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DOING DAT THANG

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DOING DAT THANG

By Lainie Speiser

At this writing, I have just completed promoting August Anal Awareness Month. It’s a real thing devoted to all things “in da butt,” as I call it after the late 80s hit, Da Butt, by E.U. I used August Anal Awareness Month to promote my clients who are anal experts such as my client Vicki Chase who has won many awards for her anal expertise. I also booked Dr. Andrew Kramer, a well-known urologist on “The SDR Show” who gave hosts Ralph Sutton and Big Jay Oakerson prostate exams. By the end of the month you’d think I’d have run this into the ground, but no, not at all, both men and women are endlessly fascinated by the inner workings of “da butt” and although Vicki Chase may have gotten bored of talking about it, not one radio show, podcast and website has. Anal is still one of the holy grails of sex. If you have met a woman who is not only open to it but very into it, I say keep her, she is a rosebud, literally.

I’ve written six books and covered many sex topics, threesomes, role play, blowjobs. I’ve gone deep with them all, except for anal. My history with anal has been spotty; it’s never made it on my top 10 of sex moves, and I didn’t even try it until I was 32 years old. I had a boyfriend who didn’t understand how a woman with an apple butt like mine would not want to give anal sex a try. Our relationship wasn’t the best one. It started out well, but by the time he was putting pressure on me to submit to anal sex, it became more of a test of wills. We both worked for the same porn magazine: he was an editor, and he even wrote fictionalized erotica about what my first time having anal with him would be like. It involved a lot of lube and my fretting about the size of his penis going into my tight pink butthole. He did the same thing when he was pressuring me into being with another girl with him watching and jerking off. In fact, if I ever wanted to know what this particular boyfriend wanted from me, all I had to do was read the advance copy of Gallery Magazine’s erotic story section, and I was grateful that I kept this relationship a secret from the entire staff for this reason.

I did eventually give in; I made a deal: I would have anal sex with him if he wore my black lace panties for an entire day. It was a sucker’s bet. Little did I know he enjoyed wearing my underwear and on a trip to upstate New York, I was slated to break my anal virginity. To prepare, I did what every girl should do: ask my gay male friends about it. My friend Paul, who was usually in the submissive role, told me he didn’t really indulge in anal sex that often unless the man was super hot and he was unbelievably turned on. My friend James, who was a top, had anal sex for the first time recently and said, “Bring some blow. It really helps open you up.” But I knew from experience that blow makes most men Mr. Softie, and I didn’t want to bring complications to this already tenuous situation. So, I smoked a bit of weed, had several cocktails, laid on my stomach and braced myself. What I felt was a slight, burning-stretching sensation and then pressure, the more he carefully pumped the more comfortable it got but make no mistake I was relieved when he came, and it was over.

But this wasn’t the last of our anal experimenting. This guy, like most bullies, was a secret submissive and we explored a lot of ass play on him, which I was happy to do given the alternative. So, I learned how to work a prostate with my fingers, tongue and a strap-on. The latter was when I discovered how hard men really do work for us; it was exhausting, and again, I was relieved when he came, and it was over. But once he got a taste for ass play there was no turning back. He implemented it into everything we did when we 69’ed and when I was riding him on top, I had to do a reach around and get my fingers in there. To say I was a good sport didn’t even cover it, and when we inevitably had a nasty break up, I said, “Good luck finding a woman who’s open to strap on action.”

The next time I had anal sex I was in my mid-30s in a really, gorgeous midtown Manhattan apartment with a man I met at a cigar bar who was in the winning business. I’m going to call this guy the name his friends did, The A Man, because he was famous for getting the ladies to not only agree to have anal sex but also enjoy it a great deal. The A Man was an attractive middle-aged man with thick salt and pepper hair, green eyes, and a beautiful body thanks to his big hobby of cycling. He was a smoothie; he didn’t push his agenda right away. He just fucked me stupid for hours, taking breaks for cigars, wine, and cheese and then continuing again.

The A Man knew how to loosen a lady up, literally, and when he got me on my back with my legs in the air, he slipped it in casually, with no muss or fuss. “Oh my god, this actually feels really good!” I remember saying, looking up at his happy, self-satisfied face. Truly, I was having a great time. He deserved his nickname, and I got lost in the moment. That is until I opened my eyes and saw The A Man talking on the phone while fucking me. “Bro I’m fucking this hot redhead with huge tits and she’s totally loving my dick in her ass,” and then he pointed the phone to me and said, “Tell him how much you love my dick in your ass, Lainie,” he said perfectly casual and normal. Now I hate when friends pass the phone to me to say hello to their family, boyfriend, girlfriend, whoever and I didn’t like in this vulnerable position either. “What the fuck is wrong with you?” I shrieked and then out of nowhere managed a powerful orgasm. The A Man had no shame, and neither did I, but that was a bit too much, even for a freak like me, and never saw him again.

A year or so later, I found myself learning more about anal sex while writing Confessions of the Hundred Hottest Porn Stars. A book where I interview 100 porn stars about their sex lives off camera. And while many women didn’t have anal sex on camera, most of them told me they loved it off camera. Anal sex in the porn world is something you save for a rainy day when you really want to make as much money as possible because your fans have been clamoring for it. Once you do it, you will never make that high rate again, so it’s very important that you negotiate a kick ass deal.  I talked to some women who can only achieve orgasm through anal sex, and other women told me it’s much easier to take the monster dick of say, the performer the legendary Mandingo, in da butt than in da puss. “There’s more room than you think back there,” said one porn star. “It’s a lot more comfortable to take 14 thick inches there.” When I interviewed porn star Sinnamon Love and confided in her about my own strange relationship with anal, she said, “Anal sex is so much better when you have double penetration, seriously that’s the best way to go.” She said the sensation of being airtight is like no other, and I thought about engaging in my own way, having a dildo in the front and the real thing in the back, but it never was that important to me. The overall message I learned in writing that book was if you want to explore your sexuality in a safe environment where everybody gets tested, then a career in porn may be for you.

The last time I engaged in anal sex, it was my idea, because I was having an intense fling with a hot man who was also a devout Christian and had never tried it before. Our whole sexual relationship was built on taboos, so I insisted he should at least try it once. This time I was the instructor, and after much foreplay and regular intercourse, I lubed my Christian Single up and walked him through the process, very slowly, and it was nice and intense. At the end of the day, what gets me off is what’s going on in my head. The idea of corrupting this sexy but safe person turned me on endlessly, we had a true passion for each other, and I was thrilled to be the woman who broke this boundary. But he didn’t come, he waited until I did, then asked if we could do it the regular way again, which for us was doggy-style. He later said, “I don’t know, why walk in the gutter when there’s a perfectly nice sidewalk right in front of you?” I don’t think anything on my body should be compared to a sewer, but I got the message. Perhaps one day if my publisher asks me to write “The Anal Sex Beginners Guide,” I might give it another chance but until then, I will restrict anal play to a tongue, which feels fantastic, but that’s another story.

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