• Advice needed: fitting a round peg into a square hole

    Mystral [sign in to see picture]
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    Hi All,

    This may be in the "nice problems to have" section, should one exist...

    Recently hooked up with a very special lady who I'm currently in the process of falling for, mutually one would hope.

    We've dated since the beginning of may and have now found our way into the bedroom where we've discovered that I'm quite large and she's quite small.

    We've had plenty of other fun, thanks to some toys from here, but penetration has proved to be too painful (though she was able to fully accomodate me) even after copious foreplay.

    She's only had a couple of partners before and when playing alone has always got her self off by rubbing only; so she's quite unaccustomed to the sensations involved.

    Being that she did sit fully on me I think the issue is more girth than length. I'm 8 long and 6 around, though tapering towards the base (top heavy) which she noticed as more comfortable/less painful when fully in.

    Given my size, I'm used to having a partner pause for thought but never have I had this kind of trouble nor have I taken a women's virginity, which is how this feels despite the facts.

    As I say, we're having plenty of fun otherwise and hope it's just a question of time, but hoping you might be able to provide some tips on positions (she seemed to prefer lying on her side so she was 90 degrees to missionary), stretches, toys,etc that could help us along.

    Thanks for reading and for any forthcoming advice =)

    Stuburns [sign in to see picture]
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    Hmmmm. Seems at the moment most women on here are trying to tighten things up. Other than the usual loads of foreplay and lube is she relaxed or does she tense up in fear of the impending pain? Maybe introduce some smaller toys eventually working up to something more your size. Even a good soak in a warm bath could help. The more time you can spend gently stretching her with your fingers could also possibly help. Keep trying for sure. Good luck.

    Mystral [sign in to see picture]
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    lube and foreplay have been robustly tried ;)

    Should also note that she came almost immediately when we did manage to get it in, so I'd say she was fairly relaxed, but future attempts may have had some anxiety as she had some pain after the initial attempt.

    I later fingered her which she seemed to enjoy though afterwards was a little surprised I'd only been using my index finger.

    A nice bath sounds like a good idea...

    LilBikerGothChic [sign in to see picture]
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    Hi Mystral,

    I have a not too dissimilar "problem" to your lady friend, being quite on the petite side myself. As Stuburns said, lube and foreplay are definitely your friends - you might want to try a thicker lube designed for anal, I've found in the past that the added squidge factor helps. Sounds like a no-brained but its important that she's really relaxed generally too, not just down there. If she's tense or worried about being able to fit you in or it hurting that will make it worse, even if she's not consciously aware of it.

    Another trick I've found which helps is to take a deep breath right before you start with penetration then slowly let it out as you, equally slowly and very gently, slide your way in. I think it helps to relax everything.

    You might also find you're poking her cervix if you are very long (she'll feel a dull pain a bit like a sharp period cramp). It's surprisingly off putting! If that's the case avoid positions where you go in very deep and let her control how far in she takes you - doggy and her on top are good ones. Missionary is not as its difficult for her to control being on her back.

    Good luck!

    BDSM [sign in to see picture]
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    I suspect this is just going to take a bit of time. It sounds like you are having fun, so carry on playing and gently stretching her. Gradually she will become more accustomed to you.

    Mystral [sign in to see picture]
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    Thanks LBGC,

    Having fooled around the week before we'd known what we were in for this weekend so had come here for some necessities; after browsing and sending a few links to sexy ideas back and forth I had picked this out for a laugh:


    Perhaps I was too dismissive, didn't realise it would have a different composition. will float it again as an idea.

    As for relaxed, we try to keep things light hearted and enjoy plenty of laughs as well as massage and gentle to firm manipulation... when we did finally manage full penertration, she was on top. she did mention discovering her g-spot with me being so deep, so not sure if she's feeling any discomfort from her cervex as well.

    I know I've hit others in the past but never heard of it being an issue, will ask for clarity.

    Breathing sounds like a good idea too, will incorparate that into the massaging.

    Little surprised to hear doggy as a good idea, would've thought the angle would be too much so have shied away from it, but understand the point about allowing her the freedom of movement to control the motion.

    To be fully frank, I've had some anxiety over this as well and have struggled to ejaculate even when we've fallen back to simpler play. It's got easier as the hours have passed so hoping the same is happening for her. Either way we're both happy in the end.

    Thanks for sharing =)

    Mystral [sign in to see picture]
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    We're thinking the same BDSM.

    TBH I'm here to discharge some of my impatience, we're being very good and taking things slowly but I was hoping their maybe some quick fix... terrible of me I'm sure.

    We've looked at something like this:


    But given I think it's more of a girth than length issue not sure if it would help.

    I guess some form of dildo would be of use, but struggling with a pride issue of wanting to be the one she grows to enjoy...

    Oh, and I call SNAP on our join date ;)

    BDSM [sign in to see picture]
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    hmmm, Valentine's Day 2009, i wonder what brought us both here then!

    I'd Get a couple of vibrators or dildos. That will help her gets used to the feeling more.

    Fluffbags [sign in to see picture]
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    I have only skim read the replies here so excuse me if I cover anything already mentioned but my first tip would be to not underestimate the power of a decent lubricant! I cannot take my larger girth toys without using a decent amount of good lube.

    I doubt there will be a quick fix I am afraid. If you are big and she is small, well....imagine her trying to penetrate your bottom with a nice thick dildo, I am sure you would appreciate patience! :D

    It seems as though you are already doing most of the things I would of suggested, like plenty of foreplay, ensuring she is relaxed (Has she has any problems before? Any medical issues?)

    The only other things I would suggest is her practising alone with larger toys. I mean, vaginas are elastic and can stretch but afterwards, things ping back to her normal size, you know? So it may be a case that your new lady will need extended warm ups before each session, one finger, then two....you get the drift, until her muscle and skin elasticity has warmed up, stretched and prepped ready for you to enter more or less pain free. By the time you come round to your next session its starting the process again. Is she quite new to sex? I know I couldnt have taken some of the sizes I take nowadays back when I was new, although even now I have a comfort limit, anything about a 5 inch girth and I can't just bung it in and thrust like a demon. I need to warm up to it. Every single time. Because stretching is temporary. Relaxing enough to take a larger size, is something that can change I think. I am no doctor but I often suspect if I am pushing my limits, my muscles involuntarily tighten or clench. Its learning to stop that happening my going slow, so as to not force that reaction and relaxing more. Problem is, for me anyway, if I have tried to push past it when it already hurts a little, it just ends up hurting more and putting me out of action for a while from aching or even chafing or minor splitting...none of those are fun lol

    So my tips I guess would be: Lube...plenty of lube seriously lube is a massive help. Warm her up as you have been doing. I think a bath is a good idea as it will relax her and get blood flowing and maybe add a little elasticity to the skin but don't expect miracles from a bath. Playing alone and practising with larger toys will help, if nothing else it will give her confidence about what she can manage, thereby reducing the risk of nervousness causing tension down there. let her keep going on top for as long as she needs. This will give you both confidence, she will relax more, knowing she is controlling the depth and angle and therefore less likely to hurt herself and it will give you an idea of just how fast and how deep she can manage so that you can mimic that when you try different positions. Speaking of positions, try lots. As many as you can think of. What works for one woman doesn't work for another and I know some positions do cause penises to feel deeper, but they may also open her hips out more, or the angle (Pushing into her back passage rather than her g-spot and bladder) might be enough to cause less intensity during penetration. You never know. Try them all and rule out ones that are a no-go for now and work on ones that work. Have patience. There can be many thrills to your sexy times that don't involve hard/fast/you in control penetration. :D I know it feels amazing etc but women sense things. If she senses your impatience in this, it may make it worse or she may feel like she is letting you down. :(

    Hopefully things will get easier as she gets used to your size.

    Mystral [sign in to see picture]
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    Cheers Fluffbags.

    Progress Report:

    Had a straight date go short last night so, prompted by limited time, we had a quick stretch.

    All went very well =)

    We think we were just over eager and rushed it the first time and she needed a few days to recover so, whilst we'd tried finger play over the weekend, last night was extremely successful. For one point, being able to have a good feel of her relaxed around 3 fingers (which we hadn't got to before), I had a greater sensitivity then when sheathed. So now I know by how much I need to compensate. She was a lot more comfydent with taking me fully too and we're seeing each other on friday...

    Thanks for all suggestions =)

    KinkyFuckery [sign in to see picture]
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    Glad it went well

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