The Babysitter's Story: Jane

The Babysitter's Story: Jane

This account assumes that Jane just by chance reads my previous three tales and recognises herself as one of the participants. It is the 4^th story in the series.

What a strange world it is. Fifteen years ago, I encountered a 19 year old young man whom by chance I found masturbating, and whom I then manipulated so that I could cane him. And then one day I read a thinly veiled story describing this experience and then two further descriptions of the effect it had on his life.

I am no longer the Jane of David's recollection or fantasy and am now in my mid-forties. I was not in my mid-thirties when he knew me but had just turned thirty. I suppose he thought I was older because my husband was obviously older than I was, and we were good friends with his parents. I was also fortunate enough to be able to dress well and this added to the image of my maturity.

I am still well turned out and turn heads when I walk down the road.

I always knew that David fancied me but never thought much of it. It was flattering to see him follow me with his eyes when he thought I was not looking but until I read his account of this I did not know how much he lusted for me.

I was extremely attractive when I was younger and was used to my fellow male students wanting to bed me, but either being too frightened to try, or being to hormone driven to be attractive. It was always the reticent ones I fancied, but when they failed to approach me I was too shy to make the first move. When I was at University during the early sixties it was fashionable to take drugs and be promiscuous, but I was neither. I was quiet, serious, and studious. My first boyfriend was a graduate student several years older than me, and It was he who uncovered my latent and repressed sexuality.

He showed me a part of myself I had never known and after he had taken my virginity we fucked each other almost every day of the week for several months. We used all the household furniture in his flat, and every one of the nine positions, until one morning I woke up and decided it was time to move on. Something was missing in our relationship, and I was not sure what it was. Although we were not in love, I knew it was not love I was missing but something else.

A couple of boyfriends later, when I was In my last year at University, I was at the theatre with one of my girlfriends when I met Christopher. I did not so much meet him as encounter him when he spilt his drink over my skirt in the bar during the intermission. He was very apologetic and quite charming, and offered to dry clean my dress, and asked for my telephone number which I was happy to provide.

Christopher was a businessman in his mid-forties and fifteen years older than me. He was single, confident, outgoing, good looking and rich. It was the latter that made my parents overlook our age difference, but for me it was something else. He was a masochist, and early in our relationship he confided that he would like me to punish him, and I was happy to oblige. I loved wielding the strap, paddle or cane, and would regularly bend him over a chair, the bed, or the table to administer discipline to his bare arse, and I loved doing it. I had also learnt what had been missing in my previous relationships.

At the time I caned David I had been married 8 years or so, and whilst life was comfortable and I still loved Christopher, the first passion of marriage was gone. He was away from home for extended periods on business and would work long hours when he was not absent abroad. I was left to look after Mary our daughter much of the time. Our sex life started to suffer and when David came to babysit I had not administered a sound beating for at least 2 months and had had perfunctory unsatisfactory sex just twice. I was bored and frustrated.

And then that Christmas, David came to babysit. I had planned to return home after midnight, but the party was boring and the company poor, and because I was driving and had a seven-year-old child at home I had decided not to drink. The result was I was home early at just after 11 o'clock and found David playing with himself.

Unbeknown to David I quite liked him. He was tall, good looking and lean with a nice bum. Additionally, he was quiet and polite. He was also not as much younger than me as he thought.

Even as I scolded him, I was feigning my anger and knew I would never have told his parents what he had done. Before he left the house that evening I planned to cane him. I had never punished anybody other than my husband, and not recently at that. The thought of what I selfishly planned for David made me wet with need.

I went to my bedroom, locked the door, stripped myself naked and lay on the bed in front of the mirror with my legs wide and fucked myself with my 9-inch penis shaped dildo and then applied my brand-new Hitachi wand to my cunt lips and clitoris. As my pleasure built to a climax and as my vagina and clitoris rhythmically relaxed and contracted in orgasm, I watched myself in the mirror and thought about what I would do to David the following evening. And as I lay in the dark, the irony that I was going to punish him for trying to do what I had just done was not lost on me.

The following evening, he turned up promptly as he has described. I had dressed in tight stockings and a miniskirt, and I now understand that I was dressing up to look sexy for him. As it happens I was remarkably successful.

As the caning progressed and as the bright red stripes appeared on his pale muscular buttocks and as he struggled whimpered and sobbed my enjoyment grew. I cannot know much he suffered under the whippy cane as it whooped and slapped but it must have been considerable. When I had finished delivering the allotted twelve strokes, my attentions had had an unexpected but predictable response.

When I saw his long, hard, erect, and uncut penis I knew that I must give him relief. He had suffered for my pleasure, and it seemed a small price to pay particularly since I was already aroused, I loved to give a hand job, and even back then had very skilled hands.

I like to stroke an uncircumcised penis most. By gripping the foreskin between finger and thumb you can slide it up and down over the glans so that the helmet appears disappears and appears again. If you get the grip exactly right it will swell and turn blue. I wanked him slowly to increase his pleasure and edged him to his orgasm, and when this happened he ejaculated long and hard over my lap and onto the carpet. As he came he groaned again.

I remember giving him the four penalty strokes which wasn't fair, but I was feeling horny and was selfish.

And then when he had left, I went straight to my bed, stripped myself naked and re-ran the memory of the night whilst seeing to myself using my fingers, dildo, and wand.

I am no longer married to Christopher. He had several affairs which destroyed my trust in him, although on each occasion I made him understand the error of his ways. Eventually he had on affair too many and I divorced him and took a sizeable settlement both for myself and my daughter. I now must seek my carnal pleasures elsewhere and it is surprising how many men will submit to being disciplined by an attractive older woman. I no longer believe as I did that a marriage and monogamy are synonymous.

That evening, after I released David having watched his beautiful naked body moving in rhythm with the cane strokes and understanding his desire to have me, I was close to giving myself to him. I had not set out to be unfaithful to Christopher, although If David had asked he could have fucked me, and I would have been unable to refuse him.

Now, after reading his account It appears that when I was lying in my bed masturbating and thinking of him, David was in his bed doing the same and thinking of me. And now I wish I had taken my clothes off, showed him my naked and oh so beddable young body, allowed him to play out the sexual fantasies he had regarding me, and given him the best fuck of his young life. But there again what stories would he have told Georgina and what measures would she have had to have taken to find a solution?