1969 April: Nicoletta

An Unexpected Chastisement

Written October 2025

The world seemed to be dominated by anti-Vietnam war protests. It was Saturday evening, and I needed a change from all the doom and gloom on the television. So, Luca’s call was welcome. He was the owner of Dario’s Italian restaurant in town. He had a problem with money disappearing from the till, but it still balanced every night. He suspected Nicoletta, or Nico as everyone knew her. She was his charming receptionist and house manageress, in charge of a dozen or so of scantily clad waitresses. He offered me a free dinner if I sat near the till to work out what was going on.

Now I liked Dario’s; it oozed naughtiness. The ground floor was dining booths in a circle around quite a sizable dining floor. The first floor was for private parties, and the second floor had private two-person dining rooms, all with a very large sofa in them. It was a favourite place for wealthy men to entertain their mistresses, and the constant presence of judges, senior policemen and the like ensured it was well protected from the anti-sex brigade. One thing, however, was absolutely essential: no unwelcome publicity. I wondered if my skill at chastising nubile young ladies rear ends, might be connected to Luca’s curious invitation.

I was a regular at the restaurant and Nicoletta met me as usual, dressed demurely but sensuously as usual. She wore full length black dress, which nearly swept the floor, and had a substantial slit up one side, so as she walked a long sexy leg kept appearing. Thin straps over her bare shoulders held up the dress just above her breasts. But it was a thin material clinging tightly to her figure. She clearly was not wearing a bra, and the material neatly outlined her undulating buttocks, as she led me to my booth. It was just opposite the till, and she happily indicated my table, presumably allocated by Luca.

She asked me if wanted a personal waitress, who would both serve my meal and sit with me. I said that I did not, unless she would like to join me. She gave me an Italian Chin Flick (Non Mi Interessa), the traditional Italian gesture of contempt. [Flicking the back of one’s fingers forward under one’s chin.] But she did it rather clumsily, reinforcing my feeling that she was not really Italian. From somewhere, she had a slight Northern lilt, and she never spoke much Italian to Luca, who always spoke to her in English.

So it was that I spent most of the evening sitting in that booth. I resisted the temptation of dance with some of the lovely waitresses. Instead, I watched the till like a hawk. But it was my ears, not my eyes, that solved the case. The mechanical till sounded different when Nico used it to anyone else. When Luca came over to ask about progress, I asked him to demonstrate the till to me. I listened to a normal transaction, then I asked him to enter one then cancel it. The sound was so familiar. She was cancelling transactions, to keep the till balanced. But it was not clear to me where the cash was going. “Luca, can you cover for Nico for the rest of the evening. I need to talk to her.”
  He shrugged his shoulders, “Sure.”
  “And is there a private room I can take her too?”
  He gave a lewd grin. “She won’t go with you.”
  “Oh, I think she will, if she wants to keep her job.”
  “Only room four is use. Take any of the others.”
  “Do you want to send her over?” He nodded and left.

Ten minutes later, Nicoletta came over. “Take a seat,” I ordered pointing to the chair opposite.
  “You know I don’t sit with clients.”
  “Sit, if you want to keep your job. We can talk about how the till works.” She looked shocked. “Luca says that you can join me.” As she sat down, I studied her. The black hair tied back hard into a long pony-tail gave her an austere look. The heart-shaped elfin face and the large silver loops of her ear rings all added to the effect. The black eyebrows and dark brown eyes contributed more. “I know how you are fiddling the till. Luca is not happy. Play your cards right and you probably will keep your job. Make a scene, and you can leave the premises now, and don’t come back. We’ll post your ‘cards, [National Insurance Cards] onto you.”

  Her jaw dropped and she took a few seconds to digest my words. I could see tears well in her eyes; I did not want a scene to deal with. “Are you listening to me?” She nodded. “We are going up to room four where I am going to strip search you. When we find the money you took this evening, I am going to smack your bottom so hard you won’t sit down again this evening.” Her jaw dropped again. “Now lead the way.”

I must say that I enjoyed the view as I followed the full, shapely, pear shape bottom rolling up and down in front of me as she went up the steps. In the room, I told her firmly, “Where is the money or do I have to strip search you.” With a resigned look, she put her fingers in a very discrete pocket in the waist of her dress and produced some £42 pounds [Over £700 in 2025 money], well over a week’s wages for her. I took the money and put it on the table. Next I turned around a dining chair to face Nico.

 I took her arm and pulled her to the chair. With sharp tug, she flopped across my knees, with little resistance from her but a sharp yelp. Her stomach landed on my lap, while her skirt parted along the slit but the toes of her shoes still touched the floor. An exquisite pair of legs appeared. I grabbed the skirt at the top of the slit and pulled it upwards sharply. The rest of her legs appeared followed by an even more exquisite bottom. She never showed a VPL (visible panty line) because she wore no panties. My left hand pressed on her shoulders to keep her in position, which had the effect of raising her feet off the floor. My right hand caressed the firm round bottom for a second before I raised it high and brought it down hard on her right bottom cheek. There was a sharp intake of breath as a red imprint of my hand appeared on the creamy white flesh, and her legs started to kick up and down. A second smack placed a similar imprint on the other cheek. Her hands pushed on the floor as she screamed, “Let me up.” I held her firmly in place.

“No luck, girl, this is too much fun,” I retorted as I applied smack after smack to that firm, trim, more generous than I had expected bottom. In no time, her whole rump had gone pink, then a deep red. Slowly, the pleading and the pounding eased off, and her bottom started to writhe in tune to my smacks. My hand started to sting badly at the same time as I realised that she was becoming seriously around. Gritting my teeth, I smacked her bottom hard and faster, until her body tensed, her legs stopped kicking and straightened out, raising her feet parallel to the ground. Then without notice, her whole body started to shake, and she threw her head back. That was when I saw her eyes roll upwards, making them nearly completely white.

So much for punishment! The girl loved it. I caressed her hot bottom and slid my fingers between her legs. Just a little rubbing of the clitoris set her off again. When her body relaxed, I said, “you can get up now.”

“No way,” she snarled at me. “Do it again. I need it.” My hand having partly recovered, I started spanking that lovely bottom as hard as my hand would allow. When it needed a rest, it slipped between her legs, my thumb deep inside her, on her G-spot, my index finger on her clitoris, causing her to explode in pleasure. Over five times, I spanked, fingered and orgasmed her before she pleaded with me to stop.

  “I’m getting sore. Just screw the hell out of me,” she snarled at me in desperation.

We both stripped and headed for the couch, where I plunged inside her. All good things must come to an end, but the result was certainly not the punishment that she deserved. As we dressed, I told her that I wanted her to come to my house next day after lunch. “I understand that tomorrow is your day off. Your bottom deserved a good thrashing with my cane.”
 “Can’t I come the morning?” she asked cheekily.
 “No, I’m duty master at lunch in hall tomorrow.”
 “What does that entail,” she asked rather contemptuously, as if it was not important.”
  “After chapel, all they boys that have not gone out with their parents, go into the big hall for lunch. The headmaster normally presides, but for Sunday lunch he dumps the duty on a junior housemaster like me.”
  “And what is this onerous duty?”
  “I stand at the empty high table and bang the gavel. All the boys go silent and stand up. I say grace in Latin. Then all the boys sit down again, and I return to the top of the table where the boys in my House sit.”

She grunted; we finished dressing and returned downstairs. Dinner had ended and the harsh main lights were on. The waitresses were cleaning tables and setting up for Sunday lunch. A few eyebrows were raised, clearly wondering what we had been up to. “Luca, can we talk, please?” The three of us huddled together in a booth. “Nico has something for you.” She handed Luca the £42 and his mouth dropped. Before he could say anything, I interjected, “Nico is coming to my study after lunch, and she will be punished like a naughty schoolgirl. Also, she has promised not to do anything like this again if she can keep her job.” I turned to Nico. “Go home and I’ll see you tomorrow.”

Luca was somewhat shell shocked at the developments, thanked me my helped, asked me if I had enjoyed my dinner and wished me Good Night. I failed to tell him what really had happened in that room on the second floor.

Chapel and lunch followed the pattern that I had outlined to Nico, with one exception. Two fifth formers started a heated argument, and one wound up with a plate full of apple crumble and custard on his lap. Before I could go home and meet Nico, I had the onerous job of giving both boys six of the best. Given my irritation at being delayed for my appointment with Nico, I laid on the cuts; both boys left the room with flushed faces, disheveled hair and holding their throbbing bottoms. I only arrived back at my house with ten minutes to spare. I had just changed out of my suit into a relaxing jersey and trousers, when I heard the taxi on the gravel and the front-door bell ring. I opened the door, to an elegant apparition. She stood there in a smart long blue coat, which covered her from neck to ankle. “Can you pay the taxi please? I’m out of cash,” she declared emphatically, having dropped any attempt at speaking with an Italian accent.

In the sitting room, she shed her coat to reveal a black figure-hugging micro skirt and a tight pink blouse tied across her front, clearly showing the bare skin across her tummy. “Cinzano Bianco, tonic and ice, please. Where’s the bedroom?”
  “What’s the hurry?”
  “What’s the hurry? After what you did to me yesterday, I’ve already had to go to the bedroom and jerk myself off twice today. Least you can do is give me a good poking, then you can whip my bottom as much as you want. Where is it?”
 “Upstairs, turn right.” I made her drink and a whisky dry for me. When I arrived in the bedroom, she was naked on the bed, her legs wide open displaying all her most intimate parts. It didn’t take me long to strip and plunge into her deepest recess. I was fascinated by her orgasms; her eyes rolled up and partly sides ways at each orgasm, making her look momentarily cross eyed. Her legs shook violently on each side of me and her nails dug painfully into my back. By the second dispatch of fluid into that innermost recess, I had pinned her wrists above her head; that seemed to excite her even more. Once sated, we sat up and enjoyed her drinks.

  She looked at me with sheer lust. “You don’t happen to need a wife, do you?”
  “I do but I run a bachelor house and would have to resign if I married. I want to marry as soon as I get a headmastership.”

  “Pity, you could smack my bottom everyday if we were married. I never knew sex could be so good. Where are you going to beat me?”
  “Here, across the end of my bed.” She glanced down.
  “How many strokes?”
  “At least 10.”
  “On the bare?”
  “Of course.”
  “What if I cry?”
  “Too bad.”
  “I think you are a beast, but I love you, even if you won’t make an honest woman of me.”
  “Have you had the cane before?”
  “About fifteen years ago, I was sent home from school for stealing. My father gave me six of the best. The other kids thought it was funny when I couldn’t sit comfortably next day.”
  “Times don’t change much. How much have you cheated Luca out of?”
  “Not sure, must be at least £500,” [Over £8,000 at 2025 prices] she cheerfully admitted.
  “Why do you need so much money?”
  “Not sure that I should tell you.”
  “Then you better bend over the end of the bed and I’ll beat it out of you.” I suspected that that would not work. A striped bottom might make her even more aroused; I was not sure if I could keep up with her.

Moments later, the slim beauty was bent over, kneeling on the large linen box at the end of my bed, her arms outstretched along the brass top bar of the footboard nearly touching the brass ball finials at each corner, her head resting sideways on the blankets. The position converted the neat pear-shaped buttocks into neat globes. The red from the spanking the previous night had gone, and her rump was now creamy white. It was also a conundrum! Last night was meant to be a serious punishment. Instead, it had turned out to be a major reward.

This was always the problem with chastising a female bottom as a punishment. The Kinsey Report [Alfred Kinsey: Sexual Behaviour in the Human Female (1953). A report, based on 18,500 personal interviews, which indicated a wide variation in behaviour and sexual orientation] estimated that 10% of women found having their bottom thrashed a major turn on. My feeling was that it was substantially more. Many women tolerated the two minutes of pain because of the exquisite nature of the before and after. Certainly, many women that I encountered viewed it as a seduction technique. They prompted me to cane them, showing all their most intimate parts. Afterwards, they then cuddled up to me for succor and expected to be taken to bed as part of the recovery process. From meeting to bed in an hour! A process that might take months by ordinary seduction techniques.

So, if Nico found this caning a turn-on, I am not sure what would be achieved other than our mutual sexual satisfaction. I raised the cane and brought it down hard on that shapely rump. She yelped and her hands shot to her bottom. At first, she gripped her bottom hard, then turned them, palms out, to protect them. I was in no hurry and some twenty seconds later, I admonished her, “Take those hands away. You have another nine to come. That’s what thieves get.”
  “Oh, no Sir. Please, I can’t take it.”
  “Remove those hands, or we start again.” Reluctantly, they returned to the bar, revealing the angry red tramline across the crest of her bottom. She was sniffling as I raised the cane to place another red line, virtually parallel to the first. She yelped, then sobbed, as I waited for her bottom to stop dancing. This time she managed to control her hands.

The swishes and the whacks carried on, while yelps and sobs ran in tandem to them. Her head thrust back at many strokes, her long black ponytail swinging back and forth, almost like a whip. I felt that she had well-earned the punishment and there was no reason to ease up. After a few strokes, some of the lines began to cross and the yelps gained more intensity, before they calmed down. Presumably she was adjusting to the pain. Slowly the lines built up until they formed a broad red band across her bottom. But the continuing sobs indicated that, at least, a partial lesson was being taught.

After the tenth stroke, I waited for her dancing bottom to still, then told her to stand up. She did as she was told, and suddenly threw her arms around me, almost squeezing the breath out of me. She sobbed uncontrollably for a minute or two on my chest, making it soaking wet. I was glad that I was not wearing a shirt. Next, somehow, we were kissing passionately. Finally, her blood shot eyes looked up at me, “Get me another drink, a very large one, then you can screw me again.”

The drink almost went down in one, then she threw herself back onto the bed and opened her legs wide. Each time I thrust, she thrust back hard. The sore bottom on the bed making her hips push back hard. By six o’clock, we were sated again. Without warning, she jumped out of bed while I dozed. She returned with the rest of the bottle of Cinzano and a large lump of cheese.

After she had consumed both, her mouth moved onto my member, but the alcohol was beginning to control her. Delighted by the positive response, she lowered herself onto me and started to work with her hips. I fondled those firm breasts until I could see her eyes begin to roll up as her body started to orgasm violently. As it subsided, she flopped onto my chest, her head turned to the door, resting on my chest.

I held her shapely body and silken skin, firmly in place and asked her, “So do we do all this again next weekend.” Her head turned and her chin now rested on the chest. Her slightly glazed eyes looked into mine.

  “No can do. Sorry, my boyfriend gets out of prison on Thursday…… Oh, shit. I shouldn’t have said.”
  “That was the alcohol speaking. Anyway, what’s that all about,” I asked and slapped her hard on the bottom.
  She gave another yelp, “Luca doesn’t know about him. Please don’t tell him.”
  “Is that what the money is all about? How long has he been in jail?”
  “Nearly eighteen months, he got two years but he’s out early for good behaviour.”

  “So why the money?”
  “We tried for a baby before he went down. The doctor said he was firing blanks. When you and Luca caught me, I decided if you got me pregnant just before he got out, I could say it was his. I was thinking of screwing someone before yesterday and then you came along. I thought, who better than some posho like you to do the job, and I’m glad I did,” she said with a contented, inebriated, smile.

Somehow, the fun of the weekend had just evaporated. We had a couple of steaks in a somewhat tense atmosphere. Finally, she gave me a rather limp kiss. A couple of months later, Luca rang me to say that she had resigned to have a baby, and that she and her “husband” were overjoyed. I never saw her again.