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Old 12-27-2006, 11:08 PM   #1
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Old 12-28-2006, 03:31 AM   #2
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You haven't posted much information about her sexuality which would definitely play a role. Does she like masturbating, how often does she masturbate and can she bring herself to an orgasm? What is her attitude towards sex, what are the reasons she stayed a virgin for so long? Is she religious, is there a possibility of her having guilt issues (even though she is an extrovert), does she have a traumatic memory associated with sex and intimacy?

In any case, a "mature" attitude towards deflowering involves not expecting too much from it. Both you and your lady should prepare for the possibility that the first time will be a bit awkward and not the ultimate experience. After all, you wouldn't want it all going downhill afterwards, would you? You should simply enjoy the intense intimacy and not worry about orgasms or any other "bonus features" of sex.

Best of luck and please report back
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Old 12-28-2006, 08:17 AM   #3
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Old 12-28-2006, 12:47 PM   #4
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Welcome. There are a bunch of First Time threads in "The Blank Manual" sticky at the top of How To (right by New Member Intros) with a ton of great advice on this that I think you'd likely benefit from.
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Old 12-28-2006, 12:50 PM   #5
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Old 12-28-2006, 01:02 PM   #6
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Old 12-28-2006, 01:03 PM   #7
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Quote:
Originally Posted by HaplessHedonist
What I'm worried about isn't so much pleasing her or her ability to enjoy herself (certainly not in the medium to long term), I'm just concerned that I do whatever I can to minimize any discomfort from her hymen tearing, and to help her adjust to having someone inside her for the first time. I can imagine that for a woman in her 30s especially, the first time you take anything bigger than a tampon might be a bit of a shock!
Well, it shouldn't be a shock because you should be preparing her for it, with lots of manual penetration over time and perhaps even toys. Hopefully she's been masturbating and knows how to penetrate and please herself so she's less new to this and can guide you.

Are you sure her hymen's intact? Unless it's unusually thick (in which case it often has to be surgically broken by a doctor, and her gyno should have said something at regular checkups), it's unlikely a woman in her 30s who's been using tampons for years still has a hymen. A lot of people seem to think the hymen's on the inside of the vagina, when it's actually right at the entrance, in my experience. If there's any possibility you're mistaking it for something else, do a google image search for 'hymen' - there's no shame in not knowing; not trying to learn, however, is a totally different story.

Even if she doesn't have a hymen, there's likely to be discomfort-pain if she's not completely relaxed, aroused and lubed (I'd suggest using artificial lube even if you two thinks she has enough).
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Old 12-28-2006, 01:13 PM   #8
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You say her hymen does "seem to be intact", yet hint that she has used tampons. I would guess that if she has used tampons her hymen is either gone or may have torn partially and may have healed with some opening but scar tissue could create a situation where the full rupture could be very difficult.

Are you aware that the hymen is external to the vagina? Are you able to insert a finger, then two into her vagina? Are you familiar with the G-spot and can you get to it?

I ask because what you might be experiencing is simply a "smallish" opening to the vagina with no hymen involved.

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Old 12-28-2006, 01:23 PM   #9
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Old 12-28-2006, 01:27 PM   #10
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Old 12-28-2006, 02:10 PM   #11
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Quote:
Originally Posted by HaplessHedonist
I'm quite familiar with the G-spot However, with her, I've not been able to insert more than the tip of my tongue or a finger. I think she has been inserting a tampon around her hymen, or at most, partly broken it.

The issue of scar tissue is one I hadn't thought of; that's something to take seriously into account. Thank you for that.

By the way, that's a very beautiful cat! Do you belong to it? *s*
LA (the cat) is a tribute to one of my best friends for 17 years. Sadly, he is gone now, but never forgotten.

The reason I asked about the hymen is because I ran into a very similar situation many years ago. I met a beautiful lady one day on a trip and we hit it off to the point where we were getting pretty passionate later that night. When we started heavier petting, her hymen felt very rough, bumpy and pretty much "impenetrable". We talked about it and it was a situation where she had been penetrated pretty roughly once and it healed as, what seemed to me, heavy scar tissue. She was kind of embarrassed by the situation but when she realized my concern was more with her that getting myself layed, she agreed that a visit to her gyno was in order to allow a full enjoyable life.

We never saw each other again, damnit!!

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Old 12-28-2006, 02:26 PM   #12
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Old 12-28-2006, 03:10 PM   #13
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My gut tells me that a more mature woman should be able to handle the sensations and the hwole experience with less shock than a younger woman, not more. If nothing else she'll be able to better appreciate your efforts at being gentle with her than a younger woman might. All in all though, I think it will probably be about the same physical sensations.

One thing that will definitely help is an artificial lubricant. This will definitely help things go smoother. I really wouldn't do anything different than I would with a young woman, if I were you. Just focus on slow and gentle, let her control the pace. Maybe let her be on top. Let her give you her virginity, rather than taking it.
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Old 12-28-2006, 04:02 PM   #14
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Old 12-28-2006, 04:18 PM   #15
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Quote:
Originally Posted by HaplessHedonist
PS I may very well out and pee on her leg. Or her clit. Or both.
Huh?

Oh yeah, my sig line! I forgot I still had that up! That was in response to Eilan's sig line which is the first part of that quote. I shoudl change that since she's changed hers. The joke is now lost.
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Old 12-28-2006, 06:13 PM   #16
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Old 12-28-2006, 06:40 PM   #17
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If you can only get the tip of your finger in, I can't imagine she'd be able to get a tampon in and still have an intact hymen. Possible, but not likely.

What I would suggest is talking about it openly with her. Tell her you're afraid of hurting her with penetration, and ask if she'd be willing to get her doc's opinion on it. Having it broken under local anesthesia so you two will be able to play around and have sex will be far more pleasant than a lot of pain, blood, being unable to have sex until she heals, etc.

This is our favorite lube and I've yet to find a better deal on any good lube (it's great for massages, handjobs, moisturization and just about everything else you can think of).
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Old 12-28-2006, 08:16 PM   #18
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Old 12-28-2006, 08:52 PM   #19
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The simple fact is it may hurt, it may not, it may sting a bit, it may be excrutiating, who knows? One thing I can promise you though is that no matter what the pain level is, if you do your best to make it a romantic, gentle, caring experience for her, she will remember it fondly.
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Old 12-28-2006, 09:52 PM   #20
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Old 12-29-2006, 02:49 AM   #21
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Personally I think you are making too much of this. Yeah it's possible that she might have an abnormally thick hymen that needs to be surgically broken, but the chances of that are small. I understand you are trying to be senstitive about it, but I truly think you are overthinking this.

Be as gentle as possible, do your best to make the overall experience special and don't worry too much about that initial moment of penetration. There is only so much you can do to make her more comfortable physically, so that and go the extra mile to make her comfortable mentally. I'll promise you'll get more mileage out of that than anything else.
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Old 12-29-2006, 12:11 PM   #22
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Old 02-19-2007, 03:19 PM   #23
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Old 02-19-2007, 04:31 PM   #24
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Congratulations! Thanks for the update.
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Old 02-19-2007, 08:22 PM   #25
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So glad things went well, and thanks for the update!
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