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The Straight Man's Guide to Receiving Anal Sex from Your Girlfriend

On more than one occasion, a woman has asked me if I wanted to do "butt stuff" when it became clear that coitus wasn't cutting it anymore. Assplay is a logical next step in a male/female sexual relationship.

Relationships, like produce, milk and reality television stars, have a shelf life. Most couples find that after a few weeks, months, or years, the luster fades and the initial carnal fury that brought them together has dissipated. The moldy codgers who get past this sexual brick wall do so by developing an elaborate series of coping mechanisms.

Infidelity is common in scenarios where one or both sexual partners become fed up with plain vanilla missionary. Sometimes, the couple just resigns themselves to erotic entropy, and embraces a sort of marital celibacy typified by the nightly ritual of 'reading magazines' or 'checking the scores on ESPN.' In this instance, going to sleep unfulfilled is preferable to even trying.


For those of you out there who want to tell me how love can sustain itself over decades, allow me to offer you the following completely non-scientific statistical breakdown:

-4% of the population falls in love and remains in love the rest of their lives

-21% of the population commits suicide after one too many viewings of the Tom Hanks/Meg Ryan comedy You've Got Mail

-25% of the population masturbates more than three times a day

-3% of the population is asexual

-40% of the population has boring, meaningless sex until they die

-7% of the population has casual, freaky fetish sex with multiple partners until they die of being too happy

The goal of every human reading this article should be to get in that 11% of the globe that either finds a soulmate or fucks a neverending series of holes with verve and vigor.

The easiest way to go about joining the 11 percent (which is far more vital to the national discourse than the 99 percent or the 47 percent) is through the back door. Anal sex is the first stop on the Save My Relationship World Tour.

On more than one occasion, a woman has asked me if I wanted to do "butt stuff" when it became clear that coitus wasn't cutting it anymore. Assplay is a logical next step in a male/female sexual relationship. It's taboo; it's still kind of like standard heterosexual fucking since it's also about putting something inside a hole and most importantly, the difficulty level is high. Quality, efficient buttsex comes around about as often as the Aurora Borealis or a black Mormon.


Sometimes, when all hope seems to be lost and the world is shrouded in darkness, my female sexual partner will ask to give rather than receive. I am the sort of person who assumes that each girlfriend I have will be my last, so I do everything in my power to ensure that I don't get dumped. I do laundry more frequently. I start cooking dinner. I forgo watching sporting events. I floss. I seriously consider putting things in my ass.

"Butt stuff" takes many forms. Some maneuvers are more elaborate than others. All require a man far more coordinated than me to perform them successfully.


The first time I had a finger in my ass was the last time I called 911 after having sex. No one is supposed to have a panic attack when making love, yet as soon as I felt a knuckle grazing my taint, I started to seize up. I survived, but my girlfriend's finger did not come back from the journey unscathed. In order to better cope with assplay, I've taken to saying the alphabet backwards as a means of relaxation.

Ass Licking

Ass licking is relatively unobtrusive, in that it does not include penetration. At the same time, it's not actually that exciting. Anilingus is the cotton candy of assplay. It's a novelty that's fun once. In the autobiography of my asshole, titled What About My Sphincter? the chapter on ass licking will be the shortest, but also the one with the most illustrations.

Random Object Insertion


Any household object can become a sex toy. A TV remote control, a broomstick, a rolled up New Yorker magazine, a signed home run ball from Barry Bonds or a gerbil can hypothetically be inserted into an asshole. The pleasure here doesn't necessarily come from the actual act of shoving something up your ass. It is derived from realizing that you are clever enough to figure out how to get these myriad objects inside such a snug, small hole. This activity stimulates the same area of the brain that responds to crossword puzzles, Rubik's cubes, Sudoku, and assembling IKEA furniture.


If you know what pegging is, you've probably pegged or been pegged before. In this scenario, a woman fucks a man with a strap-on dildo. Rumor has it that pegging can be physically pleasurable for the woman due to the stimulation of the clitoris by the base of the dildo. I classify this as a rumor because no woman has ever admitted to me that this is true. Ladies, until you prove it to me in person, I just won't believe it.

Watching Another Guy Fuck Me in the Ass

If you have gotten to this stage with your girlfriend, it means you are too far gone to ever be happy again. You are only a step away from fucking a corpse at the scene of a car accident. Adding another person to a sexual fantasy is an admission that boredom has set in. Adding another person of the same sex means the new participant in the equation must look as different from your significant other as possible. Adding voyeurism on top of all that means you'd absolutely rather be watching porn than joining genitals with your partner.

For the record, I said no to this request from my girlfriend. A few weeks later, she dumped me, claiming that she felt a "distance between us." I'm sure the distance would have been much less had I agreed to allow her to watch me get fucked by someone else.

Let this be a lesson to you. Relationships are about doing things you don't want to do. Sometimes that means taking out the trash. It could also mean barebacking with a 43-year-old man named Clarence.

Photos by Travis McFarland.