A Dildo In My Ass

I never once thought of myself as gay. Throughout puberty my interests, my fantasies, and my naive experiences were all straightly dead center aimed at women. When fantasy finally became reality when I was 18, I knew that I loved fucking women more than anything in the world.

Time drifted on, sexual partners came and went, and one day I found myself 35, single, and entertaining 5 women at an after party in my hotel room after a rather yawn-inspiring cocktail party to close out the conference. Two handles of vodka on the table and a couple of dubiously sourced gummies later, the party was getting a little out of control. Blythe, Claire, Samantha, Jenny, and Cait were drunk, horny, and proud.

Blythe stole my tie and wrapped it around her head. Sam put Tupac on her Spotify account and cranked it as loud as it could go for a cellphone. Claire and Cait started to play quarters on the coffee table like we were 20 years old, except they got the rules of the game mixed up with something else entirely and proceeded to strip off articles of their clothing when one of them landed a quarter in the shot glass.

This wasn't about anything I'd done to deserve this display, mind you. I'd been in the right place (the hotel bar) at the right moment (when we were all getting toasted as the bar closed) with the right attitude (fuck it, let's get drunk!). The girls were barely paying attention to me, except for Blythe, who was clearly intimating that she'd prefer to stay in my room after the festivities died down. She'd wink at me constantly and at one point simulated fellatio with a hotel pen when she thought no one but me was looking.

There was a knock at the door, and everyone turned in that direction. Claire got up and opened it nonchalantly.

"Roger!" Claire exclaimed, rushing to hug him at the threshold.

"Hey gorgeous!" Roger exclaimed, his voice sweet and modestly effeminate.

"Guys, this is Roger, he's on our support team."

We all greeted Roger warmly. He was a short, African American man with a narrow build and a bald head. Probably in his early thirties, he was clearly very fit despite being a foot and a half shorter than me. I felt drawn to him somehow, for reasons that I cannot consciously explain. He was charming and funny. As the night dragged on he egged Claire and Cait on until their tits were out and their panties on the floor. The rest of us howled with laughter. Blythe sat down on the bed next to me as I watched the quarters gone wild exposition. She put her hand on my knee and slid it up to my crotch while everyone was laughing as Claire spilled a shot of vodka all over herself.

I looked at her, and she motioned her head toward the bathroom. I didn't need much convincing. I got up and walked nonchalantly to the bathroom, closed the door, and waited on the edge of the tub. Five minutes later, Blythe snuck over and joined me. I stood up to greet her and she wrapped her arms around me and kissed me deeply, moaning quietly into my mouth as our tongues danced shallowly. She fumbled for my zipper and I grabbed her soft, rounds tits. She shivered with excitement and dropped to her knees to finish unzipping me. Reaching her hand into my underwear, she grasped my throbbing dick and pulled it out, gasping quietly and looking up at me greedily. She opened her mouth and stuck out her tongue, proceeding to bouncing the head of my dick ok her lips and licking my sex right where the shaft meets the head. I moaned with anticipation. Then her phone began to ring.

It vibrated loudly and brightly on the faux marble sink. At first she ignored it, easing my shaft into her mouth and cupping my balls. After the fourth buzz, though, her concentration broke and she let out a deep sigh that ran from her head to her toes. She pulled my cock out of her mouth and turned to the countertop to grab her phone.

"Hello?"

...

"Yeah, I told you I'd be home late because of the conference."

...

"Just some friends. Yeah. Don't worry. I'm headed home now."

She hung up the phone and looked at me with disappointment.

"I'm sorry, but I only live 40 minutes north of town and I kind of promised my boyfriend I wouldn't stay the night for the conference."

I chuckled. "Boyfriend, huh? Does he know you're sucking my cock in a hotel bathroom?"

She rolled her eyes at me teasingly and sucked on the head of my penis forcefully, pulling it out of her mouth with a loud POP.

"Some things aren't meant to be." She shrugged. "But I'll see you at the November conference in Tulsa."

"I look forward to it."

She crept out of the bathroom and I lingered behind her until she'd gotten settled at the coffee table again.

"Where's Jack?" Samantha asked.

"He went down to get something out of his car I think," Blythe nervously answered.

I sat in the tub in the dark for maybe 15 minutes. My drunken brain awash in the sort of frustrated sexual calculus that plagues a man who set his course for getting laid to the pole star of drunken silliness. I heard the ladies discussing their next moves. It was generally agreed upon that it was time to go. But Claire was now passed out drunk without a shirt on. Roger assured them he would stay and look after Claire. I heard the click of four pairs of high heels patter down the path to the door, and the definitive sound of the thick hotel door slamming shut. I made my way out of the bathroom.

Claire was asleep on the couch beside a coffee table worthy of any fraternity house. Roger sat in the chair next to her, scrolling away on his phone. Something about his face was...well, cute. It endeared me to him immediately.

"Just you and me left standing!" I said, sitting in the chair across from him.

"Looks that way." He said, sighing to indicate the late hour. "She's not going to wake up for a few hours."

"Yeah," I said.

He looked at me and grinned. "You and Blythe....in the bathroom. She's a sexy thing. Did you fuck?"

I smiled and shook my head. "Her boyfriend called just as things started to get interesting."

His grin widened. "Poor fella. Didn't get the release you were hoping for."

I took another shot of vodka. It was astringent and burned my throat. Fuck I was horny, I thought. I could feel my cock in my pants, still throbbing from her parting kiss. My head was swimming from the unrequited lust pulsing through my body. This apparently did not go unnoticed.

"You're really turning me on," he said. "That bulge in your pants. How red your cheeks are."

I could just feel the tension. It was unmistakable. And the fact that it was a man did nothing to damper that. Roger got up to get a glass of water and I reached out my hands to stop him.

"What are you doing?" He asked.

"Sucking your cock, big boy." I said, without even thinking.

I deftly unzipped his pants and yanked them down to his ankles. Roger may have been diminutive, but boy was he hung! I marveled briefly at his girthy 8" cock before shoving it down my throat. It was exhilarating. I could barely fit my lips around him, and I worked desperately to fit his length deep down my esophagus. I gagged as he grabbed my hair and proceeded to fuck my face.

I have always assumed women suck dick to please their men, and that it was always done begrudgingly, no matter how zealously enthusiastic the performance. That may well be true, at least for a great many women, but that certainly wasn't my experience with Roger's cock. It was thrilling. The way his thickness stretched my lips and strained my jaw. The way he stretched out my throat. The musky taste of him when I sucked on his balls as I stroked his hard shaft. The raw power of it in my mouth!

"Do you like how I'm fucking your throat, baby?" He asked.

"Mmmhummm grgl" I managed to mutter as he plunged deeper. I pulled him out to gasp for air. "Aaaahuh." I coughed. "Yes daddy! I can't get enough of that beautiful cock!"

I couldn't believe the words coming out of my mouth. What the fuck am I becoming? I pushed these thoughts away and licked him again from tip to ballsack. "Fuck my ass, Daddy?" I begged.

Seriously? I thought. Apart from the time Lara stuck her finger in my ass while she rode me reverse cowgirl in college I'd never let anyone even TOUCH my ass. Now I wanted a stranger to fuck it?

Roger's eyes were on fire. My sloppy deepthroated blow job had obviously melted his brain, and he grabbed me forcefully. He pushed me onto the bed and pulled my pants off, exposing my rock hard dick. He grabbed my shaft and looked at me.

"You have a beautiful cock, Jack. I want to suck it and then stroke it while I fuck your asshole."

I nodded with pleading eyes. He opened his mouth and sucked my cock delicately. I moaned with delight as his tongue traced patterns on my frenulum. He let up on me to spit on my cock and my asshole, his left index finger massaging my butt while his right hand stroked my penis.

"Oh my god, where did everyone go?" Claire exclaimed, just as Roger's finger was relaxing my sphincter.

Roger winced in frustration. "They left!" Roger said. Both of us stood motionless in the dark hoping Claire was still too drunk to notice.

"Shit! I've got to go find them. Got to find them. Shit." Claire stood up and ran stumbling out of the hotel room.

"Fuck!" Roger exclaimed. He looked at me with frustrated disappointment. "I'll be back."

He dressed quickly and bolted after Claire. But he never came back. I didn't have his number or Claire's; Blythe never made it to the Tulsa conference, and our wild night gradually became one of those memories that haunt the periphery of your self-awareness when you consider ordering that second margarita at dinner.

But the thoughts of Roger - and what I was about to let him do to me - lingered much more vividly. The question of what it would feel like to take a dick in my ass began to haunt my daydreams.

One day in the late fall I was driving home from work. Traffic had gotten out of hand, and I opted for surface roads. The stress of the evening commute often pulls my mind to sexuality as a way to soothe anxiety, but for some reason on this day the thought of Roger's cock in my mouth just kept playing in a loop in my brain.

At a red light, I glanced left and saw an adult entertainment store. My eyes flashed Roger's dick again, and I turned into the parking lot. After about 20 minutes of browsing through every variety of vibrator, pocket pussy, sex doll, and dildo you could ever imagine, I found a nice, chocolate brown dildo about Roger's size. The cashier seemed incredulous.

"If it's your first time, it's better to get something smaller." The middle-aged woman checking me out advised.

"I'm trying to recreate a memory," I told her. She shrugged disinterestedly.

I got home and unpackaged and washed the dildo. Unscrewing it, I put in two AA batteries and tested the settings, settling upon a function that pulsed intense vibrations every 4 seconds. I grabbed a bottle of lube I'd kept for a dry ex girlfriend, stripped myself naked, and hopped in the shower.

I held the silicone dildo in my hands and stared at it. It was so much like Roger's! I gazed at it for several long moments before I closed my eyes and sucked it just like I had with Roger's dong. I could feel my own manhood swelling as the dildo tickled the back of my throat.

I'm really doing this. I thought. I continued to blow the dildo while I squeezed some lube onto my fingers and massaged my ass with my free hand. My sphincter tightened at first but soon greeted my index finger. It was thrilling to feel my finger slide in and out while my ass sucked at it greedily. I could feel my blood boil inside of me as I took the dildo all the way into my mouth, to its faux testicles, and pushed my middle finger into my ass next to my index. I moaned softly and whimpered as the knuckles stretched out my hole over and over. Pushing in deeply, I probed for my prostate.

It's time, I thought. Now or never. My cock was as hard as concrete and I stroked it lovingly. I lubed up the dildo like they were slip-and-slides, and turned the vibrator on. I stuck the suction cup on the bottom of the dildo to the floor of the shower and slowly eased my butt down to meet it. I jumped a little when the pulsating head of this giant silicone penis started pressing against my tight asshole. "Oh God, it's so big!" I muttered as I pressed it in. I felt my ass opening before the sensation of pushing a giant shit overwhelmed me. I gasped, but pushed it on past my sphincter, grumbling pleasurably as I felt my ass suck the rubber cock another inch into my anal canal. The vibrations were intense, and I started dribbling precum everywhere. Each pulse sent the door to my ass clenching around this giant cock and pushed another dose of precum dribbling out of my dick. I began to pump my ass with the dildo faster while I jerked myself off.

"Mmmhmmm! Oh fuck!" I shouted, my sounds of pleasure bouncing off the tiles of the shower. "Fuck yes, Roger! Fuck my tiny virgin asshole! Mmmy fuck I love your big fat cock in my tight ass!"

I fucked myself faster in both directions until I drove the car straight off of the cliff. I groaned as the cum shot out of my cock like a geyser, my butthole clenching in waves around the hard shaft penetrating me. Oh God! I thought. "I really did it this time! Fuck!!!!!!"

The cum just kept squirting out of me. Ropes and ropes of thick sticky cum lined the shower tiles. After what was clearly the longest orgasm of my life, I succumbed. Negotiating the fat dildo out of me, I relished the faint burning sensation of my gaping asshole trying to close up, gasping to be filled by that monster cock one more time. I eyed the dildo in front of me and sucked on it to taste myself. What would have ordinarily repulsed me -the musky tang of dirty underwear - exhilarated me as I licked my juices off the dildo as though it were Roger's cum drenched member.

I don't know if I'll ever find Roger again. I do know I'm ready to be his filthy anal slut anytime, anywhere.