The Diary of a Whore

Tuesday 7.46 a.m

.

Yawning I opened my eyes and rolled over in an empty bed to be greeted by the early morning sunshine flickering through the gaps in the window blinds.

Yesterday had been a busy day for me and by the time Chris and I had finished our pizza, along with a bottle of wine, it had been time for bed. Totally exhausted I had wanted to sleep but my husband had desired me again and I wasn't going to disappoint him.

By the time we had finished making love I could barely keep my eyes open and, snuggled against him, I fell asleep as soon as my head hit the pillow.

I hadn't even heard the alarm going off or my husband showering and getting dressed. It was only a pressing need to go to the bathroom that had finally woken me.

Reluctantly easing myself out from under the duvet I pulled on a robe and, bleary eyed, staggered down the stairs with only a brief diversion to visit the en-suite.

Tuesday 8.15 a.m

.

I had an 11 o'clock appointment with my newest customer, Paul Robertson, to get ready for so I needed to be up fairly early on the Tuesday regardless. Making it downstairs just after eight I was up in time to have breakfast with my husband before he left for work.

Just being awake was something of an achievement in itself though as, after telling Chris all about my engagements on the Monday, he had fucked me once in the kitchen when I got home and then again that night in bed after we had eaten. Combining that with the three clients I had serviced during the previous day meant I was a little sore and desperately wanted a soak in the bath before the day's engagements.

"So, who is it today Abi?" he looked at me over his coffee mug.

I took a mouthful of my own drink "They're both new. Paul Robertson, we met him at the BBQ Saturday. You remember?"

"Oh yeah, the new head of the high school." Chris thought for a moment about who I meant.

"That's the one." I confirmed, "And a guy called Edward D'Angello, apparently he's a friend of William. The guy at the hotel Friday."

"Wow you're getting even more popular. How are you going to fit everyone in?" he looked at me inquisitively.

I shrugged wondering how he would react to what I was going to say, "I know I was thinking the same thing. I might have to work an evening or two and maybe the odd Saturday morning."

As expected, Chris looked at me and frowned "So when would I get some time with my favourite whore?"

"You'll always come first. You know that." I tried to convince him as I reached across the table and squeezed his hand.

"Really!" he was obviously more than a bit resentful about what I had proposed, "It doesn't sound like it."

"There's something else to." I hesitated before continuing.

"What?"

"Umm... Daniel Bradley. My last client yesterday." I didn't look at him as I spoke, "He offered me £1000 to have dinner with him and then spend the night in his bed."

For a moment he didn't say anything, just taking a sip from his mug as he gazed at me.

"Isn't he the guy who owns some IT company?"

I nodded but didn't answer.

"Are you going to do it?"

"I... I said I'd talk to you but I won't... if you don't want me to." I whispered timidly.

"It's a lot of money for one night." He stated flatly.

"You're... more important to me." biting my lip I tried to reassure him.

Glancing at his watch he got up "Let me think on it, I need to get to work now."

Just then my phone pinged,

Can you meet me at my

office at 5.30? I need to

talk to you and Chris.

Roger

"It's from Roger, he wants to see both of us at five-thirty." My face must have shown that I was rather puzzled, "In his office."

"Well, I'd better go." Chris stood up, "I'll see you this evening then, in his office."

I kissed him good-bye and thought about my schedule for the day as I picked up my phone to text Edward D'Angello

Just confirming our

meeting at 3 p.m.

Abigail xx

Two minutes later the reply came back,

I might still be with

my colleague but 3 p.m.

is fine. I'll be in the bar.

With that I went upstairs to take a bath and ease my sore vagina before applying my make-up and getting myself ready for my first appointment of the day.

Tuesday 9.11 a.m.

Sitting in front of my mirror, wrapped in a towel after bathing, I brushed out my long blonde hair before starting on my routine by refixing my false eyelashes and heavily layering on my mascara. A dark eyeshadow and eyeliner followed, emphasising my blue eyes just how I liked them.

I had just finished my make-up when my phone pinged again

Can you make my place?

2 p.m. tomorrow?

Arthur

It was from Arthur Dennison one of my regulars.

I had arranged to see our neighbour Derek Harper at midday so I should be finished there about 1 which would leave me plenty of time to drive across to Arthur's house.

That will be fine

see you at 2

Abigail xx

Arrangements complete I started to get dressed.

As always, I went for stockings. Rolling the black seamed hosiery up my legs and attaching them to the clasps on my blue satin and black lace suspender belt.

Slipping on the matching thong I decided to forego a bra and chose a little bottle green dress that finished mid-thigh, just below my stocking tops, and clung to my slim figure. With a halter neck that left my back bare and plunged between my modest breasts so it exposed the swell of my tits without being to revealing.

Slipping my black strappy stilettos on my feet I collected the small holdall with my school uniform from beside the bed and, after a final check in the long mirror, I made my way downstairs.

I still had a few minutes before I had to leave so, gathering up the dirty laundry, I filled the washing machine and then went to collect my car keys.

Tuesday 10.55 a.m.

The high school was just a twenty-minute drive away and with the traffic light I was there a few minutes early.

Pulling up outside the head masters house I slid out of my mini and, smoothing down my dress, took my holdall from the back seat before walking, a little self-consciously given how I was dressed, up to knock at the front door.

"Ah Abigail, right on time." Paul Robertson greeted me almost immediately, "Do come in."

"Thanks." I smiled and stepped inside, taking a moment to look around me, "Is there somewhere I can change?"

"Of course. Perhaps we should discuss my requirements as well." He suggested as he showed me to a downstairs cloakroom.

"Just tell me what you want, I should be fine unless it's too extreme."

"If you can be a schoolgirl sent to me for punishment. I'll give you 6 strokes of the cane on your bare bottom and then I'll fuck you. Is that agreeable?" He enquired almost apologetically, "I would prefer ten or twelve but I suggest we start slowly and perhaps the next time...."

"Ok we can do ten but I've never been caned before so if I say 'rainbow' you stop immediately?"

"Yes of course. That's perfectly acceptable." With that he left me alone to get changed.

After he had gone, I looked around my temporary dressing room, a small bathroom, off of the tiled hallway, directly across from the head master's study.

Untying the straps behind my neck I took off my dress and hung it on a hook behind the door. Then keeping on my black stockings, suspender belt and thong I slipped into my school uniform; the same short pleated black skirt, white shirt and tie that I had worn for Arthur Dennison the previous Wednesday.

Dressed for the part I was playing I tied my hair neatly into two bunches on either side of my head, securing them with black ribbons, and then stepped out of my temporary changing room.

Strutting sexily into Paul's study I paused in the doorway, trying to look coy as I twisted my blonde hair around my fingers.

"Ah yes, Abigail, I've just read the report on your behaviour." Paul looked up at me from behind his desk, peering at me over his spectacles "What have you got to say for yourself young lady?"

Fidgeting from one foot to the other, I bit my bottom lip "I'm sorry sir. I promise I'll be a good girl from now on."

"You said that the last time you were sent to me."

I gazed at him my blue eyes wide "I... I'll be good in future, I... promise sir."

"Yes, you will be good, but I'm afraid you still have to be punished for your transgressions." He stood up and moved around his desk picking up a thin cane.

Eyeing him nervously as he flexed the slender piece of willow, my apprehension was very real as I continued playing the naughty schoolgirl he wanted.

"Oh God, you're... you're not going to cane my bare bottom...but that's...that's just so humiliating... and will it... will it hurt headmaster?" my voice trembled anxiously.

Paul Robertson swished the thin stick through the air, "A lovely firm young bottom like yours Abigail will really feel the sting of my cane. But I'm sure you'll agree that it's so much better to get this over and done with."

"H... how m... many?" the apprehension in my voice was real.

"Ten, across your bare backside."

My heart thumped alarmingly. Arthur Dennison's spankings always turned me on but I had never been caned before and, as Paul Robertson's face lit up at the prospect, I worried just how much it was going to hurt.

With a twinkle in his eye, the headmaster licked his lips in eager anticipation, a broad grin spreading across his beaming face as he lifted his fearsome looking cane.

Tuesday 11.18 a.m.

"Bend over my desk Abigail, it's ten strokes of the cane on your naked bottom for lying and cheating," said Paul Robertson sternly.

I tottered nervously across to the headmaster's desk on my stiletto heels and bent over as he had ordered. Biting my lip and waiting while he teasingly lifted my little black skirt right up over my slender waist, exposing my stockinged thighs completely.

Listening I heard him gasp out loud, feasting his eyes on my pert white bottom with just a skimpy little thong nestled between my quivering bare buttocks.

"Please don't pull my panties down headmaster," I begged playing my part to the best of my ability, "surely my panties won't protect me from your cane."

He leered at me "I'm sorry Abigail, a caning must be delivered on the bare flesh. School rules."

His thin fingers eagerly tugged at my knickers and I felt them sliding down my long stocking covered legs until my last remnant of modesty nestled around my ankles leaving my shaven vulva laid bare for his eyes to look at.

"Oh my word, that's a splendid little rear young lady,"

I glanced over my shoulder to see him staring lasciviously at my naked arse.

Bent over the desk with my skirt up and my panties down around my feet I trembled when Paul took several practice swings through the air.

Listening to the terrifying 'swish, swish, swish.' of the cane I wriggled my hips uneasily and held my breath. My pussy beginning to pulsate and tingle when I felt that fearful rattan cane tapping lightly on my pert bare bubble butt.

"Oh my God, you're going to cane me, you're... you're actually going to cane me..." I whimpered, blonde hair falling across my face as I kept my head down.

'Swish... crack'.

The first stroke landed across my jiggling arse like a squirt of fire.

"Aaaarghhhh... fucking hell... that hurt!" I jerked upright, shrieking at the sting of the headmaster's ferocious cane as my bottom began to throb painfully.

A firm hand in my back pressed me down across the desktop and I was still gulping for breath when the second stroke landed across my sore backside.

'Swish... crack'.

The fierce whack echoed around the room as I pressed myself against the cold hard desk and felt the fiery flames spread across my scorching buttocks.

"Aaaahhhh... fuck...fuck.... owwwwwwww!" tears started to prick the corners of my eyes as another red welt appeared on my pale skin.

'Swish... crack'.

The third stroke lashed against my burning rear as I trembled, struggling to breathe and wriggling my hips to try ease the sting of the headmaster's whippy cane.

"Owwwwww... fuck, fuck, fuck... that... fucking... hurts!" tears started to trickle down my cheeks, smudging my mascara.

Paul's cold clammy palm gently rubbed my well caned arse and, instinctively, I raised my backside up to meet his tender caress.

"Oh... ohhhhh... shit.... I...!" I gasped at his touch.

"God, you are incredible Abigail. I can understand why Arthur speaks so highly of you."

The headmaster chuckled happily to himself as he admired his handiwork, his fingers tracing along the three sexy stripes that were streaked across my buttocks, equally spaced and glowing a glorious red.

Relaxing as he massaged my sore rear, I unconsciously pushed my bottom up towards the blissful reprieve so my pretty pink pussy peeked out from between my stocking clad thighs. Letting Paul's fingertips trace along my dripping slit and between my puffy labia I groaned softly.

"Mmmmmmm... oh yes, touch me there." I whispered sexily wiggling my hips invitingly at him.

Slowly he pushed a finger into my cunt, making me shiver as the pleasure mixed with the pain. I put my head down, my eyes closing when he added a second, letting him open my pussy up as he crudely fingered me.

"Three down seven more strokes to come young lady," crowed the headmaster, as he withdrew his sticky digits from my vagina.

His comment was quickly followed by the horrifying sound and the fourth strike came down on my quivering bottom.

'Swish... Crack!'

"Aaahhhh... ahhh...ahh.... FUCKKKKKKK!" I screamed, my head jerking up again, my eyes wide, when another stripe was added to my throbbing arse.

'Swish.... Crack!'

The fifth blow snapped across my still jiggling backside, my knuckles turning white as I held onto the edge of the desk bracing myself for another strike.

"Owwwwwwwwwww... owwwwwwwww!" I shrieked and squirmed at the burning pain in my buttocks, the tears rolling freely down my flushed cheeks.

'Swish.... Crack!'

The sixth strike was the hardest so far. It bit painfully at my tender rump and left me gasping for breath as I lay sobbing and panting across the headmaster's desk.

"Rainbow... fucking rainbow... it hurts too much." I had taken six strokes of his cane and now I gave in, the pain from my abused bottom was now to excruciating to bear.

"There, there, poor Abigail, that wasn't so bad, was it? Now then, I'll just apply a little of this soothing cream to make it feel better."

The voice behind me dripped with lust as I lay panting across the desktop waiting for the pain in my rear to gradually subside.

The creamy lotion that he squirted onto my red striped, bare bottom finally quenched the burning and made me groan out loud.

'Oh God yes that feels so good,' I sighed with relief.

Tuesday 11.31 a.m.

Now that the caning was over, I felt the ache of the strokes merging with each other and a not unpleasant tingle spreading across my bare arse. I relaxed again, enjoying the gentle massage from the headmaster, his gnarly old hands tenderly applying the cold cream.

I was still bent right over his desk when his fingers slipped into my dripping pussy for the second time.

"Aaahhh... yes, oh yes." I groaned softly, dropping my head onto my arms as I wiggled my arse at his touch.

"Get your tits out." Paul ordered me, withdrawing his fingers from my cunt.

Slowly I pushed myself upright, wincing slightly from the pain, as my skirt fell back down across my bottom. I looked shyly at the headmaster and undoing my tie I began to unbutton my shirt, pulling the tails out from my skirt so it fell open exposing my small firm breasts.

"Jesus they are absolutely perfect." He croaked, reaching out to cup my left tit.

I giggled and pulled my shirt open wider to give him a better look.

Playing with my breasts he pinched and rolled each of my nipples in turn, making me gasp and tremble as he teased them into firm throbbing peaks.

"I need to fuck you Abigail." twisting me around he pushed me face down across his desk and lifted my skirt up, "Now!"

Stepping out of my knickers I moved my feet wide apart as I heard the sound of his zip being opened. Pushing my bottom up at him I knew he would have a glorious view of my bald wet cleft peeking out at the top of my thighs.

"Oh Shit!" I exclaimed loudly as he unceremoniously rammed his length up my pussy without warning.

Driving his length in as deep as he could I felt his hips press against my sore bum. With his substantial prick stretching my love hole wide he slid his arms around me so his hands could cup and grope my modest tits while he rocked against me.

Latching on to my nipples he started to fuck me. Thrusting in steadily, his shaft splitting my labia open so they cushioned every stroke he made into my juicy cunt.

"Ungh... aaahhh... fuck, oh fuck...yes!" going up onto my toes I started to moan as he plumbed my depths with his hard length.

Bracing myself on my arms with my long blonde hair tumbling across my face I took his cock all the way up inside my dripping slit every time he rammed it in to me. Behind me Paul was grunting with the effort, fingers pinching and rolling my sensitive buds as he drilled me, his cockhead butting my cervix again and again.

"Take it, take my dick, you... dirty... little... slut." gasping, the school's headmaster started to make crude comments as he fucked me.

"Oh fuck yes, fuck me... fuck your dirty little whore." I added my own words that I thought he wanted to hear.

Redoubling his efforts, pistoning his prick into my vagina, he began to force my juices out around the base of his shaft so that they trickled down the inside of my thighs.

"Shit...I'm gonna...fucking... cum soon." I groaned, my orgasm building, as he fucked me hard.

The sound of his skin slapping against mine became louder and more ragged, his hands dropping to my hips to drag me back against him every time he drove his manhood into me.

"Oh fuck... Abigail... oh fuck... I'm... aaaaahhhhhh!" grabbing me tightly he pulled me onto him one last time as he buried his cock in me and came.

Inside me his erection throbbed and pulsed, spurting a torrent of semen into my belly.

"Oh shit...shit...shit, I'm cuuummmmiiiiiinnnnngggggg!" I jerked back against him repeatedly, cumming hard and squealing with delight as I felt him ejaculate inside me.

Tuesday 11.48 a.m.

Paul held me bent over the desk for a couple of minutes, his shaft spasming as it pumped out the final drops of his seed into my compliant form, before easing it out of me.

"My god, Arthur told me you were good but he didn't do you justice. That was incredible." The school headmaster gasped, still breathless, as he stepped back away from me.

Unsteadily I pushed myself upright off the desktop wobbling on my heels with Paul Robertson's sperm dribbling out of my gaping slit and trickling down my thighs onto my stockings.

"Do you mind if I use the toilet? I need to clean up a little." I giggled my hand shoved between my legs.

Grabbing my knickers up off the floor with my free hand I made my customary dash for the bathroom. After letting most of his cum drip out of me I changed back into my normal clothes, packing away my school uniform, and made my way back into the study.

Paul smiled at me, placing the £100 on the desk in front of him, "You really are a most remarkable young lady. I will certainly be calling on your services again."

Thanking him I picked up the money and, still very aware of my tender bottom, set off to get some lunch before my meeting with Edward D'Angello at the airport hotel.