Silhouettes of three shapely women on a red background which shows out of focus shots of women’s faces
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Micro Monday, Flash Fiction

First Time with Her New Mistress

A sissy prepares to meet two new mistresses for the first time: Anna was soon strapped onto a strict leather whipping bench and covered in a velvet throw.

Alexander A gibbons
Published in
3 min readJun 13, 2022

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Anna was about to meet her two new mistress for what she hoped would be a double ended session. A striking woman in leather trousers and combat boots approached where she stood on the platform.

Mistress E showed Anna into a kitchen. Anna was offered water while Mistress E disappeared, then returned with a blue dress with a ruffled Victorian collar for Anna to wear. She also brought a variety of different sized dog collars.

Anna sat, wearing a dog collar and nipple clamps. She was feeling great about this session, but she didn’t notice her girly-cock leaking pre-cum. By the smell of her leather trousers, Anna knew Mistress E was close by.

Suddenly, her boots kicked Anna’s balls.

“Naughty slut, that shouldn’t be happening,” Mistress scolded, then took a pink ribbon and tied Anna’s long hair into a ponytail.

That was the moment another woman walked through the door.

Anna was soon strapped onto a strict leather whipping bench and covered in a velvet throw. Her feet were restrained, and she was positioned so her bottom was ready for them.

The new arrival, Mistress B, began slapping Anna’s bum with light spanks using her hands. The blows built up till Anna’s bottom was warm and rosy. Once done, Mistress moved onto six from her various light canes, working towards the extreme black mamba cane.

Both mistresses took turns to mark Anna’s back and bottom till it was covered in stripes, laying some hardcore welts on her backside.

Mistress B surveyed Anna before moving her to a new position. There she resumed paddling Anna with her hands until her rump was bright purple.

Mistress E cast a complicit look towards Mistress B.

“Let’s see if she can do a good job on our boots.”

Anna was pushed to the floor where two pairs of boots were thrust towards her mouth. The boots were dirty, but she obediently commenced licking the leather and shined the buckles with her tongue.

Mistress E smiled faintly. “See, she can do something right. But she still looks like a boy, I think we should shave her tits.”

Anna was forced onto a hard chair.

Mistress E stood in front of her and started to twist her nipples, which were already sore from the nipple clamps. Next, Mistress E squirted a large amount of foam to spread over Anna’s chest. Gradually, using a cutthroat razor, she removed every scrap of Anna’s chest hair.

“Next time,” she warned, “I will have to wax those worthless balls.”

Anna thought she had done a good cleaning job on their boots. However, Mistress B wasn’t satisfied. Taking Anna by her collar, she pushed her sissy face down onto the boots with such force that she marked Anna’s cheek with her boot print.

When it was all over, Anna sat drinking her coffee, while mistress E stroked her long hair. She took time to process what had just happened, wishing she’d taken the black mamba cane, but it had hurt too much, causing her to use the safeword.

Next time, she promised herself. Anna wanted this again and knew she would be back for more.

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Alexander A gibbons
Tantalizing Tales

Hi, I am alexander the writer of many things here now for tantalising tail and other publications. I love going to the cinema reading books, listening to music