Masquerading as a Masculine Bottom

Artwork by Anthony Gonzales – IG: @anthgonz1

Dear Walter,

I’m obsessed with straight-acting, typically DL men. I know you recently wrote that dating a DL dude wasn’t a good idea.  But I want what I want. So the other day I was on Grindr, and the guy in question was looking for a masculine bottom. I’m like what’s that. And how do I become that?

I like it missionary, kissing, and pretending I’m the girl. I know it may sound crazy but I find “homo thugs” so enticing. They are definitely my type. And as someone who dresses more like a queen. It’s kind of a fantasy of mine to meet someone DL, maybe married or have a girlfriend. Don’t judge, I’m not really a homewrecker. But this thirst needs to be quenched.

Any advice would be nice.

Thanks again,

Need a DL Dude Today

Dear Need a DL Dude Today,

I’m not naturally the masculine person. And I suspect the one asking for a masculine bottom is probably not the most masculine either. But I digress and let’s dig in. Once, I went deep undercover to experience what it’s like fucking as a masculine bottom. I searched on Adam4Adam like I was looking for someone to pay my bills. And with the inauguration upon us, I lusted for someone to stuff my ballot box.

We exchanged 60 messages punctuating photos and preferences. Photos of 9.5-inch penis titillated me. His dick looked like a Snickers candy bar, veiny and chocolatey. But was I ready for it melt in my mouth?

John craved a hairy masculine bottom in his profile. I had no plans to sprout any hair. But on the bright side, I didn’t have to shave my pubes back there. He had a predilection for dominating masculine men in compromising positions.

He had two rules to smoke and fuck. I agreed to follow them both.

I selected my clothes carefully:  black and mild. I took two ibuprofen before calling him. My iPhone has been acting up all week, which is code for I haven’t paid the bill with no plans to pay anytime soon.

I like to first enter a potential suitor’s phone number through Facebook to see if he had an account. (That’s a cute tip to take the catfish out some online experiences.) But he didn’t.

“Yo, what’s up,” I said with as much bravado as possible as he dispensed directions. I stopped by the liquor store to pick up a personal bottle of vodka. It was more like a vile. I took a shot while Ariana Grande cooed, “I’m so into you I can hardly breathe,” in my ear.

Neighbors spotted me, I didn’t know if they noticed a shift. An older black guy in loose sweats smiled and inquired where I was going.

“I’m going to meet someone,” I said as he walked in the other direction.

Navigating the streets of SE, DC where six lights didn’t quite equate to six blocks. I shifted my leather bag across my shoulders as I got closer. I had to check my computer for his address. Five more doors. I ranged the bell as butterflies entered my belly.

He opened the door, donning a fitted cap, black pants, and a t-shirt.

“Take your shoes off, and let me give you some water so you can cool down.”

“Yes, please,” I said as I settled on the black leather bar stool that set in front of the kitchen.

I found myself very attracted to him, although I towered over him a bit. He poured us vodka cocktails. I love day-drinking. He offered a bong for me to try, which he called Cookie.

“Well, Cookie’s got to eat,” I said.

Cookie looked like a giant glass dick. I walked around the counter in a black tank. I don’t know if my masculine facade is fading.

But I began to relax as the smoke filled my lungs, overwhelming me, to the point of coughing. After the bong, we transitioned to a blunt. He pulled out a silver apparatus that encapsulated the blunt.

I was high as hell on MLK day, my vision filtered through a tint as if I were wearing shades. I enjoyed the sleek leather furniture, marble countertops, and dark cabinets that wrapped around the kitchen.

“Is that pussy wet?”

I’m sure masculine guys don’t talk like that to each other.

“Um, sure,” I said.

“Grab your drink,” he said while walking passed the artwork that lined the walls next to the stairs. We passed two bedrooms to get to the third one, in the back where a red-lighted room awaited. I stood in front of the big, burgundy bed surrounded by dark furniture.

“Put that drink anywhere, it’s a man’s house.”

I placed it near a closed laptop on a fold up table. “Come right here, and take off your clothes, and lay on your stomach,” He said while stripped off layers revealing a throbbing dick.

It was much thicker in person. He was ready to plop it in. No foreplay, unless you count cocktails and conversation. No kissing. Is this how masculine men have sex?

“Where’s your condom?”

He flashed a gold foil Magnum wrapper at me. He sprayed some lube on my hole and guided his dick in.

“Be gentle,” I demanded.

“I got you. Open that pussy up for daddy.”

He oiled me like an oil slick. I was so greasy I was ready to slip off the bed. He pulled his dick out and maneuvered his fingers. He started with one, then two and deeper he went. My ass began to sweat. He massaged my soul with his fingers.

“Every time I pound it, squeeze your hole.”

I received his dick, flooding my guts with his meat. Back-and-forth, back-and-forth. I felt amazing.

“Now, I want you on your back.”

I held my legs as high as I could. I needed a yoga class pronto. My legs shivered as he entered me again.

“Damn, it’s getting wet again. I can feel your third hole.”

He slammed me like a mistress in the middle of the day. I stared at the projection of the solar system on the ceiling.

This was too choreographed.

“Follow me,” he said while motioning me. We traveled down two flights of stairs to the basement. I walked into a den of iniquity, where a leather swing awaited. He pushed me on the swing and grabbed one of my legs to strap in.

“Wait, is this being recorded?”

“No, there’s not enough light to record down here,” he said. I began panting, reaching the top of the swing to see if a camera was present.

I freaked out because there’s a guy in my neighborhood that records homemade hardcore porn. Guys getting fucked raw by his 13-inch dick. Not today Satan!

“Let’s get back upstairs, and grab you some water,” he said as he held my hands.

“I didn’t mean to freak you out. But that sex dungeon freaked me the fuck out.”

“It’s James right?”

“Yes, it is.”

I stood naked in his kitchen and surveyed the cabinets and marble countertops and I cooled down. Okay. I’m in the same place.

“Let’s go upstairs and begin again.”

“In order for you to submit. I need you to trust me.”

Granted, I have trust issues. But we just met. So we returned to the bedroom.

John laid down in the center of the bed like the letter “A”. I sucked his dick on all fours while my ass arched to the sky like a dog. Wet and slow as he preferred it. His dick felt meaty and massive. And with practice sliding up and down his shaft I began to deepthroat it.

Damn, I’m getting better at this. He was ready to go again. He fucked me for two hours. And we kissed.

“I can tell you’re going to fall in love with me,” he said after I came on my inner thigh while he still inside of me. He replaced his dick with his fingers as the sperm oozed out, causing my hole to tighten up.

“That was your fourth hole,” he said. “I’m going to train this ass. You’re going to get you a husband. And you’ll be here every week for lessons.”

I wasn’t sure about how many holes or the husband. But what I experienced — I needed again. I got dressed and walked toward the door. “ You bet not walk out my house like you got fucked.”

I laughed and adjusted my walk. I arrived home hazy and slept for 12 hours. I awoke the next day thinking damn that was some good dick. But he never ejaculated.

Oh well, I guess that’s what having sex as a masculine bottom is like.

I realized that altering my personality and mannerisms at the moment didn’t provide the most satisfying results. I mostly found the experience to be exhausting.

I hope you don’t lose yourself just to satisfy a stereotype.

Love,

Walter

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