The Crap Shoot

I was 26 years old the first time I had anal sex. I was dating V, a conservative, deliberate man with Howdy Doody good looks. V and I were doomed from the start, being polar opposites; but the sex was amazing because...um...we were polar opposites. Life can be so unfair sometimes.

One night, V shocked the hell out of me by asking if I wanted to get fucked in the ass. Imagine those words coming out of Mr. Doody's mouth; shocking right? And fucking hot as hell!!! I immediately rolled over onto my stomach, ass in the air, hands spreading my butt cheeks as far as I could (even back then I was an adventurer) while V lubed up and buried his cock slowly in...mmmmmmm...I came over and over as V inserted himself into my tight little hole, again and again and again. Who would have thought?

I also discovered that V loved a finger and a tongue in his ass (though not at the same time). It took me a long time to get up the nerve to put my finger in; I used desensitization - every time we had sex, my finger would creep millimeters closer to bulls eye. Until finally one day...well, after that he practically rammed my tongue in his bum. That's how hard he came.

The ass is off limits to a lot of men, perhaps because they think it is somehow "gay". However, the explorers among us know that there are a lot of sensitive nerve endings back there, and that the male prostate is the equivalent of the female G-Spot.

Some women feel that anal sex is degrading and dirty. Well...that's because it kind of is. That is what adds to the pleasure of getting a cock deep in the ass. It's also naughty, kinky and nasty...everything (great) sex should be.

Since V, ass play has been a regular part of my sexual repartee. If it's on the menu, I'll order it from time to time. There is an art to backdoor sex, and certain cardinal rules. Ladies and gents take heed...good lovers know that you need plenty of lube (did I mention that you need plenty of lube?) and that you need to start out slowly...ease into it, so to speak...until the initial pain (and goddamn, I'm not gonna lie...it hurts) turns into intense, deep shocks of pleasure (be patient; it will happen). Believe me, with the right lover, anal sex will give the intrepid the most intense orgasms (yes, orgasms -plural!) they have ever had. Finally, it goes without saying that cleanliness is an absolute must. However, as I have discovered, there is an

expiration date for cleanliness, or AED (Anal Expiration Date).

My current boytoy, Mr. Yummy, and I are still in that experimental stage in bed. We'd been hinting around the subject of anal for two weeks when it finally came up. Although Mr. Yummy is an artsy, think-outside-the-box type that will try anything two or three times, he's also polite and respectful to a T. Sometimes I've got to coax him a bit and give him the green light here and there until he takes control.

Finally, he tip toed his way around the subject and asked how I felt about anal.

"I love it," I told him, "you?"

He looked like he had hit the jackpot. "Me too," he said, eyes bulging out of his head, cock bulging out of his trousers, "it's the condom I can do without."

"Condom?" I asked, confused.

"Well, yeah...without a condom you can't really go back to other stuff without washing up first."

Oh Mr. Yummy...you have so much to learn.

"Look," I said, "I make sure I'm clean and ready to go beforehand.You should feel free to help yourself anytime."

Well, he did...that very night, which I had suspected...and I was ready and prepared for it. And when Yummy pulled out...just as I said - clean as a whistle. It had all gone well...orgasmically well.

Here's where the AED comes in. While I am always clean and prepared for anal at night, well...things are TOTALLY different in the morning...especially before I've had a chance to use the bathroom. Continue reading at your own risk.

Yummy sleeps over on a Friday night; he's worked late and I'm sleeping. Being a gentleman (and probably because he was too tired to get it up), Yummy lets me sleep instead of waking me up with a good fuck. The next morning is a different story. Yummy wakes up with a hard-on (are there any men out there who don't?) and it's all systems go. I'm on top, then he's on top, then he's behind me.

After several minutes, Yummy asks "OK; now where can I go?"

Suddenly he's poking my ass with his cock and I feel lube running down between my butt cheeks. Rule one (lube)? Check. Rule two (go slow)? Check. Rule three...

After a few orgasms, I tell him to stay inside my ass while I roll onto my back. But contortionists, we're not. He falls out...and there's a cacophonous pause.

"Um...Tango? I'm gonna go hop in the shower. I think maybe we need to change the sheets."

I look down...and horror of horrors... LEAKAGE! I had felt something wet running down my ass but I thought is was lube, or pussy juice or something. Nope. LEAKAGE!

While Mr. Yummy was in the shower, I cleaned myself up and tossed the sheets in the washer to rid myself of the evidence. We didn't mention the LEAKAGE for the rest of the morning.

That afternoon, Yummy sat me down. "Tango," he started. "there's nothing to be embarrassed about. It's just that the AED had passed. I guess, in the morning, anal is really just a crapshoot, and sometimes shit is going to happen."

We looked at each other and started laughing so hard we almost peed our pants. Which reminds me...perhaps it's time to introduce him to water sports...

I am extremely lucky to have found Mr. Yummy, who quickly became quite skillful in the art of anal sex. He has the most amazing touch, the magical touch that makes me cry out and beg for more...every time we fuck. What's so cool about sex with Yummy is we never talk about what we are going to do. One position flows naturally into another, and so on...it just kind of happens. Nothing is planned, nothing is off limits, everything is an opportunity for giving and receiving pleasure. Sex with Yummy is like an intricately choreographed dance...except it so totally ISN'T.

So ladies? Don't be afraid, or shy. And men? Trust me on this one. Once you have a finger or tongue in your ass, there's no going back. After all, a hole is meant to be filled.