Dear Sasha: I had a one-night fling with a guy while I was on holiday this summer. Everything was going super well until he took off his pants and I saw his massive penis. I'm pretty sure he noticed the terror in my eyes and was extremely gentle, but it still hurt like hell going in. Once he was in, it was awesome, but when we did it a second time it became really irritated and we had to stop. I know I was really wet - he kept making comments about how juicy my pussy was. He's coming to visit soon and I'm wondering if you have any suggestions on how to make this less painful. » Petrified Pussy

Dear PP,
While it's true the vagina is one supernaturally springy body part, there's only so much skin you can handle without a fully dilated cervix and an epidural. Cory Silverberg of Come as You Are (www.comeasyouare.com) and I went over a few possible solutions.

Cory suggested you visit your local gay toy store (Priape, 1311 Ste-Catherine E.), where you'll find some combat-sized butt plugs. Masturbating with a gradating toy, at your own pace and rhythm, is an excellent way to prepare your vagina for big fun. He also suggested going to a more mainstream sex store and looking for what is known as a donut, which is part of a penile-elongation pump and is also sold separately. It is exactly what it sounds like, and if you can slide it down to the base of your lover's penis, you won't have to take in his full length all the time.

Fisting is also a great way of learning how to relax and control your vaginal muscles, and though you don't require a partner for this (see the book A Hand in the Bush by Deborah Addington), it does help. Although you may have gotten really wet, I'm going to recommend a silicone-based lubricant called Eros. You may find the added and consistent lubrication lessens friction irritation. Just be warned, if you're prone to vaginal infections, this may exacerbate them.

Dear Sasha: My boyfriend and I want to try out a role-playing fantasy: meeting up in a bar as "strangers" and having a one-night stand (presumably at a hotel). This fantasy really turns me on in theory, but it's our first time doing something so elaborate and I'm wondering how to pull it off. Any tips on how to make this idea live up to its potential? What are some ways to avoid feeling contrived while maintaining our characters? What are the dos and don'ts of a pretend affair? » Hoping for an Out-of-Body Experience

Dear Hoping,
Many years ago, my friends Liz and Paddy came to the club where I was working to see if I could get off early. They were celebrating their second anniversary, were suddenly bored, and thought I might entertain them. At the time, I was taking improv classes and was applying the skill to all my life's activities, including my job (for which I was eventually fired - strip club patrons can be so humourless).

For laughs, we went around to bars with a different set-up for each one. In one instance, Liz and I pretended to be lovers apprehended by her boyfriend, Paddy. In another, Paddy and I pretended to be caught in flagrante delicto (in the act) by his wife, Liz.

Do you know what made this all seem so real, and so much fun? The bartenders ("Ladies, please break it up! Is a guy worth all this?" etc.), especially those who gave us free drinks when they realized we were a merry band of players. Of course, you'd have to keep up the charade, but I think that's where you'll find the power of the caper: through unsuspecting onlookers. To ensure this, make contact with the bartender, and have a mutually agreed-upon back story - perhaps you're recently single, you're from out of town, maybe you guys met online and this will be your first face-to-face. Can the bartender recommend a good hotel, "just in case"? Knowing your transaction is being observed by a third party raises the stakes, and will force you to rise to the occasion.

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