Training Wendy For Her New Role Ch. 02 – Celebrities & Fan Fiction

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. The script requires Wendy to portray a Hot Wife who smokes cigars and loves to cuckold her husband. In order to get first hand experience of such a lifestyle, Wendy is staying at the remote home of Olwen and her cuckold Richard.

Wendy squeezed my hand.

“I’m so looking forward to this,” she said excitedly. “I’m fed up playing bloody middle class housewives who keep the home tidy, volunteer to help good causes, and only have sex on Friday nights with the light off and in the missionary position, I can’t wait to become a Hot Wife!”

“You and I are going to get on very well, I think,” I said, helping her off with her overcoat. I deliberately brushed her tit with my hand, and she smiled.

“You’re bi, aren’t you?” she said. “There’s lots of lesbians and bi-sexual women in my business. I’ve never kissed a wom…”

I kissed her full on the mouth, and shoved my tongue between her teeth. She resisted for about three seconds, then opened her mouth and we tongue wrestled. When the kiss was broken, her eyes were sparkling, and she was breathing heavily.

“Oh my!” she said with a grin, “that was wonderful! You taste so exotic! I’m going to enjoy being taught by you.”

I led her into the middle room, and we sat down side by side on the settee.

“You seem very overdressed,” I smiled. “Shall we begin our lessons right away? Richard will be back with the tea in a minute. Let’s get our tits out and begin teasing him.”

Wendy grinned and started to unbutton her blouse.

“I’m really going to enjoy this training!” she said breathlessly. “Can we kiss some more in front of him?”

“Kiss, and a lot more besides,” I winked at her. She wasn’t the only one who was gonna enjoy this experience! Richard and I were gonna have a ball too!


Richard brought the tea in on a tray. I knew from his reaction that the sight that greeted him had caused his cock lock to become even more ‘snug’. Wendy was sitting on my lap, and we were playing with each other’s nipples. He stood respectfully in the doorway and waited to be invited in. Eventually I relented.

“Ah, tea,” I said, tweaking Wendy’s nipple playfully. “Bring it in, cucky. We have much to discuss. Wendy’s eager to learn the art of Hot Wifery!”

“I had no idea that couples like you existed,” Wendy admitted a few moments later, as she sipped her tea. “I really want to succeed in this role, but if I’m honest, I have been dreading this period where I am supposed to learn about becoming a Hot Wife. But look at me! Within ten minutes of arriving, I’ve been kissed by another woman, and really enjoyed it. And now, I’m sitting next to her, with my tits out, discussing the implications of having sex with men other than my husband!”

“Not only men!” I reminded her. “We’ll be sleeping together during your stay here. Chuck, your director made it perfectly clear that you need to learn how to use a strap-on. He wants you to be bi-sexual in the film, and the type of Hot Wife who pegs her cuckold!”

Wendy grinned and hugged herself.

“Bring it on!” she smiled. “My real life husband is used to me disappearing for weeks at a time to film. When I get home, he’s going to have a hell of a shock when I tell him what I’ve been doing!”

“Well one thing is very important,” I replied, putting my empty cup down, and reaching out to take Wendy’s hand. “I know a few couples who live the same sort of lifestyle as Richard and I. But being a Hot Wife doesn’t mean that everyone does exactly the same thing. Yes, we all fuck men other than our husbands. But some of my friends come back home after a date, and their cuckolds reclaim them.”

I saw Wendy’s look of incomprehension.

“That means that they have sex with their cuckolds, so that he can ‘reclaim’ his position in the marriage,” I explained. “Richard and I used to do that, didn’t we, dear?”

Richard smiled, glad to be brought into the conversation.

“Yes, we did, for a while,” he confirmed. “My problem was that I could never give Olwen the pleasure I wanted her to have when she’s being fucked.”

Wendy giggled.

“I love how you are both so open about what you get up to,” she admitted. “Can you tell me why you felt like that, or is it personal?”

Richard smiled.

“Of course I can tell you,” he said. “Olwen has already mentioned that we no longer have penetrative sex. That was a mutual decision. Everything we do in this lifestyle is consensual.”

He stood up.

“May I?” he asked me and I nodded, reaching for the discrete ankle chain that I wore everywhere.

Richard undid the ties of his frilly apron, and removed it. He stood proudly in front of Wendy, who put her hand to her mouth, as her eyes widened at the sight that greeted her.

“Oh my!” she said, softly. “I’ve heard about such things, but I’ve never, ever seen one being worn!”

She was, of course, referring to Richard’s cock lock, which was now fully on display. I removed the key from my ankle bracelet and handed it to Wendy.

“Unlock him,” I smiled. “Then you’ll be able to see why I don’t let him in me any more. Go ahead,” I continued, sensing her reluctance. “You’re going to have to learn how to put one of these things on whoever it is who is going to play the part of your cuckold in the film!”

Wendy took the key. It slid into the small padlock that kept Richard’s device in place, and there was a soft click as she turned it. She looked at me.

“Take the padlock out of that hasp,” I said, “and then slide the sheath off his cock.”

Wendy did as she was told, and, as usual, as soon as he was released, Richard started to get a hard on.

“Now take the locking ring off his balls,” I said. “It’s held it place by that… Ah! There you go! Now take those two bits off him, and voila! He’s unlocked!”

Wendy looked at Richard and blushed.

“I hope I didn’t hurt you?” she asked in a concerned voice. “This bit here,” She held up the locking ring. “It seemed awfully tight around your balls!”

Richard shook his head.

“It didn’t hurt at all,” he admitted. “But yes, it is tight. Olwen keeps me locked permanently, although I am released once a week, when I am milked.”

Wendy’s pretty face creased into a frown.

“Milked?” she repeated. “Whatever does that mean?”

“Bend over, cucky,” I said. “It’s inspection time!”

Wendy blushed again as Richard turned round and gripped his ankles. For a man of his age, he’s remarkably flexible, and he had no issue in ‘assuming the position’ as we like to call it. His legs were straight, and his arse perfectly displayed for what I was about to do. I pulled his bum cheeks aside, revealing his most intimate of orifices.

“Every Saturday, I drain his balls,” I explained. “Some Hot Wives use their hand to give their cuckold a wank. Some even suck them off till they cum. I prefer to use prostate massage.”

I smiled at Wendy’s look of incomprehension.

“Men have a prostate gland that is situated in the groin, behind their cock and in front of their rectum,” I began. “It can be reached by sticking a finger up the arse.”

I grinned at Wendy’s look of horror.

“Don’t worry,” I continued, “Richard knows the importance of wiping thoroughly! When I touch his prostate, it makes his cock twitch. Watch!”

I slid my finger up Richard’s arse and after years of practise, immediately located his prostate. I stroked it a few times and Richard’s little cock did indeed twitch. I pulled my finger out and looked at Wendy.

“Milking day is tomorrow,” I informed her. “We’ll do it together, ok? I don’t know if milking is in your script, but I’m betting that Chuck will love to see you doing it on camera!”

I gave Richard a sharp slap on the arse, and he stood up. His cock was fully hard, and leaking pre cum. I nodded at it.

“That’s why he doesn’t get to fuck me any more,” I said. “Look at it! Three inches at best, and he’s already leaking!”

Wendy giggled again.

“My Jack is a lot bigger than that,” she admitted. “But his is the only… um… cock I’ve ever had!”

I winked at her.

“Don’t worry,” I assured her. “Everything is in hand! We’re all going down to our special club tomorrow night. You and I are going to pick up a couple of men, and we’re going to get ourselves fucked!”

Wendy nodded enthusiastically.

“My agent told me that I would be getting that sort of experience,” she admitted. “I’ve been on the pill for a month or so now, so I won’t need to use condoms. And I’ve brought a couple of props with me as well. I know that I’m not in the Brigitte Bardoe class, but I do sometimes get recognised. So if you don’t mind, I’ll wear my wig and a pair of plain lensed glasses when we go to the club?”

That’s up to you,” I replied. “It’s a fetish club, so everyone is a member, and we’re all very discrete, I assure you. Members can bring guests, but they are expected to keep what they see and do to themselves.”

“In that case,” Wendy said, “I’ll do whatever you advise. I’m in your hands, Olwen.”

“Yes you are!” I thought as I smiled and winked at her. “And very soon you’re gonna be between my legs. I want to teach you to eat my cunt!”

“Let’s get you settled in, shall we?” I said, getting to my feet. “Richard, bring Wendy’s case up to my bedroom.”

I took her hand and led Wendy upstairs. Richard followed. When we got into my bedroom, Wendy looked at me in surprise.

“I’m sleeping in here?” she asked.

I leaned in and kissed her again.

“You are indeed,” I confirmed, “although how much sleep we’ll get is up to you! I’ve been asked by your agent and your producer to introduce you to the pleasures of sapphic loving. I’d like to get started right away!”

Wendy smiled uncertainly.

“I’m a total novice,” she admitted. “A lesbian virgin, if you like. I’ve only ever had sex with Jack, my husband. You will be gentle with me, won’t you?”

“Of course, my dear, ” I lied. “Remember what I said about only playing consensually? That is the only rule in this house. Now, come on, I’ve seen your lovely tits. Let’s get ourselves naked and see how much fun being a Hot Wife is!”

In no time at all, Wendy and I were in each other’s arms on my big double bed. Richard was seated in his cuckold chair, eagerly watching as we kissed and cuddled.

“I want you to copy everything I do,” I told her, “and don’t worry. This is gonna be fun!”

I started on Wendy’s tits, tweaking one nipple whilst I suckled the other. As Wendy mirrored all my actions, I felt myself starting to get wet. Abandoning her tits for the moment, I kissed her again, and slid a finger into her cunt. She wasn’t even damp yet!

I opened my legs to give Wendy access, and when her finger went in, I felt her stiffen.

“Don’t worry,” I whispered into her mouth, “I’ll soon have you nice and wet too. Let’s move a bit so that we can rub our cunts together.”

There was a bit of shuffling around, and I showed Wendy how to scissor. Our cunts met, kissed, and I began to grind mine against hers. Wendy murmured with pleasure.

“Mmm! That feels good!” she gasped. “Is this you fucking me?”

“Not yet,” I admitted, rubbing my cunt frantically against Wendy’s. “Cucky,” I gasped, “get my double headed dildo from the drawer, will you?”

Richard got up from his seat and rummaged around in the bedside chest of drawers. He handed me one of my favourite toys, and I pulled away from Wendy, who gave a little mew of disappointment.

“Hang on,” I smiled, sliding one end of the dildo into my sopping wet cunt. I moved back towards her and she grinned in comprehension as I lined up the other end at her cunt entrance.

“Oh my!” she giggled, “What a big cock you have!”

“All the better to fuck you with!” I said softly, sliding into her.

“Yes!” crowed Wendy. “Oh, yes! Fuck me, Olwen! Give me your lovely big cock!”

For a novice, Wendy certainly knew all the moves. We quickly got into a rhythm and I soon found myself on the edge of a mind-blowing orgasm. I don’t always squirt, but when I do, it’s like a river bursting its banks. This was one of those occasions, and Wendy must have had a hell of a shock as I drenched her with a spray of cunt cum.

It was enough to set her off, and she moaned and howled as her own orgasm took over and she writhed about taking all of my big rubber cock into her cunt and trying in vain to clamp down on it. Not for the first time, I was grateful for the fact that we have no neighbours. Wendy was like a wailing banshee! We stopped fucking, and lay panting, still joined by the double headed dildo.

Eventually Wendy reached down and, holding the dildo in one hand, extracted herself off it. She came and lay down beside me and kissed me.

“Thank you,” she whispered into my mouth. “That was intense. I never realised how hard I would cum being fucked by a dildo. It was wonderful.”

“It’s not over yet,” I smiled. “Get on your back!”

Wordlessly, Wendy obeyed, and Richard came over and stood by the side of the bed.

“Guests first,” I winked at him, and he clambered onto the bed and lowered his face into the gap between Wendy’s legs.

“What the…?” she gasped and I leaned over and kissed her.

“Shhh!” I admonished her. “It’s clean up time. Lie back and enjoy it! I’ll be back in two ticks.”

As I got out of bed, I heard the familiar sound of my cuckold lapping away at a freshly fucked cunt, and I smiled to myself.

“My turn next,” I thought to myself as I went downstairs.

Back in my bedroom a few minutes later, I saw Wendy tugging at her nipples as Richard licked and sucked at her cunt. Her eyes were closed and her mouth open. I slid back into bed and leaned over and kissed her.

She slid her tongue into my mouth and I sucked hard on it. Then I broke off the kiss and took a puff on the cigar that I had gone downstairs to fetch. I blew my smoke into her mouth, and she opened her eyes and looked quizzically at me.

“Oh! You’re smoking!” she said softly. “I thought why you tasted differently.”

“It’s a cliché,I know,” I admitted, “but I love to smoke after sex.”

I puffed on my cigar again, and offered it to Wendy.

“Go ahead,” I said. “You’re supposed to be a cigar smoking Hot Wife in this film. Have a puff. Don’t pull on it too hard at first. Just suck and then blow out your smoke.”

Wendy took the cigar tentatively, and put it in her mouth. Her lips curled around the butt end and she sucked on it gently. The lit end glowed, and she took the cigar out of her mouth and exhaled, coughing gently.

“It tastes alright,” she admitted, taking another puff. “I could get used to this! Oh my word! I haven’t been here but a couple of hours and already I’ve been fucked and now I’m smoking!”

I grinned at her and took my cigar back.

“Have you finished with my cuckold?” I asked cheekily. “My cunt needs a good clean up too!”

Wendy giggled and patted Richard on the head.

“You heard your Hot Wife, cucky,” she said softly. “Thank you for cleaning me up. It’s Olwen’s turn now!”

I handed Wendy the slick double headed dildo that we’d used to fuck one another. The end that had been inside me glistened with my cunt cream. I winked at her.

“Waste not, want not!” I smiled, and Wendy understood immediately. She stuck her tongue out and licked the tip of the dildo. A string of thick cunt cream attached itself to her tongue and she giggled.

“Nice?” I asked as Richard went down on me and I automatically clamped my thighs round his head. I shuddered as I felt his tongue slip into my cunt.

I puffed on my cigar and Wendy put the dildo into her mouth, and pretended to smoke it. We giggled like naughty schoolgirls, and held hands like sated lovers.

Saturday morning dawned, and I was awakened by having my nipple suckled. I opened my eyes to find Wendy attached to my tit.

“Good morning!” I mumbled, only to receive a “mmm mmmmmm” in reply. I pulled Wendy up off my tit and kissed her.

“What a lovely way to be woken up,” I smiled. “Did you enjoy last night?”

“It was probably the best night of my life,” she replied shyly. “I never realised that sex with another woman could be so exciting. I don’t think I’ve ever cum so hard in my life!”

“We could go again if you like,” I suggested. “Early morning sex is one of my favourite pastimes!”

Wendy blushed. “I’m not ready,” she protested.

“Don’t worry about that,” I consoled her. reaching between her legs and rubbing my index finger along her cunt slit. “Olwen’s magic fingers will soon have you nice and wet!”

I slid my index finger into her cunt and twiddled it around, searching for her clit. Wendy seemed to be holding her breath, but when my inquisitive finger found its target, she gave an ‘Aahh!’ of pleasure. I could feel her juices starting to flow.

There was a gentle knock on the bedroom door. I shouted “Come in!”, and Richard appeared. He’d been sent to the spare room last night after he’d finished cleaning Wendy and me up.

“Good morning, ladies,” Richard began politely. “May I bring you a cup of tea each in bed, or would you prefer to have some privacy?”

I looked at Wendy, who was beginning to glow, thanks to my magic finger.

“Tea?” I asked and she nodded wordlessly, frantically clamping around my finger. She was enjoying herself!

“Tea for two it is then,” I said to my cuckold. “Bring my harness and strap on too, please Richard. Wendy has a lot to learn!”

Whilst we waited for our tea to cool, I showed Wendy how to wear a strap on harness. When I slid the dildo into place, she blushed and giggled.

“Look at me!” she said shyly. “Can you take a photo of me and my cock? This is a moment I really don’t want to forget!”

I snapped a few shots of Wendy flaunting her rubber cock on my mobile, and then I lay back on the bed and opened my legs.

“I’m ready,” I told her. “Come on, Wendy. Fuck me!”

It was obvious that she’d never done anything like this before. She got between my legs alright, but she didn’t realise that she had to line her dildo up properly. Her first thrust ended up with the dildo between my arse cheeks.

I grinned at her.

“How did you know I love anal too?” I asked, and Wendy collapsed onto my tits in gales of laughter.

When we’d both recovered, I helped Wendy to put the dildo in the correct position. She looked me straight in the eye and I whispered, “Ease your hips forward slowly.”

Wendy did as she was told, and I felt the tip of the dildo open me up and nestle snugly inside my cunt.

“You’re in,” I smiled. “Now take your time. Slide all the way in and take it easy. Set a nice steady rhythm.”

“I’m not hurting you, am I?” Wendy asked anxiously.

“Far from it!” I assured her. “I love being dildo fucked almost as much I love being cock fucked. It’s just that until you’ve got used to having a cock, albeit a rubber one, it’s all too easy to go at it too frantically, and slip out, which is frustrating for both of us.”

Wendy eased herself into me, lowering her hips slowly. When our two pairs of tits rested against each other, she dipped her head and kissed me.

“Good girl,” I murmured into her mouth and then we were off.

She pulled back a little and then went back in deep. Next time, she pulled out a little further before sliding back into me. She was bloody good at this! I’d never have guessed that she’d never strapped on before! I wrapped my legs around her and pulled her in deeper still. We kissed again, and Wendy started to fuck me properly.

I was still glowing as we both went downstairs for breakfast. Wendy was as proud as Punch that she’d managed to make me squirt, and our first meal of the day was a riotous affair, with lots of laughter and blushing as I told Richard what an excellent cockswoman Wendy had proved to be on her first attempt at strap on fucking.

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