Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
"I'll be in the study when you're ready. You know where the bathroom is don't you?" he continued, turning back to look at me for a moment.
His question was rather unnecessary. I had been to his house several times in the past and knew exactly where everything was and, possibly more importantly, just what he required of me.
Making my way to his downstairs bathroom I closed the door and started to remove my dress, hanging it on a hook behind the door. After that it took me just a few minutes more to finish changing and prepare myself for him.
I always enjoyed my dates with Arthur Dennison, despite his age, he was a lovely man. That always added a great deal to the pleasure he gave me and made me want to please him in return.
Wednesday 2.13 p.m.
Stepping out of the makeshift dressing room I took a breath and crossed the hall to his study, my stiletto heels clicking loudly on the dark wooden parquet flooring.
My long blonde hair had been tied up into two bunches on either side of my head that were held in place with red ribbons. While in place of my dress, I had put on a tight white shirt and an extremely short black pleated skirt which did nothing to conceal the darker bands at the top of my black seamed stockings. A red and grey striped tie completed my makeshift school uniform.
Where Derek Harper liked to abuse me verbally, Arthur Dennison always preferred the schoolgirl look and to mistreat me in a much more physically intimate manner.
Crossing the hall to his study doorway I stood there, leaning against the frame, trying to look as demure and innocent as I possibly could. Biting my lower lip, intertwining my fingers behind my back while twisting one foot against the carpet as I gazed at the floor would, I hoped, give me the look I wanted.
As usual Arthur Dennison kept me waiting although I knew he was still discretely watching me.
"Ah yes Abigail, do you have something you have to tell me?" he asked after a minute or two, looking up from his desk and peering at me over his spectacles.
"Umm... well Mr Dennison... I... err... well I've been a... a very naughty girl." stammering out my part in his favourite little scenario I fluttered my long dark lashes at him.
"Is that all you have to say to me young lady?"
"Sir. Mr Bowen said I had to come and see you." continuing to play my role I threw myself into the part of the naughty schoolgirl, "He caught me behind the gymnasium giving one of the older boys a.... a blow job."
He smiled salaciously at me, "Well we know what happens to naughty little sluts don't we Abigail?"
Reaching down I started to play with the hem of my tiny skirt, lifting it to reveal my bare flesh above my stocking tops.
"No. Please, Sir... I'll be good. I... I promise. I won't misbehave again." I tried to look apprehensive.
"It's too late for that young lady. Naughty girls have to be punished." patting his lap he beckoned me towards him, "Now come here and lay down."
Hesitantly I stepped forwards as he pushed his chair back away from the desk and positioned myself so I was laying across his thighs.
"Please sir... I'll be a good girl. I really will." I bit my bottom lip and looked back up at him, wide-eyed.
"Naughty little sluts like you need to be properly disciplined young lady." He smirked salaciously at me.
Wednesday 2.21 p.m.
Arranged across his lap I suddenly, for no apparent reason, wondered if Mrs. Dennison was at the same bridge afternoon as my neighbour Mrs Harper. The unbidden and totally inappropriate thought made me smile despite the situation I was in.
"Oh!" I jumped slightly, jerked out of my reverie, as my little skirt was raised up over my backside and my tiny black knickers were roughly dragged half way down my legs so they were stretched between my knees.
Gently his fingers caressed my bare bottom, stroking from the tops of my black stockings up over my pert rounded rear and then down again.
"Mmmmmmm.... That's nice!" slowly I began to relax, the soft caresses sending pleasant sensations through my slim frame.
SLAP!
Mr. Dennison's hand suddenly connected firmly with my right buttock, taking me by surprise even though I knew it was coming.
"OWWW!"
I yelped a red hand mark already very apparent on my pale skin.
Immediately the soft, gentle fingers returned, this time slipping between my thighs to trace along the length of my moist pink slit. Teasing my puffy outer lips, they flicked against my swollen clitoris making me shiver with delight.
"Oh yes, that's very nice." I sighed enjoying his touch.
SLAP!
Another smack, this time on my other cheek, made me jump again.
"OWWWWW!"
I squealed louder, wriggling, my backside stinging hotly.
Again, the probing fingers were back, slipping back between my legs and teasing my pussy once more.
"Mmmm... oh yes, yes. That feels so good." my thighs parted as far as my knickers, stretched taut between my knees, would allow.
Lightly easing between my labia, his inquisitive digits nudged my moist entrance before withdrawing and leaving me whimpering for more.
SLAP!
"OUCH... that stings." squeaking loudly I could feel my rump getting redder and smarting hotly.
Another nine firm slaps later my arse was a vivid red and throbbing warmly while I lay prostrate across his lap, his erection pushed against my stomach, kicking my feet and crying. Tears of humiliation were running down my cheeks, making my mascara smudge, leaving me with black ringed eyes.
However, I wasn't just feeling humiliated. The spanking and caresses I had received had aroused me and my inner thighs were sticky with the secretions oozing from my soaked pussy.
Wednesday 2.44 p.m.
Twenty-three minutes later my shaven cunt was dripping, not only with Derek Harper's semen but also with my own juices. The gentle exploring fingers that had invaded my slit between smacks and had split my vagina wide open, had also fingered me almost to the point of orgasm when he stopped spanking me.
"Now, do as you're told and bend over my desk young lady!" he had then ordered gruffly pulling his sticky digits out of my soaking hole.
Wincing slightly at the burning sensation from my abused backside I had obediently done as I was told, standing upright and letting my knickers slide down my legs to puddle around my feet. Then stepping out of them, I had leant across the large mahogany desk, my skirt rucked up over my back with my feet placed well apart and my head down so my very moist, pink slit peeked out invitingly between the tops of my stockinged thighs.
Behind me, as I had waited, I heard movement and the sound of a zipper being drawn down while I bit my lower lip expectantly.
"Unghhhhh... fuck!" grasping the edge of the desk I had gone up onto my toes as seven inches of hard gnarled old cock was unceremoniously driven up into my soaking quim, splitting me wide open.
He may have been in his sixties and retired but Arthur Dennison had a sizeable dick and knew how to use it.
Sheathing his prick in my pussy he had slid his hands around my body to grope my modest perky breasts through my shirt. His fingers teasing my nipples into stiff points that jutted out prominently through the thin material of my top.
"Mmmm... that feels so good. I love it when you play with my tits." murmuring softly in response I wiggled my arse back against him and enjoyed the feel of his hard rod buried up inside my vagina.
Giving my throbbing teats one final pinch and then gripping my hips firmly he had started to fuck me. Steadily pile driving his shaft into me with surprising vigour given his age. My small firm breasts bounced under my blouse, making the sensitive buds rub sensuously against the material, while the old man's hips slapped repeatedly against my still sore bottom.
"Oh shit... you're in me... so deep." gasping I took every stroke, my soft outer lips clinging tightly around his manhood.
"God you're so... fucking... tight!" his moans mixed with my cries as he hammered into me, fingers digging in to the soft flesh of my hips.
Bent over the desk being soundly fucked by a man old enough to be my grandfather was excitingly debauched and always added to the pleasure I felt when I serviced his needs.
"Oh, fuck yes, yes, fuck me, oh god... just fuck me!" shrieking and wriggling I had pushed back and working my sex onto the hard rod plugging my cunt.
Encouraged by my cries he had started pumping furiously, each thrust seemingly harder and faster than the one before it, but each and every one sinking in all the way.
Thrusting back against him I had felt the sensations growing inside me, the heat radiating out from my core as my climax built.
"Oh shit, shit... don't stop... I'm gonna cum...!" Squealing I had lifted my head, my big blue eyes wide open.
"Uhhh... Abigail... Ohhh... shit... Abigail... I...!" he shuddered, burying his prick deep inside me one final time before he ejaculated.
For a moment his whole body had tensed and then he had begun jerking and grunting while his shaft pulsed deep in me, flooding my belly with another copious amount of creamy sticky man seed.
Feeling him shooting his load into me had sent me over the edge and I climaxed a second or two after him, my knees almost buckling under me as my whole body shuddered uncontrollably.
"Fuckkkkkkkkk... I'm.... cummmmiinggggggggggg!" crying out with intense delight I had felt the most amazing, skin-tingling, toe curling and earth-shattering orgasm crash over me.
Unable to move I had clung to the desk, gasping for breath as the waves of ecstasy flowing through me slowly dissipated until I was breathing more evenly. Behind me, panting breathlessly, Arthur Dennison had slowly withdrawn his softening slippery cock from my cum-filled hole.
As he pulled out, he let a large dollop of semen dribble out and start to run down my thigh onto the dark bands at the top of my stockings.
Wednesday 2.47 p.m.
"Fucking hell Abigail, you're worth every penny you charge." he finally wheezed, slumping back into his chair, his pants still down round his ankles.
I slowly pushed myself upright, once again with a hand between my legs to catch the man cream oozing out of my vagina, "Same time next week?"
"Absolutely." he called after me as I hurried off to the bathroom to clean up again.
By the time I had tidied myself up, re-applied my make-up and put my dress back on Arthur was sitting at his desk, fully clothed, looking like nothing untoward had happened between us.
"Thanks." I said picking up the small pile of notes on the corner of his desk, "Will I see you next week?"
"Yes, next week will be absolutely fine, thank you Abigail." As always, he didn't get up to show me out but I knew the way, "The same time?"
"Perfect." Tucking the money into my bag I gave him one last look before I left.
Closing his front door behind me I smiled to myself, having clients like Arthur Dennison made being a whore even more pleasant for me.
Wednesday 2.59 p.m.
I had just made it back to my car, throwing my bag onto the back seat, when my mobile phone rang. Checking the display on the screen I could see it was Roger Crawford, my husband's CEO.
"Hi Roger, what can I do for you?" I answered knowing exactly what he wanted.
I listened to what he was saying, taking a deep breath before answering him.
"Make it 3.45 and it should be fine. Text me the room number. I'll meet you there."
Sighing resignedly, I checked my appearance in the rear-view mirror making sure I looked presentable before setting off for the hotel rendezvous that Roger Crawford had just invited me to.
My husband had said he would be home sometime shortly after 6 so I calculated I should have enough time to see Roger, get home, shower and then start dinner before he got in.
Half-way to the hotel my phone pinged,
Room 3019
it said simply when I glanced down.
Wednesday 3.39 p.m.
Arriving a few minutes early I strolled through the foyer, ignoring the receptionist who looked me up and down and, seeing how I was dressed, instantly labelled me as a working girl. It didn't bother me; I had worked the hotels in the past and I was used to the contemptuous looks I got from the people on the reception desks.
Making it to the elevators without being challenged I pressed the button for the third floor as I got in. It took less than 30 seconds before the doors pinged open ready for me to step out.
The sign on the wall said room 3019 was just a few yards along the corridor to my right.
There was no one around when I took the short walk along the plush carpeted corridor and paused outside the room. Smoothing my dress over my hips I brushed my hair back and took a deep calming breath preparing myself for what I knew would happen.
I had known Roger Crawford in various guises; as my husband's boss, as the first one of my customers and as a complete pervert. It didn't take a lot for me to guess which one it would be today.
He opened the door on my first knock, dressed in just a towel he looked furtively back and forth along the empty hallway before hurriedly ushering me into his suite.
"We only have an hour." As soon as I was inside, I informed my husband's middle-aged, obnoxious and overweight boss while I looked around the luxury hotel room, "I have to get home in time to get dinner ready for Chris."
"You should be there in plenty of time." He grinned lustfully at me, "It'll only take an hour, if you're a good girl that is."
I didn't answer, I knew Roger of old.
Without waiting to be told I simply unzipped my dress and stepped out of it, folding it neatly across the back of a chair. My panties followed immediately after, leaving me in just my stockings and heels.
"Fucking gorgeous, as always!" leering at me his gaze wandered up and down my body as I stood virtually nude before him.
Naked, I dropped to my knees without answering or waiting for his instruction. Then glancing briefly up at his smirking face I pulled the towel away from him and, dropping it to the floor, I wrapped my hand around his semi erect length and started to stroke it.
Like most of my clients Roger was a lot older than either me or my husband. In his early fifties, short and balding he had let himself go and was now quite drastically overheavy. Also, similarly to the majority of my customers, he held little appeal to me physically but he was wealthy and he had a sizeable cock.
Much more importantly though, he owned the company that my husband worked for and had the power to keep Chris and I in the manner to which we had become accustomed.
Lowering my mouth onto his prick I started to suck, taking it in as deep as I could then starting to bob my head, working my lips back and forth along his, now fully erect, shaft.
"Fuck Abigail, you're so bloody good at sucking dick." he groaned, tipping his head back, "I hope you got some lube though, I'm gonna need it soon."
I rolled my eyes as he confirmed my expectations.
For the next few minutes though, I slurped and sucked greedily on his phallus, keeping one eye on my watch, aware of my time constraints. Orally pleasuring him I forced my jaws apart as I struggled to take his thickness deeper trying to get the bulbous crown into my throat.
"Guuurrggggg... Uuuukkkkkkk... Uuuurrrrmmmmm!" my lips tightened around his shaft, increasing his pleasure
Eventually Roger curled his fingers in my long blonde hair and yanked my lips roughly off him, "Fuck it, bend over Abigail, I can't wait any longer. I need to fuck your arse."
I knew exactly what Roger's preference was so, wiping my mouth on the back of my hand, I stood up and fished the tube of lubricant out of my bag. Passing it to him I bent over the bed, my feet wide apart, and waited.
Staring at the opposite wall, my blonde hair falling across my face, I forced myself to relax knowing it would be a lot less painful for me if I could.
Wednesday 4.03 p.m.
"Oh shit, that's cold!" I squeaked as he dribbled the slimy goo onto my arsehole, using a finger to work it up my bottom and around my dark puckered anus before replacing his digit with the tip of his dick.
"Go fucking gently. You're a bit too big." looking nervously back over my shoulder at him, my eyes widened as I waited to take his dick up my back entrance.
"Yeah, yeah, don't worry." he assured me and then, without warning, he shoved himself forward in one vicious, unhesitant thrust that felt like his cock was splitting me in two.
"AAAARRGGHHHHHH... You... fucking.... arsehole... that fucking... hurts!" screaming I went up onto my toes as his full length was rammed unceremoniously up into my bowels.
"Fuck off, whore, you'll get your money," snarling he slammed into me again, "Remember I'm paying you to fuck any hole I want any way I want!"
Anal sex was one of the few unpleasant novelties I tried to avoid when I could, and with good reason. It always hurt as much as I expected, and even though I knew that's what Roger wanted I always hoped he might choose another orifice to deposit his seed in.
Reaching around me to maul my small breasts he started to pound away at my rear. Driving his prick deeper into my anus with every stroke and stretching my sphincter muscles painfully.
"Ow! Owwww! You're fucking... hurting... me!" I squealed, though he probably already knew that.
"I know." his laughter simply confirmed that he knew, "Now stop fucking complaining you're being paid."
Biting my lower lip and, grimacing against the painful abuse of my rectum, I gripped the bedcovers tightly and pushed back urging him as deep as he could go. The pain mixing with the pleasure and creating a unique sensation in my core.
"Fuck... fuck... oh fuck... fuckkkkkkkkkk!" crying out loudly I took his thickness into my rubbery bowels, feeling it stretch me wide open.
He ground his hips against my arse, enjoying his torture of me, "That's so much better, cunt."
The minutes turned to what seemed like hours, but the pain didn't numb. It sounds silly, but when he finally tensed and exploded, grunting like a pig and spilling a load of gross, sticky semen deep into my innards I came as well.
"Ungh... fuck, fuck... oh shit.... yesssssssssssssssssss!" my arsehole clenched around the solid lump of meat being rammed up it.
"Oh fuck... fuck.... I'm gonna cum up your arse whore!" Roger groaned, holding his cock inside my rectum as it pulsed hotly, his balls emptying into me.
I stayed bent over, knuckles white as I gripped the bedsheets, his prick remaining jammed up my bumhole, until he finally pulled out. The quickly softening cock soon followed, slipping easily out of my gaping shit hole followed by a large glob of his sperm.
Wednesday 4.35 p.m.
Wincing slightly, I eventually pushed myself upright and scrambled around for my knickers, quickly tugging them on, ignoring the sticky mess congealing in my panties. My arsehole would be sore for the next couple of days and I hoped no one would want anal during that time.
Pulling on my blue dress I zipped it up and smoothed out my hair, hurrying so I could make it home before my husband got there.
"You'll give me a ring next time you want me?" I asked bluntly, scooping the cash off the side ready to go.
"You can be sure of it." With a smirk he replied as I opened the door to leave, "And thank Chris for the pleasure."
I didn't bother to answer his last sarcastic remark and just firmly pulled the door closed behind me and made my way down to the hotel foyer, ignoring the contemptuous stares, and out to my car.
The drive home took a little longer than my journey here due to the evening traffic building up with people leaving work but I still made it home by five thirty.
