I am a bastard and a rogue and a roustabout and a manwhore. My sexual exploits are vast and strange and complicated—and, to be quite frank, a raging majority of them are highly shameful. I have had many unusual sexual experiences, mostly because I am an unusual man.
Here are only a few of the endlessly weird ways that the wayward and wanton women in my life have taken me from mere arousal, across the Sea of Lust, up the Mountain of Pleasure, and all the way through the Gates of Orgasm.
1. THE FOOT JOB
As I was orally pleasuring one freckled redhead on one lonely winter’s night, I noticed a sudden tugging in my groin area. Soon enough I realized that this fair young maiden had clutched my male organ with her feet the way a monkey would peel a banana. She furiously pumped me with the abandon of a musky primate and brought me to completion with her feet alone.
2. DINNER TABLE BLOWJOB
A few years back I was dating a woman who had a whole “retro” fetish which not only included Marilyn Monroe and Elvis memorabilia everywhere in her apartment that you turned, it also included a real kinky “50s housewife” roleplaying scenario. She put on a vintage dress and checkered apron and made me a pot roast with baked potato and apple pie for dessert. She also insisted on crouching beneath the dinner table and eagerly blowing me while I dined like a king.
3. HOSPITAL ROOM SHAGGING
The same retro girl broke her leg in a scooter accident not long after our dinner table blowjob, and being the gentleman that I am, I visited her in the hospital after they set her knee in a cast. Within five minutes of my arrival, she began coyly complaining that we hadn’t had sex in a week. I pointed to her leg cast and said, “Sorry to say, but I think it’ll be a little longer.” Then she winked naughtily at me and I dropped my pants and negotiated my way around all the wires and cords and mounted her—no mean feat, considering that her leg was in a cast. It lasted less than a minute but was the best sex of my life.
4. ORAL PLEASURE IN TRAFFIC COURT
Life and opportunity and desperation sometimes lead me to make unwise decisions, and that was the case about a year ago when I dated an exotic dancer for about six weeks in the middle of winter. She accompanied me to traffic court one morning in mid-January. The courtroom was massive and cold and drafty, and there were only about a half-dozen people sitting in the wooden seats. We sat way in the back, and hiding under the parka I’d removed, she blew me to completion while the judge and some scofflaw were arguing about speed-limit signs.
5. BAR BATHROOM BLUMPKIN BINGO
If you don’t know what a “blumpkin” is, you will hate me forevermore for being the person who introduced you to this highly distasteful term. I was bartending a few years ago and late at night a frequent booty call of mine showed up right before closing with a sly look in her eyes. I tried explaining to her that I’d eaten some seafood for dinner that had given me an upset stomach, but she didn’t care. After the bar had closed, I excused myself to go to the men’s room. Impatient, she followed me in there about a minute later as I was seated on the toilet, trying to take care of business. This brave and faithful lady orally serviced me while I defecated, and if that’s not love, what on Earth is?
6. BLOWUP DOLL VOYEUR
For my birthday this year, my faithful and devoted girlfriend gifted me with the cheapest plastic blowup doll she could find at the sleaziest sex shop in town. She thought it’d be funny if she filmed me fucking it. After some initial awkwardness (basically, before I realized that olive oil is a good lubricant for cheap vinyl), I performed sexual intercourse with the blowup doll while my girlfriend filmed me on the iPhone, laughing harder than I’ve ever heard anyone laugh in my life.
7. MANNEQUIN PROSTATE MASSAGE
I have no shame in telling you that I enjoy the occasional prostate stimulation, but I am blushing as I type when I tell you that a frequent FWB of mine—who’d always finger my ass when I fucked her missionary style—tricked me one night when she stuck the adjustable middle finger from a detached mannequin hand up my hole without warning. It felt strange, but I didn’t say anything. When she revealed her little “trick” after we were done, we laughed so hard that we started having sex again.
8. SPATULA SPANKING
After making me pancakes for breakfast one morning, a girl I’d been seeing confessed to me that she was ovulating and was horny as fuck. Never one to deny a woman what she wants, I took her by the hand and led her into the boudoir. In her other hand she held the steel spatula she’d just used to make pancakes. In the course of our sweaty, loud rutting, she began spanking me harshly with the steel spatula. First, it stung. Second, it felt good. Third, I finished quickly.
9. “STOP! IT’S TOO DEEP!”
The worst thing any man could ever want to hear is, “Is it in yet?” This was not a problem for me one summer about five years back during a one-night-stand with a girl I met at a show. Cramped together in this old-fashioned wooden Amish-looking bed, I found myself “delivering the groceries” to her so aggressively that she suddenly squealed, “STOP! IT’S TOO DEEP!” And with that I stopped—not out of courtesy, but because it turned me on so much to hear that I was capable of driving it in “too deep,” I lost all control and nutted all over the sheets.