How I Finally Convinced My Man To Enjoy A Finger Up His Butt

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woman finger

"Baaaaabe, stop it!" my boyfriend, Quaint, shrieked, jumping forward in the grocery aisle.

Poking his ass was my equivalent to him snapping my bra. I was eighteen. Quaint and I had dated nearly two years. In our relationship, I progressed from lying stiffly on my back, struggling to keep every article of clothing on through intercourse to a full-on sex participant. Sometimes, I even dared to walk across the room bare-assed with the lights on. We ventured into every position, location, and bodily region.

But anal was my least favorite bedroom activity. The whole charade felt like pooping backwards. It was something I begrudgingly did in exchange for backrubs and switching the television from football to Sex and the City.

It was common knowledge that men love shoving their dicks in buttholesHowever, the male assh*le was treated as if a grenade was lodged inside, igniting a deadly explosion of anger, trauma, and sexual confusion.

I entered my promiscuous twenties. I cycled through a slew of partners. I went through the gamut of threesomes, slapping, hair pulling, choking, and blindfolding. I occasionally allowed back door access when I was feeling generous. Regardless of how many envelopes pushed, the prostate remained mythological.

"Hey, beautiful," my new Tinder matched typed. "You own a strap-on?"

The dating app was a dangerous addition to my iPhone. I could sit in traffic and carelessly swipe my way to dick-on-delivery. Tinder made hookups as convenient as picking up lunch. Out of pure shock, I immediately unmatched him and shook him off as a cliché Internet weirdo.


"Any man who wants you to f*ck him up the ass is gay or at least bisexual," the bartender smirked as he shook and poured my Lemondrop martini before sashaying to a burly, bearded patron in a tight tank top.

I was living in Atlanta, finishing my book, waiting tables, and saving up for my move to Seattle. I worked in the core of the LGBT community. Our staff was predominantly gay men freshly emancipated from their homophobic hometowns. None of them were ever told them to keep their legs closed and string a man along. But the more I learned, the more I realized that their mating culture was even more rigidly categorized than mine.

Grindr, the gay version of Tinder, requires men to list their age, height, weight, race and body type. Depending on their age, height, build, tattoos, body hair, and wardrobe, they are twinks, cubs, otters, bears, wolves, gorillas, and so on. In the bedroom, they are tops or bottoms. Although there were "versatile" gays who did both, the top and bottom often created gender-like roles. The stereotypical bottom was the woman; effeminate, submissive, and physically smaller, while the top was dominant and masculine.

Tops took pride in being the Alpha while the bottoms were lightly mocked as flamboyant fairies who doused their hairless bodies with glitter and pranced to the sound of Beyoncé and Lady Gaga. Spotting tops or bottoms was a guessing game based on their level of masculinity.

Whenever one of our coworker's hands got too flappy or strut too jazzy, we'd call them "power bottoms." I was oblivious to the fact that we were judging men for getting penetrated.

At the twilight of another Tinder date, I wound up slightly drunk and on my knees. My match's balls were in my mouth, then my tongue behind his balls, and then somehow he'd scooted upward and my tongue had crept into that unmentionable cave. Oddly enough, I dug deeper. He squirmed and moaned into this spasm of euphoria that I hadn't even seen in a man in the middle of climax.

Within minutes, he was sitting in a puddle of his unborn babies.

"Aw, straight boys are finally discovering their prostates," my gay friend, Rowland said. "How cute. The prostate is one of a man's primary G-spots. That's why gay men love anal but women usually don't."

I always assumed that anal sex was a homosexual thing because of the absence of the vagina. But I thought about my date's reaction to my tongue against his prostate as if I'd just shot ecstasy through his bloodstream.

As if they sensed my backdoor pioneering experience, men began dropping hints. They'd rim me and then scoot their behinds onto my face. But penetration was a big deal. They protected their anuses the way girls protected their hymen in high school, believing that allowing anything beyond their holy gates would permanently corrupt them.

It only takes a basic course on evolution to know that the prostate G-spot's existence alone is proof that ass play has been done for a very long time. The prostate's purpose is to produce secretions that feed sperm cells. It also provides muscular contractions that lead to ejaculation.


I expected a healthy dating life in progressive Seattle but I found myself fighting my usual battle between my sexuality and distaste for the accompanying shallowness. We long for an intimate connection, but that longing makes us feel vulnerable. Therefore, we guard our hearts for self-preservation, which barricades intimacy.

Casual sex is a very sad cat and mouse game. The man is entrapped in his role as the sex-driven predator, while the woman is the prey that must find her perfect combination of allure and virtue.

Time and time again, I saw the change men's eyes once they had me. Dehumanization always follows penetration.

I'd eaten halfway through my savings by the time I reached Seattle. In the height of my anxiety, a friend swayed me to go out. We wandered to a restaurant bar downtown where I struck up conversation with a bartender.

"You know, we're looking for a server," he mentioned. I thought I'd struck gold when he told me to come in the next day to meet his manager. "Just push up those tits," he advised.

The bar manager was a 38-year-old single father with a not fat, not thin, but a lackadaisical, soft dad bod. Dadbod was witty. As I sat at his bar and watched his eyes scan my body, I knew we'd never be friends. I played his game. I laughed at his jokes and leaned forward in a manner that would accentuate my breasts. I needed a job and didn't have the luxury of giving a f*ck about anything else.

"Come in tomorrow," he told me. "Work a shift and we'll see if you're a good fit."

At work, I flirted. I shrugged off his lingering hands brushing my hips and his palm grazing my ass. Dadbod drained the liquor stash, shoving me samples of every cocktail he could concoct. I sipped on them and passed them along when he wasn't looking. I faked intoxication in hopes that he would eventually employ me.

Dadbod oozed inappropriateness so heavily that I became accustomed to it. It didn't even occur that his suggestion to "follow him home to cover his expired tags" was an obvious attempt to lure me to his bedroom.

"You can either go home or come in and cuddle," he said. I couldn't tell if his offer was a job requirement or sabotage.

I wasn't even slightly sexually attracted to Dadbod. With him, my vagina was a bear being awakened from hibernation, annoyed by shakes and stirs. Intuition told me not to give Dadbod any pleasure. But the time inevitably came where I had to give him something to put him to sleep and end our whole charade. Dadbod needed milking.

"Do you have any coconut oil?" I asked. Dadbod returned from the kitchen with a half-gallon tub. I envisioned him using it to cook his son pancakes the next day. If I was going to make him cum, it was going to be in a way so humiliating that he would never tell a soul about it.

I oiled up my hands and shoved two fingers up his rectum and performed the procedure. I barely had to touch his penis before it exploded, quivered, and fell asleep in a fetal position with the rest of him. 

I got the job.