26. Twenty-Five

I woke up on Saturday with a big grin. It’d been two days since Shepherd and I struck our agreement, and they’d been difficult. He was mostly gone Thursday and Friday, dividing his time between family drama he refused to share and work. In a few weeks, university classes would start, making him even busier, which intensified my desperation to spend time with him now.

But every time I thought about what we’d done Wednesday night, it brought a big smile to my face and made me shiver. The feel of Shepherd's thick cock sliding between my lips as I eagerly sucked him... his huge, strong hand gripping my shaft, stroking me until I exploded in ecstasy. The memories made me grin and giggle into my pillow like a giddy schoolgirl.

But then I remembered our deal. My ass clenched thinking about it. Today was the day I'd agreed to spend the whole day with a butt plug stretching me open as I did my chores. Completely naked. And I wouldn’t be allowed to get off.

I groaned and rolled onto my back. That last part was going to suck, but I couldn’t deny that some part of me found it hot as hell, knowing that I’d given Shepherd complete control over my orgasms.

I dragged myself out of bed with a sigh, my morning wood bobbing between my legs as I stood. That's when I noticed a handwritten note on the nightstand. I picked it up and read:

Eli,

Get dressed and come down for breakfast.

We have much to discuss.

-S

Even seeing his initial at the bottom sent a little thrill through me. I was so fucking whipped already.

I threw on some sweats commando style, letting my hard cock tent obscenely against the soft fabric. Might as well give Shepherd a show.

Padding downstairs, the rich aroma of dark roast coffee and sizzling bacon hit my nose. My stomach rumbled eagerly in response. Shepherd stood at the stove in his pajamas, looking unfairly sexy and put together.

“Morning, Sir,” I said, voice still gravelly with sleep. “Sleep well?”

Shepherd glanced over, dark eyes dragging over my body in a way that made me want to preen and show off. His gaze lingered on my straining erection for a long, heated moment before flicking back up to my face.

“Quite well, thank you,” he replied smoothly, plating two pieces of French Toast. “And you? How are you feeling?”

“I slept great, actually,” I replied, watching hungrily as Shepherd plated our breakfast. Damn, it looked amazing. My stomach growled loudly.

Shepherd's lips quirked. He carried our plates to the table and set them down before taking a seat himself. “Come sit, let's eat while it's hot.”

I plopped down across from him, not bothering to hide my raging boner. “I’m going to get spoiled on your cooking, Sir.”

“Perhaps,” Shepherd allowed, picking up his fork. “But you'll be earning it today, I assure you.”

A shiver rolled through me at that dark promise in his deep voice. Fuck.

Shepherd sipped his coffee, studying me over the rim with those intense, perceptive eyes. “Eli, before we begin, let’s revisit and amend our contract. We need to discuss adding sexual activity to our dynamic if you want to continue.”

I swallowed hard, my cock twitching eagerly at Shepherd's words. Sexual activity with him... God, yes, I wanted that. Craved it with every fiber of my being. “Yes, Sir, I want to continue,” I said quickly, my voice breathier than intended.

Shepherd nodded, looking pleased. He took another sip of coffee. “Very well. Let's discuss the specifics, then, shall we?”

He pulled a folder from the counter and opened it, revealing an amended version of the contract we’d signed. My heart raced as I leaned forward to read it.

“Let’s start with the basics,” he said. “Considering our previous encounter, can I assume oral sex is a yes?”

I nodded. “Yes, Sir. And…what we did after.”

“I’ve added cock warming as a preference,” he announced. “To be done at my discretion. Now, anal sex?”

“Receiving but not giving,” I said quickly and then suddenly felt sick. “I…um… I can’t do it the other way. It…It’s too much like…”

Shepherd's eyes softened. He reached across the table and squeezed my hand. “Topping is a hard limit, then. I'll add it to the contract now.” He jotted it down on the paper before glancing back up at me. “While we're on the subject, are there any other hard limits you want to share? Anything that's completely off the table for you?”

I chewed my lip, considering it. My past sexual experiences had been limited and fucked up, so I wasn't sure what my hard limits were. A few things came to mind immediately.

“The same as before, I think, but..” I paused. “I, um… I don’t like to be called names or insulted either. I’d rather be praised like you do for me, Sir.”

“Your limits are similar to mine,” he said with a nod. “But I’ll also add that I don’t do religious or underage roleplay, and pet play is a hard no for me.”

I nodded. “I have no problems with any of that.”

“What about sharing and public sex?” Shepherd asked.

I blinked and flinched. “Sir?”

“Group scenes,” Shepherd explained.

I swallowed hard, my mind spinning at Shepherd's words. The thought of playing with others, being shared or displayed, sent a confusing mix of anxiety and arousal through me.

“Sometimes I co-dom with others I trust,” Shepherd explained.

“Like Gavin?” I ventured.

Shepherd nodded. “Yes, like Gavin. But also with a few others I trust. Occasionally, I allow my submissives to play with other trusted doms' submissives too.”

I tilted my head to the side and leaned forward, whispering, “What does that mean?”

“It means,” Shepherd said slowly, “that I may ask you to engage in sexual activities with another submissive while I observe and direct the scene. For example, I might instruct you to give oral sex to another trusted submissive, guiding you through the act as I watch.”

I squirmed in my seat, imagining the scenario. “You mean, like, I'd be sucking off some other sub while you told me what to do? While you watched me?”

“Precisely,” Shepherd confirmed with a nod. “Or I might have the other submissive pleasure you instead. It could involve oral sex, mutual masturbation, rimming... any number of activities, all performed under my command and for my viewing pleasure. As long as it’s within your limits.”

I swallowed hard. The idea of playing with others made me nervous, but knowing Shepherd would be there, in control, eased some of my anxiety. Honestly, picturing Shepherd ordering me and another sub to get each other off while he watched was pretty fucking hot. It’d be like performing in a private porn, just for him.

“I think... I think I might be okay with that, Sir. Depending on the specific people involved,” I said slowly.

“Of course,” Shepherd agreed, making a note. “We’ll only proceed with group activities if you feel completely comfortable.”

“Thank you, Sir.”

“What about public play?” Shepherd asked, his voice low. “Specifically at The Playground. I've done public scenes often there. Sometimes for educational demonstrations on proper technique. Sometimes for the thrill of it. I enjoy putting my submissives on display, letting others see how exquisitely they submit to me, how eagerly they take my cock with an audience. It's a way to show that they are mine completely. That no one else can have them.”

Fuck. His words sent a bolt of heat straight to my core. I shifted in my seat, my cock throbbing almost painfully now. The thought of Shepherd claiming and taking me so publicly, showing everyone that I was his... it lit a fire inside me, a deep primal need I hadn't even realized was there.

I took a shaky breath. “I... I think I might be okay with public play at The Playground. But only if you're there with me the whole time, Sir. I trust you to keep me safe.”

Shepherd's eyes gleamed with satisfaction at my words. “Of course, Eli. I will never leave you unsupervised in such a vulnerable state. Your well-being is my top priority, always.” He made another note on the paper. “We can start slow, with you simply attending the club with me a few times to observe and acclimate before trying any public scenes. And we will discuss boundaries and specific activities beforehand.”

“Yes, Sir. Thank you,” I breathed out, some of the tension leaving my shoulders. Knowing Shepherd would ease me into it and never push me past my limits settled my nerves immensely.

“Now, let's talk about orgasm control and denial,” he said, and my cock jumped. “Controlling your pleasure and release is one of my favorite ways to dominate. I want you desperate for me, aching, on the brink and begging before I allow you to come.”

I shivered, my breath catching. The idea of Shepherd denying me, drawing out my need until I was mindless with it, sent heat searing through my veins.

“I'll use various methods,” he continued. “Making you wait for permission, forcing you to hold back your orgasm until I say, perhaps leaving you hard and wanting while I use your body for my own pleasure...”

I whimpered, squirming in my seat as my cock throbbed urgently against my sweats. Shepherd's eyes flicked down to my lap and his lips quirked.

“I may also employ chastity devices if needed,” he said casually, like he wasn't discussing locking up my dick. “To help you learn control and restraint, but I only like those as short-term solutions. I’d prefer you to develop your willpower and to obey me. However, I have used specific periods of chastity as a punishment for willful submissives before.”

The thought of being caged, my release entirely at Shepherd's mercy, was as terrifying as it was thrilling.

“I've never tried that before, Sir,” I admitted hoarsely. “But I'm willing to, for you. I want you to have total control over my pleasure.”

Shepherd's eyes darkened with hunger. “Good boy,” he praised, sending sparks skittering down my spine.

Shepherd made another note on the contract before glancing back up at me, his expression thoughtful. “What are your thoughts on impact play, Eli? Spanking, paddling, flogging, that sort of thing.”

I bit my lip, considering it. The cult had used beatings and whippings as punishments, but it had never been in a sexual context. The idea of Shepherd spanking me, though... I couldn't deny the spark of heat it ignited low in my gut.

“I've never done impact play for pleasure before. Only as punishment, and not in a sexy way.” I fidgeted with the hem of my shirt. “But... I think I might like it, if it was you doing it. But only with your hand. Nothing else.”

Shepherd nodded slowly. “I see. Well, impact play is not a major interest of mine in terms of sexual pleasure. I much prefer other forms of stimulation and domination.” He paused, tapping his pen against the contract. “That said, I do use impact play as a punishment sometimes, for disobedience or breaking rules. Though, being honest, I'm not convinced it would be a particularly effective deterrent for you.”

I couldn't help but cock my head curiously at that. “Why do you say that, Sir?”

“Well,” Shepherd mused, tapping his pen against his full lips. “I imagine denying you the privilege of sucking my cock would be quite effective. Forcing you to suck a plastic dildo while I stroked myself just out of reach instead...”

I whimpered, my mouth watering with the phantom taste of Shepherd's thick cock on my tongue. Fuck, why was that so hot? The thought of being made to worship and serve Shepherd in such a degrading way, debasing myself for his amusement...it lit a fire inside me, even as it made my cheeks flush with humiliation.

I squirmed in my seat, Shepherd's dark promises making my head spin with a dizzying mix of humiliation and desperate arousal. He knew exactly how to push my buttons, to make me ache for his dominance in ways I'd never imagined.

“I think that covers the main points I wanted to discuss,” Shepherd said smoothly, setting his pen down. “As always, we’ll discuss this again tomorrow night and every Sunday after for the duration of the contract, making changes as needed. Do you have any other questions or concerns about the amendments to our contract, Eli?”

I swallowed hard, trying to gather my scattered thoughts. “No, Sir. I understand and agree with everything we've discussed.”

“Excellent.” Shepherd slid the contract across the table to me. “Then let's both sign and make it official, shall we?”

With a shaking hand, I scrawled my signature on the line below Shepherd's elegant script. As I watched the ink dry, a shiver of anticipation rolled through me. I was really doing this. Giving myself over to Shepherd completely, trusting him with my body and pleasure and submission...

“Good boy,” Shepherd praised as I handed the contract back to him. He tucked it neatly into the folder and stood. “Now, I believe you have a task to complete today, don't you?”

My stomach flipped, a fresh wave of nerves and excitement crashing over me as I remembered. The plug.

“Yes, Sir,” I said, my voice coming out slightly breathless.

I followed Shepherd to his bedroom, my heart pounding faster with each step. He opened the nightstand drawer and pulled out a sleek black silicone butt plug, holding it up for me to see. It was bigger than I expected, with a flared base and a tapered tip. My hole clenched looking at it.

“This is going inside you today,” Shepherd informed me, his deep voice sending shivers down my spine. “It has a remote controlled vibrator that I'll be controlling. You are not allowed to come until I give you permission. You’re not to remove it for any reason without my permission. Understand?”

“Yes, Sir,” I breathed, my cock already aching and leaking in my sweats.

“Good. Now strip.”

I obeyed quickly, shucking off my clothes and folding them with shaky hands. Then I stood naked before him, my stiff cock jutting out obscenely. Shepherd's dark gaze raked over my tattooed body, lingering on the glinting metal through the head of my dick. I had to fight the urge to cover myself, unused to being so exposed and vulnerable.

“Bend over the bed,” Shepherd ordered. “Legs spread.”

I did as I was told, the cool sheets a shock against my overheated skin as I lay my chest on the mattress and reached back to spread my ass cheeks wide. I heard the snick of a bottle cap and then Shepherd's slick fingers were probing at my entrance, massaging until I opened up for him.

I felt the blunt tip of the plug nudging against my tight hole, cold and unyielding compared to Shepherd's warm fingers. I breathed out slowly, trying to relax as he applied steady pressure until the widest part popped past my rim with a stretch and burn that made me gasp.

“Ah! Oh fuck...” I panted as Shepherd worked the thick silicone deeper, my body clenching and fluttering around the unforgiving intrusion. It felt huge, splitting me open, pressing against sensitive nerve endings I didn't even know I had.

“That's it, relax and take it,” Shepherd coaxed, his deep voice soothing even as his strong hands held me in place, preventing me from squirming away. “You're doing so well, Eli. Look at you, opening up so beautifully for me.”

His praise washed over me, making me feel warm and tingly all over, even as the plug's relentless pressure took my breath away. With one last firm push, I felt the wide base nestle snugly between my cheeks.

I was panting now, sweat beading on my skin as I adjusted to the foreign fullness. It felt so strange but so good, the weight and stretch igniting pleasure receptors deep inside me. The plug was pressed right up against a spot that made sparks go off behind my eyelids every time I clenched around it. My prostate, I realized distantly. Fuck.

I let out a shaky breath as I gingerly pushed myself upright, the plug shifting inside me with every movement. It was an insistent pressure, impossible to ignore, but not painful. Just... full. Stretching me in a way I'd never experienced before.

Shepherd stood back, his dark eyes gleaming with satisfaction as he took in my flushed cheeks and trembling limbs. “Good boy,” he praised, making me shiver. “Now, go start on your chores. I expect this house to be spotless by the time I'm done with some calls. And remember—no coming without permission.”

“Yes, Sir,” I managed, my voice already wrecked.

I wobbled out of the bedroom on unsteady legs, hyper aware of the thick silicone splitting me open with every step. It brushed against that magic spot inside me with even the slightest movement, sending sparks of intense pleasure zipping up my spine. My cock bobbed heavily between my legs, flushed an angry red and dripping steadily onto the hardwood floor as I made my way downstairs.

Dishes first, I decided. I filled the sink with hot, soapy water and scrubbed the pots and pans from breakfast, trying to ignore the plug's distracting fullness. It wasn't so bad, I reasoned. Weird and a little uncomfortable, sure, but nothing I couldn't handle.

As I rinsed a frying pan, the plug buzzed to life, making me yelp and drop it with a clatter.

“Oh fuck,” I gasped, gripping the sink as the vibrations sent shockwaves of pleasure through my core. It was unlike anything I'd ever felt—so direct and relentless against that sensitive bundle of nerves. My cock jerked and drooled a thick strand of pre-cum onto the floor as I clenched helplessly around the toy, trying to adjust to the intense new sensations.

I threw a wild-eyed glance over my shoulder to see Shepherd leaning against the kitchen doorway, a small remote in his hand and a wickedly amused glint in his dark eyes. He'd been watching me this whole time, I realized with a shiver.

“Something wrong, Eli?” he asked, toying with the remote. The vibrations intensified, and I bit back a whimper, my knees buckling as pleasure sparked white-hot through me. Shepherd's lips quirked into a small, satisfied smile as he watched me squirm and gasp. “Better get back to your chores then.”

With that, he turned and strode out of the kitchen, leaving me trembling and aching, the plug still buzzing away mercilessly inside me. I gritted my teeth and tried to finish the dishes, but it was nearly impossible to focus on anything but the relentless vibrations against my prostate and the throb of my neglected cock.

The buzzing didn’t let up until I was almost done with the dishes, and by then I was a panting, shaky mess. My cock was painfully hard and leaking a steady stream of pre-cum. I fought the urge to stroke myself to completion, recalling Shepherd's command. I wouldn't come without his permission.

I moved on to vacuuming next, figuring the noise would help drown out my desperate little whimpers. But as I bent over to plug in the machine, the plug buzzed back to life.

“Ah! Oh fuck, oh fuck,” I gasped, white-knuckling the vacuum handle as my vision nearly whited out from the intense pleasure. I gritted my teeth again and powered through, forcing myself to focus on the vacuum's monotonous back and forth. But it was a losing battle. The searing pleasure radiating from that secret spot inside me was inescapable, all-consuming. It built and built with every movement, every clench of my muscles around the thick silicone splitting me open.

Sweat dripped down my temples as I fought the urge to surrender to the ecstasy sparking through my nerves. My cock felt painfully hard, impossibly swollen and heavy as it bounced against my stomach with each step, smearing pre-cum in sticky threads across my tattooed skin.

Just when I thought I couldn't take anymore, teetering on the edge of orgasm, the vibrations suddenly cut off. I nearly crumpled to the floor, gasping for breath. My hole clenched desperately around the now still plug, trying instinctively to reignite that maddening pleasure.

A low chuckle from behind me made me whirl around, still panting. Shepherd leaned against the doorframe, remote in hand, a sadistic glint in his dark eyes as he took in the wrecked picture I made—naked, flushed, and aching for release.

“You're doing so well, Eli,” he praised. “Keep up the good work and maybe you’ll earn yourself a reward.”

I swallowed hard, Shepherd's praise and dark promise sending a shiver down my spine. “Yes, Sir. Thank you, Sir,” I managed, my voice coming out hoarse and shaky.

Shepherd gave me one last heated look, eyes dragging over my trembling, sweat-slicked body, before turning to leave. He paused in the doorway. “Remember, Eli—your safe word is Icarus. Use it if you need to stop or take a break at any point,” he reminded me, his deep voice serious.

I nodded jerkily. “I will, Sir. But I don't think I'll need it,” I added, injecting a note of stubbornness into my breathless voice. I was determined to prove I could take whatever he dished out. To be good for him.

Shepherd's lips quirked, something like pride gleaming in his eyes. “Carry on.” And with that, he was gone, leaving me to compose myself and refocus on my tasks.

I took a few deep, steadying breaths, trying to will my raging hard-on to die down a bit. But it was useless. The plug's presence was inescapable, a maddening fullness and pressure that kept me aching and on edge.

I gritted my teeth and forced myself to keep cleaning, trying to ignore the insistent throb of my cock and the maddening pressure of the plug stretching me open. The hardwood floors proved to be a special kind of torture - every time I bent over to scrub a stubborn spot, the plug would shift and press mercilessly against my prostate, making stars burst behind my eyelids.

By the time I finished mopping, my thighs were trembling and slick with sweat, my breath coming in harsh pants. I had never been so hard for so long in my life. My cock felt impossibly heavy, jutting out flushed and angry from my body, the piercing through the head glinting in the sunlight streaming through the windows. Every step, every movement sent a fresh jolt of painful pleasure zipping up my spine as the plug jostled inside me.

I moved on to dusting next, figuring I should tackle the mindless task while I could still see straight. The feather duster tickled my oversensitive skin as I flitted around the house, leaving goosebumps in its wake. I shivered, hyper aware of every silken brush against my feverish flesh.

As I was reaching up to dust the top of a bookshelf, the plug roared back to life, vibrations slamming into my prostate with a vengeance. A choked cry slipped past my gritted teeth as my knees nearly gave out from the sudden onslaught.

I clung to the bookshelf, white-knuckling the dark wood as the vibrations sent shockwaves of ecstasy ricocheting through my core. “Oh fuck, oh God,” I whimpered, my hips rocking back instinctively, grinding the buzzing toy deeper into my spasming hole. Tears of frustration and overwhelming pleasure pricked at the corners of my eyes as I fought against the urge to reach back and thrust the plug even harder against that magic spot inside me.

But I resisted, somehow finding the willpower to straighten up on trembling legs and keep dusting, even as the vibrations rattled me to my bones. Every movement was agony, the relentless stimulation making my vision blur and my breath come in ragged gasps. Dusty knickknacks slipped from my clumsy fingers as I stumbled through the living room, my coordination shot to hell.

Time lost all meaning, narrowing down to the maddening pressure of the plug stretching me wide and the searing pleasure sparking through my nerve endings with every subtle shift. Sweat dripped into my eyes and plastered my hair to my forehead as I fought to stay upright, to complete my tasks like a good boy. Like Shepherd's good boy.

The thought of my Dom, of earning his praise and approval, was the only thing that kept me going, even as my cock throbbed out a steady pulse of pre-cum and my balls drew up achingly tight.

But somehow, I managed. By lunchtime, I had my entire list of daily chores completed. When Shepherd came out of his office to make lunch, I threw myself at his feet, head bowed, body sweaty and trembling.

“Please, Sir,” I begged, my voice a hoarse rasp. “I did everything you asked. The house is clean, even though it was torture with this plug buzzing away in my ass the whole time.” I gazed up at him from beneath my lashes, eyes glassy with desperation. “I've been so good for you. Please, can we take the plug out now?”

Shepherd regarded me with a heated look, taking in my wrecked state with obvious satisfaction. “You have been very good, Eli,” he acknowledged, reaching down to card his fingers through my damp hair. I leaned into his touch with a shaky sigh, craving any scrap of contact. “I'm impressed by your obedience and self-control.”

Hope flared in my chest. Did that mean...?

But Shepherd's next words dashed my fragile optimism. “However, it's only lunchtime. I don't recall saying your plug torment would be done by now, do you?”

I bit back a whimper of dismay. He was right, damn him. “No, Sir,” I admitted miserably.

“That's right.” Shepherd traced the curve of my cheekbone almost tenderly before gripping my chin, forcing me to meet his eyes. “We had an agreement, Eli. You wear the plug all day. No coming until I allow it unless you want to use your safe word and I haven’t heard you say it yet.”

I swallowed hard, Shepherd's grip on my chin unyielding as he held my gaze. The intensity in his dark eyes made me shiver, even as desperation clawed at my insides.

“You're right, Sir. I'm sorry,” I managed, my voice coming out small and chastened. “I can keep going. I won't safe word unless I absolutely have to.”

Pride and approval gleamed in Shepherd's eyes at my words. “That's my good boy.”

His praise washed over me like a soothing balm, momentarily eclipsing the desperate ache throbbing through my body. I would do anything to hear those words from him, to know I'd pleased my Dom.

“Thank you, Sir,” I breathed. “I won't let you down.”

Shepherd smiled, a small but genuine quirk of his lips. “I know you won't. Now, go kneel by my chair while I make us some lunch.”

“Yes, Sir.”