Female Boss's Sexual Plaything

I had been in my new job just a few days when my boss - an attractive 42-year-old called Stephanie - called me into her office.

She wanted me to work overtime that night, and, hoping to make a good impression, I readily agreed.

At 5.30pm, as the rest of the staff were knocking off, I reported to Stephanie in the basement area of the building.

"Your overtime will be four hours," she said, "and you will not be paid for it. This is a test to establish whether you are suitable for my employment."

This took me aback but before I could object Stephanie added: "You will speak only when spoken to and will address me as 'Ma'am' at all times. You will carry out my orders without question - if you want to keep your job. Understand?"

I didn't understand at all but I was desperate to stay in employment.

I'd tasted life on the dole and it didn't agree with me. This job - a filing clerk in the subscriptions department of a small publishing house - wasn't exactly prestigious but it would bring in a monthly pay cheque.

I swallowed my pride and replied: "Yes, Ma'am."

"Good," said Stephanie. "Now strip to the waist."

As I stood there open-mouthed, she added: "You'll do as I say or I'll sack you right here and now for disobedience."

As I peeled off my white cotton shirt, Stephanie opened a cupboard door and pulled out a large canvas bag, from which she extracted a black, lacy bra and tossed the garment onto the floor in front of me.

"Put that on," she ordered.

I didn't like the way this was going at all but I felt I had no option but to comply.

It took me a few minutes to struggle into the bra, which proved to be a very tight fit, the straps biting into my shoulders.

"Now take off your shoes, socks and trousers," my boss commanded.

When I had obeyed this instruction, Stephanie looked me up and down, and said: "Mmmm, I quite like those striped boxer shorts. I think I'll have them as a souvenir. Hand them over"

I could feel my face burning with embarrassment as I slipped off my underpants and presented them to this domineering woman. Stephanie put the boxers in her handbag.

She then spent a few minutes walking around me, inspecting my tackle and arse before delving into the canvas bag again, bringing out panties, suspender belt and stockings, all in black, matching the bra.

"Get these on, and don't take all night about it," she barked.

The knickers were so skimpy that my dick and balls strained painfully against the sheer, silky material.

"That's much better," said Stephanie, as I fixed the stockings onto the suspenders.

"Now bend over that desk."

I stretched myself across the wooden desk in the middle of the room and waited in trepidation.

"How old will you be on your next birthday?" Stephanie asked me conversationally.

"Twenty-two, Ma'am," I replied.

I watched her as she reached into the cupboard again. This time she brought out a three-foot-long rattan cane, which she waved playfully in front of my face.

"So it's twenty-two strokes, then," she said.

Stephanie sat on a swivel chair in front of me and crossed her long legs, tapping the cane against the exposed flesh of her right thigh.

Eventually, she got up and positioned herself behind me, and I felt the cane being gently stroked across my backside. Then the rod was lightly tapping the seat of the panties.

"Ask me nicely for your punishment," she purred in my ear.

"Please, Ma'am, may I have my caning?"

Whack!

Her initial stroke caught me right across the crown of my arse. The intensity of the stinging lash sent an instant newsflash to my brain, whose natural response was to give expression to the physical assault by screaming my bloody head off. But, somehow, I managed not to cry out.

"Oh, the strong, silent type, are we?" mocked my spanker. "Your screams will be reverberating round this basement before I've finished with you, I can assure you of that."

This time I heard the sound of the cane swishing through the air before it cracked down on my backside.

"Aaaah!"

"Getting a little more vocal already, aren't we?" cooed Stephanie. "Well, just twenty more to go now."

The next three strokes came hard and fast.

"That cute little arse of yours warming up a bit?" enquired Stephanie, after I stopped shrieking.

I assumed this was another rhetorical question but I replied anyway.

"Yes, Ma'am."

Stephanie then yanked my panties off completely and ordered me to spread my legs for the rest of my caning.

After the eleventh stroke I was almost in tears, and my throat was sore from repeated screaming.

"Are you ready to beg for mercy, yet, bitch?" Stephanie asked me.

"Yes, Ma'am, please, no more, no more."

"We're only half-way there," said Stephanie. "If I just give you a further six strokes, you'll have to pay a forfeit. All right?"

"Yes, Ma'am, thank you."

Stephanie laid on those six swipes harder than ever, working downwards from the top of my arse, and finishing with a sadistic lash across my thighs.

I writhed on the desktop, gasping for breath between my groans.

"I'll give you a couple of minutes to recover," said Stephanie. "Then you'll pay your forfeit."

My arse was on fire, the pain spreading outwards from its ravaged centre.

Eventually, Stephanie said: "Right, you little slut, get up and position yourself on your back, lengthways on the table."

As I was obeying this instruction, Stephanie dipped into her canvas bag again, bringing out a long, coiled length of cord and a pair of scissors.

She secured my wrists and ankles to the desk legs so I was spreadeagled, unable to move.

Then she pulled up my bra and began raking her fingernails across my nipples.

"Oooh, aaah," I moaned.

"I'm going to torture your tits for another five minutes," Stephanie informed me, "and I expect you to suffer in silence."

She picked up the panties from the floor and forced them into my mouth before getting back to work on my nipples, pinching, twisting and squeezing the sensitive flesh.

By the time she had finished, my nipples were throbbing, red raw. But, despite the pain, I realised I was getting an erection. And so did Stephanie.

Smiling, she whipped the panties out of my mouth and draped them over the tip of my rising cock.

"If a spot of tit torture turns you on so much," she said, "perhaps you'd like me to continue punishing those cute little nipples of yours?"

"No, please, Ma'am," I pleaded.

Never taking her eyes of mine, Stephanie slowly removed her navy-blue blouse and matching knee-length skirt.

She clambered onto the desk and lowered her bottom onto my testicles as she began jabbing my nipples with her fingernails and scraping her high-heels along my inner thighs.

After a few minutes, Stephanie dismounted, and I thought that at last my ordeal was over.

But she had paused only to slip out of her bra and panties. She got back astride me but higher up this time, rubbing her pussy up and down my face.

When she was satisfied her juices were flowing freely, she ordered me to get my tongue working on her clit.

I could hardly breathe but Stephanie wasn't concerned about that; she was enjoying herself too much.

"You like having your face fucked, don't you, you little tart?" she hissed as she moved her body down mine. She reached behind her to take the panties off my dick and then began rubbing her dripping cunt along the length of my engorged cock and across the dome, but never letting my prick slip inside her.

"Please let me fuck you," I begged. "Please, please, please!"

"Not this time," Stephanie replied. "You haven't earned that privilege yet."

She slid of me and untied my right hand.

"Masturbate," she commanded me, "but don't ejaculate until I give you permission - if you know what's good for you."

I started wanking, and Stephanie pushed her voluptuous breasts into my face.

I was working away furiously on my cock but Stephanie ordered me to wank more slowly, reinforcing the command with a long, hard squeeze of my nipples again.

My dick was aching for orgasm.

"Please let me cum," I gasped into Stephanie's tits.

"Keep it going for a further five minutes," she said. "If you cum without permission, I'll leave you tied to the table overnight. Wouldn't that be a nice surprise for the cleaners in the morning?"

Those were the longest five minutes I had ever experienced but eventually I head Stephanie announce: "You can cum now."

I rubbed my prick as hard and fast as I could and exploded within a few seconds.

As I lay there panting, Stephanie got dressed.

I expected her to release me from my bonds but instead she re-tied my right wrist to the desk leg, and popped the panties back into my mouth.

"I'm going for a drink with a few friends," she told me. "I'll bring the girls back with me for a laugh. See you in a couple of hours."

She kissed me on the lips and left.

I struggled for ages, trying to free myself, but Stephanie had done an excellent job with her rope work.

My arse and nipples were still ablaze, and my dick was throbbing. I could feel my spunk snaking its way down my stomach, onto my hips.

Stephanie returned hours later, with three of her friends in tow. The girls thought my predicament was hilarious.

"Look at all that spunk on him," said one of them. "Do you think he's got any more left inside him?

"There's only one way to find out," Stephanie chipped in. "But first," she added to me, "I've got a little surprise for you."

Stephanie opened a drawer in the desk and took out half-a-dozen wooden clothes pegs.

"One for each nipple, four on the balls," she said, handing the pegs to her friends, who took great delight in attaching them as instructed. The pain was immediate and intense.

Stephanie pulled the knickers out of my mouth and said: "Are you thirsty?"

"Yes, Ma,am," I rasped.

"Oh, he's so polite" chirped one of the girls.

Stephanie fetched a tea cup from the cupboard and held it against my stomach, tilting it towards by cock.

"You're going to drink your own spunk," she announced.

Her friends took it in turn to work on my dick and balls, stroking, tweaking, pulling and stretching.

The pegs on my testicles were dancing around cruelly.

When it came to Stephanie's turn, she didn't mess about. My cock was already hard from her friends' ministrations, and Stephanie pumped it relentlessly. As I came, she aimed my prick to direct the spurting semen into the cup. She's done this before, I thought.

"Now get that down you, and make sure you swallow every last drop."

The other girls propped my head up and forced my mouth open so that Stephanie could tip the contents of the cup down my throat.

I spluttered and choked but the girls quickly clamped my jaws together and pinched my nostrils, forcing me to swallow ny spunk.

"Good boy," cried Stephanie. "We'll take your pegs off now, and it's really going to hurt when the blood starts flowing back."

I screamed each time a peg was removed.

Stephanie untied me and the four women walked towards the door.

"You can keep your job - for now," Stephanie called back to me.

She added: "I want you to give my office a thorough cleaning tomorrow morning - 6am start. Don't be late - or else!"