Straight A's

Story Info
An error of judgement leads to an unexpected result
5.6k words
4.64
7.4k
2
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

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
TheDok
TheDok
282 Followers

This is my third and final story about Jessie and James.

1

My name is Andrea. I am a thirty nine year old solicitor. I am recently divorced and live alone. My interests include cooking and good food, reading, travel, music, art, cinema, and sex, and certainly not in that order.

I often smile when a young man or woman is introduced to the audience during a television chat show or quiz, and they declare an interest in reading or travel but never mention sex. The average number of times a married couple has sex has been variously reported as twice a week to once a month and whilst only around 10% of females my age are reported to masturbate twice to three times weekly this is obviously far more often than they read, judging by their dismal performances, anything worthwhile. And visiting Magaluf once a year to drink "tea likes mother makes" doesn't make you a traveller either.

When I was married I fucked twice to three times a week and in between, on the other days, I masturbated. I'm multiorgasmic and come several times in a session but let's not bother estimating how many time I came or come in a week. Let's just say sex is an interest of mine.

Unfortunately since my divorce, and prior to the events I am going to describe, I had been off men. My ex had not just been unfaithful to me with his secretary, but he had shagged her in our bed. After I had thrown him out of the house, I had had the bed chopped up for firewood.

It never crossed my mind that I would be so turned on by the sight and sounds of a grown man being made to take a caning. Jessie had told me that her boyfriend was due a sound caning for eyeing up another woman. That woman was me and I had been invited to witness James's punishment.

It had all started about six weeks ago when Jessie and I met by chance when I was in town. We were old friends from College but had gone our separate ways after graduating and slowly lost touch. It was five years and the divorce since we had spoken last, and we had agreed to go out for a drink a few nights later.

I am a straight girl with an interest in well hung men and jessie knew that. I also knew that Jessie was bi, but what I didn't know was that she was a dom. We spent some time catching up on our lives since college, and I told her about my disastrous marriage with my cheating bastard ex-husband and what I'd like to do to him. Jessie was sympathetic but then asked the question.

"Wouldn't you have liked to punish him for what he did?"

"You mean apart from half the house and the cash settlement?," I said.

"Damn right. A bloody good thrashing."

And then she opened up to me and told me about her relationship with James. I suspect that if she hadn't had the best part of a bottle of wine she might have said less.

They had been going out for the last three years and she ruled the roost. Although she didn't have any male lovers other than him she slept with any woman she wanted, whilst he most definitely did not have permission to even look at another woman without her say so. On the odd occasion that he had, this had resulted in him being tied bare assed over the dining room table for a minimum of eighteen strokes of the punishment cane.

"He is occasionally allowed another woman but only if I say so."

"And he also gets his bare arse disciplined when he deserves it for any other reason too."

"Wouldn't you just love to be able to be able to do that to your ex just the once?"

And I knew I would.

2

I didn't hear from jessie for about a week following that, but that conversation had planted a seed in my mind, and I started to imagine having my adulterous ex stretched out and tied down for me to punish him. I knew it was just a fantasy, but it was a pleasant thought.

Unfortunately, a fantasy was all it was because I had never been caned and I had never seen a caning. Nonetheless I was certain I could have done a good job.

I am very fit, and tall; five feet eleven inches in my stockinged feet. I play tennis and have a good service game. I have an extremely strong right arm and I am sure these physical attributes would have been well suited to the task of delivering an effective and painful caning.

And, I am considered to be very beautiful, whilst I am very black, and this is the reason why James earned his caning and I got to witness it.

Jessie had invited me to her house for a meal and introduced me to James. He was not what I expected. He was tall, slim, blond, self-assured, and good looking, and additionally he was witty and good company. If that wasn't enough he was educated, well-travelled, and had excellent general knowledge. I was extremely attracted to him but did my best to hide this. I thought he was far too good for Jessie.

Jessie, James, and I spent an enjoyable evening together before I left to go home just before midnight. We got through at least 4 bottles of wine and a couple of glasses of brandy each during the course of the evening.

As the evening progressed I was aware that James was studying me when he thought I, and more importantly Jessie, was not looking. I remember thinking that If I had noticed this then Jessie must surely have noticed too.

As I drove home I feared that James and his beautiful body would soon lie bound and stretched out over the table we had sat at that evening, and that he would receive an extremely uncomfortable bare arse caning. A minimum of eighteen strokes.

I should have felt guilty. After all it was my body that had earnt him his punishment. Instead I found myself wishing I could watch it happen and began to feel moisture and tingling between my legs.

When I reached home I showered and went to bed with my vibrating dildo and my wand, whilst my fifty inch wall mounted flatscreen television played an mp4 file that I had downloaded earlier.

And as a young, fairly attractive, white, naked, small titted, lithe, Easter European woman mercilessly caned an immobilised, bare, male ass until it was striped and bloody, a middle aged, extremely beautiful, naked, black, big breasted, and well-built Sudanese woman watched. As the punishment proceeded she lay back with a dildo deep inside her cunt and applied a wand to her swollen and engorged clitoris until her thick thighs trembled, her ample arse cheeks clenched, her wet vagina clamped down over the dildo, and she moaned long and hard and orgasmed.

3

The following morning was a Saturday and I phoned Jessie to say thank you for a pleasant evening, and before I finished the call I built up my courage and asked,

"I suppose I've earnt him a caning?"

"No he earnt it himself. He knows the rules."

"When will it happen?"

"Not until a week next Friday. I like to cane him on Fridays to give him the weekend to recover and Thursday is his birthday so it will be a present he will have plenty of time to look forward to."

Then, before I could stop myself I blurted out,

"Can I watch?"

And I bit my lip. I shouldn't have worried.

"What a good idea. I know he fancies you. He was stupid enough to tell me that last night when he was still a little drunk. He told me has always dreamt of sleeping with a black woman. I've already told him he's going to get eighteen strokes for his trouble. It will add to his discomfort if the cause of his problems is there to see him get what's coming to him."

"I'll call you in the week."

We said our goodbyes and I put the phone down.

Then I went straight back to my bed, stripped naked, switched on the television, and reached for my toys.

4

The Friday evening that James was to be punished had arrived. Jessie had telephoned me a few days earlier to discuss arrangements. She asked me to be there at ten pm. She planned to punish him at eleven o'clock and he would go straight to bed afterwards. We would have a drink before she started.

As any woman knows appropriate choice of clothes is an important part of an evening out and this occasion was no different. I had decided on a red, thigh length, low cut dress with boots: an outfit which showed off my best features; my 40 inch tits and my thighs. It was only as I stood at the front door of James's and Jessie's house that I realised that I had dressed for the benefit of James.

Under the circumstances it seemed a little perverse, since I imagined that James wouldn't be spending a lot of time studying my cleavage, or my thighs and the promise of what lay between them. I thought it more likely that his thoughts would be centred on the considerable pain and damage to his arse that Jessica was about to deliver. I was wrong.

I rang the bell and Jessica let me in. She showed me through to the open plan lounge-dining room and offered me a seat in an armchair and then poured us both a glass of cold white wine.

Just as I had, Jessie had dressed for the occasion. Her outfit was Jog pants and a loose, white, sleeveless tee shirt with no bra and her feet were bare.

The preparations had been made. The dining table was bare apart from a cushion, some lengths of rope, a leather strap with a wooden handle, and a nasty looking punishment cane.

"He's had a bath and is sitting in our bedroom in his pyjamas anticipating his punishment."

"He'll come down at eleven o'clock. Not a minute late or a minute early otherwise he'll earn himself extra strokes."

We sat drinking wine as the clock hand moved towards eleven, when just as predicted James appeared and stood at the door.

"Come over here and remove your pyjamas."

And he did. First he removed his top to reveal his flat abdomen and muscular torso, and then he stepped out of his trousers. He stood naked in front of us, and his arousal was apparent. His long thick uncircumcised penis stood proudly to attention. And he looked Jessie in the eye and then at my cleavage.

And I saw Jessies eyes harden, and I inwardly remarked at my thoughtlessness in wearing a dress that would earn him further punishment, then almost simultaneously wondered whether that was what I intended.

In that moment I knew two things. I wanted to see his beautiful buttocks writhe under the cane, and I wanted to feel his hands on me and his beautiful long hard manhood deep inside me. And I grew wet in my desire.

Jessies tied him down over the table. He didn't resist and as he lay passive and accepting she took the leather strap in her hands. It was about two feet long including its wooden handle and the leather was dark brown and well-oiled and looked to be about 4 inches wide.

She looked down at his pale white and as yet unmarked bum cheeks, and I could see her measure the strap and take aim, and I heard her speak.

"I'm going to make you so sorry you ever met Andrea. I'm going to make you suffer and I'm going to enjoy doing it so much."

Then she brought the strap sweeping down across the centre of his bottom with a loud slap and almost immediately an oblong area of skin turned a bright pink. After twenty seconds she struck again, and as the strap cracked against his bare flesh a fresh overlapping oblong of pink appeared, and as his arse rose and fell so did jessies strong right arm.

After twelve strokes James's buttocks were a rosy, red colour but so far he had made little sound although the movement of his bum was evidence of the pain he must have been feeling.

And then Jessie picked up the cane and assumed a position to the left and a little forward of his arse. I remember the cane was about a yard long with a red leather grip. She flexed it a couple of times and I could see how supple it was.

She measured the cane across his bum cheeks and struck.

The stroke was venomous. When she had used the strap she had raised it slowly above her head before bringing it down. Now she whipped her arm quickly behind and above her, and in the same fluid movement brought the whistling cane down again, slicing downwards and across, and driving it biting into his exposed arse.

I now know that this technique of caning ensures the cane is bent almost double with the tip touching the caners back before the downstroke begins. This delivers more energy and is much more painful.

A white stripe appeared and rapidly turned red. His bum cheeks contracted. He groaned.

I watched mesmerised as she delivered five more strokes at well-timed intervals to his writhing buttocks, whilst all the time James moaned.

She stopped. James lay still and silent with six parallel blue ridges etched onto his buttocks. The tip of the cane had scored him more deeply but there was no bleeding.

Jessie impassively examined the damage she had wrought, took up her position again, and slowly, deliberately, and skilfully administered another six vicious strokes. This set of strokes prompted James's arse to gyrate and struggle involuntary against his bindings whilst his bum cheeks contracted and relaxed, and his moans were loader.

When she rested again, his buttocks were ridged, heavily bruised and swollen but remained unbloodied, and I was amazed by her skill in administering such a severe punishment with comparatively little damage, all of the strokes lying parallel.

I was even more amazed at James's willingness and obvious need to suffer in this way.

Lastly I was more than a little surprised that the enjoyment his caning was giving me. I realised I planned to bed him and take great pleasure doing it, whilst give him great pleasure in return, but for now I had no pity for him.

As he writhed and moaned under the cane, I knew for certain that I was a latent sexual sadist. I would at that moment have happily delivered six further cane strokes, full force, and with all my strength, to his swollen nates, but I would have to settle for a good second best, and watch Jessie do the job.

And so she did. As my moist sex ached for relief under my dress, I watched entranced as Jessie delivered the last six strokes across his backside. But he no long struggled, and he accepted the last of his punishment in silent acceptance and then lay still and glistening with sweat.

5

When I arrived home a little later I was hornier than I could ever remember having been. I lay naked in my bed on my belly as I knew James would be, and with my legs wide and my arse up I reached down and fingered myself. As I lay there in increasing rapture I variously thought of his beautiful buttocks swollen and ridged by the cane, of him being able to see me as I was now with my arse writhing under my own fingers, and the feeling of his long thick penis filling me as he moved in and on me.

I climaxed long and hard but still remained unsated, and it took my nine inch dildo and my wand, and three further orgasms before I was able to sleep and dream of James.

In the following days James was never far from my thoughts. I knew I couldn't ring his house, but I knew who he worked for and that he worked in Manchester. After that it was easy. I rang his workplace and asked to speak to him and was put through to his secretary. I told her I was Andrea Gatwech and gave her my mobile number with a request for him to ring me when it was convenient.

I didn't have to wait long. Fifteen minutes my phone rang.

"Hello Andrea. It's James."

"Hi James. How are you?"

He laughed.

"Healing well."

"Would you like to meet? With your clothes on. At least to begin with!"

There was a pause at the end of the line as the cogs of his brain turned and then he spoke.

"Jess goes away on business for a couple of days next week. Can I ring you when It's certain?"

"Of course you can. Look forward to it."

"Talk to you soon," he said.

And then.

"Don't ring me on this number She checks my phone. I'll delete the call and your number and write it down somewhere safe. Bye."

I spent the next week waiting and then early one morning whilst I was meeting a client my mobile phone rang. It was David. I quickly excused myself and briefly spoke to him.

"She's away from tomorrow morning until Thursday evening."

"Come to my place after work tomorrow 7 pm. I'll cook tea," I said, and I gave him my address.

"Can't talk. I'm with a client."

"Not a problem. See you then," he said, and the phone went dead.

6

After work that day I went shopping for beef, and a few other simple ingredients and spent the evening cooking.

The following day I got home from work early, tidied the house, changed the sheets on my new bed, showered, and made myself beautiful. I wore my red dress again. Then I laid the table, opened a bottle of red wine to breath, and put on the food to warm up. I had made a simple Sudanese beef, spinach, and peanut stew with couscous.

James arrived just after seven o'clock and I showed him in. At first he was a little withdrawn but after a bowl of stew and a glass of wine he relaxed. We sat and talked about everyday things, but we were both distracted in anticipation of what we were going to do to each other a little later; or at least I was!

"You wore the same red dress," he said across the table.

"I swear she hit me harder because she saw me looking again."

I got up from my chair, walked around the end of the table, and stood about a yard from him. Then I reached behind myself and unzipped the back of my dress.

"Since it offends you I'll take it off."

And then I stepped out of it and stood in my red bra and panties.

I looked down at James and saw his eyes widen and his tongue start to moisten his drying lips, and I knew he lusted for me.

I unclipped my bra and as my large tits swung free it fell to the floor at my feet.

James stood, crossed to me, and kissed me on the lips, and I opened my mouth wide and kissed him back. His tongue flickered and danced against mine and for long seconds we stood like this until I felt both his hands slide under my panties and each hand cup a bum cheek. Then in anticipation of what I longed to happen next I moved my legs further apart and as I did his right hand moved around to the front and I felt his fingers move between the lips of my cunt and find my bud and start to rub.

I was so wet and excited, and as he kissed me and I held him tight, I climaxed. My orgasm was the first of many and seemed to go on and on. He stopped rubbing but did not move his fingers as my pleasure continued, and my perineal muscles rhythmically contracted and relaxed.

I knelt in front of him and unfastened his trouser belt, and in one movement pulled down his trousers and underpants to below his knees, and then I started to fellate his long, beautiful cock as he gently held my head between his hands. Soon he signalled for me to stop, and he stood and stepped out of his pants, and I unbuttoned his shirt and kissed his nipples.

I led him silently by the hand to the bedroom and removed my panties. Finally be broke the silence.

"I never imagined any woman could be so beautiful."

As I stood in front of him, and his eyes devoured me, I experienced that rare moment. I felt deliciously naked and wanted by a man, and for just an instant I had the thought that he wanted me not just physically but maybe there was more.

And then the thought was gone eclipsed by my overwhelming physical desire to be fucked by him.

I lay back on the bed spread my legs and he lay between them and then slowly and firmly penetrated me until he was "balls deep." He started to move on me, slowly at first but then quicker and quicker. My desire grew and I reached down between my legs and as his rock hard penis pounded me I frigged myself until I came again. As I tightened my trembling thighs around his waist and my vagina tightened and relaxed my entire world shrank to the ecstasy I was feeling between my legs, and I screamed.

After a minute he withdrew, and I could see he was still hard. He lay on his back and indicated he wanted me to sit astride his face facing his feet. This was new to me and soon the feeling of his tongue licking my clitoris began to take me where I had never been. My clitoris grew and hardened, and as my juices flowed. my pleasure grew, and I reached forward and held his foreskin and slowly stroked him as he licked me. His mushroom head was blue and swollen when I orgasmed screaming uncontrollably once more.

TheDok
TheDok
282 Followers
12