Dealing with the Big Reveal: Coming out as a virgin

I recently got a note from Ferrette (who did a wonderful First Person for us a while back) with this question:

"Have you ever written any articles about the experience of "coming out as a virgin" to others? Like to someone you meet, or date, or even friends? I've been thinking about this a lot lately, how when the "big reveal" happens, others will be shocked, or pitying or sometimes even hesitant to hook up (the latter is one I'm familiar with).

Of course, there are also those that don't care, or are friendly no matter what. But it does seem to me that the older one gets while retaining some vestige of virgin means that these awkward conversations will just become more frequent. Course, my turning 26 recently may just have me over thinking everything."

By way of reply, here's a video of Dan Savage at the University of Montana who addresses the comment "I want to lose my virginity but I'm scared" by comparing it to bungee jumping:

"Eventually you just have to jump. You're all strapped in. You're ready to go. There's a line of Australians behind you and they want to go next."

Dan also feels strongly about telling your partner that you're a virgin. It's at 2:00, above.

I first saw this video at Diary of an Accidental Virgin who agrees with Dan:

"Why would you want to sleep with someone who is afraid of or won’t accept such a simple truth about you? Why do it with a person who views you as “less than” because you’re a virgin? Isn’t that the sort of person you wouldn’t want to have that experience with?"

The thing is, there are so many people out there either not sexually active at all, or who haven't been sexually active for a long time. If more people were honest about it, maybe it wouldn't be such a stigma.

On the other hand, I didn't tell the first guy I had sex with I'd never done it before. I was in my 20s and he assumed I was experienced, but he figured it out pretty  quickly due to my utter lack of skills. It was awkward. It was embarrassing. But I don't think it would have been less so had I explained the situation before things got going.

Let's face it: Doing anything for the first time is awkward, and sex is no exception.

What do you think: Tell or don't tell? Or just jump off that bridge and hope the cord is strong enough?