Sandy's Spankings

by Tiny Tommy

Copyright© 2018 by Tiny Tommy

Erotica Story: A young secretary is spanked and eventually fucked by her boss. This is mostly a spanking story with a little sex thrown in.

Caution: This Erotica Story contains strong sexual content, including Ma/Fa   Coercion   Reluctant   Heterosexual   Fiction   Workplace   Humiliation   Light Bond   Rough   Spanking   Anal Sex   Exhibitionism   Squirting   Small Breasts   .

Sandy was a newlywed; she and her husband Jeff had married just 7 months earlier. Their marriage had been a dream come true so far. Just after they were engaged, Sandy had found a good paying job as a secretary in a small office. With their combined incomes they were able to buy the house of their dreams. But it took nearly every penny they had. They cut every expense they could to have this house. Cutting coupons, shopping only on double coupon day, packing lunches and eating dinners at home instead of going out. Both knew that in a few years everything would be fine, but for now they had to watch each penny. It was worth it to have their dream.

Anyone who knew Sandy would describe her as “cute”, not gorgeous, not attractive although she was, just “cute”. This was probably because of her petite size and figure. Barely 5 foot tall and 100 pounds she looked several years younger than the 20 she had just turned. She had a firm athletic figure with small tits, and a tight ass.

Sandy was good at her job and she really enjoyed it. She did; however, have one significant shortcoming at work—she was always running late. No matter how early she set her alarm, what time she moved her clocks ahead to, she was always late. And that is what got her into trouble at work. Finally one morning when Sandy was nearly a half hour late, her boss had enough. Dan called Sandy into his office and proceeded to fire her,

“Sandy, I’ve told you a dozen times or more in the last month I need you to be here by 8am. Each time you say you will try harder and it won’t happen again. But I can’t remember the last time you were here on time. I’m afraid I just have to let you go.”

“Please, there must be something. I promise, I’ll never be late again.”

Dan replied, “You have said that before, but it hasn’t helped”

Sandy sobbed, “But I can’t lose this job. We will lose our house, my husband will hate me, and I’ll be so embarrassed...”

The sobbing and the begging of this young woman have a profound affect on Dan. He really feels sorry for her. But he doesn’t know what to do. For several minutes he just listens to her sobbing. Finally he offers, “If you can think of some plan that assures that you are here on time each day, then maybe I can give you another chance.”

Sandy has a hopeful smile through her sobs. “Really, like what kind of plan?”

Dan, “I am out of ideas, you need to come up with one. I will give you until lunchtime to give me a good plan. If this plan doesn’t work, I won’t hesitate again to fire you. And you can’t expect any good references with your tardiness. Noon, my office, with a plan. And it better be a good one.”

Sandy went back to her desk. She was relieved that she still had the job, but she was terrified that she still might lose it. The thought of losing her job, and then her home, and then probably her husband too was just too much. Her dream life was shattering before her eyes. She started writing down ideas:

  • I’ll come in at 7:30 every morning; if I’m late I’ll still be on time for 8:00.

  • I’ll work extra for each minute I’m late, twice as long extra as I am late.

  • You can dock my pay 1% for each minute late that I am.

But she realized that none of these would really work. She would still be late.

She felt so helpless. Like a kid. It was nearly noon, and she didn’t have a single useful idea. Then a strange idea struck her. Her dad used to spank her when she disobeyed, which wasn’t often since she hated and feared those spankings so much. She had been 16 the last time her father had spanked her. She thought she was way too old for a spanking, but her father was strict and old fashioned. “As long as you live under my roof, you will abide by my rules or suffer my choice of punishments,” he had said. And she could still remember that punishment clearly. She had to lower her panties to her knees, lift her skirt up her back and bend over a dining room chair. Her dad used his belt. 20 lashes across her bare bottom and the tops of her thighs. She had welts for 3 days afterwards. After that Sandy didn’t even think about sneaking out on date again. That was it, she feared being spanked enough that she knew she could make it to work on time. She was so excited that she might have a plan for keeping her job, that the embarrassment of explaining it to her boss didn’t even cross her mind until after she started to tell him in his office.

Sandy had burst into Dan’s office at ten minutes till twelve exclaiming, “I have it. I know what will work.”

Dan answered inquisitively, “Yes?”

“Spank me if I’m late” Sandy blurted, before it struck her what an odd thing she had just said.

“Spank you?” Dan responded.

Somewhat sheepishly Sandy added, “Yes. I mean if you don’t mind. I know it sounds weird. But it always worked when my dad. I mean I don’t know anything else that would. I’m sorry that sounded way too strange. I guess I don’t have an idea. I’m sorry. I was desperate for anything that might work. And all I could think of was, ... just forget I said anything please. I’m so embarrassed. I’ll just go pack my things.”

Dan was intrigued. He wasn’t into anything kinky, but the thought of having any excuse to touch that firm young ass was really exciting. He often fantasized about Sandy when he was with his wife. A chance like this might never happen again in his life. He could hardly speak when he suggested quietly, “Do you think it would work?”

Sandy pondered her answer briefly, she was embarrassed, but the thought of a spanking from her boss was less embarrassing than losing everything she had dreamed for. She spoke shyly, “I really think it would.”

“OK”, Dan answered, “I am willing to try it. I want you to write a letter of agreement explaining that you have requested to be spanked in response to your frequent tardiness. The note should say that the idea was entirely your own and that you have agreed to the spankings with no coercion on my part. When you have completed the letter, please return to my office with a signed copy and then you will receive your first spanking, for the minutes your were late today.”

Sandy left and typed the note into her computer. She printed it and left it sitting on her desk. She sensed that signing the note would open a new chapter in her life. Finally Dan came to her desk,

“Is there a problem? I thought you would be bringing a note to my office.”

Sandy picked up the note and followed Dan to his office.

“Bend over and touch your toes.”

He admired the view that her tight khaki slacks provided. He was sure he could see the outlines of her pussy lips clearly through the thin material.

“Your punishment will be one swat for each of the 27 minutes that you were late.”

Dan proceeded to use his bare hand against the thin material stretched across Sandy’s bottom. He let his hand linger along her bottom for a brief moment after each swat. Sandy noticed the brief lingering, but didn’t think too much about, mostly she was relieved that it didn’t hurt as bad as the spankings that her dad gave her. She also noticed that it excited her a little bit. She was appalled that another man touching her could have any affect on her, but quickly dismissed it as just her imagination and guilt over suggesting the spanking. After the 27th slap, Dan told her to return to her desk. He didn’t leave his office the rest of the day.

The next day Sandy was on time. But by Wednesday she was late again, this time only about ten minutes. Dan met her at the door.

“I guess it was too much to hope that a little spanking would help.”

Sandy interrupted, “You called that a spanking, those were barely taps. A real spanking might have done some good.”

As the words left her mouth, she couldn’t believe that she had said it. Neither could Dan.

“Maybe you should explain your idea of a real spanking”.

Sandy hesitated before she answered, but what choices did she have at this point.

“Well first any really spanking has to be on the bare bottom. And swats with the hand aren’t anything. My dad always used a leather belt or a thin switch. Each stroke left a mark.”

Dan could feel his dick swell as she spoke. He wasn’t sure when it had ever felt so full.

“Go into my office and prepare herselfyourself for the spanking; I will wait 5 minutes, but you had better be completely ready.”

When Dan entered the office, Sandy had her jeans off and folded neatly on his desk. Her panties were pulled down around her calves and she was bending over the back of his chair, grabbing hold of the armrests. Dan could hardly believe his eyes. Sandy’s beautiful ass was spread just enough that he could clearly see her pussy, that was barely hidden by her wispy blonde hairs. Spanking her was not the first thing on his mind.

“Help me understand,” he said. “The swats with the hand are the warm-up.”

Sandy whispered, “Yes.”

Dan proceeded to spank her vigorously with his hand, making sure to direct extra attention deep between her thighs. Several times he let his fingertips brush against her cunt. Her entire bottom was quickly aglow. As he stood back to admire his handiwork, it seemed that her vulva were swollen, maybe even damp. But he was sure that he was just projecting his own arousal to her. He was getting a little angry that he couldn’t just fuck her, so he took out his anger with his belt.

“You were 12 minutes late today, I expect you to count off each stroke with the belt.”

Dan took careful aim, crisscrossing the strokes for the greatest pain. After the 12th stroke, Sandy started to get up.

“Not so fast”, said Dan. “You still have 27 real strokes to go from Monday.”

Sandy gasped. These strokes hurt worse than she remembered. What if her husband saw the marks, how would she explain them. Dan tried to aim a few strokes of the belt to land deep between her thighs, one landed perfectly with the end of the belt snapping squarely on Sandy’s cunt. She let out a small scream and stood up.

“Since you didn’t count that one, we will have to do it over”.

When it was done, Sandy had 41 strokes with the belt across her ass and upper thighs. Dan stayed in his office to watch her dress and return gingerly to her desk.

Sandy sat at her desk the rest of the day, but she didn’t get much work done. and it wasn’t because she hurt so badly. Instead she sat at her desk pondering how strangely aroused she was. She kept shifting in her seat trying to put gentle pressure on her clit. She was so horny. It wasn’t that she liked the pain; at least she didn’t think so. It was probably just the unexpected events. The more Sandy thought about it, the less she understood her body’s reaction. She wasn’t really sure why, but she was certain it was the horniest she had ever been.

The next morning Sandy made several fateful decisions. As she was getting dressed, she decided to dress a bit more provocatively that day. She picked an outfit with a short, thin skirt and a tight sweater. Then a push-up bra to set the sweater off nicely. Even though she had left home with plenty of time to arrive early to work, she chose to drive around the block several time and come in late. She didn’t want anything that hurt nearly as bad as yesterday, her bottom was too sore to wish for that even if she did want it. But she needed to know if it would have the same affect on her again. She came in 8 minutes late.

Dan was waiting for her, and quite happy that she was late again so soon. He had hardly even slept last night, all he could think about was when he might get another chance to spank her. He had even stopped at the home improvement store to buy a thin, flexible dowel just in case he would have the chance to use it. Apparently he would get that chance much sooner than he had allowed himself to hope. If only she had been later, so he could use it longer.

“Into my office.”

Dan spoke with much greater authority this morning. He knew that now he was clearly in charge.

“Get completely undressed.”

She paused slightly at this demand, but she was so caught up in her own excitement that she didn’t resist in the least. She undressed and folded her clothes neatly onto Dan’s desk.

“Stand there for a minute, I need to explain a few changes that are going to take place. There will be a new dress code for work. The most important part of that dress code is that you may no longer wear any panties or bras under your clothing. Pants aren’t acceptable either, you should be wearing a skirt or dress every day. Whatever you choose should be attractive.”

“You have two choices. You can either arrive at work already dressed for the day, or you can arrive sufficiently early to change in my office and still be ready to start on time. If I don’t think what you chose is attractive enough, you will be sent home to change. Of course this would mean that you are late to work, because your start time is based on when you are in acceptable clothing.”

“Finally, starting with this spanking, all future punishments will be videod for my legal protection.”

Dan set up the video camera on a tripod, and then instructed Sandy to bend over the chair. After she was bent over, he demanded that she spread her legs so that he feet were wider than the legs of the chair. With the camera almost directly behind her, Sandy felt totally exposed. Dan took his time. First he said he wanted to “examine the damage from yesterday.”

He looked closely, running his finger along several of the prominent welts, especially those on her upper thigh. He grabbed each of her ass cheeks and spread her apart even wider to complete the examination. Sandy’s swelling and dampness were clear. So was Dan’s throbbing erection. Dan started the eight strokes. Slowly, with a long pause between each one.

When he finished, he told Sandy that she could put the skirt back on, but that none of the other clothes were acceptable so they would just stay in his desk. She spent the rest of the day working in just her skirt. Throughout the day it seemed that Dan had more reasons than usually to come to her desk or call her into his office.

Sandy was shocked at these developments; it made her feel like a whore. She thought about protesting, but she needed the job way too much and, by this point, any fight left in her was already gone. Sandy spent most of the day browsing websites looking for ideas of what men like Dan woud consider “attractive”. The spanking pictures she found online often depicted the females dressed as a schoolage girl wearing outfits like a private school uniform, cheerleader’s uniform, or a girl scout.

She didn’t want her husband to notice what she would be wearing to work. So she decided that, despite the embarrassment of changing her clothes with her boss watching each morning and afternoon, it would be much better than trying to explain her sudden change in clothes style to her husband. The next two days were rather uneventful; she arrived to work early, changed and went about her day. Her boss didn’t have any meetings in the office, so no one could notice her new “styles.” As she was leaving the second day, she noted that she would not be so lucky tomorrow. Dan had several meetings scheduled at the office that day.

Sandy was slow getting ready the next day. With the thought of several people coming to the office, she couldn’t decide what would be the best outfit to wear. She finally decided that the “schoolgirl” look wouldn’t be too awful, but by the time she had decided, she was nearly 10 minutes late. Worse yet, when she arrived at the office, with a change of clothes in her gym bag, Dan’s meeting had already started ... in his office. Two of the company’s sales reps were meeting with Dan. Sandy stood nervously at the door.

The younger sales rep, Joe, was Sandy’s age. He was single and had just graduated from college and had an all-American type look. Sandy always thought he was sort of cute. The older sales rep, Brent, was an athletic black man in his early 40’s. Sandy didn’t know him that well, it wasn’t that she was a racist, but she had never spent much time around blacks growing up.

Dan let her stand at the door for at least a minute or two. Sandy was clearly nervous as she shifted from foot to foot.

Dan invited her into the office and asked, “Is something wrong?”.

Sandy replied, “Nothing, really.”

“Then would you like to tell us why you have been standing at the door Sandy”?

“You know...” she said.

“I’m not sure, please tell us all Sandy.”

Describing the arrangement in front of other people was the worst thing that Sandy had ever experienced in her life. She stammered, in almost a whisper,

“Well, you see, I have this problem. I’m, like, always running a little late. And Dan was getting really upset with this problem; he even said he might fire me if I couldn’t change my ways. So then he, well not really, it was my idea, anyhow, I asked him to spank me whenever I was late to teach me a lesson. And he has been and I’ve been doing better. And he also makes me wear different clothes at the office and well each morning I change clothes in here, but you are all in here. And...”

“Each minute you wait to change, will just add to your punishment, and our sales meeting could go all day,” Dan added.

Sandy reluctantly started to change. She tried to hide herself somewhat from the three men.

“I think that you should step closer and face all of us. I might sign your checks, but you work for all of us.”

Sandy tried her best to maintain her modesty, changing her shirt first, so that it’s length would partially cover her pubic area while she changed into her skirt. She thought that she must know a little how strippers feel, as all three men stared closely at her. Just as she was turning to leave, Dan spoke.

“You still need to be spanked, now that you are finally ready it is 26 minutes late. Since you kept each of us waiting, I think all three of us will spank you. 10 strokes from each of sounds fair, don’t you think?”

“I’m sorry for delaying your meeting. If you think 10 strokes each is a fair punishment, I’ll accept that.”

Sandy didn’t think it was the least bit fair, but she didn’t feel like she was in any position to argue the number of strokes.

“Joe I will let you go first. Select any implement you want from the desk drawer, tell Sandy what position you want her to assume for the spanking and proceed to give her ten strokes.”

Joe carefully picked up each implement before selecting a paddle.

Joe turned to Sandy, “Bend over my knee.”

The punishment hadn’t started yet, but Sandy could feel Joe’s throbbing erection. She decided that it might be fun to see just how aroused she could get him by squirming on his lap during the spanking, With a little luck she could get her pussy right against him. Her plan worked, she barely felt the spanking, she was so intent on the positioning of her squirming. Besides, while Joe was very enthusiastic, but he didn’t spank her particularly hard. After Joe finished, Sandy smiled to herself thinking that his case of blue balls would probably hurt more than her bottom. That thought would soon vanish when Brent took over.

Brent selected a birch switch. He started by having Sandy spread her legs slightly and touch her toes. The thought of punishing and dominating a white woman really excited Brent. Every time a white person had slighted him or overlooked his ability because of his color bubbled to surface. His grandma had given him the switch plenty as a kid; he knew how to use one. Sandy was the recipient of decades worth of being undervalued or even ignored. Her bottom respresented every white person who had ever treated him diffferently just because of the color if his skin. Brent applied the switch with great power and aim. Each stroke crossing slightly over a previous one.

After about 8 or 9 strokes, he said, “I haven’t been counting, have you?”

Sandy replied that no she hadn’t been.

“OK then I guess we can start counting now.”

Sandy protested. “that isn’t fair”

“Stand up and remove your shirt”

Sandy was now completely naked in front of her boss and co-workers. Showing her tiny breasts was actually more humilitating than having the men stare at her pussy. Sandy recalled having to change in gym class during high school. Every single girl had much larger breasts than she did. Despite being 15, she still wore a training bra. The popular girls teased her about her tiny titties. She could still hear their taunts: “Are you even a girl?”; “I had bigger tits in 6th grade.”; “Do you think any guy would want to be with a ‘no-tit’ girl?”

Before Brent could start over with the switch, Dan stepped in and took charge.

“Kneel on the desk”

Sandy climbed on to his desk, knelt with her legs parted slightly, and leaned forward until her head rested on the desk.

“Instead of starting over, I think we should be able to count the lines made by the switch. We should all look closely so we can agree on the accurate count.”

Neither salesman heistated to join their boss in admiring Sandy’s firm ass and tight pussy. The men moved in for such close looks that Sandy swore she could feel their breath on her cunt. There were nine distinct red lines on Sandy’s butt.

Dan went first, “I count six clear stripes.”

Joe spoke next, “At least one and maybe two of the stripes you are counting look to me like they were left by the edge of the belt. I can only confirm four clear stripes.”

Brent smiled widely, “I have to agree with Joe. I only see four marks that were definitely made with the switch.”

Joe and Brent both turned to their boss, waiting to see his reaction.

“If four is the most the we can say with complete confidence, then Brent should start with number five. Sandy also deserve some extra punishment for failing to count, so Brent should give her two extra.”

This would mean a total of eight more strokes with the switch. Not quite the reprieve Sandy had hoped for when her boss first intervened.

Brent resumed his well-placed, hard strokes with the switch. Sandy had stayed quiet for all of her punishment, but now she began sobbing. The punishment seemed to last forever ... Brent had a sly grin as he admired his handiwork, he might never have a chance like this again.

Sandy was relieved when Dan took over with the strap. That relief didn’t last when he started using the strap on her upper thighs.

Sandy hurt too much to care when her body started betraying her. The spanking and the humiliation were turning her on and it was starting to show in her moist, swollen lips. Oh how she hoped the men didn’t notice. But Dan called everyone’s attention to it, even bringing the video camera and light for a close-up.

When the spankings were finished, Sandy quickly dressed and returned to her desk. She thought all afternoon about how she could just quit. But she also wondered how she could explain quiting to her husband when they needed the money so badly. It was her fault that she was in this situation. She was the one who couldn’t make it work on time. Worse yet, she was the one who suggested the spankings. The spankings hurt and it was humiliating that other men saw her naked body, and that she had to wear the outfits that she did at work. But she had never been so turned on in her life.

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