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Author's Note: This story will be my submission into Kasarberang's non-con contest! I strongly encourage you to go to his original post to see the rules and get a better summary of the expected content of this story.  This is just the start of this story, but I hope to have it finished by the deadline for the contest, if not that, then the majority will be written in accordance with the guidelines.

This chapter will only have hints of what is to come, but it is very sexually graphic. Please take this as a warning to those who do not like that kind of thing. It will get worse. Heed all my tags as I will be tagging all the relevant things for this story all at once rather than as the story progresses. Please enjoy!

Boss Baby or Boss' Baby? : Chapter 1

“Here you go, Baby,” Miss Tammy said sweetly. Jesse blinked as his focus on his computer was broken and turned to Miss Tammy to see her holding a small plate with two donuts stacked on top. 

 

The workday had just started and he’d been sending out a few follow-up emails from the previous day when Miss Tammy approached. Seeing that she had his attention, she continued speaking. 

 

“I bought donuts for the office but I wanted to make sure you had some while they were still warm,” She smiled and set the plate down on the edge of his desk. “I also grabbed some milk for you.” She put the small bottle of milk right beside the plate. “Eat up!”

Jesse’s eyes lit up. He didn’t often have breakfast in the morning, but he’d devour anything given to him by Miss Tammy. 

 

Miss Tammy was the supervisor over the whole department. A woman of 35 (her birthday had just passed– They sang to her with cupcakes in the breakroom.) with a strict standard but soft heart. She could easily portray the tough boss aura, but that disappeared as soon as she slipped on her trademark black cardigan and red reading glasses. Said glasses were perched on top of her head, the stems hooked into locks of blonde hair tied in a bun so that they didn’t fall. She must have left her cardigan in her office, Jesse noted as he stood up to hug her in thanks. He was shorter than her on a good day, but now, with her wearing her standard black heels, she was tall enough to tuck his head under her chin and nearly inappropriately close to her bust. 

 

“Thank you, Miss Tammy!” Jesse smiled. “That was really sweet of you!”

“Oh hush,” She giggled, squeezing Jesse firmly before letting him go. “You know you’re my favorite.” The wink she followed the statement with had him returning the laugh. 

 

It was a running joke in the office that Jesse was her favorite employee because of the way she constantly doted on him. Jesse summed it up to being the youngest worker on the floor at just 21 years old. The next person older was Samantha at 25. It didn’t hurt that he leaned into the presumed special treatment by calling her ‘Miss Tammy’. The name was a bastardization of ‘Tammy’ the nickname the other supervisors called her, and ‘Miss Tamera’ the respectful title used by the rest of the floor. The first time he’d used it was an accident, but the resulting coo and sincere hug encouraged him to keep it up. 

 

“Oh! Before I forget,” She snapped, suddenly reminding herself of something. Jesse had since sat down at his desk and paused with half a bite of sugary glazed donut stuck in his mouth. “We are doing drug tests later on today starting after lunch.”

The words made Jesse’s stomach drop. “W-What?” He stuttered. 

 

Miss Tammy carried on as if she didn’t notice his hesitance. “You know how the janitors found weed stashed in the cleaning supplies closet?” She waited for his nod before speaking, leaning against the wall of his cubicle. “Well, I told John,” John Scott, who was her boss. “That none of my employees would ever bring something like that into the building. I even told him that it was probably one of the new janitors!” That led her to a laugh, head tossed back enough that she had to catch her red reading glasses before they fell from her head. 

 

“But he was insistent that everyone on the floor get drug tested. Even IT down the hall is getting it done,” She sighed. 

 

“Uh,” He wiped the crumbs from his lip, not feeling so hungry any longer. “What happens if someone…fails?” 

 

Miss Tammy’s face took on a sad look. “John says they’re getting fired, but if anyone on the floor tests positive, I’ll make my case for them. I love my team so far, I’d hate to see anyone go.”

“Yeah,” Jesse cleared his throat after his voice cracked, taking a sip of milk to rinse his mouth. “That would be bad…”

“Mhm,” Miss Tammy spared a distant look at him before coming back to her usual chipper self. “But keep that between us, okay, baby?” The pet name a joke just as his own for her. “It’s supposed to be a surprise.” 

 

“I will,” He assured, turning back to his computer. He nearly felt a bead of sweat drip down his forehead. “Thanks again for the donuts…”

It’ll be the last donuts he ever receives from her, he’s sure. 

 

It wasn’t that he was a smoker. He wasn’t! It was just…a stupid party. 

 

That weekend was his brother Travis’ birthday and they’d all taken a camping trip to celebrate. It was a great time with swimming at the lake, roasting marshmallows, and grilling hot dogs that Jesse…well. The blunts were passed around before he could even register it. One ended up in his hand…Travis said he didn’t have to, of course, but the cajoling of his (older than Jesse) friends pressured him into taking a drag. The smoke was awful! Jesse was wheezing and almost felt like he would throw up, much to the amusement of the crowd. 

 

When the next blunt came around, he told himself he’d pass it down. But Amber, the friend of Travis’ girlfriend, grabbed him by the chin and shotgunned the smoke in the pantomime of a kiss into his mouth. The hoots and hollers of the crowd spurred him on passed the lesser coughs that came from the lungful. The rest of the night was spent in the company of family and friends alike. And each puff after was like riding a bike. 

 

It was the first time Jesse had ever been high…and it was the best weekend of his life so far. 

 

But now…

 

He’d be fired!

Dread settled so deep in his stomach that he couldn’t work on anything as the office slowly filled with people. Two hours passed, only one more til lunch and then his fate would be sealed. Jesse’s hands were clammy with sweat. Should he just leave? Pretend he was sick and go? That would only delay the inevitable. And Miss Tammy would know he was lying! She’d seen him just this morning. 

 

No…He had to tell her before it was too late. Honesty was the key. He wasn’t the one who left the weed in the closet, of course. She would know that! She’d believe his story and she already said she was willing to plead his case to John. Newly emboldened, Jesse shot out of his chair and nearly tripped over his wastebasket on his way to Miss Tammy’s office. He felt the sweat on his face cooling at his quick movements and didn’t even stop to think about what his coworkers would think. 

 

A few quick knocks on the cracked door and he barely waited for the “Come in!” before slipping inside and shutting the door behind him. Miss Tammy sat at her desk, glasses perched low on her nose, and her eyes widened when she saw him.

“Jesse? Are you alright?” She asked with full concern and turned her full attention to him. “Sit! You look like you’re going to be sick.”

Jesse took the seat in front of her desk with slumped shoulders. “Miss Tammy I screwed up,” He said weakly. Tears rushed to his eyes as the events caught up with him. 

 

“Baby,” She said softly, her bracelet scratching lightly against the wooden desk as she leaned against it. “Talk to me, what has you all ruffled? Whatever it is, I’m sure it’s okay.”

“It’s not!” Jesse gasped. “I’m gonna fail the drug test.” At the admission, he slumped forward with his elbows on his knees and sobbed. “I smoked this weekend. I’m going to fail! I’m so sorry!” 

 

“Woah,” She kept her calm tone, the sound of her chair rolling back cut through the air. “Take a breath, baby.”

Her advice came soft as she walked around the desk. Jesse could see her bare feet where she’d taken off her heels in the privacy of her office. From the vantage point, he could also see a plastic wastebasket being positioned in front of him. If he finished those donuts, he most definitely would have been using it. A gentle hand rested between his shoulder blades and rubbed in circles soothingly. “Breath for me.”

The breaths came shaky, but they helped slow the tears dribbling from his eyes and making dark spots on her grey carpet. Fuck, he was a mess. “I’m sorry,” He whispered again. 

 

“Don’t worry, baby,” She said immediately. 

 

“I don’t want to get fired!” He looked up finally, casting his blurry vision onto her face, mere inches away from his from where she leaned over. “I- I don’t smoke- It was just one time!”

“I know,” She nodded. “I know you don’t smoke. You said it was a party. These things happen-”

“I’m so sorry-”

“I’m not angry with you,” She said for the first time in a firm tone, her brows furrowed and lips pursed. “I’m not, baby. I’m just worried you’ve worked yourself into this state.” 

 

Jesse’s lip quivered again and he watched her reach over her desk for a tissue. His hand reached up to receive it but was ignored in favor of her dabbing at his wet cheeks. His vision cleared up and to avoid meeting her analytic eyes, he stared ahead, only to flinch as he was rewarded with a view of her breasts. The seam of her bra was just visible in her hunched-over position. 

 

It felt like too long had passed before he realized he was looking down his boss’ blouse and his head jerked back up to look at her face, expecting disgust. But there was none. She was carefully mopping at his eyes to avoid poking him and pressed the tissue to his nose. “Blow.” 

 

Instinct took over and he blew into it, only feeling embarrassment at his own actions after she cleaned up his nose and tossed the tissue into the wastebasket. “Are you calm now?” She asked, positioning her hands on her knees and Jesse had to force himself not to peek back down at her cleavage. 

 

“Yes, Ma’am,” He nodded. 

 

“Good boy,” She purred. “Now come here.” 

 

Jesse found himself standing from his seat and being led around the desk to where Miss Tammy settled down in her own chair. He could see her heels tucked neatly under the desk and traced the path to her bare feet, up her shapely legs, to her her knees where her skirt was rucked almost too far up her thighs, and- Christ. At this angle he was able to see her breasts even better. The hem of her bra definitely peaking from the dip of her shirt now. Meeting her eyes, he blushed, seemingly caught. 

 

“You’ve been naughty this weekend,” She said with a sigh, one leg coming up to daintily cross over the other. “We have to figure out what to do about that.” 

 

Jesse frowned, worry creeping in. “I’m-”

“Uh uh!” She tsked. “I’m talking, you listen. Understood?” 

 

“Yes, Ma’am.” Jesse nodded immediately. 

 

“Good boy,” The praise lifted his heart from where it seemed to have fallen right to the basement. 

 

“So,” She continued. “You were very naughty this weekend. You told me you were going to your brother’s birthday party, correct?”

“Yes, Ma’am,” Jesse fought off the urge to elaborate. 

 

“And at this party you smoked weed,” Jesse’s eyes ducked to his feet guiltily. “And now I need to find a way to keep John from firing you.”

“...Yes, Ma’am.” 

 

“Well, it’s a good thing you’re my favorite. Isn’t it, baby?” She chuckled. 

 

Hopefully, Jesse met her eyes, seeing a mischievous look peeking up from the rim of her glasses. A few seconds passed and he realized she was waiting for an answer. 

 

“Yes, Ma’am.” He found himself meeting that look with a small smile. 

 

“Now,” She rotated slightly back and forth in her seat. “I know how to save your job…but about what you can do for me as repayment.” 

 

Jesse blinked in surprise. Seconds ago, it felt as though his job hung by a thread. But now here he was with the reassurance he’d keep his job. Only with the added mystery of suddenly being indebted to Miss Tammy. Never did she ask for repayment for things. Whenever he tried to pass her money for the treats and things she’d give him, she always refused. But…he reasoned, she was saving his job.

 

“I’ll do anything.” He swore. “Anything you want.” 

 

“Oh baby,” She laughed warmly. “You don’t want to tell me that.”

“But I do,” He assured, crouching down, hell, nearly kneeling at her feet just to look up into her eyes. “You’ve done so much for me. You didn’t even have to tell me about the drug tests but you did. And- And,” He stuttered. “You’ve always treated me nicely. I’ll do anything to repay you for saving my job.” 

 

Her lips pursed in thought. “Anything?”

“Yes! I’ll detail your car! Or pick up your dry cleaning! Hell, I’d scrub the floors of your house with my toothbrush if you asked me to,” He laughed at the image in his brain of him hunched fetal on what he imagined to be her kitchen floor. A flush overtook his face as he thought of her standing right in front of him. Towering and demanding as he worked hard to please her. 

 

“Take your pants off,” The words cut through his imagination. 

 

“What?” He asked, seeing her strict look once more on her face. 

 

“I said,” She spoke clearly but it might as well have been a yell in the quiet office. “Take. Your pants. Off.” 

 

Mouth suddenly dry, Jesse stood up. Was this really happening? It was a plot out of a bad porno, he was sure. He was dreaming! No way was his attractive boss demanding he take his pants off in response to her saving his job. 

 

“Well,” She quirked a brow and nodded to his belt. “Are you going to do it, or do I need to call John down here to start working on termination paperwork.” 

 

Jesse’s hands were on his belt the next second. His fingers shook as they fiddled with the loops and his cock already started to harden in his boxers. “M-Ma’am, Are we going to-” 

 

His question was halted as she suddenly shot forward and smacked his hands away from his belt. Her perfectly manicured fingers pulled at the belt until it dangled open. His pants slackened slightly on his hips. She didn’t stop there, unbuttoning his pants and sliding his fly down with ease. The pants pooled on the floor, his tented boxers left to hide his dick from his boss’ view. Her severe look didn’t change as she looked from his crotch to his face. 

 

Her legs uncrossed and her thighs parted. The skirt she wore rode higher on her thighs until he could almost see what color panties she wore. “Come here.”

Jesse didn’t need to be told twice as he stepped into the space left between her thighs. His cock brushed against her skirt and would have left a smear of pre-cum had it not already been soaked up by his boxers. Jesse ducked his head to meet her lips, but found himself suddenly knocked off balance and turning. His fall was caught by the hard wooden desk and a firm hand came to press down on his spine to keep him from getting back up. 

 

“T-Tamera?” He asked in confusion only to feel a sudden sting radiate from his backside that startled a yelp out of him. His knees went weak but his weight was supported by the desk and hand holding him to it. 

 

“What did you just call me?” He heard Miss Tammy’s voice seethe in his ear. 

 

“Tamera?” Another sting brought out a hiss of pain. “Fuck!”

Another SWAT. And he suddenly realized what was happening. He was being spanked!

“Don’t you swear at me, boy!” Miss Tammy scolded. “You come into my office and beg me to save your naughty ass, you don’t get to swear at me.”

“I’m sorry, Miss Tammy!” He gasped and yelped at another SWAT as it descended. The pain was fierce now. A sharp throb in his ass cheeks as she had been alternating which one she hit.

“You’ve lost that privilege to, naughty little boy!” 

 

“Please!” He gasped as three spanks rained on his ass. How a hand as gentle and small as hers could create such force, he wasn’t sure. “I’m sorry!” 

 

“Tell Mommy how sorry you are,” Miss Tammy sneered. “Tell Mommy!”

“I’m so sorry-” Three more spanks and Jesse felt his legs dance in place on the carpet. “Mommy!”

The word was startled out of him as quickly as the blows stopped. A whimper tumbled from his lips as he anticipated another that didn’t come. 

 

“Say it again,” Miss Tammy’s gentle voice came once more. “Tell Mommy how sorry you are for being a naughty boy.” 

 

“I’m so sorry, Mommy,” Jesse’s lip quivered and he found himself dangerously close to tears once more. Air brushed against his red-hot ass and he rushed to continue before the blow came. “I’m sorry for being a naughty boy, Mommy!” 

 

“That’s better,” She sighed and the firm hand on his back loosened. He didn’t dare move though. “You like being my good boy, yeah?”

“Yes, Mommy,” Jesse nodded, his hot face gaining relief from the cold surface of the desk. 

 

The hand on his back lifted and Jesse heard her sit back down. “Come here, baby.” 

 

Standing up and turning around, Jesse’s gaze dropped to Miss Tammy’s crotch. He had no idea when she’d taken her skirt off, but it lay on the floor near his pants. Her red lace panties were out on display for him to see. His eyes jumped from her pussy lips peaking from the thin fabric to her eyes staring at him intently. The red of her panties matched the red of her glasses, he realized. 

 

“Kneel right here for Mommy,” She pointed right between her legs and Jesse didn’t even register the burn of the carpet on his bare knees as he complied. This close, he could see where he slick was darkening the crotch of her panties. Could practically smell her arousal. His dick, having softened rapidly at the spanking, thickened up despite the residual throbs of his ass. 

 

“You took your punishment like a good little boy,” She commented and his eyes darted back up to see her smirking. Her thighs parted just a little more and her back bowed to push her hips closer to the edge of the chair. “Does baby like what he sees?” 

 

“Yes, Mommy,” Jesse nodded. Licking his lips. 

 

He could count on one hand the number of women he’d been with. And the things he did with them were mounting up to be laughably vanilla in comparison to this roleplay. He couldn’t say it wasn’t exciting even with how confusing it was. 

 

“Well,” She sighed and pushed her hips forward again. “Go on.” 

 

Needing no other invitation, Jesse found himself devouring the feast right in front of him. He pulled her panties to the side and with what he lacked in experience, he hoped he made up for in eagerness. Miss Tammy’s legs came to rest on his shoulders and her hand tangled in his hair. He didn’t know how long he ate her out, but he did so feverishly, chasing the slick from between her lips to the bud of her clit. Occasionally, he’d secure his lips in a suck around it, earning a sharp tug of his hair and an appreciative moan from Miss Tammy- Mommy. 

 

“Mommy’s gonna cum, baby,” She panted.

If possible, Jesse redoubled his efforts. Digging his tongue deep into her folds til his chin was covered in her taste, he couldn’t help a mirrored moan with her as she pulled him close through her trembling orgasm. Jesse didn’t stop until the hand in his hair was pulling him away from her twitching cunt instead of closer. Her knees trembled on his shoulders. 

 

Rocking his own hips forward, Jesse felt his cock was begging for attention in his boxers. But when his hand reached down from where it rested against the outside of Mommy’s- Miss Tammy’s thigh to stroke himself off, her hand tightened in his hair once more. 

 

“Did I give you permission to touch yourself?” She scolded breathlessly.

“N-No, Mommy,” Jesse whimpered, hand coming back to rest on her thigh. 

 

“That’s right,” She nodded and slowly slid her legs off his shoulder. She reached over and slid open her side desk drawer and pulled out a package of baby wipes. “Bring me my trashcan.” 

 

Slowly, Jesse stood up from his kneeled position and retrieved the wastebasket on the other side of the desk. Miss Tammy was using the baby wipes to wipe her pussy lips down and had since slipped her panties off. The panties remained in her hand when she tossed the wipes in the trash and she reached for his boxers. Thinking it was his turn to cum, Jesse helped her by shimmying them off, awkwardly pulling the fabric down past his shoes. He didn’t expect Miss Tammy to hold out her damp panties for him to step into, but when he looked into her eyes, she wasn’t bluffing. 

 

As he thought before, a seriously weird roleplay. But he couldn’t deny it was pretty hot. Before the panties were pulled up to his crotch, Jesse gasped as a cold wipe was pressed against his hard-on. 

 

“That’s it,” Miss Tammy smirked. “Shrink back down.”

It took a few cold wipes before his dick was soft once more, although the thrum of arousal was still present. She pulled her panties up his thigh, his dick actually fitting in the small pocket in the front, although the fabric slid up the crack of his ass uncomfortably. 

 

“Put your pants back on.” She demanded. 

 

Jesse turned around, receiving a playful swat to his aching backside, and grabbed his pants from the floor. 

 

Miss Tammy helped him button and zip his pants and secure his belt once more. “Those will stay on for the rest of the day and you will come to my home instead of yours after work, understood?”

“Yes, Ma’am,” Jesse spoke softly. 

 

“It’s Mommy whenever it’s just you and I,” She informed. “Understood?”

“Yes, Mommy,” Jesse corrected and watched her slip her skirt back on and rebutton her blouse to hide her bra- wait…had she done that on purpose?

“You’re free to return to work, baby,” She said in her usual professional tone. “Go on.” 

 

Jesse was stunned. That was it? Miss Tammy made a shooing motion with her hand and Jesse slowly shuffled to the door, the fabric of her panties digging into his skin teasingly. 

 

“See you tonight…Mommy,” He muttered and dipped out of the room. Taking a detour to the bathroom, not to take off the panties, but to fix his hair and wipe the cum from his lips. Just what did he get himself into? 

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Boss Baby or Boss' Baby? : Chapter 2

 

Jesse knocked on Miss Tammy’s front door nervously. Part of him expected that morning to be an elaborate dream. But the bite of Miss Tammy’s panties on his hips told him the truth. This was happening, and if he wanted to keep his job, he’d do anything Miss Tammy asked of him until she felt his debt was repaid. He supposed it wasn’t all bad. He didn’t get to cum that morning, but when this was all over, he’d have the spank bank of a lifetime to jerk off to. 

 

The door revealed Miss Tammy wearing little more than a short black nightgown. The sun was almost below the horizon and the door was far enough from the road that Jesse was less worried about her being seen and more occupied eyeing her breasts nearly spilling out the top of the nightgown. He could do that now, he told himself. He’d already eaten her out. 

 

“Baby,” She smiled. “You showed.”

“You told me to come here instead of home,” He said quietly, wondering if he was perhaps too eager in his obedience. 

 

She let out a delighted chuckle and stepped back. “Come on in.” 

 

Jesse stepped inside and heard the lock of the door click behind him. No turning back now. Not that he wanted to at least. 

 

“Come sit with Mommy on the couch,” She instructed, leading the way toward the living room. She looked different from the woman he often saw in the office. Her hair was out of its perfect bun, but now it was loose, hanging down to her shoulders. She wore no heels, but her hips still swayed with each step she took. Without pausing, she sat down on one end of the long couch and patted the seat beside her. 

 

Jesse sat down, now at eye level with the woman. She was leaning back against the couch, her knees together to protect her modesty, but she made no moves to pull down the nightgown as it inched up her thighs. “Do you like what you see, baby?” 

 

“I think you’re very pretty,” Jesse said honestly which provoked an amused smile from Miss Tammy. 

 

“Such a flatterer,” She said, toying with the hem of her nightgown between two fingers. “Is my baby excited for tonight?”

Jesse found himself nodding. “Uh,” He stuttered. “What are we doing tonight?” It wouldn’t hurt to get a general idea. “Are we gonna…you know…” 

 

“‘You know’ what?” Miss Tammy repeated. “Use your big boy words and ask for what you want.”

Face heating up to the shade of a tomato, he cleared his throat. “Are we going to have sex?”

“Would you like that, baby?”

Again, Jesse was nodding. “So…Uh…are we?” 

 

She didn’t answer, but her smile grew wider. Jesse watched as she pulled her feet up onto the couch and rested them on his lap casually. “I have some ideas of some things we can do tonight. But,” Her voice trailed off contemplatively. “I don’t think you’re prepared for that just yet.” 

 

Thinking she meant sex, Jesse’s brow furrowed. “I can handle it,” He insisted. “What we did in your office was a little strange, but I enjoyed it…mostly.” 

 

“Yeah?” She encouraged. “Even though I’m your boss?”

“I think that makes it better,” He says honestly. “Could you get into trouble for this?”
 

His heart dropped slightly as she nodded. “I could get fired. And you as well by association.” 

 

Fuck, he expected something like that. “I won’t tell anyone,” He promised. “I don’t want either of us to be fired.”

“You promise?” Miss Tammy asked, her foot brushing over his thigh, inching toward his crotch before tracing back down to his knee. “You’ll keep Mommy’s secret and I’ll keep yours? We can’t do anything else unless you promise me that.” 

 

“I promise, Mommy,” Jesse said as honestly as he could muster. “I want to have fun with you.” 

 

“Good,” She smiled sweetly and all at once, stood from the couch. “Close your eyes and come with me.” 

 

Jesse’s vision clouded with darkness as he complied. He felt her delicate hands (No not delicate. His tender ass knew better.) grab his wrists and begin to lead him down a hall. 

 

“Keep those eyes closed and Mommy will tell you the rules, okay?”

“Yes, Mommy,” He smiled. 

 

“Good boy,” They turned into a room, the door shutting and the sound of another lock clicking into place. “You’re going to do whatever Mommy says, okay? The second Mommy says it.” 

 

Easy enough. Following that got him this far. 

 

“And if you do so, I promise I’ll make you feel divine.” She purred. “Got it?”

Jesse nodded excitedly. “Yes, Mommy.” 

 

“If we start, there’s no stopping,” Her voice came seriously. “If you have any second thoughts, fess up and you can leave my house and we’ll pretend this never happened.”

That was a little worrying, he thought. But he really wanted to fuck her. “I want to keep going, Mommy.” 

 

She was quiet as her hands went to his pants once more. Jesse found himself divested of his clothes rather quickly before she rested her hands on his hips to more accurately guide him to stand somewhere. Her hands moved his back until they rested on a flat surface. “Climb up, baby.” 

 

He did so, surprised by how high the–table it felt like– was. Was she going to suck him off this way? The top of the table was covered in some sort of soft pad so that it didn’t hurt his sore butt. Her hands guided him to lay down and he did so with his legs dangling over the edge, although he could feel a small lip or shelf perhaps that propped his feet up. Was it a sex table? 

 

“Mommy’s gonna strap you in now,” She didn’t ask permission and Jesse felt something soft being clamped around his right wrist. The same with his left. And then his left leg. And then his right. Testing the (what he now knew was) restraints, he found they didn’t let him move more than an inch away from the table. His hands were strapped by his sides. He was stuck. At her mercy. 

 

“You can open your eyes now, baby,” She said and Jesse’s eyes snapped open. At first, all he saw was himself. Or rather, a reflection of himself. There was a mirror on the ceiling. A mirror where he could see himself naked and strapped down to a table covered in a white pad. Odd. 

 

Looking to the left, his jaw dropped. To his left was what looked like a bed encased in a cage. White bars came up the sides of the bed and above it with similar-looking restraints bolted to the sides of the bed frame. 

 

To his right sat a huge padded chair with what looked like a baby entertainment bar dangling down from an arch. Again, with similar restraints. Nearly every piece of furniture in the room had restraints on it! A rocking horse, A rocking chair, A playpen, and even a baby bouncer bolted into the ceiling! He was in a goddamn nursery! And adult adult-sized nursery!

 

“Does baby like his new room?” Miss Tammy cooed in a sickeningly sweet voice. 

 

New room? His confusion must have shown on his face as Miss Tammy chuckled. “We’re going to have so much fun together, baby.” 

 

The smile on her face grew a bit sinister. “You looked so pitiful crying to Mommy for help to pass a drug test you would have probably passed anyway!” She laughed. “A few puffs of a joint would be out of your system by now, my straight-laced little boy. But I’m thankful you didn’t know any better.” 

 

So his job would have been safe?! Why hadn’t she said anything?! And it was too late to back out now! Although, Jesse only slightly wished to take back his consent for these activities. This was a whole lot more than some simple roleplay, even if he thought Miss Tammy was unbelievably hot. He heard her open a drawer and tried to see what she was grabbing, but as he was positioned and strapped on the table, he couldn’t see into any of the drawers.

 

“Hmm…” Tammy hummed. Jesse opened his eyes that he hadn’t realized he closed to see her looking down at his pubic hair with a thoughtful look. “This needs to go…” 

 

“I can shave if you let me shower,” He said hopefully wanting to be released from the table. From the look he received, his plan was obvious. 

 

The solution Tammy came to was a strong-smelling cream smeared over all his bits. It was too uncomfortable for him to get hard on the situation, and he was quite glad when it was over. That done, he looked at his manhood in the mirror with shame. He was now completely in his birthday suit. Naked as the day he was born. The next thing that came was the chastity cage. It was heavy-duty rubber and it ensconced his dick and locked it away with a final sounding click. He’d never worn one before, but its mere presence made his unease for the rest of the night grow. 

 

“Mommy’s glad she got the small size and not the large,” Tammy smirked. 

 

Jesse bit his tongue to keep from making comments about being a grow-er, not a show-er. 

 

“It’s okay, baby,” She laughed. “You won’t need your little peepee while you’re with Mommy anyway.” 

 

“I thought we were going to…” He trailed off. “Are we not going to have sex?” 

 

She walked from her post by his feet and stood by his head to stroke his hair from his face. Her caring grin helped to settle the smallest portion of his anxiety. “Good boys get to have cummies,” Her hand trailed down his face to his chest until it rested on his locked-away dick. “It’ll be an adjustment for you, but I have the utmost faith that you’ll manage.” 

 

What Jesse never expected to happen next was a lubed-up finger reaching toward his asshole which caused him to suddenly flinch. Not that he could go far, anyway. “Oh!” Tammy giggled. “My baby’s never had anything inside his butt before, has he?” She asked and Jesse shook his head. 

 

“Don’t worry,” She cooed, and Jesse’s eyes screwed tightly shut as he felt the finger slowly enter. The lube aiding without pain. “Mommy’s got you.” He just seemed to get used to the feeling before another finger pushed alongside. 

 

“Fuck!” He hissed and a harsh swat stung his thigh. 

 

“Don’t swear at me!” She scolded. 

 

“I’m sorry, Mommy…” He stuttered, remembering the spanking that could be 10 times worse in his vulnerable position. 

 

The plug that was gently inserted in his bottom when he was adequately stretched felt strange. He’d never done anything like this ever. But the honest-to-god diaper that came out of the drawer was a quick distraction. 

 

“Don’t put me in diapers,” He whines in a moment of panic. “You have me in the cage, I have the plug, isn’t that enough?!” 

 

Tammy glared heatedly at him but said nothing. Her hand reached into a drawer again and Jesse jerked the single inch of slack he was given by the restraints to feel the plug inside him suddenly vibrate. 

 

“NO!” He cried out. “Stop it! Turn it off! Mommy, please! Turn it off!”

The thrum of it was foreign to him and his muscles clenched down onto the plug which seemed to make it worse. Every hard clench of his ass brought the vibrating plug right up against his prostate making his legs go jelly by reflex. The worst of it was the pressure he felt from his cock trying to get hard while locked in the cage. It just wasn’t going to happen.

 

“I’ll wear the diaper!” He gasped, feeling the vibrations stop immediately. His throat was rough and dry. “I’ll wear the diaper,” He repeated with a whimper. 

 

“There’s my good boy,” Tammy cooed. The diaper slid under his hips and was followed by a dusting of baby powder before it was taped up. Tammy couldn’t help her happy fussing over him. The threat of the vibrating plug was enough to keep him compliant long enough for her to dress him in booties and a t-shirt that said “Mommy’s Lil’ Stinker” on the front. “I bet my baby’s hungry, yeah?” 

 

Jesse, who was staring at himself in mortification in the mirror, cried out at the single-second vibration from the plug and turned his attention back to Tammy. 

 

“Hungry, baby?” She asked again. 

 

He was, actually. He didn’t eat anything on the way over from work so his last meal was a club sandwich and the remains of a stale donut at lunch. She nodded and slowly released him from his bonds. Her hand was latched firmly around a small black remote that he knew was connected to the plug in his ass should he need “correcting” again. “Give, Mommy your hand,” She took one of his mittened hands and led him to the kitchen. “You can only walk on your feet if Mommy’s holding your hand, understood?” She says. 

 

Jesse nodded and dropped to sit on the floor as soon as Tammy released his hand when they entered the kitchen. The plug inside him made itself known, but as long as he was still, it didn’t distract him too much. “That’s a good boy,” She praised. 

 

Jesse watched her go to the fridge to pull out two small bottles of something and pour it into a large baby bottle. From the counter, she added a small scoop of some sort of yellow powder. 

 

“I thought you were gonna make food,” Jesse said, feeling his stomach growl. 

 

Tammy gave him a patient look and reached out a hand for him to grab. “This will fill you right up.” 

 

They went to the couch next, Jesse sighing once more as he was maneuvered into a position to be cradled in her arms. His cheek was nearly level with her covered breast, but the nipple of the bottle was slipped into his mouth right after. The first drops were tasteless, but the following stream of liquid was mildly sweet. Not quite like chocolate milk, as the brown color of the bottle would suggest, but a good enough illusion that he found himself drinking down the whole bottle before he realized he was finished. The hunger in his stomach abated. Strange. 

 

When the bottle was empty, Jesse watched Miss Tammy set it on the side table. He expected an initiation of some sort. A kiss maybe. But Miss Tammy only turned the television on to some sort of Disney movie. She was more than content to hold him in her arms, cradled close to her chest, and watch the movie. Jesse, for lack of something better to do, found himself reaching up to curl a lock of the normally tied-up hair around his finger. 

 

She really was pretty. 

 

Her eyes dipped down from the screen to glance at him curiously. He couldn’t help the blush on his face nor the nervous shift that caused the diaper to crinkle loudly between his legs. “What’s wrong baby?”

“Nothin’,” He mumbled, leaning close to her bosom, the hand touching her hair dropped to play with the hem on the bodice of the nightgown. “Just think you’re really pretty.” 

 

“Awww,” She cooed, and it reminded Jesse so much of how women fawn over babies smiling in strollers. “Thank you, sweetie. That makes Mommy so happy to hear.” 

 

Thinking that was the end of it, Jesse returned his attention to her chest…It would be rude to just…grope. He was sure of it. Cuddling closer was one thing, she openly encouraged that. But this situation had turned from a hopeful booty call to a nearly domestic date night. Would it be appropriate for him to just…touch her? 

 

“Does baby want to see Mommy’s boobies?” Miss Tammy’s voice rang out causing Jesse to jerk his hand back from her shirt as if burned. “Don’t be shy…use your big boy words and ask Mommy for what you want.” 

 

Jesse spared a look up to Miss Tammy’s face, spotting her biting her lip with what he hoped was enthusiasm. “Can I touch you?” He muttered. 

 

“You’re already touching me, baby,” She teased, and the hand resting on his chest reached to cup the hand he had been touching her bodice with. Without hesitation, He opened his fingers and maneuvered his hand to cup her breast in his palm. “Don’t be shy.” 

 

He’d touched a girl’s tits before, but it wasn’t his boss. And nor was he dressed up like an infant. But…when in Rome. He felt the warmth of her through the thin fabric of her bra and nightgown. He made sure to be gentle even as his breathing picked up. A valiant effort to get hard came once more from his locked-up dick. ‘Good boys get cummies,’ she had said. How could he be a good boy? 

 

Well, she wasn’t shy with what she wanted, Jesse thought as he remembered the scene they did while in her office at work. As embarrassing as it was to think about, he was fairly confident he knew what to do to hopefully earn his orgasm. 

 

“Mommy,” He whimpered. Miss Tammy had her head tilted back against the back of the couch, her eyes shifted shut. But when he spoke they opened and she peered down at him through lidded eyes. 

 

“Yes, baby?” 

 

“Mommy, can I see your boobies?” 

 

A pleased smile grew over her face. “Of course you can, my good boy.” She leaned forward slightly to slip the spaghetti straps of her nightgown off her shoulders, letting it pool at her waist. It left her in a simple black bra. Her breasts were much bigger than he thought they’d be. Then again, maybe her work clothes just hid it well. A small twist of pleasure rang in Jesse’s stomach when Miss Tammy unclipped two clasps on the front of her bra. The front panel released and fell to pool at her waist with her nightgown. Her boobs nearly bounced as the support suddenly disappeared. Her nipples were already beaded up and standing at attention. 

 

“Mmm,” Jesse couldn’t help but moan, nearly diving to press gentle kisses to the newly exposed skin. His hands reached up to cup each breast. It was slightly awkward in the position he was in, but he didn’t wish to let go in favor of switching their position around. 

 

“Does my baby want to nurse?” She suggested softly, her back bowing away from the back of the couch to press her tits closer to the new attention. 

 

‘Don’t mind if I do’ Jesse thought before craning his neck up to take Mommy’s nipple into his mouth. Miss Tammy shivered in pleasure. “That’s it baby,” She purred. “Drink from Mommy.”

Jesse didn’t distinguish that from any other pillow talk. At least, not until a slightly sweet flavor started to coat his tongue. His brow furrowed, but before he could pull away from the offered nipple, Tammy’s hand that was supporting his neck was now fisted in the back of his hair, holding him in place. 

 

“Mmph,” He grunted, trying hard not to press his teeth against her sensitive skin. “M’mmy?”

“Come on, baby,” She huffed. “Nurse from Mommy.” 

 

Her left hand reached down to cup the front of his diaper. His cock was still locked away, but the slightest friction was nearly too much for him to bare. Hips twitching eagerly, Jesse decided to disregard his concerns and continue nursing. 

 

“That’s it,” She praised, her hand in his hair relaxing as he stopped trying to pull away. “Drink Mommy’s milk.” Her head tilted back against the back of the couch once more. 

 

To Jesse’s astonishment, he realized that was exactly what was happening. The sweet flavor coating his tastebuds was some kind of milk coming from his hesitant suckles on her nipple. Was he actually doing this? He couldn’t believe it. 

 

Lactation was never something he put on his list of turn-ons. It was slightly strange in the same way him wearing the diaper and booties was. But the results were obvious. He could feel Mommy’s thighs rubbing together, no doubt trying to get friction, right behind him. Her breathing was quicker and he could feel the thrum of her heartbeat along his lips. 

 

His own arousal was nearly frantic under his skin. If he were alone, he’d already had his cock in his hand, stroking himself to a quick finish. But the cage and Mommy’s barely-there petting to the front of his diaper was an immense tease. 

 

“M’mmy,” He whimpered against her skin. “M’mmy, mph!” 

 

His quest for more relief was interrupted by a growing need to piss settling into his bladder. Mommy paid no heed or care to his sudden wide-eyed plight. She was thoroughly absorbed in his nursing. A bead of sweat trickled down his temple. He needed to make her cum quicky so that she could take this damn diaper off him. 

 

Pulling himself up, he adjusted until he was halfway kneeling over her lap. He lost the friction of her hand but consoled himself with rutting slowly against her thigh. The next clench of tension from his bladder put him back on track and he reached under the fabric of her nightgown to touch her dripping wet pussy. No fucking panties this time. He nearly growled. She was planning this from the start. 

 

He started with one finger curled deep into her slick heat, his thumb tracing over her clit to the response of jerked pleasure. 

 

“Fuck, baby!” She cried out in surprise. “That’s it-” 

 

He slipped another finger inside her, fingering them in and out, nearly pinching her clit between the frantic fingers. 

 

Despite the hand holding him tight to her breast, he pulled away to latch onto the other, a few suckles were needed until the delicious milk started to flow from that one too. She cried out, yanking on his hair in surprise. Her orgasm wracked over her like a tidal wave. Jesse would have been proud of himself if he didn’t feel his body trembling with the effort not to piss himself. If he were standing, he’d 100% be doing the potty dance. 

 

“Mommy, please,” He whimpered with the space he was able to pry away from her dripping tit. A cramp seized in his stomach. “Mommy!” 

 

Still coming down from her high, Tammy gave a satisfied smirk. “That’s a good boy. Making Mommy feel so good.”

Any other moment, he’d adore the praise. But all he felt was horror as he hand reached to the side table where the empty bottle and black remote sat. “No! No! No! Don’t-” 

 

The vibrator kicked to life and Jesse felt as though he screamed. Each pulse of vibration shuddered deep inside and against his taint, sending insistent pulses up his cock and into his bladder. It was as though an orgasm was being ripped from him by force. Part of him completely forgot his need to piss as he, instead, fell back onto the couch. His body was no longer able to support him. 

 

“I think this sweet boy deserves a treat for making Mommy feel so good,” Tammy purred, her hand reaching back to paw at the front of his diaper where he was locked away. “Oh?” She said in delighted surprise. “Aww, you’re dribbling.” She cooed. “Good thing I put my little boy in diapers or else he’d have made a mess everywhere.”

Was he pissing? Jesse didn’t know. He felt simultaneously too hot and too cold. Each pulse of what he thought was an orgasm caused his hips to rut up into Tammy’s hand. 

 

“Please let me cum,” Jesse begged for mercy. “Let me cum. I need it-I’m- I’m ready!”

 

“Is baby asking for cummies?” She teased as if she didn’t understand. 

 

“C-Cummies-” He choked out before his mouth was wide open in a soundless scream. His tongue lolled out from his lips as his eyes rolled back. A line of drool escaped Jesse’s mouth, tracing down his chin. His destruction started with his legs. Trembling and struggling to stay still, his thighs flexed as if to protect his most delicate bits from the onslaught. But the diaper and Tammy’s hands kept him wide open and accepting. Even pressing small pats to his ass, making the plug shift a little harder with the clench of his muscles. 

 

His cock twitched hard, once, twice, thrice. He couldn’t even tell if he was shooting cum or not with the diaper on. Each spasm seemed to tear him apart more than the last until he felt the first stream of piss escape. Jesse slumped like a puppet with its strings cut. The intense vibrators seemed to stimulate his bladder as with each twitch of his cock, a stream of piss pulsed out. His diaper soaked it up eagerly until there was so much, it started to dribble down his ass crack to soak into the back of the diaper instead. 

 

“Mommy-” Jesse gasped out with each body-wracking spurt. Most words had escaped him. Even as his flow tapered off he seemed trapped in the throes of pleasure. The vibrations continued for another sick moment of torture before they finally halted. 

 

“There’s my baby,” Tammy cooed, leaning over Jesse’s wrecked body to kiss his sweat-soaked brow. 

 

A whimpering cry rang out in Jesse’s ear and he didn’t even realize it was him until the cold feeling of tears dripping from his eyes struck his heated skin. 

 

“Oh, babe,” She said softly, pulling Jesse up into a hug, her naked breasts pressing against his chin and chest. “What’s wrong? Didn’t that feel good? Didn’t you like making cummies for Mommy?” 

 

“C-Cummies,” He sniffled hard. Not able to gather the words to explain his distraught feelings. He wasn’t even sure he knew what was wrong at all. 

 

“Mhm,” Tammy agreed. “Good babies get cummies. And you were very very good for Mommy.” 

 

“Mommy,” He reached up, wrapping trembling arms around her to return the hug. 

 

“You tell Mommy when you feel better and we can go get your diaper changed, okay?” She assured softly, pulling him until he was lying over her, snuggled close to her bare chest. 

 

“Mommy,” He sniffled, nuzzling her chest like a needy cat.

 

“Mommy’s here, baby,” She hummed. “Mommy’s here.” 

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Boss Baby or Boss' Baby: Chapter 3

 

Jesse was unaware of how much time passed before he felt like himself again. Eventually, though, his diaper started to grow cold and uncomfortable. Every shift would cause the plug inside him to shift as well and it left him feeling wrung out and very overstimulated.

“Mommy,” He whispered, surprised almost immediately as that was the first title that came to his mind. Not ‘Miss Tammy’ or anything else. “Mommy, can we go get cleaned up?” 

 

“Does my boy want his diaper changed?” She asked, scratching her nails gently against his scalp causing goosebumps to rise along his arms. 

 

Perhaps he wasn’t feeling 100% like himself again as he melted against Tammy’s chest once more and hummed. “Mhm, want my diaper changed, Mommy.” 

 

“Good boy,” She purred. It was her gentle guidance that led him to stand up from the couch and awkwardly waddle to follow her down the hall in his soaked diaper. He needed no extra instructions as he climbed up onto the table again, sparing a small look at himself in the mirror. He looked pathetic. His skin was still slightly red, his hair disheveled, and an obviously soaked diaper strapped to his waist. 

 

“Do I need to strap you down again or can you be my good boy?” She asked with her hands on her hips. She’d discarded her bra somewhere along the way and he could see her perked nipples through the thin fabric of the nightgown. 

 

“I’ll be good,” Jesse assured quietly. 

 

He watched from his reflection as she untapped the diaper with expert hands. When the front panel was pulled down, he was embarrassed to see milky streaks of cum dirtying his still-caged dick and the inside of his diaper, the white splashes stark against the slightly yellow-tinged material. 

 

“Aw,” Mommy cooed, stroking her finger over the tip of his penis, chuckling at his oversensitive flinch. “You came so much! Poor baby must have needed his cummies, hm?”

Immediately he knew she wanted an answer. 

 

“Yes, Mommy.”

“And what should a good boy say now that he’s had his cummies? Mommy made you feel so good…” She asked, reaching into the drawer for a package of wipes. 

 

“...Thank you, Mommy.” 

 

“For?”

Oh god. He looked away from his reflection to stare off at the crib. Is that where he was going to be sleeping tonight? “Thank you for the cummies…”
 

Mommy’s face lit up. “You’re very welcome, baby. Mommy loves rewarding her good boy. But Mommy also isn’t afraid to punish bad boys either.” 

 

Jesse knew that much. The spanking at the office was no joke! 

 

They were silent (although Mommy was humming under her breath) as Jesse’s cock was released from the cage and his privates were wiped free of baby powder and the used diaper was disposed of. When the plug was finally removed, Jesse couldn’t help the weak whimper that escaped him. For an awkward moment, his ass clenched down on nothing. It didn’t help that Mommy was watching it all with a smile on her face. 

 

“Don’t worry, baby,” She soothed, petting his thigh. “I have plenty of toys for you to try.”

“I’ve never-” Jesse trailed off. 

 

“I know,” Mommy nodded. “We’ll start slow. But eventually, you’ll love having your little ass played with while you make cummies.” 

 

Before Jesse could comment on that bombshell, another cage was retrieved from the drawer. This one was a softer silicone and much less noticeable after it was locked on. 

 

“Hmm,” Mommy pondered, looking into the drawer. “What diapers does Mommy want to put on her little stinker?”

Confusion steeped in Jesse’s mind before he realized she was calling back to the writing on his shirt. She seemed to decide without his input and Jesse found himself being diapered up in a much thicker, blue-patterned diaper. 

 

“Is this going to be a thing?” He couldn’t help but ask while he was guided to sit up. “The diapers and baby stuff?” 

 

“Oh definitely,” Tammy smirked. “While you’re my little boy you will never be out of diapers. Even at work.”

Jesse’s eyes widened. “I can’t wear these to work-”

“Ah ah ah!” Tammy tutted. “You’ll wear what I tell you to wear. If you’re a good boy I have more discrete diapers for you. But I won’t hesitate to send you on the office floor in one of these, little boy!” She pointed to the diaper he was currently wearing. 

 

“Anything else?” He asked sarcastically with a morose tone. 

 

“You are my baby,” She reinforced. “I reward my baby when he’s a good boy. I punish him when he’s bad. If you want something from Mommy, you ask for it.” 

 

No way that can come bite him on the ass, he thought sarcastically. “Yes, Mommy.” He responded. 

 

It only took ten more minutes before he was secured in the crib with a pacifier clipped to his shirt and a baby bottle of water left by the pillows for him. He had to admit…at least the mattress was comfy. At his insistence that he wasn’t hungry, Tammy nodded and set about readying a pump right in front of him. 

 

“Do you just…do that?” He couldn’t help but ask. 

 

“It’s somewhat new,” Tammy admitted. “I wanted to be able to feed my baby. Did it taste good?”

Looking back, Jesse could admit it did taste pretty good. Relaying the information caused her to smile and he watched her bag up two packets of breast milk to place in the fridge in the kitchen. With instructions to call her if he needed anything (and informed of the presence of a video baby monitor on the shelf pointed at his crib), Jesse was left to sleep. Unbelievable. How did he possibly get himself into this situation? 

 

Sleep found him reluctantly as half the bottle of water was sipped before he finally drifted off. It seemed as though he was only asleep for a few minutes before a sweet sing-song voice was calling him out of his rest. 

 

He groaned, rolling over and reaching out to silence what he thought was the alarm on his phone. 

 

“Aww,” Tammy’s voice cooed at him. “I know, baby. But you have to grab work clothes from home before your shift.”

Cracking his eyes open, Jesse spotted the white bars of the cage he was in above him. The soft sheets wrapped around him tried to lull him back to bed, but Tammy wouldn’t have that. The side of the crib slid down with a few clicks and Tammy was free to reach her arms in to cradle him close. Jesse was very foreign to the concept of waking up with someone near him, but he decided he could get used to it as he nuzzled his cheek against Tammy’s shoulder. 

 

“Let’s see how dry you are,” She mused, her hand tracing down his chest to part his thighs. The diaper taped onto his hips crinkled loudly as she groped over the front of it. A throb of interest from his dick reminded him of its locked-up status and he sighed.  “Mommy,” He mumbled, receiving a pleased hum in response. “Cummies?”

Tammy’s eyes lit up. “I would love to help you with that, baby,” And Jesse felt excitement well up in his chest before it was dashed. “But,” Her finger gently tapped against his nose. “We don’t have time for that this morning. Besides, you’re still dry.” 

 

Her hand patted the front of his thick diaper as if to prove her point. “Please?” He asked with what he hoped was puppy eyes and tried to reach down to grope himself even through the diaper. His hands were grabbed into a firm grip. 

 

“Does baby need a spanking this early in the morning?” Tammy asked with a raised eyebrow. 

 

Jesse let out a deep whine, hands dropping to fist into the sheets instead. “No, Mommy.” 

 

“That’s what I thought,” She nodded. “Now, are you hungry?” 

 

Jesse wasn’t one for breakfast, but the way Tammy was reaching for her nightgown again had him quickly reconsidering. His head bobbed in a nod and his tongue traced over his lips in anticipation. 

 

“Ask nicely, baby,” Tammy urged. “Ask Mommy for what you want.” 

 

This again. Jesse mentally sighed. “Mommy,” He asked as sweetly as he could. “Can I nurse?”

It sounded so foolish to his brain to say those words. He was sure his face was burning bright with a blush. But the look on Tammy’s face was worth it. “Of course, sweet boy!” 

 

Jesse couldn’t help but think derisively about how there was enough time for him to nurse, but not enough time for him to cum? Sure. Tammy led him over to the rocking chair and pulled him into her lap excitedly. He thought that it would have been an awkward fit for him, a grown man, to sit in her lap on the chair, but it seemed as though that was compensated with the design of the chair. 

 

Tammy was able to rest the arm cradling his head to her breast on the arm of the chair and his knees were resting comfortably over the other padded arm. Her nightgown slipped down with ease and the nursing bra was nowhere to be seen. It was far more awkward to nurse without the haze of arousal clouding his brain, but in a way, he was better able to enjoy it. The gentle scratch of Tammy petting his hair. The soothing rock of the chair. The warmth of Tammy’s breast in his mouth. 

 

Jesse hadn’t realized his eyes were closed until Tammy’s thumb parted his lips from her nipple. His eyes fluttered open. He couldn’t help but be slightly disappointed that it was over. 

 

“Let’s switch to the other one, babe,” She reassured, adjusting just slightly so he could latch onto the other one. Maybe this wasn’t so bad…

______________

 

After letting him drain her dry, Jesse was ‘allowed’ to go home, but not before showering and being diapered up in a (thankfully) thinner diaper that wasn’t obvious under his work pants. By Tammy’s instruction, he packed a bag with some extra work clothes so that he could spend the night and sleep in at her home instead of waking up early.

By the time he walked into the office, it was almost as if nothing had happened. Only the crinkle of his diaper as he sat down at his desk reminded him of it all. He got sucked into the flow of work and didn’t realize the first issue of the cage until his bladder twinged at him right before lunch. 

 

‘Can you take this cage off so I can go to the bathroom?’ He texted her. 

 

‘Come see me in my office.’ Was the message he received in response. Great…

 

He knocked on her door and stepped inside to see her eating a bowl of salad at her desk. 

 

“Lock my door, Baby,” She instructed, barely looking up from her computer screen. 

 

Doing as he was told, Jesse found himself standing awkwardly in front of Tammy’s desk, her lack of attention on him a big difference from the usual care directed toward him. Each crunch of her salad made Jesse shuffle his feet. Was he supposed to wait to be acknowledged? Did he need to ask again? He wasn’t sure what he was supposed to be doing. 

 

Seeming to find a stopping place, Tammy hit a key on her keyboard to pause whatever video she’d been watching with her meal. Her eyes turned to him and Jesse smiled sweetly. Returning the smile, Tammy pushed her salad aside. 

 

“Are you on lunch now, Baby?” She asked, lacing her fingers together and leaning her chin on them casually. 

 

“I was about to clock out…” Jesse informed shyly, suddenly needing to look down at his feet to avoid her gaze. “But I wanted to go to the bathroom first.” 

 

“Oh?” She hummed. Her chair was pushed back slowly. “And did you?”

Jesse shook his head. “I…I wanted to ask you to take the cage off first…”

“Why would I do that?” Tammy tilted her head to the side and looked Jesse up and down. 

 

“...So I can go?”

Tammy let out a sigh that made Jesse feel like he’d broken some sort of rule and now she was begrudgingly punishing him. The feeling didn’t dissipate as she waved him over to her side of the desk and pointed at the spot right in front of her. Oh god. When Jesse’s feet planted in front of her, Tammy’s hands started to unbuckle his belt with ease. It was so familiar to the previous day that Jesse couldn’t help but hope for a similar experience. Maybe he’d finally get to cum?

His pants button was opened and the front of the diaper was exposed. It wasn’t overly cutesy like the previous ones were. Just a plain white plastic front panel. The only color was blue lines on the tapes. “Still dry,” Tammy said with a strong tone of disappointment. “Why is that, Baby?” 

 

“I…” Jesse thought the answer was obvious. But some survival instinct inside of him told him that it was not the correct answer. “I don’t know.”

Tammy’s disappointment seemed to grow. “You don’t know.” Tammy turned, reaching for a drawer at her desk and pulling it open. In his standing position, Jesse could see stacks of diapers both thin and thick as well as changing supplies inside. “What do you see in here?”

“...Diapers?” Jesse answered, expecting to be wrong. 

 

“And why would I have diapers in my desk, Jesse?”

Jesse’s heart dropped. He must be in so much trouble for her to use his real name. How was he going to get out of this? How could he fix this? “To…” He paused, biting his lip. “To change me?”

“Correct,” Tammy nodded and reached into the desk to pull out a pink printed diaper with little rabbits on it. It landed on the top of her desk with a loud thwap. “And why would I need to change you?”

“Because…” Jesse felt his lip quiver. Why? Why was the scrutiny of Tammy so much for him to bear? Why was he so worried that she was angry with him? “Because I-”

Tammy didn’t offer any assistance as Jesse’s voice cracked. “Because I needed it?” 

 

Tammy said nothing as she pulled out an opened pack of wipes and a small bottle of baby powder and set them on the desk as well. The last thing was a white plastic pad folded up that she spread onto the ground beside Jesse’s feet. “You had no problems wetting your diapers last night, little boy.” She said sternly. “Maybe I spoiled you too much by letting you make cummies so soon.”

“No!” Jesse denied it immediately. “I’m sorry, Mommy! I- I didn’t know you wanted me to- to use my diapers at work.” 

 

Jesse dropped down to his knees at her feet, hands twitching to rest against her legs but wasn’t sure if he was allowed. “I’ll be a good boy. I promise. I’m sorry. Don’t be mad at me, please Mommy.” 

 

The stern crease between her eyebrows smoothed out slowly at his groveling before she gave a long. “I suppose I can give you a little slack since you’re still new to being my baby.” She said, reaching up to pet his hair. He leaned into the touch eagerly, plastering his cheek to her knee. 

 

“Thank you, Mommy,” Jesse said honestly. “I promise I’ll be a good boy.”

“Well then,” She said, tilting her foot forward to pat his padded crotch. “Go on then. Go potty for Mommy in your diaper.” 

 

Jesse’s heart raced, but in the end, he knew there was no resisting. It was hard to let his muscles relax. It took a lot of hard concentration and imagining himself in front of the urinal. His eyes squeezed shut at the first trickle. The second came much easier and lasted for a few seconds before dribbling to a stop. But once he started, Jesse found he couldn’t stop. It was like a building pressure in his bladder. Each spurt was a tease until he was pressed, lips parted, against Tammy’s knee. The stream was steady then and he felt a surge of warmth spreading through the front of his diaper. It didn’t seem like the diaper could hold it all. The warmth trickled down his scrotum until it reached his crack and started to pool there.

 

He could feel the warmth radiating from his diaper as it eagerly soaked up all it could manage. At last, the flow tapered off for good and Jesse was left nearly mewling and panting against Tammy’s leg. The quiver of his lip was back and wetness flooded his eyes. He couldn’t see her face through the blur of his tears, but he hoped it was happy. 

 

“M-Mommy I-I-” He stuttered with a sniffle. 

 

“Aww,” She cooed. “Did baby go potty in his diaper?”

“Mhm,” Jesse hummed sobbing as Tammy’s hand grew firm in his hair.

“Say it, baby,” She reminded. “You know Mommy loves to hear you say it.” 

 

“I went potty,” He cried out, hoping the office was soundproof. “I went potty in my diaper, Mommy.”

“That’s my good boy,” Her smile was evident in her voice and she lightly pushed him away from her leg toward where the pad lay on the ground. “Let’s get my baby changed so he can have some lunch.” 

 

Jesse’s cries turned to weak whines as he was laid out onto the changing pad. Tammy let out soothing noises the entire time she transferred the supplies to the floor and dragged her purse over. Between one moment and the next, Jesse’s wet diaper was removed as well as his cage and he was thoroughly wiped down. Any relief he would have felt at the cage being removed was clouded by the surprise that arose as something small and round (But not like the plug from before) was slipped into his backside. It was so small that there was almost no resistance to its movements. And happened so quickly that he couldn’t react. A blink and suddenly he was generously powdered and changed into the noticeably thicker pink diaper. 

 

“You are not allowed cummies,” Tammy’s words were firm. “Mommy is trusting you to be a big boy and not make a mess in your diaper. You won’t like the consequences if Mommy finds out you disobeyed.”

Jesse sniffled. “Yes, Mommy,” Was all he could manage to say before Tammy pulled his pants back up and did his belt for him. There was a small moment of pause as she fiddled with the back of his belt buckle strangely, but Jesse thought nothing of it. He was more focused on trying to ignore how thick this new diaper was. He hoped with his black slacks it wouldn’t be noticeable. 

 

“Now, is my boy hungry?”

‘Lunch’ turned out to be another feeding from Tammy’s breasts. It wasn’t quite as filling as he hoped, but Tammy came prepared with a small water bottle half filled with water and a capsule filled with more of that yellow powder. “What is that, Mommy?” He asked softly as she shook the two together, her breasts jiggled with the movement where they were tucked into her bra but her shirt was left open. 

 

“It’s a protein blend, baby,” She explained patiently. “Mommy doesn’t make enough milk yet to feed you, but this will help keep you full while Mommy’s milk catches up.” 

 

Jesse didn’t ask any more questions as he accepted the bottle and a wipe for his face before heading for the door. He made it back to his desk without bumping into anyone as they were all still at lunch. He had about ten minutes left of his lunch that he used to chug the formulated mixture and put the empty bottle into his bag to take to Tammy’s house later. It was when the first wave of coworkers came trickling in from the hall that his phone pinged with a message. 

 

Of course, Jesse nearly dropped it like a hot coal as he clicked on the message (from Tammy, of course) to see a photo of her naked from the waist down on the floor of her office. Or, more accurately, kneeled on the floor of her office. Between her legs was his used diaper, a pink dildo balanced on top of it and looked to be inserted deep inside her by the way her head was thrown back in the photo. ‘Wish you were here baby ;)’ was the message that followed it. 

 

Like a lightswitch, Jesse found his dick hardening inside his diaper. The bulge now more than obvious between his legs. Cursing, he wheeled his chair under his desk and put his phone inside his desk drawer. Tantalizingly, his hand drifted down to squeeze his cock only to be met with a handful of padding. The rustle of fabric against his diaper was loud enough to cause him to jerk his hand away. His dick, seemingly angry at the tease of a touch, throbbed insistently. Part of him wished he was still caged. How the hell was he supposed to get any work done now?

Another ping, muted by his desk, sounded from the drawer. The temptation was too much and he fished it back out to see another message from Tammy. ‘Get back to work little boy. And no cummies! I mean it. I’ll know.’ Came the ominous message. 

 

How was this his life? He wondered. And why did it make him so horny? 

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