I Stuck a Finger Up My Boyfriend’s Ass

Willow Gray @_willowgray (6)

Jacob does not talk about sex. He’s good at it, though, so I encourage him to talk about it with me. But he’s always had a much more reserved relationship with sex, although he openly loves his penis. I, unbothered by his modesty, spoke about sex — my sex, our sex, sexual health, sex in politics, sex in the news, sex on planes — freely and oftentimes loudly and at inappropriate times. Jacob would never dissuade me from screaming from the rooftops about intimacy. Rather, my boyfriend had a tendency to broach the subject in the liminal spaces of our lives. 

Brushing our teeth. Tuesday evening. 10PM. “Baby, why do you prefer having a threeway with two girls and not two guys if you consider yourself to be straight?”

Waiting at the gas pump. Sunday before family brunch. 8AM. “Angel, do you think it would feel good if I used the vibrator on the little space between my balls and my asshole?”

CTA Red Line, Jarvis stop. Heading to get Ethopian food. 5:13PM. “What were you saying about using food in sex when you were on the phone with Phoebe last night? Frozen grapes sound fun.”

Aside from these rare, random occurrences, Jacob was otherwise silent — which I mistook for vanilla. And after this particular rendezvous, I must argue his sexual appetite is much more fluid than I’d previously given him credit for. By which I mean, I was not expecting it when he asked me to stick my finger up his butt.

Now, in my defense, I hadn’t ever had anyone ask for a finger up there. And I’d been around. So when Jacob, my 6 foot 2 inches ex-football player, “manly-man” boyfriend asked me if I’d ever touched someone’s ass before, my immediate response was almost: have you?

Instead, I asked him what he wanted me to do. Partially out of curiosity but mostly out of ignorance. If he wanted me to touch him, he was going to have to show me exactly what he meant. He got nervous upon being asked to explain. After a lot of “uhs” and “umms” I finally got a rhythm down, gently pressing the tip of my pointer finger against his hole, pushing slightly further in when he motioned for me to. He would nod with what he liked, and adjust my hand when he didn’t like what my finger was doing. His dick was in my face, so I started giving him head at the same time (Something I actually know how to do!) .

The whole thing lasted about eight minutes before we got to the good stuff (can anyone say, intercourse!). Afterwards, once we had rehydrated and gotten our morning coffee, I asked Jacob what compelled him to ask for such an act. To which he responded that I should relax and be more open. Again, I was stunned. 

“You were nervous,” I told him. “The way you asked made it seem like it took effort.”

“It did take effort,” he shrugged. “You know — imma dude. That type of shit…” he trailed off. 

“Baby, I don’t know!” Jacob grabbed me by my waist and pulled me into him. Normally, I was the one who pushed for experimentation in the bedroom. 

I introduced him to the vibrator and the handcuffs. Whipped cream and frozen grapes were also all me. Our only collective effort had been roleplay, which I attributed to all the ridiculous storylines in shitty mainstream porn. So, having him tell me to broaden my horizons was an unexpected shock to the system. 

He laughed when I said nothing. “I know you always like for us to try new things with your body, I figured we could do the same with mine.”

Incrédulous, I asked if I had done a good job. 

He answered in the affirmative. But told me to be more sure of myself. “I want you to touch me,” he said. “That always feels good to me.”

Mentally taking notes, I asked if he’d ever had anyone do that before. 

Affirmative again. What? I thought. This man had been holding out on me. “Jacob!” I slapped his arm. “Why are you just now telling me?” 

“Because it’s embarrassing!”

“I literally write about sex for a living!”

“Being a man makes it hard to ask!”

“It shouldn’t.”

“But it does.”

“What made you ask if you were so nervous?”

“You literally write about sex for a living.”

I burst into a fit of giggles, “You just don’t want me to think you’re gay!”

He pinched my sides, making me laugh again. “You know I’m not gay.” He pinched me again. “And so what if I am? I still like fucking you.”

And, he was right. On several fronts. Firstly, I did know his preferences. Secondly, so what? A quick Google search will reveal how the prostate is, in many ways, the male “G” spot, rendering stimulation not only natural — but encouraged.  I laughed to myself. I should know better than to relegate male assplay solely to the sex lives of gay men, I couldn’t avoid my automatic bias towards butt-stuff. 

He paused as I re-situated myself on the bed across from him. “You’re always talking about sex,” he said slowly. “You’re explicit, but you’re precise. It’s almost clinical.”

I swatted at him. He dodged me, “Hey! It’s not a criticism. I’m just saying, you tell me what you like.”

“I do,” I agreed.

“And you’re so direct that it’s impossible for me to misunderstand you.”

“That’s why our sex is good,” I said.

“That is why our sex is good,” Jacob agreed. “But it could be better.”

“For you,” I stated.

“Exactly,” he agreed again, grabbing my feet and pulling me towards him. “But for that to happen I have to communicate.”

“I fucking love communication,” I lamented into his shoulder, biting him gently, for emphasis

“So yeah,” he said, pulling me up and pushing me towards the bathroom. “I had to tell you that I like fingers up my ass.”

“And I know you’ve lacked interest in reciprocation” he said, turning on the shower for me.  “But let me know if you change your mind. Pretty sure I have a butt plug somewhere around here.”

Still partially catatonic from the narrative switch between Jacob and myself, I hardly had time to process his first comment before he left me with more.

“Maybe once we get married I’ll let you peg me,” Jacob said, pulling closed the glass shower door, then leaving me to marinate in my shock in private.

So… yeah. That’s what happened. That’s how my finger ended up in my boyfriend’s butt. And, uh, it’s most definitely going to happen again. I hope my mom never reads this. 


Photo (in order of appearance) by Willow Gray and STAA Collective