Her New Role
Her New Role: My Secretary-Style, Kinky Office Sex Fantasy
Hannah stood before the door to his office, she didn’t even remember getting up from her desk. The office was quiet, everyone had gone home. She had to go through with it now; her body had decided for her. Raising her hand, she was about to knock when the door swung open.
“Come in, I’ve been waiting for you.”
Eyes to the floor and cheeks flushed red, she shuffled inside. It was clear that this was the boss’s office. A large desk stood proudly in the centre and the back wall seemed to be stuffed with every piece of paper in the history of office paperwork. She lifted her head tentatively as she slowly approached the imposing desk.
Her new boss walked around her to sit in his throne; sumptuously padded leather with plush covered arm rests. The luxurious materials made her lower regions ache. She didn’t quite understand why.
Her drunken promise to an old uni friend on Friday night chanted mercilessly in her mind.
“I can get any man I want. I’ll seduce my new boss. Just wait and see.”
Right now, Friday seemed an age away even if her hangover hadn’t completely subsided. Hannah’s flirtations had most definitely not gone unnoticed. You don’t have to have had sex before to know how to get a man’s attention.
“So, new girl. I noticed you looking at me today. Something you’d like to say to me?”
In hindsight perhaps she hadn’t needed to be so obvious. In truth, he was more attractive than she’d been expecting, even if he was over 20 years her senior. That just added to his appeal. Hannah was done with boys pandering and begging. She wanted an experienced hand. More to the point, she wanted to experience this thing called sex that everyone kept going on about.
“Um, yes Sir. I think you’re actually quite handsome.”
He laughed then; a full on laugh, the loudness of which was shocking in the small room. She tried out a smile; it felt ok so she kept it there.
“For my age, you mean? Yes, I probably am quite a bit older than you. I wonder if you could be taught the right ways to behave.”
The right ways? What could he possibly mean by that?
He moved his piercing eyes away from her face. She naturally followed out of curiosity. Why was he looking at his umbrella stand?
Oh.
They’re not umbrellas.
The slim wooden hooks and sticks looked like the old fashioned canes she’d seen in a few films. She suddenly felt a chill come over her and her eyes shot back to his. She found him watching her with amusement dancing over his face.
“Don’t be scared. I’m not going to hurt you. Not in a bad way, anyway. You’ll enjoy it. I promise. If at any time you want me to stop, or you want to leave, just say ‘red’. That’s your safeword.”
What should she do? She had the feeling that he could be trusted, and that if she asked right now, she would be allowed to go.
But then she’d have no tales to tell, she wouldn’t have had sex (if indeed that was on offer here), she wouldn’t have completed the challenge made to her friend just a couple of days ago.
Were the canes ‘the basics’ he mentioned? She shivered. She looked at him again. Something about him told her she needed this. The tingle taking over her stomach and suffusing her clitoris told her she needed this. She needed it now.
“Ok. What do you want to do?”
Ball in his court. He caught it, and played on.
“I want you to take all your clothes off, fold them neatly and put them on the desk.”
Feeling a little faint, she took a deep breath. Could she do this? Her fingers answered for her.
Slowly she unbuttoned her shirt and slipped it off on to the floor. Goosebumps rose on her arms and her newly revealed breasts. She left her bra on a little longer, an act of futile rebellion no doubt. Reaching around to her back she found the skirt zip and tugged at it until she could shuffle it down into a pool of material at her ankles. Stepping out of it, she also carefully set aside the black low slung heels she’d been wearing all day.
Standing in her white bra and knickers she didn’t feel quite the seductive vixen she’d played while in her new business suit. She felt every bit the inexperienced woman she was.
Daring to glance up at him, she wasn’t reassured by his mercilessly serious expression. He didn’t even give her an encouraging smile, he just expected her to continue. It was clear that he was used to people doing what he said. He deliberately let his gaze drop then, down to her almost naked body. At least he was enjoying the show.
Something about him made her want to please him. To disappoint him was painful to imagine. Her body and mind instinctively knew that he could teach her a new way. Teach her how to behave, how to please, how to please him.
There was no escaping this moment, not unless she wanted to deprive herself of that valuable education. She took a deep breath to calm her nerves.
Unhooking her bra she let it fall from her arms to the floor; she bent over slightly at the same time in another comedic attempt at modesty. Then she hooked her thumbs into the sides of her knickers and pulled them downwards. A final surrender; tearing away the last layer of her innocence.
Her clothes lay in a messy pile at her feet and she stood, naked, vulnerable, obedient.
His pleasure was obvious. She’d done as he’d asked. It hadn’t even been a demand, although the umbrella stand was an unspoken threat.
“Good girl. Put your clothes on my desk.”
It may have been her imagination but even in the fading light she was sure his trouser bulge was larger than it had been. She felt the stirrings of pride that it might be because of her body and her obedience. Along with this pride she felt something else; a wetness pooling between her labia and threatening to escape.
She gathered up her clothes, placing them in a rumpled pile on his desk. He got up and walked around to where she stood. She desperately tried to resist the natural urge to protect her modesty with her arms.
“We’re going to play a few games. You need to trust me. It’s like exercise. It’s all for your own good, although you might struggle at times. You will spread your legs for me, placing your head on the pile of clothes on the desk, and you will put your wrists behind your back. Hold yourself in that position. Do you understand?”
“Yes, Sir…”
Grateful to be able to bury her burning face in her clothes, she hurried into position. Her breasts brushed the edge of the desk once her face was sideways on her clothes. She felt her thigh muscles being stretched as she parted her straight legs.
Slowly, she put her wrists behind her back.
Feeling the cane on the inside of her leg, stroking slowly upwards, over her calf then to the inner area of her thigh; she fought the desire to close her thighs. The movement went higher still, but just as he was about to touch her humiliatingly wet pussy lips, he stopped.
The cane tip made a light, teasing connection with the inside of her other thigh. She nearly leapt off the desk. He stroked slowly, deliberately downwards, with a final touch on the inside of her ankle. Her goosebumps now had goosebumps.
She needed more, even though she didn’t truly understand why. The brand new sensations filling her head and body were addictive. Something about this man taking control was turning her on to insane levels, and he’d barely even touched her with the tip of a wooden cane.
His shadow approached and she knew he had moved closer. The bulge in his trousers brushed over her bare arse, along with the cool leather and metal of his belt.
“You might find this part difficult, so I will help you.”
Taking both of her slim wrists in just one of his large hands, he pinned them to the small of her back. She sensed him lift his arm. The strike was so sudden and so hard that she lifted her head from the table and squealed in anger as much as pain.
“You’re not to say anything, unless that something is ‘Thank you, Sir’,” he told her in a no-nonsense, firm tone.
Ooh, he really was just so arrogant. She felt her wetness finally make a bid for freedom and it coated a small area at the top of her inner thigh.
“Thank you…Sir?” Her questioning tone would no doubt cause a raised eyebrow. He lifted his hand again after first making sure he had a firm grip on both of her wrists.
She wriggled to move away from the oncoming blow but it was no use. He was an expert hand and the strike landed a perfect inch away from the first.
Her squeal broke the silence in the room before she even knew she’d opened her mouth.
“What did I just say?”
“Thank you, Sir…” she mumbled, tears threatening to tumble from her eyes.
He finally let her wrists go after five more strikes. She began to stand upright but his hand over the back of her neck kept her pinned to the desk. Her arse felt as if it were actually on fire.
When he was certain she wouldn’t try to move again, he moved his firm hand away and she was surprised to instantly miss the feel of it. He trailed his fingers down her spine, as if daring her body to respond after that unspoken warning. She didn’t rise to the challenge. She was sure her behind couldn’t take any more punishment.
Sadly he didn’t agree, letting his fingers roam over her burning buttocks, revelling in her piteous moans and small wriggles.
“You did very well. Those were only warm up strokes, but they were enough for a new one like you. Good girl.”
Good girl. That phrase broke the last of her mental defences, and her body followed suit with fresh pussy juice finding its way to the apex of her thighs. Of course he knew the effect he was having. Just to prove it, he felt between her legs and tutted dramatically when his fingers slid against her inner thighs and labia. She groaned.
“You slutty little tease. Here I was thinking you were new to all this. You know exactly what you’re doing, don’t you!”
“No, Sir, I promise… I haven’t done anything, I mean… not like this… well – not like anything!”
He laughed at her panicked tone and she instantly knew he’d been mocking her.
“It seems a shame to waste such ardent desire. I don’t mean just yours, either.”
A slight clank of metal, a gentle swish. He stood behind her and didn’t even bother to hold her down. Craning her head to look she saw him unzip his trousers and reveal his large, proudly erect cock.
Covering himself with a condom, he slid himself to the hilt in her virgin pussy releasing a rough groan. Her body offered no resistance, neither did her mind. She was his, completely. The sensation of a real man filling her pussy with his cock was instantly addictive. Her satisfied moans escaped into the room, echoing his guttural song as he expertly fucked her on his managerial desk.
She was going to enjoy telling Jess about her first day at work. More to the point, she was really going to enjoy her new role.
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