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Dear Em & Lo,

I'm a 24-year-old virgin in just about every way you can be--second base is about all I can claim. It's not for religious reasons, and I'm not waiting for marriage (hell no! Must test-drive the car first). I held off in high school, and then held off through college because I consciously wasn't ready for the responsibility that comes with being sexually involved with someone. Now I'm just waiting for a guy who means enough to be worth giving it up, someone who I really trust and who is patient with me.

But that's not my dilemma. I've waited so long now that I'm scared about that first time. The idea of the pain is my biggest tangible fear, I think. I've heard nothing but horror stories from friends about their first times, and as a woman with quite a low pain tolerance, I've worked myself into a tizzy worrying about it.

I'm totally open to the idea that good sex comes with practice. But clearing this hurdle is holding me back from doing much dating at all to avoid the added pressure.

What do you suggest to help me ease my anxiety (and ensure it doesn't hurt too bad)?

Still Waiting


Dear S.W.,

We've got one word for you: Masturbate, masturbate, masturbate. Here's why:
  • You should know what you've got, how it looks and feels, and how it likes to be touched before anybody else does. Don't leave it a mystery only to be solved by the first sexual Sherlock you allow in your pants. Knowing your body intimately will give you confidence when you finally share it with someone else.
  • Studies have shown that women who masturbate regularly have more satisfying partner sex.
  • Pain during first-time sex for a woman might be caused by the hymen breaking fully. If you're already in your 20s, though, chances are it's already broken substantially, via tampon use, self-diddling, horseback riding, or other rigorous exercise like gymnastics or cheerleading (hello, splits!). But if you think it may still be a problem, then by all means invest in an insertable vibrator or dildo to help your body adjust to that filled-up feeling. You could even start small, and work you're way up in girth. Even if popping your cherry isn't a concern of yours, this is still a good idea!
  • Another cause of pain during first-time sex may be not enough lube, perhaps because one is too scared shitless to be really turned-on. There's no shame or harm in helping things along with a little man-made glycerin-free water-based lubricant. In fact, it can help make any sex--first time or 1,000th time--feel better.
  • Finally, another possible cause of pain is a guy who doesn't know what he's doing (i.e. he goes in like gangbusters without any warm up). He should move slowly and build up intensity gradually, checking in with you along the way to make sure you're okay with everything (insist he does if he's not). But if you're waiting for a guy who is special, chances are he'll put your pleasure first and proceed with sensitivity.
If you re-read the above, you'll notice we referred to first-time sex, not first-time intercourse. Our society places so much emphasis on intercourse as the be-all, end-all of partnered sexual activity, but handwork and oral are sex too! Those might be just as erotically satisfying for you than intercourse--if not more--and they certainly can be just as intimate and awe-inspiring. So make sure during your first time going beyond second base with a guy that you're focused on the whole experience and not just on slipping tab A into slot B. Being an avid masturbator beforehand will help you in this endeavor.

Have fun storming the castle!

Em & Lo


9 Comments

said:

I was 22 my first time and I have to say that I couldn't have imagined it going better! I can't say I remember pain, slight discomfort, but he was really great, took his time, lots of foreplay (read plenty of natural lubrication!), oral sex and manual stimulation before the actual insertion. I've masterbated for as long as I can remember and used vibrators for awhile too, definitely worth it!

Try not to stress too much, let him know what works for you, play around and have fun!

E said:

I didn't have *any* pain or discomfort at all my first time, you might not either! I hadn't masturbated much (and never used a vibrator or dildo) but my bf and I had been fooling around for a few weeks before we had intercourse. I was super turned on, which I'm sure helped. It wasn't the best sex I ever had, but certainly nothing to be scared about.

Jenny said:

I was 23 when I had sex for the first time and it was enjoyable for me too and it didn't hurt....at all. So see? Three girls who say it isn't painful!

Jen said:

Contrary to the other three girls, my first time was pretty painful and very unfulfilling, and I was 25. My boyfriend and I had been fooling around for a few months prior, and we planned "the big day" around a weekend that my parents would be out of town. I had gotten so worked up about it, that my body just shut down. We had lots of foreplay and used lube, but it just wasn't happening. I was bummed, but he was very supportive and patient, and a few weeks later, we had success. I guess the moral of the story is if at first you don't succeed, try try again!

J said:

My first time happened in college. I will admit it was quite painful, but only for a few seconds, then it was very enjoyable :) I would suggest you not work yourself up about it too much in advance. Have a comfortable discussion about sex, especially protection, ahead of time - but don't set a specific time. That way you can initiate it when the mood strikes you. I little planned spontaneity helps to keep the pressure off, making it much easier to feel and stay turned on!

said:

I was petrified about my first time, too. It kept me from having PIV sex with my boyfriend for the first THREE years we dated. We employed every other method of relieving ourselves together until then, and I believe this helped a great deal for when the big event finally happened, because we knew each other's bodies intimately. Intercourse doesn't always give that.
It turns out that me, the girl who had nightmares about the pain I was sure would happen, did not have a single problem. It feels strange at first, since you're not used to the sensation, but I was ecstatic because the "myth" of it possibly not hurting at all was true for me. It might be true for you too. And even if it DOES hurt, I think the pain is worth the ultimate joy. Waiting was probably good for us, but sometimes I wish I had started doing it earlier. It's the most incredible action I've ever engaged in.

said:

I have been in my current long-distance relationship for two years, and I find that it hurts the first 2-4 times after we've been apart for several months, though the sex after this makes it absolutely worthwhile. How common is this sort of problem, and what should I do about it?

Stacey said:

I'm on the same situation, I'm 26 and still VIRGIN. My boyfriend and I are planning to go on holiday together next month. I know what will happen because will be together in the same room for 1 week. I'm really scared because he is quite tall and I know his down under is quite big. Need your advise....Cheers!

said:

I was 28 when I had sex for the first time. I had been waiting until marriage, but decided in my early 20s to give up religion (and virginity). The "preparation" lasted about 2 years, and way longer than I wanted it to.

I decided that if I couldn’t bring experience to my next relationship, I would bring knowledge. I read several books on sex. I was already good at giving myself orgasms, but I got a vibrator and used it to relax and stretch my vaginal muscles. (This is a must for preventing pain!)

I became obsessed with finding the right guy to have sex with. He didn't need to be a "forever" guy, but he had to be gentle, patient, and understanding. I joined Match.com and was on there for over a year until I met him. We clicked immediately, and I knew he was trustworthy and kind.

He seemed ready for sex on date three, but I wanted to wait. He was actually relieved when I told him I was a virgin. (He had slept with two people previously, both of whom had expressed shock when they found out how "little" experience he'd had.

I never, ever thought I'd do this, but we ended up having sex on date six! It was wonderful. I had no pain, and it was as enjoyable as any other time we've had sex since.

I think a lot of women's horror stories about losing their virginity are about having sex with a guy who is as inexperienced as they are. There are lots of reasons why waiting until your mid- to late-20s can be a great thing:
- guys your age have experience
- you know yourself better (what you like in a man, what you're comfortable with, your values, etc.)
- you know your body better and you feel more comfortable with it
- you’re emotionally mature

In case that's not enough, look to the super-sexy Tina Fey. She apparently waited until her late 20s, too:
http://extratv.warnerbros.com/2008/12/tina_fey_americas_sweetheart.php

Hang in there. Keep looking, but don't do it just to do it. Find the right guy. And don’t let anyone make you feel ashamed of waiting. It will happen for you, and it will be great!

When I meet my boyfriend (my “first”), I was just looking for the right guy to have sex with. But I found a truly wonderful man, a friend, and a supporter. You don’t have to be cynical about sex and love. If I found both in one person, you can, too.

Good luck!

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Em & Lo, more formally known as Emma Taylor and Lorelei Sharkey, are the self-proclaimed Emily Posts of the modern bedroom.

Dr. Kate is an OB/GYN at one of the largest teaching hospitals in New York City.

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