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 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."
