In this 3rd part of a piece of fiction dedicated to the beautiful and beguiling Dilan, Richard returns, at her beckoning, to allow her to practice her caning technique. Richard ends up getting a little more than he bargained for as he is made to earn his stripes…
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Weeks had passed, without word from Dilan and then, on a Sunday evening, as Richard began to find his comfortable spot on the sofa, his phone rang.
“Hello Richard, how are you?” Dilan’s sweet voice chimed. “Playing with yourself I’ll bet. Bored little sissy, playing with herself!” She laughed.
“Actually, I was just about to watch TV.” He argued.
“Well if you are that bored, I have a little job for my sissy maid!” She barked.
Richard paused, not knowing what to say. Already, he found himself feeling excited, aroused even.
“I’m getting myself ready to deal with little wimps like you more often and I think my sissy maid would make a very good target as I practice my caning technique, don’t you?”
Richard swallowed hard. “Yesss Dilan, yesss of course”.
“Its Mistress Honeysuckle to you, cheeky sissy girl,” she replied. “Well, pack your girly things and get yourself here six thirty this evening.”
“Yes, of course Mistress, of course,” he gabbled.
At six thirty, sharp, Richard was at Dilan’s door again. He remembered his last visit; the humiliation and the pain but here he was, again, awaiting her whim.
From the crack in the door, Dilan’s sweet face appeared. She smiled, softly before her expression shifted to one of stern determination. “Come in,” she murmured, opening the door wider.
Dilan was looking very different than Richard had pleasured himself remembering from his last visit. Forgoing the school girl look, today she reminded him of a on office manager he had once feared. Her soft blonde hair was tied up in bun and she was dressed in a short, grey pencil skirt, a crisp white blouse, black stockings and patent leather court shoes completed the authoritarian look.
Richard tried his best not to stare as he made his way into the hall. None of the punishment or humiliation he had experienced on his last visit had diminished his longing for Dilan. Not only was Dilan sweetly attractive, she was intelligent, sensitive and so aware of how to push his submissive tendencies towards their limits.
Dilan stood in his path. She stood in his way, arms crossed and feet firmly planted on the carpeted floor.
“So Richard, as soon as you are dressed appropriately, you will be Becky and I expect complete obedience. Do you understand?” She demanded.
“Yes Miss Honeysuckle,” he confirmed.
Pointing toward the stairs, her stare caught his downturned eyes. “You know where the bedroom is. Go and get changed. Go on!”
Dilan turned her back on him and returned the lounge where Richard had last faced her cane. On the sofa, Alex, her burly camera man friend had made himself quite comfortable.
“How is our little sissy friend?” He laughed.
“Now don’t make fun Alex. He’s here to help! I need to crack this caning thing If I’m going to make something of Miss Honeysuckle. I have had a thought though. How about we test Becky’s oral skills? We could make something out of the whole forced bi scene couldn’t we”?
Shifting in his seat, Alex began ro harden in his trousers. “Dilan, you cheeky minx! Mmm, sissy lips around my cock. Now you are talking!” He laughed.
Tapping down the stairs, Richard’s heels alerted them to his return and they both cleared their throats, as if they had been discussing something inappropriate and off limits.
“Oh Becky, aren’t you a picture, don’t you think Angus. Isn’t she cute?” She chuckled.
Richard froze, teetering on ridiculously high heels, dressed as a fetish French Maid in a waist clinching, tutu skirted black and white satin dress. His black stocking legs trembled as he realised that, again, he was being seen by a man as well as the delicious, Dilan.
“She is rather sweet isn’t she Dilan? I’m sure she will be of the utmost service this evening,” he said.
From the sofa, the man stood. He was everything Richard could never be; masculine, strong and handsome. Richard wasn’t attracted to men in any way but he admired this mans physical presence and his commanding authority.
“Now then Becky, I think it’s time we began. I need you bent over the poof,” Dilan ordered.
Shuffling forward in his sweet, shiny black dress, his face framed in a shoulder length black wig, Richard wasted no time in complying.
“Good gurl”, Dilan giggled, as sissy Becky stretched her upturned rump across the poof. Quite naturally, his skirt lifted, revealing a sweet pair of ruffle backed, white panties, as he stretched his legs to mount the poof. “Now then Becky, let’s see about thrashing that delicious bottom of yours.
Dilan admired his pretty, quite feminine bottom for just as while as she contemplated his position and her approach to the punishment that he would be made to take.
“I’ll have the senior cane pleas Alex,” she asked, turning for a moment to smile at her accomplice.
From a tall, earthenware vase in the corner of the room, Alex took a crooked handled, long, thick cane. Dilan opened her hand and winked at Alex. “Don’t even think about it!” She laughed. Resisting the urge to give her hand a tap, Alex, instead, ran the cane behind her beautiful, tightly clad bottom. Dilan sighed, longingly, as she thought about being in Becky’s shoes, being dragged across the poof, having her knickers tugged down by Alex’s strong hands and being punished.
Dilan grabbed the cane from Alex’s hands and positioned herself to the side of Richard’s upturned bottom.
“Now are you ready my little caning Maid?” She asked.
“Yes Miss Honeysuckle,” he dutifully replied.
“Good! I’m going to give you 24 strokes In 4 batches of six. Of course, I will be expecting you to count them and thank me,” Dilan demanded.
“Yes Mistress,” he whimpered.
“Good gurl,” she replied.
Dilan flexed the cane between her hands, testing its flexibility and then gave it a few test strokes, through the air. The whoosh of the wood, passing at speed through the air whistled through Richards ears. He gritted his teeth and clenched his bottom cheeks as he imagined what he might feel when it landed on his pantie clad behind. He knew too, that those panties would soon be yanked down to uncover his cheeks and his heavy balls.
Dilan had expelled every ounce of her strength as she landed her first strike. The cane landed neatly across the centre of Richards white cheeks. As the cane was retrieved from his skin, a broad red line immediately began to swell from his cheeks. Dilan was delighted with her first mark and smiled as she waited for Richard’s words.
“One thank you Miss,” he gasped, grasping the base of the poof, his hands clenching as the first wave of pain hit his heightened, dizzy senses. To be here, humiliated, as a sissy in-front of this beautiful young woman, demeaned by someone he admired and adored, gave him such a huge submissive thrill.
“Good girl,” she cooed before again lifting the cane high above her pretty head. Dilan sized up her target. It was such a pretty, feminine bottom that it begged to be coloured and striped and practicing her technique on poor sissy becky, was such a pleasure.
Whoosh, crack…. “oww,” yelled Richard. A second broad stripe appeared just a centimetre above the first. As it began to swell, it broadened, almost to meet the first.
“Two thank you Miss,” Richard replied.
Alex shifted from the Sofa. He had found himself becoming quite aroused by what he was seeing. Stirring in his pants, something warm, hardening and ready for some attention made him rise to his feet.
Dilan turned and caught sight of the bulge developing in his jeans.
“Something tells me your enjoying this Alex!” She chuckled as she cupped the bulge with her tender fingers. “Oh yes, I think we might have to get our sissy to attend to that, don’t you Alex?”
“Mmm, well yes, why not? She does need to develop some oral skills if she is to be of use to your little meets with subs, doesn’t she?” He said.
Unzipping his fly, Alex moved to stand in front of Richard’s down turned head. He stood with his enormous cock in his hands as Dilan stood, mesmerised, cane frozen in mid air, to the side of Richards bare, stripped bottom.
Regaining her composure, Dilan returned to the job in hand. She needed to focus on her technique and there was a sissy bottom waiting to be punished.
Strokes three and four were harder still, till by the fifth and sixth, poor Richard could barely contain himself. His body twitching and flinching with each painful impact of the wickedly heavy, flexing cane.
As he thanked her for the last of the first set, he became aware of something close to his cheek, something hard, warm and sticky brushed against his skin. A familiar smell, a male, sexual smell hit his nose.
“Fuck no… he cried,” realising that the offending object was Alex’s hard, throbbing cock.
“I beg your pardon young lady?” Dilan remarked. “You had better think a little bit harder before swearing! Think yourself lucky! Alex has a lovely cock and a gurl like you will just love having it in your pretty mouth, won’t you!” She demanded.
“If you say so Miss Honeysuckle,” Richard reluctantly complied.
“Well, before I add to your stripes, you had better earn them! Let’s see what you can do with those dirty sissy lips of yours.”
Alex grabbed Becky’s chin and lifted it. Staring into his wide, fearful eyes, under the silly wig on his head, Alex pushed his cock towards her painted red lips.
Richard, reluctantly, opened his mouth and felt the warm, salty flesh of Alex’s meaty cock slide over his lips and tongue. The bulging head of Alex’s cock was leaking pre cum and Richard enjoyed, just for a moment, a taste he had enjoyed many times from his own cock. The enjoyment was short lived, as Alex began to fuck his mouth with thrusts of his cock reaching the back of Richard’s throats, making him gag, making his eyes water.
“Suck you little tart, suck and make me cum, don’t keep my waiting slut,” he hissed.
Dilan stood with her arms crossed, as Alex fucked Richards mouth. It occurred to her that this sort of thing would make some of her film clip audience quite hungry for more.
Alex was beginning to groan as sissy becky found her pace. Richard had begun find the humiliation as exciting as the predicament of being in this silly maid uniform, being thrashed by Miss Honeysuckle. He found himself meeting Alex’s thrusts with the pace of his own head, as his head bobbed up and down, his red lips sliding over Alex’s drool covered dick.
“Aghhhhhh! Fuck…..” Alex froze as his cock exploded, releasing huge goblets of warm cum onto the silly sissies tongue. Richard gasped and coughed as the hot jizz filled his mouth. Drops of cum were leaking from around the plug of Alex’s cock and out of becky’s ridiculously red lips.
“Good gurl…” cooed Dilan, “You’ve made Alex cum! Now we had better give you the rest of those stripes you have earn’t.”
Alex withdrew his cock from Richard’s leaking mouth. “Swallow slut,” he groaned.
Gulping down the acrid, salty mess, Richard coughed and no sooner had he swallowed the last drops of Alex’s cum, Dilan recommenced her assault on his naked bottom.
Another six strokes had Richard’s poor bottom on fire and this was only half way to being over.
Dilan gave his chance to recompose himself as the pain of the twelfth stroke seared through his flesh. Dilan was delighted with her accuracy. Clearly, the practice sessions she had with her friend over the last weekends had to paid off.
Dilan strolled around Richards outstretched body, flexing the cane between her hands and occasionally sweeping the long rod through the air. Each time, the sound made Richard flinch with an expectation that his flesh would feel the force of her stroke.
“Two more sets of six for you pretty becky,” she warned.
“Yes Miss,” he replied.
Each of the next five strokes were delivered with ruthless precision, squarely across his ass. His bottom was a mess of hot, red wheals.
The 18th stroke caught the top of his thighs, just a few centimetres above his stocking tops. Richard yelled. “Oww!”
“Oh poor becky, did that hurt! That’s a rhetorical question by the way. I expect, just a thank you,” she said, with a hint of malicious sarcasm.
“Thank you Miss,” Richard managed, through gritted teeth.
The last six strokes were the hardest. Each one crossed other swollen, hot tracks of the others. Richard managed to thank Dilan for each stroke and when the last stroke landed on his smarting rump, Richard drifted into the fuzz of sub space. His mouth was still full of the salty aftertaste of his first blow job and his head was floating with a mix of pain and ecstasy.
Dilan’s cool finger tips were on his bottom, gently exploring the lines she had created. She felt such satisfaction and a little admiration for her submissive’s resilience.
In her tight skirt, Dilan managed to kneel beside his wigged head. She took a lock of long, dark hair in her hand and tugged it aside. Richard turned his head to look at her pretty face and then, dear Dilan moved her lips towards his powdered, made up cheek and placed a kiss on his skin. Richard, momentarily; caught the smell of her perfume and gasped as his senses rallied.
“Thank you Miss, thank you,” Richard turned his head to her. His face was a mess of smudged lipstick, mascara and cum.
“Poor becky,” Dilan smiled softly, shaking her head from side to side, gently.