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I don't agree with your recommendation to keep virginity to yourself. Here's why: In college, I had a casual acquaintance with a pretty young woman who eventually asked me out, which turned me on. After dinner we proceeded to have sex at my place. During the act, I recall thinking "she seems awfully tense," but put it out of my mind. I was young and a player and wasn't particularly interested in going out with her more - so I didn't call. A week later, I got a note from her in which she admitted she was a virgin and I was her first. She wanted to do it again but didn't think I wanted to, so she was leaving it up to me to contact her. I never did, mostly because I was annoyed that she hadn't told me she was a virgin beforehand. I honestly feel that if she had told me, I would have done my best to be careful and much more sensitive to her needs. I would have taken more time; lit candles; played soft music and follow her lead. In short - if I'd known beforehand, I wouldn't have said "no," I simply would have tried to make it a very special time for her. That's what a very nice young woman did for me when I lost my virginity; it's the least I could do in return.
i guess i should forgive your answer because you're not a woman, don't have the same parts that we have, and don't fully understand how our bodies work.
now, i understand this writer's problem; i lost my virginity at 21 and was lucky enough to find someone who cared about me and to whom it didn't matter... but enough about that.
here's the skinny: hymens are generally broken/gone by the time a woman is in her 20s. we use tampons, masturbate, etc. but they can be there, and they can bleed. even if a woman has played with her own sexual toys.
here's another thing about a woman's body: if she's in any way nervous about this, her vaginal muscles can tighten up like a vise grip, make sex horribly painful. think searing pain.
i'm not saying these things will happen, but that they could. would it be fair to any man to put him in the position of having a hysterical, bleeding and sore woman on his hands? talk about scaring a guy away... geez.
i don't have the answer, but yours isn't it.
I'm in the "Tell the truth" camp but not the "Be patient and wait" camp. I vote for "Tell the truth, but be proactive."
What I recommend for this young woman is to place a personals ad, stating very frankly that she is looking to lose her virginity to a caring lover. For whatever reason she is not finding any luck with young men in her own circle; I suggest she broaden her horizons. Placing a personals ad will bring in men who aren't scared of having sex with a virgin, and at the same time she can be honest with her partner about her virginity so he can be patient and gentle with her. (Of course, screen the applicants, meet Mr. Likely in a public place first, use condoms, etc.)
By that same token, if she doesn't want to place a personals ad, perhaps she might gain from broadening her real-life horizons. Is there something about the men she is approaching now? Are they all a bunch of good-looking yet shallow yuppies who want Mata Hari in bed with them? Perhaps a more down-to-earth choice of man is warranted. The LW doesn't need to lose her virginity to her true love, just a nice man who will treat her with consideration and to whom she can tell the truth.
In any case, the LW shouldn't mythologize her first time in such a way that only Mr. Perfect will do. Go for Mr. Right Now. He needn't be the one you want to marry or even date. He can be older or younger than you, in a different social class, not looking for a relationship. (Unless the LW is, in fact, looking for something long-term.) Believe me, losing your virginity isn't going to be a romance-novel experience. Don't hold out for Mr. Darcy.
If you're fishing and have to throw all your catch back it's a signal you're fishing in the wrong pond.
I was pretty much in the same boat as the letter writer, except for the fact that I hadn't tried nearly as hard as her to lose her virginity. It finally happened at 26 after almost 4 months of trying (with luckily, the same understanding guy). I'd done toys, masturbation, etc., and thought the hymen issue was pretty much overwith. But what they don't tell you is that by this age, if it's not dissappeared it tends to get thicker, also it's much more likely you'll be stressed out and clamp up during the crucial moment. I read online about WAY too many women who got married at my age and tried to lose their virginity on their wedding night only to have it ruined by not being able to.
My advice -- go to a good, open-minded ob/gyn. Make sure it can happen. If there's any reason to think it might hurt or you might clamp up, make sure that they physical reasons for this are taken care of. For me, I had a laser procedure (under full anesthesia) that made the hymen dissappear ... and even then it took 3 weeks after that to have final success.
Other than that -- whether you decide it's a one night stand, or maybe someone who you like and trust. Make sure you're okay with it. There's no need to rush it, and the first time's really not any good anyway, so just do it on your own time. I personally would recommend doing it with someone you're in a relationship with, and telling them before hand. If they "freak out" then that wasn't any kind of relationship anyway, and they didn't know you. Of course this might mean you have to wait till 26 (like me) or later, but it will also be a much better experience overall.