Smartass to Sub Pt. 03

I walked up the stairs, a little nervous. It's ok. I'm an adult. This is normal.

I nodded at the clerk and slowly made my way around the store. I really would have preferred to do this online but I had under a week and I couldn't guarantee shipping. I carefully made my selections and brought them up to the counter. The guy looked at me and smiled.

"Dry patch?" I rolled my eyes and shook my head.

"He's about this." I wrapped my hand around the biggest dildo I'd picked up with a sigh. "And currently I can manage..." I wriggled my index and middle finger at him. He laughed at me- sex store clerks are always so relaxed. I don't think I could shock him with anything. He looked at my choices and shrugged as he rang them up.

"Well good luck." I sighed.

"Yeah. We'll see."

I didn't really know why I wanted it so bad. Why was it Ryan I was thinking about when I wasn't thinking about anything? His stupid texts made me smile to myself on the bus. I was almost looking forward to seeing him arrive with my coffee everyday. I didn't get it.

There were so many better guys out there. Hotter- well, maybe. Smarter, definitely. Kinder. But those guys didn't disarmingly get me on my knees from time to time. Maybe it wasn't quite as satisfying telling them what to do because they always wanted to do it.

Maybe I just liked a guy who had a bit of fight in him.

Maybe I just liked a guy who drove me a little crazy.

Maybe I liked the way I drove him crazy back.

——

"What the fuck did you do to him?"

I glanced up as Caro sat down beside me.

"Huh?"

"He was coherent. He sounded like he cared. He sounded like he's actually done the work."

"Oh, Ryan."

We'd had a meeting just before lunch and for the first time in his life Ryan had volunteered to discuss the latest issues. Well. He sort of volunteered. I sort of told him he was doing it. We had a new game. It was called do whatever the fuck I say Ryan, or I withhold my ass. It was working out splendidly in my favour.

Caro looked at me and I shrugged.

"You've done something to him."

"We're fucking. That's it." I hissed.

"Whatever. I approve. Although I'll be fucking pissed off of he gets a pay rise before me." I rolled my eyes- although that was looking more and more likely. Our bosses already thought the sun shone out of his ass, his newfound competence was probably all they needed to convince themselves he deserved a raise and a promotion.

Asshole.

My asshole.

I caught his eye as he walked past my desk and he grinned at me. I grinned back as I glanced at the time. He had 15 minutes to get through his inbox. I tapped my wrist casually and he rolled his eyes with a smile. I knew he'd get there. He was a surprisingly conscientious worker with the right kind of motivation.

--

It started with pictures. I figured I could do that. The Friday after we hooked up he practically begged for them when I told him I was trying a new dildo. I almost obliged him, pulling my legs up and pushing my arse out... but before I hit send I remembered I was pissed off at him because he'd ignored an email reaming us for an overdue report and he let everyone else take the fall.

Flick an email to Erin apologising for your part in the report and then ask me.

Was that an email I'm meant to reply to?

Well it's common decency.

Oh.

I flicked through reddit waiting for him. I was logged into my porn throwaway and told gayboynate1991 that I wanted to nail him so hard when Ryan got back to me. He'd b'ccd me in to an astonishingly humble apology.

I didn't know that was a thing I was meant to do. Was that alright?

He texted.

That was perfect.

I grinned and sent him the picture. He called me like two seconds later.

"Fuck yourself while you talk to me." He demanded. I felt my dick spring to attention but I tried to ignore it.

"I'm busy."

"You answered. And besides that you're sending me pictures of you violating your ass at 6.30 on a Friday, can't be that important."

"I have emails."

"What, you gonna do them with that hanging out of your ass?"

"Maybe."

"Oh fuck that's hot. You being all professional and sorting shit out while you're sitting there half naked with a dildo up your ass." He moaned. "Don't you ever switch off Sammy?"

"Once a week with some jerk from the office." He laughed.

"That's not switching off. I bet you have a list of things you want me to do and you're gonna make me do them before you deign to fuck me."

"Pretty much." I grinned into the phone. "Stop touching yourself."

"How did you..."

"Oh please."

"Ok. Fine. But this better lead to me touching myself because I am so fucking boned up right now."

"We'll see." I bit my lip as I stated to gently rub my fingers along my own dick. "Noticed the bottles had piled up a bit when I was there on Wednesday." I said casually. Ryan groaned.

"You're killing me Sammy." I moaned.

"I know baby."

"I gotta do the recycling before I can jerk off?"

"Oh no way man. That's crazy. You just gotta do the recycling before you can jerk off in the phone to me while I fuck myself with this big fucking cock."

"Oh fuck dude. Tell me what you're wearing."

"A fucking three piece suit." I rolled my eyes. "What do you think I'm wearing?"

"Tell me." I could hear the clink of bottles and I grinned to myself. Not that I actually gave a shit about Ryan's ability to keep his flat clean. I just liked bossing him around. I wanted to see how far he'd go for me.

"Well nothing from the waist down."

"Oh fuck yeah. Do you always do your emails half naked?"

"Yeah, sometimes."

"Because you're such a damn slut you can't control yourself." I smiled.

"Sure, if that works for you."

"It works for me. Hold up. Gotta take the bin out." I heard him grunt and the jostle of glass on glass for a second before he returned. "Still there?"

"Yeah."

"Got a shirt on?"

"T shirt."

"Band?"

"Mastodon."

"Sweet." He sounded like he was smiling. "Please tell me I can touch myself?"

"Hmmm..."

"Please!"

"Ok baby. You can touch yourself. Just touching though. You can just hold that big dick for me and squeeze it a little."

"Oh Sammy..."

"Good boy, just like that." I paused and lay on the bed with my legs spread. "What are you wearing baby?"

"Ugh... shorts... they're round my ankles..."

"No shirt?"

"Na."

"You take out the bins shirtless?"

"Uh... yeah..."

"Because you get off on your neighbours seeing you."

"Yeah."

"So I'm not the only slut who gets home after a long week and can't stop himself." Ryan grunted. "I said just squeeze it."

"Please, please, I need to jerk off Sam."

"I know you do baby."

"Please. What do you want?"

"I want you to play with your tits. I want you to think about me lying here, with my legs spread... I'm just slowly teasing myself Ry, this dildo is just slipping right in. It feels so damn good... uh... I feel so full..."

"Oh fuck yes. Does it feel as good as me?" I rolled my eyes. Given that right now I didn't know how he felt, and quite frankly I suspected he just felt like a world of pain I couldn't really answer that honestly. So I said what he wanted to hear.

"Baby it's half the size of you. Nothing feels as good as you."

"Fuck."

"You can jerk your dick Ry. Just gently. I don't want you to cum too early. That's the thing this toy has over you. You got pretty bad stamina don't you, Ry?"

"Sammy..."

"Say it."

"You're better than me." I blinked and paused. I had one hand on my dick and one hand plunging the dildo in my ass as I talked, the phone resting on my pillow. I moaned as I processed his words. He could hear my excitement. "My stamina is pathetic." He whispered. "I get so horny around you. I can't keep it together. I'm like a ... like a little premature boy."

"Oh good boy." I whispered. "You miss my dick?"

"Yeah." He whispered. "I miss being... spread for you... I miss looking up at you and knowing you're in charge."

"Oh fuck yes." I could hear him panting, getting faster. "You're gonna cum before I even get started if you're not careful."

"Please... tell me what you're doing..."

"I'm fucking myself. I'm pretending it's you with your rock hard dick, slowly fucking me. You hope you can control yourself because I'm moaning... it feels so good- you're splitting me open... you're trying to turn me into your needy little bottom, craving your cock.."

"Yessss..."

"Fuck me Ryan. Fuck me please."

"Yes baby. Oh fuck. I'm fucking you so hard. That tight little ass. That tight ass that won't fucking loosen up for anyone but me... my ass, on my hot fucking man... oh god, you're so good puppy. You're so..." He grunted and his breathing was erratic through the phone.

"Don't stop baby. You can cum. Just lose control and cum for me like a bitch..."

"Yes..." He whined and we panted into phone as he wanked furiously and I tried to focus on my ass and my dick at the same time.

I heard him lose it. He had a low panting grunt and he growled as he came.

"Sammmm." He moaned. "What have you done to me?" I whined in frustration. I really wanted to finish... He heard and started whispering into the phone. "You've made me your bitch, Sam. I'm a ruined top. I can't fuck properly around you... I need you too much. I can't control myself..." Ah god... I moaned into the phone as I humped against the dildo, grinding it into my prostate, my hand clenched tightly around my dick as I gyrated my hips.

"Oh fuck Ryan."

"Cum for me puppy. I want to hear you moaning my name. Bout time your neighbours learnt who you really belong to."

"Ryan!"

"Yes, good boy." I grunted and started to cream myself, my cum hitting me in the chest in short hot spurts. I moaned as I lay back and gently felt the rim of the dildo lodged in my ass, teasing it gently. I sighed.

"Good chat." He laughed.

"Wear that butt plug on Monday. I wanna see you squirm at your computer all day."

"Sounds good."

"Really?"

"Yeah. Anything else?"

"Anything else?" He sounded delighted. "His about no underwear on Tuesday?"

"Ok. Anything else?"

"Huh? How about you say a sincere thank you instead of huffing and rolling your eyes when I bring you coffee?"

"Deal." Ryan groaned.

"Oh I see. Bastard. Deal. Ok, what's my end?" I grinned.

"Well. Your end is a little harder but I'll make it worth your while."

"Ok..." He sounded excited in spite of himself. I wondered if he was getting hard again. I was.

"Polish those shoes you wear to work, you look scruffy." He laughed. "What does your morning look like?"

"Uh... I go for a run. I have a shower, I eat breakfast... I hit the gym for a bit, but only if you're there really. Then I get our coffee from Mojo and head to work."

"So why are you late to work all the time?" He sighed.

"I guess I could get up earlier."

"Good boy. If you're late to work this week I might have plans on Wednesday."

"Asshole."

"You're gonna need to get up way earlier because I want you to add something to your routine."

"Go on."

"After your shower I want you to lie down on your bed in a pair of tighty whities and I want you to jerk off until you cum. And then I want you to get dressed. I want you to wear those cum stained y fronts all day."

"Oh that's hot." He moaned. "Gonna need some seriously good jerk off material though."

"I could probably arrange that." I bit my lip. "But if you're jerking off to me you better give me a very nice thank you afterwards."

"Yes sir."

"Good boy." Ryan moaned.

"Fuck it Sam, come over." I sighed as I looked at the time.

"Shit. I want to. I have plans tonight though Ry." He sighed.

"Alright. Go hard on those emails."

"I'll see you Monday."

"Yeah." I could hear him smiling. "Monday." He hung up and I slowly withdrew the dildo from my ass, feeling an emptiness I wasn't familiar with. I jumped on the shower and tried to hide all evidence of my debauchery. Fabe would be here any minute and now that the edge was off I wanted to give him a good time.

——

"Fuck yes Ryan..." I felt my head jerk back and sting as I was slapped in the face hard... my eyes widened as I realised what I'd said.

"Ryan?!" Fabe grunted in annoyance. "Asshole."

"Fuck Fabe... I'm sorry..." I winced. That was so unlike me. I wasn't the kind of guy who thought about other guys in bed. I was usually more than happy with whatever guy I had in front of me.

"Is he that top?" Fabe said. I blushed furiously and Fabe started to smile. "Oh Sam." He said. If I didn't know any better I'd say you have a crush."

"No I don't!" I said, sounding not unlike a kid on a playground stamping his foot and saying that girls have cooties. Fabe rolled his eyes.

"Happens to the best of us Sammy. One minute you're a hot top with a good rep and the next you're stupidly in love and willing to offer your tight little hole up..."

"Shut up!" I started to laugh in spite of myself. "So far my tight little hole is doing just fine."

"So far." Fabe teased. He started to kiss my neck tenderly. Maybe I was forgiven. "I think this might be the last time for a while Sam." He said slowly. "You're calling his name in bed... soon you're gonna want to stop fucking around."

"It's not like that!"

"Does he know it's not like that?" Fabe glanced at me. "Ah-huh." He said as he saw my expression. "See I really don't want to be around when that becomes a discussion." I hung my head.

"Let's make it count then." I grunted, and pushed him gently against the bed and kissed him. "You're beautiful Fabe."

"Oh shut up. I forgive you." He laughed and it turned into a moan as I thrust in again deeply.

——

I looked up as my coffee landed on my desk. I smiled sweetly at Ryan. I was already in a good mood because I'd received a text at 6.30 in the morning saying Thank you, sir.

"Thank you."

"You're welcome." He smiled and walked away, turning back to wink at me. Caro cleared her throat and I ignored her.

"Ugh." She said pointedly.

"Something I can help with Caro?"

"Don't 'you something I can help with Caro' me. You guys stopped pretending you hate each other?" I smiled.

"Just trying it out for size."

"Gross." I smiled.

"Busy day. Shhh." She huffed but it wasn't just an excuse not to talk, we really did have a busy day so we turned back to our work.

——

He walked into the bathroom while I was taking a leak and he grinned. I glanced at him nervously.

"Don't." I warned him.

"Don't what?" He smiled and went to stand beside me. I looked straight ahead and tried not to look at his dick as he pulled it out. "You got some nerve Sammy." He whispered. His hand drifted to my ass and he slowly slid a finger down my crack, feeling the end of the butt plug and moaning softly. "Anyone could come in and see this." I bit my lip and moaned in spite of myself.

"Don't." I whispered. He pressed gently and I pressed back.

"Don't take you in a public bathroom?" I glanced around in case someone was lurking in a stall.

"Don't make me want you to take me in a public bathroom." He laughed.

"Free stall." He said. I sighed and zipped up, waiting for him. He wasn't going.

"You shy?"

"No. I just came in here to annoy you."

Enough. I grabbed him by the collar and pulled him into a stall, slamming the door behind me. He grinned and pulled me into his arms, wrestling his hand up under my shirt and slamming us against a wall. I unzipped my trousers and his hand wrapped around me.

"Do guys tease you when they see you pee?" He whispered in my ear. Fucking God dammit. Why did that make me hard?

"You know exactly what happens to guys who tease me." I whispered back. He moaned. And then the door inevitably swung open outside the stall.

I froze and Ryan lifted me up, holding my head down close to his, his knee pressing between my legs and my back pressed tight against the wall. He stroked my hair and my legs wrapped around him instinctively.

We listened to whoever it was pee, and Ryan's shoulders starting shaking as the stream didn't stop. I squeezed my eyes shut, willing myself not to catch his laughter, but I couldn't help myself, and we held each other tightly, trying not to look at each other as the absurdity of our situation became too much.

The guy finished after honestly years, and Ryan let me fall to my feet. We both howled with laughter and I had to sit on the toilet to contain myself.

"I think the moment's gone." He said as we collected ourselves.

"I think you're right." I sighed and stood up, helping Ryan get himself together as he helped me. He stroked my face. "Try it again and I'll fucking..." He kissed me.

"Whatever that threat was it's not gonna matter." He said. I grinned up at him and felt something awful in my chest. Oh no. I really did have a crush on him.

—-

So when Hamish called I told him it was over, I was falling for someone else and I didn't want anyone else.

Na.

I asked him to dinner.

I was delighted to hear from him. We met in town for cheap ramen and I was even more delighted that he showed up 20 minutes late.

"Did you do that on purpose?" I asked him as he sat down, flushed and slightly sweaty opposite me. "Show up late so I have to punish you? Because you could have just asked." Hamish blushed.

"You know buses are shit in Wellington." He whined.

"Apparently so do you. Plan it better next time." He bit his lip and hung his head. Cute.

Hamish was tall and lanky. He had an enormous dick which was totally fucking wasted because he basically refused to use it. I wish we could have swapped. I think he kind of did too. He had red hair which always seemed to be between haircuts, and when he blushed, which I tried to make him do as much as possible, he went neon pink.

Hamish was my kind of man. A total, begging for it, pain slut. An absolute sub. The kind of guy who locked up his own dick for fun. Most guys want a top who makes them feel like a cute little slut but Hamish wants to feel like a worthless hole. Guys like him just don't come around often enough. I'd even risked losing my bond and modified my apartment just for him, I liked him that much.

I strung him up from the relatively inconspicuous carabiner on my ceiling and pulled out a cane that hadn't been used in so long it was gathering dust. He pretended he didn't want the punishment but I gave him a million chances to safeword and he just blushed at me, his hard dick leaking all over my cheap carpet.

"Dumb little sub." I brought the cane down hard on his chest and watched it flare red. "Thinking he needs to act up to get my attention." He moaned as I dragged the cane over his dick. "You make a nice art installation Hamish. Maybe I should keep you hanging here. So everyone will know what a hot little slut you are." He whined.

"Ugh... yes sir..."

"Yes sir what? Yes sir you want me to display you for everyone?"

"No, sir..." He whimpered. I brought the cane down again and he writhed.

"Make up your mind, Hamish."

"I can't think straight." He mumbled as I ran my hands over his body.

"I know baby. You're just a dumb little slut, aren't you?"

"Yes, sir."

"Say it."

"I'm a dumb little slut." He curled his toes as I hit him again.

"That's 20, baby." He sighed and blinked at me.

"Thank you sir."

I wrapped my arms around his hot body and gently started kissing his neck.

"You took that well, baby."

"Thank you, sir."

"I'm guessing you don't really want to live as an art installation for the rest of your life?" Hamish laughed.

"It's not going to work long term."

"That's a crying shame." I snaked my hands up his body and released him. He went limp around me, resting his head on my shoulder.

I let him rest for a second before I slowly disentangled myself. He stood up straight and clasped his hands behind his back, looking down at me. I grinned and raised my eyebrows. He blushed and immediately fell to his knees. Way too fast.