Training Wendy For Her New Role Ch. 02

"I think I'll allow her to peg you this afternoon," I said with a sly grin. "It's been ages since you were milked by pegging, isn't it dear?"

Wendy looked at me in amazement, and I smiled at her.

"Don't worry, sweetie," I assured her. "Pegging a man is almost the same as fucking a girlfriend with a dildo. You'll find Richard's arsehole will accept your cock without too much trouble. He's been pegged and arse fucked hundreds of times over the years!"

Wendy blushed and Richard reached for her hand and patted it gently.

"It will be a privilege and an honour to be pegged by such a famous television star," he assured her. "I promise to cum as copiously as I can for you, Wendy."

"Oh, isn't he sweet?" Wendy smiled. "Thank you Richard. And I promise to do my best to give you a really satisfying pegging!"

I didn't bother telling Wendy that prostate massage was the absolute antithesis of satisfying. Richard would be drained of all of his cum without the pleasure of having his cock stimulated. This desire to be constantly frustrated and unfulfilled was something that I had struggled with when Richard had first suggested it many years ago. But these days, I loved seeing the need in his eyes as he oozed cum without any sexual satisfaction. I love my cuckold, and if that's how he gets his jollies, I'm happy to provide them for him.

Richard got up from the table and started to clear the breakfast dishes away. I looked at Wendy.

"Right, my dear," I began, "once Richard's finished in the kitchen, we'll take him upstairs and dress him. He goes shopping on a Saturday morning, and I normally loll around the house until he comes home. But we have things to do this morning! I need to make a few phone calls if we're to get you a date tonight. We're going to the local fetish club, and you and I are going to get ourselves some lovely cock before the night's out!"

"I've been thinking about that," Wendy replied, and I looked at her in alarm. She wasn't getting cold feet, surely? I needn't have worried. Wendy continued,

I know I said I'd brought a couple of wigs and some plain lens glasses to disguise myself, but if I'm honest, wearing a wig is a pain. My head gets very itchy, and I bet my glasses will get in the way of kissing. And there's that saying, isn't there? 'Men never make passes at girls who wear glasses.' I don't want to mess things up for you and whoever you pick up tonight."

Once more, I didn't bother telling Wendy that one of my many fetishes is fucking women who wear glasses. Don't ask me why. I just find that women who I'm attracted to almost inevitably wear glasses. I can't explain the attraction. I might just as well try and work out why Richard, a non-smoker, loves to see me smoking my cigars or one of my many pipes. Fetishes are ingrained in all of us, and my attitude is to accept what turns me on, and not to judge other people, whose fetishes are different to mine.

Wendy was speaking again.

"Would this work, do you think?" she asked. "I'll dye my hair. I quite fancy being a red head, something similar to your shade, Olwen. I'll let you introduce me as your cousin. I can be staying with you because I'm going through a divorce, and I want some time away from my husband. But I also am desperate for some cock. How does that sound?"

I looked at her in amazement.

"I'd never have guessed that you're an actress. Someone who is used to taking on a different personality every other day," I replied admiringly. "That's perfect, Wendy! You're a bloody genius!"

"Not Wendy," she corrected me in an accent that sounded as if she came from Newcastle. "Me reel name is Gwendoline, pet. Ah'm from County Durham, and ah've coom doown Sowth to git meself fooked before me divorce!"

I burst into laughter, and Wendy blushed.

"Too much?" she asked anxiously in her normal accent.

"Not a bit of it!" I replied. "That was fantastic! Tell me, is your real name Gwendoline?"

"It is," she admitted, "and I really was born in Durham. We moved to Yorkshire when I was twelve, so if you like, Ah can talk like a Yorkshire lass too!"

Why I was amazed I can't say, because Wendy was an accomplished actress, and accents were all part of her trade. But in the space of a couple of minutes, she'd spoken in three different accents, all of which had cast her in a different light. To say I was impressed was an understatement!

Richard came out from the kitchen.

"All done," he announced. "You two sound as if you're plotting some mischief. Am I allowed to be let in on the secret?"

Wendy and I looked at each other and giggled like naughty schoolgirls.

"Richard," I began, "meet Gwendoline, my soon-to-be-divorced cousin. She's from Durham."

"Ey oop, pet! What's the craic? Ah'm over the moon to meet thee!" said Wendy, offering her hand to Richard. My cuckold took it and shook it meekly.

"I have no idea what you just said," he replied. "Does that count as English?"

Wendy smiled.

"It does," she said in her normal accent. "I've mixed some Geordie and some Yorkshire sayings up in what I just said. I'm betting that people in Wales won't know the difference."

"What did you say to me?" asked Richard, and Wendy counted out the phrases she'd uttered on her fingers.

"Well, 'Ey oop' is basically 'hello' and 'What's the craic?' means 'What's going on?'. The final bit, 'Ah'm over the moon to meet thee' means 'I'm very pleased to make your aquaintence'. It's all quite simple when you know how!" Wendy smiled.

Richard shook his head in amazement. Time was ticking away, so I got to my feet and looked at him sternly.

"Lessons are over for the time being!" I informed him. "Upstairs, now. There's my toilet to see to, and you need to be dressed. The shopping isn't going to do itself, is it? Come on, Wend... er Gwendoline. You need to see this. Welcome to the world of toilet training!"

Upstairs in the bathroom, Richard got onto his back on the floor. I sat on his face and wriggled to get into position. When he'd sealed off my cunt, I felt him lick along my slit to show me he was ready. I started to pee.

Wendy looked amazed when she heard the faint hiss as I emptied my bladder.

"You pee in his mouth?" she asked in an amazed voice. I winked at her.

"Watersports are a big part of our lifestyle," I told her, as my flow slackened and finally dried up. I got up slightly and Richard licked me dry.

"Do you need to pee?" I asked Wendy, and she blushed.

"Actually, I do," she said, so I took her hand and steadied her as she lowered herself onto Richard's face.A huge fart erupted from her arse just before she sat down.

"Sorry!" she muttered nervously, blushing furiously. "That nearly always happens the first time I pee in the morning."

"Think nothing of it," I replied. "Richard will love the aroma. Get comfortable now. That's right. Now let him seal off your cunt so that there's no leaks. When he's done that he'll lick your slit."

Wendy wriggled around a bit, then settled.

"Mmmm! That feels nice," she murmured, confirming that my cuckold had signalled that he was ready to take her golden champagne.

I smiled as Wendy began to pee. She farted again, and giggled.

"Whoops! Oh hell, I hope I don't do a number two whilst I'm down here. Pee is one thing, but poo just might be a bridge too far!"

"All done!" she said eventually. "Can you help me up please, Olwen?"

I did as she asked, and Richard licked a couple of drippers off her cunt lips.

"Thank you, Richard." Wendy looked down at my cuckold and smiled. "I'm sorry about the farting. Was it awful?"

"On the contrary," replied Richard getting to his feet, "it was rather thrilling. Your aroma went beautifully with the taste of your pee."

Brush your teeth and come to my bedroom," I instructed, taking Wendy by the hand and leading her out of the bathroom.

In my bedroom, I set out a pair of pink frilly knickers and black hold up stockings.

"Standard wear for a sissy cuckold," I smiled at Wendy. I chose a powder blue polo shirt and a pair of grey chinos for Richard to wear to the shops. Looking out of the bedroom window, the sun was shining brightly, so I put the pink cardigan back.

"Trainers, I think," I said to myself, and I selected a dazzling white pair with a pretty pink trim.

"Perfect!" I said aloud. "Ah, cucky. There you are. Come on! Shape yourself and get dressed!"

Wendy watched in amazement as Richard put on everything I'd laid out for him. As he was wearing his cock lock, he couldn't get a hard on, of course, but there was a distinct bulge in the front of his chinos. It would be obvious to anyone in the lifestyle that Richard was wearing a chastity device.

"Right. Off you go," I smiled at him. "Wendy and I are going to relax in the garden. We'll all have lunch when you come home, and then it'll be milking time. Wendy will be performing your your milking today, remember."

"Thank you, dear," replied Richard with a huge grin. "See you both later."

After he'd gone, Wendy and I went out into the garden and sat on the patio. It was getting very warm, so we moved underneath the umbrella and lay on sun loungers in the shade.

"This is surreal," Wendy said in an amused tone. "I can't believe the change in my life! I know I told Sidney that I wanted a change of role, and I suggested a porn film. But your lifestyle is just so exciting! I had no idea that Hot Wives existed. Lots of my actress friends have affairs, but they try their best to keep it a secret. You and your Hot Wife friends do exactly the opposite!"

"We do," I admitted, "but we are also extremely discrete. The lifestyle is a closely guarded secret from all our vanilla friends."

"Can I go and get a glass of water, please?" Wendy asked. "Even in the shade, it's very warm this morning."

"I'll go," I said, getting up from my sun lounger. "I think I'll have a smoke. Do you want a cigar?"

"Www! Yes please!" squealed Wendy. "I did enjoy sharing one with you last night!"

I went into the house in search of refreshment and tobacco.

By the time I got back, Wendy had taken her T shirt off and was lying with her tits out. The sight made my clit tingle and as I passed her the glass of water I brushed my hand against her naked breast. Wendy smiled.

"I hoped you'd do something like that," she said softly. "I loved the way you paid attention to my tits last night."

I sat down on my sunlounger and passed her a cigar.

"I brought a cigar holder too," I said. "I remember when I was learning to smoke, a whole cigar took me ages to finish, and the end got very soggy. Smoking this in a holder will prevent that."

I showed her how to cut the end of her cigar, and she fittied it into the holder. When she slipped the stem of the holder into her mouth, I sparked up my lighter and lit her up.

Wendy puffed gently as per my instructions, and I made sure to light all around the end of her cigar, to ensure she got an even burn. When she was satisfied that it was properly alight, she removed her holder from her mouth and looked at me.

"I thought you were going to share this with me?" she said in a puzzled voice. I shook my head and showed her my lady church warden pipe.

"You smoke a pipe?" she asked in amazement, and I nodded as I went through the ritual of packing the bowl, lighting and tamping, and ensuring that my bowl was well alight. I winked at her.

"This'll give Richard such a thrill," I smiled, unbuttoning my blouse and removing it. My bra followed the blouse and we lay in companionable silence, smoking in the shade.

After a while, Wendy sat up again.

"How exactly am I going to milk Richard this afternoon?" she asked.

I thought for a moment before answering.

"That's up to you," I answered eventually. "You can either strap on and fuck his arse till he cums, or you can hold a dildo and fuck him manually. You've proved you can wear a strap on, and use it properly, so it's up to you. I'll be there to watch, so if you have any questions, you can ask them at the time."

"I like the idea of wearing a cock and fucking a man," she smiled and she puffed on her cigar. "I've seen the script of the film, and I have to peg the man who is playing my husband. I've decided that I'm going to be smoking when I do that scene! Sidney has negotiated my contract so that I have control of my character's actions. I think I'm going to base her on you, Olwen!"

I was flattered, and told her so.

"Do you want a puff of my pipe?" I asked her. "I know for a fact that there is a large community of pipe smoking women in America. Not that they are all Hot Wives, of course," I added, "but statistically some of them must be. Go on, have a couple of puffs. I'll hold your cigar."

We swapped over, and Wendy took a gentle puff on my pipe. She exhaled the smoke and smiled.

"Very different," she admitted. "I'll speak to Sidney later on, and ask him what he thinks. I know I'm going to have to smoke something in the film. Cigar or pipe. I quite like both."

"So do I," said Richard, emerging onto the patio and looking longingly at both of us. "Has Olwen explained my smoking fetish to you?"

Wendy shook her head. She passed my pipe back to me, and took her cigar holder.

"You tell me, cucky," she smiled, and blew a stream of smoke at Richard. "Come and sit down between us and tell me all about your smoking fetish. Then, if you're a good boy, I might just milk you this afternoon!"

I was delighted. Wendy was taking to her role as a Hot Wife like a duck to water.

Richard did as he was told, and explained to Wendy how the sight of a woman with a cigar or a pipe between her lips excited him. He couldn't explain why, other than suggest that the size and shape of a cigar resembled a big cock, and he loved seeing women suck cock.

It was getting really hot, even in the shade, so we all went back into the house. The roof blinds in the conservatory meant that it was deliciously cool in that room, so Wendy and I sat in there and smoked whilst Richard prepared a nice salad for the three of us for lunch. I'd had an idea whilst we were out in the garden, and now seemed as good a time as any to put it to Wendy. When I'd explained what I wanted to do, she grinned and nodded approvingly. I went up to my bedroom to sort things out, and Wendy finished her cigar in peace.

Once lunch was over, Wendy excused herself.

"I need to speak to my agent," she said. "I won't be long, but I want to discuss my smoking in the film. I'm happy to stick with cigars, but I think pipe smoking might be a niche fetish that isn't touched on too often. It might mean more subscribers for Chuck, and he's motivated by making as much money as possible."

"I'll supervise Richard and get him ready to be milked," I smiled at my house guest. "His device will need to be cleaned and disinfected, and I'll shave his cock and balls. By the time you come back, he'll be all ready for you."

"That sounds perfect," Wendy smiled. "I shan't be long. I know Sidney plays golf on a Saturday afternoon. I need to catch him before he tees off!"

Half an hour or so later, Wendy joined Richard and me in the bathroom. His cock lock had been cleaned and disinfected to my satisfaction, and I was in the process of shaving him.

"Just in time!" I smiled as she came in. We were both still topless and I noticed that Wendy's nipples were beautifully hard. She must have enjoyed her conversation with her agent, I thought to myself.

"All done," Wendy announced. "Sidney was very impressed that I've smoked a cigar and a pipe already. He's going to phone Chuck tonight and ask him what he thinks I should smoke in the film. He'll give me a ring back sometime tomorrow. I gave him your landline number. I hope that's ok?"

"Not a problem at all. Can you hold his cock up for me please?" I replied. "Normally he holds his cock whilst I shave his balls, but it will be nice to have you hold it for him. Won't it cucky?"

"Oh, god, yes!" murmured Richard, and he sighed with contentment as Wendy knelt down on the floor beside me and took the hard cock between her forefinger and her thumb.

"Bloody hell, Richard!" she giggled, "no wonder Olwen became a Hot Wife! That cigar I smoked before lunch was longer and thicker than your cock!"

"I call it his little boy clit," I smiled. "It's hardly big enough to deserve to be called a cock!"

We both laughed and Richard blushed and squirmed in embarrassment.

I quickly shaved Richard's balls and wiped him off with a cold face flannel. He was beautifully smooth again, and ready to be milked.

"I've laid out your harness and your dildo in my bedroom," I informed Wendy. "He's ready to be pegged now. Let's all go into my bedroom, shall we?"

In the bedroom, as Wendy got into her harness, I strapped a leg spreader onto Richard's ankles and opened it wide. Then I bent him over the foot of the bed and cuffed his wrists to the the bolts in the frame. I stood back and surveyed my handiwork. He was spread eagled with his arse available and his little boi clit sticking out pathetically.

"Hmm! Not quite," I murmured to myself, and I went to my bedside cabinet and took out a condom from the box I kept in the drawer. I took it out of the wrapper and rolled it onto his erection.

"I don't want you wasting a drop!" I whispered into Richard's ear, and he grinned. He knew what would be required of him once he'd been milked.

I turned to Wendy, who seemed to be having some difficulty putting her dildo into the holder on her harness.

"Here. Let me," I offered, taking the dildo and slipping it into the holder quite easily. "Practice makes perfect!" I smiled, winking at her.

"Olwen, it's different to the one we used last night," she whispered. "It's ribbed. This won't hurt Richard will it?" she continued anxiously, still whispering.

"Not at all," I answered in a similar whisper. "He's used to being pegged with this one. Don't forget, you're going to stimulate his prostate so that you can drain his balls. It'll take some time, so don't tire yourself out by trying to peg him too quickly. Take your time and enjoy yourself."

Right, cucky," I said in my normal voice, "Wendy's strapped on and ready. I'm going to enjoy this."

I got onto the bed and sat with my back against the headboard. I peeled my skirt back and lay there with my legs open. Naturally I wasn't wearing any knickers, so Richard had a bird's eye view of my cunt. I stretched out my hand and retrieved the rabbit that stood on my bedside cabinet.

"You're not the only one who's going to cum this afternoon!" I grinned.

I winked at Wendy.

"Whenever you're ready, my dear," I smiled. "My cuckold is ready to be milked.

I watched intently as Wendy gripped her strap-on cock and lined it up against Richard's arsehole. Her face was a study in concentration. She shuffled forward a pace or two and Richard winced.

"The tip is in." She looked at me and smiled. "And you promise me that these ribs on the dildo aren't going to damage the cuckold?"

"Richard?" I said. "Answer Wendy."

"I've been pegged with this particular strap-on before," my cuckold confirmed. "It is certainly uncomfortable, but not as uncomfortable as having full and tender balls. Milking will ease the tenderness, so please, go ahead and peg me. Your cock won't damage me, I promise."

I winked at Wendy and began to rub myself with my rabbit. I'd never had the opportunity to pleasure myself whilst Richard was being milked before. I intended to make the most of this opportunity.

As I felt myself open up to accept my rabbit, 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.