Isla Gets a Man (& Olwen Does Too)

Reading notes: I am both flattered and proud to announce that a loyal follower, who is also a regular commentator on my writings has contacted me with an outline of a story she has come up with. I have developed her storyline into the following tale. It is obviously total fiction, but I have included myself and my cuckold in it for dramatic purposes. The character of Isla (not her real name, but not too far off either!) is based on my follower, (with her permission and approval) and her initial storyline. Apart from Isla, myself and my cuckold, all other characters mentioned in the following tale are figments of my imagination. That having been said, it is important to state that all sex described in the following story is consensual and takes place between people aged eighteen or older. Please consider commenting after you've read this tale, and also consider using the star scoring system. Whatever you choose to do, enjoy the story.

It was a Friday night in the Simpson household. Dinner had been eaten, and now Olwen Simpson was enjoying the last of the bottle of wine that had accompanied the meal. She was sitting in the conservatory, sipping her drink and smoking a bowl of her favourite aromatic tobacco in her dainty lady churchwarden pipe. When Richard, her cuckold husband had finished cleaning up in the kitchen, he'd join her in the conservatory and be allowed to watch her smoke whilst Olwen decided how the rest of the evening would be spent.

It was unusual for Olwen and Richard to be at home together on a Friday evening. Normally, Olwen had a date with one of the two men she had been seeing on a regular basis for several months. If she was on a date with Gareth, Richard would drive her to his house and either wait outside in the car whilst his Hot Wife got herself well and truly fucked, or if Olwen was in a mischievous mood, she'd take Richard in with her and make him stand in the corner of the bedroom. He'd either be allowed to watch, or he'd be made to face the wall, where he could hear and smell what his Hot Wife was doing, but not see. Richard loved the latter scenario. It was so utterly thrilling and humiliating.

If Olwen was with Andrew, she'd walk to his house on the next street, leaving her cuckold home alone, to contemplate the fact that she would eventually return with a cunt brimming with cum, which she would then insist that he cleaned up. Richard loved eating cream pie.

But tonight was different. Gareth was away for the weekend, on an outward bound course with a group of pupils from the school where he taught. Andrew was also away, but only for a couple of days. He and his wife, Deb. were swingers, something that Olwen and Richard had been involved in, until Richard's propensity for cumming after about thirty seconds of getting hard, meant that invitations to swinging parties eventually dried up. Following this, Olwen had become a Hot Wife, Richard a cuckold, and it was a lifestyle that both of them enjoyed immensely.

"All done, dear " Richard announced, coming into the conservatory. His nostrils flared and his eyes sparkled when he saw Olwen smoking. A non smoker himself, he had a huge smoking fetish, and he loved watching his Hot Wife smoke. Olwen used cigars as well as her collection of various pipes, and whenever she smoked, Richard's cock reacted as best as it could to the sight. Richard was permanently cock locked.

Olwen drew on her pipe and exhaled through her nostrils. She looked like a pretty, fierce little dragon.

"Show me," she said quietly, and Richard lifted up the skirt he was wearing to display his cock, which as usual was locked away in a heavy metal chastity device. His tiny ball sac bulged. He hadn't been milked for almost a fortnight, thanks to the fact that last Saturday's milking had been cancelled. Richard had forgotten to pick up Olwen's weekly supply of tobacco when he was out shopping. He'd been on his best behaviour since then, and Olwen was looking forward to draining his balls on Saturday afternoon. She nodded to herself, and blew a stream of creamy white pipe smoke over Richard's cock lock and his balls.

"You're going to have quite a load to recycle tomorrow," she teased him. "It'll make up for the lack of cream pie tonight. But don't fret. When I've finished this bowl, we'll go to bed and I'll peg you before we go to sleep."

"Thank you, my dear," replied Richard gratefully. "Would you like me to switch the television on? There's never anything worth watching on a Friday night, but perhaps you might like to look at a few clips on that new Hot Wife and cuckold porn channel?"

"Yes, why not?" replied Olwen. "I particularly liked that clip you found the other night. The one where that Hot Wife verbally humiliates her cuckold whilst he's watching her getting fucked. Put that one on."

Richard set about finding the clip that Olwen had mentioned. Whilst she waited for him to log into the porn channel they subscribed to, she heard the front doorbell ring.

"I'll go," she said, setting her pipe down and getting to her feet. "We're not expecting anyone, are we?"

As she went out of the room, the phone started to ring. Olwen tutted.

"Richard," she called, "get that, will you? I can't answer the phone and open the front door at the same time."

Olwen did a double take when she opened the front door. Standing there was Isla, her colleague from work, and an occasional visitor to the Simpson household. For a moment, the two women stared at one another, and then both spoke at the same time.

"Hello Isla," said Olwen in a puzzled tone. "Have we arranged a play date then? I must have forgotten."

Isla smiled and began speaking at exactly the same time as Olwen.

"Look, I'm really sorry to turn up unannounced and unexpected," she blurted out desperately, "but I think I might have fucked up. Do you think I could come in and explain what's happened? I value your advice, and I want to know how to face things in school on Monday."

Because she'd said less than Isla, Olwen heard the last couple of sentences clearly. She smiled at her friend and colleague.

"Don't stand on the doorstep," she said, moving aside to let Isla in. "Come in. You're lucky to find me at home on a Friday night. Both Gareth and Andrew are away this weekend. Richard and I were just going to watch some porn. But now that you're here, maybe we can have some fun. Richard loves to watch me dominating a submissive."

Isla blushed, and took off her coat in the hallway.

"When you hear what I've gone and done, you'll do more than just spank me," she said nervously, and Olwen was alarmed to see tears in her friend's eyes.

"Come away in," she said, putting her arm around Isla and leading her down the hallway and into the conservatory. Richard got up as the two women entered and smiled warmly at the rotund, petite guest accompanying his wife.

"Hello stranger," he began. "Well, this is a coincidence. I've just been talking about you."

"Not now, Richard," Olwen warned him sternly. "It seems Isla has fucked up somehow. She and I need to talk. Go and make us a pot of coffee, and when we've finished, I might let you watch me spank her. She's going to eat my cunt too."

Isla sat down, seemingly oblivious to the plans that were being made for her. An unmarried woman, she gave the impression of being a typical 'old maid spinster'. The truth could hardly have been further from this impression.

Isla was a submissive bi-sexual, who took every opportunity she could get to be punished, humiliated and fucked. Unfortunately for her, these chances didn't come frequently enough, which was why she sometimes visited Olwen for a good beating, some cunt worship and, if Olwen was in a good mood, a deep strap-on fucking.

Olwen looked to be up for some play tonight, she thought to herself. She wondered how Olwen would be feeling when she'd heard Isla's confession? Time would tell, and now that Richard had been sent to make coffee, it seemed that there was no time like the present to get her guilty feelings out in the open. Isla cleared her throat and began to speak.

"It's Carl," she began, referring to the newly qualified teacher who Isla was mentoring in the school where she, Olwen and the young man all taught. "I think he's got the hots for me, and so just before we left school this afternoon, I gave him the old 'come hither' look.

Olwen sighed. Isla seemed to lurch from one disasterous relationship to another.

"What happened?" she asked, drawing gently on her pipe and exhaling a cloud of aromatic smoke into the air.

"He looked as if he'd shit his pants, and he excused himself without a word," Isla replied, blushing furiously. "How the fuck am I going to mentor him now if he thinks I'm after him, but he finds me so repulsive?"

"You're a fucking idiot," Olwen said with a smile. "You leave Carl to me. I'll tell him that you're just a frustrated, dried up old spinster who yearns for some cock. Don't worry," she added, "I won't let on that you love to be spanked too. Speaking of which..."

Olwen put her pipe down and patted her thighs.

"Come on," she said, "get over my knee. I'll warm you up with a nice hand spanking, then when Richard eventually brings the coffee, we'll have a cup before I cane you. You are going to have a very sore arse before I finish with you tonight!"

"And a well fucked cunt?" asked Isla hopefully. She got to her feet and hoisted up her skirt. Olwen smiled. Isla was wearing old fashioned stockings that required a suspender belt to keep them up. She also had 'forgotten' to put any knickers on, and her cunt seemed to glow in the subtle light of the conservatory.

Before Isla could get over Olwen's lap, there was a pinging sound which Olwen recognised immediately. Richard had sent her a text, and the tone of the alert was such that she knew she had to look at it immediately.

She tutted and stood up.

"Sorry," she muttered to Isla. "I have to take this."

Olwen unzipped Islaa's skirt and let it slide to the floor.

"Go and stand in the corner, facing the wall," she instructed her colleague. "We'll forget all about warming you up with a handspanking. You're going to get the cane and then I'm going to fuck you senseless!"

Isla grinned to herself as she took up her position, her ample arse on display. She mentally urged Olwen to hurry up. She desperately needed to be caned and fucked.

Olwen meanwhile was looking at her phone.

"Your parcel is ready for collection," her text read. Olwen swallowed nervously. The message was a code that she and Richard used to tell one another that something extremely important had come up. It was innocent enough that if a stranger happened to see it, no suspicions would be aroused. But Olwen knew that any message from her cuckold that contained the word 'parcel' meant she had to contact him immediately.

"I'll be back shortly" she told Isla. "Don't move. And keep your fingers away from your cunt!"

Olwen hurried down the hallway into the kitchen, where she knew Richard would be, making the pot of coffee she'd ordered. To her surprise, when she got there, Richard was sitting at the kitchen table and opposite him was... Carl, the young man Isla had propositioned earlier.

Not able to hide her shock and surprise, Olwen blurted out, "What the fuck's going on here, Richard?" before recovering her self control and smiling sweetly at her young colleague.

"Please excuse my language, Carl," she said, smiling sweetly. "Good evening. This is an unexpected surprise. I wasn't expecting to see you again until Monday morning."

"I did telephone earlier," Carl said nervously. "I'm so sorry to intrude like this. It's just that I wanted to warn you that something happened in school today, and that you might get a complaint about me. I wanted to give you the heads up, that's all. I spoke to your husband on the telephone a few minutes ago, and he told me it would probably be better if I came round and explained my problem to you face-to-face."

Olwen nodded slowly.

"Did he indeed?" Olwen said curtly. She looked at Richard, who shrugged helplessly and tried to explain his actions. Olwen shut him up with a glare that didn't bode well for later on.

"Right. I see," she said slowly, pulling out a chair from under the kitchen table and sitting down. She looked at Richard, an idea forming in her head.

"Out," she said sternly. "Go and wait for me in the conservatory, and don't touch anything. I'll join you in a couple of minutes."

"Yes dear," replied Richard meekly, getting to his feet and slinking out of the kitchen.

Carl looked at Olwen and grinned.

"You're magnificent," he said warmly. "I love the way you control your husband."

"He's my cuckold too," Olwen said, reaching over the table and taking Carl's hand. "This is about Isla, isn't it?" she continued. Carl's mouth opened and shut like a fish out of water.

"How did you know?" he whispered as if speaking any louder would incriminate him further.

"Because Isla is at present in my conservatory," Olwen said with a huge grin. This evening was turning out to be much more fun than she'd dared to imagine.

"She's told me that she came on to you and that you fled. Why? Don't you want to fuck her?"

Carl did his fish out of water impression again, and Olwen giggled.

"Um... it's like this, you see," Carl began. "Ever since I turned eighteen, I've always had the hots for... how can I put this diplomatically? For the old... um... no... for the more mature woman. I find women of my own age fickle, shallow and very unadventurous. Mature women have been there, done it, and in many instances got the T shirt too."

"I don't understand," lied Olwen, who foresaw her plan falling into place perfectly.

"Isla's a mature woman. She gave you a signal that she was available and you ignored it. Worse, you left without a word."

Carl blushed a deep red and shuffled uncomfortably on his chair.

"It's not just mature women that turn me on," he said, his cheeks burning with embarrassment. "I like to dominate too. I want the woman I'm with to do exactly what I say, and I like to spank them before I fuck them! Since we're being so honest, I should admit to you that I'd fuck Isla at the drop of a hat. But I'd love to spank her before I fucked her!"

He blushed a deep red and carried on.

"You turn me on too, Olwen. I never knew that you were a Hot Wife until a few moments ago. I realise what a strong woman, you are, and I dare say that there isn't a submissive bone in your body. I'd love to fuck you too. In front of your cuckold. Would that work, do you think?"

Olwen winked at her young colleague.

"Let me tell you a story," she began with a sly smile. "Many years ago, when Richard and I had been married for about two years..."

Twenty minutes later, Olwen picked up her mobile phone and texted Richard. She waited until she'd had a reply and then she stood up.Pulling Carl to his feet, she leant forward and gave him a quick, very platonic kiss on the mouth.

"Ready?" she said with a wink. "Don't forget. Don't say a word until I give you the nod."

"I won't," whispered Carl, and Olwen giggled. "They can't hear you from here, you silly bugger " she teased. "Come on! We're all going to have a very enjoyable Friday night, I think!"

Hand in hand, Olwen and Carl made their way down the hallway into the conservatory. She stopped off on the way to pop into the cupboard under the stairs, where her box of toys was kept. When she emerged, her hands were full, and Carl grinned when he saw what she was carrying. What a sight greeted them both when they arrived at the conservatory.

Isla was still where she had been told to stand, her ample, pale arse on show for the world to see. Beside her, also facing the wall, and with his arse on display, stood Richard.

Carl looked at Olwen and grinned. Olwen put her finger on her lips to ensure Carl remained silent. She put her toys down and began to unbutton her blouse, silently making signs to indicate that her young colleague should undress too.

When they were both naked, Olwen looked at Carl, whose eyes seemed to resemble organ stops. Olwen did have a very attractive, very large pair of tits, and her nipples looked, to Carl at least, very suckable indeed. He also seemed very impressed with her smooth, shaved cunt.

For her own part, Olwen was mightily impressed with Carl's cock. It was beginning to stir, and would, no doubt, be even more magnificent when it was fully hard. It was time to do something about that, Olwen decided.

She picked up a blindfold from the pile of toys that she had retrieved from under the stairs. Quickly and efficiently she put it on Isla. Only when it was in place did she speak.

"Can you see anything at all?" she asked Isla, holding her by the shoulders, and feeling her colleague trembling with terror or anticipation, or maybe even a combination of both.

"No," came the answer, "why do I need a blindfold, Olwen? I'm not sure I like this game."

"You won't be required to wear it for too long," Olwen assured her, "but for the moment I want to deprive you of the sense of sight. It will heighten your other senses. Now stand still. I'm going to remove your blouse."

Olwen unbuttoned Isla's blouse and took it off, exposing her two huge tits encased in a bra that looked as if it was struggling to contain them. Popping the clasp at the back, Olwen slid the shoulder straps down and removed Isla's bra with a flourish. Carl licked his lips as he saw Isla naked for the first time.

"It's time," Olwen said softly, kissing Isla full on the mouth. "Are you ready to be punished?"

"Yes please," smiled Isla, who seemed to have forgotten her dislike of the blindfold. Olwen led her carefully over to the large pouffe in the conservatory. She positioned Isla over it carefully, and allowed her to find her own balance. When Isla seemed happy in her position, Olwen addressed Richard.

"Come here cucky," she said, and Richard did as he was told.

"Lie down there, in front of Isla," Olwen continued, and when he was in position, Olwen sat down on his face. She took both of Isla's hands in hers.

"I'm here, Isla," Olwen informed her colleague. "I hope you are going to enjoy this as much as I am. Right, young man, you may begin. This slut needs her some stripes on her arse before she's fucked. Please give her a bloody good caning!"

"What?" screeched Isla. "There's someone else here? Olwen! What have you done? You never mentioned... ow!"

Carl had picked up a thick bamboo cane and without warning had brought it down sharply across Isla's ample buttocks.

"Shush, slut," he muttered in a gutteral growl which didn't sound like him at all. Incredibly, Isla obeyed.

"I beg your pardon, Sir," she whimpered. "That's one, thank you. Would you like me to count my strokes out loud?"

Olwen looked up at Carl, who shook his head.

"You'll remain silent," Olwen instructed. "And if you're a good girl, and take your punishment well, I dare say you'll be rewarded with some lovely cock."

"Yes, Mistress. Thank you," replied Isla and she yelped as another vicious stroke landed squarely across her arse cheeks.

When Carl gave her a third stroke, Olwen noticed that his cock was twitching. She longed to have it in her mouth, but she resisted the temptation and continued to hold Isla's hands, preventing her from rubbing what was undoubtedly becoming a very sore arse indeed.

Carl used the cane beautifully. Olwen admired the series of parallel lines that were becoming redder and more evident on Isla's arse. Isla herself was obviously in a good place. Each stroke now brought a murmur of pleasure from her.

As Olwen watched Carl brought the cane down hard once more and Isla squirmed on the pouffe. He put the cane down and felt between Isla's legs. Olwen heard another moan of pleasure and then Carl came closer and offered her the two fingers that he'd obviously inserted into Isla's cunt. They glistened with her cunt cream.