Mentoring A Wannabe Hot Wife

I'm extremely fond of Isaac, not only because he's got such a wonderful cock. He's thoughtful and considerate too, and he realises that I need some time alone with my cuckold.

So whilst he was showering upstairs, I took Richard into my en suite bathroom. He stripped and I took the key to his chastity device off the chain around my neck. We both like the symbolism that keeping his key on a chain demonstrates. The key nestles between my tits, and if anyone not in the lifestyle happens to see it and asks why I wear a key, I tell them that it is a present from my husband, and it is the key to his heart. It really isn't that far from the truth!

Once his device is removed, Richard always gets a hard on. It doesn't bother me, because Richard hard is about the same length and thickness as my little finger. Even if I allowed him inside me, I doubt if it would touch both sides of my cunt at the same time! But I don't allow him access anyway.

First, Richard is required to clean and disinfect his device to my satisfaction. Only when he has done this do I take his fluffy pink flannel and soak his little boi clit with cold water. Then I soap him up and shave him. I much prefer Richard smooth.

Next is the milking itself. During the month of April, when Richard has a birthday, on the Saturday closest to the fourteenth, I use my hand to milk him. This treat is also given on the Saturday closest to our wedding anniversary, and also on the Saturday closest to Christmas. On every other occasion, Richard is milked using prostate massage. This particular Saturday was such an occasion.

Putting my index and middle fingers up Richard's arse always gets him hard again after his cold water shave. I've done it so often by now that I can find his prostate easily. There is no romance about the process. It is merely something that has to be done to drain him. What I particularly enjoy is seeing him start to ooze.

When most men cum when they are fucking, they spurt. Not so during prostate massage. There is no sexual satisfaction. The person being milked is drained slowly and he remains hard even when his ball sac is completely empty. The whole draining process can take up to twenty minutes, and it always leaves Richard frustrated and anxious. It also ensures his loyalty and his obedience!

I make Richard 're-cycle' his cum when he's empty, and then I lock him away for another week.

By the time I'd finished milking, Isaac was almost ready to go. I let Richard shower whilst I got into my favourite latex cat suit which I'd put out earlier in the afternoon. I'd already had my shower whilst my boyfriend and my cuckold were on the golf course.

Isaac loves to see me in my cat suit. It clings to my tits beautifully and has a discrete zip between the legs which allows him access when he wants my cunt. He wore a delightful pair of leather trousers and his favourite denim shirt that showcased his perfectly toned and muscled torso.

I put Richard's collar on him, which completed the get up I always made him wear to the club: a pristine white shirt, grey flannel shorts, three quarter socks and open toed sandals. He looked perfectly ridiculous. And he loved it!

We got to the club by about eight o'clock. It was much fuller than usual, but Hilary had reserved seats for us at her table. Freddie was sitting next to her, pawing her tits and staring at a pneumatically endowed woman who was explaining from her position on the stage, how the night's auction would unfold. Neville, Hilary's cuckold was in position, on his knees at her side. He too was collared, but unlike Richard, Neville, a committed and very effective transvestite, was 'en femme.'

Isaac sat down and I sat on his lap, wriggling to get his cock nice and hard. Hilary rolled her eyes and grinned.

"I wish I could wear a cat suit like that," she said sadly. "It shows your tits and nipples off beautifully, and I've yet to see a better example of a camel toe!"

I smiled and thanked her. I love Hilary to bits, but as she herself acknowledged, she really wasn't the shape to wear a cat suit. Standing just over four foot tall, Hilary is almost as wide. Her tits would have bruised her knees were it not for her huge belly which prevented them from banging against her legs. But she had the face and skin tone and texture of an angel. She truly was a Big Beautiful Woman in every sense of the title.

Given that neither Hilary nor I was really interested in acquiring a slave, the auction was tedious. The sums of money paid to engage the services of a wannabe slave rarely got above a couple of pounds. I suppose it is the thrill of the thought of actually being sold that attracted those who took part in the auction.

I was bored, and in need of some cock. I was just about to suggest that Richard drive us home, when there was a commotion near the entrance. I turned to see what was going on, and to my surprise, I saw Lizzie the Lezzie walking in with another woman. To my experienced eye, Lizzie's companion looked very fit. She had the body of a young woman, with pert tits and long, slender legs I couldn't see her face, as she was wearing a domino style mask, which obscured the top half of her face..

This is not unusual in the club. Many punters want anonymity; others just enjoy the feeling of being able to indulge in their chosen fetish without being recognised.

I waved to Lizzie, and she smiled at me before turning to one of her companions and saying something in her ear. The young woman looked over at our table before hurrying off and sitting down at a table with a 'Reserved' notice on it.

There were some female submissives who were offering themselves for sale, and I assumed that was the reason that Lizzie and her friend had come.

However, the next auction 'lot' was a male, whom I judged to be in his early forties,who was put on display naked. He was paraded up and down the stage and received the usual cat calls regarding the size of his cock. It wasn't huge when I compared it to Isaac's beauty, but it was certainly bigger than Richard's little boi clit. The cruder and more vociferous the abuse he received, the more his little cock twitched.

The bidding started at fifty pence, and began to climb steadily, albeit in steps of only five pence. Lots of the audience were laughing, but two women, one who looked old enough to be my mother, and another one, more my age, were in serious competition for this would-be slave.

The bidding had reached one pound fifteen pence when the older woman hesitated.

"It's against you, Mildred," the huge titted auctioneer called. "Do you want to offer one pound twenty?"

The room was silent. Most people were turning in their chairs to look to see what Mildred was going to do.

A voice from the other side of the room called out "Ten pounds bid!"

A gasp went up from the audience, and I turned to see that Lizzie the Lezzie was on her feet, waving a ten pound note and wearing a grin of triumph.

The auctioneer repeated the bid.

"Ten pounds I am bid. Anyone want to offer me eleven?"

There was silence, and the auctioneer gave everyone a few more seconds before declaring that lot number eight had been sold to Lizzie the Lezzie. When she banged her hammer down on the desk to confirm the sale, an excited buzz of conversation began amongst the audience.

Ten pounds! It was a ridiculous sum to pay for someone who, in all probability, would have offered his services for free. And what the hell was a committed submissive lesbian like Lizzie doing buying a man?

I would have loved to have found out, but immediately after the auctioneer ended the sale, Lizzie marched up to the stage, grabbed the lead that was attached to the collar of her recent purchase, and yanked him off the platform.

He stumbled onto his knees, and Lizzie jammed her ten pound note into his mouth.

"Follow me," she barked, and she led her purchase not back to the table she'd been sitting at, but out of the door, and out of sight of everyone in the club. When I looked at the table, it was empty. The masked women had disappeared.

I was intrigued, but not so much that it distracted me from my main purpose: getting Isaac interested enough to fuck me. To be fair, he didn't need much encouragement, and so barely twenty minutes later, Richard was driving us all back home for a night of sucking and fucking. For Isaac and me, that is. Richard spent the night in the spare bedroom. Before I dropped off to sleep in the early hours of the morning, well fucked and with both my cunt and my arse awash with Isaac's cum, I reminded myself to ask Lizzie what the hell she'd been up to, when I next saw her.

Isaac had some work to do on Sunday, and I had my school lesson plans to sort out. He fucked me when we both woke up, and again in the shower before breakfast. At about eleven o'clock, we kissed goodbye and arranged to meet again the following weekend. Whilst Richard set about preparing and cooking Sunday lunch, I got down to planning my next week's lessons in the conservatory.

The end of term was approaching rapidly. What with end-of-term exams, reports to write and next year's timetable to organise, I totally forgot about tackling Lizzie the Lezzie about her mysterious purchase and her equally enigmatic companion.

School broke up for the summer, and Richard and I spent a wonderful month at a Caribbean resort for swingers and fetish lovers. No-one knew us there, and we were able to walk around without any clothes on, getting a fabulous tan and eyeing up potential lovers for me. Richard wore his chastity device constantly, and no-one saw anything unusual in it. He wasn't the only cuckold present, and he enjoyed fluffing strangers and eating the cream pies that they left in my cunt.

Isaac came out for the last ten days of our holiday, and we picked up our fucking straight away. I'd only ever heard of 'Sex on the Beach' as a cocktail. Before we flew home, I'd experienced the actual deed, although it isn't something I would hurry to repeat. Don't get me wrong. The sex was fantastic, but by the end it felt as if I was being fucked by a cock wrapped in sandpaper. It took my poor clit a good three days to recover!

And soon it was almost time to begin another school year. August was drawing to a close in a blaze of warm, sunny days and September, and the autumn term beckoned. My tan was still quite prominent, but the Caribbean sun and the clear sea water had played hell with my hair. It had grown during the summer holidays, and I decided to keep it at its' present shoulder length. But it would need tidying up. I rang the salon a week before school was due to open again for the new term.

It was Lizzie who answered. She was uncharacteristically reluctant to give me an appointment, and when I asked why, she was equally reticent.

"You'd probably do better to speak to Cheryl," she said eventually, in answer to my barrage of questions. "It's Thursday tomorrow. Half day closing. Come to the salon at about two o'clock. Cheryl will be here then, and she'll explain everything."

I had little choice but to do as Lizzie said. I was going to give her a piece of my mind when I saw her face-to-face the following day, I decided.

I walked to the hairdressing salon the following day, arriving as scheduled just on two o'clock. The door was closed and a sign to that effect hung from a sticker in the glass panel, which was covered with a roller blind, thus preventing passers-by from seeing inside. I knocked loudly on the glass door, and after a few seconds, the blind was moved aside and I saw Lizzie's familiar features.

She replaced the blind and opened the door.

"Thanks for coming," she said gratefully. "Cheryl's in the salon. She's in a hell of a state."

Puzzled, I followed Lizzie into the salon. What greeted me was a sight that normally would have made me smile with pleasure, but as I approached her, Cheryl put down the cigar that she was smoking and burst into tears.

"Oh, Mrs. Simpson. Thank you for agreeing to see me," she sobbed. "I've made a dreadful mistake. I'm such a failure. Lizzie says if anyone can help me, you can. Will you, please?"

I looked at Lizzie, who merely shrugged, and picked up her own cigar from the ashtray. She puffed on it and exhaled through her nose, making her look like a fierce little dragon. I grinned.

"Whatever you've done can, I'm sure, be rectified " I said, taking Cheryl's hand and patting it reassuringly. "Now, why don't you dry your eyes and tell me what's bothering you?"

She did as I suggested, and smiled weakly at me.

"It's an awful cheek getting you involved in this," she began, her voice trembling and tearful. "But when I remembered seeing you and your little group down in the club last month, it suddenly occurred to me that you might be able to help."

I looked at her in total ignorance. I had no idea what she was talking about, and I told her as much. Cheryl picked her cigar up from the ashtray, and puffed on it. Then she got up, and went into the little room at the back of the salon, where I assumed she kept all her stock. She returned a few seconds later, leading a middle aged man, who smiled shyly at me. There was something vaguely familiar about him, but I couldn't recall where, if at all, I'd seen him before.

Cheryl made the introductions.

"Mrs. Simpson, this is Don, my husband. Don, this is Mrs. Simpson, who used to teach me. She's also a Hot Wife."

I looked at Cheryl sharply, and then transferred my glare to Lizzie. Only she could be the source from which Cheryl had learned my most trusted secret. Lizzie just shrugged and continued to smoke.

"Oh, don't blame Lizzie," Cheryl blurted out anxiously. "It wasn't her who made me aware of your lifestyle. As I said, we saw you and your cuckold down in the club last month."

The look on my face was enough to stop her nervous chatter. So it had been Cheryl who was the mysterious masked woman that had accompanied Lizzie in the club that night. And this Don; he must have been the slave that Lizzie bought. I was confused. Did Cheryl just say that Don was her husband?

I cleared my throat and spoke up. My voice sounded sharper than I intended. I'd automatically gone into 'teacher mode'.

"You'd better explain yourself, young lady," I said sternly. "I don't like what you are inferring. Come, on, get on with it. I'm waiting."

Cheryl smiled and smoked her cigar insolently.

"That's the Mrs. Simpson I know," she said with that old familiar smirk on her face. "Well, here's to nothing, I suppose."

She dropped the butt of her cigar into the ashtray and looked at me with a nervous grin.

"I met Don about eight months ago," she began, "and I knew straightaway that he was the man for me. We are both head-over-heels in love, and we got married six weeks after we met. My parents are disgusted and they've disowned me, but they are both terrible snobs. I love Don, and he loves me. And to be fair to him, Don let me know from the very start that he is a man with particular needs.."

"That doesn't bother me. As I'm sure you remember from my school days, I can be somewhat of a flirt. I thought that I'd be able to provide for my husband's needs without any bother at all. It turns out that I can't."

I shook my head in confusion.

"Cheryl, all you've told me so far is that you're married to this man," I said. "What you and he get up to as man-and-wife is no-one's business but yours. I fail to see how I can help you."

"I want to be a cuckold," Don blurted out, blushing deeply as he spoke. "I want my darling Cheryl to become my Hot Wife, and to receive the sort of loving that I can't give her. That's what she's trying to tell you."

I looked at Cheryl, who bit her lip and nodded.

"Pathetic, isn't it?" she whispered hoarsely. "Cheryl the wild child rebel of her schooldays can't provide for the man she loves."

Fat tears spilled out of her eyes, and rolled silently down her pale cheeks. I felt dreadfully sorry for her. Once again, I reached out and took her hand.

"Now then, you silly girl. There's no need for tears. Wipe your eyes and let's see if we can't set about sorting you out."

I got up and took off my coat, which I handed to Lizzie. She automatically went to hang it up, and I turned to Don.

"Coffee." I demanded. "You'll know how Cheryl takes hers. I like mine strong, with a dash of milk, no sugar. Off you go."

He grinned, knowing that here was a woman used to issuing her demands, and having them obeyed instantly, and to the letter. He trotted off happily to do as he was told.

Lizzie watched him go and said, "I'm off then, Cheryl. I have a date with my Mistress tonight. I am due my weekly maintenance spanking, and then I'm hoping to get myself well and truly fucked!"

Cheryl wished her a good afternoon and told her she'd see her in the morning. She locked the front door after her and came and sat back down. She looked at me expectantly.

"Now then," I smiled, "You want to be a Hot Wife? Well, as you so correctly assume, you're talking to one of long standing. It's a fantastic lifestyle, but not one that can be flirted with. If you're in, you have to be in one hundred and ten per cent. And both parties must agree. The lifestyle of a Hot Wife and her cuckold is totally different from the swinger lifestyle, for instance. If you're swingers, both of you get to fuck other partners. The lifestyle you are contemplating means that you decide how much sex your cuckold gets. If any at all."

Cheryl nodded her understanding.

"We've had sex, obviously," she said, blushing in a very attractive way. "It's just that Don can't keep it up long enough to pleasure me. He puts it in, jiggles about for about two or three minutes, cums and then he's out of action for hours. It's so frustrating."

I smiled at her.

"Now you know how those boys in school felt all those years ago when you used to flash your tits and arse at them," I grinned, and Cheryl blushed again.

Before she could respond, Don returned with a pot of delicious smelling coffee on a tray, complete with what looked like two cups and saucers of the salon's best bone china crockery, together with matching milk jug and sugar bowl. He was out to make an impression, so there was none of the bog standard supermarket mugs on display today.

"Very nice," I told him approvingly. "You can be mother and pour for your wife and me."

Don did as he was told, handing each of us a cup of perfectly brewed coffee. He hovered, offering milk and sugar, and when we were satisfied with our individual drinks, he made to go out again, leaving us to chat.

"Don't go," I called after him. "Your input into this conversation is vital. Get yourself a cup, and join us."

He reappeared a few moments later, carrying one of the aforementioned bog standard supermarket mugs. I nodded approvingly, and he blushed with pleasure.

"OK," I began, "I'm happy to give you both some insight into the Hot Wife lifestyle that I live. It's not a hard-and-fast rule, but I base my lifestyle on consent. Richard, my cuckold, knows everything, and consents to me doing it. He and Isaac, my boyfriend, are very good friends."

"That sounds perfect," Don said, sipping his coffee. "I recognise my shortcomings, and I want Cheryl to have a satisfactory sex life."

He paused.

"There's also the fact that I find the thought of her having sex with another man exceptionally thrilling."

He blushed, and Cheryl took his hand, smiling at him.

"Even if I do manage to get a boyfriend, I'll always come back to you," she said softly. "I love you more than I've ever loved anyone or anything before."

She looked at me in confusion.

"Am I being a hypocrite?" she asked.

"Not at all " I reassured her. "I love Richard dearly. But nature dealt him a cruel blow when she gave him a cock. It's barely three inches long fully hard, and it's as thin as a piece of string. I need filling and stretching. So I have sex with my boyfriend."