Richard s Little Problem
- 3 years ago
- 51
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Margaret arrived to do the cleaning on Friday and she knew that she would be returning to the house again that evening to spend another night with Richard. She had still not made up her mind whether the caning that Richard desired would be administered on this day or whether she would postpone it until another time.
Richard was determined to keep the caning at the forefront of Margaret's mind and she smiled to herself when she found a magazine opened on a page showing a young man bent over and an older, headmistress type, woman behind him flexing a cane.
Margaret had given her late husband, Ralph, some real thrashings with a cane over the years, sometimes with him bent over and sometimes with him lying face down on the bed with his bare arse raised by pillows under his midriff. She had, however, not put the cane to use for at least four years.
The photograph in the magazine and her own reminiscing finally made up her mind that she would bring the cane with her on her return later that day but she also thought that, from her point of view at least, there was no reason why she should not stay Saturday night as well as Friday. She left a note for Richard confirming that she would bring her cane but she thought that it would be a good idea for the beating to take place on Saturday evening and she would return home on Sunday.
On finding the note on his arrival home from work, Richard felt elated at both the prospect of the caning and the suggestion that he have two nights with his much older lover. When Margaret arrived, Richard instinctively looked to see if she had the cane in her hand but she told him that it was in her car and that she would bring it in in due course.
There was the usual 'on arrival' kissing and then the two of them settled down on the settee together and put something on television although neither of them was really watching it as they frequently exchanged kisses. Margaret was starting to feel particularly randy so she undid Richard's trousers and started squeezing his cock through his underpants.
"Are you feeling horny again Mrs Leech?" he asked as she massaged his cock to erection.
"Seems that way, what are you going to do about it?" she said as she now dragged Richard's underpants clear of his penis so that she now had his bare cock in her hand.
Richard massaged her tits through her blouse as she slowly wanked his cock and then Richard undid her blouse and pulled her bra down at the front exposing her large breasts. Margaret moved so that she pressed her naked tits into Richard's face and his hands went to her trouser encased buttocks.
Margaret had her legs on either side of Richard's and as he licked her nipples and caressed her arse she said, "Fuck, Richard, you turn me on."
"And you do me you gorgeous sexy woman," replied her young lover.
Margaret needed his cock in her so she backed off where she was and removed her trousers and knickers and then returned to her original position but now guided his erect penis into her needy vagina. As she lowered herself onto him she groaned with pleasure and as she started to move up and down, he again put his mouth to her breasts and hands to her arse.
Some of Richard's fingers found their way into Margaret's arse crack and he then got the thumb of his right hand positioned in such a way that every time that Margaret slid down his rigid pole his thumb touched her anus. This was an additional sexual thrill and something that she had not had before and she was wild with lust as she rode his cock bringing her to orgasm, "Oh, God, fuck, oh, oh fucking hell," she panted as she came and as her arse descended this time Richard's thumb actually entered her anus.
Richard was both amused and thrilled by the pleasure that Margaret was getting but he now realised that his prick was about to spurt and he groaned, "Oh shit," as his spunk rocketed upwards into Margaret's cunt.
"Phew, that was something wasn't it?" giggled Margaret as they got their breath back.
"Certainly was," agreed Richard with his cock still in her.
When they went to bed a couple of hours later their sex was much more measured after their exertions in the early evening but just as satisfying as Richard shafted his sixty-year-old lover in the missionary position.
During the course of Saturday morning, Margaret fetched her cane from her car and placed it on the coffee table. Despite having wanted to feel one across his backside for quite some time this was the first time that Richard had actually seen a cane and the fact that one was now on display meant that his caning was ever closer.
Margaret had given her late husband some merciless floggings with that cane but she had no idea what Richard would be able to take so she thought that she had better talk to him about it, "My Ralph had a very high pain threshold and I gave him some real thrashings but I do not know what you will be able to take when the time comes," she said.
"I want you to treat me as you did him," said Richard.
"I am not sure that you know what that could mean, for instance after I cane you later you might still be feeling it when you go to work on Monday," she warned.
"Margaret, that is exactly what I long for," he enthused.
She was still not convinced so she gave him a further warning, "You should know that once the caning starts it is me and only me that decides when it is finished."
"Perfect, I want to be at your mercy," he replied although she was still uncertain whether he knew what he was in for.
It got to mid-afternoon and Richard said, "Fancy going to bed for an hour or so?"
"Ha, who is horny now?" she giggled, and then looking over her shoulder as she headed for the stairs she added, "Well, come on then."
Richard was again following those buttocks, that were currently inside knickers and trousers, up the stairs as they headed for what seemed likely to be their last fuck before his caning.
Facing each other in the bedroom clothing was removed and they stood naked kissing and groping until Margaret said, "How about a sixty-nine?"
That was one of Richard's favourite numbers and he responded, "Sure, me on top, or you?"
"Me I think, I fancy lowering my pussy onto your face," replied Margaret.
So Richard lay on his back, cock fully hard, and Margaret teasingly lowered her vagina onto his face before leaning forward and taking his penis in her mouth. There was much sucking and licking and they were both really turned on and neither was sure whether the oral action was going to continue until they climaxed but Margaret made the decision when she took her mouth off Richard's prick and said, "I need this in my cunt."
Richard was still licking the said cunt at the time but Margaret swung herself off his face and was on the bed legs wide apart. Richard, or more specifically his penis, took up the invitation and cock and cunt were reunited. The sixty-nining had taken them most of the way there so it was not too long before first Margaret and then Richard came.
After a little cuddle, they showered and then dressed leaving the application of cane to buttock the next item on the agenda.
They cuddled up on the settee for a while and Richard kept looking at the cane which was still on the coffee table. It was now almost seven o'clock in the evening when Margaret, out of the blue and in a stern voice said, "You will go and wait in the bedroom, I will tell you when I am ready to deal with you."
Richard looked at her with a smile on his face but on seeing that she was very much unsmiling he got off the settee and went upstairs as instructed, he knew that his caning was imminent and he was both nervous and excited.
As Richard had left the magazine open on a page depicting a headmistress, Margaret had decided to make the punishment a school-type one although much more severe than accepted school discipline. Richard was upstairs wondering how long he was to be kept waiting and he had been up there for about twenty minutes when Margaret shouted up the stairs, "Richard Moran, down here, NOW!"
He went downstairs to meet his fate and his cock was fully erect in his underwear and trousers. He went into the living room and there was Margaret dressed as he had never seen her before so you must have had the clothes in her car and changed whilst he was upstairs. She was dressed very schoolmistress like in a white blouse and a black skirt and in her hands, she bent the cane, The expression on her face indicated that she was taking things very seriously.
"Mister Moran, I am told that you have been having sex with a sixty-year-old woman, is that true?" she demanded.
Richard managed a weak, "Yes," in reply but the 'headmistress' promptly corrected him, "You will call me ma'am when you address me."
"Yes ma'am," he responded with his eyes on the cane that she was still bending.
"In that case, I will have to give you a sound thrashing, bend over and grip your ankles," she ordered.
He had expected to be told to lower his trousers but he bent over as instructed and promptly felt Margaret undoing his trousers and dragging them down. She then lowered his underpants but had to pull them out at the front to get them past his erection, she left them between his knees and his arse so now his bare backside was presented.
Margaret slashed the cane through the air a few times and each time his buttocks twitched causing a sadistic smile to cross Margaret's lips.
"You young man will not be sitting down for a very long time when I have finished with you," she advised and the bent-over Richard mumbled, "Yes ma'am...I mean no ma'am."
She had not decided on a number of strokes but intended to deliver a minimum of eighteen as she tapped the cane against his rather sexy bottom.
She raised the cane high and then slashed it down SWISH! THWACK! and then she watched a Richard shook his arse slightly from side to side and a thin red line started to appear.
She landed a second stroke rapidly followed by a third and Richard sort of groaned and whimpered as two further cane marks appeared on his buttocks. Margaret continued the beating at irregular intervals but had now reached double figures with the number of strokes and Richard was now very obviously in some discomfort as he squirmed and sobbed but remained in position.
On and on the thrashing went and she had delivered eighteen strokes but as he seemed to be taking it well, despite now loud sobs, she decided to give him more.
Richard mentally was in turmoil because he was receiving exactly what he had long wished for but his arse was on fire and he did not think that he would ever be able to sit down again. His penis was still rock hard and he was concerned that he might spunk onto the carpet which would infuriate Margaret as the cleaner.
SWISH! THWACK! SWISH THWACK! Two more lashes from the now panting and sweating Margaret but still, she raised the cane high.
She brought the total number of strokes to twenty-four and, with the cane quivering in her hand, she surveyed the red marks all over the man's buttocks.
"Stand up," she said and Richard very slowly and very painfully straightened up. He wanted to put his hands to his flogged cheeks but remembered that Margaret had forbidden him from doing that after his hairbrush spanking so he just moved his fingers by his side.
She now stood in front of him and looked at his very red, tearstained face, and then she looked at his still rigid penis.
"You took your beating well, young man, you may rub your bottom," she said almost sympathetically.
"Thank you, ma'am," Richard breathed as he put his hands to his thrashed arse cheeks.
Margaret herself was red-faced, partly because of her physical efforts and partly because of her sexual arousal which had caused her knickers to become extremely wet. She thought that Richard probably needed some post caning time before being able to indulge in fucking so that could wait until bedtime but she decided that she should do something about his current erection.
"We will fuck later but I will now ease this for you, would you like that?" she asked with her hand on his cock, she was now Margaret rather than the headmistress.
"Oh, yes please," he said and then wondered whether he should have said 'ma'am' but as she did not correct him he assumed that it had not been necessary.
Margaret had her face at his prick and he thought that she was going to give him another blowjob but Margaret had other plans as she wanked him hard and fast with her right hand and very soon his spunk was splattering her face, much to her amusement.
After she had scooped the cream off her face and had licked her fingers she said, "So, you have had a caning, what did you think?"
"It fucking hurt but it was wonderful, thank you," he said,
"The marks will be there long after the stinging has gone so you had not better be showing too many people your bare bum," laughed Margaret.
"The only person I want seeing my bare bum is you," replied Richard who was still trying to alleviate some of the pain from his arse with his hands.
In bed later, Margaret had her knees almost at her tits as Richard gave her a very thorough fucking and he, with the tingling from his buttocks increasing his ardour, made her cum three times before he spurted hard into her.
Richard could not sit down for breakfast and both he and his lover examined his cane marked arse before he had Margaret bending over the kitchen table as he yet again ejaculated into her cum soaked vagina.
It would be a while before Richard could take another severe beating but the two of them fully intended to give each other much more sexual pleasure in the meantime.
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Candy Cane . That's the scent that has been left lingering in my clothes tonight, and the more I smell it, the wetter my panties become. It's the most sensuous thing, the way you blow the smoke from your hookah into my mouth, your lips so close to mine, yet not close enough to touch, or to kiss me passionately the way I’ve secretly wanted you to for all of these years. It's a trick I'm guessing you picked up working nights at the hookah lounge downtown, along with the way you know how to...
First TimeWe will now relate what was passing in the house of the king's attorney after the departure of Madame Danglars and her daughter, and during the time of the conversation between Maximilian and Valentine, which we have just detailed. M. de Villefort entered his father's room, followed by Madame de Villefort. Both of the visitors, after saluting the old man and speaking to Barrois, a faithful servant, who had been twenty-five years in his service, took their places on either side of the...
Richard the Sissy Learns Community Service By Joney Cunnigham It had been awhile since I completed my training from my sister and Gina. Mom and Dad decided to take my sister on vacation, but since I didn't want to go, they decide I was old enough to stay home for a few days by myself. My mom gave me a list of chores to do, so I would be kept busy for the long weekend ahead. Mary just made a devious smile as she said, "You know how you must do you chores," and then yelled, "You...
Two days after, a considerable crowd was assembled, towards ten o'clock in the morning, around the door of M. de Villefort's house, and a long file of mourning-coaches and private carriages extended along the Faubourg Saint-Honore and the Rue de la Pepiniere. Among them was one of a very singular form, which appeared to have come from a distance. It was a kind of covered wagon, painted black, and was one of the first to arrive. Inquiry was made, and it was ascertained that, by a strange...
The night was young. 8 o'clock to be exact. I had just gottin out of the shower. My body was shinning in the light from the wet, warm water as I walked nudely into my bedroom with the windows fully open. As I lay on my bed and stroked my vagina with my pink spiral dildo, there was a knock on the door. It was my electrician telling me that there would be experements done on the neighborhood electricity and i wouldn't have power for at least 12 hours. You must understand that i had not had sex...
InterracialI shall always remember last Friday. I attended an afternoon seminar on retirement and tax planning at the Days Inn in Tampa. When it was over I stayed and talked to a guy who had answered a question that I wanted to get some further information about. When we were done, the conference room was empty, and after he got on the elevator, I went to the men's room to take a leak. It was deserted, I checked all the shitters. There were two urinals, so I stood in front of the right hand one and...
Oral SexTo enjoy this story, you don't need to know about the Overwatch cast, but it'll certainly help. Though at this point, I assume almost everybody has at least heard of the game. If your preferred character doesn't lead to a path yet, feel free to like it and return at another time, and hopefully something will be written. Feel free to "like" your favourite paths. It definitely helps with knowing what people like the most, especially if some have certain characters they'd prefer to follow! Join...
There are times, though, like late on Christmas Eve when I was trying to assemble that damn bike, that I wished I had a man around. Not because I can't handle a hex wrench, mind you, and besides, if that was all I needed I could have asked Troy for a hand. No, I just missed sharing the warmth of the holidays and the Christmas memories. And there's no reason I should be alone - I'm an attractive brunette with a nice figure, and at 41, I'm barely over the hill. But I always seem to hook up...
He always loved late autumn afternoons when the sun shown through the trees at a low angle and painted the grounds in warm yellow light. The manicured lawns, framed by the tree overhangs were made lush green by the light. He had spent many hours over the years with his master gardener to design these grounds. Between the two of them they had created a masterpiece. Every view from the House was beautiful regardless of the time of year but autumn was the best. Reluctantly he turned from the view...
The Real Stepford Wives: Lizzie's Story By Emma F Author's Note: This story is a prequel to my prior story, "The Real Stepford Wives: Sophia's Story". Both stories are based on Sarah Barndt's original story "The Real Stepford Wives: Only Women Have Babies" and "The Real Stepford Wives: Sugar Plum Fairy" written by VI several years later. Sophia, along with some of the characters in the other two stories make cameo appearances here. *************************************** I...
The Real Stepford Wives - Vicky's Story By Emma F Author's Note: This is my third entry in the Stepford Series. This story is a prequel to my prior story, "The Real Stepford Wives: Lizzie's Story". Both stories are based on Sarah Barndt's original story "The Real Stepford Wives: Only Women Have Babies" and "The Real Stepford Wives: Sugar Plum Fairy" written by VI several years later. Lizzie, along with some of the characters in the original two stories make cameo appearances...
The Real Stepford Wives: Sophia's Story By Emma F Author's Note: This story is based on Sarah Barndt's original story "The Real Stepford Wives: Only Women Have Babies" and "The Real Stepford Wives: Sugar Plum Fairy" written by VI several years later. Some of the characters in those stories make cameo appearances here. ********************** I was four years into my career as a Big Four accountant. Two years ago, I had been promoted to senior associate and was hopeful about...
Introduction: Harry, Ginny, Hermione, and Ron get lost in the forbiden forest and finaly let their feeling for each other show. Ron and Hermione were strolling around the black lake, they werent actually dating but they were doing all the normal couples stuff except for the kissing and sex. They saw two people in the distance walking towards them. Is that Harry and Ginny Hermione asked. The red hair was unmistakeable and ten minutes later they sat down on the bank as Harry and Ginny (who were...
Hi Dear ISS readers. I am a very big fan of the Maid Servant and Office/Teacher section of this website since 2001 but could not dare to write my experiences on the site. My latest sex partner encouraged me to write all my experieces so that I can get fans out of this and could also get some pleasure if I am Lucky. Let’s get on to my experiences. My ‘key’ name (like pen name for writers of olden days, so is my key name that I am typing on my keyboard) is Feliz. I am 5’11” tall and have an...
IncestLizzie and I are partners. Not in the romantic sense, more like a business partnership. I’m a first-class introvert, living quite isolated out in the country and mostly interested in my projects and learning new technical stuff. It’s paid off pretty well. My royalties have been well into the six digits for the past few years and if I’d meet with business people more often it could be more. That’s where Lizzie helps out. She’s going to college for a business degree and is learning to interface...
The Real Stepford Wives: Sugar Plum Fairy By VI This story is based on my favourite piece of TG fiction, which was written by the author Sarah Barndt. If you have never read 'The Real Stepford Wives: Only Women Have Babies' then please do so, as it is an imaginative and well told story. Thanks very much Sarah. ************************ I had been performing ballet since I was eight, and for the last six years had been with one of the American ballet companies. I think the fame...
This story is meant for free fan distribution to TG fiction sites throughout the web. Please enjoy the story and be free with your comments or critiques! ============================================================ Fork Leaf Clover: SHAMrock Stand-In II By Dee Eon Kicking heels high after my slippers' metal taps clicked and rapped the parquet floor like a machine gun below my long legs and flouncing embroidered clover green velvet skirt, my passionate solo jig to the...