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Sometimes You Need Date Night With Yourself

Hi, Shay,
I’ve read your blog for some time now, and I think it’s great! I have a pretty detailed question, so if you have time I’d really appreciate some advice. I’m a virgin, although my ex and I fooled around a lot and got to oral, etc., without actual penetration.  I’ve always masturbated by crossing my legs and squeezing my thigh muscles together, which is a pretty fool-proof method for me but isn’t very attractive to do in front of someone else, so I’ve had trouble showing my ex what I liked. Since we broke up some time ago, I’ve been dating but I haven’t met anyone I like enough to have my first time with, and I’m getting more and more worried about it.

I bought a small vibrator and I did everything right, down to mood lighting, lube, taking my time, porn, fantasies, the whole shebang. Nothing. I can’t come with a vibrator, and penetration, even very slow, gradual, gentle penetration, hurts too much to continue. I’m pretty sure my hymen isn’t intact, since I can’t see it at all, but I just cannot get anything bigger than a finger in there, no matter what I try. I can’t come with manual stimulation of my clit, either. Just the leg-crossing thing, and penetration is awful. I keep worrying that when I do get around to having sex, it will hurt too much and I’ll end up being embarrassed and frustrated. I want to have fun, get laid, enjoy sex like most of the other people my age, but I just don’t want to end up disappointed. I know the first time isn’t going to be magical or awesome, but at this point I just want to get the first time over with so I can stop feeling like such a freak and start having fun, but I’m scared.

What should I do? Is it possible that there is something wrong with the way my vagina is shaped, so that it won’t allow penetration? I feel like everything is right, but it is just way too painful.  Every website or book gives me the same advice: slow down, take your time, use lube, relax, blah blah blah, but none of that helps and there doesn’t seem to be any other advice out there.  I just don’t want to deal with the scary doctor’s office until I officially have to. I’m sorry to send you such a long email, but this whole thing has become really stressful recently and I’d really appreciate any suggestions you might have. Thanks so much!

My first piece of advice is to stop stressing out.

I’m not going to deny that sex is fun – but you shouldn’t feel like a freak just because you haven’t had a chance to try it yet! A lot to do with sex happens in your head, and being stressed out or worried about your first time can contribute a lot to the kind of problems you’re experiencing (but now don’t worry about being worried! ^_~). From what you’ve told me, it sound like you might be experiencing something similar to vaginismus (tight clamping of the vaginal muscles); usually this disappears over time, as you become more comfortable and experienced.

Here is what I suggest: set a date night with yourself every week – at least once a week (you can adjust it to your schedule as needed). On these date nights you’ll have something nice for dinner, take a hot shower, find some porn/erotica that you like, and spend some time exploring your body.

If crossing your legs works for getting you off, do that – but stop every so often to try touching yourself another way: try inserting a finger or two, try using the vibe on your clit – mix things up a little – but don’t let yourself get frustrated if something doesn’t feel good, just stop and go back to what does work for you.

Be very gentle and patient with your body and it should come around eventually.

On another note – the doctor’s office isn’t scary!! You should definitely make an appointment to have your annual physical done (it’s very important), although you’re not sexually active yet, it’s still a good idea to get everything checked out. Pick a nice female doctor and let her know about your concerns; one of the exams does involve opening your vagina and taking swabs, so you should let her know that you’re afraid this will hurt. (I’ve never found it too painful, if that makes you feel more confident.)

Don’t worry, everything will be fine. ^_^

2 comments to Sometimes You Need Date Night With Yourself

  • Tim

    What a great response…i can feel the concern…like an arm around a worried friend…your heart is true.

  • Bob

    maybe she should attempt penetration – a finger or a slim vibrator – after first achieving orgasm by her tried and true method, squeezing her thighs together.

    she could also, an alternative to a shower, try a long hot bath (with candles, bath oils, a glass of wine, etc.) would be VERY relaxing and set the mood for erotic self-play.

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