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Old 12-27-2006, 10:08 PM   #1
HaplessHedonist
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First Time with a Twist: Deflowering the Mature Virgin

So, as promised in my new member intro, here is the subject that got me to stop lurking and actually join this place.

I'm 32, and have been through a number of relationships since I was in college. My first girlfriend was significantly older than me, and unsurprisingly I wasn't her first. Since then, it has so chanced that I have never been with a virgin. Occasionally I've wondered idly what it would be like, but the possibility that it might happen had long since ceased to occur to me seriously...until I began a new relationship recently.

I had been getting to know a friend of mine more closely for a while, and it became clear that we were moving to another level. She's my age, and has been single over the couple of years that I've known her. However, she's a very confident person and very outgoing, so I assumed that there were probably other relationships in her past. Sitting up talking late one night, we became a lot more physically intimate than we had been before, and she eventually told me rather shyly that she was a virgin. I've never been so surprised!

We talked about it and agreed that nothing should happen too quickly, but it's now looking as though she is ready. Obviously, I'm extremely honored to be the first to receive something she's waited so long to give, and I want to make it as special for her as I can.

I'm not worried about making her comfortable and relaxed and generally taking care of her, but I am a little nervous about how it will be for a woman in her thirties to be entered for the first time, especially given my own lack of experience with anyone inexperienced! From what I have gathered so far, her hymen does seem intact, and I wonder if it will be different or more difficult in any way than for a younger girl -- and if so, what I can do to help.

Any thoughts much appreciated...
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Old 12-28-2006, 02:31 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, 07:17 AM   #3
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The best of luck!

I think the best thing you can do is to be slow, gentle, talk to her a lot, and explain that the first time will be followed by many more as she is ready.

P.S. And, of course, ensure that she is extremely relaxed and ready beforehand by a great deal of what you've already been doing.

Last edited by agardineruk : 12-28-2006 at 07:21 AM. Reason: postscript
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Old 12-28-2006, 11:47 AM   #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, 11:50 AM   #5
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Thanks for your responses

I'll reply in order. First of all, she's very sensual. She masturbates quite a lot, and she has no problem cumming on her own fingers, or more recently on mine or on my tongue.

I think what happened was that when she was younger, she just didn't find anyone she wanted to be with, and as time passed, she got used to being single, and found it harder to meet people. It seems to be have been more of an accident than design. From what she says, there's no big reason to do with guilt or trauma.

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!

The kinds of stuff I've been thinking about is exactly along the lines of what the second poster said -- getting her really aroused first, going slowly and gently when I do finally enter her, and so on.

I just wondered if anyone had any specific tips about how to take her the first time, to make it as comfortable for her as possible, and whether her age would make any difference to that.

Thanks again!
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Old 12-28-2006, 12:02 PM   #6
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Hi Erika

I was replying to the earlier posts as you were writing yours! Thanks for your welcome.

I have reviewed the threads you're talking about, that deal generally with first time issues. They say mostly what I would have expected from general common sense -- gentleness and preparation and everyone being different and so on. All of which is good to hear, of course.

However, I do wonder if anyone has any experience of a woman's first time coming rather later than most, and thoughts about anything that might make that different -- preferably from her point of view, but also from a man who has been in my position now.

Thanks again.
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Old 12-28-2006, 12:03 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, 12:13 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, 12:23 PM   #9
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Thanks again, Erika.

My understanding is that she masturbates only clitorally and doesn't penetrate herself. I have stroked and licked across her entrance and haven't been able to insert more than the very tip of my finger or tongue. I believe it's possible for some women to insert a tampon past the hymen, so I don't think that's conclusive on its own. I will certainly be investigating more manually as you say, but my impression at the moment is that it's hymen, rather than just her being very tight.

I totally agree about the lube. She doesn't seem to get very wet at all, even when she's clearly highly aroused, swollen and even climaxing hard. If she comes on my tongue, it's mainly my saliva that seems to be making her wet, and from my fingers likewise. I did wonder if that might be partly due to her hymen, if that stopped some of her natural lubricant and kept it inside. I'm not sure how likely this is, in terms of where the glands are that produce hers, in relation to her entrance.

Last edited by HaplessHedonist : 12-28-2006 at 12:28 PM. Reason: clarify who I'm talking to!
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Old 12-28-2006, 12:27 PM   #10
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Quote:
Originally Posted by RhumbRunner13
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.

Rhumb
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*

Last edited by HaplessHedonist : 12-28-2006 at 12:42 PM. Reason: adding text
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Old 12-28-2006, 01:10 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, 01:26 PM   #12
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Quote:
Originally Posted by RhumbRunner13
LA (the cat) is a tribute to one of my best friends for 17 years. Sadly, he is gone now, but never forgotten.
I'm sorry to hear he's gone. I miss having a cat myself very much. I've had a couple of magnificent cats over the years; they really are the most amazing creatures.

As to the hymen thing, what I've felt so far wasn't like what you describe in terms of feeling rough, it just feels closed. We're both away over the holidays, but when we get together in the new year, I'll have chance to talk more with her about it and explore her more fully too. At the moment, I'm thinking that she has just been gently inserting tampons into the opening that the hymen leaves free, maybe stretching it somewhat but not breaking it. I don't think she's really had the kind of trauma that would lead to scarring just from what she has done herself.

Sorry your good advice to the lady you met didn't meet with greater reward, but perhaps it has come back to you in other ways since!
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Old 12-28-2006, 02:10 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, 03:02 PM   #14
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Quote:
Originally Posted by TBKahuna123
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.
I take your point about her responding in a less shocked way, for which I am duly grateful; I'm definitely not expecting her to take screaming fits I just meant that the pain itself might be greater; I don't know if the elasticity of certain flesh might be less now than they were 12-15 years ago. As to the lube, no doubt of that.

Slow and gentle I completely agree with. However, I get the sense that she wants me to "take;" her giving will come in the trust and intimacy of offering herself to me to begin with, and throughout. She feels safer knowing that I'm controlling things, because she knows I will listen to her, but still wants to be able to relax and let me take the responsibility.

PS I may very well pull out and pee on her leg. Or her clit. Or both.

Last edited by HaplessHedonist : 12-28-2006 at 05:07 PM. Reason: obligatory golden shower reference
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Old 12-28-2006, 03:18 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, 05:13 PM   #16
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Quote:
Originally Posted by TBKahuna123
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.
The full text for posterity:

"You get a boner, you slap her titties around, then you stick it inside her and pee."

"You sitck it inside her and pee?"

"Yeah, unless you don't want to get her pregnant, then you pull it out and pee on her leg."

I had forgotten the first bit. I do definitely plan to get a boner and slap her titties around first as well, naturally, as part of the careful preparation we've been discussing. I haven't decided if I want to get her pregnant yet, so I haven't decided whether to pee on her leg or inside. Either could be rather pleasant...
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Old 12-28-2006, 05:40 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, 07:16 PM   #18
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You mean you don't think the idea of being rent asunder by your lover is frightfully romantic?

Seriously, when we next have the chance to be together after the holidays, I will have a conversation with her along those lines, together with a more profound [!]and leisurely exploration, and see where we go from there. If it seems likely afterwards that she might be more than usually well-armored, I will certainly get her to look at some resources and recommend surgical removal, but in the end, if she prefers me to a scalpel, I won't deny her wish, just try to spare her the worst consequences of her folly...
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Old 12-28-2006, 07:52 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, 08:52 PM   #20
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That's the reason I won't force a scalpel on her, if she doesn't want one
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Old 12-29-2006, 01:49 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, 11:11 AM   #22
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Erika was the one suggesting the surgical option, which is fair enough to raise as a possibility. I'll put that idea to her if I have any reason to believe there's something unusual that's likely to cause a big difficulty, but not otherwise.

The default option will be lots of exploring, extended stimulation, extra lubrication, and slow gentle firm pressure until I'm inside.
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Old 02-19-2007, 02:19 PM   #23
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Update

It just occurred to me that I really needed to post an update, for anyone who might happen to look back at this.

In the end, everything went very smoothly. She was much more open than I had realised. I guess 25 years of tampons had done their work. *S*

Anyway, after a long period of stroking and licking, she was more than ready, and I was able to enter her quite easily. It took her a little while to adjust at each stage as I gave her a little more, but was quite soon able to take me fully. She was very tight and I think it was no more uncomfortable for her than it was for me, actually! There was a very slight pink tinge in her juices, but otherwise no blood. And the second time, a little later, was delightful.

Thanks to all who commented earlier!
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Old 02-19-2007, 03:31 PM   #24
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Congratulations! Thanks for the update.
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Old 02-19-2007, 07:22 PM   #25
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So glad things went well, and thanks for the update!
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