I had been the Operations Manager of a major contracting company in South East Asia’s head office for several years and was single in my late thirties. I spent time in the local head office and travelling around most remote site areas. The term ‘Operations Manager’ meant that if a difficult or potentially dangerous operation would take place with a high level of attention to HSE required, I would be there on an extended visit to make sure the crew operated using safe procedures, etc., and this kept me very busy. I had to ‘do everything,’ if required.
My assistant was a local married lady, who was also head of light electronic engineering and IT. She was in her early forties. Her nickname at work was ‘The Iron Butterfly,’ and I hoped it was unknown to her. Judith was a hard case, ran everyone around and put up with zero nonsense. I liked her as a person and admired her approach. A proportion of the local male workforce found her hard to deal with, because in their culture, the female should be subservient to the male, and here it was the other way around. Their complaints fell on deaf ears! The company got a big bun for their penny in Judith.
Her husband, who was a senior manager in another important local company, died in a road traffic accident in a remote area. I went to the funeral, the rites of which went on for a week.
Judith was very attractive, and I had never put a foot wrong at work. I wondered if she realised she had an admirer in me. Being female, she probably did, but had made no show of it. If it wasn't raining, I would cycle to work. If it was wet monsoon weather, I would drive.
It was a few days after her husband’s funeral rites. At six pm, I was on my way to the bike shed, and Judith was in the lift with me. On the way to the car park, before we reached the bike shed, we were alone, and she said, “Give it three months, please,” and smiled. She had guessed!
I gave it three months and a bit, and after an evening meal with a client, we went for a drink at an upmarket outdoor bar by the river.
“How are you getting along in Martin’s absence?” I asked.
“My only problem is that the girls are getting more difficult to deal with in his absence, not that he did much to help me with them or in the last few years, with anything much other than to pay bills. He spent too much time with his pals and expensive companions at the KTV (‘hostess’) bars. It didn’t matter financially because the company paid me well. The house was paid for by his insurance, and I have his widow’s pension, so I’m better off than I have ever been, but the problems with the girls are getting worse.”
There was no sign that she missed Martin. It was the reverse! I knew the girls enough to talk to them since there was a level of social activity at the company and there had been parties at his house around Christmas, local cultural events, work celebrations, etc.
Time to act! “Judith, you know I’m single and we have known each other at work for several years now. Would you like us to spend more time together?”
She put out a thin hand on the table, and I took it. I had my answer.
“Neil, I hoped we could spend time together.”
“Who looks after the girls when you are at work or out at a function such as tonight’s meal, please?”
“I’ve got a Thai housekeeper lady whom we have employed for years. Her husband has a long-term work permit here in the government landscaping department. They live in our annex flat.”
“It’s the little one, Mary, and to a lesser extent the middle one, Liz, who gives problems. Mary is nearly seventeen and is not working hard enough at school. Liz is almost eighteen, and I am worried she is keeping poor company. Lucy is twenty and is at uni. They work her so hard she hardly has time to breathe. She is no problem, poor girl, she is so overworked. One thing their father did, for all his faults, was to maintain discipline if they gave trouble.”
“How did he do that?” I asked, half expecting the answer.
“He caned them and did it hard if necessary and they accepted it. It’s that way in our culture. The little one from the age of sixteen has got a sore bottom and the middle one too, but Lucy hasn’t received the cane for about three years. Of course, the canings have stopped now. They won’t accept them from me. Lucy is perceptive and, she said to me, ‘Why don’t you get friendly with Neil at work now Dad’s gone? He’s a nice guy and the little ones like him. He could deal with them.’”
To say this gave me a surprise is an understatement! Rather brazenly, I said, “Would you like to come back to my apartment for a nightcap?”
With a beautiful smile, Judith said, “Why not?”
We found ourselves in my apartment and with a Cointreau inside her, Judith got out of her clothes in the bedroom in record time. She took a shower in the en-suite and I did likewise. She lay on her back, legs apart. I bent over her to kiss her when she grabbed me by the hair and pushed my head towards her mound. It was clear what she wanted, and I nibbled her clitoris and tongued her vagina.
Judith had a tremendous orgasm within seconds and grabbed at my penis.
“Don’t worry, I had a hysterectomy three years ago. You were away on an extended visit to that big drilling operation. We had to get Alan to stand in for me. Do you remember?”
Of course, I did, but had been so busy that apart from sending flowers to the hospital and because Judith was back at work by the time I returned, I never gave it a second thought.
Judith was a wonderful performer, with a tight vagina, cute breasts still in good shape, and very enthusiastic. She clung to me, moaning in pleasure with her pussy in spasm!
“You are big! Please be careful, don’t go in too deep because it hurts! My vagina is just a little shorter than it was before my hysterectomy. I didn’t get enough of this with Martin. He wouldn’t spank me, either!”
“Spanking! Do you like spanking?”
“In my community, there was, and sometimes still is, strict discipline. It was even stricter for the girls and I got caned by my father until twenty-two, when I got married. As I got older, it was a tremendous turn-on. I always remember sneaking off to see Martin for sex before we got married, and he saw the marks on my bum. I’ve never understood why he didn’t know we got spanked, but it was an enormous turn-on for him. Martin would never do it to me, before or after marriage. He had a mental block about it, and I could never work out why. But he would give discipline canings to the girls. I always thought he was looking for a mother figure, which wasn’t me.”
“Neil, please, will you spank me soon? I’m desperate for a spanking!”
I knew about spanking as a sexual kink but had no experience of it. I am from the UK and I knew about the history of caning, and how it stopped before I was at school. It had largely gone out of fashion with parents because of legal ramifications. These did not apply to where I was living and working.
“Isn’t it more important for you to inform, as delicately as you can, your children about our relationship first? It’s up to you, but I don’t think I will be of much help to you if I can’t openly relate to your children.”
“I will talk to them. I know Lucy is in favour. The other two will probably decide on you regarding how you treat them and their perception of how you treat me.”
“Let me know how it goes. I have leave to take and they are pressuring me to take it because I’ve had almost no leave for two years. We could have a family holiday or at least you, me and the two younger ones, in the place nearby where we can stay in an apartment hotel and hire a boat, go kayaking, go on mountain hikes and plenty of other things. That might appeal to them. I can pay for it. What do you think?”
“Their father did little with them in the way of holidays during the last three or four years. He was too interested in KTV, etc. I will talk to them. I’ve got canes at home. Please, can I bring maybe two or three of them here and you give me a sore bottom? I haven’t had one for years, and I will find it so arousing.”
“Judith, are you certain about this? You must make sure I ‘do it right,’ because it will be the first time I have given a caning.”
“Don’t worry. I can show you how to do it. Perhaps you should receive a caning from me first. It will be the best possible way to instruct you!”
“I can’t refuse if I’m going to do it to you. When do you think we can find the time?”
“Tomorrow is Friday. If we do it tomorrow, I don’t have to sit at the office for two days and the worst of the sore bottom feeling will be over by Monday. If I talk to the girls before I come here, I can see how they react to my news of our friendship and talk about the holiday plan with them.”
“Great, let’s hope for the best!”
“I must be going. It’s late. See you in the office tomorrow.”
We had a lingering cuddle and kiss, and Judith went home. We kept a safe distance at the office the next day. Judith arrived at my apartment at eight-fifty, carrying what looked like a sports bag.
“I need a large gin, please,” as she sat in one of my leather recliners.
“How did it go?” I asked.
“Better than I had dared to hope. The girls are enthusiastic about our friendship and the suggestion of the action holiday has gone down too well. We must plan for it as soon as possible. They are on the school break in eight weeks, which gives us time to plan it. I will be ready for action after I finish my gin.”
I had showered already and had a bathrobe and towels ready for her. With the gin finished, Judith stripped off in the bedroom and took a shower.
“Get undressed and help me,” she ordered.
I took my clothes off in record time and we were in the shower together.
“You know where to wash me.”
I helped her wash her pussy when she said, “How about my ass, too?”
I would not have touched her ass without the invitation. Call me old-fashioned.
Judith took hold of my penis, rolled back the foreskin and washed the bell end.
Once dried, Judith sat on a towel on the bed, legs wide apart. Without a word, I went down on her. The dark pink clitoris was larger than I had imagined it would be on quite a small lady. Her labia were crimson in a state of high arousal.
“Once I’ve had enough of orgasms, I’m going to cane your bottom hard,” she warned me!
“When did you last receive a caning?” I asked.
“When I was twenty-two. Martin refused, and I did not dare to look elsewhere. My orgasms after my father’s hard canings were the best I have ever had and I’m hoping for better from you. I asked my father to cane me after I had married, but he refused and said it was up to my husband now. I can’t wait.”
“Kneel on the corner of the bed on a towel, bottom and head down. I’ve brought a thin cane and a medium cane, which is what I expect you can handle and will make a great impression on you. I’m going to give you ‘six of the best’ and we see where we go from there.”
Judith went on about where to stand, how to allow for the swing of the cane, making it move outwards, avoiding ‘sensitive places,’ where to aim, not too high, not too low, etc.
“How did you get so expert?” I asked.
“I was the oldest of four sisters. My Dad was often away at sea and he put me in charge of their discipline and not their mother. He thought it was better for them to have their mother to run to if upset, and let me discipline them with mother’s knowledge and approval. I gave at least one caning a month for three of four years, starting with my oldest sister when she turned sixteen, and then carrying on with the others when they turned sixteen. By the time I got married, sometimes I gave one caning a week, and I enjoyed it so much. It kept them in order.”
No wonder they called her ‘The Iron Butterfly.’ The persona stuck.
“Are you ready?”
“Yes.”
A whistle, a ‘crack’, and a line of fire blazed across my bottom. It would be painful, I knew, but this was worse than I had imagined. With a gasp, I kept myself together and said, “One, thank you.”
Whistle, ‘crack’, and stroke number two crashed into me. “Two, thank you.”
It was surprising how the pain in my bottom drove all other thoughts away. To my surprise, I felt my penis stirring. It could have been the sight of the beautiful Judith standing over me with the cane. The caning carried on like this until I had received my six strokes.
“Brave boy, you took it so well.”
Her cool fingers were massaging the marks. I looked around, and I saw her other hand on her mound, with a finger stretched out on her clitoris. The brave thing to do, I guessed, would be to ask her to give me a few more cane strokes, to see if this would give her an orgasm.
“Judith, if it will help, please, give me a few more cane strokes. I think it’s turning you on!”
She stopped massaging me and I felt the cane resting on my bottom.
“If I give it hard and fast, I will come sooner than if I do it slowly. Do you think you can handle it?”
“Why not try? I’m not a baby.”
Whistle ‘crack,’ Whistle ‘crack,’ Whistle ‘crack,’ Whistle ‘crack.’
The canings stopped, to my enormous relief, and I heard Judith moaning. She collapsed onto the bed, fingering herself.
I felt my burning bottom and could feel the hard, hot ridges. No wonder the cane is such an effective discipline instrument!
Judith was lying on the bed, legs apart.
“Sex or a spanking? I asked.
“I would love sex and I deserve a caning, so let’s do the caning first. Do you think you are ready, please?”
“Yes, after what you did to me, I’m sure I can handle it.”
She got up on her knees, bottom up, head down, in the same position as I had used.
“How many strokes would you like, please?”
“Give me six strokes to start with and we see how it goes. Please do them hard, because I deserve it and my father never spared me. If I got a caning, the marks would last for at least two weeks, and that’s what I would like from you.”
“As you wish. You must know it’s going to hurt?”
“Of course, I expect it and I need it.”
“Ready?”
Judith nodded. I tapped her bottom with the cane, lifted it back, and swung it forward. It landed with a loud crack and bit into the flesh of her buttocks, and she gasped.
“How was that, please?”
“Wonderful. Twenty-one years have disappeared. I can remember feeling like this when my dad thrashed me.”
“Ready?”
She nodded again, and I gave her stroke number two with similar force. Two deep red lines appeared on her bottom with the tram line marks on each side. The cane had not cut her skin. I had carried on caning her steadily until I had given her the sixth stroke. Judith gave little yelps after each stroke and I gave her number six with increased force and, for the first time, she yelled out loud. After the strokes ceased, she dropped onto the bed, rubbing frantically at her well-thrashed rump.
“That’s the hardest caning I have ever had. Neil, please, go down on me again, and then when I’m ready, you can screw me.”
I gave Judith another tonguing and fingering and eased myself into her quivering vagina. She took my head in her hands, kissed me, and clung onto me with her legs crossed behind my back. She was groaning in the throes of pain and pleasure. My caning had helped me achieve one of the strongest erections I had ever known, and even after I had come, I remained hard within her. This was a whole new experience.
We were still making ‘the beast with two backs,’ and Judith wanted to talk. She told me how keen Mary and Liz were on the idea of the ‘activity holiday.’ The uni breaks, unusually, differed from the school breaks and Lucy was working out if she could come with us. We knew the school break dates, and she asked if I could take those two weeks of leave. I was under pressure to take my leave, and I had time to sort out the cover at work.
The conversation got round to the discipline thing. Judith thought it best if we moved slowly on that one, and let Mary and Liz get to know and accept me. The holiday should help with that. It was up to her.
At work, I organised time off. A travel agent handled the entire holiday booking, the flights, the apartment hotel, the catamaran yacht, the kayaking, the mountain hike, the fire balloon festival,...
