Never Had I Ever

Never had I ever

"Never have I ever sucked a dick."

It was the type of declaration that can turn a friendly round of Never Have I Ever into something much more contentious.

The Cuervo had stripped me of any sort of diplomacy. It'd had an impact on Emily and Deneisha too. Without hesitation they each dropped a finger and a sly comment about me being an asshole.

The night had started as a little gathering of some of me and Deneisha's co-workers but had eventually devolved into the three of us playing Kings Cup in the living room and ripping shots of tequila.

I reached for the bottle and poured us all another round. We each grabbed a lime from the cutting board on the coffee table and threw it back.

"Where were we?" I asked through a grimace.

"You just made a big mistake and are about to get embarrassed."

Emily grinned devilishly and put her two fingers up. Her current attire was exactly the reason why you sign up to have girl roommates. Once the last guest left she'd extracted her bra without removing her white tank top and gave her tits a good shake. Now she sat across from me, auburn hair pulled up into a bun and a pair of boy shorts that showed off her tanned thighs. I could also see her nipples through her shirt and she knew it.

"Clearly you didn't do the math," Deneisha chimed in from next to me on the couch. She didn't live with us but she and Emily had grown to be fairly close so she became our de facto third roommate on nights featuring heavy drinking. I didn't mind. She had a big smile and an even bigger ass.

"I like my chances," I said.

"Alright, hotshot," Emily interrupted. "Never have I ever licked a vagina."

I dropped a finger and took a sip of my Corona.

"That's what I thought."

"Let's see..." Deneisha tapped her two fingers against her caramel cheek in thought. The nails were long and pink and immaculate. "Never have I ever done anal."

I dropped another finger.

So did Emily.

"Em! You whore!" Deneisha cackled.

"What can I say, my ex got me hooked."

"Ya?"

"Oh yah. There's nothing like it."

"Does it hurt?"

"Not really. Maybe a little at first. Lube is your friend."

"Oh my god! That's crazy. How about you, Max?"

"Yeah, I guess a little at first," I said without making eye contact with either of them.

"Wait a minute," Emily shrieked.

"What?" Deneisha asked.

Emily stared at me, her grin somehow growing larger and larger. I shifted uncomfortably in my seat and held my finger up to signify the game should continue. Emily disagreed.

"Have you been fucked in the ass?"

The tequila could do nothing to mask my embarrassment. Out of reflex, I took a long sip of my beer.

"No fucking way," Deneisha said.

"Was it a.... Dude?" Emily asked hesitantly.

"Fuck no."

"Well... who was it?"

"You gotta tell us."

"I don't gotta tell you anything."

"Oh come on, we're not going to tell anyone. Besides, if you really didn't want to tell us you would've just lied and kept your finger up." Emily may have had a point there.

"It was a few months ago. This random chick I met at MacDinton's."

"And she just took you home and fucked you."

"Well, it didn't start that way. I was fucking her but mid-bone she stops me and says she has to go to the bathroom. I don't think anything of it, I was really pounding her. But then she comes out wearing this lace thong thing and a dildo hanging between her legs."

"And that's all it took."

"I was fucking wasted. I barely remember any of it and I probably would've forgotten all about it if she wasn't still wearing it the next morning."

"Oh my god," Emily said through a stifled laugh.

"How big was it?" Deneisha asked.

"Hell if I know."

"Bullshit."

"Bigger than yours?"

"Probably the same."

"That's not helpful. How big is yours?"

"Seven inches, give or take."

"Ohhhh." They both said in unison like the story suddenly made all of the sense in the world.

"That's pretty big for a first-timer," Emily added.

"Yeah, well, the morning was easier."

"The morning?!?" They yelled in tandem.

"She fucked you again?" Emily asked. She was leaning forward in her seat with her elbows on her knees, her boobs dangling against the tank.

"I was too drunk to cum the night before," I tried to explain. "She insisted I hadn't gotten the full experience."

"And?"

"And she gave me the full experience."

"Oh my god!! You came?"

"Twice."

"Wow."

"I guess I'm the one really missing out," Deneisha said with a smile.

"You know," I began hesitantly. The tequila was taking the lead now. "You don't have to."

"Is that so?"

Deneisha leered at me. She glanced down and my eyes followed. The outline of my cock pressed against the fabric of my basketball shorts like it had somewhere to be.

"You don't think you'll hurt me?" She reached out and pressed her thumb and forefinger around the edges of my dick before lightly pinching them together like a gauge.

"Lube is our friend," I grasped onto her thigh and ran my hand up her jeans until I had a firm grip on the side of her ass.

"Fuck this is hot," Emily said. "I hope you fuckers know I'm not going anywhere."

"I don't mind." I was still looking at Deneisha.

"You can be my coach."

Deneisha stood up and my hand stayed glued to her. The pronounced curves of her body seemed cartoonish. Her thick thighs and firm ass giving way to a slender midriff that lay exposed. Her tits weren't huge but did their part to complete the S. I gave her ass a firm shake that she didn't hate.

"You two need to come with me now."

Emily grabbed Deneisha's hand who in turn grabbed mine. We were led away like a chain gang to Emily's room with no dialogue. Once in, Deneisha stopped at the foot of the bed and with her back to me, began unfastening her jeans. She wiggled her bottom as she struggled to peel them off. Once they eclipsed her hips her ass--framed by a red thong and flawless like a Godiva chocolate--reverberated before resting firmly in place. Next, she hooked a thumb into her panties and pulled them to the floor without bending her knees. She stepped out and faced me. She had no tan lines and a thin wisp of a landing strip.

"Your turn."

My undress was hardly as sensual. As I peeled my shirt over my head, Emily had latched onto my waistband and pulled down my shorts causing my cock to jump and bounce to full attention.

"Oh, alright," Deneisha took me in her hand and stroked it softly. "How do you want me?"

"Doggystyle, I guess," I said tentatively.

"My favorite."

She turned and climbed onto the bed with the sultriness of a leopard. Her tight t-shirt rose slightly up her body exposing part of an elaborate tattoo tracing along her rib cage. Once in position at the edge of the bed, she looked back at me over her shoulder. I felt a set of hands running across my dick and realized it was Emily smearing KY all along me but focusing heavily on the tip. I shuddered at her touch.

"Easy, tiger," she whispered before approaching Deneisha. She squeezed a handsome amount of lube onto her ass.

"Ugh, I wish I had your ass," Emily said before planting a playful smack against it. Deneisha gave it a shake.

Emily ran her finger down the length of her ass crack and began circling her asshole. After a moment and a little more lube, she stepped back and grabbed me by the cock, pulling me towards Deneisha. Emily was to be the facilitator--at least initially. After all, this dynamic was technically uncharted territory for me so with my hands free, I grabbed onto Deneisha's ass firmly. The tip of my cock pressed against her and slowly Emily worked me in, stopping and occasionally massaging Deneisha's asshole with her thumb. All the while Deneisha's breathing and moans became more pronounced.

"How's that feel, Deneish?" Emily asked.

"Amazing. But I want that cock."

She buried her head into the mattress and waited for her demand to be met. It was my pleasure.

I eased against her puckered asshole and felt it give way. Deneisha let out a shriek as my head burrowed in. With her hands outstretched in front of her, she grabbed a handful of sheets.

"Ohhhh FUCK!" She hollered as I pressed in.

She was impossibly tight and I didn't try to force my way in deeper. I stayed shallow and allowed her to acquiesce to my presence inside her.

She was a quick learner.

Soon I was doing nothing but providing a backstop as she slid herself down the length of me until I felt her ass cheeks flush against my hips. Once she reached that milestone she took over, lurching forward and back at varying speeds. All I could do was latch onto her backside and stand tall. Her moans and screams of passion were intoxicating.

That's when I felt something.

Not the I'm-Going-To-Bust-Feeling but something different yet familiar. Then again. Something pressed against me. I looked over my shoulder. Emily was behind me. I could see the faint outline of a harness around her waist but the rest was a mystery.

Until it again pressed against me.

It was a strap-on.

And based on how it glided down my ass and against my balls it was long and slender. I was speechless until a few choice words made sense.

"FUCK THAT'S GOOD!" I gasped as Emily penetrated me gently.

I had nowhere to go as Deneisha continued to operate in her own world of erotic anal euphoria, stuffing herself with my cock and moaning faster and louder. She surely had no idea that I was simultaneously being driven down the same path to assgasm. Emily's hands gripped my waist as she buried herself inside me.

"Oh fuck, you're deep," I whispered.

"You like it when I go deep?" Deneisha asked between pants. She was gaining confidence and hell-bent on bringing me to the brink. She pushed her ass back against me. As she did, Emily followed suit, pressing her hips against me until I was perfectly sandwiched between them: the plump and insanely tight ass of Deneisha and Emily's long and smooth cock.

Emily's hands ran up from my hips to my stomach and settled against my chest. I felt her tits smoosh into my back as she began thrusting upwards into me.

A trembling began. It started from Deneisha and permeated to me. A tingling overtook me as Deneisha cried out in euphoria that she was cumming. But before my tingling could culminate into an eruption Deneisha pulled away completely, leaving my cock dancing and begging for more. She collapsed onto the bed with her gaped asshole staring back at me.

"That was fucking amazing."

"You're telling meeee," I groaned as Emily rammed up against me and gyrated her hips.

Deneisha peered up from her post-coitus heap.

"Oh shit! Em, are you fucking him?"

"I couldn't let him have all of the fun."

Emily let off a couple of quick pumps, forcing my throbbing cock to lurch upwards and a soft whimper to seep from me. She then bent me in half so my back arched as I placed my hands onto the edge of the bed.

"I could tell he wanted it," Emily added with a loud smack against my ass. I moaned and buried my face into the mattress. My cock swung wildly as Emily increased her speed. I felt the bed rise and assumed Deneisha had gotten up to get a better angle. I didn't much care aside from wanting to put on a good show so I reached back with both hands and spread my ass further and moaned unapologetically. It was all I could hear.

And then it all stopped.

Emily extracted herself from me and I stayed face down for a moment eagerly waiting for her to slam back inside me. Nothing happened. I twisted around to see why.

And there they stood.

Emily's toned body still clad in boy shorts and a tight white tank with her strap-on still jostling side to side. Her hands resting on her hips.

Deneisha, her body glistening with sweat. Around her waist protruding from a lace harness a flesh-colored dildo with a pair of firm testicles at its base. She stroked up and down it with a hand dripping with KY.

"What are you going to do with that?" I asked dumbly.

"I think you know where it's going," Emily smirked.

"Looks pretty big, don't you think?" I asked.

"Seven inches. Give or take. Same as you. We'll see how good your memory is. Although," Emily peeked under me and then back at Deneisha's member. "Maybe hers is a little thicker."

I began to prop myself up on my elbows and knees.

"What are you doing?" Deneisha asked still stroking her cock.

"Don't you want me doggy style?"

"Uh-huh," she shook. "I wanna watch you take it."

She stepped to the edge of the bed and helped roll me onto my back. She grabbed the back of my calves and raised me to a proper height and angle. I was about to tell her to go slow when the tip of the strap-on pressed against me. I could feel the defined ridges of its head stretch inside me.

"Ohhhh FUCK." I yelled out.

Deneisha kept going. I reached my arms over my shoulders and grasped two handfuls of sheets beside my head. I closed my eyes and moaned some sort of primal shudder that struck both Emily and Deneisha as riveting.

"Oh my god, look at him," Deneisha said with a subtle push.

"I think he likes it," Emily added.

"I think he loves it. Do you love it?" She timed the question to coincide with a long slow thrust causing me to moan an emphatic yes.

"Did you like the way you fucked my ass? You were sooo deep." Another choreographed question yielded another resounding yes.

"Do you like it when I go deeeeep inside you?" Her hips were flush against me by the time she finished the sentence.

"Ohh fuck yes. You feel so good."

"Yeah?"

"Yes, baby. Fuck meee." I moaned as a warmth overtook me.

"Look at his cock," Emily chimed in. "I think he's cumming!"

I glanced down to see cum oozing from my dick and into a pool in the ridges of my abs.

"Ohhh it feels so good," I gasped.

"Does it, baby?"

"Yeahhhh," I closed my eyes and rolled my head back.

"You want me to fuck you harder?"

"Yeahh,"

"Yeah?"

"Yesss," I yelled.

Deneisha grabbed me by the ankles and proceeded to go to town on me. Her hips swinging unapologetically inward and out, the slaps of her skin smacking mine competing with my moans of pleasure. I was no match for her intensity and rhythm and she knew it.

They both knew it.

Emily grabbed onto my cock with a slippery hand and stroked me mercilessly as Deneisha continued to pound my ass. They remarked to one another about my ability to take their cocks and cooed encouragement. All I could do was moan feebly in return. Time lost its value but it surely couldn't have taken long before long beams of cum shot from my dick. The first burst crashed into my closed eyelid while the next two pumps both managed to find their way into my mouth, albeit by different routes: one landed on my tongue while the other hit my lips and dripped down. I may have even licked it clean. Emily and Deneisha both said I licked it. The rest of my load plunged onto my chest and stomach. Each girl continued to stroke and thrust, unwilling to be the reason why every drop of me was not expressed.

Then it all stopped. The stroking and the thrusting. Deneisha pulled herself from inside me while Emily dropped my dick so it slapped off of a puddle of cum. I trembled with both acts. Completely emptied and spent, I spread my arms out across the bed. They each crawled up onto their respective side and swung a leg over mine. Their cocks resting atop me while their arms found dry spots on my chest.

"Never have I ever done anything like that," I said after a moment of harmonic breathing.

All I heard were a few slight snickers. I looked down to see them both holding their hands up above me. Emily dropped one finger, leaving her with none while Deneisha waved a single digit proudly.

"Seriously?" I asked. "I need to meet your friends."

"Sounds like you already have," Emily assured me with a grin.

"How so?"

"That chick you met at MacDinton's? That's Sandra. She's in my Orange Theory class."

"What?" If I had a shred of energy left I would've sat up.

"Yep."

"What'd she tell you?"

"What you told us."

"Which was a major turn-on," Deneisha interjected. "Which is why you got such a treat."

"So you knew I'd been pegged."

"Yep. And she wasn't lying either."

"About what?"

"That you can take a mean dick."

I smiled bashfully.

"She said next time she wants in."

"Next time?"