Bossy Boots

I was scarcely able to breathe during the peak of her climax; her thighs like an airtight vice around my neck.

Finally, her grip loosened as she sat panting, her eyes closed. My face was drenched with her juices, as was the dark green leather of her swivel chair.

'Oh my...!' she said finally, looking down at me as she slowly uncrossed her legs from around my neck. 'You made my pussy squirt, Andrew!'

My entire being seemed to be permeated with the taste of her. I knew there was no way that Alison wouldn't smell another woman's pussy on me when I arrived home tonight.

Sylvia sat forward, her legs still spread wide either side of me.

'Is that cock still hard?' she asked, looking down to see.

I leaned back slightly to show her the erection between my legs.

She touched herself with her right hand, slipping two fingers inside her drenched, glistening pussy. She slid them noisily in and out, sighing, for several beautiful moments. She withdrew her fingers and leaned forward to me, wrapping the same hand around the shaft of my hard dick.

I watched as she smeared her juices back and forth along my veiny, hard cock. Her touch was gentle but firm as she stroked me from my balls to the tip of my glans, the underside of which she firmly and adeptly kneaded with her thumb.

'Such a beautiful, hard dick,' she purred, making a tight ring at the base of my swollen glans with her fist.

'Fuck my hand,' she commanded. 'Fuck it slowly, but DO NOT come until I tell you, understand?'

I nodded, my breathing fast and excited as I slowly thrust my erect cock back and forth into her lubricated hand.

'Mmm,' she purred. 'Does your wife like to do this to your hard cock?'

Alison was strictly a missionary position girl, and not incredibly enthusiastic about experimenting with new methods of intimacy.

I nodded, watching her wet thumb glide back and forth with each slow thrust of my painfully erect penis.

'Liar!' she said, squeezing hard then releasing, making me gasp.

'I bet she doesn't even suck this cock anymore,' Sylvia continued. 'Am I right?'

I nodded, this time telling the truth.

Sylvia leaned further forward, pursed her lips and spat on the fat glans of my penis. She smeared her warm spit all the way down to the base of my dick and all around its girth, further lubricating her hand as she continued to wank me.

'Does she like being fucked by this hard cock?' she asked. Her filthy questions were seriously testing my self control. I desperately wanted to come.

I nodded.

'Really?' she probed. 'Does she have a nice, tight cunt like mine?'

I shook my head.

Sylvia laughed. 'How about her asshole then?' she continued. 'Does she let you fuck her in the arse?'

I had to stop thrusting for a moment as I felt my cum surge towards my urethra.

'I DIDN'T TELL YOU TO STOP!!' Sylvia chided angrily.

I slowly resumed fucking her warm, wet hand.

'From your response,' she continued, her tone settling again, 'I'd say that no, your wife doesn't let you fuck her arse, but you'd very much like to do that to her, am I correct?'

I nodded, trying desperately to pace the thrusting of my cock into her teasing, squeezing, stroking hand.

'I'd love to feel a man's cock in my asshole,' she said. 'That's also something my husband has no interest in, despite my many requests.'

I glanced down, reveling in the sight of the tight, pink orifice just beneath her pussy.

'Get closer,' she ordered, 'I want to feel the heat from your cock against my arse.'

Obediently, I shuffled even closer to her on my knees, her hand firmly around my swollen dick as she pulled me towards her. She lifted my cock, tightly pressing the tip of my glans against her arsehole as she continued to stroke me.

She moaned, delighting in the warm, moist sensation against her unexplored anus.

'Oh, that feels so good!' she said, sighing. I couldn't remember a time when my dick had been as unbearably hard as it was at that moment.

Sylvia reached out her free hand and grabbed my tie, pulling me even closer still.

I felt the tip of my cock suddenly penetrate her tight asshole. She yelped as my rock-hard glans suddenly slid up inside her.

'Oh FUCK..!' she swore, loudly. She was practically choking me with my tie as she pulled it, inching me further and further inside her tight arse.

'Mmm..' she sighed, her hips bucking back and forth. 'Your cock is inside me! Oh, your fat fucking cock is in my ass!' I started to slowly fuck Sylvia's asshole; sliding my hard dick back and forth to the sound of her delighted yelps. I started to find it impossible not to come. I could feel the first trickles of my semen escaping into her ass as I slowly inserted and withdrew my cock.

She was frantically masturbating with her free hand, grinding and stroking her well-sucked clit as I fucked her on my knees.

'Aaaaahhh!!' she suddenly moaned. 'Mmmm... Fucking coming...!'

Sylvia started to orgasm for the second time. Her hand went into overdrive against her pussy as she again climaxed, this time with my hard cock deep in her tight arse.

That was it for me. My dick went into meltdown and I finally lost control.

Sylvia suddenly pulled me from her arsehole. She must have felt the spasms of my prick as I started to come inside of her.

She brought her left leg higher and aimed the tip of my cock midway up her leather boot, fiercely wanking the first spurts of my cum all over her footwear.

I moaned with abject delight while my sperm rained down onto my employer's beautiful high-heeled leather boot. There were great wet splodges on her black stockings where it had splashed messily.

Sylvia grinned above me, expertly milking each and every drop of my cum onto her leather boot.

'My, my, my!' she exclaimed. 'That's a lot of spunk, don't you think?'

I gasped and nodded, still kneeling before her.

'Fetch your shirt,' she said sternly, letting my spent cock flop from her hand.

I shuffled over to the pile of my clothes and grabbed my crumpled shirt as commanded.

She extended the cum-smeared leather boot so that its spiked heel dug into my chest painfully.

'Clean it,' she commanded. 'High gloss sheen, nothing less.'

Aw fuck, I thought. Not only do I stink of pussy but my shirt will be stained with my own cum!

Reluctantly, I wrapped my cotton shirt around her boot halfway up her calf. I wiped each droplet of my sperm from the leather, removing each white rivulet as I buffed as hard as I could.

'That's it,' she said, watching. 'Break a sweat!'

I was sweating alright! I sat back, aching, to inspect the boot. My shirt was now a damp, wrinkled disgrace.

Sylvia raised her leg to likewise inspect my efforts.

'That will do, I suppose,' she said.

She suddenly adjusted her position forward and stood up, covering herself once again with her black office skirt.

'Get dressed and get back to work!' she said.

'S..so..' I stammered, hesitantly, 'I...I'm not fired?'

She grinned.

'Not quite yet,' she said. 'But that all depends on you now, doesn't it?'

She turned away, smartening herself up.

I suddenly became excruciatingly aware of my nakedness, not to mention the adulterous acts I had just committed upon my knees. I hurriedly pulled on my damp, bedraggled shirt and yanked on my trousers. I couldn't even wait to put my socks on before I donned my shoes and left Sylvia's office in silence.

On one hand, I felt relieved that I was still employed. On the other, I felt sick with guilt; guilt because I, a married man, had just been sucking and fucking a married woman who wasn't my wife.

Jill glanced up at me as I arrived back in my office. I saw her quickly inspect my crinkled shirt before looking away without speaking. Did she somehow know?, I asked myself.

There was an email waiting for me. It was from Sylvia. My heart almost stopped when I started reading:

"Andrew. Your assistance is required at a two-day conference in Stratford this Thursday & Friday with me."

I swallowed hard.

"I'm adding this part to the deal, which is as yet unfulfilled as far as I can see. See you Thursday : )"

My heart sank. There was no way out.

I opened my desk drawer and retrieved my mobile. I selected a name from my phonebook and hit the green 'dial' key.

'Hello?' Alison answered.

'Hey,' I said.

'Andrew,' she replied. 'What's up? You sound unhappy about something.'

'Alison,' I said, feeling tears well in my eyes. 'We need to talk....'