Back in New York. Alicia threw a party for me for closing the big deal. Well, we went out and had drinks. Jemma somehow found out. She ended up crashed on our couch. Alicia drew kitty whiskers on her face. Much worse things were done to people who passed out at college parties. We got very drunk. Didn’t wake up until noon. Jemma seemed to like her new facial hair.
We went to brunch at 2PM, Jemma borrowed one of my dresses. She bitched that I filled it out better. I thanked her for the compliment. I happily steered the conversation from my victory to Alicia and her ability to do body painting. Jemma seemed far too interested in that. We grabbed more sparkling wine and got drunk at home again. This time Jemma slept in my bed for fear of further body paint humour.
And at 8AM on Monday morning Todd responded the to first of my many messages from before the weekend. He was free this week, as in free for lunch and dinner. I was still kind of mad that he hadn’t called to messaged while I was in Paris, but agreed to meet him for lunch.
It was another out-of-the-way place near both our works. How does he find all these little unknown places? He was happy to see me and gave me many kisses and apologies. He was on probation, for now. I ordered sparkling water and a chicken Cesar salad. He asked about the trip and asked again after I summarized it as ‘it went well’. He was forgiven for being interested in the trip.
I told him about going over with my boss Nico. I saw that look when I mentioned her wardrobe malfunction and her falling asleep on my shoulder. I quickly skipped on to the meeting. I was unaware of how much I went on about Merce, my new French friend. Todd never stopped or interjected—I didn’t even get a chance. I totally glossed over the hard work I had been doing for weeks, which Todd called me out on. He said he didn’t know why I couldn’t take the credit I was due and instead passed it on to my ‘exhibitionist’ boss. He was right on both accounts. I remembered why I loved my boyfriend again. It wasn’t always just about hot sex.
I asked Todd about maybe going out at night maybe to a movie or a play… He said soon, but right now he was swamped with work and said, I of all people would know how that was. It’s true I was swamped with work. Sure I put in 10-12 hour days, but I still had time to get drunk with my friends on the weekend. Heck, I had time on school nights to go over to his place for naughty sex.
I asked him about the weekend. I was unsurprised when he reaffirmed that he entertained clients and prospects to make junior partner. He insinuated that his only relieve from 7 days a week and constant overtime was our time together. I think I felt a bit bad, but less that the last time I asked him. It was getting frustrated, not that it was his fault. He asked more about my trip and Merce. I went on to tell him how she showed me around Paris in one day. I told him everything about the trip, unless it had to do with Enrique.
Our food came and there was a lull in our conversation. Afterwards he asked me if I was free the next evening. For him always. Over coffee the discussion took a turn for the blue. I was now at the point I was talking with my boyfriend about fantasies in a public place. I confidently, but quietly told him I had liked our last encounter. Actually what I said was I enjoyed the role-play—though not necessarily the maid part. I said I enjoyed the spanking. I know my cheeks blushed at that and I was sure everyone in the small place must have heard it, but I said it outloud affirming it. In hushed tones I confessed to liking the bondage. I neglected to tell him it wasn’t the first time I had had sex while tied up.
In summary he said that I had enjoyed all the parts, but not the whole thing combined. He seemed kind of wounded saying that. I contradicted his summary to cheer him up even though it had been spot on. He said it didn’t matter. We were in a learning phase. He asked me in a public space if I had a fantasy. Seriously? Only one? Of course I have a fantasy or like fifty million of them. But I sure wasn’t going to tell him in the middle of a restaurant. I’ve come a long way in a short period of time, but not that far buddy. I told him I’d text him one. He paid with his corporate credit card and we kissed before returning to work.
The next day I decided to start running. No more exercise at lunch, just too messy. So I bought some running pants and a sports top…and some shoes and socks…and a matching jacket for the pants. OK, I went a bit overboard and bought a new outfit to run to work. Once there I have a quick shower and get ready for the day at work, at work. All things considered, I didn’t really lose anytime from using the subway. Now I can work through lunch (often) or go out with a coworker (sometimes) or even not feel guilty about seeing my boyfriend.
I’ve been talking with that Asian consortium that I was parachuted into in my first month of working at BCC. I mean I’ve been talking with them since being under Christine, but rather the talks have been heating up. While trying to close the European deal, I was increasing emails with a couple of the men who I met back on the terrace months ago. We connected on social media, which I started posting stuff—mostly work or fitness related—on weeks ago. Emails turned to messages, messages turned to calls and now I’m knee deep in another potential deal.
This time I’m Enrique’s wingman, or so he thinks. I’ve been upfront and transparent to him about my contact with the prospect and he’s had my research constantly fed to him. He’s happy with everything so far. Still it seems like I actually am his sidekick on this deal. I say this because although I tell him everything I’m doing, the information doesn’t flow both ways. When I asked him point-blank he smiled at me. He wasn’t yanking my chain, at least I don’t think he is, but told me to go ask my boss.
Christine was out-of-town, so I decided to find my other boss. She wasn’t in her office and her secretary said she didn’t know where she was. I had a hunch. I slipped into the store-room, which only three people had unfettered access to. I spied her rummaging through a box, half-naked. The old me would have turned around and left, more embarrassed than my boss. Actually the old me would have never come here to confront someone I almost thought of as a friend. So instead of running away I walked up to my nude boss.
She jumped, then I jumped after saying hello. Apparently I’d make a great ninja. I was trying to casually bring up the whole Asian consortium without it seeming too obvious. Instead I asked her what she was looking for. She said she was looking for a dress, a special dress. It was supposed to be here. I was getting used to my boss wandering around naked, but that tone she used was totally new—and I didn’t like it. I asked if I could help. She stopped and stared at me, you know like when some character in a movie is being mind-controlled and vaguely hears their friend. Bingo! She snapped out of her mood, I thought.
She said it didn’t matter and we could go look up something else. So with my bitchy boss hanging over my shoulder I asked her what she was looking for. A dress. The ‘duh’ was implied and again I didn’t like this person peering over me. What kind of dress I said trying to say calm. I don’t know, she snapped. I didn’t know which was weirder, that she snapped at me or that someone I respected for their decisive choices was unsure of something so trivial. I should have really known something was wrong then.
While typing in random descriptions, I decided to sequence into the topic I had come there to talk to her about. I brought up the prospect and mentioned they want to open the office on the other side of the Pacific, rather than one of our preferred cities of LA, SF or Honolulu. It was meant as small talk, but instead Nico reached over me and began typing into the search field. Two words: “serious $#!+” That’s when I finally put two and two together.
I brushed her fingers from the keyboard and spun around. Small talk was over so I just fired with both barrels, why don’t I know everything about this proposed joint venture? I was about to point out how awesome my last deal was and how much work I had put in already. I was going to point out that I never hid anything from Enrique for the European deal. I never got to say anything though. Merger, she corrected me. I literally did the Stewie “Say what?” Merger proposal, not joint venture.
Now I had a million questions to ask her, but she had stopped leaning on my to enter the shelving maze. I peeled off behind her. I found her slipping out of her panties. She looked over at me with a weird look of relief before she reached into the box in front of her. I was still a bit speechless. I wasn’t sure if it was because I was involved in such and important negotiation without being aware of what I was helping negotiate, or that we were negotiating a merger. I think I felt a bit how she did. She had pulled the dress over her head then pulled her hair away from her back. I could see in her eyes she was scared as I zipped her dress up.
How long was my first question. A few months. When, why, how? Nico finally burst into some between a laugh and a cry before hugging me. I wrapped my arms around her, I was feeling her pain. I had sen my boss without any clothes on too many times, but that day I was seeing her naked for the first time.
She told me that it had started as a joint venture between the two companies. They made clothes, we knew how to market them. As Enrique talked with them they thought it would be best if BCC went from a trend spotting and setting company to a clothing brand proper. And if not a clothes brand at least a market brand to sell clothes to consumers. Nico admitted it wasn’t really that odd. She and Christine had flirted with the idea of going retail before rather than just consulting with designers, manufacturers, and retailers. The talks went quickly from a joint venture to a buyout all while I was sweating the details of my European deal. No wonder Enrique disappeared every once in a while. She had her head on my shoulder.
Enrique was now negotiating a merger between the two companies. It wasn’t easy because of cultural differences. No, that wasn’t it she said. It was about the nature of the new company. Their new partner’s wanted a more decentralized workforce. Instead of one office in New York, there’d be more in different parts of the world. Also, the workforce would be very different—as in not everyone would make the transition to the marketing arm of a manufacturer/retailer. I thought this is what made her sad.
She further said that both her and Christine would have to sign a side deal to stay one to help promote the new company, which they no longer would be in control of. I know this was not a happy thought for my boss who had never had a boss before. She went on to say it was probably the best thing to do business wise. She and senior personnel would be handsomely bought out. That apparently included me. Hmm. The company as it was structured now wasn’t really feasible, which I had often wondered about.
Still she said, wiping her eyes to not get my dress wet, it sucked that for all her—and everyone else’s hard work—only a few would make the cut or get anything from it. Yet if they didn’t even ten clients like we just signed would save us. I felt sorry for her. I felt sorry for me, and everyone else. Either way their would be huge upheaval to come.
I patted her head and then asked a rather tactless, but somewhat important question, can I start getting in the loop with Enrique then. Of course. She raised her head and smiled for the first time I had seen her in the store-room. Of course I wouldn’t tell anyone. I just wanted to make sure we got the best deal we could. And now some of the more cryptic messages from my contacts started to make more sense.
So you and Enrique will be spending a lot of time together it looks like, her mood seemed to do a 180. We spend a lot of time together already I truthfully told her. And? Typing it seems weird because it was the way she said it rather than the actual word. And what, I played dumb. She pointed to the zipper, which I pulled down. You and Enrique she said just before tossing the dress onto the box it lived in. I already have a boyfriend, I told her. My cheeks weren’t rosy from my boss wandering around naked to another set aisle. And what does that have to do with Enrique, she said pulling out and putting on a cute crop top. I’m not like that, I stated following behind her as she strutted to the other end of the shelving. But you wish you were, she said pulling on a black miniskirt. I opened my mouth, but words failed me. My boss winked at me then left me speechless alone in the dark room.
That night I met Todd. We went back to his place, ordered Chinese food and talked. And by talked I mean gave him oral sex followed by a much-needed spanking and some very rough sex. It was cathartic. It wasn’t fun like the role-playing, but I really needed it to clear my head. I took a personally day the next day and went home to my parents to retrieve something.
The day after I met up with Nico and Enrique. They brought me up to speed on what had happened and where things were heading. I was getting the full picture now. Half the employees let go, the other half spread out between three or four offices. Nico was surprised how quickly I got on board. I had to, people’s lives were at stake. Well at least their jobs were. It was all business degree from here on in.
I spent my days with Enrique and nights with Todd. Enrique and I were sequestered in an office far from most people during the day. We had only ourselves for company. It got a bit heavy talking to our suitor then running the numbers and making counter proposals. Nico or Christine would infrequently pop in to see how wee were doing. In between we taunted and teased each other to keep things light. Then after work I’d go to my boyfriend’s to have mindless rough sex. I couldn’t keep this up for long. I knew this right away, but I wasn’t going to give up on either thing.
Jemma messaged me and asked me to lunch. I jumped at a chance to see someone other than Enrique. I picked her up at her desk. I had to conceal my feelings and pretend to be happy jubilant me. I was worried that Jemma might be a casualty of my current assignment. My guilt took her to a proper lunch—with martinis.
He asked me where I was and what I was doing. I answer top-secret in a cartoonish manner. It was true, but she accepted it. Her train of thought changed tracks. So what’s it like spending all day, everyday with Enrique? Jemma already should have known how I felt. Actually between impromptu Friday and Saturday night parties, I’m sure I slipped a bit more than I’d have liked about him. Nothing ‘smoking gun’, but something easy to read between the lines.
On the second cocktail she asked if I regretted sleeping with him. For some unknown reason I didn’t choke or spray my drink across the table. Unabashedly I said no. I was surprised to hear it come out of my mouth without any hesitation. I was just as surprised when Jemma told me neither was she. The toasting of glasses was unnecessary and possibly wrong. I would have been OK leaving the Enrique talk right there, already beyond the threshold of TMI. Apparently I was the only one who felt that way.
Jemma went on to reminisce about her night with Enrique. It both something I really didn’t want to hear and something I could stop listening to. She had been working for him as his secretary. Hmm. It had been a company social. So farther sounded familiar. They had danced, which my friend had informed me was more like dry humping on the dance floor. For the life of me I don’t know why I didn’t stop her. The third martini was the most likely culprit. But instead of going back to his place for wild pornographic sex, he instead took her back to her place. She said she was disappointed and relieved at the same time. No doubt! Nothing like company social hook up with your boss to complicate your day job.
The next day they acted as if the social night had not existed. The day after that they got all flirty. Then while in the store-room—before I sorted it, before it had a card lock and just a key lock—she realized she wasn’t alone. Shortly after Hi they were madly tearing each other’s clothes off and having sex alone in the storeroom.
For a second I forgot she was talking about a guy I still had a crush on. For a second I forgot I wan’t supposed to find that kind of hot. Two people I know getting intimate should have been Ew, but I was beginning to worry that my boss was right about me. And then, I asked her.
He got her a job as Christine’s personal assistant and writhing a week was back to flirting with her. Jemma admits it was a poor decision and he handled it as well as he could. Even through the flirting it was awkward at first until time took care of that. I asked her if she still thought of him, like that. She slowly nodded her head staring in the distance. I knew all to well what she meant. Would you sleep with him again? It was the martini talking. Jemma silently nodded again. I finished my last cocktail of the day knowing all to well how she felt.
And so that evening I stopped by home before going to meet Todd. I was sober in more than one way by that time. Todd joked that I hadn’t set him my ‘one’ fantasy. I told him it wasn’t necessary as I ate dinner and drank only water. The place was again an unknown place close to Todd’s. It was on the walk home he commented on the larger bag I was carrying. I kept him in suspense taunting him.
I skipped the customary drink when we got to his place. I told him to wait in the living room while I went up to find something. I took my oversized bag, not because I didn’t trust him to look in the bag, but because I didn’t trust him to look in the bag. I wanted it to be at least a little bit of a surprise.
I went through his closet. I was only hoping to find one thing. I found a casual pair of jeans. I put them on the bed, but that wasn’t what I was looking for. Next I found a less formal dress shirt. I put it on the bed next to the jeans, but returned to search his closet. A tartan tie… Wait, he has a tartan tie?!? I threw it on the bed. I kept searching. And then I found it, a tweed jacket with patches on the elbow. I knew he had one, he was just the type. I laid it out on the bed alone with a pair of loafers. It was just what I wanted.
I returned down stairs. He seemed confused when I returned still wearing what I had gone up in. I told him to go up and change into what I left on the bed. He was now very interested at what was going to happen. Your fantasy, he asked. My fantasy, I told him. Go sit at your desk and tell me when you’ve changed and are sitting down. He was very intrigued then and happily raced up he stairs.
When he was out of sight, I stepped behind the blind spot so he couldn’t see me even if he didn’t do exactly as I asked. I looked in my bag then started to take off my clothes. There was a moment where I felt naughty being completely naked in his apartment. It was silly, I had been naked and all kinds of other things here before, but right now I was trying to imagine all those clients and projects here being entertained by my boyfriend as I stood there naked as thee day I was born.
I quickly pulled the clothes out of the bag. They had been in my old dresser at my parents home exactly where my mother had put them. I didn’t know why she kept them, but I was very happy now she had. I doubt she would have been had she known why I was retrieving them. I started with the white knee-high socks. They didn’t quite come to my knees anymore. They probably were as white as when I wore them regularly. Next I found an old pair of white panties. Like the socks before them, they seemed to have shrunk a bit since I last wore them.
I put on the crested polo shirt. It felt weird to start buttoning it up without a bra—or at least a camisole. The fact I could button it up was giving me hope for the last most important garment. But before that I put the scarf around my neck and ties it like a cravat. That left the tartan pleated skirt. I had hated wearing it in high school. I sucked in my stomach and was happy I could still fit into it. I wasn’t fat, far from it. I just wasn’t a teen-aged girl anymore. And looking in the one mirror I could find, my old school uniform was a bit too tight and a bit too small. It was perfect!
I heard him call down from the loft. I put my hair into two pigtails before peeking around to make sure he wasn’t looking over the railing to spoil the surprise. I sent him a detailed text then made my to the stairs. My fantasy was very simple. It wasn’t even very unique. I along with most of the girls at my high school had had a crush on this young hip teacher. Don’t stand so close to me, indeed. I never would have slept with my teacher the way that Jemma had slept with her boss, but now we were in the realm of consequence free fantasy. Now I could figuratively sleep with that teacher I hadn’t dared to.
He knew immediately what was going on when I appeared at the top of the stairs. Todd, my teacher reached for a pair of reading glasses. It certainly did not take anything away from the hip young teacher look. I sheepishly tiptoed over to him. I avoided eye contact.
“Alex, I’m not sure what to do. You’re grades are dropping and you’re getting disruptive in class.” I was never disruptive in class, but I went along with it.
“Sorry, Sir.”
“I’m afraid after that last test, your scholarship may be in jeopardy.”
“No Sir. I can’t lose my scholarship. I’d have to leave school and my parents…” Like the store room, I was just making it up. “Please my parents can’t find out. I you’d just let me take the test again, I’m sure I’d pass.”
“Even if I could let you take the test, which I can’t; I’m not sure you would pass. Passing notes and daydreaming in class. It’s not like you. I’ll be sorry to see you leave. I had high hopes for you Alex.” Goddamn! Was Todd a teacher in another life? I got caught up in it.
“Please, I’ll do anything”, and how, “if I can just retake the test. And I’ll pay attention and won’t be disruptive. Please Sir give me another chance!”
“I can’t. The tests are marked and recorded. The only way you’ll be able to stay in this school is if I go tell the Head Master I made a mistake entering your results. And then I’d be the one on probation and on my way to getting kicked out of school.” I actually felt bad for my fake hot teacher. “I bet they are writing the letter to your parents right now.” I saw that glint in his eye as he turned up the heat. I returned my sorrowful gaze back to the floor.
“Please Sir, I’d do anything. Please have them change my grade, I don’t want to be kicked out of school.” To be quite honest it was a real fear of mine back when I was fantasizing about that teacher. A graduated Valedictorian of my class, but.
“And even if I risk getting fired for you, what about the last couple of months where you’ve undermined me in my own classroom?” Wow! I was a totally $#!+ disturber! Maybe I deserved to be kicked out of school and end up an exotic dancer. Wait, that’s another different fantasy.
“Sir, you can do anything to me. I’m sorry I disrupted your class and made you feel disrespected in front of the other girls. Anything.” I was really selling to next part of the newly appended fantasy.
“OK, first we’ll address the poor behaviour. Then if I feel you’re genuinely remorseful we’ll see if you’re worth losing my job over.” I got shivers when he said that. “Come over here.” He said it quiet, but forceful. It gave me goosebumps.
He had been standing since I came close to his desk. He now came around and stood directly in front of me. I didn’t dare look up at him. “Go fetch me my chair.” I did it with maybe a bit too much zest. I’d like to think the schoolgirl was motivated by fear and did it double time.
There was little surprise what happened next, I just waited with anticipation as he sat down. Though my school had abandoned corporal punishment there were tales told of when it was common practice. It was probably more like ghost stories, but every time tales were told they got more brutal and humiliating.I really doubt anyone at our school was ever stripped naked in front of the whole school and hit with a birch switch. At least I hope they weren’t.
I once again said I was sorry before I voluntarily lowered myself onto Sir’s lap. He told me again how bad I was and how disappointed he was with me. Ya, ya, ya. Just get to the good part.
I felt him lift up the short skirt. Maybe the sight of my ample bottom in too small panties was enough to shut up his derogatory speech. What ever, I was happy it happened. What made me even happy was that first slap on my backside. Followed by the second and third. I might have zoned while finally living out my fantasy. Thank God was wasn’t supposed to be counting or anything like that.
“Are you sorry for disrupting my class” was the question I was supposed to be answering.
“Yes, Sir. Very sorry.” I didn’t think my delivery was bad so much as late.
“I don’t think you are!” And with that my petit sized panties were pulled down off my warm bottom. He continued to pepper my bottom with more vigour now. Nothing like a schoolgirl’s bare bottom to fire up a handsome young teacher. He wanted me to count, but I kept getting lost in the sensation of his hard hand repeatedly slacking my upturned backside. I squirmed from equal parts pain and pleasure. My brain was releasing dopamine like nobody’s business. Finally I was moaning, which could and was construed as whimpering.
“Please Sir”, I mumbled. It was more from desperation than defeat.
“Stand up.” It wasn’t yelled, but it wasn’t a polite direction either. I wanted him to grab my hair and… First things first. I stood up and flinched as the woolly skirt fell down over my irritated bum.
“Are you ever going to be disruptive in my class again.”
“No, Sir. I won’t disrupt the class ever again.”
“And you won’t be disrespectful in my class again?”
“No Sir. I won’t be disrespectful to you again.” My eyes were teary from the spanking, though they did sell the ‘I will never be bad again’ lines.
“Fine! Now we’ve dealt with your pro behaviour in class.” Oh, ya. I still had to find a way to stay in school. “I don’t really think I can help you with your marks though.” What? I’ve been betrayed! I took a brutal and humiliating spanking for nothing!
“Sir, I can’t be kicked out. My parents can’t find out I was kicked out of school. They’ll disown me and kick me out of the house…” And I’ll take my schoolgirl uniform to the biker bar off the old state highway… “I’ll do anything if you can change me marks.” I really sold it with some hopeful puppy dog eyes. Hopeful of what I’d have to do to get him to change my marks.
“Anything…” His voice trailed off as he stiff up out of the chair. He took off his jacket and lay it on his desk. He waited for a second. He really sold the hesitation and crossing the point of no return. Then he undid his belt before unbuttoning his jeans.
“No Sir!” I protested. I’d need a push across that point of no return. “I can’t do that!”
“Then your parents will know you’re getting kicked out tonight. I’ll call and tell them myself.” I have to admit, it kind of scared me half to death. I was on my knees in front of him forgetting this was my fantasy. He let me paw and his pants and underwear. It was nice to know he was enjoying this as much as I was.
And then my innocent little school girl did something very naughty to not get expelled. He leaned back on his desk and I took him in hand. My first steps very somewhat tentative. I almost forgot what I should be doing. Either way he seemed to be enjoying the fantasy as much as I was in spite of the awkward oral sex I was giving him. He grabbed my twin pony tails and let out a few sighs and barely audible words. Apparently badly performed oral sex only helped to sell the fantasy more. The awkward phase was short before I started to work him the way he liked. I was careful not to work him too hard…
“Is that good enough Sir?” The schoolgirl hoped that was enough to keep her in school. I had left him near the edge, and could guess what his answer was. I was right in guessing his response, but wildly off in the magnitude.
“I don’t think so 𝛃!+₵#” He grabbed his belt and tied my wrists above my head then grabbed me by my pigtails to drag me up and across the table. My heart was pounding. For the first time this night I wasn’t sure what was going to happen. It was scary and exciting. I think he hooked the belt and my wrists on something because I couldn’t move my arms. He pulled up my skirt again before he pushed down my panties to my knees. He smacked my already sore bottom again. “Please Sir”, I pleaded.
“I’ll teach you to not screw around in my class!” He stomped my panties to my ankles then I felt him from behind. The school girl was terrified. The woman playing the school girl was ecstatic. Then with an expletive laden tirade he pushed into the naughty school girl taking her innocence away. Or whatever.
I was actually enjoying the savageness of the sex. The mental aspect of the role-play and the ad hoc bondage. Not exactly the way I’d have liked to be taken by that handsome young teacher, but totally what post-secondary me wanted. He kept up telling me this was the only way I was going to be able to stay in school. That touch was almost as appreciated as much as the smacks on my red bottom.
Then pulling out he rolled me on my back and lifted up my skirt. He ejaculated across the tops of my legs to my tummy. He smacked between my legs which reignited my own climax. The last bit had been a bit intense. There would be words about it. In the mean time we kissed and cuddled on his desk—my arms still trapped above me.
We each had a shower. I was last and joined him naked in bed. He asked me how I liked it. I said for the most part I loved it. And the ending he asked. I’m coming round to it. I told him I would have liked some warning, though I then admitted had he asked I would have probably said no to it.
So in summary while snuggling up to him, I said I liked the role-play, but not so much the derogatory stuff. He asked if I had a teacher who I had a crush on. I admitted I did. I asked him if it bothered him. He said no. He asked if I had any other fantasies, which I said yes. He asked what they were. I told him he’d have to wait. I asked him if he had any fantasies. He responded with an enthusiastic yes. I asked him if he would share one with me. He asked if I had ever been to a fetish party.
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