Cheese, Chalk and Plenty of Pork – Part 08 of 10

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Cheese, Chalk and Plenty of Pork – Part 08 of 10
by Lin Dale

Synopsis: When Greta meets Gavin at her rich father’s second wedding, she immediately falls in love. But, just like cheese and chalk, he is a beautiful, slim young man and she is heavily obese; she needs to find some way to stop him wandering off. Her father’s new wife has problems facing up to her role as a Lady, so she decides to involve Gavin in a project with certain challenges.

Author’s Note: This story is complete and in ten parts which will be released at approximately daily intervals. It contains items such as crossdressing, non-explicit sex between adults and language typical of that between English adults. If you feel this may offend you, then please do not read.

Part 8 – In which Gavin Gets to Ride Side-Saddle

As Michelle looked back on that previous evening, he was uncertain about everything. His upbringing told him that it was very wrong but it had certainly been an experience outside anything he could have imagined and which, if he was honest, he’d enjoyed. It had actually been fun putting himself in the role of the female being screwed by a male. Greta had instructed him on how to behave when on the receiving end of a penis, and how to fake an orgasm. Hell! The things women had to do! What fun!

But he hadn’t time to think of last night. Greta would be here at any moment with Chelle just before his first lesson in riding side-saddle was due to begin at the stables. They’d agreed that, in order that Chelle was not found to be in two places at the same time, she would come to the crofter’s cottage and stay there whilst Michelle went on the riding lesson. When he returned to the cottage, she would then go back to the house. They could do the same when he was going on the hunt.

It all worked out quite well. Chelle arrived dressed in jodhpurs and matching jacket, with sexy leather riding boots. She promptly removed them all, revealing underwear far sexier than the plain stuff that Michelle was wearing. Neither he nor Greta commented, and he put on the clothes that she had just taken off whilst she put on a flimsy house gown. His makeup had already been done, so within a few minutes, Greta and Chelle exited the house and walked to the stables, except, of course, it was not the real Chelle but Michelle wearing her clothes.

“Did you notice her underwear?” Greta hissed as soon as they had left the cottage.

“Was it anything special?” Michelle replied, trying to appear nonchalant.

“Don’t be stupid. I saw your eyes goggling over her. She was obviously trying to pull you. I mean, who would wear stockings and suspenders beneath jodhpurs?”

It was a question that Michelle had also been wondering, but Chelle knew that he was locked up and Greta had the key.

“I guess she’s just trying to tease me,” he suggested.

“But why would she do that?” Greta asked. “She needs to keep you onside. Did you see that negligee she put on? It’ll be no good for standing about in the crofter’s cottage, which is cold at the best of times.”

“Like I say, she’s trying to frustrate me,” he said. “I’m not certain why but knowing her, it’s probably just for the hell of it.”

It was a relatively short walk to the stables since they were right next to the entrance which they’d come through just four days before. Sandra, the owner of the stables, was being assisted by a couple of teenage girls, Olivia and Chloe, all of whom Michelle would loved to have got to know without the restrictions of his Y-gina, but knew that such thoughts were simply frustrating. Instead, he focussed upon being a willing and competent student in the art of riding side-saddle.

It was good to get back in the saddle, even if in such an unusual way, and he quickly picked up the basic skills. Sandra was particularly pleased with her new student, and expressed surprise that it had taken Chelle so long to come to the stables, when she obviously enjoyed it so much. She told him they would practice jumping on their next lesson, which he really looked forward to.

Two hours later, he and Greta walked back to the crofter’s cottage, where Chelle awaited them. She was in one of her brighter moods, and she delighted with the success of Michelle’s lesson. Michelle was secretly hoping that she had somehow discovered the key to his Y-gina and would send Greta away on some pretext so she could shag him, but nothing like that occurred. Within a few minutes, they had reversed their clothing and Greta and Chelle walked back to the house, with Greta promising she would be back later to attend to his needs.

It was the following day that Chelle reminded them that the next hunt meeting was in only two weeks’ time and they had to prepare.

“I think the first side-saddle lesson went really well,” Michelle responded, "and I’ve got four more lessons booked before then. What else do we need to do?”

Chelle looked at him in amazement. “You have to ride in Victorian dress, of course. We have to dress you.”

He’d forgotten all about that. “Oh. Oh, yes. I suppose you do. Is it difficult?”

Chelle sighed with exasperation. “No female would say such a thing. If you were simply dressing for a modern-day occasion, you’d be thinking about it now. You have to dress as a Victorian riding lady.”

“Does that mean what I think it means?” Michelle asked.

“Which is?”

“A…” He plucked up courage. “A corset?”

“Abso-bloody-lutely,” Greta butted in. “And they are absolute-bloody-murder.”

“They’re not murder,” Chelle corrected. “They are simply figure enhancing. And a riding corset has a lot more flexibility than a conventional corset to the period, so there’s definitely nothing to worry about.”

Michelle looked unconvinced.

“I’ll bring some clobber over this afternoon, and we can get started,” she said with rather a wicked smile.

She brought a suitcase full of stuff so Greta drove her to the crofter’s cottage in her Land Rover.

“I don’t want clothes for a week,” Gavin protested. “It’s only a single use.”

“Victorian ladies had huge trunks for their apparel,” Chelle said. “They also had lady’s maids, whereas you’re going to have to get used to putting on this gear by yourself. Have you taken a shower, as I asked? We want to avoid having to wash this lot too often if we can.”

Gavin confirmed he’d had a shower so he was told to strip off and put on his padded pants and breasts. When they had been delivered, Greta had carefully cut an opening in the groin so his Y-gina could show through. It also conveniently meant he could have a wee without pulling them down.

“Right,” Chelle said. “Let’s start with drawers and chemise.”

Although he’d heard the word drawers used before, he never realised where the term came from until he saw the garment Chelle produced from her suitcase. It was essentially two cotton tubes of material, with a wide hem around the tops. A lace was threaded through part of the hems of the two tubes. He had to pull the tubes up his legs, and then tie the lace in a bow around his waist. The two tubes were normally drawn together, like drawing curtains, at the waist and groin. Should he need to go to the toilet, he could simply draw the top of the tubes apart and squat down. It also meant, Greta pointed out, that should a man want to shag the woman, he could simply draw the two halves apart and do so. No inconvenient need to pull down panties.

Next came the stockings with ribbon garters which again had to be tied with a bow, followed by the garment he had been dreading.

“For heaven’s sake,” Chelle said. “It’s only a garment.”

“A garment of torture,” Greta added.

“No, it’s not,” Chelle said. “A corset is simply a device to make you look more shapely. Now, come here, Michelle, and let’s put it on you.”

Reluctantly, he did so, and as Chelle started to draw in the laces, he was pleasantly surprised that not only was it not painful, but it made a startling difference to his waistline.

“Wow!” he said, as he admired himself in the mirror.

“Exactly,” Chelle said. “Now, the trousers.”

“Trousers!” Michelle was surprised. “I thought I’d be wearing a skirt. Surely, Victorian women didn’t wear trousers.”

“For riding,” Chelle said, “they’d be wearing trousers beneath their skirt. Can you imaging trying to grip the pommel of your saddle only wearing stockings?”

It was a valid point and Michelle pulled them up her legs and fastened them. Afterwards, he put on the boots and spent ages buttoning them up.

Then, it was time for the blouse, with many, many buttons each of which he had to fiddle with, followed by the voluminous skirt, which he stepped into. There was a bodice with intricate military style braiding and, again, many buttons which were even more fiddly than the blouse. A cleverly designed modern safety helmet disguised as a top hat completed his dressing.

“Wow, Michelle,” Greta said. “You look absolutely brill.”

“Victorian ladies,” Michelle said, in Chelle’s shrill voice, “may be described as charming, distinguished or even respectable. They are certainly not brill.”

Both women had to admit that Gavin had turned into a very presentable Lady Michelle.

Of course, afterwards, he had to take it all off, and hang it up in preparation for the hunt.


The next two weeks was much of the same. Michelle went for a few more side-saddle lessons at the stables dressed as Chelle, whilst Greta continued to abundantly provide his sexual needs, as both male and female. As time progressed, he realised he was becoming used to her rather plentiful flesh and cheerful smiles, and also her continual willingness to have sex whenever he wished.

Then, all too soon, it was time to go on the hunt, pretending to be Michelle not just to a couple of stable girls who had never spoken to the real Michelle, but to half the county who had known her as she and Carver had become an item, not to say, to her husband who had lived with her for a few months.

Michelle and Greta arrived in plenty of time. Getting dressed in his Victorian riding attire went smoothly, and then he was walking with Greta onto the stables in order to get mounted.

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Wendy Jean's picture

Is making with unwilling female, but seem to be pretty good at it.