Gillian’s Spanking Addiction Ch. 04

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“I saw your striptease on the web last week and I thought I’d give you a call and say how erotic I thought it was.”

“Thank you, Mister Williams. Yeah, that one was hot. One of my cosplay shows with my friend Samantha.”

“Quite, I downloaded it and have wanked off to it every day for the last week. If you are up for it I would take great pleasure in hooking up with you once more.”

The sixty something retired school teacher had met Gillian Atkins on a number of occasions in recent times and the expert spankologist had introduced her to the delights of spanking and the cane. The naturally sexual creature that she was had been greatly taken by the new joys of corporal punishment as a means of deriving gratification and the experience had been a life changing one.

“What do you have in mind?” She asked.

“I would be eternally grateful for a personal show from you and your delightful friend. In costume. I have a passion for fifties Hollywood and seeing you and Samantha in character would be one of my dreams come true.”

Gillian, a twenty six year old webcam model, had been a regular sight on various X rated sites and was immensely proud of her body. With ample cleavage from her 36D tits, and a respectable five feet seven, the long legged stunner had a figure that turned most men’s heads.

“Any actresses in particular?” She asked.

“Oh yes. Marilyn Monroe and Jane Russell. Two of my favourite sex bombs from the silver screen. And one other thing, my dear.”

“I think I know what you’re going to ask.”

“You know me well. Do you suppose Samantha would let me spank her? I shall pay handsomely, I have a generous retirement package.”

“I’m pretty damn certain Samantha will do ANYTHING for five hundred quid. And let me propose that you come to mine. Your place is a little cramped for a threesome.”

“I’m so thrilled! I shall bring my favourite cane! And don’t forget, you must remain in character.”

“Very well then. It’s a date.”

As soon as Gillian hung up she went online and googled the two iconic movie stars from the golden age and boned up on the famous pin ups.


A week later Williams turned up at the West London flat of Gillian’s and was as excited as a boy at Christmas. He wondered what costumes the girls had chosen and his manhood began to stir in his corduroy trousers. The dusk had descended as he arrived and a light drizzle began to hit his uncovered head. He rang the bell and the door was opened by Marilyn Monroe in her white satin halter neck dress that she had worn in ‘The Seven Year itch.’ The famous dress was alluring and left little to the imagination as the neckline plunged to almost the level of her naval.

“Well, hello Mister Williams. Boop, boop be doo!”

The hot blonde smiled and blew a kiss to the waiting man.

“Miss Monroe! You are a vision of loveliness. May I come in?”

“Please do, champagne?”

He shook his head at Samantha presumably, who had transformed into the quintessential Hollywood star with scarlet lip gloss and medium curly platinum blonde wig, the bangs of which fell over her left eyebrow. She was simply stunning as she tottered inside on a pair of white high heeled, peep toe shoes and pointed to a red haired figure on the sofa.

“So, what do you think?”

She did a twirl and the dress lifted to how off a flash of her plump derriere.

“It is a superb get up.”

“This is my friend Jane Russell. Say hi, Jane.”

“Well, well. Look what the cat dragged in. What’s your name buster?”

Gillian lounged on a three seat sofa with a tousled red wig and cowgirl look from the Jane Russell controversial movie ‘The Outlaw.’ Her cleavage revealing green silk blouse fell off her left shoulder as she reclined on her side sipping a from a glass of wine. Her Southern Belle type calf length floral rayon skirt was hiked up to show off substantial thigh. Her lips were a perfect red gash with şişli travesti a slight curl that movie icon Jane always had.

“Mister Williams, charmed to make your acquaintance.” He said with a bow.

He liked a woman with a bit of spirit, just like the real Jane Russell in fact as he eyed her look of disdain.

“Please take a seat.” Said Marilyn.

“Thank you.”

The grey haired man took a look around the modest sized living room and then back to the two beauties. They had done just as he asked and he was highly excited. He himself loved role play and got right into the act.

“So, I believe your movie company wish me to be an advisor regarding one particular tricky scene in your next movie?”

Samantha bent forward opposite Williams and her hefty boobs almost spilled out.

“That’s right,” she answered in her sexy high voice, smiling with white teeth as she spoke. “The scene is a dream sequence. I’m walking down the street above the subway with my boyfriend and the hot air from below blows my dress up and my lower body is exposed. And to my horror I realise that I have forgotten my panties!”

Williams listened with all ears as he pictured the scene and crossed his legs in his seat. Samantha, as Marilyn continued in her breathy voice.

“My boyfriend, in a panic, tries to cover my bared bum and places his hands on my ass. But he gets carried away and caresses and kneads my buttocks until we’re both turned on. We go back to mine where he professes a desire to give my perfect bod a spanking for the public humiliation. Which he does!”

Gillian as Jane stood up, bare footed as she was, and padded over and sat on the arm of Williams seat and played with his hair.

“That is where I come in and join in, except I bring a cane and hand it to the guy and we both get it good from the horny bastard.”

Samantha pouted sexily and gave Williams a suggestive wink.

“So we need your expertise to teach us what to do. What do you say?”

Williams had listened with rapt attention. The premise was child like, ridiculous, and even stupid. But that was not the point.

“It sounds jolly.” He said after some thought.

He settled back in his seat and spread his hands.

“Allow me to introduce myself. For years I taught at an exclusive boys school which had a strict regime for discipline. Backed by the board of governors I, and my colleagues were permitted to administer the cane whenever necessary.”

Samantha and Gillian sat beside each other on the sofa and drank champagne from long stemmed flutes as they listened to the bookish fellow.

“We had a guide line for punishment. The cane was to be delivered across the bare buttocks. The number of strokes between five or thirty, depending on the thickness of the cane mind. I became known as the caning supreme as I developed a certain expertise. I met my dear wife, Ingrid, a teacher at a similar academy for girls and she was my female counterpart. We soon married and discovered a mutual liking for spanking and caning each other. Oh, that first time when I lifted Ingrid’s dress and laid into her nicely curved pair of bottom cheeks with the palm of my hand is forever etched in my mind.”

Williams looked off into the distance as he reminisced and Gillian cleared her throat loudly.

“I thought to start off, you might like to spank Marilyn, to get her warmed up.”

“Capital idea,” agreed the excited man. Turn around please Miss Monroe and show me your bottom.”

Standing directly in the light Marilyn turned to face away and lifted the hem of her dress up over her curvy rump. What an ass! Two symmetrical spheres of pale magnificence was presented to him. He leaned up out of his seat and rubbed the backs of her upper legs, moving higher and higher and stopping just at the small tuft of pubic hair between.

“On my lap, Miss Monroe.”

Samantha gave bakırköy travesti a high pitched giggle as Williams took her by the wrist and she draped over his knees. His hand held her firmly in the small of her back as he raised her dress to her waist to expose her lower body.

“So, you have been quite naughty, Miss Monroe.”

“Yes sir, I have. I went out with no undies. I’m so wicked!”

“I’m now going to chastise you, and when I am done spanking you I shall administer the cane.”

“Ooo, sir!” She cried, getting into the role.

Williams licked his lips as Gillian looked on. He caressed her well rounded buttocks, just like the real Monroe, generously fleshed out without fat. The initial spank had the inevitable response of a jerk and a gasp from the prone woman. The second was now expected but was still followed by a loud inhalation from the blonde.

“Oh, it stings!”

Although cold at first Samantha’s beautiful bottom began to take on a wondrous shade of pink as the elder man started to land firm and open handed smacks squarely on both cheeks. He was methodical and consistent as spank after spank echoed in the room. He concentrated on her left buttock, then the right, and both at the same time as she kicked out her high heels behind her. His knees bent as the exhilarating spanking went on, changing her ass into a glowing target.

“I…I think I like it!”

“What! Wicked child! This is not meant for entertainment!”

Williams was in fact delighted at the proceedings and relished her bum bounce on his lap and the warm sensation on his hand. Gillian had unbuttoned her skirt and kicked it away and stood bared from the waist down, her pussy openly displayed between her parted legs. Now he deliberately grazed her inner thighs and noted the wetness there. With her face nearly on the floor Samantha uttered muted moans as he fingered her vulnerable muff with an ungentle probing.

“Oh, Mister Williams!”

Now fully erect the ex teacher patted her wobbling reddened cheeks and gave her three more measured and hard strikes, one on each globe and one across both for luck.

“Enough, you may get up.”

“Thank you, sir.”

“Now I’m going to cane both of you. Go to the desk Miss Russell and bend over it.”

“Alright feller. If that’s how you get your rocks off, go ahead.”

Gillian pouted for dramatic licence and moved to the desk. The brunette bombshell bent over and wiggled her naked twin moons as she spread her arms wide over the wood top. Williams got up, his corduroy trousers now with a visible tent at the front and picked up his rattan cane.

“This is going to hurt.” He said as a matter of fact as he made contact with her warm bottom.

He moved the cane along the backs of her upper thighs slowly, letting her feel the thin whip. Then he traced out the heavenly contours of her superb nates. He delighted in her ivory flesh with the exquisite dimpled valley.

“Spread your legs.”

“Like this? WOW!”

The first shot was only half strength, a mere flick of his wrist and she was squirming from the shock. Gillian waited for a few seconds, head down and slightly bemused until he struck for the second time slightly harder. This came high up on her red hot buttocks and she flinched and lifted her head.


The third came followed instantaneously by the fourth and Gillian stood up and bit her lip to stifle a scream.

“Assume the position, things are going to get rough.”


His cane rose up high and landed with a resounding crack on her soft flesh and her buttocks recoiled in such a sublime manner that Williams nearly came in his pants! Gillian jerked, her stomach quivered and her spine arched. Samantha winced visibly at every stinging crack her friend took but still remained fascinated by the strange proceedings. And then it happened! Gillian wriggled and writhed istanbul travestileri under a rapid barrage of strikes, her ample boobs pressing into the wood, when with a strangled cry she reached orgasm.

“For fuck sake, don’t stop!”

Gillian’s derriere, now a very rosy hue, lurched up to meet the cane which rained down stinging cracks without respite. Sweat and her love juices ran down her crevice as she spread out her legs wide, Her knuckles were white as snow as she gripped the far edge of the desk. Williams stopped and his soft panting signalled his hearty efforts.

“How the fuck was it?” Asked Samantha, enthralled by the whole episode.

Gillian’s nether cheeks showed red marks that criss crossed deeply across the whole width. She squeezed and fondled the scalding flesh and smiled.

“That was…one of the most enjoyable sexual experiences I have ever had. I love being spanked!”

“Do you think you can handle it, my dear?”

“I guess we’re going to find out.”

Williams took a cushion and placed it on the back of a convenient chair. He motioned with his right hand as Samantha took the dress off over her head and stood naked in white heels. She bent over the back of the chair with the cushion beneath her and grasped the seat with both hands. Her rump was raised up into a perfect pose and Williams clapped his hands.

“I love this bottom.”

Samantha saw nothing as she was bent over, only heard the tell tale swish of the cane as it made contact with her bare buttocks. She screamed from the new type of pain as the instrument cut into her flesh, her tormentor ensuring no portion of her gorgeous buttocks escaped attention.


Samantha began to sob uncontrollably as Williams noted her white posterior assume mottled red patterns. The cane snapped through the air as the nimble sixty year old struck on the same spot again and again. Tears came from her tightly closed eyes as she rolled with the interminable strokes that exploded on her buttocks and thighs. At one point the whip found its way between her upper thighs and kissed the exposed slit of her aching quim. Surprising herself, now beginning to understand Gillian’s view, she felt the tell tale hot and sticky fluids trickle out of her pussy. Gillian looked on, amazed at how such a pale ass could change so into an acute shade of scarlet.

“You may rise, Miss Monroe.”

Slowly and painfully Samantha stood erect, breathing heavily and caressing her burning bum.

“Don’t fret too much. I have brought an excellent soothing lotion with me.”

Samantha stood quite naked, her boobs jiggling slightly as she and Gillian wondered what was next.

“I propose a double whammy so to speak. Would the pair of you bend over, side by side?”

Both women stood next to each other and faced away from the retired school master. Then they bent so far as to almost touch their toes, presenting four magnificent and crimson buttocks.

“Hold steady now.”

Williams stood at an angle as he sized up the prime flesh before him. His erection ached terribly and he released his stiff hose from the confines of his trousers. Then he swept his arm back as gar as possible and brought the cane crashing down across both backsides. Lash after lash rained down on the tormented bottoms that jerked and quivered. Gillian was bruising nicely and her bum was now a livid purple colour from the onslaught. Such was the manner of striking both women together Samantha, being furthest away and so bearing the brunt of the very tip of the cane, showed flecks of blood on her swollen cheeks.

“‘Pon my soul!”

Williams dropped his cane and came up behind both bending women and jerked his cock in his right fist and ejaculated all over Gillian’s right buttock and Samantha’s left. Once spent he tucked his shrivelling prick back into his pants and collapsed in the chair.

“That was truly special. Thank you ladies. I have the cash for you in this envelope.”

Later when he had left the women tended to their punished backsides and discussed their mutual arousal and climax. Gillian laughed and said I told you so.

“I’m gonna be sore for fucking weeks!” Moaned Samantha.

“Well, you got your money.”

“Yes, and I bloody well earned it!”


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