Author’s Note: Annie, Suzy and Emma are real, all other characters are fictional in this story set in September 2018. I’ve been informed that Annie and Suzy actually work in Winchester, but it doesn’t have any sex shops, so their office has been transported to Andover which has ‘An Amazing Fantasy’ (previously enjoyed by some as ‘Erotica Belle’); where Emma may work on occasion. By day, Annie is Suzy’s PA, but when they get home, their roles are reversed: blonde twenty-something mild-mannered Annie becomes leather-clad Anna Dominatrix to her fifty-something submissive ‘posh slut’.

Meeting Mistress

Fourteen-year-old Adam walked hand in hand with his mum across the park. He was wearing his favourite shiny pink leotard under the school blazer, white shoes with kitten heels and white ankle socks. He took small steps to avoid his tiny boy-clit rubbing up another erection inside the soft fabric.

“Look at that lady in the black leather, what’s she doing to that older lady on her knees, mummy?”

“They look like Mistress Anna and her sub, Suzy,” replied mum, trying to shield her son’s eyes.

As they approached, Anna called his Mum by name.

The last time Anna had seen the fiery redhead was at the Club, strapped down half-naked to the spanking bench; the red leather harness bralette only adding to her nakedness.

Master James had taken particular delight in raising the colour of her buttocks to match her long red hair.

“How does she know you, Mum, do you work together in Andover?”

“Yes, that’s it baby”, remembering the excruciating pain from the nipple clamps in that next scene with Anna.

“Hi Mistress, this is Adam, and he’s really keen to get onto the office ‘work experience’ programme. Shall I send him along on Monday?”

“Sure baby girl,” Mistress replied, planting a soft kiss on her neck and rubbing her bottom “I never forget a pretty co-worker. Give her a business card, slut, so she’s got my number.”

Suzy fumbled around inside her bra, pulling out a slightly crumpled card and proudly handed it to Adam “Here you are, little man.”

Adam read the card aloud: “Anna Dominatrix - Discreet Personal Services.” He blushed red, trying to memorise her private contact details.

“Not that one stupid.” Anna slapped Suzy, grabbed the card, and replaced it with the boring one, just saying ‘Ms A Adams - Personal Assistant’ and the office phone number.

“So Adam, tell me, why do you like wearing girls’ clothing?”

Anna had unbuttoned his blazer and was admiring his cock flattened inside the snug leotard.

Mum explained it had started when she had taken him to dance lessons, and he tried on tights for the first time. After that he would run around the house in his big stepsister’s thong, even stealing her bras to wear stuffed with pink socks.

Adam was delighted when sis gave him her old shiny dance leotard. He loved to watch his flat pubic area in the mirror, with his cock safely tucked out of the way between his thighs. Mum sometimes let him watch her showering; then slapped his bottom for cumming in the sink.

Mistress Anna gave Adam a small shiny metal cock restraint. “Here baby, wear this over the weekend and we’ll soon have you acting like the girl you want to be.”

“Thank you, Mistress,” his mum replied. “I’ll make sure he has it on for the interview on Monday, and perhaps his new pink skirt if he’s good.”

Monday Morning Adam arrived bright and early for his ‘interview’ on Monday morning, wearing a short pink top over a heavily padded bra, a short pink skirt, matching tights and those lovely white shoes.

He stood meekly at the reception desk, averting his eyes from the constant stream of health workers, some of whom paused to check him out. “Come up to my office later, little girl,” said one man, “it’s on the top floor - just ask for Master James.”

Adam assumed he had misheard ‘Mister’; looking up replied “Yes Sir.” Feeling a strange tingle in his crotch.

Mum had only allowed him ten minutes out of the cock cage all weekend, for one quick wank and now he was getting desperate.

The male receptionist guided him towards the lifts, but then decided that the stairs might be better for the two short flights up to Anna’s desk. The lower part of Adam’s bottom wiggled deliciously for him, inside the thin white tights, fully visible under the short pink skirt.

The interview was a mere formality - but he struggled on the application form with the Gender and Age questions.

Anna said, “Just leave them blank, nobody would ever notice.”

Adam was set to work delivering the internal mail and was horrified to see the first envelope addressed to Master James - so it was true. “Do I have to, Miss?”

“Of course you do, Adam, it’s all good experience. Here’s some lube and make sure he uses a condom - we don’t want you spreading anything nasty around the office.”

Forty-five minutes later Adam returned, the knees of his pink tights all scuffed and a rather large hole in the back when he bent over Anna’s desk for inspection. She smoothed more lube into his sore, gaping butt hole. “Oh dear, little Man, this does look tender. Let me give you some relief.”

Mistress undid the lock on his cock cage, letting his pent-up erection grow in her hands. “There - isn’t that better, you lovely boy.”

He only lasted thirty seconds of gentle rubbing, even Anna was amazed at the quantity of sperm he released into the carefully positioned tissue when the phone rang.

It was her boss Suzy - better known as ‘posh slut’. “Send him in here, now. I need to check out his oral skills.”

“Come back at lunchtime, Adam and we’ll get you some new tights, these are a disgrace.”

Next door, ‘posh slut’ was sat behind a large desk, legs apart, no knickers, stroking her engorged lips. “I was watching you on the top floor, there are cameras everywhere. I think you did very well for the first time. Now you need to learn to suck pussy. Get your head in here.”

Luckily Adam’s older stepsister had let him practice on her a few times and he quickly picked it up again - running his tongue through the slick folds and around the hard nub.

“Good girl,” she panted “that’s very nice.” Her fingers running up the back of Adam’s neck “Keep sucking, you can use your fingers too if you like.”

Adam bunched his fingers together, just like his stepsister had shown him, and was amazed that his whole fist was swallowed up by the first adult cunt he had ever fisted.

Much later, Adam, moved away, his face coated in lady-cum, very pleased with his first morning.

“OK you can get up now, why don’t you take those ruined tights off, then you can paint your toenails for me.”

Adam sat uncomfortably on the leather sofa, knees drawn up to reach his toes, displaying a delicious slice of slapped buttocks.

“We’ll have to buy you some stay up stockings for those lovely smooth legs. Hmmmm, stockings and a thong, how do you fancy that little girl? The thong can hide your little boy-clit, we don’t want that popping out if you get excited. Perhaps we can even find you a small butt plug for that pretty pink arse. Now bend over, grab your ankles, I think we need to inspect those bruises.”

Adam bent over, gripping his spread ankles, Suzy’s face only inches from his reddened bottom. He jumped when her tongue made contact, then relaxed until he felt a hand squeezing his balls.

“Oh shit, Miss, you mustn’t do that. I might cum all over your sofa.”

“Don’t worry, little lady, I love the taste.”

Adam’s knees buckled as Suzy’s cool tongue pressed into the heat of his rosebud. Her other hand collecting the pre-cum leaking from his boy-clit tip. “Turn around, little man, let mommy drink your lovely sticky sperm.”

Adam’s cock erupted as Suzy’s tongue made contact with his slippery tip. She gulped most of it all down, the remainder splashed onto her white blouse. “Naughty boy, now I’m going to have to take this off. You can finish off between my tits if you like.”

Of course, that was the moment that Mistress Anna knocked and walked straight in; Suzy on her knees, topless, holding her bare breasts wrapped around Adam’s sticky cock.

He was holding her head, covering her ears, so didn’t hear Mistress until she shouted, up close. “What the fuck are you doing to him, boss? I think I need to discipline both of you right now.”

Suzy meekly lay along the back of the sofa, Mistress tightening the straps across her back and legs. Adam ejaculated with every slap on Suzy’s bare arse; Mistress Anna was magnificent.

He couldn’t imagine why she was so angry, then it was his turn.

He offered his sore bottom, but she turned him around and slapped his balls very hard three times. The sperm stopped erupting, all he could manage was, “Sorry Mistress, it won’t happen again.”