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Monday
Arrived at the office after a routinely dull weekend to find a certain lady not at her desk and remembered that she had told me on Friday that she had taken the week off to attend to some personal matters. Felt a bit pissed off when she mentioned this because I'd been looking forward to some diversions this week. Needn't have worried because she phoned late morning and suggested lunch. Unfortunately by then I'd arranged some visits but said I'd be over at about 4 if that was OK.

It was OK and so just before 4, I was knocking on her door. She called out to find out who was there and then told me to come in and come upstairs. What a sight! She was lying on the bed wearing a short navy blue pleated skirt which was pulled up round her waist, a white cotton shirt with several buttons undone and a blue and red striped school tie. She didn't seem to have a bra on under her shirt but I didn't have much time to look at the top half. What I couldn't look away from was her lower half activities. She was wearing black hold ups and white knickers which were just below her knees and at full stretch over her strained apart thighs. Her head was thrown back and her eyes shut tight as she furiously rubbed her clit with her right forefinger.

She gasped as she saw me standing in the doorway and tried to cover her cunt with her hands.
'I'm sorry Sir' she cried, 'I just got carried away fantasing about you ........ please don't cane me!'

As she saw my look of total astonishment at this outburst, she added ' I know you said I'd get the cane if I played with myself again .. but I couldn't stop myself ......... Oh Sir, please don't cane me in the classroom in the next room'

I wondered what the hell she was talking about and thought the only way to find out was to take a look in the room next door which had been a spare bedroom and store room the last time I'd seen it. Not any more! She'd obviously had a busy weekend in there. The original furniture including the single bed had gone and in it's place was an office desk and chair and an old style school desk ......... one of those with a sloping lid, a ceramic ink pot let into the top and an attached bench seat. Lying casually on top of the office desk were a leather soled slipper, a long crook handled school cane and my leather tawse which I'd left behind for future use after my last visit.

I strolled back into the master bedroom and roughly grabbed her arm and hauled her off the bed and dragged her into the 'classroom'. I told her to stand in front of the desk and I went round and sat on the chair and looked at her. She still had her knickers at 'half mast'. I lectured her about the terrors of masturbation (while all the time having a massive erection myself and really wanting to wank myself off while loooking at her) and finished up by telling her she was going to be caned and ordered her to bend over the front of 'her' class desk.

Picking up the cane from the desk I came round to her side and having lifted her skirt over her back, lined the 40 inch flexible bamboo stick across the centre of her flinching buttocks. The cane came down with a satisfying (to me at least) THWACK causing an angry red line to replace the momentary appearance of a white line as the blood was driven from the point of impact. Eleven more times this happened at the end of which time the early strokes had begun to form themselves into raised ridges and welts. During the early strokes, she clenched her arse cheeks tight but after four or five she began to weave from side to side in a feeble attempt to avoid the onslaught; but to no useful purpose, after all her arse couldn't really move that far away could it?

Afterwards, I ran my hand over her cheeks and down between them where I found her cunt to be satisfyingly wet. Dropping my trousers and underpants to my ankles, I scooped some cunt lubrication up and smeared it round her anal sphincter and having rubbed my own pre-cum (very much in evidence) over the glans of my cock, nuzzled the end against her arsehole. I don't think she was expecting this because she flinched sharply and I have to confess, gave a little shriek as, without further warning I pushed the head of my erection into her rectum and after a little discomfort (for me) managed to bury the entire 7 inch shaft up her arse!

I reached under her chest and ripped the rest of her buttons open so that her tits flopped down onto the wooden desk top and with them sliding backwards and forwards on its surface proceeded to thrust in and out of her arsehole. She spread her legs and cheeks and gripped the legs of the desk tightly and on each thrust gave a small satisfied grunt and thrust back to meet each one. As my pace and intensity increased so did hers until I was slamming her so hard that the desk began to move backwards to the wall! Her grunts became moans and then shrieks as the desk rocked backwards off the floor and I grabbed a tit in each hand and squeezed the nipples in time with the fucking strokes. My breathing became noisy as I thrust faster and with shorter strokes; the desk hit the wall and tilted permanently upwards and her feet left the ground! I was panting hard and she was shrieking out and with the noise created by the desk banging into the wall I was really glad she lived in a detached house! I suddenly knew I was cumming and she must have detected the urgency in my strokes because she reached under herself and frigged her clit furiously until I shot my load up into her colon and she climaxed a few seconds later.

When I let my cock slide out of her arsehole it was slick with cum and shit. I told her she was a dirty bugger and made her kneel in front of me and wipe it clean and then fetch a bowl of warm soapy water and wash it. As she walked back into the bathroom I could see shit stained cum dribbling out of her arsehole. I told her to strip off and stand in the shower cubicle and wait for me. I unscrewed the shower rose and positioned the end of the hose against her arsehole as she bent over and shot a jet of water inside her and made her wash herself out with her fingers!

I had a shower with her and we towled each other dry which made me start to feel horny again particularly as she spent rather longer than was necessary drying my cock and balls. However, I looked at my watch and realised that I had to get home and so ended this day's diary entry.

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Lynns Diary

Lynn’s Diary: my travels down a road of sexual exploration… My mind is reeling; it’s hard for me to comprehend everything that happened last night. I’m lying here in bed, stark naked, and I’m not alone. (That, in itself, is front page news for me, ever since my divorce four years ago). Not only am I not alone, but the companions are in bed with me. (Yes, there are two of them…) I hardly know where to begin, as I think about how to write today’s diary entry. I look back over the last four...

Hardcore
3 years ago
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My Little Sisters Sex Diary

A few years ago, I moved back in with my parents. I became depressed after the man I loved (supposedly) died while touring in Afghanistan, and I needed the support. When I moved back in, I discovered just how big of a whore my little sister had become while I was away. (And how big of a slut she had been without my noticing.)One Friday night she left to attend a college frat party while mom and dad went on date night. With nothing to do so early in the evening, I decided to do some chores. I...

3 years ago
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Dance Diary

Dec 27, 2006 Dear Diary, Mummy has been as good as her word! She enrolled me today in a ballet school, my Christmas present from her: six months of weekly dance lessons to see if I have what it takes for that kind of life. Do I have the discipline required. The instructor is a rather handsome man in his mid-thirties or early-forties, I'd guess ... but with an athletic build and cute bum ... a dancer in his youth most likely. Not sure if he's gay. Most male dancers are, you know. He was...

2 years ago
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TwinsChapter 5 Diary

Beep, Beep, Beep, Fuck, I forgot to turn that dam alarm clock off again, it’s Saturday morning. But before I could get out of my bed, Darcy came into my room wearing her white robe, and she shut it off. “Dam-it Marcy, it’s Saturday,” she said as she came over to me and sat down on my bed. She then leaned down and kissed me on my lips. I open my mouth and her tongue went into my mouth. I could tell she hadn’t brushed her teeth yet, her breath smelled terrible, but I’m sure mine was just as...

3 years ago
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The Diary

All-in-all this has been a crappy year, so when a heavy package arrived from the law firm of Holland, Scharz and Jacobs I was expecting the worst. Inside the padded manilla shipping envelope were two items. The first was an antique leather-bound journal with a worn strap holding its covers shut, the second was a heavy envelope with my name, Melissa Gordon, written on it in neat (if old-fashioned) cursive hand. The letter inside was typed on expensive heavy-weight paper that had the company...

Interracial
4 years ago
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E105 New Years Day The End Of The Diary

Dorothy and Maude spend the week with Donald and Emma. Twice more, the four women do play together. Once in the afternoon when Donald and Emma are both out, and one night when the two older women slip out in the night, as arranged, to spend the night with Karen and Julie. The morning after that night together, all are a bit groggy at breakfast.Donald and Emma want Dorothy and Maude to stay through New Year’s, but the women say no, they want to enjoy being on the train heading home on New Year’s...

Love Stories
4 years ago
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Lindseys diary

Dear diary Sept 12 Saturday, OMG diary this is the first time I have made an entry that really feels like it means something. Today, well tonight actually mom drank almost half a bottle of wine and got really drunk. She started crying and apologizing to me but I couldn't get her to tell me why she was sorry at first. Finally she said it was because she was such a geek, and that she knows that she raised me to be such a geek too. I think that its because she's really lonely, all...

3 years ago
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Great Grand Mothers Brothel Diary

This is a different story format, is historically correct, uses real Western lanquage. and grammer. Hope you enjoy reading it. I always heard stories about how her f****y was one of the first families to settle Durango Colorado. Well my Grandma Putnam finally passed and my mother wanted me to go through all the old f****y papers and heirlooms. I started rummaging through a trunk and found an old leather binder entitled “Madam Patricia Putnam, Business Diary 1875 – 1895”. It must have been...

3 years ago
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My srs Diary

I’m Tom. I am a hard working senior in college with a minimum wage job and a loving f****y. I have a younger s****r that means the world to me, a mother and a father that have helped me get through all kind of tough times and help me out every step of the way. I also have four of the best friends in the world, or so I thought until I rooted through my s****r’s diary. I wasn’t just snooping around, I was worried. It went like this: I noticed that my s****r was dressing in skimpier and skimpier...

2 years ago
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My srs Diary

I’m Tom. I am a hard working senior in college with a minimum wage job and a loving f****y. I have a younger s****r that means the world to me, a mother and a father that have helped me get through all kind of tough times and help me out every step of the way. I also have four of the best friends in the world, or so I thought until I rooted through my s****r’s diary. I wasn’t just snooping around, I was worried. It went like this: I noticed that my s****r was dressing in skimpier and skimpier...

3 years ago
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Dear Diary

January 1st 2017Dear Diary,Well, I did it again. New Year’s resolution nailed within half an hour of the clock striking twelve. And why not, eh? Why set targets that take all year when you can get immediate results?It’s Saskia’s fault. This year, last year and the year before. All her. She’s a bad influence. She arranged things in advance this time - practically sold tickets. Brazen slut! She’s terrible but you’ve got to love her. You should have seen what she was wearing last night. Absolutely...

Oral Sex
2 years ago
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Her Diary

We were having coffee after dinner when she excused herself, with a wink, to visit the restroom. For no particular reason, I glanced at her open purse lying on the table and noticed the small pink book that said “Diary” on the cover. I sheepishly pulled it out and fanned the pages to browse its contents. My heart nearly stopped beating when I read the latest entry: "Dear Diary, I’m going out with him again this week and it is so bitter sweet. Such a sweet, generous man, but one who is very...

Fetish
2 years ago
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Great Grand Motherrsquos Brothel Diary

This is a different story format, is historically correct, uses real Western lanquage. and grammer. Hope you enjoy reading it. I always heard stories about how her family was one of the first families to settle Durango Colorado. Well my Grandma Putnam finally passed and my mother wanted me to go through all the old family papers and heirlooms. I started rummaging through a trunk and found an old leather binder entitled “Madam Patricia Putnam, Business Diary 1875 – 1895”. It must have been...

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