The A Grade Student Takes A Bottom Whipping For The Benefit Of Her Generation

"A hypothetical situation and you can try to guess where"

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I was the local managing director of an international company in one of Southeast Asia’s developing nations. I secured a favourable deal during the COVID-19 crisis for a long-term lease on a residential property. The second-floor apartment had a separate entrance and was well-appointed with two bedrooms plus an en-suite. The deal allowed me to keep the rent for the apartment!

I rented out the apartment to two hostesses from the state airline. My accommodation was downstairs, which included a study with excellent broadband.

The older girl, Heather, who was a Cabin Director, was a natural beauty. I sensed a mutual attraction when she viewed the apartment. Months later, on a Friday evening, I drove to an out-of-town fish restaurant. I went to a shopping mall before the meal, and she too was there, and it had to be by chance.

Heather seemed pleased to see me and accepted my invitation to join me for a meal, during which I found out that her flying job would end in three years when she would suffer institutional ageism. She was approaching the end of an external degree in personnel management and psychology. With four languages, excellent staff ratings, and her degree, she hoped her employers would give her a ground job. It was the perfect opportunity for an unplanned meeting with her!

Heather was all smiles and was leaning towards me, so I asked her back for a drink, and she accepted! I had never shown her the ground floor, and she loved it.

“Are you flying tomorrow?”

“No, I don’t fly until Monday. I must do two days’ work on my degree course, but I will take the evenings off.

We were on the leather couch, drinking excellent white wine, music playing softly, and I put my arm around her shoulder. Heather put her drink down, turned her head towards me, and we kissed.

“Would you like to stay with me tonight?”

“How about for the weekend?”

“Why not!”

Heather collected some clothes, her laptop and essentials from her room.

I adjusted the bedroom lights, and we undressed and showered together.

She had a lovely figure, a shaven pussy and obeyed the airline rules about her weight. Heather was no prude, letting me help wash her parts and her bum!

“Peter, I hoped we could get together. I’ve waited a year, and I have not made my feelings clear to you. Tonight, it all happened by accident.”

“I thought the same and wondered how to approach you. If I made a move, it might offend you, and I would have created an unpleasant situation with you living upstairs.”

“Thank goodness we met at last.”

I smothered her in kisses, starting with her lips, moving to her breasts, then her tummy, and taking my time to get to her pussy.

“Please, please, I haven’t had my clit kissed by a man for years.”

I began with my tongue in her pussy and rolled back the clitoral hood, softly licking it.

“Peter, please, can you find my G-spot?”

It’s so nice to be asked, because it shows that the girl likes a finger in her pussy! She was soaking, and her juices lubricated me as I entered her. I could feel the hard area and tapped it with a slippery finger. Heather arched her back, moaning with pleasure.

“Oh God, thank you so much. I’ve had my second orgasm! I dumped my husband five years ago partly because he wouldn’t do this!”

“Have you been alone since then?”

“Not quite, because I have a lady friend in a similar situation, and we take care of each other when possible.” A common affair in Southeast Asia.

“Please, did you do it upstairs?”

“Yes, during the day, if you and the other girl were out. Peter, I’m ready, but I’m not on the pill and don’t have an implant.”

“Don’t worry, I’ve had the snip (I had), and I will give you more oral first.”

I continued with oral and fingering until I felt her pussy in strong motion, and I slid into her with an iron bar of an erection. After many months without sex, I exploded! Heather was in a frenzy and bit me in the throes of ecstasy!

“Your pussy has a powerful grip, and I wonder how you do it?”

“Granny taught me to use a finger, and try to practice by squeezing it with my vaginal muscles. The method works! I’m so horny and want to make up for lost time. Peter, how about a ‘69’ with me on top, and should I clean up first?”

“Yes, please get on top, and you don’t need to clean up, because I want to taste your juices.”

Heather tasted sweet, had a refreshing lack of inhibitions, was an orgasm junkie and a delightful partner. The minx gave me a lip-sucking, toe-curling blowjob.

I wondered what Granny had got up to back in the day to be able to teach it to Heather?

“Benny didn’t like it, thinking it was dirty! When we divorced, I told my mother my reasons, and she went pink.”

“Mother said, ‘I didn’t bring you up to behave like that!’”

It was more of a shock than a surprise, because Heather looked as if butter would not melt!

We lay there in post-coital bliss, and a little hand held my dick.

“Let’s see if I can raise the dead!”

Heather succeeded.

“Peter, concentrate! There’s more where the last lot came from, I’m sure!

The sensuality of her presence and the smell of sex got me over the hump, and I came again. Not a lot, but a definite orgasm!

“Peter, what are you doing tomorrow?”

“I’m in the office by 10 am to talk about a future project, but I will be back by late afternoon.”

“That’s great. I have the day to work on my degree.”

Within a week, Heather had moved in with me, and a new girl took her place upstairs. In the office, within a few weeks, Lady Friday said, “Mr. Grumpy is on holiday.”

“Yes, and I hope it will be a long holiday.” She gave me a crafty glance!

“I hope she’s nice.”

Life carried on blissfully, with me busy at work, Heather away flying, or working on her degree when not taking care of our horniness, and the months passed.

Heather had been home for two days from a longer absence than normal on flights to and from four cities in South America via southern Europe, and was taking a longer break to recover. The first night, I let her sleep, and in the morning, the sly minx said, “I hope you won’t be late this evening.”

“I will be back on time unless there is an earthquake or similar.”

Heather had prepared a wonderful light supper with smoked salmon and a delicious local soup. She was in her ‘quick-release gear’ of baggy shorts and a tight T-shirt. My virile member stood at attention. She noticed, and her nipples hardened!

I opened a bottle of excellent white wine. A glass or two of it always produced a supercharged Heather! She had prepared the veranda with mosquito coils, and we relaxed outdoors with the cool northeast monsoon blowing.

We didn’t waste time. Within an hour, we were in the bedroom, ready, showered, etc. Red stripes covered her bottom!

“Did the airline do that to you for neglecting duties?”

“No! It was my lady friend, the one I told you about, this morning. We caned each other, which we do two or three times a year.”

“You don’t appear to be distressed!”

“I’m not! The stripes make me so horny! I had it in mind to tell you, but I wanted to do it with evidence. You know that the yellow uncle (the cane) is in common use here in schools and at home?”

“Yes, I was aware.”

“I hardly received a caning at school, but my mother was a fierce disciplinarian and caned me frequently from sixteen until I left home at twenty-four when I married. Benny wouldn’t do it, saying it was abnormal, and I missed it. It was another reason our marriage failed.”

Despite the apparent success of our sex life, sometimes I sensed there was something missing, and this could be it! Heather took the initiative, came to me, and put her arm around my shoulder.

“Peter, it will complete my happiness if you will cane me every so often.”

“If it makes you happy, I will. Is it an element that has been missing in our sex life? It’s not illegal between consenting adults.”

Strictly speaking (no pun intended), oral sex was illegal there!

“Yes, it would complete my happiness. I hoped you would understand when you saw my caned bottom.”

Heather went to the drawer and took out a thin cane.

“Please, give me a few strokes.”

“But you have received a caning already today?”

“Yes, but I’m in the mood for more. I’m close to orgasm thinking about it, please!”

She knelt on the bed, her vulva already crimson.

“Would you like your peanut farm attended to?”

“Please.”

I went down on her, and her vagina was already in spasm, perhaps because of the thought of what was to follow. It must have been a hard caning, because the stripes on her bottom had formed ridges.

“How many strokes, please?”

“Six to start with and do it hard, because that’s what I like,” she said with a determined tone in her voice, and not preceded by ‘please!’

She was kneeling on the bed, head down, bum up, skin tight, so the caning would hurt.

“Are you ready?”

“Yes.”

Heather had requested a hard caning, and I respected it, so without ado,

WHISTLE, CRACK.

“Ouch, ouch, that was lovely, give me more, and quickly!”

WHISTLE, CRACK.

“Well done, and I hope caning me makes you feel horny!”

After the sixth stroke, Heather said, “Please, carry on, faster this time, and keep my orgasm going, you bad boy!”

Stripes covered her enticing rump, and I wondered how much more she could take, but I did as requested.

She collapsed on the bed after the tenth stroke and said, “Screw me while I’m stinging like anything.”

“Doggy or Mish, please?”

“Doggy, this time, so you rub on the cane stripes.”

Her pussy was in wild spasm, and in my state of arousal, I tried unsuccessfully to delay the onset of my orgasm, and I wished thirty years could disappear!

Heather was moaning with pleasure, and we collapsed on the bed. She turned to me, and her eyes were wet with tears of pleasure.

“Darling, I’m sorry. Did I overdo it?”

“No, I’m so happy. I waited until our relationship was secure, then I went for it! Thank you so much for acting with such thought and care. Feel my pussy, it’s still shaking.”

She took my head in her hands and smothered me with kisses.

“I will rest for half an hour, and I will show you something I enjoy when I have a freshly caned bottom!”

We rested while caressing each other. She was fondling my dick, and I was gently stimulating her vulva, which caused her minor convulsions of pleasure every few minutes.

“Please, come with me,” and she headed to the bathroom.

What was this about? I had always respected her privacy in the bathroom, apart from showering with her.

Heather took a pee, not caring that I was there. I made to leave, and she said, “Stay. It’s natural, and I need you to help me.”

She adjusted the vertical spray of the bidet and squatted over it.

“Ouch, ouch, it hurts, but it makes me horny with my weight on the cane marks.”

“Do you need me to take your weight?”

“No, but help me wash my little sister.”

I loved doing that in the shower, because it always led to oral on her, which I enjoyed as much as Heather. She turned off the bidet taps, moved forward on it, and opened her legs. “Eat me, please.”

I got on my knees and went to work. Orgasms shook her body, and she groaned in pleasure. Five minutes of my oral ministrations were enough, and she stood up, drying herself.

“Peter, it didn’t shock you?”

“No, not at all. Did you play earlier in the bedroom?”

“Yes, and I changed and washed the sheets afterwards! I’m serious about receiving a caning two or three times a year. It increases my sensitivity to all stimuli, and I feel so alive. The cane is the same type my parents used at home, is six millimeters thick, and the marks will fade in four to five days. The sting is over already, and it just feels sore. Before I met you, the canings would stiffen my resolve to get on with my life, and with you, I can relax without feeling guilty.”

“We have been together several months, and you never mentioned you liked ‘spanking’?”

“I waited until I was sure that we were in a stable relationship. Once I was certain, I organised a session with my friend, so that I could show you the result, because I thought it was the best way to explain it to you!

“How did you decide about our relationship?”

“Three days ago, on my return from the long flights to and from South America, I called you from Spain just before we left on the last leg. When I came through the door, you were sitting there, bags under your eyes, and I saw the relief on your face. You could not have been sleeping well, and your feelings were obvious! I was exhausted, and after a hug and a kiss, I went to bed and slept for twelve hours. You slept on the couch and didn’t wake me. That did it for me! Peter, I am here for you in every way.”

“Your happiness is my concern! You got me out of my rut and brought light into my life. I’m not romantic, and a few months ago, the office manageress said, ‘Mr. Grumpy is on holiday!’ It must be noticeable! Romanticism is a problem for us engineers.”

Heather burst into tears and cried with her head on my shoulder.

“I don’t deserve you. My pussy jumped on the day we came to look at the room upstairs, and you showed us around. I was sure you were the one, but I kept myself under control, wondering how to reveal my feelings to you. The miracle happened when we met by chance.”

“I thought that my nature prevented me from making a woman happy. You have brought out a better side of me!”

Heather stopped crying.

“I don’t need it often, but when I receive a caning, it rejuvenates and heightens my senses, but I limit the frequency of the experience so as not to weaken its effect on me.”

The airline kept Heather busy, and at work, projects appeared out of nowhere. Sometimes it limited our time together for a few weeks. We took a week of leave and stayed at home, relishing the chance to relax and enjoy the many benefits of living in a vibrant city.

On the second day of our break, Heather looked concerned.

“Peter, you met my eighteen-year-old niece, Janet, when she came round and explained aspects of my new laptop software to me? She’s into that sort of thing.”

“Yes, I remember, a pretty girl!”

“She was at a party raided by the police. Drug-taking had been going on, so they tested everyone. Janet, like most of the party-goers, was negative, but the police put her on their ‘at-risk’ register. It’s not a criminal record, but you are on it for at least six months. In that time, if they don’t encounter you anywhere the police regard as dodgy or suspicious, and if you attend their two lectures about drug abuse and anti-social behaviour, they take you off the list. My aunt is so upset and angry with Janet, who is really an innocent caught up in the craziness.”

“OK, are you helping her?”

“Yes, Auntie is worried that she is so angry and might cane Janet excessively. I offered to do it, and would ask Janet to be more careful in her spare time.”

“I assume Janet has received a caning before?”

“Sure, given her background and at her private school, she won’t be a ‘caning virgin’.”

“Peter, Janet looks up to me as a girl who made something of her life. She called me and asked me to cane her, because she is sick of her mother lecturing her non-stop. She said, ‘When mother sees my sore bum, I can make the ultimate threat, which will be, Mum, get off my back, or I will stop studying’. Janet understands she must fix the relationship with her mother, but misplaced pride and anger are stopping her. I know, because I went to see my aunt, and Janet was there. When we were alone, Janet said she would let me give her twenty-four stingers across her bum to satisfy her mother.”

“What would you like to do?”

“Janet will come here, and I will give her twenty-four hard stingers across her cute ass, but she wants you to witness it.”

“Jesus! Are you serious?”

“Yes!”

Heather was wringing her hands together, and it upset me! It bothered me that if the caning took place in my presence with the girl caned naked, local opinion could construe it as ‘outrage of modesty’.

“If I’m there, and she must wear a pair of panties. She can’t be bare bottom.”

“Peter, that’s a point I hadn’t considered, and you are right.”

“We need to take this calmly. I can see it’s upsetting you! When do you want to do it, please?”

“It’s Tuesday. I must check with Janet, but if it’s convenient for you, we could do it either Friday or Saturday evening?”

“How about Friday?”

“Yes, Janet will do whatever I tell her!”

On Wednesday, the national newspaper published details of outstanding exam results, and Janet had come second overall in the country in her pre-university finals. I showed it to Heather. Why on earth were we caning a girl like her?

“Why haven’t Janet or my aunt called me? It ought to be a matter for celebration! What the hell is going on? I don’t like it, and I must call my aunt immediately!”

The call went on, and I saw a strange expression on Heather’s face.

After the call, she said, “Oh Lord, I can’t believe it!”

“What’s happened?”

“Today, the top-grade students have boycotted the convocation, which is normally a celebration of excellent exam results, applause, speeches, etc. TV cameras were there, but none of the top students showed up.”

“How amusing!”

“Don’t say…

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