losing her virginity

I've received a lot of interesting emails from people whom I don't know since I began writing this blog. Sometimes folks write and ask me for my advice about sex. I don't know that I'm any kind of expert, but I guess I convey a certain knowledge through my posts.

A girl I'll call Ashley wrote to me recently. She's 20 and a student at a prestigious East Coast university. She sent me her picture, and she's a very pretty girl, with a wonderful voluptuous figure, narrow waist, and sweet face. She looks like a Vermeer painting come to life.

She's also a virgin.

Ashley badly wants to lose her virginity, but she doesn't want just any guy to do it. She would like the event to be special and memorable. Ideally, she wants multiple sessions with the guy so he can be something of her teacher. For that reason, she's hoping the man would be somewhat older and sexually very experienced. As she wrote in one email to me, "I don't want some clumsy boy doing this." (I should also add here that I obtained Ashley's permission to write this entry.)

During her summer break, she set a goal for herself to lose her cherry by the end of the year. How to go about this, however, has been something of a challenge. She contemplated placing a personals ad explaining exactly what she wanted, but quickly concluded that would probably attract the wrong kind of men. She also read on the internet about how a woman arranged with a Nevada brothel to lose her virginity -- for quite a lot of money -- but decided that was not for her, either. This was a personal quest for her, not a publicity stunt.

She did end up placing a listing on several free online sites stating that she was looking for a somewhat older, experienced man to educate her about sexuality, but she did not go into any details about losing her virginity. Needless to say, she received a flood of responses and, as she wrote me, "99 percent had their fate quickly sealed with the delete key."

She was very intrigued, however, by two guys who responded with their pictures. Both are very well educated, very good looking, articulate, and not at all pushy. She wrote back and decided to tell them the truth -- that she's a virgin and is looking for a special man to awaken her sexually. Both responded with interest, although one was somewhat avuncular and questioned whether this was something she really wanted to do.

Ashley and the two guys emailed each other back and forth a few times, then progressed to IM chats, then on to phone calls. She really likes both of them but has yet to meet either in person. She said that neither has been pushy about "the event" or setting up any kind of face-to-face. Her instinct is to arrange a meeting in a very public place so she can get a sense of each guy and then decide what to do.

She asked my advice about this, and I told her I thought it sounded like a good plan. I also suggested that, if she ends up selecting one of these guys, the deflowering should happen in a hotel room so he won't know where she lives; I don't think going to his place is a good idea. I also recommended she tell a friend where she'll be, and that friend can contact the authorities if she doesn't report back at a predetermined time. I also suggested she provide her friend with the guy's telephone numbers and home address.

Ashley has also discussed her quest with a married graduate student who serves as a teaching assistant at her university. As it turned out, unbeknownst to Ashley, this married woman is a sometimes swinger and thus offered her law student husband to perform the service. Ashley described the husband as very attractive and sweet; she's met him a few times. The wife also offered to join in to make sure all went well if Ashley wanted.

Ashley asked my advice about this, too, and my instinct was not to go down that path. I've known a few swingers, and they generally have quite open attitudes about sex because they're involving themselves with people who have the same mindset. Swingers, however, generally do not form attachments with their sexual partners. But Ashley is not a swinger. What would happen if she became attached to the husband? What if he became attracted because he knew she was?

I just think this is a dangerous place to go. Not physically dangerous, of course, but emotionally dangerous. She could end up hurting their marriage and her friendship with the wife.

Ashley concurred this was probably wise and had already come to something of the same conclusion on her own. She was asking my opinion more for validation, which I was happy to provide.

So for now she's progressing slowly with the two guys she met online. She says she likes both and may have a hard time choosing which one. I think once she meets them face-to-face, though, she may have a different sense. Sometimes a guy seems one way on the phone, but when you meet him, he's not the guy you thought he might be.

Ashley has promised to keep me up to date with what happens and, if anything memorable goes down, I'll report it here. So stay tuned!