2 – Amy’s First Time

I didn’t feel any differently the next morning, conflicted and excited at the same time until I saw Amy late in the morning. We passed each other in the hall, and though we couldn’t say anything about our thoughts, we didn’t need to. On her face, I saw a combination of shyness, a response to my facial reaction to her outfit, pride, knowing she looked terrific, and excitement, knowing what that look would get her.

She’d put together a look that was as close to ‘schoolgirl’ as possible without anyone thinking that was the look she was going for. I knew, of course, because of what I would do later: spank the naughty schoolgirl!

I first noticed a pleated skirt long enough to be modest but short enough to be young and sexy. In solid navy, it contrasted with the plain white blouse dramatically but showed her long legs to their best advantage. The blouse was also a perfect compromise of tight but not slutty, with a button or two open to reveal, just barely, the top of her white lacy bra. The cuffs were rolled up, leaving only a portion of her forearms bare. She wouldn’t get away with white knee socks but did choose a pair of simple black pumps, typical of private school uniforms. Add a high ponytail held in place with white and navy ribbons, and she looked like a private school graduate who couldn’t quite give up the uniform.

“Hi, Mark!” she said, with a smile that wrapped up half a dozen different emotions: cute, shy, excited, naughty, proud, and left me tongue-tied. I managed a simple ‘Good morning, Amy’ that revealed my surprise and approval of her outfit. Once we’d passed each other, we both looked back; I got another glimpse and a view of her bottom in that skirt, and she saw that I had looked back. Knowing that, she smiled again and went on her way. I found myself wondering what kind of panties she had on and decided at that point that I would find out by going through with her crazy plan.

She waited a couple of hours after lunch to get the ball rolling, precisely what I would have recommended. Not too early as to be distracted by anticipation all day, but not too late to allow some tension to build. She showed up at my door with her sad, pouty face.

“I’m sorry, Mark! I didn’t mean to do it! I guess I was just distracted, but I ran the test without resetting the parameters again. I’m sorry!” Of course, there wasn’t any test or parameters to reset, so I played along. She shuffled into my office and stood in front of my desk.

Turning to my computer, I said with an air of frustration, “So let’s see what you’ve done.”

“Don’t bother. I already deleted it,” Amy replied.

“What? Why? I could have salvaged most of it!” I lied, making the situation sound even worse than any prior mistake she’d made.

“Ohhh, I didn’t know that! I’m sorry! Please don’t be mad at me.” she begged.

“I’m not mad, Amy, just disappointed. How many times have we been through this?”

“I know. Yes, you’ve told me a couple of times before. What are you going to do?” she asked as she closed my office door and returned to the side of my desk.

“What am I going to do? I’m going to do what I should have done a long time ago! Do you remember what I said I’d do if this happened again?”

“You wouldn’t really do that, would you?” she asked, barely suppressing a smile.

“Yes, I would!”

“But … but you’re not really going to … to spank me, are you?” she asked, whispering the words ‘spank me.’

“Amy, I don’t know what else to do. We’ve been over these procedures many times, and, at worst, I’d expect you to ask before acting if you’re unsure, but you keep screwing up the test, which causes me a lot of extra work. Work I don’t have time for!”

“I know. I’m sorry,” she replied dejectedly.

“If there is some other way I can get this through your head, I’m willing to listen.”

“No. I know you’ve tried. When and, um … where are you going to do it?” she replied with a perfectly contrite look.

“Right here. Come back at six o’clock.”

“Here? What if someone hears?”

“Amy, the office is empty by five on a Friday. Even the cleaning crew has Friday off. There will be no one to hear except me and you!”

“Okay. I guess there’s no way out of it, huh?”

“No. Six o’clock. Right here, over my knee, on your bare bottom! Got it?” I asked and received a slight nod in reply. “Don’t be late!”

“I won’t. You’d probably spank me even harder if I were!”

“Now you’re getting the idea! Maybe this will actually work!”

“Maybe for you! But you’re not the one getting spanked!” she said as she approached the door.

My hard-on ratcheted up a notch or two as she rubbed her bottom, anticipating the pain. She looked back at me, trying to maintain a sad look while still rubbing her behind. She bit her lip sensually and smiled, seeing my reaction to her ‘accidentally’ lifting her skirt to reveal tight, white panties underneath. Returning her gaze, I tried to communicate a warning about any further naughtiness, and I think she got the message as she tugged on her skirt hem and disappeared through the door.

‘Wow!’ I thought to myself. She was good at role-playing, and I immediately began to miss what I hadn’t even gotten from Amy yet, knowing it would be just this once and never again. ‘Better make the best of it,’ I said to myself and tried to get back into my work, the only thing that would make the two-and-a-half hours pass without excruciating slowness.

I did have a lot of work to do, so I set an alarm in Outlook for five-thirty to give me time to prepare. The time went faster than expected, and I even snoozed the alarm a couple of times until almost a quarter of six, when I stopped my work. While my computer backup ran, I retrieved the chair I’d use. All those in my office had arms, but an office a couple of doors down had a couple of very plain, chrome-framed chairs with thin, gray upholstery and no arms to get in the way of having Amy across my knee.

I placed it directly in front of my desk, where I’d have Amy sit while I scolded her a little before starting. I straightened up my desk, just in case I’d want to bend her over it, though I didn’t plan to. Amy would get her entire spanking over my knee unless she wanted more. With less than five minutes to spare, everything seemed ready, so I sat down to wait.

Amy came from up the hall, so I could see her walking to my office with her head hanging and in a deep state of depression; overdone, faked depression, but depression, nonetheless. She came right into my office and closed the door behind her.

“Is that where you’re going to …” she said as she noticed the out-of-place chair in front of my desk.

“Have a seat, Amy,” I said, indicating the chair.

“Can’t we just do this and get it over with?” she asked, though I knew that was the last thing she wanted. She didn’t want to delay any further but didn’t want it ‘over with’ too quickly, either.

“Sit!” I said firmly, taking conspicuous notice of her luscious thighs held primly together as she sat her soon-to-be sore bottom in the chair. “Why are you here, Amy?”

“Because you told me to!” she said defiantly.

“Okay, what are you here for?” I asked, rephrasing the question to elicit the answer I was looking for.

“Um, to be punished, I guess,” she replied with a bratty attitude.

“We haven’t even started, and you’re already trying to make it worse?” I asked with a warning tone. She held back a smile I caught forming in the corners of her full, red lips.

“I’m sorry. I’m here to be punished, sir,” she answered, trying to show the proper respect.

“Better, and why are you being punished?”

“Because I keep making mistakes and don’t pay attention to my work, sir.”

“Good. And how are you to be punished?” I said, barely suppressing a smile myself.

“With a spanking, sir.” My look told her that wasn’t as complete an answer as I expected, so she tried again. “You’re going to put me over your knee and give me a spanking on my bare bottom.” Her excitement in making that simple statement was evident as she squirmed in the chair, dying for it to begin.

“And do you agree that you deserve to be punished in such a manner?” I asked officiously.

“I guess so,” she replied noncommittally.

“There’s no ‘I guess so,’ Amy. You don’t have to take this punishment. You do have another option.”

“Meaning I’d lose my job, right?”

“That’s correct.”

“Then, I agree I deserve to be punished.”

“Okay, stand up.”

I stood up as well, and the tightness in my crotch became more evident to me and probably to Amy as well. When she saw me heading for the chair, she moved out of the way and let me sit. Taking her hand, I guided her to my right side and left her standing there.

“Now, I want you to tell me again why you need to be punished and then ask me to punish you. I want a clear, complete, and detailed statement that shows you understand why this is happening and that you agree it's deserved. Understand?” I find that first-timers often like talking about it in anticipation of finally realizing their fantasy and appreciate the reality even more when it finally comes.

“Yes, I understand,” she said. “Um, I’m going to be punished for not paying attention to my work and making too many mistakes. Please spank me, sir. Take me over your knee and give me a good spanking on my bare bottom.” She looked me in the eye as she said it, ramping up my arousal in the process as well. As she finished, her face sought my approval for her statement.

“Very well, Amy. Lie across my knee.” She carefully lowered her body across my knee, steadying herself with a hand on my thigh before dropping it to the floor. She hadn’t ended up quite right, so I gripped her waist and guided her forward to position her bottom over my right thigh. She looked back at me with a touch of a smile on her face before returning her gaze to the floor in front of her. 

It suddenly occurred to me that Amy and I had not had any bodily contact whatsoever, let alone anything as intimate as this. My first inclination with a naughty girl over my knee was to rub her back, bottom, and thighs as I prepared her for spanking, but with no prior contact, it didn’t feel right. Nevertheless, she was expecting much more than soothing caresses from me at this point, so I laid my hands softly on her back and rubbed gently.

“Have you ever been spanked before, Amy?” I asked as one hand started over the rounded contour of her bottom.

“No, sir,” she replied, with desire.

“Not even as a child?” My roaming hand made it to her bare thighs and pulled her closer to me, spreading her legs just slightly.

“No, sir. Never.” I imagined her wanting to add, ‘So get on with it!’

“Well then,” I said as both hands gripped the hem of her skirt and slowly pulled it up over her back to reveal her sexy bottom in the tight white panties she’d given me a glimpse of before. “I’ll start with your panties in place and give you a chance to warm up.” My hands smoothed the few wrinkles in the taut white cotton through soft caresses and gentle tugs on the elastic, which already had her squirming a bit. “… but your panties will come down, and I will spank you on your bare bottom. Do you underSTAND?” I finished with a soft smack to the top of her right cheek.

“Yes, sir!” she replied excitedly. And so, the spanking began with a few soft smacks at a time, spread around her ample bottom, with ever-increasing force, yet gradually. Her tight panties kept her bottom contained, with only a slight wobbling resulting from the gentle spanking, but as the strength of my smacks increased, the rippling effect increased, as well as the soft moans and sighs from Amy. So far, she was enjoying it.

“Such a careless, naughty girl,” I scolded as the intensity reached the point where I’d typically start with someone experienced with spanking. “Has to be taken over my knee and spanked on her bottom to learn to do her job right!” I was spanking at a steady pace now, not stopping at all but still building up the force of my hand smacking her bottom.

I continued scolding her as the intensity built, and she responded with a quick ‘Yes, sir!’ here and there. “Yes, sir! Spank me!” she responded to one taunt. When she replied to one of my statements with, “I know, sir. Naughty girls deserve to be spanked on their bare bottoms!” I took it as a sign that she was ready to have her panties taken down.

I increased the speed and force for another ten spanks before I stopped and said, “That’s right, Amy. You need to be spanked on your bare bottom to be sure you get the message!” I said as I gripped the thin elastic waist of her panties and drew them down slowly, the elastic dragging over her warm behind. I said nothing, letting her savor the moment, the excitement and embarrassment of feeling her bottom exposed, and the growing vulnerability of her position.

Knowing I could see a sliver of her steamy pussy, a moist slit held tightly between her thighs, coupled with the knowledge that soon, she’d be feeling my hands assaulting the sumptuous flesh of her naked ass, which was already a lovely shade of pink, she was quivering with anticipation.

“You will be surprised how much more this will hurt, Amy.”

“Ohh, I’m sorry, sir! Do you have to spank my bare bottom?” The question was answered with my hand coming down for the first time on her naked bottom, making that unmistakable sound of a hand smacking a bare butt. I had backed off on the intensity from the last spanks over her panties but slowly ramped back up to where we’d left off.

The panties had contained some of the delicious jiggling and rippling of her fleshy bottom cheeks, which I appreciated as much as the feel of the smooth flesh against my steadily spanking hand. Her moans, sighs, and even cries belied the fact that she enjoyed it more. When her legs spread far enough to permit a view of her pussy, I could see the telltale glistening in her slit.

“Please don’t spank me so hard,” she’d cry, simultaneously lifting her hips in an invitation for more. Rounds of fast and hard swats to both cheeks would have her pushing her pelvis hard against my thighs, trying to escape my punishing hand, but as soon as I’d let up, she’d stick it up there, begging me to do it again! On and on, I spanked, waiting for some indication that she’d had enough, but every time I thought she was ready to stop, she’d beg for more in one way or another.

Finally, deciding myself that she’d been spanked long enough, from the sheer number as well as the redness of her gorgeous bottom, I started a long, continuous series of spanks on alternating cheeks, building force quickly and at the appropriate time stopped, and finished her off with three hard ones on each cheek spaced far apart.

“Oh, my poor bottom!” she cried, knowing it was over.

“Are you going to pay more attention to your work now?” I said, challenging her with an authoritative voice.

“Yes, sir! I will! I don’t want to get spanked again!” she replied, looking up at me with a hint of a smile that contradicted her statement. “At least not for a while!” she added with a smile as she rubbed her sore bottom most arousingly. 

“See that it’s a long while!” I said, getting the scenario back on track. “Up you go! Get your panties back on!” I quipped as I smacked her bottom again, playfully this time.

“Ooo, please stop,” she said as she got off my lap. She bent to pull her panties up from her ankles where they’d landed in all her gyrations across my knee and practically stuck her bottom in my face in the process. She turned to face me as she straightened the crotch out, at one point pulling them tight up against her pussy. She looked down at my crotch and couldn’t help noticing the bulge there since she’d arrived. She looked at me with sorry eyes, knowing it wouldn’t happen again. 

“You’d better get going before I decide you need more!”

“Yes, sir, and thank you for punishing me and not firing me,” she said as she went to the door and left.

I sat there for a few moments in a daze. I’d spanked girls before where it ended with the first spanking, but this felt different. I liked Amy and wished I could have done more for her to appreciate her first spanking, but that would be Brian’s job, and I knew that going in.

I got up and got ready to leave. I didn’t know if she would return, but I wondered where she had gone. I hoped she’d gone to the ladies' room to take care of that steaming wet pussy I’d left her with. The mental image of her satisfying herself wasn’t helping my situation, so I put it out of my mind and resolved to take care of myself when I got home. I finished straightening up, logging off my computer, packing my laptop, and headed for the door myself. Barely to the door, I almost barreled right into her, both stopping suddenly in surprise.

“Oh! I, um, I wanted to thank you, Mark. That was really amazing!”

“I’m glad you liked it. I hope Brian enjoys it as much as I did.”

“Me too! I still don’t know how I’m going to tell him, but I’ll think of something. Anyway, thank you so much!” she said as she hugged me, gave me a short, tender kiss, and turned to go after a quick smile. As she walked away, her hands went to her bottom, rubbing the sting out as she turned back to me with a smile, then a pouty face as she exaggerated her bottom rubbing.

‘Brian’s a lucky bastard,’ I thought as I watched her round a corner and disappear.

3 – Amy Wants More

By the time Monday arrived, I had accepted my position concerning Amy. I had left Friday feeling both happy for her as well as cheated; cheated in that were it not for Brian, I might have had a great relationship with Amy; at least, my romanticized view of the situation told me so. But Monday found me resigned to letting it be a fond memory and nothing more.

When Amy and I first encountered each other in the hallway, it was late in the day, and we were pleasant and friendly, but there was no indication that Friday had occurred at all, probably better for us both, and the week progressed in much the same way, with everything back to how it was … until Thursday.

It was, again, very late in the day when Amy came to my office to review the results of the most recent test she’d done. She did a good job running the test and interpreting the results. She wanted me to corroborate her findings, which I did and told her so. When she didn’t leave my office, standing at the side of my desk as though something was on her mind, I had to ask what was up.

“You know I really loved what we did Friday,” she replied with a look that said she had more to say.  “I loved getting spanked,” she added, looking me in the eye.

“I told you that you would,” I said, wishing she hadn’t brought it up again. “I’ve never known someone who thought they would like it and then didn’t after finally experiencing it. You’ll never forget the first time, and for that, I am grateful that I was the one to give you that memory.”

“Oh, that’s sweet! Thank you, Mark. I’m sure you’re right about not forgetting.” She still didn’t look like she was leaving any time soon, and after a short, unnatural pause, she added, “Still, I was surprised by one thing.”

“What was that?”

“It was exciting all the way through, and I was really aroused; you know, wet? But I didn’t cum while you were spanking me? I figured if just the thought of getting spanked could get me so horny, then surely the spanking itself would make me cum!?”

“I hope you weren’t disappointed?”

“No! No way! And besides, I took care of it. You know.”

“Yeah, I figured.”

“Yeah, so I mean, it was so good right from the start! The way you dragged it out, building anticipation all the while knowing what was to come and then taking me over your knee and spanking me! Once you started, it felt so good, even the hard ones on my bare bottom! I just figured it would eventually lead to, you know, an orgasm!? I even encouraged you to keep spanking me longer than I should have, thinking it was still coming.”

“I hope I didn’t mislead you. The truth is, it’s probably far more common not to cum during a spanking, especially on your first time.”

“Why is that?”

“It’s your first time! You don’t know what you’re doing. You don’t know what you like yet, so your partner can’t know either. There are so many scenarios, positions, and implements to try. You need time to figure out what gets you both going.”

“Scenarios? Positions? Implements?” she asked as though her head were spinning from the possibilities.

“Sure. For some people, the scenario is everything. They want to be punished by their teacher or their boss, Amy! They want to be caught doing something naughty, or what they did doesn’t matter as much as how and when they’re caught. For others, position is everything. Over the knee is by far the most popular, but bent over the teacher’s desk, over the back of the sofa, or lying on a bed with a pile of pillows elevating their naughty spank spot! And implements! That can really get involved with hairbrushes, paddles, straps, wooden spoons, canes, and others.”

“Wow!” she said as she moved behind my desk and leaned against it right next to me with that same intimacy that started all this.

“Usually, one prefers a certain combination. The naughty boy who wants to be caught by his teacher may want to be over her knee first but then progress to being bent over her desk for a dose of her ruler or paddle. Others in that same scenario, who’ve progressed to more painful punishments, aren’t satisfied unless it’s ‘six of the best’ with the cane on their bare bottom right from the start.”

“And all I imagined was a hand spanking over your knee!”

“I imagine most start that way. But in time, they experiment and find what’s really hot for them. Or perhaps they’re not comfortable saying right at first what their fantasy is. A naughty teenager spanked with her hairbrush over her daddy’s knee. A flirting boyfriend paddled by his girl while bent over the end of the bed. A husband arriving home late stripped naked, bent, and tied over a chair for a good strapping from his wife.”

“Jesus, Mark! You ought to write a book about this stuff!”

“And most of those will not cum during their most exciting fantasy! I can’t say for sure, but I’d guess most people never climax during the spanking, but they still love it and won’t do without it, partly because sex afterward is just amazing!”

“Really!? I mean, never?”

“Yes, and most of those who do cum during the spanking need some additional stimulation. Of course, that’s amazing too!”

“How does that work? I mean, what do you do?”

“Well, some girls get what I call a good spanking! She still gets spanked just as hard and long, harder even, but even though we’ve been pretending that she’s a naughty girl, at some point, she turns it around and admits how much she really loves getting spanked! Then the hand not smacking her naughty bottom can stimulate other highly sensitive parts of her anatomy,” I finished with suggestive eyes.

“Ooo, that sounds really hot!” she replied genuinely excitedly. One part of me said I’d better take the stimulation down, but another loved its noticeable effect on Amy. She wasn’t physically reacting, but her mind was squirming like crazy. I let the naughty side of my brain rule for the moment.

“Oh, it is! She’d usually be naked by this time so that I can touch her anywhere.” Amy was eating this up, and I felt almost sure I could talk her into another spanking with just a little more enticement, but my good side won out. “You should get Brian to do that for you!” I said finally, accepting that she’d not go as far as I suggested.

“Yeah, I guess,” she said, the gears spinning in her head almost visible. She stood up and knelt before me with the most irresistible pleading look. “Mark, I don’t want to wait for Brian.” My shock had to be evident, and I didn’t know what to say. 

“Amy, what are you …?”

“I’m saying I want you …,” she said with her pleading eyes boring holes right through my resolve, “I want you to give me a good spanking!”

“Excuse me? Is that a demand or a request?” I said sternly, knowing I was feeding the fire burning within her.

“I’m sorry, sir! Will you please give me a good spanking?” she pled even more convincingly.

“I don’t know,” I said, my feelings see-sawing back and forth. “That’s going quite a bit further, Amy. Are you sure you’re ready for that?”

“Yes, I’m sure!”

“And what would Brian think of this?” I said, assuming that mentioning his name would bring a dose of reality back to the conversation. I was wrong.

“Brian won’t know about it, and since I’m doing it to be sure I know what I want him to do to me, I think it’s all right,” she rationalized.

“So, ‘I’ll get Mark to spank me until I cum so I can leave him and get Brian to do it for me from now on?’ Is that your plan?” I said satirically.

“Oh, Mark. I’m sorry,” she cried, understanding dawning on her face. “You’re right. I would be using you, wouldn’t I? That’s so mean! I can’t believe I was gonna do that! I’m so sorry!”

“As well you should be,” I started sternly but continued softer, “And for being so inconsiderate, it might not be as good as you think, but you do need a spanking!” It took a second to sink in, but when it did, a smile started to form on her pretty face. “A good, hard spanking!” I added, knowing she’d fully understand what I meant.

“Are you sure?” she asked, her pretty brown eyes looking up at me.

“Am I sure you deserve to have that gorgeous bottom of yours spanked good and hard to a nice shade of red?”

“No, I am sure I deserve to be punished! I mean, are you sure you’re okay with doing it to me when … when we know it can’t go any further,” she said, getting sincere at the end, though hoping I wouldn’t change my mind.

“No, I’m not sure, and you shouldn’t be either! Am I sure whether I want to have you over my knee with that delicious butt of yours under my spanking hand while my other hand has free reign to play with your sexy body in any way I see fit? Yes! Absolutely yes! But am I sure my conscience can deal with Brian? I don’t know. Do we both agree that this is the last time before we start? Maybe, but I think we should both take a day to think about it and be sure. Okay?”

“Mmm, you think I have a delicious butt? … and a sexy body you want to play with?” she asked, enjoying the flattery and soliciting further compliments.

“Amy!!”

“Okay, okay! So, if we agree with those terms, we do it.  If either of us doesn’t agree, we don’t, right?”

“Yes, and before we give in to temptation before we intend to, I think you’d better leave.” 

She nodded her agreement and stood up, but before she turned to leave, I again felt her soft, full lips pressed tenderly against mine for a short but beautiful kiss. As we separated, I was treated to a beautiful but sad smile before she turned and headed for the door. I didn’t watch her leave as I was lost in the thought that this deliciously naughty girl might have been mine under other circumstances.

My reverie was broken when she called to me from the door. I turned and saw her bent over with her pants pulled down, taunting me with her sumptuous ass.

“You’d better be careful! You could get spanked for that!” I commented, saying the only somewhat clever thing I could think of.

“I’m counting on it!” she replied saucily, and at that point, I would have taken a bet that her mind was already made up and she would once again be across my knee for another spanking.