By Chuck Strouse
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By Pepe Billete
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By Kyle Swenson
Since I moved to Miami from Montreal six months ago, I've had a wild and crazy time taking advantage of all of South Beach's decadent indulgences (mostly the women). But it all came to an end when I got engaged to a perky and intelligent Cuban Jewess nearly two months ago. She's an absolute darling and open to almost anything once the doors close. But she's totally against anal. I've never done it and had hoped to explore the forbidden zone with a lady I had feelings for. All of my guy friends have done it and they constantly tease me about what I'm missing, so now I'm reeeally curious. Kitty, please save me and tell me how to get my lady to f-i-n-a-l-l-y give up her other hole. Or at least tell me it's no big deal and I shouldn't try it till I die. Help!
Butt I. Wannit
Hey, Mr. Wannit:
The anal experience would not only add a bullet point to your raunchy resumé, but also add another layer of pleasure to your life. I can't tell you it's no big deal; not everyone loves taking a ride up the chocolate highway. Pitchers and catchers alike complain the initial entry isn't that pleasant. Some equate it with prison lovin', and others can't overlook the reality that pungent packages fly out of that area daily. Then there's the other half. They take full advantage of the body's most nerve-sensitive spot. They love it, can't get enough of it, and think it's the best thing since virgin pussy. The Bible isn't so wild about anal copulation, but the Talmud says it's cool as long as both parties are into it — so your Cuban Jewess wouldn't be breaking her law. It's possible she refuses to let your peen enter her back door because she can relate to one of the issues I listed. Or maybe she has irritable bowel syndrome and doesn't want to subject you to the side effects that might occur if you part her cheeks. Please don't make me explain why doo-doo on your dipstick could forever traumatize you and possibly make you call off this quickie engagement.
And speaking of quickie engagements: Maybe she won't let you travel the Hershey highway because she hasn't known you long enough to trust you to go there yet. Trust is a big factor in building intimacy, so maybe she just needs more time.
In the meantime, if you're still interested in going up her dirt road, have a chat with her about it. Don't do it during Sunday dinner at your mom's house; bring it up while you two are in the throes of passion. She's more likely to be open to a little experimentation once her juices are flowing. Pose the question real sexy-like in her ear and maybe introduce a little finger action to get her interested. If she still resists, what you do next is totally up to you, but keep in mind that some ladies might question a man's sexuality if he's too adamant about this particular issue. I'm not saying you go that way, but a woman's natural gaydar begins beeping around the third or fourth request. So just relax — she might be saving that ass for the wedding night.
Got a question? E-mail firstname.lastname@example.org.