Falling In Love With A Gloryhole Pt 3

I sucked hard on the tip, rubbing his low hanging balls in my hand and rubbing a finger against his taint.

Part 1 | Part 2


The stroll back to the shop was the opposite of a walk of shame. Max led the way, walking backwards for most of the time, casually avoiding tripping and falling. This weird cloud of sexual awkwardness I expected never showed- instead we chatted like two new friends getting to know each other. He was incredibly attractive and I knew that he was into me, but this morning established that a relationship with each other wasn’t what we wanted. And the more I thought back to my time with Darren and Colby before him, the more I knew a relationship was the last thing I needed.

We got back to the parking lot and went straight to the shop. Max pulled out his keys and unlocked the front door as the two of us stepped inside and out of broad daylight. The same fluorescent lights fell on me as I stood in the middle of the entrance, waiting to see what was in store. Max patted the countertop, telling me to hop up as he instructed, “Stay here. Let me grab everything I have in mind.”

“I don’t even get to see what you’re picking out?”

“Nope. Just sit here and look pretty.” He said with a smirk as he disappeared into the shelves.

I swung my legs back and forth like the pendulum of a grandfather clock, ticking away as I sat there wondering what I was getting myself into. In the world of sex play, I was as vanilla as they came. Before I moved here, I hadn’t so much as kissed a guy, instead I’d only ever given hand jobs because apparently letting another guy touch your dick wasn’t gay. The dude came out shortly after graduation which was a surprise to everyone in our class, except me.

Once college rolled around, my virginity weighed on me like the Freshmen Fifteen. And much like my classmates who’d packed on pounds from The frozen pizza and the soft serve ice cream in the school cafeteria, I was determined to lose it. That night eventually came in the form of a house party that Theo dragged me to. He was just as much of a desperate virgin as I was. And by the end of the night we’d both made it back to our respective dorm rooms with a partner in hand. Mine came in the form of Mikey, a cute brunette who admitted to me once we got to my room that he too was a virgin. The night was full of awkward laughs, confused looks and an over use of the question “Is this okay?” It was fine, for the most part, but I’d always had an urge for something more, even though I never knew what that was. Even with my last two boyfriends, I’d had this constant feeling at the back of my mind that the sex I was having wasn’t what It should have been.

Max came back with dozens of packages in hand as my self-reflection came full circle . He splayed them all out on the counter and my eyes grew wide as I looked at the haul.

“Decided to pick up a little bit of everything.”

I reached for the skimpy jockstraps he brought out, “Dude there’s barely any material on these!”

“That’s kinda the point, Robbie.” He said with a snicker.” These straps will really accentuate that cute ass of yours and this pouch will hold your cock in place even when you’re hard.” I nodded, wondering how I’d ever be able to go about my day in something so skimpy. But I knew that they’d look good on me, so I didn’t fight it.

The more I moved down the counter, the wilder the merchandise got. I didn’t question the dildo he picked out because it was smaller than he was, and something told me I wouldn’t have a need for fake cock anytime soon. My eyes did sear into the bright red butt plug that sat beside it, with it’s tapered tip pointing up at the ceiling.

“There’s no way this is going to fit in my ass.” I said as I looked at Max like he was crazy.

He patted my shoulder, “Trust me, it’ll fit. This one’s part of a set so we can start you off small and work your way up to this.”

I raised an eyebrow, “Oh so you’ve use butt plugs before?”

“I bought a set of my own a week after I started here.” He flashed me a wicked grin as I turned a shade of pink, “Once it’s in, it’s like having your prostate constantly stimulated. You can even slip on your clothes and go the entire day on edge... if you’re brave enough.”

I took the plug from him and set it along the rest of the stuff I was actually going to purchase. I didn’t need any more convincing. The thought of having something in my ass all day and the thrill of being the only person to know was enticing enough.

Max walked me through the rest of the items he had in store and one by one, they slowly made it into the purchase pile. Fresh bottles of lube, poppers, cock rings, beads and even a few prostate massagers joined the rest of the items. Truth be told, Max could have slipped in a thousand dollar sling and I would have agreed to it. The boy had this youthful nature about him even in the most adult situations. It was refreshing- to say the least- to be immersed into a world that I barely stuck my toes in, but his confidence that I’d enjoy myself was reason enough.

He rung the items up and I could hear the beeping of the scanner like a heart monitor, steady and unwavering. Not even bothering to look at the total, I handed him my debit card which he swiped right after entering his employee discount. A large opaque plastic bag later, and we were set. Just as I hopped off the counter, the door swung open, signaling that familiar chime.

A tall guy who looked about my age stepped inside. Max called out to him as his tanned skin bathed in the sunlight from the strips of un-tinted glass. “Hey sorry buddy, we’re actually closed right now. We open back up at four.”

Slipping his hands out of his skinny jean pockets, the guy replied, “My bad, man. I saw the lights on and figured you guys were open.” He turned, placing his hand on the latch and opening the door.

“Wait. Come here a sec.” I said in a voice that somehow escaped my body without permission. The guy turned back towards us and walked over, giving me a chance to see him in all his tall and beefy glory. A white long sleeve one size too small did wonders to show off his beautifully tanned skin and arms that seemed to test the strength of the fabric. As he got closer, I could smell his cologne- strong but somehow muted at the same time, enough to make way for a natural musk that I wanted to inhale like the jar of poppers I’d just bought.

Max whispered into my ear as the guy came closer, “Know what you’re getting into, kid?”

I nodded, not taking my eyes off him as he came up to the two of us. “I’m Robbie and this is my friend Max.”

“Diego,” he offered, in a silken medley of syllables that my white tongue could never achieve. He towered both of us and seemed to be watching, waiting for some explanation as to why he’d been summoned.

I hopped back up on the counter, gaining a few inches over the tall boy. “Max works here and had just picked out a few things he wanted me to try.” Diego raised an eyebrow, “I was hoping you’d give us a hand.”

Max came up from behind the counter, plastic bag in hand and stood beside me. He pulled out the jockstraps he picked out- this one white with accents of baby blue. I chuckled at his choice, knowing he’d picked it because it matched my eyes. He held it up to Diego, asking, “I think our boy Robbie here would look real good in these, don’t you?”

Diego lifted his hand and rubbed the soft fabric between his fingers, “Why don’t you try this on so we can see?”

I only nodded, stripping my shirt, in between the two of them and tossing it behind the counter. The two boys watched my every move as I unfastened my jeans and pulled them down below until only Max’s boxers remained. I caught sight of Diego eyeing my ass and biting his lower lip in the process. With my back towards him, I slipped off the boxers and into the new jock, coaxing the tight waistband over my shapely ass until I let go, snapping it in place.

I turned my head slightly, asking, “What do you think?”

The boy growled slightly, gnawing on that bottom lip like it was taffy, “I think we have a winner.”

I leaned into Max, arching my back to give Diego full view of my ass. Max was rubbing on my bare shoulders, watching Diego watch me. “You know, I fucked Robbie real hard last night. Why don’t you check if his hole’s still sore.”

I heard a wicked chuckle from Diego as he turned to me, asking permission with his near silver eyes. I nodded, worried that words wouldn’t do my lust justice. Instead, I spread my bare feet further apart on the vinyl tile and nuzzled my face into Max’s now bare chest. Diego stripped off his shirt too and I looked back to see his arms covered in a mural of tattoos that stretch from his wrist all the way up to his shoulder blades. The ink looked incredible on him, second only to the well defined chest with two equally hard nipples. I watched as the boy sunk down onto his knees, placing a palm at both of my cheeks and spreading them wide. I shivered as my hole was exposed to the air, only to be warmed up by Diego’s breath as he moved closer. The boy went straight for my pucker, sticking his tongue deep in me as I took one of Max’s nipples in my mouth. It was the only way to keep me from moaning too loud as he licked me for the first time. I shuddered, feeling his tongue lap up the creases at my hole, begging me to open up to him. His hands never stayed still either, kneading my cheeks in his palms and spreading them apart until he had the access he needed.

Max’s hands found my jaw and lifted it up to give me a kiss. I felt his hair brush against my face as his tongue entered my mouth. Fuck this feel good- to have two tongues with minds of their own, working only to taste as much of me as they could. I made out with Max for a while and it seemed like Diego wasn’t coming up for air anytime soon. The boy was as hungry as I was yesterday, eating out my hole like he’d been deprived.

When he did come up, he swung me around for a kiss, painting my lips in spit. He sucked hard on me, fingering my hole as he cupped my cheeks. I nearly lost balance had it not been for Max who wrapped his legs around my front, cornering me between two horny boys.

Diego pulled out of my mouth but kept his finger hooked into my hole, “You know I came here to check out the gloryholes, but this is much, much better.”

I gave him a wicked smile as Max crept up over my shoulder, kissing Diego as their hands roamed over my near naked body. Max slipped off his shirt leaving Diego even hungrier than before. He pulled out the red butt plug and waved it between us, getting our attention. He pointed the blunt end towards Diego, asking, “What do you say we give Robbie his first lesson in toys?”

Diego nodded, circling his finger against my wet hole, “He’s tight too.” He looked me in the eye, “This is gonna be fun.”

Max ripped off the plastic packaging and rushed off to the restroom to give the toy a proper cleaning. As he left, Diego turned to me, “So you and him- you guys boyfriends?”

I shook my head, knowing that no matter what I may have wanted, the truth remained that boyfriends was not what we were. “Nah, he’s just been helping me explore a little.”

Diego nodded, “Alright, cause I don’t do complicated.”

Max returned soon after with a now freshly washed plug. He came up to the counter and slipped out of his jeans, exposing his lack of underwear. I watched as his fat cock bounced around as he pulled off his socks, making my mouth water at this sight of his dick and bare feet. Diego joined him too, pulling off his sweatpants and long black socks until only his thick uncut cock remained. I reached over and took him in my hand, feeling the heat radiate off his shaft. Having never seen one outside of porn, I pulled his skin back exposing more of his pink head. He’d been leaking too, with the scent of his precum filling the space between us as I tugged on his shaft. He chuckled at my enthusiasm and placed a firm kiss on my lips.

Diego instructed me to bend over and I soon found myself in the same position as earlier. I kissed along Max’s abs as he hopped up onto the counter. He picked my face up for a second, and looking into me with those comforting eyes, asked, “You ready for this, man?”

I nodded to which Max took the plug and handed it to Diego along with an unopened bottle of lube. I looked back to see Diego pouring a generous amount of it into his open palm before rubbing it into my hole. His fingertips slid in with ease as he worked the lube all over my insides leaving the pouch of my white jockstrap completely soaked in pre-cum.

Once I was fully greased up, Diego took the circular base and aligned the tip against my hole. I could feel the cold rubber pressing against my skin as he gently poked around, teasing me with the tip. “Relax for me, Robbie”, he said as he slowly inserted it into me.

I jerked forward, pressing my forehead against Max’s chest and exhaling so many breaths that his furred pecs started to soak in condensation. His hands found mine too and I squeezed hard as Diego continued to push with steady speed. I bit down hard on my bottom lip, muffling my moans as my hole stretched more than I’d ever tried. I even felt my legs start to shake, tapping my bare foot on the vinyl tile.

After a few minutes, I felt Diego stop for a second. I could tell the toy was nearly all the way in and he was looking down at my stretched hole, admiring his work. He leaned forward and licked along my spine all the way up to my neck as he held it still. And once I felt his hot breath wrap around my right shoulder, he pushed the toy fully in, letting my hole close against the tapered base, held together only by the elongated edge. Diego took my ear in his mouth and sucked hard on my earlobe as I moaned out, feeling the toy lodged inside my hole.

“How does it feel, man?” Max asked as he rubbed up my chest.

“Full.” I replied in a strained voice.. “I feel like any slight motion could make me cum instantly.” I reached into the jock and held the base of my hard cock, relieving the urge to blow just from having the toy in me.

Diego slung an arm over Max and pulled him into a kiss as he leaned back against the counter. I watched them make out like a horny teenager who’d discovered porn for the first time. Butt Max didn’t kiss Diego with any of the playfulness he gave me, instead attacking the boy’s lips like two sets of magnets forcing their way back together.

I sunk down, feeling the edge of the plug brush up against my spot as I got down onto my knees. Before me, two hard cocks stood straight out and I grabbed each in both hands. I started with Diego, whose cock was leaking long strands of precum onto the cheap tile. Flicking my tongue along his slit, I lapped up his juices like sweet nectar. The boys pulled off each other enough to look down at me.

“You look so hot down there, Robbie.” Max said as he ran his fingers through my blonde hair. That gentleness that he’d abandoned with Diego resurfaced when interacting with me in a way that made me feel special. I felt his light touch at the back of my neck, softly pushing me towards Diego’s cock which I took halfway down on my first try. The taller boy moaned out, feeling my lips wrap around his shaft while my tongue massaged his tip.

“I could say the same from down here” I said with a smirk as I jerked both cocks in each hand.

I choked on Diego’s thick cock a little and pulled off, leaving a trail of kisses along his sun-kissed skin. I could feel the soft hair along his crotch rubbing against my skin as I made my way down towards his balls. The scent coming off them was intoxicating as my face closed in and took one of them in my mouth, eliciting a soft growl. I then took the other one in too, kneading them with my tongue as Diego cupped the back of my head. I looked up every now and then to see Max watching me with pride while Diego fell victim to my skills, barely able to open his eyes as I serviced him. Max’s cock was just as hard in my hand as I continued a slow stroke, not wanting to leave him out. After a few minutes of exploration, I made my way back to Diego’s cock and took him down even further, ignoring the sensation of choking and instead pushing my throat deeper until taking all of his length was the only option.

I felt his strong hands caressing my face as he lifted my chin, “Jesus Christ, you’re good at that.”

I looked back up at him with my bright blue eyes and his cock still halfway down my throat. I sucked hard on the tip, rubbing his low hanging balls in my hand and rubbing a finger against his taint. Max followed my lead and worked his hands along Diego’s chiseled body, tracing his ink with his fingertips and pinching his nipples. The boy was being stimulated in more ways than he was used to, but I was careful not to take it too far. I wanted him completely at his end.

Catching Max’s glance, I gave him a wink and turned to Diego. “I want you to fuck me.”

He didn’t bother to respond, instead, pulling me up quickly, causing the plug to shift in my tender hole. He gave me a firm kiss before turning me around to face Max who wore the same grin of lust that he had on last night. I swear, between his plump lips and a jawline that could cut crystal, the boy was as hot as they come. But the most attractive feature was the way he looked at me as if we’d been lovers for years, needing only to share a glance to tell the other what we wanted.

I sunk down on Max’s cock as I felt Diego’s fingers tracing along the edges of the plug. I relaxed as best I could as I he latched onto the end, slowly pulling it out and causing the edge to scrape along my spot like a drawn out orgasm. The friction between the slick rubber and my skin was unbearably good, leaving me sucking on Max’s cock, trying to reciprocate some of the ecstasy I was feeling.

As Diego continued to tug on the toy, I could feel my hole stretching with every sensation of my body focused on that area. Just when I thought I couldn’t take anymore, I felt the ridges of the plug pull out of me as the tip tapered down. That moment left me feeling so empty, as if the sensation of being full was all my body had known. The cool air of the store made contact with my gaping hole as I leaned there, as open as I’d ever been.

Diego wasted no time, slipping his hard cock into me mere seconds after as a long, steady breath escaped my lips. Any doubt that I was a bottom was crushed in that moment- I enjoyed having my ass full way too much to be anything other than.

I worked up Max’s cock, painting his head with my wet tongue as the taller boy pounded into me. I can’t tell you how incredible I was feeling- with endorphins igniting through every part of my body and setting me ablaze. This was how sex was supposed to be: passionate, uninhibited and carnal.

Max pulled me up for a sloppy kiss which felt more like a sword fight between two strong tongues. I felt Diego’s arm wrap around my chest, holding me close as he went in for some of the action. He slipped in between us and without skipping a beat, the three of us made out like it was the most natural thing in the world. The fight was over; there wasn’t any need for dominance. I folded when Diego’s tongue slipped into me and I felt him do the same when Max took hold of his lips. We were three men riding through this experience until our bodies couldn’t hold off any longer.

Diego moved first, breaking our three-way kiss and grabbing my shoulders as he pumped into my hole with so much force that Max had to hold me upright. Max was second, spitting into his open palm before taking both of our dicks in his hand. I was third, moaning loudly as these two boys worked up our cum shots. It was like watching a spark travel down the lit ends of three fireworks with only minutes before shooting off.

I’d like to say I was able to hold off the longest, but I just wasn’t strong enough. I came in Max’s hand, letting out streams of thick cum and moans that could be heard from the liquor store. “Oh my fucking God” I creamed out, feeling the cum shoot out of my dick.

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