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Demands on Him Ch. 02

By: latenightkiss



"Will, honey, will you make sure there's plenty of ice in the cooler?" Jenna called from the kitchen.

I checked my watch and saw that it was almost time for our guests to arrive. The New Year's Eve party had been Jenna's idea three years ago when we'd first moved in together, and it had evolved into a tradition. Jenna had spent the last two days cleaning and cooking in preparation for the party, and I had become her errand boy. I quickly checked the cooler of ice in the garage and came back in. I thought briefly about bringing the coolers into the mudroom, but decided against it.

The holidays had gone by without a hitch. We'd celebrated with Jenna's parents on Christmas Eve and sent them off the next morning to Jenna's brother's. Cindy and Jay were amazing people—I couldn't ask for betters, but I was glad to see them go. It was no coincidence that the lingering pain in my ass disappeared the same day they left. 

It had been over a week since I had seen my boss, Todd Barkley. The memory of that encounter hadn't faded at all in that time, despite my fervent wishing. Todd hadn't tried to contact me since that day, and I had taken all precautions to avoid him in public. I'd begun working out during peak hours at the gym, insuring that I would never be alone with my boss, should we be there at the same time.

After the ordeal in Todd's office, I had hoped that that would be the last we would see each other until after the New Year. Once the euphoria of the orgasm had worn off I remembered the office Christmas party that was supposed to be held that evening. The realization hit me just before Todd pushed the butt plug back into my raw and gaping hole.

"Gotta keep you nice and open for me, baby boy," Todd whispered. "There may not be time for foreplay later."

I shuddered hotly, and fought against the arousal raging through me. 

That night, as I got dressed for the party, I'd been sorely tempted to remove the plug, but I knew I'd be punished and it would only make things worse. 

At the party, Todd and I didn't cross paths for over an hour. I purposefully maneuvered myself and Jenna away from Todd as we mingled amongst my coworkers. After a couple of beers from the open bar, my vigilance slipped, and Todd managed to catch us.

"William, who is this beautiful goddess you have with you?" Todd asked with his confident charm.

"This is my fiancée, Jenna," I replied. "Jenna, my boss, Todd Barkley."

Todd and Jenna shook hands, and I suffered through small talk until we could make an escape. When I would have turned to leave, Todd clasped me on the shoulder and said to Jenna: "Forgive me, Jenna, but William and I need to discuss business for a moment."

Jenna nodded. "I understand. Find me when you're done, honey. I'm going to go talk to Brett and Sara." 

Before I could protest, Jenna headed off to talk to my office buddy and his wife. 

"Conference room," Todd murmured in my ear. He tugged on my elbow and, like a child, I followed, dreadful yearning boiling in my cock.

The room was dim, lit only by the lights coming from the surrounding area. The shades that provided privacy in the glass-walled room were shut, but still allowed glimmers of light to come through. As the conference room door closed, Todd smiled and said, "Your woman is very pretty. Does she let you in her ass?"

"Yes." I responded tightly. I wasn't sure if I feared was to come, or if I was looking forward to it. While my brain was conflicted, my cock twitched with anticipation.

The movement drew Todd's attention. "Looks like someone is eager for an encore." His smirk was visible even in the dim light of the room. "You've been avoiding me all night, sweet boy. It's time for you to pay for that."

I swallowed audibly, waiting for Todd to continue. Todd didn't speak, but began circling me like a vulture and his prey. The swat on my ass came swiftly and landed with a sharp sting that blossomed into heat. Another swat came down on the other side, and my channel clenched around the plug. I gasped a little, unable to help himself.

"That plug feels good, doesn't it baby boy?" Todd cooed, continuing to alternate swats across my muscular ass. Even through the fabric of my khakis, I could feel the pleasurable pain blooming across my ass.

I nodded, not trusting myself to speak. My moans were barely being contained, and I feared that opening my mouth would allow the collection to spill out into the room. 

"Strip, William." The order was stern and I obeyed without hesitation.

Once I was naked, I went to my knees without being told. Todd smiled at the obedience, but the position was not what he had in mind. This time the slap on my ass was one of punishment, and not of pleasure, and I yelped in response. 

"Lean over the table," Todd commanded, shoving me to my feet. 

Quickly, I headed to the conference room table. It was a sturdy mahogany table, one that was primarily used for lucrative pitches. The run-of-the-mill pitches usually happened in a more casual, but still nicely appointed, conference room a few floors down. I felt exposed as I pressed my chest to the cool wood; more so than I had felt kneeling in Todd's office. I fought to keep my breathing easy, my cock hard as stone, as I waited for what Todd would do next.

"Beautiful boy," Todd murmured, running his fingers over my quivering flesh. He could still see the lingering pink from the earlier spanking, the flesh there hot to the touch. "Spread that ass for me."

I clutched my ass cheeks and spread myself, the feeling of vulnerability escalating. 

"Baby boy takes his commands well. How does that plug feel in your tight ass, baby?" Todd asked as he pressed himself onto my back. 

I dimly noted that Todd was now naked as well, and wondered how I had missed my boss stripping. Despite what my head told me, I was longing to see my boss naked—wanted to gobble his cock and suck it hard until cum shot down my throat.

"It...feels good, sir."

I felt Todd's hand gliding over mine on my ass and groaned against the grain of the wood. Then the plug twisted in my ass, sending sparks of pleasure shooting across my body. My cock twitched again, and I knew that pre-cum was waiting on the head.

"I could keep at this all night, sweet baby," Todd clutched my cock and began to stroke, "but we don't want precious Jenna starting a search party for you."

At the mention of my fiancée, I should have bucked my boss off me and left the room, but instead, I moaned, loving the feel of Todd's firm hand gliding over my cock. Todd ground his cock between my open ass cheeks, nudging the plug still lodged in my ass.

"I'm going to fuck you now baby. I'm going to fuck you until you beg me to let you come."

"Yes sir," I whispered as Todd tugged the plug out of my ass. I'd grown so accustomed to it that I instantly felt bereft without it. 

"Look at that," Todd said in awe. "That perfect ass, just waiting for my cock. Hungry for it. Are you hungry for my cock, baby?"

I moaned, "Yes, sir."

"Want me to fuck you, baby?"

"Yes, sir."

"Yes, sir, what?"

"Yes, sir. I want you to fuck me. Please, just fuck me." 

Cool gel squished into my ass, but the chill did nothing to lessen my aching need. Then, Todd's cock was pushing into my ass, his work made easier by the plug that I had worn throughout the day. The pleasing burn followed the descent of Todd's cock until he was seated fully into my aching ass. Todd lingered, letting his big cock stuff me deep, and I let out a loud groan of pleasure.

Todd gave a short but powerful thrust and grunted into my ear. "Like that, don't ya, baby? I want to hear every moan you make, but not tonight. Say 'ah', baby."

The plug that, moments ago, been in my ass was shoved into my open mouth. My eyes widened at the taste of my own ass, and I tried to spit the toy out onto the table, but Todd held it firmly, refusing to let the plug leave my mouth. 

"Suck it, baby. Suck on that ass juice."

I whimpered and began to suck. Todd waited until he was certain that I would obey, and then relieved the pressure that he held on the toy. 

"Hold tight, baby. I won't be as gentle now as I was this morning."

 Gentle?  I thought dully,  I wonder what his definition of rough is.

Todd pulled all the way out, letting his cockhead rest against my spasming hole and then with a snap of his hips, drove himself deep, letting his balls smack against mine. Even with the plug muffling his sounds, Todd still heard my cry of pleasure, and my cock that he held in his hands twitched.

Todd moved his hands to grip my hips, the leverage allowing him to go deeper and harder and he thrust repeatedly into my welcoming channel. My moans came fast and deep, and I bumped my ass back, meeting Todd's punishing thrusts, my ass aching for Todd to go deeper, harder. My cock was aching for release, and I felt like I could come even without any direct contact on my cock, which was leaking pre-cum furiously.

"That's right, baby," Todd grunted. "Take it all."

Todd was nearing his climax, his balls drawing up tight. I could feel my own orgasm boiling in my balls, and as if Todd knew, he grabbed the base of my cock and squeezed, effectively stopping the orgasm I ached for. 

"Please," I mumbled around the butt plug.

"You'll come when I say," Todd said through bared teeth. I whimpered in response, and Todd continued to rut against me, his thrusts short and deep. Todd had one goal in mind: to come.

With a wild groan that could not be contained, Todd came violently, and I felt every hot spurt of cum as it landed deep in my ass. Todd lay across his back, his panting breaths steaming off of my skin. "That was good baby," he whispered, gently removing the toy from my mouth.

"Please, sir. I need to come, please," I begged as soon as the toy slipped free.

Todd didn't respond as he slid from my clutching depths. A lone droplet of cum escaped from my open ass before Todd once again shoved the toy back into my asshole. Thanks to Todd's thorough ravaging, I had to clench my cheeks together to help the toy remain in place. The motion didn't go unnoticed. 

"Looks like you'll need a bigger plug, won't you, sweet boy?"

I nodded. "Yes, sir."

Todd motioned to a chair. "Sit."

Bonelessly, I slid into the chair, my still-hard cock straining towards my belly button. "It's time for your reward, baby boy," Todd murmured, going to his knees.

I watched as my boss took my cock into his mouth for the second time, groaning at the sensation. Todd knew his away around a cock. Whether that was from giving head or getting head, I didn't care; I just didn't want him to stop. 

Of their own volition, my hips bumped against Todd's face. His boss's brown eyes cut to mine, and I feared briefly that Todd would stop, but instead of a warning lingering in those eyes, there was a shimmer of mischief. Todd re-doubled his efforts, deep-throating my seven inches. His fist joined in the mix, jacking the shaft as Todd mouthed the head. Todd gave a little tap to the plug's handle at the same time he sucked hard on the fleshy head, and without warning, I came hard into Todd's eager mouth.

My vision darkened as I tried to slow my breathing, and then Todd was in my face again, mashing our lips together. I gasped, and Todd sent a barrage of cum into my mouth as our tongues dueled. Todd's hand clutched at my neck, and I found my own hand tangling in Todd's hair as the cum-swap continued.

When the cum had been devoured between us, we drew apart, both breathing heavily. I thought weakly that I should be disgusted with myself, but was unable to care. The orgasm had left me boneless and sated, and my ass ached pleasurably. If Todd wanted, I would eagerly accept another fucking. I was acutely aware of my change of attitude in that moment, and I snapped to my senses.

I am a straight man. I love my fiancée. All this was was a fuck. Just a fuck. A fuck Jenna can never know about. 

The doorbell rang, snapping me out of my daydream. I quickly looked at my cock, thankful to see that I wasn't sporting a raging hard-on. Jenna called out for me to answer the door. Skirting around the coffee table, I called out "coming!"

My hand grasped the door's handle and I yanked it open with an excited "Happy New Year!" ready, but the exclamation died in my throat. 

"Happy New Year, sweet boy."

Demands on Him Ch. 03



I stared at my boss, dumbfounded by his presence on my doorstep. It had been more than a week since I'd seen him, and I certainly hadn't invited him to my house for tonight's party. The last thing I wanted was to ring in my New Year with the reason for all my hard-ons this week.

"Gonna let me in, baby boy?"

I stepped out onto the porch, closing the door behind me. "What the fuck are you doing here, Todd?"

He grinned wickedly. "And here I thought you had missed me while we've been apart. Your lovely fiancée invited me tonight, and I couldn't say no. That would have been rude." He stepped around me and opened the door. "Don't worry, baby boy, you'll get some alone time with me tonight."

He stepped inside and I heard him call out to Jenna over the roaring in my ears. As I followed Todd inside my house all the blood rushed from my head to my cock, despite my brain's objections. Fuck, this was going to be a long night.

----

People trickled into my house over the next hour, and Jenna had requested that I put all the coats on the bed back in our room. I was headed back there for the twelfth time in the hour when I felt a hand on the back of my neck. "About time I got you alone, baby boy."

The bedroom door closed behind us and I kept waiting to hear the click of the lock, but it never came. I held onto the coats in my hand, my grip tightening on the garments.

With a yank, Todd pulled the coats from my grasp and tossed them on the bed carelessly. With a firm hand on my back, Todd gave me the silent command to bend over. I lay with my chest on a pile of outerwear, my ass on easy display. I could feel Todd moving around, but couldn't see his movements.

"Take off your pants, William."

I hesitated, which earned me a slap on my ass. "Now, William."

With fumbling fingers, I undid the clasp of my jeans and shoved them down to my knees. Todd's hand landed on my ass in a firm spank, an action he repeated on the other side. "Such a nice ass you have, baby boy. I hope you've been keeping it prepared for me." I felt the dig of his fingers as he pulled my cheeks apart, exposing my ass. He made a tsk-ing noise as he used one finger to probe my hole. 

"Ah, William, you disappoint me. All my training at Christmas has been neglected." He slapped me again. Then again. I moaned.

"Don't worry, baby boy. I'll spank you some more. After. During."

Cool lube shot into my ass, followed by two of Todd's fingers. I groaned, praying that the guests in my house didn't hear me. The last thing I needed was Jenna to see me offering my ass to my boss on our bed.

I wanted to hate myself for letting Todd use me this way, but it felt so. damn. good.

"Please," I moaned.

Todd's fingers were gone, then replaced by something larger and firmed pressing against my hole.

"I didn't want o have to use this, but you've left me no choice, William. If you're good the rest of the night, then I'll fuck you."

His words made my cock twitch, made it grow impossible harder. I clenched my ass, hating the empty feeling.

"If you want this, I want to hear you beg. Beg me, baby boy."

"Please, Todd. Please shove that toy in my ass. I'll be a good boy, I promise. Please." My last words came out strangled, but I was rewarded with an insistent push against my aching hole. 

"Let me in, William."

I sighed gratefully and opened my ass so that the plug could slide home. It was bigger than the one he had used on me before, and it had knobs. As I grew accustomed to the pleasurable invader, a delectable buzz shot through me, nudging against that sweet button inside me. Craving more, I shook my ass, trying to coax the plug deeper inside me.

"Greedy tonight, aren't you, baby boy?"

I nodded, hoping that Todd would take mercy on me and just fuck me.

Instead, Todd pulled my pants back up and ordered me to fasten them. "If you can make it to the final countdown, I'll fuck you nice and hard to ring in the New Year."

My cock twitched again as I stood to look Todd in the eye. "Todd, I can't at the ball drop...Jenna—"

Todd pressed his finger against my lips. "I can make this night long and torturous for you without relief. Or, this can be a night of teasing that ends in a long, hard fuck. Your choice."

As he spoke, he gripped my ass with both hands. The vibrations in my ass kicked up a notch and I groaned, grinding my cock against Todd's through our jeans. I was certain that Todd wasn't affected until he pulled my mouth to his and devoured my lips. His tongue thrusting in my mouth the way I wish his cock would to my ass. He ground his erection against me as our tongues dueled for dominance.

With one last tongue-fuck, Todd pulled away, the buzzing in my ass slowed. "See you soon, baby boy," he said before walking out of the room.

---

The next few hours were a blur of drinks, laughs, and an aching buzz in my ass. Todd kept his distance after we left the bedroom, but kept me on edge by changing the setting on my vibrating butt plug.

The ball drop was coming up, a constant reminder of Todd's promise to fuck me into the New Year. Jenna was trashed, giggling with her best friend on the couch. I could only assume that Todd had been pushing drinks on her so that she wouldn't notice my absence when the countdown reached zero.

I caught Todd's wink just as the vibrations reached an all time high in my greedy ass. My phone buzzed in my pocket, a message from Todd on my screen.

 Make it through this, and I'll fuck you nice and hard til you cum, baby boy. 

I grinned with determination and covertly pressed a hard hand to my cock to stave off the orgasm that has been threatening me for hours. I could make it. I would.

I lost track of time, but eventually the vibrating stopped entirely. I stifled a whimper as Todd's hand clasped my neck. "I want you ass up on the bed, naked in three minutes. Go." Todd whispered hotly in my ear.

I shivered and nodded. I made a beeline for my bedroom. Absently noticing that Jenna was now passed out on the couch. I tossed my clothes in the corner of the room and climbed onto the bed, my ass clenching tightly around the now silent plug.

The door opened and shut quickly and then Todd was there, running his large hands over my ass. He slapped me with both hands, jiggling the plug deliciously. 

"Please, Todd," I whimpered. "You said you'd fuck me."

"I did, baby boy. You've been so good tonight. I'm going to fuck you nice and hard. But first, I need my toy back."

His fingers tugged on the handle of the plug, thrusting it into me with short, insistent jabs. The tip of the plug barely grazing that spot inside me. Then he slid the plug free and I could feel cold air brushing against my gaping hole.

"Look at that delicious pussy," Todd murmured. "I could eat it all night." Then he dove between my cheeks, his hands keeping my hole easily accessible. His tongue thrust inside my hungry chasm, eating me furiously.

Todd moaned into my ass and I couldn't stop my own moan. Todd's tongue felt amazing in my ass.

"That's right, baby boy. You love it when I eat your pussy, don't you?"

I whimpered and nodded.

"I want to hear you say it. Tell me how much you love it when I eat your pussy."

"I love it!" I shouted, desperate to get his tongue back in my ass. "Your tongue feels so good eating my pussy. Please eat my pussy."

Todd tsk-ed again. "God I love it when you beg. But I think it's time for you to eat my ass now."

I whined. Todd slapped my ass hard.

"You should be begging to eat my ass. You should be begging for the privilege." He slapped me again, heat blooming across my cheeks.

"Empty," I moaned. "Empty."

Todd pulled my hair until I could almost meet his gaze. "Do you need your ass filled, my greedy boy?"

He didn't wait for my answer, and there was immediately something pushing against my hole again. It felt larger than the vibrating plug, but it wasn't his cock either. Where was he getting all these toys?

"I found this in sweet Jenna's goody drawer. The pink plug looks so good in your tight pussy."

Jenna had this plug? I had never bought Jenna a pink toy, and I had never seen one before. My sweet Jenna was more of an ass slut than she had let on.

Guilt washed over me at the thought of my fiancée. I was enjoying Todd's attention too much to feel too guilty, however. My boss was quickly turning me into an ass slut too.

Todd shifted on the bed and then his ass was shoving against my face. "Eat my ass, baby boy."

I dug in, greedy for him. I ate at his ass the way he had munched on mine. He rewarded me with a moan of his own.

"That's it, baby boy. Shove that tongue in there. Eat my ass out."

I re-doubled my efforts. Determined to make him lose it. He was always the one making me beg, now I wanted to hear him beg.

I hadn't been at my task long when he pulled away. "Good job, baby. You've earned a nice reward. Get your face down and your ass up."

I obeyed eagerly, subtly shaking my ass for his attention.

"You're so greedy, baby. Here, take this present." He pulled Jenna's plug out of my ass and I caught a flash of pink before the plug was shoved into my mouth. I gagged against the intruder, and then relaxed my throat enough to suck on my fiancee's plug.

"That's my boy. Here comes your reward."

Todd rammed into my ass with one sure thrust. I briefly stopped sucking to scream. Todd stopped thrusting to shove the plug back into my noisy mouth.

"Shut up and take Daddy's cock like a good boy."

He resumed his fucking. Every stroke hitting that spot inside me that made me crazy. Every firm, even stroke brought me closer to the orgasm that had been teasing me all night long. 

He fucked me for what felt like hours, but it couldn't possibly have been. I dimly heard someone shout, "Thirty seconds!"

"Tell me how much you love Daddy's cock, baby boy," Todd ordered as he removed the plug from my mouth. 

The intensity of his thrusts amped up and I groaned raggedly. "I love your cock, Daddy. Fuck me with your big cock, Daddy. Please, Daddy."

"Whose boy are you?"

"Daddy's boy. Your boy."

"10...9...8..."

"That's right. Daddy's baby boy. Cum for me, baby."

"7...6..."

Todd's next stroke hit home and cum began to shoot out from the tip of my cock.

"5...4...3..."

Todd rutted harder, shoving his cock to new depths that made me gasp. He was getting close.

"2...1..."

"Happy New Year, baby boy." Todd grunted as cum began to shoot from his cock deep into my hungry ass.

He rested deep inside me for a brief moment before slipping out of my ass. I was empty. So empty.

"Clean my cock off, baby boy. We have a party to get back to."

I jumped at the chance to have his delectable dick back in my mouth. I swallowed it easily, my throat already opened from sucking on Jenna's dildo.

"Good boy," Todd murmured and I drooled over his junk.

He pulled away and I chased his cock as he laughed at me. "Now, now, sweet boy. I gotta clean you up so you can get back to your guests."

His tongue swept across my gaping hole. He repeated the action twice more and then reached from the pink plug again. With no preamble he shoved it back into my pussy. He had plugged his cum inside me.

"Get dressed baby," he commanded hotly. "It's time to say goodbye."

We went back into the living room separately. Jenna was still asleep on the couch, but had been joined by a few other guests who had over imbibed. Thank god über had just come to town so all my drunk guests could get home safely.

Todd was the only guest that remained an hour later. I returned from carrying Jenna to bed to find him sprawled across my couch. He looked like he belonged there, like he owned the place.

Well, he owned me and my ass, so I guess by proxy he owned my house.

"I had a nice time tonight, William," he said with a grin as he got off my couch. "You're a very...accommodating host."

He stepped up to me and cupped my face. "Does your pussy miss me, baby?"

"Yes."

"Yes, what?"

"Yes, Daddy."

He patted my cheek. "Good boy." He gave me a hard kiss. "Meet me tomorrow at the office at noon. We can really celebrate our New Year properly."

I nodded, already looking forward to our meeting.

"Keeping that pretty pussy filled until I take it out tomorrow. Disobeying my orders will earn you a punishment you don't want."

I nodded again, walking Todd to the door. He grabbed me again, gripping my ass tightly and covering my mouth with his. He shoved the plug deeper inside me until I whimpered.

"Gotta keep you eager, baby boy. Keep your hands off until I say so."

With that, he walked out the door, leaving me to a restless night.