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Chapter 1 – The Naughtiness Starts:
My wife Penny and I had a trip planned to a high-end all-inclusive hotel in Jamaica but right at the last minute disaster struck, she got an inner-ear infection that meant she wasn’t allowed to fly. I tried to reschedule the trip but the fees were way too expensive, the only option was changing the name on the booking. We asked every couple we could think of but school holidays, the cost, or the lack of remaining leave from work got in the way from everyone.
As the hotel was ‘adults in a couple only’ (not the dirty one you’re probably thinking of) I couldn’t take my brother and play golf every day, we were in a tight spot until our friend Katie said she’d like to go with me. I never thought in a million years that my wife would agree but she seemed more fussed about getting the three grand back to go towards our next trip. We’ve both known Katie for years so I figured my wife had decided we could be trusted not to get up to mischief. Katie’s had the odd dalliance here and there but she’s never got a long-term boyfriend so she was quite excited about some 5 star pampering, food, and cocktails. Katie is a little younger than me but she’s totally out of my league, I wouldn’t say I’ve always had a crush on her but I’ve certainly always known she’s very hot.
So there we were, getting dropped off at the airport one freezing January morning by my wife. It all seemed a bit odd, Katie and I both got a hug and a word in the ear from Penny, all she said to me was, “Be good, don’t get too smashed, but make sure Katie has a good trip!” The departures hall was noisy with all the other travellers saying their goodbyes so I had no idea what she said to Katie, my guess was she said something like, ‘If Alan starts acting like a dick make sure you call him on it!’
The flight was long but fairly pleasant with not too many kids being annoying or trolley-dollies trying to sell us crap we didn’t need, so we both tried to get a little shut eye. When I woke up after a nap Katie’s head was resting on my shoulder, she looked so peaceful and her hair smelt great, I allowed myself a cheeky peak down at her cleavage as she slept, the rise and fall of her chest as she breathed in and out was mesmerising but after a while I decided that it really wasn’t a great idea – Starting the holiday with an unresolved 9 hour erection was not exactly relaxing so I forced myself to put my eye mask back on and try to go back to sleep.
We were both woken up about an hour before we touched down by the hostess with a set of landing cards, the hostess gave me a very dirty look when asking how many cards we needed, it was only after she’d wandered off muttering to herself that I realised how bad it looked, me with my wedding ring, my beautiful companion without one, we’d also needed 2 customs cards as we aren’t married. When I explained it to Katie she started laughing, I was wondering what we’d let ourselves in for – would there be two weeks of dirty looks and snide comments behind our backs? That’s when Katie suggested we just have a little fun with it.
“Two options the way I see it, either you take your ring off, everyone you meet sees the white mark and assumes you are cheating on your wife or have literally ‘just’ left her, and then assume you’re a dick. Or… You buy me that cute little ring in the in-flight magazine and I’ll be Mrs Alan B while we’re away, how do you wanna play it hotshot?”
I didn’t need to think about it for very long, the call bell was pressed, the frown from the hostess got even bigger, but 15 minutes and £50 later I had a new wife. The ring wasn’t anything fancy but as it was brand new the bright silver could have passed for a more expensive metal.
When we got to the hotel I upgraded us to the next category of room when we checked in so we could get a room with 2 beds. After a long flight from the UK we were eager to get in the pool and sink our first beers so we took turns to have a quick shower and put on our swimming stuff. While Katie was in the shower I logged onto the WiFi and had a video chat with Penny. She was OK despite missing out on the holiday, I promised to check in with her every day. When Katie emerged from the bathroom wearing a fairly skimpy bikini my heart skipped a beat and my cock definitely twitched, she looked amazing. Although she’s in her late 30’s but with her tight athletic body and cute face I think she could easily pass for 25. By contrast my 40’s have started with more than a little middle-aged spread. I still play football and run a bit so I’m not exactly massive but I know everyone would be asking themselves what Katie was doing with me. My eyes lingered a little too long on that bright blue bikini.
“Hey, when you’re done checking me out can we go get a drink?” Katie quipped.
“Sorry, I always knew you were hot but that bikini is something else,” I was hoping that a little flattery might bring an end to the telling off.
“It’s fine, that’s the job of a bikini, some claim maltepe escort it’s about fewer tan lines but for me it all about the looks from hot guys and the free drinks.”
“Bar’s open and my wallet seems a little heavy, care to help me empty it?” I joked, it was an all-inclusive so I’d only need dollar bills for tips but I’d gotten away with what could have been an awkward moment.
She wrapped a sarong around her waist and off we went in search of the first drink of the holiday, one red stripe in the pool bar turned into four or five, then wine with dinner, and two or three Mojito’s later so we were both more than a little tipsy and ready to head off to bed. Again we took turns in the bathroom to change and get ready for bed. Katie wore a baggy tank top and some boyish looking boxers, I’d seen far more of her in her bikini but there was something nice about seeing her in clothes that no one else would get to see. The tank top was so baggy that depending on where she was standing or sitting I got an amazing view of her body.
The first few days all followed a similar pattern, reading our books on the beach or the pool loungers, snorkel trips, a video chat with Penny for me at some point, lots of great food, and a fair amount of booze but not enough that I was brave / stupid enough to try something that might endanger my marriage. We were getting on really well and having loads of fun, using the bathroom as a changing room seemed to be the only thing that made our stay un-natural.
On the fourth day I’d obviously been quicker getting dried and changed after my shower as when I came out of the bathroom, she was just wearing a pair of panties and a sheepish grin. She’d managed to pick up her towel and hot-footed it into the bathroom so I really didn’t see that much but we both felt a little uncomfortable, I had decided we should clear the air at some point in the evening, she must have felt the same way too as when we were sat on a huge outdoor beanbag sofa at the beach bar later she brought it up.
“I dunno about you, but I don’t think our changing room is really working out,” she said.
I thought I knew where she was heading but apparently I didn’t know Katie as well as I thought I did, “I know what you mean, but I don’t have the spare cash to upgrade us to a suite, I…”
“No you dumbass,” she interrupted, stopping me in my tracks. “I mean we need to get ourselves past a little nudity!”
“Oh, right, errr… Not sure what Penny would make of that.”
“Look, it’s no big deal, Penny said so,” Katie said as she slurped the head off the top of her 4th or 5th Red Stripe. “I’m not gonna be putting a show on and I don’t expect you to either, all I’m saying is I don’t think we need to keep hiding away in the bathroom to get changed.”
“OK, I guess, if Penny said she wasn’t bothered about it.” I said, trying to keep as casual as I could whilst secretly wondering about what the pair of them had been speaking about when I wasn’t around.
“The way I see it, from the first time you saw me in a bikini on this trip you’ve seen 98% of me, as has everyone else by the pool and to be honest, I’m really past caring if you catch a glimpse of the rest.”
“98%?” I questioned.
“99% when I move on to the bikini I’ve been saving for next week.”
“Well, I think I can speak for myself and everyone else by the pool, I’m looking forward to seeing that bikini, I promise not to get weird and stare too much when you’re changing.”
“Cool, I’m glad we’ve got that sorted. But just to let you know, I plan to check out the contents of your shorts if they’re on show!” she said, trying to keep a straight face.
We both giggled and I felt so much better, I was so glad we’d had a few drinks before we’d had the chat, I’m always a bit more loose lipped after a couple of beers. She was wearing a really hot summer dress, it was white linen and sheer enough that you could just make out her bright white lingerie underneath. The slight breeze from the ocean had caused her arms to get goose pimples at times so she snuggled in close to me on our little sofa. I felt the most comfortable I’d been so far on the trip, everything I’d had second thoughts about before the trip had melted away.
We had a really nice dinner and a few too many cocktails, so much so that Katie told me in no uncertain terms it was time for me to take her to bed. After the conversation we’d had earlier I didn’t need to be told twice. When we got back in the room Katie went into the bathroom so I got on my bed and was flicking thru the TV channels when she came out. I’d half expected her to still be wearing the knockout summer dress she’d been wearing that night or be ready for bed, in fact she was wearing neither. As her body swished past the TV I saw that she had stripped down to her bra and panties. I pretended to watch the telly but was shamelessly checking her out as she removed her bra and looked around for her tank top. Lit by the soft light maltepe escort bayan of the bedside lamp and the dancing colours from the TV I could see more of the 2% I’d so far missed out on as she searched. Whilst the maid never hid anything, stuff randomly got tidied away in the wrong place at times and Katie’s nightclothes were proving elusive. If she’d been sober I’m sure she’d have looked for them before taking off her bra. If I’d been sober I’d have probably found something on the TV to distract me but her unintended show was just too good to miss, her body was perfect. She didn’t have an ounce of fat on her but she wasn’t skinny, she wasn’t all muscles either, her horse riding and Pilates mad sure she was simply toned from every angle. Her breasts were small I suppose, maybe a 34B if I had to guess, but they were so pert and her nipples so out-front and in-your-face I really wouldn’t want to change a single thing about her.
“Ok, so you’ve had a good look at the girls now, can you help me find my tank top?”
“Yeah, sorry, again… Sorry,” I said. My cock was at half-mast already, even though it was tucked away safely, there was a noticeable bulge.
“Don’t be sorry, like I said, I really don’t mind you having a peak, to be honest I quite like it, but I’m tired now and I want to get some sleep.”
I got up and looked around. It looked really bad for me when I found the tank top and boy boxers under one of the pillows on my bed; it was directly underneath where I’d been lounging and made it look like I’d hidden it on purpose.
“I promise I didn’t hide them, but here you go,” I said as I handed them over, staring down at the floor like a naughty kid.
“No problem man,” she said in a terrible fake accent as she popped it over her head and slipped her boy-boxers over her panties. “I’ve found them somewhere different every night so far. Anyway, now that you’ve had the show it’s out of the way isn’t it! And now I won’t feel guilty that it’s your turn.”
“My turn? Err, Ok!” I said as I took off my shirt and unbuttoned my linen trousers.
Katie was sat on her bed with her back against the headboard looking straight at me, if she had a clipboard I swear she’d have been making notes or marking me out of ten.
Once I’d taken my trousers off I was standing in my boxers, so I was ready for bed but I figured it wasn’t really fair given what I’d seen so I decided that I needed to switch them for a new pair so I went over to the chest of drawers and found a new pair, then standing side on so Katie could get a decent but not full frontal view I slowly pulled my boxers down and stepped out of them, pausing briefly to check out the tan lines left by my board shorts in the mirror I pulled on the new pair and got onto my bed and turned the TV off.
Katie and I both lay on our sides and looked at each other across the gap between our beds in silence for a moment.
“So Mrs B, did you get a good enough view from there?” I said eventually
“Yes thanks. Nice touch that, switching your boxers against your normal routine.”
Taken aback a little I said, “My routine?”
“Yeah, We have our day in the sun with you in boardies, you shower, put on a fresh pair of boxers for the evening, you sleep in them, and go to breakfast in them, then you swap for boardies and the whole thing starts again, you switched them so I’d feel better about what you saw.”
“Was I that obvious?”
“Yes, but I thought it was very noble of you to show me your cock!”
“I don’t think anyone has uttered that sentence before in history of the English language, but on that note… I think it’s time to get some sleep, anything else I say or do is bound to get me into more trouble,” I said as I reached over and turned off my bedside lamp.
“Night night, my fake hubby,” said Katie as she did the same with her bedside lamp.
I woke up a few hours later sweating buckets, the room felt like it was about 90 degrees, I looked over at the Air Con panel, it was lit up like a Christmas Tree – a sea of flashing red lights. I was feeling dehydrated so I went to the mini bar and got myself a bottle of water. As I opened the fridge it the room was flooded with a cool blue light and I could see that Katie had been suffering in the heat as well. She’d dispensed with the blanket and sheet, her boy-boxers were on the floor and she’d pulled up her tank top exposing her flat belly and the very bottom curves of her amazingly pert breasts. The light had caused her to stir from her slumber and she asked me to pass her a bottle.
I pulled a second bottle out of the fridge and wandered between our beds and placed it on the bedside table before getting back onto my bed. She rolled over onto her side so she was facing me, she picked up the bottle and immediately placed it on her forehead, when the condensation from the cold bottle ran down her face then her neck she let out a deep sigh. I watched intently as the bottle slowly moved south maltepe escort bayan onto her cheeks, then her neck and the top of her chest, as it grazed her tank top the white fabric water droplets made tiny damp patches which made it stick to her skin even more than before. When the bottle again touched her skin again as it reached her stomach she let out little moan. I was transfixed as I followed the line of the bottle. I’d hoped it was going to go further but Katie needed the drink as much as I had done so after the bottle had reached her belly button she sat up and downed the whole bottle in one go. She then must have decided fewer clothes was the way to go too as she pulled off the tank top we’d played hide and seek with and tossed it aside. She lay on top of the sheets wearing just her panties, which were very brief and pretty sheer so left little to the imagination; they were powder blue with an intricate floral pattern, allowing me an almost unrestricted view of the outline of her pussy.
I also slept above my sheets facing Katie. At around 8am the gaps in the curtains had flooded the room with the morning Caribbean sunshine and Katie and I were still facing each other, about 3 feet apart wearing very little, needless to say, I had a touch of ‘morning glory’ as my cock strained against my boxers. The situation was exacerbated by the sight I’d woken up to, Katie was still facing me. In her light slumber her arm was on auto-pilot gently stroking her skin just where the top of her leg and panties met. I wanted to look away as I knew this was crossing a line of trust that we’d built up only the night before but it was such a beautiful sight, I let the devil on my shoulder dictate my actions. I closed my eyes apart from a tiny crack just in case Katie woke up, I placed my hand over my boxers and started lightly stroking myself in a similar way to Katie. We must have stayed like that for 30 minutes or so but eventually the need for relief got too great. I quietly got up and went into the bathroom, once inside I stripped my boxers off and furiously masturbated, my climax came quickly but it was oh so satisfying. I sighed a little too loudly as I let loose and I was sure that Katie would have been woken by my actions. I had a cold shower to cool off and went back into the bedroom to open a window to let some fresh air in. Katie was still in bed but her arm was now by her side and she was underneath the bed sheet. As I got back onto my bed I could see she was trying to stifle a smirk.
“Is that better?” she enquired?
“Yes, thanks, I feel much fresher after a cool shower,” I said, trying to steer her thoughts away from my actions.
“Mmm, I think a shower is definitely what I need,” she said as she slowly got out of bed. Once again I got an amazing view of her naked top half as she walked towards the wardrobe. She pulled down her panties and sashayed her way towards the bathroom allowing me to see that knockout arse of hers. “I’m so hot and bothered, I think this shower will come as a great relief,” she added as she disappeared out of view.
I’d gotten ready for breakfast by the time she exited the bathroom wearing nothing but a towel.
“Shall I see you at breakfast?” I said, “I’ll need to go tell the front desk about the busted Air Con.”
“Up to you cupcake, I’ll be ready soon and I think you’ve probably seen all I have to offer by now.”
“I don’t think I could take another hot night like that, I’d best go see the manager, with the maintenance teams in hotels like this you want to be at the top of the list for jobs that day!”
“Ok, see you at breakfast then, get me an omelette and a smoothie, ok hun?”
“Sure, see you in a bit.”
I went to reception and asked to speak to the duty manager, Asha was very apologetic about the Air Con, but said that she’d send one of her lads round straight away to double check but that it probably couldn’t be fixed, apparently they’d had trouble in that block for the previous month or so and the all the units were being replaced, but not all of them would be done until the day after we were due to leave. I pointed out that it was pretty unbearable so she said to come back at lunchtime and sort a room move out once she’d checked the reservations list.
About 45 minutes later I was still sat by myself at breakfast having eaten, but Katie was nowhere to be seen, her smoothie had got warm and the omelette which was made to order was looking decidedly cold, old, and rubbery. Just as I finished my coffee and was about to go looking for Katie she arrived. She took one look at her breakfast and decided some fruit from the buffet cart would be a better bet. I stayed with her as she ate her fruit, she had a strangely spaced out look on her face which I put down to a poor night’s sleep in the sauna that was our bedroom.
We nipped back to the room and changed for the pool, grabbed some loungers for ourselves and jumped in the pool to keep cool, we each did a few slow laps of the pool at our own pace but after a while we were both lounging in the shade at the deep end. It wasn’t that deep so I could just touch the floor with my feet but as Katie couldn’t she draped her arms around my neck and attached herself to my side with one of her legs loosely wrapped round mine.
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