Jilly: Hot Choc & the Puppet Master

Jilly had been running a sort of guest house for nearly two years. She didn't need to do it but the money had come in handy and she'd been reasonably successful.

After the first six months of operation, she'd only had five or six clients (which was fine) but had decided to sign up with AirBnB. In truth, she hadn't really increased her turnover of guests but they were now a slightly more varied and interesting bunch.

Just before she'd started her B&B business, her boyfriend of the past ten or so years had arranged a meeting at a hotel for her, him and what he referred to as a BBC (Big, Black Cock.) The meeting had not been a success as the BBC; no doubt overwhelmed with the situation had been a little limp for a variety of reasons.

His name was Kenny but he went under the pseudonym 'Mr Chocolate Blue Eyez' (the name under which he modelled: His dark skin and ice-chip blue eyes made him look dangerous and he had vast experience at photoshoots.)

One of the many understandable reasons for the limited success was Jilly's insistence on the use of condoms (she had, understandably, refused to go bareback with a total stranger) but part of her had wondered if this relatively young, virile and well endowed man hadn't found her as attractive as her boyfriend clearly did.

Though she had dismissed the whole experience and attempted to banish it from her memory, it had continued to bother her more than she was willing to admit to herself or her boyfriend who had maintained contact with this 'BBC', occasionally promising him a 'rematch' and offering him some Viagra style pills to keep him hard for an entire night. Jilly was not keen but part of her, very deep down and well hidden, wanted the chance to prove herself, particularly as she now felt lean of body; empowered by a new eating and exercise regime and looking and feeling stronger than she had for a decade.

Her boyfriend had suggested, on many and numerous occasions, that they share another session but THIS time at her house where (he insisted) it would have a more relaxed atmosphere, they wouldn't be chased out of the rooms at cleaning time and crucially it wouldn't cost him any more money. Jilly was steadfast in her denial. There was no way she was allowing this particular 'BBC' over her threshold. He had, in her estimation, 'disrespected' her by not being available to fuck her all night.

Added to that, she didn't want him knowing where she lived.

To that, her boyfriend assured her quite accurately that he already knew her address and this proved (he insisted) that he was trustworthy and not a weird stalker-type.

In the past two months, her and her boyfriend had tried a 'multiple partner' session and had enjoyed a very satisfying foursome with two hugely impressive guys and she was now waiting for another opportunity to experience something like that again.

Meanwhile, by way of a 'thank you' her boyfriend had been plying her with gifts of clothes and she was happily strutting around the town in her latest presents whenever she could.

When the gifts arrived, her boyfriend would always follow up with a slightly controlling message that read something like, 'I've bought you all this stuff. I own you, you know that, right?'

The last time they'd met, he'd once again suggested that they rekindle their BBC interest with Kenny and invite him to her home. Again, she'd pushed back strongly and said that she wouldn't want a stranger in his house.

"You have strangers in your house all the time!"

"What do you mean?"

"AirBnB! Those people are complete strangers and..."

There was silence for a moment as they stared at each other.

"Okay. Never mind. Forget it."

He didn't seem stroppy or upset. He had just decided, it seemed, to suddenly lose interest.

The subject was dropped and they ventured upstairs to make love.

Their relationship was complicated and yet simple. They met for sex but the interplay between them was deep and based on an intimate understanding. He wanted to control her and, weirdly for someone so strong, she wanted to be controlled. He bought her clothes and had, a few months' previously, had a CCTV camera installed in her bedroom so that he could observe her at any time of the day. Rather than finding this intrusive and creepy, she found it comforting and flattering.

During their love-making, he would make sure to get the best angles in relation to the camera for his viewing pleasure later on.

Day One - Jilly

A few days later, I was checking my emails when my inbox 'pinged' to signify a message had arrived. It was from AirBnB to say that a potential guest had made an enquiry. I clicked on the link and my eyes widened. There, staring at me from the screen was Kenny; Mr Chocolate Blue Eyez. He was enquiring as to the availability of my room this coming Friday.

'Hi

I am going to a work's 'do' on Friday and wanted to hopefully leave work, find somewhere nice to stay (to shower and get cleaned up) before venturing in to town and then not having to catch a late night bus home (or worse, walk!)

Your place looks perfect and though it's a little above my budget, I thought I may as well treat myself as it's also my birthday soon!

I hope you can fit me in.

Yours

Ken'

I stared at the screen; ideas racing through my head; trying to figure out what this was.

It could be genuine, I pondered. Perhaps he had no idea who I was and he simply wanted to rent the room exactly as he'd described.

Alternatively, (and more likely, I thought) he knew exactly who I was and wanted to finally find his way back into close proximity (and why wouldn't he? I was feeling and looking amazing these days!)

Then suddenly it struck me. This was my boyfriend's idea of a joke. He was impersonating him and trying to wind me up. This had his fingerprints all over it, in fact. He had often played practical jokes on me and I started to relax and then started to giggle a little. He was incorrigible.

So I decided to play along.

Dear 'Ken'

Yes, the room is free that night and you're in luck as I'm happy to offer you a half price reduction provided you're willing to dispense with breakfast. And as a goodwill gesture (seeing as it's your birthday soon!) I'm perfectly willing to tuck you in! Ha ha ha

I look forward to receiving your 'confirmation' soon.

Regards

Jilly

I re-read it twice and, satisfied that this was in fact NOT someone called Kenny but my mischievous boyfriend, pressed 'send.'

No reply came and I went to bed and slept a little fitfully.

Day One - The Puppet Master.

Ken and I had been in fairly constant contact over the past weeks. I had insisted to him that I was working on a plan and just needed the right opportunity. I even said that I 'guaranteed' that he'd be fucking our MILF before the year was out.

"Those are brave words!" Ken had written back.

"But I look forward to laying my hands on the bitch again soon. From the pictures and videos of her from her bedroom (how the fuck did you persuade her to have CCTV put in her room?) she's looking fit, toned and ready to experience some Ken magic!!"

But the email I finally had sent to her was without Ken's consent. All I knew was that Ken was free this coming Friday night and I had told Ken to keep it that way.

"I have a plan, my man!"

My email was polite and direct and I was grinning as I composed it on behalf of my living and breathing 'friend'.

Her reply was a little surprising but showed that she believed me to be posing as Ken. That was fine. I half expected an email from her (directly to my personal inbox) telling me what a great joke it was but none came. So I decided to wait before sending a reply on Ken's behalf to let her stew.

However, a few hours later, I sent an email directly from me making no mention of it (of course) and instead focussing on my plans for her and me in the future AND alluding to the fact that I was unavailable this coming weekend.

Hopefully, she would perhaps start to worry just a little.

Day Two - Jilly

Later the next day came the reply.

Hi Jilly

Wow! I don't really know what to say! That's incredibly generous. Though I'm disappointed not to get the breakfast (all the reviews say it is one of the main reasons to stay!) I'm delighted with the reduction in price as I was struggling to justify it to myself.

Tucking me in will be a bonus but I'm sure that was a joke (though I may still hold you to it! LOL!)

Please book me in. I'll be arriving just after 6pm on Friday.

Regards

Ken

ps. Can I please check the house rules with regard to a last-minute, additional guest? I'd rather know in advance.

I stared at this and re-read it several times. My stomach started to cramp a little as I began to consider that this was in fact NOT my boyfriend. Could it actually be genuine?

"Oh fuck!" I said out loud.

I considered what to do next. I could make up an excuse and cancel but I was a stickler for the rules and as the room had said 'available' online, I felt I couldn't just suddenly make it unavailable. Alternatively, I could let it play out.

I decided to contact my boyfriend and ask him outright.

I wrote a terse and direct email telling him that the joke had gone far enough.

His reply (as always) was fairly instantaneous.

"I don't know what you're talking about. I haven't spoken to Ken for weeks. And what joke?"

"Oh fuck!" I said out loud again and I couldn't help but be a little cross with him as it was him who'd made the introductions in the first place.

I spent the rest of the day pondering my predicament and after much consideration, decided I would have to let it play out. I would be the perfect hostess but promised myself that I wouldn't lead him on, so decided to 'dress down' as opposed to dressing to impress.

I smirked to myself.

The very fact I was thinking about it meant I'd probably end up doing exactly the opposite ESPECIALLY if my boyfriend became involved now that I'd told him what was happening.

I wrote back.

Dear Ken

I'm looking forward to hosting you.

The house rules are fairly strict I'm afraid so if you 'get lucky' on your night out, you may have to make other arrangements. But thank you for being so considerate in asking! Most people wouldn't bother.

Perhaps, if you have had to say goodnight to someone for whom you had 'bedroom plans', me tucking you in would be a mistake! Ha ha. (and yes, it was a joke!)

I attach the link for payment.

See you after 6pm on Friday.

Yours,

Jilly.

Within 15 minutes, I had confirmation of payment. The die had been cast.

Day Two - The Puppet Master.

My reply on behalf of Ken (I felt) was perfectly weighted; striking the perfect balance of light -hearted flirtatiousness as well as stating 'Ken's' intention to bring someone back with him given half a chance.

I knew her so well that these statements would make her 'up' her game and think, 'how dare he (Ken) think about bringing someone back to my house when I'm the most attractive woman he'll meet, period!'

I knew that she'd now be mentally running through what to wear and how to act to show Ken that she was the only woman worth fucking even though she'd deny it.

Within a few minutes, my own, personal email account was buzzing with indignation and a little panic.

Dear Boyfriend

Okay. The joke's gone far enough. I know you're posing as 'Kenny/Chocolate'. Enough is enough. I have a good mind to book it in and make you pay!!

Yours (annoyed but still desperate to see you!)

Jilly

I read it and laughed out loud at her obvious panic. Before I replied, I tried to consider all the angles and what her true concerns were should this scenario actually be genuine (which I hoped it soon would be!)

I wrote back, denying all knowledge and asked her to explain what was going on.

Dear Boyfriend.

Out of the blue yesterday, someone called Kenny contacted me. His profile picture was...him! The one we had our threesome with! Fuck!!

He wanted to book the room in my house as he has a work's 'do'. He didn't allude to knowing who I was and I assumed it was you playing a joke but it would appear not! WTF?

What should I do? I've said all along I don't want him in the house and now...!

I'll have to think what to do. I suppose I can say I'm going away suddenly. I don't know.

x

I wrote back, trying to force the last piece of the jigsaw in place.

Dear Jilly

Firstly, Ken's a really good lad. I've always said so, haven't I?

From what you've said, he just doesn't want to have to schlep all the way home after work to then come back into town and then have to get a night bus home. My guess that he doesn't even know that it's you.

Having said that, can you imagine his face when you open the door in some fantastically short skirt and high heels and show him to his room? Delicious doesn't really cover it!! In fact, you look so fucking hot at the moment that he'll probably pass on the work's 'do' and say he just fancies a night in!

And if you look as stunning as you always do, he will definitely be wanting to make a midnight visit to you to show his appreciation for the half price room!! (I can't believe you of all people suggested that! Unless, subconsciously you WANTED him to have an excuse to book!)

I think you should let him come and stay. You never know, you might end up urging him to try a different bed!!

I wish I could stay too so that we could have an all-night threesome but I'm, unfortunately, tied up.

Take care (and 'let the poor boy in,' is my advice!)

x

Within an hour, 'Ken' received the email confirming the booking.

I wrote an email informing Ken that he would finally have sole access to Jilly. All he needed to do was be impressive as a person...and in the sack!

Dear Ken,

The deal is done. She is going to be expecting you after work on Friday after 6pm. I've paid for the room already.

Make sure you are charming. Chat her up good and proper. If you want to maintain the cover story, go out for a couple of hours but don't get tanked up. But you'll need your wits about you and be able to think on your feet. If you get it right, you'll be taking her through the night and if you REALLY get it right, a return match (or several) is a guarantee.

Lastly, I will leave an envelope for you by her front gate (behind it so it can't be seen from the road.) In it, you'll find a little blue pill or two. That should be enough to keep you hard for most of the night!! When/if you gain access to her, give her one from me!! Ha ha ha

Over the next few hours, I sent a series of emails detailing her penchants, her likes and her dislikes. I fed him some lines and told him how I thought it would go and to be ready for this or that. I told him very intimate secrets of what turned her on and how to fine tune it.

By the time I'd finished, I hoped he had a fail-safe guidebook to seduce and fuck my MILF mistress.

Day Two - Ken

So my 'mate' sorted me out a night with the filthy MILF!

I appreciated that because I really wanted to get some one-on-one with her as I remembered her fantastic fucking curves from last time and THIS time I wanted to dip and dip and fuck and fuck.

I knew that once she sampled my cock, she'd find it hard to get fucked by anyone else ESPECIALLY her poor excuse of a boyfriend.

I decided to play it just the way he said I should...up to a point. Then I'd do some improvising. Or maybe try some planning of my own.

Friday - Jilly

My boyfriend, having now heard the entire story first hand was excited on my behalf and insisted on coming to see me on the Friday morning for a calming fuck, sandwiched between two pep talks (though I seem to remember him saying he wasn't available!)

"So, be cool but not too cool. If you play it right, he'll be sliding himself into your bed in the middle of the night and wanting to bang you rigid. Remember, I'll be watching for signs of life!" He said, pointing at the camera.

"But I'm not sure I want him sliding into my bed!" I said protesting.

He waved the thought away almost not hearing it.

"What are you going to be wearing?" He asked.

"Oh! I haven't even thought about it. I'm trying to be the perfect host!"

"You'll be the perfect host by dressing like a total fucking tart!"

He strode to my wardrobe and started rifling through.

"Okay. This, this, these and no knickers. A bra is optional if you think it'll help!"

He'd laid out a tiny leather skirt, a tight, white, ribbed vest top and a pair of black high heeled platform boots. Hardly appropriate hosting gear. I ventured. Again, my protestations were waved away but he turned earnestly.

"Remember, if you need guidance on what to do, email me, text me, FaceTime me. Whatever. I have a sixth sense on these things and will always guide you right, okay?"

Unusually, he then asked if I would make him a green tea. He had to use the bathroom and wanted also to check Ken's room. He picked up his rucksack and took it with him. I thought no more of it. I made tea.

When he came down he was clutching a small camera similar to the one in my bedroom.

"I bought you another one for additional security the next time you're away."

He placed it on a shelf above the main cooking area. He spent a few minutes pairing it and seeing that the angles were right via his smart phone.

We chatted some more and then kissed passionately and I ached to feel him inside me again but there was no time. I had things to do.

With a last kiss and a desperate hand on the lump in his trousers, I let him go.

Friday - the Puppet Master.

I was due to arrive mid morning.

Though I'd carefully orchestrated everything that was about to happen today, I couldn't help but feel more than a little jealous that my 'buddy' was about to spend the night with my MILF; to do with her (more or less) as he pleased.

Before I strode to her door, I deposited the envelope which I'd enclosed in a waterproof pocket behind the gate out of sight of the road and out of sight of a casual glance from the house. In it were two blue pills. With these blue wonder-pills, Ken had a four to six hour window of opportunity per pill (provided there was sexual attraction.) Ken would be hard and ready for most of the night and more.

My cock was almost sore at the thought of a 12 hour marathon but twitched at the thought of her bare pussy's wet, puffy lips inviting a hard cock to bury itself within her.

Once I was in the door, we kissed deeply and my cock was instantly hard. We broke away.

"So, are you excited?"

"I'm nervous. I have no idea what to expect. He may find me hideous and not even know who I am!"

I chose my words carefully as I was aware that Ken knew exactly who she was and what he would get if he played his cards right.

"Look. I think you have to take this at face value. He's booked the room and may not know who you are. If he recognises you, it's then up to you. It'll be a game of chess!! But looking at you now, he'll definitely want to fuck you. He'd be mad not to want to!"

I gave her a few pointers and signs to look out for before taking her upstairs, stripping her naked and - after making her cum with my tongue and mouth - fucked her quick and hard, the wetness from her pussy making sucking noises as I pumped into her at differing angles. I came inside her and fell onto her, breathing heavily.

"Oh fuck! Your pussy never ceases to amaze me, you fucking sexy bitch!"

We lay there for a few minutes before we got up in unison and went to the shower together and tenderly soaped one another, kissing as we went.

Unbelievably, I was hard again and managed to slide my cock into her from behind. She came again (with her, once the first orgasm was achieved, they then arrived like a rolling tide.) I kept ploughing on but knew that I had to be somewhere so once she had cum a fourth time, I reluctantly stopped, pulled out and soaped my cock, urging her not to touch it as I'd have had to fuck her again!! She giggled but obeyed.