The Best That Money Can Bi

Contains male-on-male sex.

*****

A frustrating and fruitless weekend had gone by. Ad after ad went unanswered or spawned endless back-and-forth. It was late Sunday night and I had that desperate itch that only group action could scratch. I hit refresh, ready to call it a night. A new ad appeared: "Young couple for gen guy." Okay, so they're selling it, I thought. But let's take a look anyway.

Their ad contained several G-rated photos, some individual, some together, each of them blurred or cropped. But they seemed to be what they promised; an in-shape young couple looking for a "generous" guy. I replied, and after several exchanges peppered with lols, idks, and other millennial acronyms, I learned that their names were Mat and Joanna, they were 23 and 22, and based on their latest photo, very good-looking. Mat had a mop of wavy, sandy hair atop a lean, angular face with high cheekbones - a pretty boy. Joanna had long, waist-length chestnut hair framing a soft face with deep, shadowed blue eyes, and full, painted lips - a vampy girl-next-door. Mat stipulated that they weren't into anything "hardcore". I asked what he meant. "idk ... lol ... nothing crazy ... just want kissing and oral and stuff." Better than nothing, I thought, and agreed to both their condition and their price. Mat's final message was simply an address.

I downed my bourbon, stepped into the chill night, and hailed a taxi. The address was ten minutes uptown, in a less salubrious neighborhood. Alighting from the cab, it took a moment to find the street number; a modest building with a glass door looking down a common hall of adjoining apartments. I pressed the #2 button on the intercom and a muffled, distorted voice responded. "Hello?"

"Hey, it's Justin."

"Oh, hey!" a cheery voice replied. "Gimme one sec."

I waited, peering through the glass down the hallway. A man's head emerged from a door to the right, grinned, and disappeared.

"Okay, cool," from the intercom. "Come on down!" Then a buzz. I opened the door and was met in the hall by Mat. He was a little shorter than me, perhaps five six, and skinny. But very cute. He was dressed unseasonably; barefoot, in pale jeans and a linen shirt with loose buttons, hinting at a smooth chest. He looked like he had just thrown them on. He seemed friendly, but a little nervous. "Mat," he introduced himself.

"Justin," I replied and shook his hand.

"Come on in. Sorry, the place isn't that big ..."

I stepped into their studio apartment. A living area directly in front of me, a kitchen space was to the left. Beyond that was a queen-sized bed covered by a single fitted sheet. The modest apartment was lit by several colors of fairy lights - obviously a remnant from the holiday - and a dim bedside lamp. We were met by Joanna, who took my coat. Like Mat, she resembled her picture, but had perhaps put on a little weight since, which I appreciated. She wore a dark skirt, blouse, and pantyhose - no shoes - and looked like she had just gotten home from work. Joanna, too, was friendly, but there seemed to be a sadness behind her smile in contrast to Mat's cheerfulness.

"Hi, I'm Joanna," she said, and I shook her hand also.

Small talk ensued. Top of my list was why this nice young couple was doing this. They needed help to pay the rent. Mat was at school and Joanna worked in retail, both in the fashion sphere. Mat had always been bisexual and Joanna was cool with that, or so she said. They seemed to think nothing of their prostitution. They had a regular guy, but he was "like, old" and out-of-shape, married and had kids - and he had stopped seeing them. "So much nicer to have a cute, young guy," said Joanna, running a finger down my chest.

"How old do you think I am?" I asked wryly.

"I dunno ... late twenties?" she replied.

"Ha. You're sweet," I said, letting her guess go wanting.

We made our way to the bed and had sat down. I kicked off my shoes and perched on one corner of the mattress. "How do you want to get started?" Mat asked.

"Not sure," I responded. "How about you two start making out and I'll watch?"

"Okay!"

The couple knelt on the bed, facing each other. They embraced, their mouths locking in a kiss. Hands clawed at clothing. Joanna's blouse fell first revealing a lacy black bra sitting on pale shoulders. Mat's shirt was next, then Joanna's skirt. Then Mat's jeans, and he was now completely naked. I admired his body in the dim light. He was smooth, lean, and toned. Even only semi-hard, I could tell that his cock was impressive; perhaps nine inches and uncut. Large, smooth balls hung beneath a thick shaft that Joanna gently massaged. Mat unhooked her bra, revealing pretty, C-cup breasts with large pink nipples, one of which he took in his mouth.

Aroused, I moved towards them, placing a hand on each of their naked backs. The couple disengaged and turned towards me. Mat's fingers hooked under my sweater and raising my arms, I let him pull it off. Joanna deftly unfastened my belt and zipper, and then her hand was inside my jeans, finding my own hard cock. Mat leaned in to kiss me. I don't normally enjoy kissing men, but he was just so damn pretty, and I went for it. Our tongues mingled in each other's mouths, our stubble scraped each other's chins, and our hands explored the other man's body.

I felt Joanna's warm, moist mouth engulf the head of my now full erection. I pushed away from Mat and reclined on the bed with a sigh. Joanna's long hair pooled around my stomach and thighs and her lips glided up and down my shaft, each downward movement taking me a little deeper. Mat rose from the bed and straddled my face, lowering his weighty sac to my willing lips. Taking one of his smooth balls in my mouth, I sucked on it, circling my tongue around it. Then I took the other. Together they were too big for me to take both. I could feel Mat stroking his cock, his upward motion pulling his sac away from me just as I tried to suck it in.

Reluctantly, Mat pulled away from me before lowering the tip of his cock to my lips. My mouth eagerly welcomed him, savoring his salty pre-cum on my tongue. I craned my neck over the edge of the mattress to give him better access. Oh, yes, this is what I craved.

The head of Mat's thick cock almost filled my mouth. My lips formed a seal where the head meets the shaft, and I held him in my mouth while my tongue teased his string. Then I felt his hips twitch as he began to ease his girth further into my throat. I desperately wanted to take each of his nine inches, but I couldn't. He was just too big. But he made the best of my efforts, gently fucking my mouth with subtle thrusts, withdrawing once or twice to slap my face with his meaty dick - porno-style. "That okay?" he asked.

"Fuck, yeah."

The three of us disengaged. I pushed my jeans off my thighs and we knelt facing each other on the bed; the men naked, Joanna still in her hose. I leaned in to kiss Joanna, tasting my familiar flavor on her tongue as she no doubt tasted Mat's. My hands found her soft breasts and my palms glided over her nipples before my lips did, taking a firm bud between my teeth and squeezing lightly. She shivered and let out a little gasp. Mat's hand glided down my back and beneath my butt, before a moistened digit found my asshole.

I stopped and turned my head. "I thought you said you weren't into hardcore?" I said.

"Yeah ... I ... just need to fuck you," Mat replied softly.

"Okay, then do it," I said, leaning forward so that I was on my elbows and knees, presenting my ass to this other man. I glanced down my torso to my cock hanging between my thighs, still slick from Joanna's mouth. I heard the sound of a wrapper opening and, behind my own, I could see Mat's sac jiggle as he rolled the condom on. He spat on my exposed hole. I smiled. Defintiely porno. Then he worked his wet finger into me again. I love assplay, but knew this was the pleasurable part before some pain would follow. Soon I felt the cold wetness of lubricant pool on my cleft, then drip down to my anus, where Mat's finger was already knuckle-deep. His finger slid out and, heavily lubricated, and this time slid in all the way. It was shortly joined by a second, which crossed the threshold between pleasure and intensity.

Mat finger-fucked me hard and vigorously, his palm audibly slapping my ass with each thrust. I knelt there, clenching my teeth, taking it. He stopped and pulled his fingers from my raw asshole. More lube was applied, and then I felt the tip of his thick cock press against me. He pushed his hips forward and the pressure built until his glans penetrated my dilated asshole.

"Oh ... fuuuck!" I cried, sucking in my breath. I felt like I was being split in two. Yes, physically, I was in pain, but mentally, I felt so deliciously dirty.

Joanna had moved to the edge of the bed. She had peeled off her panties and hose, and now she too was naked. Back propped against a wall she sat there, watching us, legs spread. Two of her fingers dipped in and out of a slick cunt fringed by a wisp of dark hair. "So hot," she whispered under her breath.

Breathing heavily, I began to accommodate the intense pressure filling my asshole. Mat pushed further, a half inch at a time, and I bunched the bedsheet in tight fists.

"You gotta stop there," I cried in a whisper. "No further."

"Okay," Mat replied. "Don't worry. I get that a lot." He began to rock his shaft back and forth inside my ass, but never further than the five or six inches he had penetrated. The sensation was exquisite, but almost unbearable, and all I could do was squeeze my eyes shut and my fists tight.

Mat's controlled movements became more rapid, his breathing faster and harder, then he abruptly withdrew. I heard the snap of a condom come off, some vigorous stroking, and a deep groan as Mat exploded on my back, his cum forming a sticky, warm line from the small of my back to my shoulders.

"Nice, baby!" Joanna to one side, her fingers still sliding in and out of her cunt.

I slowly raised my elbows off the bed. Mat's seed dripped between my buttocks, briefly soothing my burning hole, which had to be red and raw. "Fuuck," I whispered, barely audibly.

My cock had remained hard as it always did during anal sex, and jutted out from my abdomen. Spying it, Joanna shifted to her knees and scooched towards me. Taking my shaft in her hand, she once again lowered her mouth to the tip. No gentle sucking this time, though. This time, she worked it; fingers and mouth working against each other. Mat moved next to her. Gently taking my cock from her, he took it in his own mouth, sucking me in a way that men like to be sucked. He released me, and then both their mouths were on my shaft, sucking and licking, as their hands caressed my thighs, balls, and ass.

Mat once again took over with his expert technique, Joanna watching intently inches away. She looked up at me with those shadowed eyes. "Cum for us, Justin," she begged.

My breathing became more rapid and Mat seemed to know exactly when I was going to orgasm. He pulled his lips from my cock and with a few more strokes, I came with a loud moan, spattering a stream of milky fluid over his cheek, eyelashes, and forehead. He pushed my cock in front of Joanna's face and, with a few more flicks, a second, smaller white trail shot over Joanna's cheek and lips. "Oh, yesss!" I whispered, before collapsing back on the mattress.

We caught our respective breaths for a moment before I rose from the bed and dressed. "Two hundred, right?" I said, taking the cash from my wallet.

"Yeah, that's right." Mat rose as well, pulling on his jeans, but remaining shirtless. Joanna pulled a comforter from the floor and wrapped herself in it. I left the cash on the kitchen bench as Mat showed me to the door.

"Nice to meet you, Justin!" Joanna from the bed.

"A pleasure doing business," I replied as I slipped on my coat. I left the apartment and the building, stepping once more into the chilly night to hail a cab.