Author's note: This is a stand alone story, but it includes characters first introduced in my serial "Training Wendy For Her New Role." It isn't necessary to have read this before starting on this story. It contains aspects of extreme sexual practices, including toilet and bodily functions, so if this doesn't float your boat, read no further. Like all authors, I appreciate comments, both complimentary and those of a constructive, critical type. Please consider using the star-rating system. Last of all, thank you for reading this. I hope you enjoy it.
It was about eight o'clock on a Thursday evening and Olwen Simpson had only just settled herself down on her cuckold's face when the phone rang. She was expecting her lover to ring as she had left a message on his answerphone informing him of a party at the local fetish club the following weekend. Warning her cuckold not to move, she got up and went to answer the phone.
"Surprise!" said a familiar voice when Olwen picked up the receiver. "How is my favourite mentor and Hot Wife?"
"Wendy!" replied Olwen, delightedly. "How lovely to hear from you. Are you back home now, or are you still making porn films in the States?"
"Both of those scenarios are true," giggled Wendy. "I'm back in London, but I'm here to make another film. That's why I'm phoning."
"Don't tell me," Olwen replied, "you're playing the part of a cigar smoking Hot Wife again. Or are you a pipe smoker in this one?"
"I smoke cigars," Wendy said, and Olwen thought that she detected a tinge of anxiety in her voice. She continued,
"Cigar smoking is my stock in trade in the adult film industry now. I've smoked in every film I've made, and it is very popular, or so I'm told. I'm playing the Madam in a brothel in this latest one," she said hesitatingly. "It's a very exclusive, very expensive club, and I provide girls who do all sorts of kink for very rich gentlemen, and some ladies too. The only problem is that the script says that I have to fall in love with one of my clients, and I break one of my own rules. I have sex with him."
"And...?" Olwen asked, intrigued by Wendy's explanation. "You didn't hold back when you were here last year. If I remember rightly, you took my strap on like a good 'un, and you strapped on and fucked me. You also pegged Richard, and you and I fucked the shit out of Jonathan and his friend Sebastian. And don't forget, you were fucked all ways when Richard and I came out to the States to see you make your first film."
"That's just what I'm phoning you to say," Wendy interrupted Olwen's flow. "I wasn't exactly fucked 'all ways'. I've never done anal, and this latest script says that the man I fall in love with loves anal."
Olwen laughed.
"Is that all?" she asked. "Get your gorgeous body down here, and I'll strap on and take your anal cherry in a flash," Olwen told her. "I loved having sex with you, and whilst I'd always prefer to fuck your cunt, I love giving and receiving anal. I was your mentor once. I can be your mentor again. You'll be able to take your fellow actor's cock up your shit chute no problem at all!"
"Oh thank you darling," Wendy sounded utterly relieved. "Are you busy this weekend? I really do need to get my arse fucked. Shooting starts on Monday, and in the adult entertainment industry, time is money!"
"You're in luck," Olwen informed her friend. "If you'd phoned at this time next week, I'd have had to turn you down. There's a sex party organised for a week on Saturday, and I'm taking my new lover, Chris, down to the club for a night of sucking and fucking. But I'm free this weekend. Chris is a fireman, and he's got the weekend shift this weekend, worst luck. And next week is our half term holiday," she added. "There'll be plenty of time and opportunity to get your arse fully prepared for some lovely hard cock!"
"Can I arrive tomorrow morning, then?" asked Wendy anxiously. "There's not all that much time. You might be on holiday, but as I said, we start shooting on Monday." Olwen detected a trace of real need in her voice.
"Of course you can come tomorrow," she replied. "I'll be in school of course, but I'll be home about four o'clock. I know Richard's in work tomorrow too, but I'll leave a front door key under the big flower pot by the front door. You can let yourself in and make yourself comfortable until I get there. Do you want me to leave a nice big butt plug out for you to wear until I get home. It'll open your arsehole up a bit, so taking my strap on won't be too much of a shock!"
Wendy giggled.
"That sounds perfect," she said. "I was dreading doing an anal scene, but now that I've talked to you, I feel much happier already. See you tomorrow, my darling. I can't wait for you to take my anal cherry!"
When Olwen got home from school the next afternoon, Wendy had arrived, and as she opened the front door, her friend and erstwhile lover rushed to meet her. They collided in the hallway and Wendy grabbed hold of Olwen and kissed her, shoving her tongue into Olwen's mouth and mashing her soft red lips against those of the surprised, but delighted school teacher.
When they both had to come up for air, Wendy gushed, "Oh, Olwen, my darling, I've missed you so much. Thank you so much for agreeing to mentor me again."
"Good afternoon to you too," Olwen smiled. "Now, first things first. A cup of tea, I think, then I'm going to strap on and fuck the shit out of your arse!"
"Not literally," she added quickly, seeing the look on Wendy's face. "I will be gentle, I promise. Come on into the kitchen. I'm gagging for a cuppa!"
"So," said Olwen conversationally as they both waited for the tea in the teapot to brew, "how are you getting on with the butt plug? Which one did you choose? I purposely left three different sizes out. I'll be very impressed if you got the biggest B-vibe inside you!"
Wendy blushed.
"Um... I think I have a problem," she replied. "I saw the three you'd left out for me, and I thought that I'd work my way up, sizewise, so I started with the smallest one."
"Very sensible," Olwen said approvingly. "Everyone has to start somewhere. I know the smallest size is barely thicker than a finger, but if you've never had a butt plug up your arse..."
"I couldn't take it," Wendy said, her bottom lip trembling with emotion. "I didn't mind the stinging sensation. That was quite nice. It's just that I couldn't get it up at all. The tip went in, but then, try as I might, it wouldn't go any further."
All thoughts of tea were forgotten, and Olwen led Wendy upstairs to her bedroom. The three differently sized butt plugs were still on her bed where she had placed them before leaving for school that morning.
Olwen picked up the smallest plug and lathered it in lube.
"Bend over and pull your arse cheeks apart," she said sternly, and Wendy did as she was told. She shivered as she felt the tip of the plug push against her pucker.
"I won't shove it in," Olwen said gently, "but I am going to put some pressure on until it goes all the way in. Don't forget to breathe. If you hold your breath, you'll tense up, and that really will hurt."
Once more, Wendy did as she was told. Holding her arse cheeks apart, she whimpered as the tip of the butt plug penetrated her virgin arsehole.
Olwen pushed gently, but met stern resistance.