Relax: You Can Do It

I’m browsing inside a sex toy shop as I reach a counter and some shelves displaying dildos, cock rings, and other toys. The shop is not specifically gay, but it caters for whomever is looking for sex stuff and porn. The attendant is a handsome young dude, sitting at the register, flipping through a magazine.

I regard the dildos with mounting interest. I have never experienced cock up my butt, but the dildos initiated some ass twitching. All sizes, shapes and colors. I thought I understood the reason for the shapes and sizes, but the colors? From silver to pink to blue to red. Do I dare buy a dildo and see how it feels stretching my hole?

The few times I hooked up with a guy, I knew how my thick 7-incher inflicted pain on them.  Would I want this to happen to me? Again the ass twitching.

I reached for one of the thicker dildos and fisted it in my hand. Fuck! This would certainly inflict damage. I could notice that the attendant was not paying attention to me. After a while of consideration, deciding that I did want to experience ass stretching, I chose the thinnest dildo on display.

As I walked over to pay for my purchase, I felt a bit weird and a bit embarrassed. This was a first time for me, and what did my buying a dildo say? The attendant sort of disinterestingly glanced at the dildo and started to ring it up.

“That’s 26 dollars with tax,” he looked up at me, and I thought I could detect some kind of a smirk on his lightly bearded face. His nametag said “Ian”.

I fished out my wallet, pulled out a fifty and handed it over.

“Jeez,” Ian heaved. “Don’t you have anything smaller, dude? I’m out of ones.”

“Sorry,” I said.

Ian looked at the dildo again and then back up to me, meeting my gaze.

“Tight, huh?”

“Excuse me?”

“Whoever your buying this dildo for must be tight,” Ian smiled and winked.

My hole twitched.

“Would that be your first?” There was definitely a smirk on Ian’s face as he asked this. Rightly, he was assuming that the dildo was for me, probably telling by my blushing face cheeks.

This conversation was making me uncomfortable, but I nodded, blushing even more.

“Dude,” Ian lowered his voice. “You need to experience something a bit bigger. To get the real feel, you know?”

“The real feel?” I croaked.

“Uhuh. Tell you what. Why don’t I show you one that’s different from this hard plastic. More like rubbery and thicker. Dude, you will thank me for that.”

Ian slid down from his perch and walked around the register counter leading me back to the dildo display. He took down a skin-colored dildo, and yes, thicker than the one I chose, with a ridged knob and veined shaft, looking so much more real than the others. Ian held it out for me.

“Feel it,” he said.

I did. It felt like a real cock, but still not that real. It didn’t throb, of course, but it was quite a good simulation of a man tool.

“Or,” Ian’s look was more mischievous as he added, “you might want your first to be a real live one instead of a toy.”

My heart raced. I studied Ian more closely now that I figured the guy was coming on to me. My eyes slowly went from his face down his flat chest to his low-hanging jeans, noticing a bulge, down to his sneakered feet. He stood a couple of inches taller than me, and he definitely looked hot now that I am considering him in a different perspective than before.

Glancing around to check to see if there is anyone within earshot, I whispered, “You mean… you?”

Ian’s mischievous smile widened, grabbing his crotch and nodding.

“But dude. I mean… I never…” I stammered lamely, my hole twitch increasing by degrees.

“Listen, man. Hey, relax. I’m Ian, and I would love to help a dude out.”

“Tyler.”

“Well, Tyler,” Ian smiled extending his hand while holding the dildo in his other hand, shaking it a little. “Want to experiment? I got what you need, dude. And, I’ve been told that what I got is so much better.” Ian winked.

Conflicting thoughts and feelings crowded inside my head and I felt myself shiver as I glanced back down at Ian’s crotch. But what the fuck? The dude was hot and was offering.

Seeing that I hesitated, Ian added: “I’ll be off on my half-hour break in a few minutes. We can go upstairs and see if we can make you happy. What say you?”

I nodded, unbelieving myself, that I had just accepted getting fucked.

“Cool, Ty. Keep on browsing.”

With this Ian walked back to the register counter as a client approached with a couple of videos to buy. My whole body shaking, I tried to take control of myself. Was I really going to do it? With a stranger? A hot one, for sure, but still. He would be breaking my cherry. I always thought that fucking was an act of love. Now, my thinking was more of lust. It must have been all those dildos on display, and the handsomeness and forwardness of Ian that made me this susceptible.

I stared unseeingly at the rack of magazines, reflecting, lusting, twitching, feeling my armpits get wet. I jumped when I suddenly felt a pair of arms encircling my waist and a body pressing on my back. I made to pull away when I felt wet warm lips on the side of the neck and Ian’s mumble: “Let’s do it, sexy dude.”

With shaking legs, I followed Ian up the creaking stairs and into a medium-sized room. A couch. A desk with a laptop and a desk lamp on it. A chair. A set of shelves with boxes and magazines piled on them.

Ian turned around to face me, unbuttoning his shirt and exposing his chest. A patch of chest hair. Flat and ripped abs. Defined pecs. Pinkish nipples, a trail of hair starting at his belly button and thickening down into his low-hanging jeans. I let out a low guttural moan. Fucking sexy.

Ian grabbed my shirt and pulled me to him, placing his lips on mine. I relented and opened my mouth as his tongue darted inside. Both of us let out moans as we kissed. I was aware of his bare sexy chest pressing on me and his crotch plastered on my upper thigh.

“Strip for me, Ty,” Ian said throatily as he started to undo his jeans buttons.

I took a step back and started to undress. Down to my briefs, my cock already hard and stretching the fabric sideways, I watched Ian pull off his jeans and smile at me. He was wearing loose black boxers, and for some reason I thought that that was much more erotic than my boxer briefs, that what was still hidden inside those loose boxers was something to be discovered.

I had been with dudes before, and fucked a few asses. But most of them were the slutty type that went onto my cock seconds after we were alone and naked. I didn’t want to do that with Ian, not wanting him to think of me as a slut. Something in my head was urging me, why should I care? Ian was a stranger. Who cared what he thought of me? Still I stood back.

“Could anyone come up here?” I asked in a trembling voice.

Ian laughed. “I share this place with Rick, but he’s downstairs minding the shop. Relax, dude.”

“But what if he comes up?” I persisted.

“Oh, you would like Rick,” Ian teased, standing in his sexy loose boxers. “I have to warn you, though, you don’t want his horse dick anywhere near your ass.”

“Horse dick?” I stammered.

“Ten thick inches of hard meat, dude. Listen, are we going to talk about Rick’s dick or are we going to fuck?”

“Maybe I should have brought the thin dildo up,” I said, perhaps trying to delay the inevitable.

Ian snickered and pulled me to him for more kissing, grinding on me. “Dude, don’t be a wimp.”

I felt his hands slide under my briefs and grab my butt cheeks, pulling me tighter to him, his lips on my neck.

“Ian,” I tried to pull back. “Can I see it?”

Ian’s laugh was loud. He stepped back and pulled down his boxers, kicking them off to the side with one foot. I inhaled. Ian’s cock draped down over his nuts, and I estimated that in its limp state, it was even thicker than the dildo that I had wanted to buy and try on my virgin ass.

“Fuck, dude, it’s… it’s big,” I mumbled.

Again, Ian pulled me to him pushing my face down his chest guiding my mouth to his nipples. I licked and sucked on them as I felt his meat starting to get harder against my hip, thicker. I heard myself moan as I raised his arm and licked into his hairy armpit. Ian grunted, his hands rubbing up and down my back, then hooking my briefs waistband and pulling them down exposing my fuzzy butt.

From somewhere far away I seemed to hear: “Damn, bro, this butt is made to be fucked!”

My whole body shivered. I needed to see this cock that was prodding on me, now hard and throbbing. I slid down to my knees. What met my eyes was the largest dick I had ever seen. Trembling, I kissed the knob. Ian moaned. I kissed down the shaft. Down to the balls. I licked the insides of his hairy thighs.

“Oh, yeah, Ty, dude,” Ian moaned.

With my eyes glued to his thick bush, I took him into my mouth, my jaws stretching to accommodate the thickness. I gagged. I choked. I slobbered. And I swallowed.

Ian bucked into my throat, his grunts and moans getting louder, his hands grabbing my head by the hair. I was being face fucked. By a big cock. I estimated at least 8 inches.

Ian led me to the couch laying me on my belly. I felt so exposed, so out there, butt naked. Ian spread my thighs and went into my crack with his tongue. I almost screamed. Ian’s rimming was so experienced, the flicking, the slurping, the moaning. Ian lifted my hips to reach under me and grab my raging cock, pulling it backwards between my spread thighs. He alternated his licking and sucking between my cock, my balls, and my hole until I felt I was going to cream. I was getting sucked and rimmed at the same time and the sensations were out of this world.

After what seemed like seconds, or perhaps ages, the slippery tongue was replaced by a greased finger. Ian covered my crack with lube and started working on my tight hole.

“Relax, Tyler. This lube reduces pain.”

“Ian, dude, I don’t think I can take you, man. It’s too big!” I protested.

But Ian wasn’t going to be dissuaded. He kept massaging my crack and fingering my hole and when he inserted two fingers, it wasn’t that bad. I felt a bit numb down there, perhaps because of the lube or maybe I was too horned up to feel any pain.

And then the thick knob. Pressing. Stretching. Throbbing. Greased and ready to pop in.

“You ready, baby?” Ian said as he leaned on top of me and licked my neck.

And then there was the thrust.

“AAAAAAAAAHHHHWWWWWWWWWWW,” I screamed.

“Oh fuck, Tyler. Shhhh, man, easy. Fuck,” Ian clamped his hand over my mouth trying to stifle my loud scream as my ass felt ripped in two, the thick knob just inside my ring, clamping hard on it.

From far away, I seemed to hear the creaking of stairs.

“Guys, what the fuck? I was going to call 911. Ian?”

I strained my head backwards, saw flip-flopped feet, hairy legs, knee-high bermudas. I moaned into Ian’s clamping hand, squeezing my ring harder around the huge knob ridge planted inside me.

“Sorry, Rick, dude. This guy is taking cock for the first time,” Ian heaved, not moving.

“I fucking don’t care, Ian. You can fuck this bitch till kingdom come. But we have customers down there, and they were concerned when this fuck screamed. Keep it down.”

I watched as the feet moved closer and I was staring at a crotch. Rick grabbed my hair pulling my face up, and glared down at me. “You hear, bitch? Keep your voice down. Fuck, dude, you’re fucking sexy looking. I wouldn’t mind taking turns with Ian. Too bad I got to mind the store.”

The two guys were laughing with Ian’s knob just inside my hole. I panted. Rick left and I think I heard the slap of a high-five.

I tried to relax. I mumbled into Ian’s hand.

“What was that?” Ian said, removing his hand.

“Please go easy, Ian,” I muttered.

Ian pushed. I grunted burying my face into a cushion to stifle my scream. Although Ian was going easy, his cock was huge and I felt impaled. I desperately reached back and tried to push back on his thighs, but he owned me now that he was inside me. Was it only a just the head? Or a couple of inches? Or halfway in?

Another push and I almost fainted. Ian’s cock head popped my inner ring and stretched my tunnel. I clamped hard, my ring burning around the thick cock shaft. Ian kept going, inch after inch. I squirmed under him panting and grunting as he wrapped his arm around my throat, nibbling on my ear.

“Yeah, baby. So tight. Fuck, Tyler. I love your pussy, dude.”

After ages of cock shaft forcing into me, I finally felt the tickling of bush hair at my butt cheeks, sending shivers throughout my spine. I automatically relaxed as Ian pressed down on me. And the fucking started. Was I bleeding? Probably. The pain was excruciating. I could feel Ian’s sweat rubbing on my back as he fucked. Suddenly, I shivered and cried out. Something inside my hole sent electricity throughout my body. Ian’s cock head must have found my spot and I felt him moan deliriously as I clutched hard on his pistoning cock shaft.

“Ah, fuck,” Ian grunted. “Yeah, dude, do that again. Fuck. Squeeze on my fucking cock. Tyler, fuck yeah, baby.”

I took Ian’s pounding and rubbing my prostate each time his cock head pushed into me. I was leaking like a faucet, my chest wet with pre-fuck. Ian increased his speed. He kept mumbling into my ear: “Oh, Ty, I’m gonna cum soon. Baby. Fuck yeah.”

With a loud heave and grunt, not caring whether Rick or the fucking customers heard or not, I shot my load under me, pinned down by Ian, knowing that my hole was going crazy around his cock. He swelled, and with “Oh my God,” he spilled his jizz into my guts.

As a top myself, I knew exactly how it felt when my bottom cummed as I was still inside his fuck tunnel, how his ring spasmed around my cock, and I knew the intensity with which I flooded his clinging ass.

We lay panting and heaving, Ian pressed down on me, his thick dick still inside me, getting limp but pulsating, for what seemed like hours.

When Ian pulled out, I almost screamed again. The burning returned, but I felt empty. Warm jizz seeped out into my crack and over my balls. I remained plastered down on the couch, not daring to move. I felt Ian’s wet lips on my fuzzy butt cheeks.

“Awesome fuck, Tyler,” Ian said between kisses and little bites on my butt. “I bet Rick would love plowing this tight ass, too.” There was a snicker.

“In your dreams,” I managed to say through my teeth. “I’m going to walk funny for days.”

“Naah,” Ian said, and I could detect a smile, “I stretched you good. Stay here.”

I heard clothes rustling, creaking stairs, silence, more creaking stairs, flip-flops, clothes rustling, body weight on me, cock knob knocking on my hole. Scream. Hand clamping my mouth. A tree trunk pushing into my sore hole.

“Oh, god, Ian is right. This cunt is tight,” I heard Rick grunt as he buried his 10-incher balls deep.

Rick fucked me long and hard. He cummed with a huge heave. Pulled out. Slapped my butt. Left.

I remained sprawled on my belly on the couch, my own cum drying on my hairy chest, my hole screaming with pain, cum down my thighs.

It was the most fantastic virgin ass fucking that I was lucky to get.

I stumbled down, bought the thickest dildo, smirked at Ian and Rick, and walked out, trying my best not to moan. I thought I heard the smack of a high-five just before I exited the store.