The Disciplinarian: A Collection of Short Spanking Stories Page 5

  "Andrea?" came Tanya's voice as she approached. The look on her face wasn't what I expected though. In fact, her glare was directed at Jason Drummond and not at me at all. "Mr. Drummond, is everything ok?" she asked him but turned to me when she did.

  "Sure is, Tanya. Your very friendly staff just recommended this bar to me."

  "Ah," Tanya said, her gaze still on mine. "Well, Andrea is one of our best employees. Don’t you have an early shift tomorrow, Andrea?" she asked, checking her watch.

  "Yes, ma'am," I said, both relieved at her interruption but afraid of the consequences I knew I'd have to face.

  "You'd better let her get home, Mr. Drummond. Andrea has a long day ahead of her tomorrow."

  I took that cue and pulled myself free of him, quickly adjusting my skirt and fishing out the car keys from my purse.

  "Have a nice night, Mr. Drummond," I said.

  "Everything ok here?" the GM stopped to ask. He was in his late forties but I'd had very little interaction with him. "Isn't that…"

  "Everything is just fine, Thomas," Tanya said. "Nothing I can't handle. Andrea, 8:00 AM sharp in my office, please."

  "Yes, ma'am," I managed, nearly running to my car. The three stood watching me as I started the engine and drove off, my heart racing, feeling completely stupid at my naiveté now that I understood what Jason Drummond was all about and I realized that I may have lost my job tonight. Well, I'd find out soon enough.

  Chapter Three

  My shift started at 7 AM. Tanya was already in her office when I walked in at quarter-to-seven, my uniform in perfect condition. The first thing I did was look through the pile of checked out guests, relieved to find that Jason Drummond had already left. I had been so stupid. He was good looking, older, a successful businessman and I had let myself believe he wanted to have a relationship with me whereas last night only proved the opposite. He wanted to get into my pants and that was it. He traveled so much, I wondered how many other women he had all over the US.

  But I pushed those thoughts aside because pretty soon, I'd have to face Tanya and probably beg her not to fire me. But even if she would give me another chance, would the GM? No way.

  The first hour went by quickly with guests lined up to check out. A third desk agent came in a few minutes before eight and I realized Tanya must have called her in to cover for me. Michelle gave me a pitying look when I checked my watch and prepared to go to my doom.

  At 8:00 AM exactly, I knocked on Tanya's door.

  "Come in," she called out.

  I went inside slowly and closed the door behind me. She wasn't alone. Across from her sat the General Manager.

  "Come in and take a seat, Andrea," Tanya said.

  Mr. Raines cleared his throat as I sat down on the wooden chair set before her desk.

  "Let's not beat around the bush, we all have busy schedules. I'd like for you to explain to us what you were doing with Mr. Drummond last night please. Truth, Andrea. You'll get one chance."

  I glanced at Mr. Raines who watched me with a stern look.

  "A few weeks back, Mr. Drummond had asked me for some information on the area and, well, I met him for a drink and…that was all. We weren't dating or anything," I quickly supplied.

  "I'm glad to hear that because you do know he has a wife back home, right?"

  "A wife?" I asked, shocked.

  "A wife."

  "I didn't know, no."

  "I don't suppose he told you that part," Tanya said.

  "Our policy is very straightforward in these matters, Andrea," Mr. Raines started. "If it were up to me, you wouldn’t have had to come in at all this morning, but Tanya here has asked me to let her deal with this herself," he finished.

  I glanced from him to Tanya and back. "I'm not being fired?" I asked.

  "That depends," Tanya said.

  Mr. Raines stood. "I'll take my leave. Let me know how it works out, Tanya."

  "I will. Thank you Thomas," she said.

  We waited until he was gone and we were alone.

  "You're in a great deal of trouble, young lady," Tanya said. "I've put my own neck on the line to save you and I hope you'll be smart about what I’m going to offer you."

  "I’m sorry, ma'am. I really…I feel so stupid."

  She nodded. "Well, it isn't the first time a man fooled a young, naïve girl and it won’t be the last."

  I had turned twenty just two months ago, but she was right. I had been naïve.

  "If you want to keep your job here, you'll need to promise never to see him or any other guest in that capacity again," she began.

  "Oh, I promise. I won't make that mistake again."

  "There's more, don’t be so quick, Andrea," she said, opening a desk drawer. From inside it, she retrieved several items one by one and laid them all on the desk before me. I stared, trying to make sense of what was happening. "Mr. Raines and I both believe in old fashioned methods of discipline," she said. "Do you know what these are?"

  "I…I think so," I said. Before me sat a long rectangular paddle with holes drilled into it, a coiled up black leather worn looking belt and a long, flexible looking cane.

  "Do you know what corporal punishment is?" she asked.

  I swallowed, my heart racing, my breath catching, my sex suddenly throbbing. It was a similar feeling to when she'd had me stand in the corner but much more intense.

  "Yes, ma'am."

  "Good. My proposition is this: if you'd like to keep your job here, you submit to being physically chastised for your transgression."

  I only stared at the items for a long while.

  "Andrea, I am doing this for your own good. It's better you learn your lesson this way than have the next Jason Drummond come in and take advantage of you again. You're young and you have your whole future ahead of you. I hate to see you screw it up the way so many others have before you. Now do you agree to submit for punishment?"

  I looked up at her. "You'll do it?" I asked.

  She nodded. "Yes. We'll have a total of three sessions as I understand you saw Mr. Drummond three times, is that correct?"

  "Yes, Ma'am."

  "The first two will be administered by me in my office and the third will be administered by Mr. Raines. All spankings will be delivered on the bare."

  "Bare?" I asked, processing. "Even in front of Mr. Raines?"

  She nodded. "Those are the terms," she said, taking a piece of paper from the printer. "If you agree, sign this contract. If not, please pack your things and leave the property."

  "I can't lose my job," I said, just touching the paddle on the table.

  She reached out and put her hand over mine. "Andrea, I didn't have anyone do this for me when I was your age and I regret it now. The discipline will be painful, but you'll learn from it."

  I looked at her, wondering if she herself had been hurt when she was younger? If that was why she was cool and distant.

  I nodded. "I'll take what you're offering," I said. "I will submit to being physically punished."

  Tanya handed me a pen and I signed my name to the contract giving her permission to discipline me in this manner. Once I had, she filed it away and turned to me, both her expression and her tone stern.

  "Stand up, please," she said.

  I did, my legs trembling.

  "You'll take your first session today, the second tomorrow and the final on Sunday. We will start with the paddle and the belt, and the cane will be used only on the final day. The belt will be used to warm you up before your paddling. You'll have no warm up for your caning."

  "Yes, ma'am."

  Tanya rose and began to clear off her desk. She left only the belt and the paddle on it and turned to me. "Remove your stockings please," she said, picking up the belt. I watched as she unrolled it then doubled it over and took the buckle into her hand.

  Without hesitating, I reached beneath my skirt and pulled my stockings off, taking off my shoes to step out of them. Tanya held her hand out and I handed them to her before slipping my
shoes back on.

  "Step to the desk and lower your panties," she said.

  I swallowed and took that step so that my thighs touched the front of the desk. I then reached beneath my skirt again and pushed the white cotton panties I'd worn down so they pooled around my ankles.

  "Raise your skirt until I tell you to stop, please," Tanya said from behind me.

  I did so slowly, facing forward all along, feeling cool air on my bottom as I bared it for Tanya to see. When I'd pulled it up so that even my low back was exposed, she told me to stop.

  "Tuck the hem into the waistband so it stays there."

  I did.

  "Bend over the desk, rest on your forearms and arch your back."

  "Yes, ma'am," I said, taking my position, the feeling of lifting my hips somehow arousing to me even as I knew it only made a better target for her belt.

  "Good. Now stay still and do not rise until you're given permission."

  "Yes, ma'am."

  I felt her line up the belt first, then, before I knew it, she struck, catching me by surprise even though I knew it was coming. I gasped but remained as I was and she struck again. I bit my lip so as not to call out but it was nearly impossible not to when she rained down stroke after stroke. She took a break for a moment, telling me to widen my stance and waiting until I had. She then spoke about choices and consequences and a lot of things I just can’t remember anymore. My tears left spots on her blotter before she was through warming me up and all I could think then was if that was the warm up, I'd never survive the paddling.

  "First part is over," she said, coming close, inspecting my bottom, her touch making me flinch but also soothing as she rubbed my burning cheeks. "Nice and pink. Straighten and move to the center of the room," she said.

  I moved while I watched her set the belt down and pick up the paddle.

  "There is good, now bend over and put your hands on your knees. I want you nicely stretched for the paddle. You'll take six strokes today and six more tomorrow. Now bend deep, legs together."

  "It hurts so much already," I said, looking up at her from my bent position.

  "Punishments, by nature, hurt. Now bend deep and look straight ahead. Count them for me," she said, standing behind and just to the side. I felt the cool, smooth wood of the paddle as she lined it up and she didn't waste a moment before bringing the wood down hard on my already punished, sore bottom.

  "Ow!" I called out, unable not to. "One, ma'am."

  "Now, your colleagues will likely be curious about the noises already so you may want to try to stifle your cries." She struck as she said it, giving me just enough time to call out the count before the next one landed, keeping up this swift pattern throughout my first ever paddling. By the time I called out six, tears streamed down my face and my hands were wrapped tight around my thighs.

  "Stay as you are," she said, moving to place the paddle on her desk. When I thought my humiliation was over, she stepped behind me. I didn't move, instead, I became very aware of the moisture between my legs at the thought of her looking at me, at her having just disciplined me.

  "Widen your stance, please," she said.

  My face burned and I knew she'd know I was aroused the moment she saw my pussy. But I had no choice. I turned back to see what she had in store. I couldn’t take any more pain. But pain wasn’t what she had in mind. Instead, she caressed my burning cheeks before pulling them apart, her gaze curious as she looked at what she had just exposed.

  “Some girls become aroused even during a painful punishment like that," she said, just touching a hand to the moisture at my inner thigh, too close to my pussy. "I had a feeling you would be one of them," she said, pulling wider, her thumb coming to the space just beside my back hole as her other hand reached underneath and two fingers traced over my swollen clit, to my pussy and up, smearing my own juices all over me, the sensation of having her fingers on me more pleasurable than I wanted to admit. "Perhaps we'll need to punish this very tender place next time," she said, tapping on my bottom hole.

  I swallowed, having nothing to say, too embarrassed to speak.

  She patted my bottom. “Straighten up and go stand in the corner," she said. “Keep your skirt tucked up so that your punished bottom is on display. Hands at the back of your head. I have a meeting to attend but I'll set the alarm and I'll expect you not to move from that spot until it goes off. You may then return to your duties. No panties or stockings though, Andrea. I'll expect you here tomorrow promptly at noon for your next session."

  "Yes, ma'am," I said.

  "Good." She turned to gather her things. "Corner please."

  With that she left, leaving me standing in the corner, my pussy wet, my ass on fire, my pride nonexistent.

  Chapter Four

  At noon the following day, I stood at Tanya's office door. I had only seen her once that morning as she'd been tied up in meetings. I was unsure of how she would be and hoped no one would learn of my degradation. But it was as if nothing had happened and I would have thought myself that I’d imagined it except for the painful bruises on my backside. Tanya was completely normal to me, I didn’t even have to call her ma’am. At least not in front of the others. That was a small relief but I knew that I still had two sessions to get through, one with Mr. Raines taking the cane to my bare bottom. Why the thought aroused me as much as it frightened me I still hadn't made sense of. In fact, when the timer had gone off yesterday, I'd gone directly into the bathroom and within moments brought myself to orgasm.

  I knocked on Tanya's office door and heard her call for me to come in. I stood just inside the door as I usually did while she finished whatever she was doing and looked up at me.

  "Come here," she said, rising, retrieving the paddle, the belt and what I knew to be a butt plug. "I don't have much time today, Andrea, so we'll get right to your punishment, but I did plan ahead so you won't miss corner time. Strip from the waist down and bend over the desk please," she said as she opened the tube of lubricant and began to smear it onto her fingers.

  I watched her smear lubricant over the plug while I slid my stockings and panties off.

  “Skirt too and bend over the desk,” she said.

  I obeyed, my eyes on the lubricated plug.

  "Face forward, Andrea, but reach back and spread your bottom cheeks apart for me."

  Her final words made the humiliation of yesterday's paddling pale in comparison. "Ma'am?" I asked.

  She met my gaze, the expression in her eyes annoyed and out of patience. "I told you yesterday I would punish your bottom hole, didn't I?"

  "Yes, ma'am, but…"

  "I have a meeting in fifteen minutes, Andrea. Let's get this over with. Spread your bottom cheeks apart. I'm going to plug you first before I paddle you and you'll keep the plug in until the end of your workday. You'll appreciate my liberal use of lubricant here but if you hesitate, we may run out of time for that."

  I looked at the plug, then down at the desk where she had laid the contract I had signed yesterday before my nose. I reached back and tentatively pulled my bottom cheeks apart.

  "Wider please," she said. I already felt the drops of lube slide down my cleft and pulled them farther apart, giving Tanya access to my back hole.

  "Good," she said, her fingers smearing the stuff down and over my asshole. The sensation wasn't entirely unpleasant as she circled the tight, virgin ring, and I found myself gripping my bottom harder as she slowly began to press against my entrance.

  "That's it, Andrea," she said, sliding a finger into me. I tensed everything at the intrusion but she stilled and waited for me to calm down and relax my muscles before proceeding. Once I had, she pushed deeper, slowly beginning to smear the stuff inside me while she pumped her finger in and out slowly. "You're just about ready to take the plug," she said, adding a second finger. "That's it, just stay relaxed and give yourself over to it." With that, she pulled her fingers out and I felt the impersonal tip of the silicone plug at my bottom. "Bear down, push against it. It
's a little wider than my fingers, but that will serve as a reminder throughout the day," she said, beginning to press the plug into me. I tensed as she worked it in, the width of it causing some discomfort, but Tanya was patient, almost fucking my ass with the plug as she worked it in, one hand pressing against my low back, forcing me to keep my hips lifted to her.

  "Widest part is coming," she said, but she didn't have to warn me. I felt it. Holding my breath, I forced myself to push and soon, my muscles were closing around the narrow neck of the plug so that it was finally, securely, inside me.

  "Good," she said. "Stay just like that." I heard her walk out the door and waited, all the while still holding my bottom cheeks apart, fully aware of the sight I would offer should anyone other than Tanya walk into her office.

  It was a few minutes but Tanya soon returned and I heard her lock the door behind her. She approached and just touched the plug as if testing if it were secure. I could have told her that it was.

  "Stretch your arms out to the sides and rise up on tip toe please, legs wider. Good." she said as she took the belt from the table. "Here we go."

  She struck hard, harder than she had started yesterday, but perhaps it was that my bottom was already bruised that the belt felt harder, less forgiving.

  "It's humiliating having to bare your bottom and spread your cheeks for your punishment, isn't it?" she asked as she belted me.

  "Yes, ma'am," I called out as the strikes fell harder.

  "Spanked like a naughty child," she continued, lecturing me as she blistered my ass.

  "Please, ma'am," I begged when she gave me three strokes on my thighs before finally putting the belt down and picking up the paddle. "It's too much. Please no paddle today."

  She paused and I felt her hands on my bottom, likely checking the state of things.

  "Please," I asked again more quietly this time.

  "I may be willing to reduce your paddling," she said, one hand pulling my bottom out, exposing what I knew to be my glistening cunt. Her proposal was that she would take the paddling down to two hard strokes but in exchange, immediately after the paddling, I would bring myself to orgasm right there in her office, bent as I was while she watched. I eyed the paddle and turned to look over my shoulder to meet Tanya’s gaze. Four strokes less. This one additional humiliation I could take, if it meant that, couldn't I? It would only take moments for me to come. I would close my eyes and touch myself, I could do that.