23 Oct 2018

As time went by, and Jane came to accept my instructions without question - I stretched my imagination, and made her available in increasingly erotic situations.

For some reason I enjoyed having her provide sex to old men - sometimes ugly and overweight, or Asian waiters - or lorry drivers in their cabs.

She baulked occasionally at my choices, but, after a few reassuring words from me, she always allowed me to pimp her out.

The next opportunity for me to offer Jane for sex occurred on a winter holiday to the Canaries.

Jane was now well into her twenties and nothing I suggested surprised her – so, when I told her that I was going to have her fucked before we returned home - and that I would offer her for sex at the next opportunity – she resigned herself to whatever I might come up with.

I had a guy in mind - but I was keen to engineer a situation that would provide me with maximum pleasure.

We had come to know one of the owners on the complex over a period of years – he was just what I was looking for. He was in his sixties, loud, overweight and always letting everyone know how well he did with women.

Of course, this had to be all bluster and brag – he was old, ugly, and often well oiled – nevertheless, I wanted Jane to offer him sex - and to let him know that if he wished to debase her, she would comply.

One early evening I seized my opportunity – we were the only customers in the bar and the Spanish bar girl was preparing food.

I asked him ‘how is your love life these days, Frank?’ to which he replied, in his usual self satisfied way, ‘couldn’t be better – this is the place for picking up women’.

I shrugged and said ‘You’re the lucky one – you know all the spots on the island’.

I then fed him a story about how I had to go up to the north of the island the following day - and this meant that I had to let Jane down - as I had promised to take her out for dinner.

His eyes almost popped out when I suggested he take my place - as a big favour to me.

We arranged for Jane to call at his apartment the following evening - and he would take her out with my blessing - and at the same time, get me out of a tight spot.

I returned to our apartment, where Jane was catching the last rays on the balcony. She was face down on a towel, wearing a bikini – I lay on top of her - pulled her bikini bottoms to one side - penetrated her - and told her the news.

She let me have my way before saying, ‘you are becoming a dirty old pervert’, to which I replied that I had always been a pervert, and it would be at least a further twenty years before I became an ‘old’ pervert.

I told her that she would be calling on him at eight o clock, and that I wanted her to turn up without underwear, in a light summer frock and with her pussy freshly shaved.

Next evening she prepared herself according to my instructions and - just prior to her leaving; I lifted her dress and inspected the goods.

I told her to let him take whatever he wanted and make absolutely sure that she gave him anal sex – I always preferred her to include anal when I offered her to anyone – it just seemed to make her subjugation complete.

She returned at three in the morning, and I sat up in bed yawning - and expectantly awaiting details.

As she pulled her dress over her head she said ‘you will be pleased to know that Frank is as much of a pervert as you are’.

I was delighted to hear this - and told her to kneel on the bed in order for me to inspect the damage.

I could see immediately that she had been used for anal sex, but her pussy also seemed distended.

I asked her how she had managed this, to which she replied, ‘he fucked me with a strap on when he could not get hard –I cannot take any more tonight, so you will just have to let me suck you’.

I allowed her to suck and swallow it all, before I lay back and asked her for details of her night out.

Frank had taken her to a restaurant, where he was well known – he was all puffed up to be out with a young, attractive woman, and made sure that he seen by as many people as possible.

Following their meal, Frank took her back to the apartments in a taxi – on arrival he asked her in for a nightcap - hoping, I am sure, to try his luck.

Jane, of course, was well aware of why I had sent her - and accepted his offer.

Once inside, with a drink and a little music, Frank began a slow smoochie dance with her – he soon progressed to gently massaging her breasts and, finding no resistance, he slid his horny hand up the inside of her thigh.

He let out a groan as he discovered that she had no underwear and a shaven pussy - and continued to stroke her intimately.

Jane opened her legs slightly in order to allow him better access - and also to confirm that she was available.

He asked her to kneel down and performed oral sex – Jane was now ready to do whatever he required - but here the problems began.

Frank, for all his talk, could not get hard – Jane listened as he apologised and blustered - before she decided to take the initiative – she said, ‘you can have my arse if you like’ - at which news, Frank immediately managed an erection.

He quickly buggered her, and as Jane threw back her head and groaned - he penetrated to the hilt - and ejaculated.

The great Lothario was profuse in his apologies for his five second performance - and began to perform oral sex – Jane relaxed and after a couple of minutes felt him stretch open her pussy and begin to insert a large object.

The object proved to be a strap on penis, that Frank obviously needed to help him out - He fucked her with the strap on giving Jane complete satisfaction – she eventually said she was exhausted, and could take no more – she kissed him and thanked him for giving her so much pleasure.

Frank withdrew the bottle and knelt behind her – he once again, slid his dick up her arse, and once again, ejaculated as she let out a groan in response to the intrusion.

His two performances lasted a total of ten seconds, but oddly, both parties finished well satisfied with their night’s foray.

He begged to see her again, but Jane told him that she had to have my permission before she was allowed to go with other men.

On hearing this, she thought that Frank, rightly, suspected that I orchestrated her availability for sex, because he then suggested his own plans, no doubt intending her to pass his suggestions on to me – and possibly allow another meeting.

On hearing this, I told her to hang on until the following day before giving me the full details of his suggestion – I wanted to be fucking her as she told me - just in case I decided to insist on her carrying out his request.

As it transpired I was interested - and Jane was, very nearly, despatched, three days later - to provide both Frank and a friend with some very adult entertainment.

His suggestion, as relayed to me the next day, was for Jane to accompany him to a friend’s villa in the hills – he promised that she would be spoiled for choice, with drink and hard core porn movies - to enhance her sexual enjoyment.

He said that he and his friend, who was some years older than him, wished to watch her having sex with a young man - and perhaps have her themselves afterwards.

Jane was a little wary of this suggestion and asked for details of the ‘young man’ – Frank told her that he was a well endowed African boy, who would be paid for his time – all she had to do was to allow him to use her for sex.

I have to admit that I fancied this, and I have no doubt that Jane would have gone if I had instructed her - however, after some deliberation - I told her to inform Frank that I was not prepared to give her permission to accompany him.

Over subsequent years, I have often regretted not sending her – I am sure it would have been a fascinating addition to my memoirs.

On our return to the UK our lives continued as before, that is, in a very relaxed and hedonistic fashion – before long, however, I felt the urge to offer Jane for the enjoyment of another stranger.

My opportunity presented itself after we had dined out in an Indian restaurant – owing to a split skirt; Jane had displayed her stocking tops to most of the customers - and all of the waiting staff - before the second course.

Over a final glass of wine I told Jane that I intended to have her fucked.

I told her that I would attend to the bill and that I wanted her to go and sit in the car - which was parked behind the restaurant - and await company.

She left and I called over a waiter – I asked him for the bill and, when he returned to the table, I told him that Jane was in a Ford Focus in the car park, and she wanted him to go out to her – if he did, she would let him fuck her.

He stared at me for a couple of seconds, not sure if I was serious or not – I told him that the offer was genuine - whereupon he left the room at the speed of light.

I sat, sipping my wine, and waited.

Fifteen minutes later the waiter reappeared and carried on with his duties – I stood up and left the restaurant - rejoining Jane in the car.

I got in on the passenger side - reclined the seat that she was sitting in - lifted her skirt - and mounted her.

She was sloppy and had obviously just finished with the waiter - but I asked her for confirmation.

She told me, that a few minutes after getting in the car, she saw a waiter, almost running across the car park and looking around frantically – she caught his eye and nodded - at which the young guy ran over to the car – almost pulled Jane out – bent her over the bonnet, and fucked her furiously.

In just a few minutes he was done - at which he simply pulled her skirt down over her bare buttocks - and walked back into the restaurant.

I found this highly erotic and, as was my wont, added my contribution to that of the waiter.

I fucked her repeatedly throughout the next couple of days – and told her that I would expect her to tip the waiting staff, in this identical way, on future occasions.

Tags: anal, strapon