Jan 20, 2019

With Jane now in her late twenties, our adventurous lifestyle meant that we began to become rather more easily recognised – at least around our regular haunts - and my unusual preference of encouraging Jane to participate in casual sex with complete strangers, had led us - on occasions - to be recognised, and approached

This was not what I wanted – I preferred variety over repeat performances.

In order to achieve this, I began to organise her assignations to coincide with periods when we were away from home - with this in mind, I booked a series of static caravans, in various resorts (avoiding the school holidays), over the summer.

As we set off in early May, for the first of our weekend breaks - I told Jane that my intention was for her to provide sex for strangers as often as I could arrange - I reckoned that the anonymity of a strange town would allow both of us a little more freedom.

By now, she knew the score - and accepted that our weekends were very likely to consist of a perfectly normal lifestyle for eighty per cent of the time - interspersed with offering herself for casual sex during the other twenty per cent.

As always, I will attempt to describe the more unusual (and perhaps more erotic), encounters, while freely admitting that most of her partners were of the wham, bam, thank you Ma’am, variety.

Our first destination was Burnham on Sea, where I had hired a caravan for three nights of the Bank Holiday weekend – we arrived mid afternoon and settled into our new abode, before preparing for a night on the town.

We toured the local pubs and clubs but I drew an absolute blank - I found it impossible to manoeuvre myself into a position where I could discreetly offer Jane to any of the likely candidates that I had spotted.

By the time midnight arrived I had to admit defeat, and was almost resigned to postponing my pleasures until the following evening.

However I had one last strategy, and - disappointed and a little frustrated - I drove to the Bridgewater service station on the M5 - where I offered Jane to a Hungarian lorry driver.

He saved my day by having sex with her in his cab - thus allowing me to drive her back to our caravan and enjoy sloppy seconds. This was better than nothing - but not quite the work out for Jane that I had hoped for.

I told her that I had plans for something a little better before we returned home.

Saturday dawned and we spent the day strolling along the sands and taking in the views – two typical tourists enjoying a weekend break - who would have thought that the curly haired twenty-eight year old - in tight shorts and T-shirt - had ended the previous evening in the cab of a lorry – her ankles over the shoulders of a complete stranger, offering herself to a sweaty, middle aged Magyar for his sexual pleasure.

I would not have had her any other way.

We returned to our caravan where my mind immediately switched to the business that we had come here to complete - namely Jane providing sex for strangers with me enjoying the aftermath.

We walked up to our site’s club at around nine pm – the families with kids were beginning to disperse, and the entertainment was scheduled to kick off at 9.30. I got a couple of drinks and we sat back to enjoy the Roy Orbison tribute act – he was good - but his singing was not the only thing that I was assessing, as he performed on the small stage.

I told Jane that I would attempt to engage the singer in conversation – he was in his fifties and a little overweight – and would be offering her as his after show entertainment.

She nodded - knowing that, if all went according to my plan, she would be expected to offer herself, once again, for the sexual gratification of a complete stranger–only commenting that it had to be an improvement on last night’s lorry driver.

Between sets, I made my way to the bar where ‘Roy’ was sitting with a drink – I congratulated him on his act and asked if he was the regular performer at the club - he had doubtless heard this spiel a thousand times, and put on his professional smile, before replying that he toured all summer around the holiday resorts, returning to Burnham about once a month during the season.

As we chatted, he told me that he was given the use of a caravan - at the rear of the club - during his time in the resort, and would be moving on to Torquay, the following day.

I offered to buy him a drink and (as no one else was within earshot), made him an offer that wiped the bored expression clean off his face.

I handed him his vodka and orange and told him that my wife fancied him – and that, if he wanted, she would knock on his caravan door when he had finished his set - and that she would definitely let him fuck her.

He looked over at Jane and, I am sure, could not believe his luck – he said, ‘are you sure that you are all right with this’ – I answered that we were a broad minded couple and that Jane would do whatever he wanted.

He nodded and said ok and explained exactly where his caravan was – he said that it would be close to one a.m. before he got back - and she could turn up at any time after that.

I returned to our table to inform Jane of her duties for the night.

She accepted my suggestion, and agreed to give him what he wanted - but asked if she could have the following night off as she would have, by then, been fucked by two strangers - and she knew that I would also demand my share.

I said that I would think about it and told her that my decision would depend on how she performed tonight.

I need not have worried.

We returned to our caravan around midnight where we had a glass of wine and watched TV – I fancied fucking her, but as a matter of courtesy, refrained from messing up her pussy.

At just after one in the morning I sent her on her way, and turned in – I was asleep within minutes.

Some hours later (it was in fact 5.00am), I felt an arm encircle me and grab my shaft – I became hard in seconds as I realised that Jane had returned and silently got into bed – she whispered ‘do you want to hear what I have been doing, or would you prefer to go back to sleep’.

I told her to give me the details and continue working my dick.

She told me that she had walked the two hundred yards to his caravan and knocked on the door – he immediately opened it and invited her in with the words ‘I thought your hubby was having me on’ – she answered ‘this is what he likes me to do, so I do it to keep him happy’.

The singer asked her for more details, and Jane recounted some of her exploits - she reckons that hearing of her willingness to accommodate strangers turned him on, because without further ado, he took his dick out and asked Jane to suck it.

When she had got him to boiling point he took her through to the bedroom, where he asked her to lie face down, wearing only her stockings and suspenders – in this position, he climbed on top of her, fucked her, and made her provide anal sex.

Once he had finished they fell asleep – only for Jane to be woken some two hours later by ‘Roy’ demanding sex – as he fucked her for a second time, he insisted that she recount more details of her encounters – he got turned on by this, and withdrew from her pussy.

He once again lined up to sodomize her, - but this time Jane stopped him, saying that he would make her sore.

He paused - before telling her that if she would not do as he wanted, then she might as well return to her husband – Jane considered his statement for a while – agonising on how much I enjoyed her being fucked - before lowering her head and offering him her bare buttocks - he ignored her request for leniency, and obliged Jane to, once again, ‘take it up the arse’.

A couple of hours later she was woken and told to get on her knees, where he began to fuck her again – albeit, this time Jane insisted that he could not have anal sex.

He continued to ride her - almost to completion - before jumping off and pushing his dick into her mouth – he ejaculated almost immediately –massaging her neck as she swallowed his load.

He told her that he was done with her and that she could return to her husband – with his thanks – as he needed his sleep.

Jane got out of his bed and put on her light summer coat and shoes – she put her skirt and top over her handbag and - rather erotically I thought - walked gingerly back to our caravan wearing nothing under her coat other than her stockings and suspenders.

I fucked her, and told her that I rather liked his selfish usage of her – after all, she was not there for a romantic tryst - although I was a little miffed that he had enjoyed her arse to the extent that she was out of action, for this particular activity, for the remainder of our weekend.

Over all I felt our weekend away had been a success and looked forward with great anticipation to our next trip.

In fact our next two weekends away proved rather unremarkable – Jane offered herself, when asked, but my selections turned out to be rather mundane – she was had by three guys, but they simply fucked her as quickly as they could (one in our car, the other two in our caravan), and disappeared.

I had a bit more luck on our fourth trip away where I managed to unearth a dirty old man who, despite his age, managed to fuck Jane to a degree that she was forced to stand all evening, on our last night out.

We had booked a caravan just outside Skegness – where we had arrived late and I left Jane unpacking while I headed to the site club for a pint –I got talking to an old guy who owned a ‘van and spent all summer in the resort.

During the course of our conversation he admitted to being seventy-one and passed a comment (usually lewd), on every female that came within ten yards of us – slowly the obvious began to dawn on me, and I steered the conversation around to sex.

I reckon that I had hit on his favourite subject as he regaled me with his conquests and, more interestingly, what he liked to do with them – I encouraged him to open up and he was in full flow as Jane entered the room - looking for me.

I introduced her, and while the conversation became more mundane, his eyes – fixed on Jane’s bra-less breasts –suggested that his mind was still on our previous subject.

After a while he went for a pee and I took the opportunity to tell Jane that I wanted her, when he returned, to stand close up to him and encourage him to touch her up – before another twenty minutes had passed, his hand was permanently sliding up her thigh and, as soon as I left them for a couple of minutes, he propositioned her.

As I was returning, Jane caught my eye and nodded – this well rehearsed signal told me that she was prepared to be used for sex by whoever she was with, and that my presence was no longer useful.

I quietly left to enjoy a bottle of wine and watch TV.

I woke up next morning, alone.

Unusually, it seemed Jane had been required to perform all night - although my first thought was that perhaps she had been used by more than one guy, and that they had managed - by taking turns - to keep coming back for more.

I could not have been more wrong.

Jane returned around ten and her first words were, ‘You bastard, that old goat has fucked me raw’.

I could not help but laugh, as she limped under the shower and began to gingerly soap between her legs.

Jane told me that, after I had left them in the club, Harry (our new friend), had allowed his hands to increase their wandering – he was sitting at the corner of the bar with Jane facing him – as his conversation became more racy, he slid his hand underneath Jane’s blouse and massaged her breasts. Every time a customer approached the bar he quickly dropped his hand to her waist – this was interspersed with him sliding his hand (inserted between the folds of her split skirt), up her thigh. Jane reckoned that he had given her a thorough anatomical examination by the time they made to leave.

As they walked out of the club, he asked Jane to come to his caravan to take a look at some of his collection of artwork – this, unsurprisingly, turned out to be graphic pornography - but not something that was likely to shock Jane.

Jane accompanied him to his mobile home, and once inside he poured her a drink and asked her to draw the curtains as he went to dig out his ‘artwork’ – as she knelt on a seat and pulled together the last curtain, he grabbed her waist, raised her skirt – and fucked her.

This was the beginning of a long night for Jane, as she was repeatedly fucked, in every imaginable position, by this seemingly insatiable old lecher – he made her suck him and perform anal sex, – but he mainly - and endlessly - fucked her.

Jane believes, with the benefit of hindsight, that he must have had some form of artificial stimulus (I do not think that Viagra was available at this time, so it must remain a mystery), as he seemed to be permanently inside her – at one stage she pleaded with him that she was being fucked raw – in answer to which, he apologised, and began to sodomize her – she was soon fucked to a standstill.

There was no question of any further adventures (although he had asked her to return the following night), owing to the state that he had left her in. She spent the remainder of the weekend – standing - legs slightly apart - avoiding the eye of her septuagenarian stud.

I was pleased with the unusual aspects of this adventure and, I confess, surprised by the staying power of the old man – my only disappointment was that he had limited Jane’s activities to a one night stand.

Tags: anal, bareback, holiday