My First Job

[BabyBear85]

Part 1

I had been working at a small company for a couple of years, my first real job out of college. I was naive, and made a few mistakes along the way, but had also made some good impressions with my boss, Mary. She seemed to value my work and my potential, and had started to act like a bit of a mentor. As VP of Operations, Mary certainly didn’t tolerate any nonsense, but she was also compassionate and supportive. A recent empty-nester (and longtime divorcée), it was clear she had a strong maternal side - firm, but caring.

Mary was also easy on the eyes. She had a full, hourglass figure, dark hair and blue eyes. She was a smart dresser, professional but sexy in an authoritative way. There was no question she was the boss.

As a horny, rather inexperienced 23-year old with a penchant for take-charge women, I was a bit smitten. I was, of course, always professional, but welcomed every opportunity to interact with Mary, and eagerly accepted her guidance.

Over time, I eventually developed a fantasy of being privately scolded by her for making some mistake, then pulled over her lap for a solid spanking. The fantasy evolved, but always remained just a wild fantasy, until…

I had been assigned to help on a proposal for a new client. It was a months long effort, but had the potential to be huge new business for the company. It was a stretch opportunity for me, and I was eager to show Mary I was up to the task.

The deadline finally came to submit the proposal and we were editing down to the wire. Working well into the evening, eventually no one was left in the office but Mary and me. Finally finished with every last detail, I clicked submit on the online document repository, then got a prompt: “Documents loading … approximately 2 hours to full upload.”

“Aww dammit!” I let my frustrations out. It was already after 9 pm! I’d be lucky to make it home by midnight. Suddenly Mary popped in my office.

“Everything okay?” she asked.

“Oh, yeah, sorry,” I blushed a bit. “The documents are loading, but it says it will take two hours before they’re fully received.”

“Ah, bummer - all that work, now hurry up and wait…” she replied.

“I don’t mind staying to wait for it to finish, you can head home,” I offered, trying to score some brownie points.

“That’s ok,” Mary said. “How about I wait with you? I think there’s some wine leftover from the event last week, I’ll go dig it out. We should celebrate anyway, your first big client proposal!” She disappeared around the corner.

My stomach fluttered. One on one time with Mary, after hours, with wine…! The evening was shaping up.

Mary came back to my office and poured the wine. As she leaned over my desk to check the upload progress, I got a nice view down her blouse at her big tits.

“Ugh, 1 hour 55 minutes,” she read, taking a big slug from her wine glass. “We’d better drink up.” She winked at me, and I followed her lead, taking a nice long gulp from my glass.

Taking a seat in an empty chair across the office, Mary started in with small talk. The more we drank, the more we laughed. Eventually, the conversation came around to my first few weeks on the job.

“Oh my,” Mary commented, “you were so fresh faced and eager, but a little clueless,” she giggled. “Sometimes I felt more like your babysitter than your boss!”

I nearly choked on my wine, but managed to hold it together. I could feel myself blushing. I feigned indignation. “Oh what do you mean?? I could handle myself!” I said, laughing nervously.

“Oh please. I had to constantly clean up your messes. Remember what you blurted out at that client meeting in your first week? You’d have been better off with a pacifier stuffed in your mouth!” she erupted in laughter.

I could feel my face flush deep crimson. Mary stopped laughing and suddenly looked slightly concerned that she had crossed a line in her teasing. For my part, even though she had embarrassed me a bit, I desperately wanted to egg her on. I quickly took a gulp of liquid courage.

“Ok, ok yeah that one was pretty dumb on my part,” I said, “but I wasn’t THAT bad. I mean, it’s not like you ever had to punish me!” I giggled.

Mary raised an eyebrow. She seemed to study me for a moment, then slowly sipped her wine.

“Well maybe I should have…” she said.

Her words hung in the air. I let out a nervous giggle, anticipating what might come next. She stared at me intently, a half smile starting to curl on one side of her mouth. Her red lipstick glistening, her blue eyes seeming to pierce right through me. I reached for my wine glass and clumsily knocked it over, spilling across my desk.

Mary gasped and jumped up. Grabbing some tissues, she started to mop up the wine from the desk top.

“What did I say? Always cleaning up your messes,” she chided. “Next time I’ll have to remember to bring you a sippy cup.”

I stood behind my desk feeling about two feet tall. Mary’s playful scolding was making me feel like a small child. And it was also turning me on.

She finished wiping up the wine and tossed the tissues in the trash can. She leaned across my desk and checked my computer to see how long the upload still had. I again took the opportunity to ogle her voluptuous rack.

“Ahem..” Mary cleared her throat. I snapped my gaze away from her tits to see she was staring me dead in the eyes. “About 35 minutes still…”

“Now then, before you went ahead and proved my point about you needing someone to clean up after you, we were discussing the matter of your punishment. Or rather, lack thereof.”

My mouth went dry. I was in a daze. Could I really be on the cusp of realizing my fantasy?

Mary’s voice cut through, sharp and firm. “How long has it been since you were last spanked?”

I smiled reflexively and nervously. My mouth was still too dry to speak, my brain too stunned to form words. I gaped back at her silently.

“Well? Come on now… when was the last time someone pulled down your pants and put you across their knee for a good spanking??” she pressed.

“I… um… well I guess… never really,” I stammered rather meekly.

Sitting back in her chair she stared back at me. “Never???” she repeated incredulously.

“Yeah, I mean, my parents didn’t really believe in that.”

“My, my,” Mary shook her head. “And you never had a girlfriend give you a good smacked bottom?” she pried, a thin smile growing on her lips. I shook my head no. I had never worked up the courage to share my fantasies with anyone I had dated this far.

By now, my cock was raging hard, bulging beneath my pants. I could hardly believe what was happening.

“Well I think it’s time we fix that. I believe strongly that you’re never too old for a trip over the knee. And there’s no time like the present. Come on over here young man.”

As if on a conveyor belt, I glided across the room to where she sat. Mary took my hands and directed me to her right side. Then with a quick tug she had me sprawled across her ample lap, face down with my butt skyward and exposed.

“Since this is your first ever spanking, I’ll allow you to keep your pants up. But I’m warning you, if we have to repeat this any time soon, it will be on you bare little bottom. Understood?”

Somehow I managed to squeak, “yes ma’am.” My cock pressed through my thin dress pants and into Mary’s thighs. Squeezing her legs together and acknowledging my bulging manhood, she commented, “It seems like someone is enjoying himself… let’s see how long that lasts.”

CRACK! Her hand fell firm right in the middle of my cheeks. SMACK SMACK! She gave a few good hard slaps, the paused and rubbed my ass all over. My dick throbbed with anticipation, and worked its way deeper between her legs.

Another volley landed, SPANK SPANK SPANK SPANK!! The sting was real, but it felt strangely good, and made me buck and shift, rubbing my cock back and forth across Mary’s legs. My pleasure and anticipation grew as Mary alternated spanking and caressing my butt.

“This is what happens… SMACK… to little boys …SMACK… who make big… SMACK… messes… SMACK… for their mommies… SMACK… to clean up
…SMACK SMACK SMACK!”

The scolding made my cock even stiffer. She began rubbing again.

“That’s what you need, isn’t it?? A mommy to look after you. Clean you up when you make a mess. And… SMACK!! … spank… SMACK … your little … SMACK … bottom … SMACK … when you misbehave.”

The barrage of spanks that followed were too much. As Mary spanked, my cock rubbed harder and faster against her thigh. The pressure became too much, and I spurted a hot puddle of cum into my underwear, groaning deeply as I did.

Mary finished with a flurry across my backside, just as I finished blowing my load. She rubbed my butt for a minute while I caught my breath.

“Ok, stand up young man,” she instructed. Still in a fog from my orgasm, I complied.

“Oh my, just look at your pants you naughty boy!”

I looked down. My light gray slacks had a massive wet spot in the crotch. Mary clicked her tongue and tsk, tsked me.

“I knew you needed looking after.” She picked up some tissues and dabbed at my wet pants. It did little to clean the mess, and left fuzz on my crotch, further accentuating the stain.

“Well we can’t send you home on the bus in this state. You stay right here, there’s a Walgreens around the corner and they’ll have everything we need.”

Mary stood and took my chin in her hand. Looking me squarely in the eye, she said, “You’re not quite done being punished young man. I saw you peaking down my shirt earlier.”

I blushed again, and swallowed hard. I stammered “I wasn’t… I didn’t mean to… you just leaned over and … I’m sorry.”

“Yes I know you’re sorry,” she winked at me. “But you still need to be punished.”

Guiding me by my hips, she shifted me back behind my desk. Checking the upload she noted “oh good, only ten more minutes.”

She continued pushing me by the hips past the desk and toward the wall.

“Stand here with your nose in the corner until I come back. I’ll only be a few minutes.”

Propping me in the corner with three sharp smacks to my tingling bottom, she added, “Don’t even think about stepping out of there. I’ll know if you do. And you won’t like what will happen next.”

A final hard whack to my rear, and she was out the door.

 

[BobbyDrago]

Well that moment you find out the boss is into the same freaky stuff as you.

[Babyqtboy]

Well, definitely an interesting start and I like the premise ? definitely look forward to reading more of this

[BabyBear85]

Part 2

I stood in the corner contemplating what had just transpired. My bottom had a light tingle - the spanking had not been very harsh, my pants providing some protection. The front of my pants, though, had grown cold and sticky. 

I felt some embarrassment about my predicament. Unable to contain my excitement, I had demonstrated a lack of experience and control. Mary seemed to be rolling with it though, so maybe I didn’t need to worry. 

Reaching back, I rubbed my backside, feeling a slight sting as I touched my cheeks. I gave them each a squeeze and the sting intensified slightly. My cock stirred… I was anxious for Mary to return, but also apprehensive about what else she had in store for me. My mind wandered back to some of the comments she had made about pacifiers and sippy cups. I happened to know that Walgreens carried both of those, along with a variety of other baby items… I could only imagine what awaited me. Until…

“Good boy, staying put as instructed!” Mary burst back in the room, cooing at me proudly as though I were only four years old. “You can come out of there now and see what I brought for you.”

I slowly turned around to find Mary setting down two full plastic bags. First she took out a pair of black sweat pants and set them on the desk. 

“These can replace those soggy sticky pants you have on. Next, we have your new cup, so there are no more spills.” She removed a small sippy cup adorned with Cookie Monster, and promptly filled it with wine. She handed it to me, and stared. 

It took a moment, but eventually I realized she was waiting for me me to take a drink. I put the cup to my lips and sucked out a sip of wine. “Good boy!” Mary cooed. 

“These will help us clean up any more messes,” she said, setting out a box of Huggies wipes. 

Next, she pulled out a blue and white pacifier, quickly tore it out of the packaging and stuffed it directly in my mouth. 

“For your next client meeting,” she said, winking and pinching my blushing cheek. 

“Now they don’t sell underpants at Walgreens, so we’ll have to settle for these.”

Mary placed two packs of boys XL Goodnites on my desk. She glanced up at me, noticing the smile spreading behind my pacifier. “And besides, seems you need something a little more absorbent anyway,” she said, smiling and pointing at the stain on my pants. 

She tore open one of the packs and took out a pull-up. Setting it on top of the sweat pants and handing both to me, she instructed, “Take those wet things off and fold them neatly. Clean yourself up, then put these on. I’ll be back in exactly three minutes.”

The door clicked closed behind her, and I stared down at the diaper in my hand, and the two full bags of them sitting on my desk. I was in a state of shock, but my dick on the other hand, was waking back up. 

Realizing it had been nearly sixty seconds already, I quickly stepped out of my shoes and slipped my pants and boxers off. I popped open the box of wipes and cleaned the hardening jizz off my crotch. 

Stretching out the Goodnite, I felt sure it would fit around my slim frame. Actually, I was absolutely sure, having sampled Goodnites on my own recently. 

I slid it on and quickly pulled up the sweats over the diaper. Scooping up my pants and underwear I hastily folded them and set them on my desk just as the door opened. 

Mary strode back in, her heels clicking. She beckoned me around the desk to where she stood. “I need to check.”

Again it felt as though she had turned on a conveyor belt. I was instantly standing in front of her, and she quickly tugged my sweats to my knees. 

“Hmm a sung fit, but should do the trick for small accidents.” Mary pinched the padding in my crotch and ran her fingers around the waistband. “We may need to eventually think about something thicker, though.”

I was completely under her spell. Mary could have told me to run through a brick wall and I’d have done it. I stood staring at her, my cock fully hard now, hanging on her every word. 

Turning back to the plastic bags, she dug in for the remaining items from her shopping spree. Out came a large bottle of baby powder. Twisting the cap open she pulled open the back waist band of my diaper and dumped some in. After doing the same in the front, she set the bottle down with the wipes and Goodnites. 

Giggling, she rapidly patted my bottom and made a cloud of powder poof out. I giggled too, and savored the sweet babyish aroma. 

Next she pulled a bottle of scented baby lotion, and lined it up neatly with the other changing supplies. 

Finally, only one more item remained. I gulped audibly as Mary pulled it out… a large, flat-backed wooden hairbrush. 

“I told you that your punishment was not over, didn’t I?” she said, tapping the brush against her left palm. 

“Y.. yes m.. ma’am…”

She sat down. 

“Well. What are you waiting for? Get over my knee,” this time tapping the brush against her thigh. 

My pants still at my knees, I waddled over to her and complied. I quickly found myself in the exact position I had only recently been, but this time clad in a tight fitting pull-up diaper. I must have been a sight. 

Mary certainly seemed to be enjoying the view for her part. She took her time, beginning to slowly rub my butt only after sitting silently for a moment. 

Her hand came to rest squarely in the middle of my sit spots. She again paused a moment, then patted me gently. 

“I believe I told you that if I needed to spank you again, I’d bare your bottom first. Didn’t I?”

My cock pulsed and bulged, constrained in the tight padding. My mouth was dry, but I mustered, “yes ma’am.”

I felt her thumbs hook the waist band on my pull-up. She tugged, and the cool air hit my naked cheeks. Baby powder wafted. Her hand caressed me briefly, as my cock dripped into the padding. Then…

CRACK CRACK CRAK CRACK

Mary’s hand landed in rapid succession. I was struck (literally and figuratively) by how much more the spanking stung without the protection of pants. 

As my cock jostled and rubbed against Mary’s thighs with the Goodnites padding the only thin layer between us, I briefly considered how it might feel to be spanked in pull-ups. 

I was quickly brought out of my fantasy by the reality of Mary’s steady, sharp hand spanks alternating from bare cheek to bare cheek. She began scolding. 

“What a dirty naughty boy you have been tonight. First looking down my shirt, then making a big sticky mess in your pants when you were supposed to be getting punished.”

The sting was real, but my butt had warmed up, and the spanks were sending wonderful vibrations through my ass and to my throbbing cock. I was definitely in danger of making another mess. 

Suddenly, the spanking stopped. I could feel heat rising off my butt into the air conditioned office. I was craving more…

“Since you seem to be enjoying yourself a little too much,” Mary squeezed her thighs and teased my cock, “I think you’re going to need to feel what a real spanking is like. That’s why I bought this hairbrush.”

WHACK!!

I gasped as the brush connected. That hurt!!

WHACK WHACK

Mary paused and rubbed the brush against my reddening bottom. 

“I bought this brush to keep in my desk drawer. For this explicit purpose. I want you to think about that while I paddle you. This is what you can expect from now on when you misbehave.”

I didn’t speak. I couldn’t. I held my breath. 

Mary brought the brush down without mercy. A barrage assaulted my bare backside. I had no idea what I’d gotten myself into. My ass was on fire, and I instinctively reached backwards to try to put it out. 

As though she’d done it a thousand times, Mary snatched my wrist and pulled my arm behind my back to control me. The hard paddling never relented. 

“You hold still and take your punishment little boy. Maybe if someone had spanked you sooner, you wouldn’t been looking down ladies’ shirts. I clearly should have had you over my knee a long time ago.”

My cock was limp. The fantasy playing in my head had ceased. The only thing I could think about was the sizzling pain continuing to grow on my bare bottom. 

“From now on, I expect you to show more respect for women. And I expect you to control yourself and stop making messes in your pants.”

Mary stopped spanking for a moment. She reached between my legs and tugged at the elastic and padding in my crotch. 

“We’ll definitely need to keep you in these pull-ups for a while though, just to be sure. But if you keep having accidents .. WHACK .. you can count on a good smacked bottom .. WHACK .. and then we’ll have to put you back in thick baby diapers.”

She began spanking again, rhythmically, covering every inch of my butt. I was sure I’d have bruises when she was done. It became too much. 

“I’m sorry ma’am, please stop! I can’t take any more! I won’t do it again!” I sniffed, as I could feel tears welling in my eyes. 

To my surprise, she did stop. “I know you are sorry young man. But I don’t believe you won’t do it again. I can assure you that this won’t be the last time you are over my knee.”

She tapped the brush against my bottom firmly. I gasped, and felt a tear streak my face. 

“I need to make sure this is a memorable spanking though, so that hopefully we won’t have a repeat any time soon.” She stretched one leg across mine, locking me in position. 

“How old are you?” she demanded. 

“23,” I mustered. 

“Pssh.. acting much more like a THREE year old than a TWENTY three year old, with you little diaper pulled down, getting a good spanking like a naughty little boy across his mommy’s knees,” Mary scoffed. 

“Nevertheless, I am going to spank you 23 more times, then we’ll be done. At least for tonight…”

Her last comment was ominous, but I was relieved to know my spanking was almost over. 

“I want you to count. And believe me, I am going to MAKE THEM count.”

I gulped. Mary reared and connected. I bucked, but she held me firmly down. 

“ONE!” I nearly hollered. Mary let out a giggle. 

She continued to smack in steady succession. The brush was landing with ferocity. I was barely keeping it together. By ten, I had started to sob softly. 

At 18, Mary paused. “Five more, little boy. It’s ok to cry, these will hurt. Then all will be forgiven and you’ll be my good boy again.”

I merely nodded, and began to cry a little louder. I sobbed my way through 19 and 20, but on 21 I broke down. Through my bawling, I couldn’t keep count out loud. Mary showed mercy and didn’t force me to count. But she did not show my butt mercy. It felt as though she was peeling my skin off with that brush. 

Finally it stopped. Mary held me tightly in position for a moment and let me catch my breath. She shushed me gently and called me a good boy. Even though my ass was on fire, her soft touch and comforting voice made me feel reassured, safe and contented. 

I felt her reach toward the desk. She clicked open the lid on the lotion and squirted some into her hands. She gently applied it to my hot bottom, making me flinch initially at the cold, but then relaxing as the cooling sensation spread across my scorched ass. 

When she finished massaging in the soothing lotion, Mary tugged my diaper back into place. Patting me gently, she instructed me to sit up. I came upright to sit sideways in her lap, my sore cheeks dangling off the edge. She wrapped one arm around my shoulders, her other hand cupping my padded bottom. 

“Now I know you learned a lesson, and all is forgiven. Hopefully we won’t need to use that nasty brush again anytime soon,” she tapped my butt sharply, making me wince. 

“No ma’am.”

“Did you manage to keep your undies dry this time?” Mary asked. 

“Yes ma’am.” My hard on had faded during the hairbrush spanking, but had started creeping back while Mary had rubbed me with the baby lotion. I was well beyond half mast by this point. 

“Let me check,” she said, standing me up. Mary stuck her hand between my legs, poking at the padding. As she slid her fingers inside the leg guards, she brushed against my dripping member, which was growing harder and harder. 

“Tsk tsk, it’s a little damp in here…” she scolded. “But overall pretty dry. Definitely an improvement.” She reached for the baby lotion. “I think maybe you deserve a reward.” 

Squirting more lotion on her right hand, she worked it deeper in the pull-up, gripping my cock. My knees buckled as she massaged and tugged.

Mary reached her other hand behind me and played with my pull-up waistband, slowly teasing her hands down the back toward my butt. Caressing my stinging rear, her fingers tickled my crack. After a few more solid tugs on my lubricated cock, I again spurted a load, this time absorbed by the padding in the pull-up. I moaned and wobbled in ecstasy. 

Mary cooed at me, “Good boy, good boy. Fill up your diapies. That’s my good boy.” 

I started to collapse. Mary guided me to the floor, my head and shoulders resting on her lap. She held me and stroked my hair. I don’t think I had ever felt this good in my whole life.

[BobbyDrago]

Mary seems like she will be a good mommy for her boy! Now if only she could get him back on a liquid diet.

[Eagle0769]

Oh yes this is my kind of story although I never write this type

but i enjoy reading them.

She called herself "Mommy" I wonder if that is what she will be

or will it be "Mommy Mistress"?

I hope she will be "Mommy" but "Mommy Mistress" will be good too.

I can't wait for the next chapter. Good job ?