I would encourage reading earlier chapters.
My plans for an out-of-town trip so Janet could show off more of Lisa's wardrobe came together much faster than I anticipated. Just a few days after floating the idea a colleague from my firm mentioned that he had a client who would be opening a new boutique hotel on a Caribbean Island and was planning a soft launch in three weeks. He was offering free lodging for volunteer guests who were up for some time at the beach in exchange for being willing to provide feedback and would be tolerant of staff in training. Needless to say, I checked out the facility and the area online and logged in to reserve a spot using the courtesy promotion code my friend had secured.
The next steps were a little more challenging, first, confirming Janet was available and willing to follow through with what had been a casual offhand comment, and second, seeing if we could arrange babysitting, house sitting, dog sitting, vacation time, and flights on a very tight schedule.
As I perused photos the from the resort's website and the local area, I had visions of Janet in tiny bikinis enjoying the beautiful beaches. I printed out the reservation confirmation and a few photos of the facility with plans to spring the surprise on Janet. It was exactly a week since I had last mentioned Janet modeling more of Lisa's wardrobe. Trying to act casual, I nonchalantly told Janet, "I am really looking forward to our getaway weekend so you can model the rest of Lisa's wardrobe somewhere where the weather is warm, and no one will know us." Then I handed Janet the reservation and resort photos and anxiously awaited her reaction.
Being this spontaneous was a little atypical for both me and Janet but then again, her parading around in sexy clothes and blonde wig was also atypical. Needless to say, she was surprised, perhaps a little excited, then anxious as she recognize this as something of a dare to wear sexy outfits in public.
"Are you serious? It's so soon, what about the babysitter? Do you really want me to wear Lisa's clothes in public?" Janet responded.
"Yes, I've tentatively arranged babysitting for the girls and the dog with your parents, we'll only be gone four days. And, yes, I want you to only wear items from Lisa for the whole trip. Once we get through airport security you to change into something from Lisa's secret closet and not wear any of your own clothes until the flight home."
Janet blushed. "Yes, I want to go but I need to think about that condition. I'll have to go look through those wardrobe boxes again to see if I can make this work."
"I think you should make it work, after all, the extra income from Lisa's apartment will pay for the trip and your wardrobe is from Lisa so just don't worry about it and dress like Lisa for the trip. There is no such thing as too sexy on a Caribbean Island."
"I know there is no such thing as too sexy around you but how about in public around others? You won't be embarrassed? Janet questioned with a nervous smile.
"Embarrassed, heck no, I'll be proud, perhaps a little anxious and excited."
"And what it other guys get excited too?" Janet teased.
"I'd be disappointed if they didn't. I replied.
The next day Janet reported that she had sorted through the wardrobe boxes. "I'm dieting for the next three weeks if I am going to be wearing those clothes for four days."
She refused to let me see what she was planning to bring, responding to my pleas with the response, "Just remember this was your idea."
Needless to say, I was anxious and excited but sufficiently busy trying to get ahead on all my work so I could enjoy the time off.
Our interactions reverted back to our prior routine, no new outfit modeling for the next three weeks. We did learn a little bit more about the resort and explored a few day trips options. Our flight out was on a Thursday afternoon with a scheduled return the following Tuesday morning.
As we headed to the airport, I told Janet that she looked great, and it was visibly apparent that she had lost some weight. "Ten pounds." she proudly reported. "And I have a change of clothes in my carry-on for when we get onboard."
I was a little surprised she hadn't pretended to forget or push back on my now three-week-old request to wear only Lisa's clothes as soon as we were sure no one would recognize her. As I loaded her luggage the two suitcases seemed a little much for a short trip but I caught myself before saying anything, remembering that she was bringing items from Lisa's wardrobe so the more items I got to see the better. We did the usual inventory to make sure we had tickets, passports, phones, wallets, etc., kissed the kids goodbye, scratched the dog behind the ears, and thanked my parents for volunteering to babysit.
As it turned out, we recognized a couple from our daughter's brownie troop as we boarded the plane. I relented to Janet's request to forego a change of clothes until we got to Miami to transfer flights. It was perhaps a good thing, as Janet approached our boarding gate from the ladies' room at the Miami terminal she was striking. A tight short white miniskirt, delicious toned legs, cute sandals with three-inch heels, and a yellow, snug tank top. She was wearing her shy innocent smile but with enough of a grin that signaled she was well aware of how hot she looked.
After we settled in our seats I happened to notice, thanks to the neckline and generous armholes in the tank top, that Janet was wearing a tube top underneath. I thought it looked familiar. I turned to Janet and whispered, "Isn't that your tube top?"
Not grasping the implications of my question, Janet responded, "Yes, it works well with this top."
"But you committed to only wearing Lisa's clothes."
