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.