Unique Travel Arrangements Pt. 01

this is a fictional story:

I had been working remotely for almost 2 years and honestly, I didn't mind my job. My husband, Greg, and I really needed two incomes. My husband's career was going well, but he was still basically at an entry level position and had accumulated considerable debt from his original stint in college and then deciding to pursue engineering. We were able to pay our mortgage and basic necessities and even tried to save some for retirement, but there wasn't much left for anything else.

My boss, John, was a nice man. Though I had never met him in person, we emailed daily and had several Teams meetings. He was in his late 60s, so when he requested to be my friend on FaceBook it seemed harmless enough. However, only a few hours after, I get bombarded with notifications. He had liked a ton of my photos. When I looked at them, there was a common theme. Almost every one of them was in a bikini at the lake. He even made a few comments like "You should be on a beach somewhere," or "let me take you on vacation."

I made the mistake of saying, "yeah right," with a couple of laughing emojis. It wasn't 5 seconds later when he was messaging me on Messenger. He informed me that he was serious and he'd gladly take me on a vacation. I just responded that I didn't think my husband would like that too much and laughed it off. He said that my husband could come too and sent a laughing emoji of his own.

I didn't think too much about the exchange and didn't feel like he'd crossed a line or anything. I had even forgotten to tell my husband about it. That is until we were watching TV and a Carnival cruiseline commercial came on. My husband said how relaxing it would be to go on a cruise. That's when I told him about the exchange. He jokingly said, "Hell Penny, you should do it. He's just an old man." We both laughed but did continue joking about it over the next few weeks. I'm not exactly sure how, but over time the tone of the jokes kind of changed until finally my husband said "just see what exactly he has in mind; it's not like we're going to actually do anything."

So, with that, we laid the bait. I posted a few more pics of me at the lake and sure enough he commented on them. Nothing crazy, but just said that I looked like a model. I messaged him on Messenger and told him thank you. He sent me a winking face back. I waited a couple of minutes and then asked him if his offer still stood.

He responded that of course the offer still stood. I asked what exactly he was expecting of me. He indicated that he would just like my companionship. I asked what exactly he meant and he informed me that he just wanted me to basically be his girlfriend at times and the details would depend on where we went. I told him that we'd be interested in doing a cruise. He asked if my husband would be going and I said that of course he would. He asked if we wanted him to pay for everything. I asked for clarification, and he mentioned airfare, excursions, hotel before/after, and gratuities. I told him that would definitely be ideal.

Then the conversation took a real turn. He said that I'd just need to be his date for dinner each night date and then sex before bed. I said that I definitely couldn't do that and that I could only do that with my husband. He said that there was another option and I asked what it was. He told me he had an offer and I could take it or leave it. He would pay for everything for the 3 of us. My husband and I could have the days together and then I'd be his girlfriend starting at dinner. After dinner we'd get in the jacuzzi for a soak and then come back to the room. Once there, since I wouldn't have sex, oral would suffice. However, once we're done, I'd still be his girlfriend so I would be sleeping in his bed. I told him that I was worried about being in the bed next to him naked and he told me that I could keep my panties on if it would make me more comfortable. A little taken back by the conversation, I told him that I would think about it.

That was the end of our conversation. I showed hubby the exchange when he got home from work. We shared a laugh before he said, "are you really thinking about it?"

I said, "IDK, should I be?,"

"Only if you want," he said.

The more I thought about it over the next few days, the more it seemed like no big deal. I finally asked my husband if he really wanted to do that cruise. He said, "if you do." and that was that.

I messaged my boss that next day asking if he was serious. He indicated that he was and gave me a date. It was only 2 weeks away. I confirmed with hubby that he could use his PTO at that time and then told my boss that we were in. It wasn't 2 hours before he messaged me all of the details. He already had flights, hotel, and a cruise booked. He then asked my sizes for dresses and a bikini. I responded with them. He then said that he would order several dresses and a few bikinis and we'd pick them out together over Teams and send the rest back.

A few days later, the package arrived. I looked over the things that were sent. Some of them obviously weren't going to fit and some were just a little too much but I knew I'd honestly feel pretty sexy in much of the options. I texted my husband to see if he wanted me to wait until he got home to try them on. He said no and with that, I messaged my boss and let him know they'd arrived. I then got an email with a Teams meeting with just my boss and I titled "company dress code." I laughed a little and accepted the meeting.

Before the meeting started, I laid all of the dresses and bikinis out on my bed. There were 12 dresses and 4 bikinis. Some of the dresses were not too bad but all of the bikinis were outside of my comfort zone. I decided to go ahead and have one of the dresses on before the meeting started. I chose one of the more conservative dresses first but to my disappointment, it was too small. My girls just spilled over the top and if i moved at all, my nipples came out. I chose another of the more conservative dresses and it fit much better. It showed a little more cleavage than I was used to but it was nothing over the top. Just a couple of minutes later my meeting notification went off and I joined the meeting. He wasn't on there yet.

I already had my camera on, so when he joined the meeting, the first thing he said was, "Wow, we're off to a good start." I just smiled, giggled and thanked him. He then asked me to model the dress. I stood up and after adjusting my laptop a few times, modeled the dress. He told me that once we had picked out 7 dresses that I could send him the shoes I wanted and he'd purchase them for me. Only rule was that they had to be super high heels. I thanked him again. He then said it was time for the next dress. I moved just offscreen to change and chose another dress. He expressed his disappointment in a playful way. I explained that I had to because I couldn't wear a bra with any of the dresses he'd chosen.

He laughed and said that must mean they were pretty good. I laughed a little in response. We went through all of the dresses except for the last 2. They were the most revealing so I had been hesitant to try them on. I suggested that since we already had 7 that would work, we didn't need to. He said that he wanted to see them anyway because he'd been looking forward to this. I relented and went to try on the first. It was super thin, not quite see through, but definitely allowed you to see where my nipples were. it was also very tight. Even though I was wearing tiny thong panties, you could still see the strings.

He definitely noticed as well because as soon as I came into view, he told me how breathtaking I was and how he loved my panties. I smiled and blushed with embarrassment before moving offscreen to try on the last dress. It was nowhere near as thin as the one before and wasn't plunging like some of the others. It was kind of a turtleneck with a triangular cutout starting just under my nipples to a few inches below my navel. this left the bottom half of my breasts exposed and also assured I'd have to make sure I was freshly shaven. However, at this time I was not freshly shaven. While modeling the dress he even commented that he believed he saw a little stubble. I was super embarrassed. With that, he told me 5 dresses that he wanted me to wear (including the final 2) and said I could choose 2 more and send the rest back.

He then asked me if I knew what it was time for. I blushed before telling him that I did. I moved off screen and looked at the bikinis. Every one was a g-string or a thong. I had never worn a bikini like that before, let alone in front of someone, and wasn't exactly excited about it. I was nervous enough there in front of one man on the computer in my own home. I chose what appeared to be the least revealing top but when I put it on, it was pretty sheer. It wasn't completely sheer but likely would be when it got wet. It was a black tube top with a matching thong bottom. I reluctantly walked into view and the way he complimented me made me feel more confident. I tried on the next 2 which were basically identical except for color (1 red & 1 yellow) and the fact one was see through like the first and one was not.

Also, both of these were g-strings, so I'd basically be wearing the most revealing clothing item I have ever owned in public. The fabric of the tops was barely enough to cover my nipples. Of course he loved both of them and had me turn multiple times to see my backside which was a little uncomfortable. The final bikini was very nice and you could tell it was expensive. The top was sexy but was bandeau style and offered good coverage. The bottoms were thong but offered much more coverage than the 2 g-strings. I told him that I liked it and that it was definitely my favorite. He indicated that he was going to have me choose 2 and send the others back but I could just keep them all. I thanked him.

He then said there was one more thing. I was confused because I didn't see anything else. However, he asked me to double check the box and when I shook the box, it fell from the paper. It was the tiniest pair of panties I'd ever seen. A red g-string.

I carried them back into view and he said, "I see you found your pajamas."

It took a second to register before I said, "what?" He said that's what you'll be wearing in my bed. I was speechless and I'm sure beet red. He then said it was time to model them. I moved offscreen to try them on. It was hard to imagine anything significantly smaller than the 2 bikini bottoms but these definitely were. As I stepped into view, I could see the approval on his face. As I spun around to model the bottoms, I lifted my TShirt slightly so he could see.

He then said, "you won't be wearing a shirt, so I want to see you in just your pajamas."

I said, "I'm not comfortable showing my breast." He said that was fine and that I could cover with my hands. With that, I faced away from the laptop, pulled my shirt over my head and turned to face it cupping my breast in my hands. After several seconds, I moved offscreen and put shorts and a t-shirt back on. I came back to the computer and we chatted a bit about the cruise. Just before we ended the call, he expressed how he couldn't wait to see more of me. I smiled with embarrassment.

After the call, I decided to go ahead and pack what I could. All the while, the reality of the trip arrangements was starting to hit me. The idea of doing things with that old man was gross, but the idea of "having to," was unnerving. Also, I liked the idea of wearing clothes I'd never wear in real life and the attention that would come with it.

The next week and a half would fly by...