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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.

May quietly knocks on the door of her boss. Being the secretary of the head boss of the company, it was her duty to make sure she is ok. Recently her boss had a miscarriage and has not taken it well, their spouse has left them alone and childless, May thought that she would pop in to hand a coffee to her boss and brighten their day.