally like that?
  • Blake TBlake T Registered User regular
    edited December 2008
    As someone pointed it, if someone isn't willing to tell their partner they are about to get laid then they are cheating.

    You need to ask yourself what sex means to you.

    If you are cool with meaningless sex. And lets be fair here, this girl that's engaged (cause you are going to stay away from the other one) wants meaningless sex. This can be fine.

    The only time it can be fine is when both people enter the bedroom with this expectation.

    If you go into the bedroom thinking, man what if I am naturally awesome in bed and she is going to fall in love with me. Then don't fucking do it. The only real way you can do this correctly if you go into it with the mindset that she is going to show you the ropes and you are going to have some fun.

    Blake T on
  • TrowizillaTrowizilla Registered User regular
    edited December 2008
    Trowizilla wrote: »
    Also, the whole "the more people you have sex with, the less special it is when you have sex with someone you care about" this is, in my experience, a load of horsecrap. Other people may feel differently, but figure out how you feel before you get into a whole "I want to save my virginity for my truuuuuuue looooooove" thing.

    I fooled around a bit before settling in with the girl I'm planning to marry, but I don't think it's cool to patronize people who earnestly want to wait for the right person.

    If you earnestly want to wait, cool. Seeing it as some sort of romantic ideal for EVERYONE is pretty ridiculous, though.

    Trowizilla on
  • QinguQingu Registered User regular
    edited December 2008
    I think this is a recipe for disaster.

    First of all, if I'm reading your post correctly, it is not at all clear that either of the girls in question is in a truly open relationship. If you go through with it, you may very well ruin both your relationship with these people and their relationships with each other. And even if the fiance is in an open relationship, I am doubtful that her teaching you the ropes won't negatively affect her marriage or your friendship with her and her husband.

    Secondly, I completely agree with Kate on the nature of your problem. Judging from your presence here, you are probably a nerd. You think you're the only 27 nerd who's never kissed a girl? There are a lot of people in your shoes, and I would wager your desperation comes largely from some silly socially normative notion that you're supposed to bang chicks in high school. Our tribe doesn't swing that way, and that's cool.

    I think you should continue to be patient, and instead of looking for someone to teach you about sex, try to find another inexperienced nerd girl so you can learn about it together. Besides, I can't even imagine how awkward it would be to get deflowered by a good friend, let alone a good friend in another relationship.

    Qingu on
  • ShamusShamus Registered User regular
    edited December 2008
    Do it.

    They offered. If their relationships suffers or fail, the blame lies with them.

    What I would do, given this opportunity, is "practice" first with the girl in the open relationship. As you said, she's more vocal. Get that first time out of the way. And then organize that threesome. You'd become a legend. :lol:

    Shamus on
This discussion has been closed.