Riley’s Island Diary! By Tina Majors

Riley’s Island Diary!

By Tina Majors

© 2019-2050 QoS Comix All Rights Reserved
No part of this publication may be reproduced, distributed or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law. For permission requests, email to Devinwhitegurl@gmail.com

This is a work of fiction. Names, characters, places, and incidents are a product of the author’s imagination. Locales and public names are sometimes used for atmospheric purposes. Any resemblance to actual people, living or dead, or to businesses, companies, events, institutions, or locales is completely coincidental.

**DEVIN DICKIE NOTE**
All characters are OVER 18 years of AGE! This is a bullying fantasy and not real. The acts in the following written work are only consensual sexual choices and fantasy humiliation scenarios.
Bullying is NOT OKAY and If you or someone you know is being bullied, please

alert the authorities.

Riley’s Island Diary!

By Tina Majors

JUNE 5th

So, here I am, starting another diary with all the good intentions in the world. Sure, this time I’ll keep it up, definitely... probably... maybe update it every day with every single bit of minutiae from my day-to-day life here on this fabulous little island.

Well, maybe not so little.

Seriously though, I’ve started so many of these damn diaries over the years, and I only ever get a few days in before I give up. I guess that’s probably down to one main reason... my life just isn’t that interesting.

I mean, I study hard, I like to party sometimes, but other than that my existence is pretty conventional. It’s not that I don’t want to do or see interesting things, I guess it just I never seem to be in the right place at the right time to catch that seriously juicy, dangerous kind of action that always seems to happen to everyone else but never me.

Well, whatever.
Maybe this summer will be different.
I’ve only been back from NYU for a couple of weeks and

I’m already bored. I graduated strongly, pretty much in the top one percent of my class, but the idea of going straight into a job just didn’t do it for me.

To be honest, I’d worked so hard in that final semester that I was in real danger of burning out. I’d seen my older sister go straight into some ultra-competitive law career and knew I didn’t want to end up like her, totally lost in her work, her lived experience as narrow and work oriented as you could get.

So, rather than follow up on those graduate offers in the city, I decided to head home to my island paradise and take as many weeks, or months, as I needed to rest and recuperate. My plan is very much to take it exactly as easy as I need to take it.

Beach.
My parents’ pool.
Maybe take my cycle out for a spin.
Simply relax and take it all in for once.
And if I happen to meet a cute guy? Well, dating’s not out

of the question either. I did have a bit of a holiday romance last summer with a local boy called Malik who worked at the boat yard where my dad kept his yacht. Malik was a couple of years younger than me, but even at nineteen was definitely all man...

Like nearly all holiday romances, things kind of fizzled out when I went back to New York. But now I am back, who knows? Which reminds me, I need to make sure that all my bikinis

still fit. As well as studying like a beast, I’ve also been working out like a maniac, the effect being that my waist has shrunk, but my booty has grown... not that any of the island guys will be complaining on that front I’m sure.

So, there we go.
Entry number one done and dusted.
Now it’s time to strip off, sort through these bikinis and

maybe even try an evening dip in the pool.

Until next time XoXo.

JUNE 10th

Wow. So, it turns out that my mom and dad’s friends maybe aren’t quite as boring as I’d always thought. At least not all of them, anyhow. A couple of nights ago I was making myself a late-night grilled tofu and veg kebab and ended up overhearing what I could only describe as a very interesting conversation between my mom and Kelly.

I’d never met Kelly before, only heard about her via my parents. Kelly and her husband Rick had moved to the island a few months ago. They were in their late twenties, maybe even early thirties, but had apparently lucked out on Bitcoin to such an extent that they had enough money to quit their city jobs, buy one of the super-lux new houses in the development further up the hill from my parents’ house, and still have enough money to live like kings - and queens - for the rest of their lives.

Lucky for some, right?

Anyway, as I was waiting for the oven timer to go off, I popped my head around the corner and watched as Kelly demonstrated some kind of TikTok dance for my mom. Sure, it was funny to witness my mom try to grasp dance moves, but what really caught my eye was Kelly.

She was probably only about 5’4” but her body was absolutely something else. She had the kind of

breast-waist-hips ratio that if you saw a photo of online, you’d assume had been more than a little bit touched up on Photoshop. We’re talking Kardashian-esque proportions. With her dark brown hair, plump lips and sparkling blue eyes, I found myself transfixed by her pretty much instantly.

I’d had my fair few girl-crushes while at college, but this was something else. It was like she had been designed in a computer or something.

As Kelly continued to dance, being extremely patient with my mom who just couldn’t pick up the moves, I was pretty much drooling at the sight of her huge breasts bouncing up and down and side to side, her yellow vest struggling to hold them in by the looks of things.

At this point, I could only imagine what Rick was going to look like. If Kelly was anything to go by, I was expecting someone tall, tanned, and incredibly handsome. Probably a Hemsworth brother type, someone with the kind of washboard stomach and gym-honed body that would complement her simply spectacular curves.

Then, just as Kelly went into a cocktail-fuelled improvised twerk, I heard my dad’s voice, accompanied by another male voice, walking up from the basement cinema room and into the kitchen.

Wait, that couldn’t be... Rick?

Could it?

As my dad introduced me to the 5’3”, pale, sandy-haired Rick, I found myself scanning him up and down in much the same way I had just been doing to Kelly. Except this time, I wasn’t doing it out of lust.

Quite the opposite.

In fact, it was difficult to not let out a little giggle as I sized up Rick’s puny looking body and actually pretty feminine booty poking out, a perfect bubble at the back of his pale pink chino shorts.

So, yeah, Rick and Kelly were definitely a bit of an odd couple as far as I could see. Still, with over twenty million dollars in assets, I don’t suppose they care much what an unemployed graduate like me thought of them.

Just as my dad and Rick walked out of the kitchen to meet their wives for more cocktails, my dad stopped and turned around to look at me.

“Oh, hey, Riley,” he said, his silver hair looking as sharp as always. “Rick has very kindly said you can have some shifts at his and Kelly’s new café. Isn’t that kind?”

My dad had built his business up from scratch before retiring early to the island, and to say he was keen on work ethic was an understatement. I could tell that this wasn’t a job offer as far as my dad was concerned, it was mandatory if I wanted to stay living rent free at home. Essentially, whether my plan was months and months of indefinite relaxation or not, I

had to take Rick and Kelly up on working in the café, even if it was only a couple of shifts a week.

But, hey, it’s not all bad news.

If it means I’m working with Kelly and her magnificent titties and TikTok dances, then I guess there’s worse ways to spend the summer, right?

JUNE 20th

Finally, a chance to write...

Okay, so my first few shifts at Rick and Kelly’s café were kind of to be expected. Basically, I was front of house, serving up iced lattes and green smoothies to tourists, and the occasional local.

It wasn’t taxing work, it wasn’t remotely exciting, but I kind of enjoyed it. After all, it was my choice to delay getting started on a proper career, and if I could earn a few bucks and keep my dad off my back, then it was all good.

I soon got the hang of my duties and the odd fussy customer aside, it was plain sailing. Which brings me up to today. I was doing the evening shift, the 9PM close, and Rick had been out all day on a run to the fruit wholesaler on the other side of the island. Kelly had been popping in and out to check on me, but pretty much leaving me to my own devices.

Then, disaster.

The Apple Pay machine stopped working just as a big group of tourists came in, each and every one of them sweating and ready for one of our iced refresher juices. I apologised for

the delay and told them I would be back in a second, just as soon as I located my boss.

Fortunately, Kelly happened to be outside, sitting and chatting with her friend. As I was about to call out to her, I caught a hint of what they were saying and just had to pause and listen for a moment...

“You know, me and Jerry have an understanding,” the friend said, looking glamorous, gym-fit, probably in her early forties. “I don’t ask what he gets up to on his business trips to LA, he doesn’t enquire about my... one on one scuba sessions.”

I could see that Kelly was shocked by what she was hearing, but she was definitely listening pretty intently.

“I don’t know, it just sounds...” Kelly said, stopping as she caught me in the corner of her eye, standing there patiently but also desperate to hear more. “Oh, hey, Riley. All okay?”

I explained what was up and Kelly managed to get the payment machine back online in no time. After the shift was finished, she approached me, clearly a little concerned about what she thought I might have heard.

“You know, Merrill is kind of wild,” Kelly said, laughing, her body still more than capable of hypnotising me. “I know you heard what she was talking about, but just to clarify, it’s definitely not my scene personally. No judgements, just not my thing.”

“Oh, right, cool, whatever,” I said, trying to sound casual, and actually more excited about the fact that Kelly was talking to me as if I was a friend rather than just her employee. “I guess whatever works for the individual, right?”

Kelly smiled, something definitely going on behind her eyes as we finished closing up for the night, the process really not much more than wiping the tables down and making sure that the dish washer was filled up and turned on.

“I’m actually going out for a few drinks with Merrill and some of my other girlfriends tonight,” Kelly said, looking at her phone. “If you see us out, feel free to come over and have a drink. You know, a little bonus for settling in and doing so well.”

I blushed a little, taken aback that my girl crush seemed to be extending the hand of friendship. Unfortunately, I had already agreed to meet Malik, my boyfriend from last summer, for a drink and friendly catch-up. Kelly didn’t seem to mind though and said if I didn’t see her that evening, there would be plenty of other opportunities.

Well, it was nice to actually see Malik again. I don’t know what will happen between us, but we definitely still have a connection, that’s for sure. He’s actually grown another couple of inches, and by the looks of things has been spending a lot more time down at the gym, his lean frame now filling out and looking pretty damn buffed up.

Anyway, on the walk home from our date, I noticed Kelly and her girlfriends sitting outside a new café-bar, the drinks evidently in full flow if their loud, raucous laughter was anything to go by.

I suddenly came over a little shy though, probably due to the fact it was a group of inebriated and loud women I didn’t know, and rather than approach them I kind of casually grabbed a table nearby and decided to listen in for a moment...

“Girls, you’re just too outrageous!” Kelly said, her voice definitely giving away the fact she was at least four drinks in. “Rick isn’t even that small... you know... four inches is pretty much average, right?”

I struggled not to laugh.
I mean, was she being serious?
Even I knew that four inches was tiny, and so did Kelly’s

friends by the sounds of it...
“Kelly, Jesus, you don’t know what the hell it is you’re

missing,” Merrill said, nudging the tall, busty women next to her. “I think what you need is to open your eyes a little. Have a look around. I mean, check him out for example. You can see exactly what he’s got going on, and it’s at least two and a half times what Rick has, let’s put it that way.”

The guy they were looking at was a local. Dark skin, perfectly braided hair, well over six feet, and with a lean,

muscular physique that seemed to draw attention to the long, snake-like shape at the front of his white shorts.

I glanced at Kelly and saw her blushing.

“Go on, go and say hi to him,” Merrill said. “You know, just to show you’re not one of these arrogant newcomers who think they’re too good for the islanders.”

Taking Merrill’s bait, and totally to my surprise, I watched as Kelly got up from her seat and walked over to the man as he waited patiently for his takeaway box of the bar’s famous lemon fried fish. The man was clearly pleased to see Kelly approach, her breasts looking tanned, soft, and very much on display.

It was crazy to witness, but right before my eyes I watched as the conversation deepened, all the body language between the two of them screaming attraction until... Kelly leaned in and kissed the man full on the lips.

Blushing furiously, Kelly pulled away and walked back to the table of her girlfriends, their laughter and cheers giving me the perfect opportunity to sneak away without being spotted. The last thing I wanted was for Kelly to know that I’d witnessed her kiss another man.

So... I definitely have to keep this to myself.

But, on the other hand, I’ll be keeping my eyes and ears peeled from now on to see whether this was just a one-off, or something else entirely.

JULY 27th

OMG.
OMG.
O. M. G!
Kelly told me to go to the fruit wholesaler across on the

other side of the island today. Apparently, they’re the only place that does the specific type of passion fruit that works with her new juice recipe. As it was a big order, she told me to take her car, which was a nice bonus – the nearest my dad would let me get to his Mercedes was the rear passenger seat.

Anyway.

I turned up at the warehouse and before I had even gotten out of the car, I spotted Rick walking into office at the side of the main building with a guy who looked very familiar for some reason, but frustratingly I just couldn’t quite place. Anyway, I figured that perhaps Kelly had forgotten to tell me that Rick was going to be here as well so decided to go and let him know I was here.

That’s when things got super... interesting.

Hearing slightly agitated, raised voices as I approached, I decided to listen in from outside and peek through the window to see what the hell was going on.

“You kissed my damned wife,” Rick said, his voice struggling to hide its anger, but at the same time clearly a little nervous. “I want an explanation!”

Of course, that’s where I recognised the man from, that night at the café bar.

“Hey, little man, chill,” came the reply, the guy running his hands through his braids and clearly losing patience. “Like I already told you, your wife kissed me. She approached me. She flirted with me. It ain’t my fault, and even if it was, what the hell are you going to do?”

At this point, I could see that beyond his wounded pride and jealousy, Rick was in actual fact rather intimidated by this man. Still peeking through the window, I watched as his body language seemed to totally give his nervousness away. It wasn’t as if he was cowering in the corner or anything, but his back was pretty much up against the door to the office at this point and if I didn’t know better, I’d have said he was struggling to stop his legs from shaking.

Meanwhile, the black guy he was confronting seemed to be almost enjoying watching Rick squirm. The difference between the two in a physical sense was absolutely crazy. I mean, it was like when you see a giant from the NBA standing next to one of the female TV reporters.

Except, of course, Rick wasn’t female. But, honestly, he might as well have been.

“Now, unless you’ve got anything else to say to me, little boy, I suggest you collect your fruit and get the fuck out of my place of work,” the black guy said, a hint of a smile on his face as he took two steps towards Rick, towering over him and prompting Rick to simply nod, turn, and fumble his way out of the office.

I quickly walked round to the main entrance, and when I saw Rick made sure to act like I hadn’t just been listening to him getting dominated by the stranger who had kissed his wife.

If Rick suspected I knew anything, he didn’t let on.

He seemed so distracted, troubled, and I couldn’t help but think that this wasn’t going to be the last I’d witness of this situation...

August 8th

Kelly and Rick were arguing in the café today.

Again.

It’s getting a little weird now, because all they seem to do is bicker, the kind of back-and-forth quarrelling that can actually get a bit awkward to be around, even prompting the odd customer to get up and leave.

Still, with my headphones in and my music blaring, I just focused on making up the wraps and fajitas as the brunch orders came in. Ultimately though, there were only so many lightly toasted wraps that needed filling, and as I got back to making coffees, I caught the tail end of a yet another argument...

“You know, it’s not exactly an attractive quality to keep reminding me of my mistakes,” Kelly said, seriously sounding like she was losing her cool. “I could go over all of your... deficiencies... if you’d like? Urgh. Just remember that we’ve got another fruit order, okay? I’m going for a spa session with some friends. I’ll be back whenever.”

Rick looked seriously pissed off now, like he was struggling not to lose it too. But instead of saying anything, he just allowed Kelly to walk out, her body looking as hot as ever in

a loose fitting, but practically see-through white summer dress, the outline of her black thong only emphasising her magnificently built ass.

With Kelly out of the picture, the rest of the shift was a little bit more chilled out. Rick had his own space, pretty much ignoring me as he listened to podcasts and got on with the food prep for the lunch hour rush.

“Okay, so I’m going to pick up the fruit now, you all good?” Rick said as he stepped out of his office.

I nodded and smiled, happy to be getting the place to myself. Then, just as he turned and made his way out of the door, I saw something that made me double-take. To my shock, riding up over the top of Rick’s chinos was a thin, bright pink waistband... and it definitely wasn’t part of a pair of brightly coloured boxers or briefs.

I almost had to rub my eyes in disbelief, but I knew what I had seen.

It was unmistakable.
Undeniable.
Rick was wearing women’s panties, and if the string waist

was anything to go by, it was a very small, skimpy pair too. The kind of skin-tight, figure hugging pair I’d wear ahead of a third or fourth date, you know... if I was planning on taking me clothes off around a new boyfriend or something.

The plot thickens, XoXo

August 12th

“Feel free to make yourself a drink, whatever, just be ready to take the delivery when it arrives,” Kelly said to me as she walked into the garden wearing a matching yellow sports bra and micro-shorts, her body looking as curvy as ever, but strong too.

So, I was over at Rick and Kelly’s house today, apparently Kelly had an online Zoom workout that she couldn’t miss, and I was required to attend to a couple of deliveries that were expected.

I was fine with it. Easy money to be honest. The benefit on top of that being I could actually take a look at the inside of Rick and Kelly’s luxury house. It really didn’t disappoint either.

Anyway, having made myself an iced coffee I picked up Kelly’s iPad to check on the status of the deliveries. Both were pretty close now, so I didn’t have long to wait. But just as I was about to put the iPad down, I had a sudden desire to have a little look through the photos on there.

Call me nosy, whatever. I just had to look.

They were pretty dull to be honest, mainly family get togethers back in the US, a couple of screenshots from

Pinterest, that kind of mundane thing. Then, totally taking me by surprise, I swiped onto a photo of a naked torso and huge, hard dick that most definitely wasn’t Rick’s.

The deep, perfectly chocolate brown skin and rippling, well-defined abs were hot enough to get me off just by themselves, but the sight of what must have been well over ten inches of heavy, pumped up dick-meat was just something else.

But why the hell was this photo on here?

It didn’t look like a screenshot from the internet, so did that mean that someone had sent Kelly the photo?

I had so many questions, but the sound of Kelly jumping, squatting and generally working her booty in the garden made me snap out of my trance and I quickly swiped off the photo and put the iPad down on the kitchen work surface, my heart pumping and the heat between my legs definitely noticeable to me too.

Luckily, my mind was soon distracted as Kelly’s deliveries arrived soon after, and I happily signed for each one before taking them through to the downstairs study as instructed.

Just before I left the house to meet up with Malik for lunch, Kelly called me into the garden. Her tanned skin was drenched in sweat, and I felt myself blush a little at the sight of her nipples pressing very prominently through her flimsy top.

“Hey, sorry about all the negativity between me and Rick recently,” Kelly said, a smile on her face. “But don’t worry, it’s all good now. It’s been sorted.”

“Oh, yeah, right, don’t worry,” I said, trying to process Kelly’s energy, work out exactly what she meant. “It’s fine, thank you.”

Kelly smiled, clearly aware that I had a little bit of a crush on her. It wasn’t just her looks though, it was her demeanour, her attitude. I’d noticed recently that she had been a bit firmer with Rick, and Rick had definitely been a little more submissive. It wasn’t like a major change or anything, just subtle differences most days that had a cumulative effect over time maybe.

“Hey, take this,” Kelly said, handing me fifty dollars. “Enjoy your date with that majestic young stud of yours. Once you go Island Black...”

Kelly smiled, a wicked look of mischief on her face as she watched me blush again, enjoying every second of my embarrassment. I turned and left, ready for my date but also at the same time wondering exactly what the hell was going on between Rick and Kelly.

Rick in panties.

Dick-picks on Kelly’s iPad.
The other, subtler changes I’ve noticed in their dynamic.

There’s so much going on here I’m going to have to keep my eyes and ears alert now more than ever.

August 25th

I’ve been spending a bit more time with Malik and it’s feeling... good. I don’t know where it’s going to lead to exactly, but it’s definitely fair to say that I’m enjoying very much getting reacquainted to that body of his. Honestly the contrast between the soft, rich whiteboys I dated at college is so noticeable, and that’s definitely a good thing.

I’ve been keeping tabs on Rick and Kelly too, although up until today I hadn’t managed to see anything new to help build my picture of what seems to have been going on behind closed doors. However, when Malik and I went for an afternoon hike we were treated to something pretty shocking...

“Wait, did you hear that?” I said, stopping in my tracks and putting my arm across Malik’s bear, glistening chest. “Does that sound like... spanking?”

Malik paused and listened with me.

There was definitely the sound of rhythmic slaps, skin on skin, and muted, muffled cries of pain. We were halfway up the hill trek we had been planning for the last week, but suddenly there was something far more interesting on our minds than whether or not we were going to beat our two-hour target time.

“Damn, Riley, I think it’s coming from over there, in the undergrowth,” Malik said, looking genuinely puzzled but as the same time intrigued. “It sounds like someone is teaching their woman a lesson all right!”

He was only joking, but I gave him a playful slap on his round, perfectly muscled ass. Very carefully, and being as quiet as we could be with the dry, rough terrain beneath our shoes, we crept into the undergrowth, the sound of the apparent spanking getting closer and closer.

“No way, no freakin’ way,” I said, crouching down behind a bush, Malik’s huge frame practically bent over double next to me. “I can’t believe it.”

“Is that your... boss?” Malik said, his hand over his mouth in shock as he whispered.

It was my boss.

But the feminine sounds of pain that we had heard weren’t Kelly’s, they were Rick. I couldn’t quite get over what I was seeing. Part of me wanted to burst out in laughter, but I watched in total silence as Rick, bent over a felled tree and with a pink thong around his ankles, took spank after spank on his

red-raw ass by a huge black guy... the very same guy who he had the argument with in the fruit warehouse, and yep, the guy who Kelly had kissed on her drunken night out.

This was absolutely insane.

“I told you, don’t ever sass me in public,” the man said, briefly pausing between spanks to grab Rick’s hair and turn his head to face him. “If I tell you to wear Kelly’s booty shorts for our hike, then that’s what I expect to see you in. Understand?”

“Y-y-y-yes, sir, I’m sorry, please, I’ve learned my lesson,” Rick said, the sight of him bent over and with panties around his ankles taking some getting used to from my point of view. “Please, someone could easily walk in and see us, Keelan.”

“Yeah, and they’d see your fat little booty getting a whooping,” Keelan replied, his muscle and schlong-filled jet-black cycling shorts making him look like an Olympic sprinter as he stood there, observing, controlling, admonishing his little pet. “Get up and put your shorts back on. You’re lucky I don’t make you walk the rest of the way in just your thong, show everybody what a little bitch you are.”

“Thank you, Keelan, sir,” Rick said, hurriedly covering his modesty, the sight of his thin, stubby-looking dick making Malik shake in silent laughter. I personally found Rick’s little dick kind of cute in a way, although of course when it came down to actually using it, I couldn’t see how it was ever going to be enough for Kelly, or any woman in fact.

“Now, are you going to be a good boy for me?” Keelan said, his huge arm over Rick’s shoulder, his large, expansive hand hovering over Rick’s left nipple. “I don’t want to have to punish you again. Not today anyway.”

“N-n-n-no, I’ll be good, I promise,” Rick said. “Just please, don’t tell anyone about this. Not your friends, your work colleagues, and definitely not anyone who knows Kelly.”

Keelan laughed and with his other hand reached down the front of Rick’s shorts, the muscles in his arms flexing as he squeezed his fingers over Rick’s manhood, tightening his grip as he spoke.

“I’ll do exactly as I want, and you should know that by now,” Keelan said, smiling at the sight of Rick’s face going red, a look of sheer anguish on his face. “But, sure, I’ll keep it quiet for now. Just as long as you stay on your best behaviour.”

Malik and I stayed incredibly still and held our breath as Keelan and Rick walked close by and back up onto the hiking trail. I wasn’t going to forget what I’d just seen, that was for sure.

But I can’t help wondering exactly how much Kelly knows about this? Is she complicit, or is this Keelan guy secretly playing the two of them off against each other, gradually working his presence into both of their lives?

It’s enough intrigue to keep a girl up all night! XoXo

September 7th

Well, that was certainly an interesting day, and night too...

“Riley, you’ll be staying at our place while I’m out of town for a couple of days,” Kelly said to me, seemingly not caring that Rick was standing right next to her. “I need someone at home to make sure my husband behaves.”

I couldn’t believe it when I heard these words being spoken so casually, with the kind of authority that suggested Rick really had no say in what was going on in his own home.

I looked over at Rick and he was barely able to make eye contact with me. I also couldn’t help but notice that he was wearing tighter clothes than normal too. His t-shirt, a kind of pale, pastel pink colour was so tight it gave him a pair of small, evidently pretty squidgy man-boobs, the outline of his nipples unmistakably clear through the thin material. His shorts actually looked like a pair of Kelly’s, the tightness around the crotch area putting a spotlight on his tiny little package.

When I showed up to the house later that evening, Rick barely acknowledged me, seeming engrossed in his iPad and probably still a little embarrassed about earlier. He’d changed

out of his clothes too, now wearing a big, fluffy pure-white robe instead.

“Okay, so I’ll probably just head to the guest room?” I said, Rick forcing a smile and watching me as I walked back out into the entrance hall and up the winding marble staircase.

A couple of hours passed, and just as I stepped out of the guest suite bath and wrapped myself up in one of the luxurious towels, I heard a knock at the front door.

Maybe Rick had ordered takeout?

I was about to fling on a robe and go and answer the door, as per Kelly’s instructions, but then I heard Rick get their first and the sound of a familiar voice.

It was... Keelan.

I crept out of my room and practically crawled along the floor to a spot where I could look, listen, and hopefully find out more...

“W-w-w-wait, how did you know where I live?” Rick said, nearly falling onto the floor as Keelan pushed past him and into the hall. “You can’t be here. You’re lucky Kelly isn’t in. You’ve caused enough problems between us.”

“Oh, I don’t think Kelly would mind seeing me too much,” Keelan said, a knowing grin on his face. “Maybe she’s the one who sent me here tonight?”

Keelan was obviously playing with Rick, knowing full well that in this situation he was the one totally in charge. Dressed

in a pair of denim shorts and a white vest, Keelan looked every inch the kind of island alpha male that female tourists and outsiders drooled over. He was older than Malik of course, but I could definitely visualise Malik looking like this in a few years. And I liked it.

“Look, I don’t want any trouble,” Rick said, his robe having come undone, his naked body exposed and vulnerable. “I...”

Before he could finish his sentence, Rick was being lifted up by his arms, the robe being pulled off and leaving Rick totally naked, apart from one little detail...

“Just how it should be,” Keelan laughed, his eyes being drawn towards the baby-blue plastic chastity device that was keeping Rick’s little dick perfectly locked up. “It’s not as if your clitty is needed for anything, now is it?”

Keelan grabbed Rick by the waist and spun him around before then pulling him in close, his pale, porcelain-coloured ass pressing right up against Keelan’s denim crotch. There was something about the way that Rick, despite clearly being uncomfortable and trying to resist, simply didn’t have either the physical strength or strength of character to actually stop Keelan toying with him like this.

“Push that butt back, wind it for me,” Keelan said, his booming voice echoing around the high-ceilinged hall. “Show me how much you enjoy twerking and working that ass for a real man.”

Despite the fact that he clearly didn’t want to do it, the look of sheer dejection on his face telling me everything I needed to know, I watched as Rick began to bump and grind his fat booty into Keelan.

There was something about the sight of him degrading himself like this that was actually turning me on. I mean, it didn’t make me attracted to Rick, far from it. But the situation itself was definitely making me horny, my titties swinging beneath me and nipples grazing back and forth against the shiny, smooth floor as I continued to watch on all fours, making sure to keep myself safely tucked out of sight.

With the fingers of one hand rubbing over my engorged, throbbing clit, I placed my spare hand over my mouth to stop myself from audibly moaning as Keelan grabbed and squeezed on Rick’s breasts, pulling and twisting on his large, puffy nipples, all the while continuing to bump his crotch back and forth on Rick’s naked ass.

“I bet if you didn’t have that cage on your little dick would be rock hard,” Keelan laughed, pushing Rick onto his knees. “You’re lucky that tonight I have another engagement to get to otherwise I’d be putting you to more work. Still, there’s plenty of time for that.”

Rick looked shocked, terrified even.

Then, for a brief moment, I thought I had been rumbled as Keelan seemed to look beyond Rick and up towards the open

plan first floor landing. I held my breath and didn’t move a muscle until I saw Keelan leave, the heavy door shutting behind him, his laughter audible as he walked away down the driveway.

Before slowly and quietly creeping back to my room, I looked on as Rick stood up, walked to the large window and watched his tormentor drive away.

Despite everything I had seen, there was definitely more going on here. I felt like it was time to expand my horizons, and where better to start than some late-night Googling.

So here I am, laptop open.
First search: male chastity and BBC.

September 20th

Along with all the research I’ve been doing online, the last couple of weeks have shown me more proof, not that I needed it at this stage to be honest, that Rick and Kelly’s relationship was now operating on very different terms.

I was a more regular overnight guest at the house now, almost acting as a babysitter as Kelly spent more time on nights out with her girlfriends, often not returning until sunrise. Rick meanwhile continued to be regularly tormented and teased by Keelan, who would now think nothing of turning up, stripping and spanking Rick before making him pose for photographs in the most humiliating positions and poses imaginable.

Sometimes with panties on, sometimes without.

The chastity cage was always on though, and I had begun to notice that Rick was wearing it underneath his increasingly feminine clothes too. It was almost like an open secret of some kind, Kelly often teasing Rick in front of me, nearly-but-not-quite revealing his secret.

So, when Kelly invited me for lunch today, I had a feeling that it wasn’t going to be a simple case of bruschetta, champagne, and the usual work chit-chat...

“Riley, you’ve probably noticed a different vibe between me and Rick?” Kelly said, admiring the waiter as he poured our

glasses of fizz. “Hopefully it’s a lot easier to be around us now that the fighting has stopped.”

I wasn’t sure how to respond.

I didn’t want to be rude, or come across as speaking out of turn, so just simply smiled and let Kelly continue. To be truthful, I could just sit and listen to her talk and talk, her sensual, but authoritative tone of voice never failed to draw me in.

“You see, there are certain things you can do to keep a man in check,” Kelly continued, sipping on her champagne and looking every inch the modern woman in control. “I’ve been learning. Slowly but surely. Rick kind of resisted at first, well... he still does sometimes. But he’s getting there.”

“Um, okay,” I said, now actually feeling a little uncomfortable. “I’m sorry, but why are you telling me this?”

Kelly laughed.

It was the kind of laugh that someone does when they imply don’t care who hears them. I felt intimidated, suddenly very aware that Kelly was, first and foremost, my employer and about a decade older than me.

“You’ve got a lot to learn, that’s why I’m telling you this,” she said. “Oh, and the fact that I’m going to need you to help me in continuing Rick’s education.”

Wait... this sounded way beyond my job description.

But I was intrigued. Something about the idea of me helping Kelly was undeniably exciting, my heart beating rapidly as Kelly simply looked at me, her eyes fixed on mine, gauging my reaction.

“Um, okay, I guess,” I said, nervous but still feeling that injection of adrenalin coursing over my entire body. “I’ll help however you want.”

“Perfect,” Kelly said. “Let me fill you in on exactly what I want you to do.”

September 27th

Today was the big day. It had come around quickly too. Ever since lunch with Kelly and agreeing to help her with Rick, she has been messaging me, sending me emails with links to articles, Tumblr pages, video clips all focusing on the idea that a modern-day submissive husband needs to be in service to his wife.

It had me intrigued.
Excited.
It was like the more I read, the more it made sense. And

there were definite overlaps with the kind of stuff I had witnessed between Rick and Keelan. It was like Kelly somehow knew of Rick’s true nature, his willingness to break and submit to a superior man and woman. Well, I say willingness... but there was still plenty of resistance from Rick if the sight of him being spanked by Kelly in the rear garden last weekend was anything to go by!

Still, it wasn’t my place to question anything.

No, my role was to assist Kelly, carry out the instructions she gave me to the letter, and then let her do the rest. Which brings me neatly to what happened today...

As instructed by Kelly, I turned up at their house and quickly got changed into a one-piece thong swimsuit that just so happened to match Kelly’s. The pair of us played around in the pool, tanned under the morning sun, and generally had a good time.

So far, so normal.
But Kelly’s plan was about to kick in...
“Rick, get over here, right now,” Kelly said, her relaxed,

chilled out vibe suddenly being replaced with something entirely different. “Were you spying on our guest, our employee, the daughter of our friends? Don’t even think about lying, I saw you up at the bedroom window.”

Rick looked shocked.

Had he actually been spying on me? If so, I was more than happy to see Kelly taking him down a peg or two. Either way, Kelly was far from finished with him. As Rick appeared in the garden, his white t-shirt cropped around the navel and his powder blue shorts high on his waist, he already had the look of a worried man.

A very, very worried man in fact.

“I let you roam free without your little device for one day and this is how you repay me?” Kelly said, enjoying the look of increasing horror on Rick’s face. “Just admit it, you were leering at mine and Riley’s bodies as we lay here. That’s a question, and I expect an answer!”

“I... I... I’m sorry, I just caught a quick glance, I didn’t mean anything by it,” Rick said, his voice trembling, his body language giving his shame away, and guilt too most likely. “Please, let me make it up to you both. How about I make some iced lemon water?”

Kelly laughed.

“Nope, not good enough,” she said, turning to me. “Riley, don’t you think this little pervert deserves a taste of his own medicine?”

I knew what Kelly expected, and took a deep breath before speaking.

“Yes, I think he does,” I replied, surprising myself at just how commanding I sounded. “He deserves to be punished and taught a lesson he won’t forget in a hurry.”

With that, Kelly grabbed Rick and pulled him in close to us. Showing great strength, and ignoring Rick’s desperate pleas, she yanked his shorts down and burst into laughter as his dick popped up, hard and cleanly shaven too by the looks of it.

“Riley, can you believe I have to put up with such a useless little thing?” Kelly said to me, pulling her palm back and then landing a hard, flat blow on Rick’s erect noodle, his squeal of pain on prompting her to fire off two, then three, then four more hits. “You’re such a perverted little bitch, Rick. It’s times like this I can’t even believe that I married you. Riley, be a darling and spank his ass for me.”

I knew this moment was coming.

Kelly had made it very clear in her messages that I would need to administer some kind of physical punishment and now was the time. I decided to just go for it, not let my nerves build up and take control...

“That’s it, you work both cheeks, make him holler,” Kelly said as she watched me spank Rick’s ass at least twenty times on each cheek. “You see, this so-called man thinks he can look and stare, get his pencil-dick all hard just because his wife has let him have a day out of chastity. Well, that’s simply not how it goes down. He has to learn, and if that means pain and a spanking from a recent college grad, then so be it. Okay, that’s enough. Rick, for the rest of the day you’ll be in my spare one-piece swimsuit. We’ll be like three BFFs, all matching. Except you’ll be at our beck and call, ready to serve us, do whatever the hell we want. Oh, and if the doorbell happens to ring, you’ll be answering it. Got it?”

“Yes, Kelly,” Rick said, turning and running upstairs ready to get into his swimsuit as instructed.

Rick shot me an angry look as he raced away, furious that he’d just been spanked by his own employee no doubt. I looked at Kelly but didn’t need to say anything.

“Oh, don’t worry, I saw that look,” she said. “Rick’s got a long day ahead of him, and we’ll be punishing him over and

over again until he understands that even the slightest disrespect won’t be tolerated in this house any longer.”

Kelly was true to her word too.

As the afternoon progressed, Rick was subjected to insult after insult, nipples clamps, and even had to endure the degradation of Kelly stuffing a large banana in and out of his mouth, making him gag and splutter as she threatened him with “the real thing.”

Which makes me wonder... how far is she going to take this?

All I know is that my next few shifts at work are going to be very interesting indeed. For all of his money, life experience, material wealth, right now he must feel like he’s at the lowest status imaginable having to work alongside me, knowing that I’ve seen him humiliated, punished, and even played a part in the punishment myself. And that’s not even taking into account what I’ve witnessed between him and Keelan. I almost feel sorry for him.

Well, almost! XoXo

October 9th

My early morning swim with Malik was beautiful. The fact that we both decided to take a swim in the nude was an added, rather significant, bonus.

I hadn’t seen Kelly or Rick for a few days, Kelly giving me full responsibility for opening and closing the café. I actually enjoy being the boss there. There’s something kind of fun about running my own place, well... even if it’s only for a few days.

After the swim, and a fun outdoor shower back at Malik’s place, it was time for me to go to the café to open up...

“Oh, Rick, hey?” I said, a little surprised to see Rick already in there, a slightly panicked look on his face. “I didn’t realise you’d be in.”

Rick definitely looked more than a little sheepish.
I soon realised why...
“This is a bit embarrassing,” Rick said, realising that I’d

just noticed that he didn’t seem to be wearing anything underneath his apron. “I know you’ve seen some stuff going on between me and Kelly. Well, I know, you’ve more than seen it. Can you just forget about this? No need to help me now. Maybe go home, come back later?”

This didn’t sound right.

Kelly had warned me that Rick might try and be a bit devious around me if he felt insecure or under threat, and if I had any suspicions, I was to inform her. Well, I certainly would be informing Kelly about this, but I wanted to find out more right there and then.

Just as I was about to press Rick for more details, I heard the sound of movement in the kitchen and then, seconds later, saw the imposing figure of Keelan walk in.

“So, you must be Riley?” Keelan said, looking me up and down, his deep, soulful brown eyes almost hypnotic in their power. “Keelan. But you already knew that right? Anyway, has our little boy shown you hit latest toy yet?”

Intriguing...

“Um, no?” I said, fully aware of Keelan’s eyes still drinking each and every inch of me in. “Maybe I should go.”

“Yeah, you go, Riley,” Rick said, panicking, a look of desperation on his face. “I’ll pay you overtime, whatever. Just go now. I’ll see you later.”

Keelan stepped in front of Rick and grabbed his ear.

“Riley, please stay,” Keelan said, his firm, deep voice making it less a question and more a firm invitation. “Sissy, don’t be shy, show Riley your new toy. Do it fast or I’ll be kicking your damn ass right here and now.”

Slowly but surely, Riley removed his apron, his hard little dick bouncing up, a thin strip of pubic hair having been allowed

to grow again above it. He turned around and to my shock, a thick purple dildo was hanging out of his ass, thick, long and curving like an eggplant.

“I’m getting this little sissy ready for the real thing,” Keelan said, grabbing the end of the dildo and shaking it before gradually easing it further inside Rick’s ass. “Rick’s got a tight little booty, so I’m training him nice and slow. Isn’t that right?”

“Yes, sir,” Rick said, his face burning deep red in disgrace. “Please, can I-”

“You can shut your mouth,” Keelan bellowed, pushing the dildo deeper inside Rick. “Little sissies don’t speak unless spoken to. Now, get back to work, I want to see you get every table ready for Riley before she has to open up. When we’re done, we’re heading back to my place, I want my car cleaned and my lawn trimmed.”

Keelan took his photo out and took several photos of Rick as he cleaned, smiling to himself and also over to me as I watched, my mouth wide open, stunned but also not entirely surprised at just how far Rick had fallen into this lifestyle, not just with his wife, but with Keelan too.

October 10th

You know when you’ve been working on a jigsaw puzzle for a while, looking to get the various sections you’ve completed to fit into the larger picture? Well, that’s what began to happen today, in a big way too.

Except it’s not an actual jigsaw I’m talking about, it’s the whole situation with Kelly and Rick. The fact that I’m writing this up in my now regular guest room at theirs should be a clue as to what happened...

“Don’t you think my little sissy hubby looks cute?” Kelly said, cuffing Rick’s hands in pink fluffy handcuffs and leading him around the room, his lacey pink bra and matching panties looking incredibly feminine and perfectly fitted on his slender body, the only difference today being that inside the bra, Kelly had fixed two large, highly realistic looking breast forms. “I think I might change his name from Rick to Vicky. After all, what kind of actual man would allow for this kind of treatment?”

“I think Vicky could definitely work as a name,” I said, noticing that Rick wasn’t even trying to shoot me any looks of disapproval now.

“Today is a big day for Sissy Vicky,” Kelly continued, mockingly squeezing on Rick’s new breasts. “We’re entertaining, aren’t we?”

Rick nodded solemnly, his spirit seemingly broken.

“Oh, cheer up you bratty little wiener,” Kelly laughed, slapping Rick across his ass. “I expect my husband to be happy that not only will his wife be having a fun time, but you will too, won’t you Vicky?”

“Yes, Kelly,” Rick said, his hands hovering over the front of his panties, attempting to protect his modesty in front of me.

Kelly proceeded to make Rick catwalk up and down the hallway, the fact he was in handcuffs and a pair of very high heels making it hard for him to walk, and all the more amusing for her...

“Don’t fall now, my slutty little toy,” Kelly said, aiming a kick in Rick’s direction, the threat of being hit making him wobble, nearly falling headfirst into a large indoor plant pot. “I certainly hope you perform better than this when our guest arrives.”

There it was again, the mention of a guest.

But who?

I guess deep down on some level I already knew the answer to the question. Or at least, I knew the answer to half of it...

“Here they are!” Kelly said, the familiar chime of the doorbell signalling the real beginning of Rick’s torment. “Sissy, don’t be rude and keep them waiting. Wiggle that jiggly white booty over to the door right this second.”

I stood next to Kelly as Rick hurried over to the door, nearly falling over not just once, but twice, finally managing to get to the door and open it.

First, of course, Keelan stepped in.

But to my surprise, behind Keelan was Malik, a huge grin on his face, revelling in the fact that I was just as shocked to see him as Rick evidently was.

“Hey babe,” Malik said, striding over to me and giving me a deep, passionate kiss on my lips. “You have a fantastic house, Kelly.”

“Well, thank you Malik, I’m so glad you came here to enjoy this with us,” Kelly replied, shooting me a look of approval as her hungry eyes devoured each and every inch of Malik as he stood next to me, his strong arm around my waist. “Now, what are we waiting for. Let’s get this party started. Sissy Vicky... champagne, four glasses, in the entertainment room, now!”

“But, Kelly, you never said anything about anyone else-”

“Sissy! Don’t be difficult. Get that butt of yours into the kitchen and have our drinks ready in sixty seconds flat.”

Both Malik and Keenan laughed as they watched Rick totter and wobble his way into the kitchen, his panties riding up his smooth, rounded ass.

As the two men walked into the entertainment room, Kelly took my arm into hers as we walked.

“You know, this is the ways things need to be,” she said. “You’re lucky, you’re young, you’ll never have to put up with a weak, bratty beta husband like I’ve had to. Anyway, Rick’s happier now than he’s ever been, even if he doesn’t fully realise it yet!”

Rick soon joined us as we waited for our drinks, the fact he was handcuffed making it even harder for him to not spill the drinks. I could just see the entire serving tray falling from his hands and crashing onto the floor.

“I don’t expect to see a single drop spilled,” Kelly said, her tone firm and with an added level of menace that suggested she’d actually be pretty happy to see Rick spill some of the champagne if it meant she could jump into some cruel and humiliating punishment for him. “Good. Now, parade for us. I know Keenan has seen you in panties before, but this is extra, a whole new level. Go on, show the real men just how much of a feminine, perfectly prissy little husband you are.”

It didn’t take long for all four of us to start hurling abuse and mockery in Rick’s direction. He looked absolutely pathetic as he attempted to move his body, his balance totally off, and

the fit of the bra and panties only serving to highlight how physically inferior he was to everyone else in the room.

“Okay, so I don’t know about you, but I’m hungry,” Kelly said. “Men, how about you do the decent thing and provide the food.”

Knowing exactly what Kelly meant, both Malik and Keelan confidently removed their pants, their briefs slowly coming down to, revealing two eleven-inch dicks, still hardening and looking more like over-sized police batons than any kind of regular, run of the mill penis.

“We’re lucky ladies,” Kelly said to me, licking her lips as Keelan gripped his dick and pumped on it a little, his large, heavy-hanging balls swaying beneath. “But I’m feeling generous. Seeing as Sissy Vicky has done so well in her training over the last few weeks, I think she should get to eat first. Does that sound okay with you, Keelan? Malik?”

The two men smiled, their high cheekbones showcasing their perfect bone structure and pure, white smiles. As they stepped towards Rick, I could see the look of total panic on his face. He was like a deer stuck in the headlights as they began to lay their hands all over him, his body visibly shivering and trembling as he felt their touch all over.

“Wait, this should help,” Kelly said, removing her top and walking over towards the three of them, her titties bouncing. “A little oil for me, and a lot for sissy.”

I watched as Kelly oiled up her breasts and let Keelan squeeze them together and then pull on her nipples as a helpless Rick watched. Kelly then pulled Rick’s panties off, spread his cheeks and squirted a hard blast of the oil over his pink, exposed ass hole.

“All you need to do now is choose who gets which hole,” Kelly said, walking back towards me and immediately taking my hands and placing them on her titties. “Get a good feel then get your clothes off, Riley. We’re all going to be having fun.”

“No, wait, guys, anything but this,” Rick pleaded, Malik lifting him up by his arms and Keelan by his legs, the two men having chosen which end of their sissy they wanted to use. “Kelly, please!”

“Oh, shut that ridiculous mouth of yours,” Kelly said. “By the look of that little pecker, you seem to be more than enjoying this.”

Kelly was right.

Rick’s dick was hard, throbbing almost as it twitched and flexed, the feeling of being overpowered and man-handled by Malik and Keelan clearly doing it for him on some level, even if he didn’t want to admit it.

“Now, men, fill my little man up!” Kelly declared, guiding my hand down the front of her panties as she held her phone up to record the fun. “See, I told you you’d enjoy it, Vicky!”

I watched as Malik thrust his dick into Rick’s mouth, the training Kelly had given him clearly paying off as he managed to take the entire length in one attempt, his muffled cries more to do with Keelan spreading his oiled cheeks and pushing his thick, bulbous dick head inside his ass, wasting no time in pushing the length of his shaft in.

“Pop goes the cherry!” Kelly laughed, ensuring to make eye contact with Rick as he was roasted from the front and the rear, his body at that moment simply a vessel to take real, alpha dick. “Keelan, make sure to reach under and give those titties of Vicky’s a squeeze. She was really looking forward to showing them off for you.”

Keelan laughed and in between thrusts did reach underneath and squeeze on the breasts, his grunts matching Malik’s, who actually looked like he was about to fill Rick’s mouth up with cum at any moment.

“Feel free to spray away, Malik,” Kelly said. “Maybe half in his mouth, half on his face? I know Vicky would enjoy that.”

I gasped then as I watched Malik’s strong ass clench, his thighs too, his entire core focussed on pumping out as much of his seed as possible. When he pulled his length out of Rick’s mouth and continued to spray the thick, stringy goo over his face, I felt Kelly shudder next to me, her first orgasm arriving with perfect timing.

“Keelan, make that ass clap for me,” Kelly said, handing me her phone and beginning to work her own pussy with both hands. “Punish him, punish that stupid... useless... sissy... ass.”

The sight of Keelan ploughing in and out of Rick at full speed was too much for Kelly to handle, her loud, long orgasm coinciding with her bull filling her sissy, submissive husband up with his seed.

“Crawl over to me, kiss my feet,” Kelly said, breathless after two rapid-fire orgasms but still demanding that a shocked and stunned Rick keep up his role as subservient sissy hubby. “That’s it, lick between each toe. Let the cum drip over your face and out of your ass. Now do the same for Kelly. Then Keelan. Then Malik.”

I giggled as Rick’s tongue tickled between my toes, the sight of him totally obedient now, not even showing the slightest hint of sass or disrespect towards his wife was something to behold.

“Does it feel good, sissy?” Kelly said, finally beginning to get her breath back. “To know that this is your role from now on? To know that you’re my little toy, my pantied, big-tittied little pet? To know that all you need to worry about is obeying me, serving me, and following my orders?”

Rick gave a muffled Yes, Kelly in response, his face now squished up between Malik and Keenan’s thighs, his tongue working over-time to clean up their cum and sweat.

“You know, I’m thinking of maybe writing some kind of sissy husband training manual,” Kelly said to me. “I figure there are a lot of ladies on the island with similar husbands, women whose lives would be much better served with a converted hubby like Sissy Vicky. You seem like you could help me. Fancy it?”

I laughed.

“Come on, don’t leave me hanging,” Kelly said, running her fingers over my nipples, gently squeezing on them, her attention turning quickly to the fact that both Keelan and Malik seemed to be getting hard again. Already. Rick gasped, opened his mouth, and simply allowed Malik to ease his dick in again, the perfect sissy boy-toy. I turned to Kelly and smiled before turning back to watch the show.

“I’ll take that as a yes then!” Kelly laughed, her eyes wild and full of animalistic lust at what she was witnessing. “If I can get him like this after five months, just imagine what’s possible after another five...”

Well, if I’m to be helping Kelly with her new project it looks like my diary will be getting put to good use, that’s for sure. With everything I’ve observed and noted, not to mention all the research I’ve done on top, I think I might just have found the kind of career I would want to put full time hours into...

Until next time, Queen Riley XoXo