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niteowluk2003
06-20-2014, 12:15 AM
The strange way things turn out.
Copyright©2014 Niteowluk2003 – All rights reserved.

Chapter 1.

My son, tom and his current Girlfriend, frequently shared my home; by that I mean that my son despite being 32 was still living at home and although his girlfriend Jenny had bought her own home he chose to remain in my home. This meant that on a few occasions Tom and Jenny shared his bedroom and bed but the strange thing was that on three of those occasions Jenny had stumbled into my bedroom in the middle of the night, stark naked. The third of these occurrence I decided not to do my usual and tell her she was in the wrong bedroom that is until she actually cocked her shapely leg over my prone nude body.

At this point I spoke out and she quietly without saying a word climbed back off the bed and went to Tom’s room. After all three occasions of her coming to my room I would mention it at the following breakfast and she would blush and simply apologise saying she must had been more the worse for drink than she had realised.

Now Jenny was a healthy girl and to many I would say she was attractive but for me to take advantage of her 38 24 32 figure would have been betraying my son, but things took a sudden turn when Tom announced that he and Jenny had decided to take a break from each other; which I gather was the modern day youthful expression of them finishing. So you can probably understand my confusion when Jenny approached me and asked if I could help her.

I had always gotten along with Jenny so I said if I could help I would; she asked me quite openly if I knew why my son was interested in anal sex. I coughed and spluttered a bit suggesting this was not something easily discussed with his dad; but I reversed the question and asked her why she disliked it so much for it to become a problem. She told me a previous boyfriend had tried it and hurt her so much she had bled for a long while afterwards.

I told her it was a shame because young people should enjoy sex in any form and for her to be stigmatised by a bad experience was not really fair. I jokingly told her that if I had been that boyfriend I would have ensured she enjoyed the experience rather than take my own pleasure first. Suddenly out of the blue she asked if I would do just that and then she could decide if anal sex was right for her or not.

I tried to explain that it would look really strange if suddenly after she had gone out with my son for more than a year she suddenly started going out with his father. She said who would know if we met at her house until I had finished teaching her. I could not argue with that but I did say that if she was going to be serious about this then there were a few ground rules to be ironed out first. She simply said I will agree to anything you choose to put in place as a ground rule.

I advised he to listen first before jumping in; I said if I was going to teach her about anal sex then I would insist on teaching her about all aspects of sex and she would be expected to obey my demands and wishes. Instantly she responded I know you would not simply take advantage of me so I agree to everything. With that we arranged to meet at her house the following night, of course without Tom’s knowledge.

I carefully prepared a black flight case with things I wanted to introduce Jenny to and see if she had tried them before. I had a plan for the night running through my head which meant that the day seemed to really drag, until finally it was time to leave to go to Jenny’s house.
Tom popped his head round the door and asked if I was going to be around for tea and told him genuinely that I was going to be out visiting a mutual friend. Such is the trust between Tom and myself he never even asked who.

I arrived just a little before six pm and cautiously knocked on the door, Jenny quickly opened the door and bid me to enter. I was disappointed to see her wearing a light pink shell suit. My face must have betrayed me for she looked me in the face and then looked towards her feet and said “What?” I told her that her dress sense for the event about to unfold was appalling and that I bet she had the old school type knickers on beneath that nylon sweat suit. She chided me and scoffed that she did not wear that type of panties even when she was at school.

I beckoned her towards me and whispered that we had better go to her bedroom and get started. Like a child heading for the sweet shop she almost skipped up the stairs and indicated the door which led to her bedroom. I looked inside and asked to see the room next door and decided that this room being at the back of the house would be more suitable. The room also was better because it had more room sporting only a single bed. I then asked if she had a dining chair she could put in the space in the bedroom.

Jenny hurried down to the kitchen and returned with such a chair and I was delighted to see it was a dining chair with arms. I took Jenny’s trembling hand and led her back into her own bedroom. She looked confused until I said we need to collect a few things from here to use. I asked where she kept her tops and she showed me a couple of drawers and also the wardrobe. Quickly I selected a singlet top rather like a vest in white material; to this I gathered and added a short length wrap around pleated skirt. I looked Jenny full in the face and asked where she kept her sex toys; she blushed and said that she did not have any. “Bollocks!” I responded you‘re telling me that a 26 year old woman has not gathered a single vibrator or rubber cock to play with herself with.

Realising she had been caught, she apologised and went to a drawer where she withdrew a six inch but incredibly thin rubber vibrating cock and what I would have said was a large 8 inch wall decoration of a Welsh love spoon. The love spoon was one of those carved ornate wooden spoons which declared undying love between a Welsh male and female and the more ornate the spoon supposedly the deeper the love was meant to be. I looked at this last object and then looked carefully at Jenny questioningly and she again blushed even more as she said, she had used it as a paddle for spankings.

The way she said for spankings led me to believe that she had sampled it as well as used it on others. This made what she was going to go through even better from my point of view. I told Jenny, “Undress completely, then stand there with your feet eighteen inches apart, your hands behind your back and then turn your knees outwards. You may then wait for my further commands!”

Jenny began to say something until I announced that she had promised to obey my every word and besides had I not seen and felt her naked body when supposedly drunk she had entered my bedroom. She slowly began to unzip the shell suit and sure enough she had on a heavy duty bra and good solid panties; by good solid panties I mean those horrible sort of combo panties girdles which flattened the stomach area and made the arse look taut all the time. She stopped after removing the shell suit and began to take up her position until I reminded her sharply that I had said fully undressed and if I had to tell her once more then she would be heavily spanked and made to parade around in her own back garden for at least an hour totally nude.

She instantly knew that I meant business and a little embarrassed she undid her bra letting it fall to the floor and then stepped out of the panties before taking her stand. I had to adjust her feet to the required spacing I desired and I think she then found it difficult to point her knees outwards like I demanded, but her efforts whilst a little weak did do as I had intended as it caused her cunt lips to spread exposing her clit much more than if she had not moved her knees outwardly. I told her with practise she would achieve the angles of exposure that I was seeking and maybe she should practise this pose which I called the no.1 pose when she was alone.

I cleared my throat and announced that it was inspection time and that she should not move or say anything. This time I warned her there would be no second chances and if she failed this then she could expect to be punished in whatever way I saw fit. Now I knelt in front of Jenny and looked closely at her cunt, so closely in fact that I knew she could feel my hot breath on her cunt lips and I made it clear I could smell her aroused pussy. Having told her that her cunt was telling me by its aroma that she was a horny little whore I waited to see if she reacted before lightly touching her outer lips with my finger, this made her jump a little and I finally asked her if her cunt was twitching. She spoke nervously as she said it was not but she did feel something happening deep inside her. I smiled and suggested that was her anticipation building, that and the fact she had found her true calling as a whore eagerly expecting the favour of a cock to use her.

Standing back up I leaned close to her face and whispered that her cunt was telling me she loved cock and was eager to sample my own fine specimen. Just before I pulled away I stuck my tongue out and licked the tip of her nose, a startled jenny suddenly smiled and I scorned her that she had better stop grinning like a Cheshire cat or I would have to warm her rear with my hands. Walking around behind her I placed both hands on her arse cheeks in such a way that my index fingers touched at the tips and by crooking those fingers they crept into her anal crack close to her anal ring.

Leaning forward at the same time as widening the crack I was sure she could feel that same hot breath on her anal ring as it lay in full sight all puckered and slightly brown. I sensed rather than heard her catch her breath so squeezed her arse cheeks in my fingers and she instantly froze as if fearing that she had finally crossed the point of no return and about to be punished. Instead I simply stood up slowly allowing a path of my hot breath to travel upwards along her spine. Stepping closer I slipped my arms around her and located the soft tit flesh in the palms of my hands. With slow deliberate movements I located her hardening nipples between my forefingers and applied a little pressure. Instantly the half inch long nubs responded by becoming thicker and harder and as I twisted and tweaked them they responded further until they stood proud of her body like hat pegs.

Now I suddenly released them and walked back around the front of Jenny, I looked her over from head to toe and suddenly leaned forward and kissed her full on the mouth, I took her by surprise and it was not until I prised my tongue inside her lips that she responded. She stuck her tongue out to seek the inside of my mouth like I anticipated that she would and as soon as her tongue was clear of her lips I closed my lips around it and sucked hard bringing my teeth together at the same time to trap her tongue. I was surprised that she did not try to pull her tongue back until I released my grip and then she stood there eyes closed head tilted back slightly in preparation of a further kiss.

Instead I told her she could now put on the two items of clothing I had selected for her and she almost gasped her disappointment until I assume she realised that she would be spanked if I heard her do so. Now she slipped on the singlet top and quickly fastened her pleated skirt before waiting further instructions.

I led Jenny over to the dining chair and told her to sit but she had to sit with her backside on the edge of the chair and her arms laid flat along the chair arms, this meant that she was actually slouched in the seat but it was the ideal position for was happened next. I took from my flight bag some purple silk bondage ropes and tied her arms flat against the chair arms and once she could not move I told her that she was now going to learn the art of heightened anticipation. I ordered her to move her ankles back alongside the front legs of the chair and quickly tied them there; before tying a loop around her right knee and taking the rope behind her and round to the other side, there I pulled the rope tighter and tied off her left knee, the fact the rope was pulled tight had the effect of pulling her knees apart and exposing not only her cunt but because she was sat on the edge of the seat her anal ring also was available for my probing fingers or anything else for that matter.

I now stood up and standing in front of Jenny I slowly undressed talking to her as I removed each item of clothing until I was just wearing my boxer shorts and that was when I leaned forward and took the shoulder straps of the singlet and pulled it from her chest before allowing it to fall between her breasts. Now the stark white vest like top was in stark contrast to her flesh colour breasts with their dark red nipples still rock hard pointing out towards the ceiling. As I now removed my boxer shorts I told her to look closely at my cock and to get to like it because she and it were going to be very close friends.

I asked her if she liked my uncircumcised cock with its single eye peeping out from behind its foreskin and I asked if she could imagine how my cock tasted as it slipped into her perfectly formed oval lips and down towards the back of her throat. Jenny never replied but her eyes grew wide with desire and a quick feel up her skirt told me her cunt was bubbling away like a cauldron.

Now I flicked her skirt back exposing her thighs and the treasures between them became visible once more, her clit which had almost been invisible before was now striving to poke its head clear of its hood and her cunt lips lay open like the petals of a flower awaiting the arrival of a bee. I lightly traced my finger nail along her right thigh stopping just short of her eager cunt and I saw the look of lust flash through Jenny’s eyes.

Taking her own small vibrator I turned it on but was disappointed to find it no longer worked so I went back to my flight bag and retrieved a much larger version which when turned on buzzed like that expectant bee and that was only turned on low. At full speed I lightly traced a path along her left thigh up towards her cunt and then at the last minute I diverted the throbbing monster down to her butt cheeks and slowly over her anal ring before returning on a similar path down her right thigh. Jenny began trembling and I asked if it frightened her so much but she enthusiastically shook her head and gasped like an asthmatic it felt great.

Retracing the path now in reverse, this time I allowed the vibrator to rest against her anal ring for longer and even applied a little more force against the puckered entrance before moving it along her right thigh. On and on I continued each time remaining longer and longer against her anal ring and applying more firm; stronger pushes against it. I was mesmerized as I watched the puckered sphincter muscle slowly but surely give way to the intruding rubber cock and not an ounce of dissent from Jenny as she now rolled her eyes every time my rubber cock touched her anal ring.

Sensing the point at which the anal ring would finally allow the vibrator to enter I slipped a finger into her cunt just at that same moment and the shock of the sudden intrusion took her mind away from the steady progress the vibrator had made. Now the vibrator need not be held as the wall muscles of the colon took the strain. Jenny could not believe her ears as I told her that the vibrator was inside her anal ring, so I fetched a small hand held mirror and allowed her to see the solid tube of the vibrator sticking out of her arse and her cunt lips almost dripping its nectar juices on to the stem of the vibe.

Now leaning really close to her cunt, so close in fact my normal breathing was wafting warm air on to her clit, I slowly began to move the vibrator in and out of her clutching anal ring. As I sped up I then began nibbling her hard erect nub of her clitoris between my lips. As the pace increased so did the pressure on her clit and very soon Jenny was squirming like a worm on a hook. At this first sign of her becoming so horny as to be susceptible to further ideas I leaned back and asked if she now liked the idea of anal sex.

Almost through gritted teeth she gasped that she thought the way I did it was out of this world but pointed out that as yet I had not used my own erect cock; I smiled and then placed my forefinger at the entrance to her cunt and on the next out stroke of the vibrator I rammed my single finger into her cunt. I continued working her cunt and arse in unison as I added fingers to her cunt at regular periods until I had four fingers now spreading her cunt lips. Then as quickly as I could I fully withdrew the vibrator and fingers and replaced the rubber cock with my own real one. As soon as I was fully seated home with my balls against her arse cheeks I dropped my hand down and managed despite the lack of room to slip two fingers back into her cunt just as she began groaning out my name.

Releasing her cunt for the time being I began to rock to and fro making my cock slick mixture of her cunt and anal juices and then I asked her “what about now?” She looked me full in the face with wild eyes and grunted “Oh yes!” before panting for a few moments and then adding “I love the way you fuck my arse so much that anytime you want it, it is yours to have!”

Just as I settled into a steady rhythm of fucking her arse she suddenly sat bolt upright stretching the ropes which bound her arms and legs as her cunt spewed forth a cascade of juices like a waterfall. The hot sticky juice soaked our groin areas as she let out what can only be described as a gurgling sound. As she began to calm down she looked very red in the face and mumbled her apology for soaking me in her sweet sticky cunt juice, she confided that she had never cum so hard before and if that was a result of anal sex she was sorry she had missed out for so long. I told her that I considered it a great compliment to be the one to make her cum so hard and it proved that there was still life in the old dog anyway.

I looked down at her arms and was a little scared initially to see the red rings where her straining against the bindings had caused a rash but Jenny just smiled and whispered that they were badges of honour for her and she could not think of a better way to have earned them.

I quickly untied her arms and legs and had to help her into her own bedroom before she asked me to lie with her for a little while whilst she returned to her normal state. As we laid there she put her arms around my neck and kissed me on the forehead asking when we could repeat that fantastic episode. I looked a little puzzled because I had done all I set out to do and showed her that anal sex can be as much fun as any other sex if not more. Playfully she slapped my arm and teased me that she still had lots to learn and now I was her favourite teacher and just so I knew she was not going to let me off so lightly.

It just shows how strange things can work out; the girl who should have been my daughter in law was about to become my little whore at the drop of a hat. Or should that be drop of her clothing…

MVP6
01-20-2015, 02:07 PM
Loved your story and how it develped slowly.

comsmith22
05-01-2015, 04:27 PM
Nice development... Good story... Thanks for Sharing...