It didn’t surprise me that I couldn’t get Amy off my mind. A part of me was thinking I chickened out, not even willing to face her to say no, but another part justified that course of action by admitting to myself that I might have given in to her, and as the evening wore on, I began to wonder if I should have. It had been a while since I’d been on the receiving end of a good spanking, a long while, and the more I thought about it, the more I wanted it.

As I lay in bed, unable to sleep with it still on my mind, I decided that if my feelings hadn’t changed by morning, I would take Amy’s spanking if she was still willing to give it to me.

6 – Amy Needs No Lessons

I woke up feeling no different and quickly began anticipating the whole scene, especially the spanking. As the day continued and I didn’t see Amy, I began to worry if I’d missed my chance. Did she take my not being in my office as a brush-off, or was it just a coincidence? I saw her from a distance, not face to face, which increased my anticipation and worry even more.

Finally, in midafternoon, we did come close enough to say ‘hi,’ and I suspected she had not given up; in fact, she was dressed to tease, wearing a short, flouncy skirt in navy with matching stockings and a tight, white blouse that could be both sexy and severe, plus heels higher than any I’d seen her wear before. 

Any doubts I had were gone. I was reasonably sure she’d continue the upskirt scenario, and I couldn’t wait to get my face up that skirt between those luscious thighs and spanked good and hard for it.

I only worried that Amy’s first attempt at this dominant role would fall short of my expectations. To some degree, it was up to me to give her directions without destroying the scene. I couldn’t stop and say, ‘No, spank right here and do it harder,’ or ‘Now bend me over the chair and use your hairbrush.' At least not if I wanted the scene to continue with any arousal remaining.

I assumed she wouldn’t need any direction when my face was between her thighs as I certainly knew what to do there, and she only had to react. Enjoying it obviously wouldn’t be a problem, but the dominant aspects of it may be. I thought I knew how to direct her without leaving the scene, but I was getting increasingly impatient, waiting for the chance to try.

It was a little before five o’clock when she entered my office and sat down as though I was expecting her. Crossing and uncrossing her legs gave me quick glimpses of black panties, tight and sheer if I wasn’t mistaken, but more importantly, bare thighs just above the hemline, which hopefully meant a garter belt holding her stockings up.

“So, did you review those test results I sent you,” she asked as though we were back in the days of testing my program. 

“Um, I don’t know what …”

“No, of course you didn’t! Too busy looking up my skirt, weren’t you!? … and probably every other skirt in the building!” she said, feigning anger.

“Amy, I’m sorry. I didn’t mean to …”

“You didn’t mean to look up my skirt?” she accused as she stood up. Going to the side of my desk, she hoisted herself up on the short file cabinet that left her sitting just a bit below eye level from my seated position behind my desk. As my eyes shifted between her face and her thighs, between which I could again see her panties, she said, “Of course you meant to look up my skirt! You’re doing it now! Look me in the eye!” As I did, she said, “Now I’m going to spread my legs nice and wide, and you see if you can maintain eye contact with me and resist looking!”

“Oh my," I whined as I looked into her eyes, aware of her legs separating and fighting the urge to look below. There was a smile in her eyes, if not on her face, as she realized I was going along with her scene. Of course, she didn’t really want me to pass her little test, but I gave it a good try just the same.

Holding off had the added benefit of her spreading her legs ever wider, open to my gaze, so when I finally gave in to the impulse to look, I was rewarded with the all-time best upskirt view ever; sheer black panties that, even in the limited light available, revealed her bald pussy beneath, and confirmation of my earlier hope of a garter belt holding up her sheer black, lace top stockings.

“Oh my God, Amy!” I managed to say before she snapped her legs shut and stood up again. When she walked towards the door, I was afraid she’d go, leaving me all wound up at the beautiful vision I’d just seen, but she only wanted to close the door. After doing so, she came around the desk, and I rolled away as an instinctive defensive move. She sat on my desk with one leg on the floor and the other folded in front of her.

“You know I could probably get you fired for this? At the very least, extremely embarrassed!”

“Amy, please don’t do that. I won’t do it …”

“Won’t do it anymore? Is that what you were going to say? Only if I keep my legs closed up tight so you can’t see anything!”

“No, really! I’ll try to …”

“I don’t believe you could! You can’t resist the temptation, can you? Don’t worry, I’m not going to tell anyone.”

“Thank you, Amy! I promise I won’t …”

“Not so fast! This doesn’t mean you’re getting off without consequences!”

“What consequences?” I asked, dying to hear her tell me what she would do to me.

“You still need to be punished. We’ll start by taking your pants down and putting you across my knee for a spanking on your bare bottom!”

“A spanking? On my bare bottom?!” I said, trying unsuccessfully to feign shock and surprise. Amy smiled at my reaction, adding to her pleasure of having the upper hand in this situation.

“Yes, a spanking! A good, hard spanking!” she replied, breaking character with a friendly smile.

“Where will you, um, when …” I said, looking around the room.

“I ought to do it right here and now; you certainly deserve it! But we’d probably attract some attention we don’t want, so you can relax a little. But we will leave right now and go to your house, and once there, I won’t waste any time getting you over my knee for the punishment you deserve: a bare-bottom spanking and anything else I can think of that would be appropriate!”

She stood up, giving me another good flash of her crotch, and catching me, she said, “See, I knew you couldn’t resist! Maybe a sore, red ass will make you think twice about looking up girl’s skirts!” I doubted it, especially if the ‘anything else’ she could think of was what I thought! “We’re leaving now!” she ordered.

I quickly shut down my computer, grabbed my backpack, and got up to leave. Looking at Amy for instructions, I assumed she’d have some, but apparently not.

“Are you going to come with me or …” I started.

“No. I don’t want to be seen with you! I’ll follow you, but don’t waste any time getting there!” she warned.

We went our separate ways out of the building and to our cars. The hard-on I’d developed upon that wide-open view of her crotch was ebbing a bit, but I was glad we wouldn’t do this in my office. It would be much better not to worry about being heard or caught outright, and my house was the logical choice since she still lived with her parents.

I drove towards the exit but waited for Amy to pull up behind before driving out. Looking at her friendly face in my mirror, I thought about her sitting in her car with her legs spread and that delicious pussy anticipating my tongue. As I started getting hard again, I hit the gas and sped up from the pokey ‘follow me’ speed I had been going. Amy followed me easily, and we reached my house in less than ten minutes. I pulled into the garage; Amy parked behind me and followed me into the kitchen through the garage door. 

“Nice house,” she said, “Too bad we don’t have time for a tour!”

“I’d be happy to give you one,” I offered genuinely, thinking she might decide which room we would use.

“Are you stalling?” she accused as she looked me straight in the eye, “Maybe, but I guess your naughty bottom can wait a few minutes to get what’s coming.”

We started downstairs, going through the living and dining rooms, then the bedrooms, and ultimately the main bedroom, where we’d be taking care of my punishment if it were my choice. A high king-size bed, a straight-back wooden chair, and an oversized, upholstered chair with its ottoman all served as perfect props over which one could lay, bend over, or kneel upon to receive what I had coming.

It was no accident that this furniture was so suited to these tasks. I even left the wooden chair in an unlikely but provocative position, just waiting to be used for an OTK spanking. I doubted Amy would pick up on any other suggestions, but the chair caught her eye as she stared at it and then smiled at me as we left.

We went upstairs, where I had an office. The office was another bedroom suite with its own bathroom, but I had set it up as an office for business use and another setting for spankings. It also had an upholstered chair and ottoman, plus two chairs similar to those in the bedroom. The desk was kept clear so it could also be used as a prop.

I didn’t show Amy the closets, one of which held my collection of implements, including many paddles, most of which I’d made myself, and a few straps, hairbrushes, and floggers.

Amy took it all in, and I imagined she saw the possibilities as her first spankings had taken place in an office setting, though, as I suspected, she didn’t want to use that setting with me.

“Very nice, but no more stalling!” she said, returning to character. As I turned to head for the stairs, she gave me a swat on my bottom, saying, “It’s time for your spanking, and I saw the perfect chair to use in your bedroom!”

“You’re really gonna do this?” I questioned as we stepped down the stairs.

“Yes! I am! You need to learn that a short skirt and shapely legs are not an invitation for you to ogle a woman’s panties and crotch!” When we reached the bottom of the stairs, Amy took my forearm and pulled me towards the bedroom. Once there, she went straight to the chair and, turning her back to it, pulled me around to face her. “Now, take your pants down!” she ordered as she sat. I quickly opened my pants as I have done in similar situations many times before, pulled them down, and released them to fall to my ankles.

“Look at that! Still hard from that view up my skirt?” she challenged, seeing the bulge in my tight underwear.

“Um, I guess so,” I replied sheepishly.

“Well, we’ll see how hard you are once that bottom of yours is good and sore!” Assuming she’d meant what she’d said earlier about only spanking me bare, I reached for the waist of my black bikini underwear. “Hmm … nice undies! Maybe you should leave those on for now. After a nice, hard warm-up, we’ll see how red your bottom is! Now, over my knee, you naughty boy! You’re getting a spanking!” With my pants still around my ankles, I shuffled to her right side and bent over to lay across her knee.

We both shifted around a bit to get comfortable, after which Amy tugged at the legs and waist of my underwear while smoothing the shiny black fabric over my cheeks as I anticipated the first delicious swats of her hand on my deserving backside.

“I’m sorry, Amy! Please don’t spank me!” I pled for her benefit alone.

“Apologies are meaningless if you don’t stop what you’re apologizing for!” she said kindly but added with venom in her voice, “Trying to see my pussy!” And with that, the first couple of swats fell, one on each cheek. “You need a spanking!” she said as the spanks rained down on my covered bottom.

“Ow! Amy! Please stop!?” I cried, still trying to amp it up for her sake. Truthfully, if it weren’t for the fact that I hadn’t been spanked in a while, I might not have liked it at all. She kept a steady rhythm, but it was a bit too random, not letting any sting build up. Still, I loved being over her knee with her scolding me, telling me what a naughty boy I was and how she would teach me a lesson with a good spanking. I looked forward to the point when she’d pull my underwear down, and I’d feel her hand on my bare bottom.

Amy continued, taking a few rests here and there to give my not-very-sore bottom some soothing caresses. Again, they felt good, but they’d feel much better if there was some pain. Still, I let her go on, raising my bottom to meet her hand, hoping she’d take the hint. Not sure if she got it or just decided on her own, but it was finally time for a bare bottom.

“I don’t think you’re learning your lesson like this. I want these underpants down!” She gripped the elastic and pulled as I raised my hips to let her take them down. She left them bunched around my thighs as her hands roamed over my naked cheeks. “Such a naughty boy! Needs to have his bare bottom spanked to learn he shouldn’t look up girl’s skirts! Don’t you!?”

“Yes, Amy. I’m sorry. Please don’t spank me too hard?” I pled, hoping she’d do just the opposite. Unfortunately, she did not. Again, she spanked somewhat randomly, and though it felt better on the bare, it was still not hard enough to make the pain pleasurable. I let her get in a couple of good volleys before saying, “Thank you for not spanking me so hard!”

“Oh, really!? I guess I’m not spanking hard enough because I certainly intend to make your bottom hurt!” That did the trick. Suddenly, she was spanking a lot harder, and she’d figured out that a bunch of spanks in one place hurt even more. Now I was getting spanked! And I let Amy know it with plenty of squirming and moaning about how hard she was spanking me. She soon felt the effort she was putting into it and stopped for what I was sure was rest. “So, how does it feel now, hmm? Does your butt hurt now?”

“Yes, Amy. Please don’t spank me anymore! I’ve learned my lesson. I won’t look up your skirt anymore!”

“Oh, I doubt that! But I have something else in mind besides spanking your bottom to help you learn,” she said as she resumed spanking with alternating smacks on the fleshiest part of my cheeks. After at least thirty spanks, fast and hard, she stopped again.

“Get up!” she ordered, lifting my arm to confirm that she wanted me off her lap, “That’s it. Now, kneel right here in front of me!” I did as she asked and looked up at her from my subservient position to see pretty Amy looking down at me with a friendlier smile than the scene called for. Apart from being a little disheveled due to the recent activity, she looked pretty much as she had earlier.

When I looked down at her thighs and noticed them closed up tight, she said, “Don’t worry! You’re going to be up close and personal in just a minute! If you can’t control yourself looking up my skirt, perhaps I should hold you captive between my legs, with your face stuffed in my wet pussy! Maybe if you have to see, smell, and taste it long enough, you won’t be so anxious to see it again!”

In answer to her statement, I put my hands on her knees, saying, “May I?” as I tried to pull them apart. She resisted, so I took my hands away.

“Not yet. You need to understand some of the rules first!”

“Rules?”

“Yes. I know you’d love to get your tongue in my cunt, but that’s not what we’re here for! It’s to make you eat so much pussy, you’ll think a little differently the next time you think you want a free glimpse. So, you will make me cum with your fingers and tongue, and after that, you’ll go back over my knee for another spanking. How hard and how long I spank you will depend on how well you made me cum!”

“If I give you the best pussy licking ever, will you stop spanking me?”

“No, you are getting spanked again, and after that spanking, you’ll eat my pussy again! Then you’ll get spanked again, and so on, until I decide you’ve satisfied me sufficiently to stop spanking you! Do you understand?” she asked with the same out-of-character smile.

“Yes, Miss,” I replied, and as if that was the password to get in, her thighs spread slowly open, revealing her naked crotch. Somewhere along the way, she had taken her panties off!  “Oh, Amy! How can you blame me for wanting to see such a perfect little pussy!” Her face beamed from my compliment, but she couldn’t acknowledge it, given the current scenario.

“Mmm, why don’t you get naked before you lick my perfect pussy!” I pulled my shirt off quickly, anxious to get between those thighs, not worrying about the socks I was still wearing.

As I slid my hands up her thighs, she shifted forward a bit so that she could lay back and enjoy what was to come. My lips followed my hands, kissing their way up the inside of one thigh, only to stop at the moment of truth and do the same for the other. This time, my lips contacted hers, kissing and licking the soft pedals of her sexy flower gently but unrelentingly. She was soon unable to contain her reaction, and her hips rose to press the warm, wet flesh into my face. Already quite wet, she smeared her juices all over me as I pushed back and let her wipe my face with her pussy.

With that, I probed her juicy pussy, my fingers, tongue, and lips, starting gently but quickly increasing to frenzied activity on, in, and around those delicious swollen lips. I stroked, nibbled, poked, and licked until Amy was writhing in the chair. I’d bring her to the brink, only to pull back and start over again, but after two or three such cycles, I decided to push her all the way.

As we accelerated towards the finish line, Amy pulled my head into her crotch and clamped her thighs down to hold me there as my tongue and fingers stimulated every nook, cranny, fold, and crease of her cunt. She went over the edge in no time, gasping and moaning while still holding my face to her crotch.

She released me from my delicious prison between her thighs and sat up, trying to regain her composure. I sat patiently in front of her as though awaiting a verdict, which, in a sense, I was, wanting to know if she liked it, even knowing I would be spanked again anyway. She gradually came back to life and sat up straight.

“Well … that was … good, but not good enough!” she commented, struggling to stay in character. She couldn’t resist a telling smile that said she’d never quite had something like that before. “You may have earned a slightly lighter spanking, but not much. You’re still going to be spanked good and hard across my knee!” she said, regaining her authoritarian attitude.

"Yes, Miss. Do you want me over your knee now?" I replied, trying not to smile myself.

"No, get me my handbag first. I want my hairbrush nearby and ready!" I looked around to see she had tossed her bag on the bed, retrieved it, and gave it to her. Slipping her hand inside, she quickly found and withdrew the large brush I'd used on her before. "There it is. That ought to put a little extra sting into that naughty bottom of yours!"

"Please don't spank me with the brush, Amy!"

"I won't start with it, but if I don't feel I'm getting through to you, I won't hesitate to use it! Now get back over my knee!"

I got myself into position with Amy's hand stroking my somewhat tender flesh in a manner meant to arouse. I thought to myself that for a beginner, Amy moved back and forth between pain and pleasure well. She needed some coaching on the actual spanking but had role-play down to an art. When I felt her hand leave my butt, I knew it would return quickly in the form of a spank. "Now we'll see if you learn your lesson after another spanking!"

There was no warm-up this time; Amy started with a fury, resulting in a series of spanks to the fleshiest part of my buns and a building burn. It was much better than the prior series in that there was a definite sting right from the start, and it got worse or better, depending on your point of view. I had been looking forward to her brush, but now I wasn't so sure. Amy delivered two extended series of spanks, nearly a hundred total, before stopping to pick up her brush. I felt the wooden back of the brush stroking my cheeks before I realized she'd picked it up.

"No, Amy! Please! Don't spank me with the brush!" I cried, only partly now for her benefit.

"Ohhh, I'm sorry! Does your poor little bottom hurt? Hmmm? Well, I’m sure it doesn’t hurt enough, and this brush will make sure it does!" With that, the brush came down with a short series of tentative swats. Reading my reaction correctly, she stepped up the force she was using as the brush again punished my sore bottom with a dozen pretty hard spanks.

After a brief teasing about the color of my bottom, she began even harder again, getting the reaction she was seeking as I squirmed and moaned in genuine, delicious pain. That series lasted for ten or more swats and was followed by an even more punishing round of another twenty or so before she stopped to give my tortured cheeks some soothing relief with her gentle hands. 

"Ooo, such a hot little bottom! Is my naughty boy starting to learn his lesson?". When I didn't answer, I was prompted by a hard smack of the brush. "Well?" she demanded with another hard smack.

"Oww! Yes, Miss! I'm sorry! I won't look up your skirt again!" I lied.

"Oh, poor baby! You don't really think I'm going to stop now, do you?" Not responding to her rhetorical question, I groaned as the brush resumed beating on my bottom. After another round, she stopped, and when I saw the brush fall to the floor, I knew this would be more than just a short break in the spanking action. "Are you ready for another chance to redeem yourself?"

"If that means I get to bury my face between your delicious thighs, then yes, I'm more than ready!"

"Yes, it does, but remember! Same rules! If you don't make me cum the way I like it, you get an even harder spanking than the last! You will get spanked either way, but I may go a little easier on you if I like what you do to me."

"May I get up now, Miss?"

"Very polite. That's better. Yes, you may get up now." As soon as I was out of her way, she got up and went over to the bed. She removed her skirt to get it out of the way and opened her blouse to expose her sexy, lacy bra with her just-right tits threatening to spill out the top. After pulling her blouse open to offer a better view, she sat on the bed, laid back, and raised her knees up and apart, inviting me into her inner sanctum.

"This time, I want to see how fast you can make me cum! And you’re getting a head start because I'm already soaking wet from before and spanking your naughty bottom."

"Do you like spanking me, Amy?" I asked as I knelt in front of and between her splayed knees.

"I think I do! I like how you listen and do whatever I tell you, and I love seeing your sore, red bottom bouncing around when I spank you! Now, what I want to see is your face between my thighs and your tongue in my slit!" she said as her hands reached for me and pulled my face hard against her sopping wet cunt.

Extending my tongue as I made contact, I got Amy moaning at the outset. I suspected she was right that it wouldn't take much to get her to climax, so I set myself a more challenging goal of making her cum twice before I was done. It took only a bit of tongue sliding through her slit and tweaking her clit to make her cum the first time. She groaned in appreciation of my speedy work but was surprised to find my mouth still attached to her cunt, going for the second climax.

Surprised though she was, she certainly didn't stop me as her squirming on the bed gave me all the approval I needed to continue. Trying for a sensory overload, I employed multiple fingers as well as my tongue, lips, nose, and chin to quickly build her excitement up again.

Trying something new, I gently pushed the tip of my finger into her bottom, and her immediate reaction told me I should continue. Adding two fingers in her pussy and my tongue licking and flicking her clit, her arousal accelerated quickly, and in less than a minute, she was cumming again, almost violently, as I felt like she'd tear my head off with it again gripped tightly between her thighs.

"Oh my God!" she cried repeatedly as she gradually emerged from her climax. Once released from her vice grip, I gently stroked, kissed, and licked all I could reach, eliciting random shivers from Amy’s body. “Oh my God, Mark,” she repeated, “That was amazing! I can still feel it!” She sat up and, moving to the edge of the bed, hugged me with my face pressed against her chest.

“Does that mean you’re not going to spank me again?” I asked as I kissed and licked her bulging breasts.

“Ohh, I’m sorry, baby, but no … you still have another spanking coming. A good spanking, I think!” she said with a smile. She stood up. “Come over my knee, you deliciously naughty boy!” she added, returning to the chair, “You’re gonna get a spanking on your bare bottom … a good spanking!” 

"And what is going to be good about this spanking?" I asked as I again placed myself at her mercy across her lap. As I lowered myself, she took hold of my stiff pole and ensured it ended up between her firm thighs, where a few squeezes demonstrated her grip on me.

"Well, first, it's a spanking, isn't it? ... and I suspect you like getting spanked, hmm? Admit it! You like being over my knee getting smacked on your bottom, don't you? Bent over my knee like a naughty little boy, getting a good spanking?"

Without waiting for an answer, she resumed spanking me, though with a decidedly pleasurable feel; hard enough to hurt without being malicious, varied sufficiently to reheat my entire backside, and fast and long enough to build an allover sting quickly enough. "So, we'll just see what else we can do to make it a good spanking, okay?"

"Yes, please, Amy. Ohhhh!" I gasped as she gave me a bunch of swats on one cheek in just a few seconds and repeated it for the other cheek. I hoped the "good" part would include getting me off as well, and since she'd been willing last time, I didn’t feel I was getting ahead of myself imagining how she would do it. I was more than willing to take another turn between her thighs for motivation.

Speaking of motivation, to give me a little more, she bent down to retrieve the hairbrush, and very quickly, I felt it being applied to my bottom, though for variation rather than severity. At the same time, I felt her thighs rubbing together as much as her position would allow, my moaning showing my appreciation of the friction my cock enjoyed.

Correctly sensing that I would be approaching a climax soon, Amy started what felt like a finale with flurries of spanks from her hand and the brush plus additional stimulation from her thighs squeezing my cock and her free hand touching anything it could, running up and down my crack feeling particularly good. Settling into a pattern of solid swats to the crown of my buns, combined with a steady milking of my dick, she brought me to a shuddering climax spewing my seed on the seat and, inevitably, some on her thighs.

"Mmm, was that a good spanking?" she asked, fishing for compliments.

"Yes ... oh yes!" was all I could manage for a reply until my body calmed down a bit. "Oh, Amy, I insist on repaying you for that fantastic spanking!"

"Oh, I haven't finished with you just yet, you naughty boy! Come. Get up," she said as she patted my stinging bottom playfully. I slowly lifted myself from my favorite position and stood up, aware this may be my last turn across her knee. She stood up as well and, placing her hand again on my hot bottom, guided me towards the bed with gentle but firm pressure on my cheeks.

~~~~^~~~~

Think Amy knows what she's doing? If you enjoyed my story, please 'like' and/or 'favorite' it! Thank you!