Training Wendy For Her New Role Ch. 03

The story so far: Olwen has agreed to mentor Wendy, a staid English actress, who has become disillusioned with being typecast. She has asked her agent to get her a role in an adult film, and Wendy is staying at the remote home of Olwen and her cuckold Richard in order to learn about the lifestyle of a Hot Wife and a cuckold. At the conclusion of Chapter 2, Wendy was being allowed to give Richard his regular Saturday afternoon milking.

There was a hiss of agony from Richard and then Wendy announced, "I'm in!"

She steadied herself by gripping Richard's waist and then, gently at first, she began to move back and forth. For a novice, she was doing one hell of a job of pegging my cuckold.

I switched my rabbit on and a low buzz filled the room. It was accompanied by the regular slap of Wendy's thighs against Richard as she built up a rhythm. The only other sounds in the room were Wendy and my heavy breathing, and the occasional whimper from Richard.

"Don't forget, cucky," I said breathlessly as my juices started to flow, " you need to inform Ms Wendy and myself when you start to cum."

"Yes dear," replied my very submissive cuckold.

END OF CHAPTER TWO. NOW READ ON...

Things were developing nicely as Wendy continued to peg Richard and my rabbit induced a lovely warm, wet feeling in my cunt. Then the bloody phone started to ring.

"Fuck's sake!" I muttered, and I scrambled off the bed and hurried downstairs to answer it.

I could see from the caller identification display that it was Cindy, my best friend and fellow Hot Wife, so I picked up the phone.

"You know just when to ring," I mock scolded her. "I'm just watching Wendy pegging Richard. This had better be important!"

"Darling, I've fucked up," Cindy began, and I could tell from the tremour in her voice that she was really upset.

"What's wrong, Cin?" I asked. "Can I help in any way?"

"I hope so," Cindy replied. "Jonathan's on his way here with a friend that he is hoping to recruit to his Wife Fuckers Club."

Jonathan was Cindy's younger brother, a handsome rogue who got away with most things due to the fact that he had a huge cock which was capable of fucking a woman, cumming like a waterfall and being ready to go again a few minutes later. I knew all this because a few years ago, he'd fucked me, and Richard had commented that he'd never had such a massive cream pie to clean up.

I also knew that Jonathan came home occasionally to fuck his big sister. He had a high powered job somewhere in the City of London, and had formed an exclusive club together with some of his fellow workers to de-stress at weekends. This club went by the name of The Wife Fuckers, and the clue was in the name. Both Cindy and I were honorary members, and had enjoyed a couple of sessions with Jonathan and his friends.

"So?" I asked, in answer to Cindy's statement that her brother was on his way. "Don't tell me you can't manage the both of them? I know for a fact that you do double penetration better than most of us. What's the problem?"

"The problem is this," Cindy replied patiently. "I've been nagging Neil to get us an invitation to this society I'd heard about ages ago. It's a Swinger's Club, but one with a difference. All the women are Hot Wives, and they have parties with their boyfriends and their bulls. But they bring their cuckolds along for clean up."

"That sounds like fun," I replied. "I wouldn't mind going to a party like that."

"You have to be recommended by a member," Cindy explained. "Once you've been to one party, you're in, so to speak, and can recommend someone else. Neil's been trying to get a recommendation for months. And of course, Sod's Law says that the very weekend my brother and his potential recruit come to visit, Neil and I finally got an invite to attend one of these exclusive parties."

Cindy sounded both excited and yet frustrated.

"If we don't go, we'll never be invited again," she continued. "Look, darling, I know you've got your hands full with you-know-who staying with you. Sidney is thrilled with her progress, by the way. He's coming to the party with me tonight, of course."

I knew what was coming next, and my clit, already awake thanks to my rabbit, and begging for more stimulation, twitched.

"Do you think you could look after Jonathan and his friend tonight?" Cindy implored. "Under the circumstances, I wouldn't impose on you, but I'm desperate. Can you leave Wendy to look after Richard for the evening, and come round here and fuck Jonathan and his mate?"

"I don't know, Cindy," I teased. "Wendy's still learning the ropes. I don't think she's ready to play unsupervised yet."

"Oh bollocks!" wailed Cindy. "Isn't it fucking typical? An opportunity like this comes along, and now I'm going to have to tell Neil that he's not going to be able to fulfill his wish, and join the most exclusive Hot Wife and cuckold Swinger's Club in the country after all! What a bummer!"

I giggled.

"Cindy, my darling, you are so easy to wind up," I said down the phone. "Of course I'll entertain your lovely brother and his friend tonight. And I'll do even better than that. I intended taking Wendy down to the club tonight. She needs to get fucked. I was going to take her seeking, but now I don't have to! Two eligible men have appeared just in the nick of time! What time do you want us there?"

"We'll have to leave in about an hour," replied Cindy. "Neil's driving, of course because Sidney and I will be sitting in the back, getting ourselves ready for a night of sucking and fucking! And Jonathan and his mate, he's called Sebastian by the way, are due here by seven o'clock. So I'll leave him a note on the kitchen table. Do you want to come here, or shall I send them up to you? Or, as you were intending to go to the club this evening, do you want to meet them there?"

I considered all three options, and eventually reached a decision.

"I'll bring Wendy down to yours," I replied. "It will be fun to leave Richard home alone. He'll have been milked by then, so he can watch some porn and be ready to clean us both up when we get back. I think Jonathan will be happier operating on familiar territory."

"Darling Olwen, you're a life saver!" gushed Cindy. "I owe you big time!"

"Yes, you do," I chuckled, "and I'll be calling in my debt at some point."

"Anything for my best friend and fellow Hot Wife," Cindy promised. "Must go, darling. My cunt hair is stubbly and needs a trim!"

"Enjoy yourself, you dirty bitch!" I quipped. I knew exactly the favour I was going to extract from Cindy as a reward for saving her bacon. She'd said 'Anything.' I wondered if 'Anything' included letting me strap on and fuck my sexy, but strictly heterosexual best friend?

I hurried back upstairs. I could hear Richard whimpering and Wendy's heavy breathing before I got into my bedroom. What a sight greeted me when I entered the room!

Wendy was really giving Richard what for! She thrust in and out of his arse vigorously, and his legs were beginning to go. He looked up as I got back onto the bed and smiled weakly at me.

"I'm right on the edge," he gasped. "I can feel that I'm about to cum."

I looked at Wendy, whose face was flushed and her mouth was slack as she worked hard at pegging my cuckold.

"You're doing a great job," I encouraged her. "He'll start oozing in a minute. Don't stop now. We want him drained, remember."

"This is bloody hard work!" Wendy gasped. "My thighs are screaming! Can't I stop once he starts to cum?"

I thought for a minute and considered the possibilities.

"Okay," I agreed. "Richard, tell us when you feel the first pulse oozing out, and Wendy can stop. I'll take over and get the rest out of you with my fingers."

"Yes dear," replied Richard. "It's starting now, actually."

Once more, I got off the bed and went to look at Richard's condom covered cock. I winked at Wendy.

"Good job!" I complimented her. "Go and have a rest on the bed. I'll take over from here."

Wendy pulled out of Richard's arse, causing him to yelp in pain. Her ribbed dildo glistened with his arse secretions.

"When you're ready, put that in his mouth," I told her. "He can clean it up whilst I'm milking him!"

Wendy grinned and hopped up onto the bed. She knelt down in front of Richard, her cock sticking out lewdly from between her thighs. Richard opened his mouth and she slid it in gently.

His arsehole, meanwhile, was still gaping after the dildo's attention. I slid three fingers easily into him and immediately located his prostate. I began to stroke it and the slow, steady flow of cum continued to ooze out of him.

In the fifteen minutes or so that it took to drain Richard's balls, he'd cleaned up Wendy's dildo, and our house guest had taken her harness and dildo off and was now pleasuring herself with my rabbit.

"I'm all out, I think, my dear," Richard informed me, and I extracted my fingers and started to release him from his bondage.

He stood up with a groan and I bent down and took the leg spreader bar off his ankles. His little cock was still hard, and the condom bulged with a week's worth of cum. I winked at him and he grinned.

"Take it off carefully," I instructed him, "and show Wendy how your milking session finishes."

Wendy watched, fascinated as Richard removed the condom. He looked at me and I nodded my permission. He put the open end in his mouth and squeezed, emptying his cum into his mouth.

Wendy giggled.

"Does it taste nice, cucky?" she teased. She looked at me and smiled.

"Thank you," she said sincerely. "That was very intense. My first ever pegging! I never realised how hard it would be. My legs are still aching!"

"We'll go and have a nice warm shower in a minute, " I said, sliding next to her on the bed. "That should get you nice and fresh again. You don't want to be stinking of sweat when we go out later on."

"Oh yes, I forgot," Wendy replied. "You're taking me down to your sex club, aren't you? I'm going to have to dye my hair before then."

I shook my head and winked at her.

"Not necessary, my dear," I informed her. "We're not going to the club after all. That was my doctor friend Cindy on the phone."

Both Wendy and Richard looked at me expectantly.

"Cindy and her bull are going to a Swinger's party this evening," I began my explanation. "You might be interested to know Wendy that Ciny's bull is your agent, Sidney. He's been fucking her for some time, as I understand it."

Wendy's face was a picture. She shook her head in amazement, and I continued.

"So, it turns out that Jonathan and his friend Sebastian are visiting this weekend. They were expecting Cindy to accommodate them, but she's not going to be there obviously. I volunteered us both. I hope you don't mind?"

"Who on earth are Jonathan and Sebastian?" Wendy asked slowly. "They sound like some sort of folk singing duo!"

"I think you'll find that 'Folk singers' is way wide of the mark," I smiled. "Jonathan is Cindy's younger brother and although I've never met Sebastian, I'm told that he is looking for the same thing as Jonathan."

"And that is...?" said Wendy slowly, her face breaking into a huge grin as the realisation sank in.

"Correct!" I confirmed, "they're looking for a night of sex. We're going to get ourselves fucked, my dear. And the bonus is that you won't have to disguise yourself at all. We're going to Cindy's house, not the club."

Richard drove us, of course. He seemed disappointed that he wasn't going to be allowed to stay and watch, but I'd reasoned that as I'd never met Sebastian, I didn't know if he'd be comfortable with my cuckold present. Richard accepted this argument, of course. He's been a cuckold long enough to know that when I say something in my role as a Hot Wife, it is not negotiable. That's how a Total Power Exchange works!

"You can watch your favourite porn channel whilst Wendy and I are out," I instructed him as he dropped us both off outside Cindy's house. "Be back here at eleven o'clock, and don't be late! Wendy and I will each be carrying a nice cream pie for you!"

Wendy giggled.

"Thank you dear," replied Richard sincerely. "Enjoy yourselves, and give my regards to Jonathan."

As he drove off, Wendy turned to me.

"Your husband, sorry, I mean your cuckold is a remarkable man," she said with a smile.

"Yes he is," I agreed. "I love him more than anything in the world. I just wish he had a bigger cock!"

We walked up the garden path hand in hand, giggling like naughty schoolgirls.

I rang the doorbell and Jonathan opened the front door immediately. He must have been lurking in the hallway, I thought. His face broke into a huge grin when he saw me.

"Olwen!" he grinned, extending his hand and pulling me gently into a warm embrace. "My sister left a very enigmatic note on the kitchen table. She and Neil are away for the evening. I was so looking forward to seeing my big sister again. But in her absence, you are a very acceptable substitute."

I didn't let on that I knew that Neil, Cindy's cuckold, was only accompanying her as a chauffeur, fluffer and clean-up man. Cindy was going to be looked after by her lover, Sidney.

Jonathan looked at Wendy and smiled.

"Good evening, Olive's friend," he said, extending his hand once more to shake Wendy's hand. "I'm Jonathan. Welcome to my sister's house."

"Thank you," replied Wendy, "I'm Gwendoline and I'm very pleased to meet you."

"Come in, come in," Jonathan stood aside and waved us into the house. "Come into the conservatory. My friend Sebastian will be very pleased to meet you both."

As we strolled through the huge house, Jonathan took my hand.

"I really enjoyed our last encounter," he confided in me. Dropping his voice to a terrible stage whisper, he added, "Your friend, Gwendoline looks rather familiar. She does know what's going on here, doesn't she?"

I noticed Wendy's shoulders tighten as she walked ahead of us, but she gave no indication that she'd overheard Jonathan.

"Of course she knows, don't you Gwendoline?" I answered in an ordinary conversational tone.

Wendy turned round, winked at Jonathan and licked her lips in a most obvious and deliciously filthy gesture.

"I understand you gentlemen need some relief," she said in a very sultry voice. "Olwen and I are Cindy's substitutes. She's off with a very good friend of mine, and I imagine that at this time of the evening, she's just about ready for some cock. Just as Olwen and myself are hoping to get very soon!"

Jonathan burst into laughter.

"Oh, I like you!" he said. "I'm sure Sebastian and I will do our best not to disappoint you!"

"So glad to hear that," Wendy replied. "I hope you like foursomes. Olwen and I operate as a team after we've both been fucked a few times!"

Jonathan appeared to be struck dumb by this revelation. He looked from Wendy to me and back again.

"Are... are you ser...serious?" he eventually managed to gasp.

"Perfectly," I replied, pulling Wendy close to me and kissing her full on the mouth.

"Oh, fucking hell!" moaned Jonathan, "I was going to suggest that we crack open a bottle of bubbly to break the ice, so to speak. But the ice hasn't just been broken. It's fucking melted! You two are really fucking hot!"

Sebastian was lounging on one of the three settees in Cindy's huge conservatory.A tall, well built man, with beautiful cafe-au-lait coloured skin, he looked very fit and his pristine white T shirt was tight enough to show that underneath the garment, his torso was taut and muscled. As we entered, he sprang to his feet and his face broke into a huge grin.

"Welcome, ladies," he began. He looked at me.

"You must be Olwen," he said, extending his hand for me to shake. "I'm so pleased to meet you. Jonathan's told me so much about you."

"I hope he did me justice," I replied, shaking his hand. "A girl does hate to be under sold!"

Sebastian roared with laughter. He turned to face Wendy.

"And you must be... fucking hell! You're Wendy Craig! I love your shows on TV. I hope you'll allow me to get to know you a bit better? Don't worry, we're all alone here. There'll be no need to worry about 'Not In Front Of The Children'. We're all adults here!"

"Don't be a cunt, Seb," said Jonathan harshly. Miss Craig is here as a friend of my sister. So you know one of her more famous television series? Big fucking deal. What if Miss Craig decides that she doesn't want to stay because of some loud mouthed clever arse? You'll just have to sit there and watch me fuck Olwen. Is that what you want?"

"No, of course not," replied Sebastian sheepishly. He took Wendy's hand.

"My humblest apologies, Miss Craig," he said sincerely. "I am the soul of discretion. My lips are sealed, I promise."

"Mine aren't," smiled Wendy, sinking to her knees and unzipping Sebastian's jeans. "And a good job they're not, or I'd never be able to suck your cock!"

Both Jonathan and I watched in amazement as Wendy efficiently pulled Sebastian's cock out. It wasn't fully hard, but was visibly swelling as she gently pulled back his foreskin to reveal a smooth, shiny mushroom head.

"Hello," Wendy greeted the rapidly expanding cock. "I'm Gwendoline, and it is very nice to meet you. May I?"

She dipped her head and took Sebastian's cock in her mouth. Sebastian groaned with pleasure.

"Oh, fucking hell," he said softly, "Gwendoline or Wendy, I don't give a toss what you call yourself. You certainly know how to suck cock!"

I turned to Jonathan and winked at him.

"It seems I'm to have the pleasure of your cock first," I said, rubbing my hand on the front of his jeans. I felt his cock stirring.

"Why don't we use that settee over there? If you fuck me from behind, we can both watch these two at the same time."

"What a splendid idea," grinned Jonathan, pulling his T shirt over his head. I shucked my blouse off and wandered over to the settee. Jonathan unbuttoned his jeans and slid them down. I appreciated that he'd gone commando, so that when he stepped out of his jeans, he was almost naked.

"Socks, please," I smiled at him. "This isn't one of those dreadful porno clips where the man always seems to keep his socks on!"

Jonathan grinned, and began to tug the offending articles off. I slipped out of my skirt, revealing that, like Jonathan, I wasn't wearing underwear. My stockings could stay on, I decided as I mounted the settee and watched Wendy bobbing up and down on Sebastian's cock.

I sensed rather than saw Jonathan get into position behind me and I reached down between my legs and got hold of his cock. It was rock hard and I recalled from the last time he'd fucked me how the veins stood out all along his cock shaft. I pulled him closer and felt his cock head nestle in between my outer lips.

Gently, I wiped it up and down my slit a few times, and Jonathan groaned.

"Don't be a cock tease!" he begged. "Put it in, or I'm going to cum in your hand!"

Well I certainly didn't want that, so I spread my legs wider and backed onto him. He slid in easily, stretching my cunt and filling me beautifully. I clamped down on him, which judging from his gasp of pleasure, he seemed to enjoy. Jonathan began to fuck me slowly but he went in deep every time, and my clit emerged from her hood to join in the fun.

Sebastian's eyes widened as he watched his friend fucking me. He began to gently fuck Wendy's mouth, sliding back and forth and she took his whole length like a trooper.

"I'm gonna cum!" he gasped after a few minutes of mouth fucking, and I knew exactly how he felt. I was on the edge myself, thanks to Jonathan's gorgeous cock.

Wendy didn't seem to hear him, or if she did, she didn't break her rhythm. As I watched, I saw her cheeks bulge and Sebastian let out a howl of pleasure. He was cumming in her mouth!

That was enough to send me over the edge and I rode out my own orgasm quietly, although my whimpering must have been a real giveaway. My cunt felt as if it had been wired into the national grid, and fireworks went off down there, and in the pit of my stomach, as well as in my head.