I’ve been traveling to the Milwaukee area quite a bit for work, staying at the same hotel each time.  I’ve successfully thonged every night during the last few visits without incident wearing my green N2N Maverick thong, cock ring and all.  I always wear shorts or swim trunks to the pool and don’t really walk around in just my thong too much but getting more daring of late.  One night the lights were off, which made it very easy to get comfortable.  There are cameras but I’m guessing they aren’t actively monitored or they don’t care.  I always go during “adult swim time” so there are no kids around or anybody else for that matter.  The pool also has windows that face the parking lot and there are poolside rooms, but those are usually unoccupied.  It has been extremely liberating and I think the risk of getting caught makes it even better.  I’ll probably never be bold enough to do it at a busier hotel but this has been a lot of fun.

I love to wear thongs at hotel pools and spas. I have always packed several suits and cover shirts with varying degrees of coverage so that I can select the appropriate ones based on my judgement of the crowd and situation. 

For example :

Early afternoon, crowded pool, lots of children, Hampton Inn - square cut.

Evening, small adult crowd, upscale hotel - thong or rio.

Lately, I have taken a different approach. I pack my one pair of favorite cover shorts and a couple of minimal coverage suits. I go to the pool, select a chair or lounge, remove the shorts and if I sense the other guests will be uncomfortable with my bathing suit, I casually lay a towel across my lap. I let it cover my suit,  but I don’t place it there like I’m trying to hide something. From the side, people may notice I’m wearing a thong. Little by little I let the towel reveal more, or maybe take a quick dip in the pool and not cover myself after drying off.

The point is I wear the suit I want to wear and let other people gradually adjust to me instead of me completely adjusting to then.

I stayed at the Palace Casino Hotel in Biloxi MS before and they have a nice pool kinda off to the side of the casino. I’ve been about 3 times now for quick weekend getaways with my wife and I’ve found it to be pretty good for thonging first thing in the morning when the pool is open. As the day gets going more people come down but it’s a good crowd nothing too bad and depending on when you go, not as many kids as you would think. We like to get there on Saturday around 11 and try to check in earlier if we could. Saturday I have just worn a speedo or bikini at the pool and it seems fine and people don’t really notice too much. Sometimes I’ll fold my bikini to be fairly small on the sides and layout like that all day. Waitresses will come up and take your drink orders and don’t seem to care really. 

On Sunday morning I’ll get out there as soon as it opens and will wear a thong all morning long. This is the best time because most people are leaving the hotel before 11 and the new group of people coming to stay usually don’t make it to the pool till noon or so. The last time I was there I got some good tanning going on my stomach with a traditional thong on and the few people there didn’t really notice. I had a hotel staff lady (manager possibly)  walking directly toward me on the path behind me. I was on my stomach and I really thought she was going to say something to me about covering up. As she approached we made eye contact and I gave a little wave and a morning to her and she waved back saying it’s a nice day today and walked past me inches from my chair. I was relieved that it was all good and she clearly saw I was in a thong. We had other hotel staff walking all around us while laying out and didn’t ever say anything. So overall it was a success and I know I can wear a thong there. I probably would t push my luck when it got more crowded though. 

This past year for work I have been doing quite a bit of traveling and usually I will be in the same city for weeks or even months at a time.  I will usually arrive at the hotel Monday and leave on Friday.

At one hotel, on my initial stay, I asked if they allowed thongs in the pool area. I was given an unusual response of "I'm not sure I have never been asked that before" then she asked "what do you mean by thong?"
I said it was a type of swimsuit, to which she said "if it's a swimsuit you are ok".

Since I was working in the evening, 4PM til midnight, my mornings and early afternoons were free. So the next morning after eating breakfast I decided to go check out the pool area. It was quite nice with 3 pools and a hot-tub. Being early in the day on a Tuesday I was the only person out at the pool. I laid out for a while until I got warm and went to cool off. I assume I must have been being watched on surveillance camera because shortly after getting in the pool I had a girl from the front desk along with a hotel security guard walking out toward me as I was swimming in the pool. 

Then I hear the security guard say "excuse me!" so I turned around in waist deep water and they could clearly see I was not nude, and then she said "I'm sorry to bother you, but it looked like you were naked from the security monitor". With him was the same girl who handled my check-in, so I asked "Is this ok for swimming?" to which she replied "absolutely!"

So for the remainder of my time staying in this city I stayed at the same hotel which turned out to be 4 months. Since I was staying during the week even though the hotel was usually full with guests I usually had the pool to myself during the day, with the exception of the occasional other guests.

The hotel staff usually didn't bother me. Some of the staff actually would have conversations with me when they were walking through the pool area.  They also accommodated me by putting me in a room closest to the pool. Over the weeks I was more comfortable with the hotel, as the staff was more comfortable with me: To the point I would just walk out to the pool in my swimsuit without needing to bring a cover-up along. Over time I reduced my coverage from a thing to a G-string and then finally one day I decided to press my luck and wear a baggie. That day I did bring a sarong to wear in the event it was an issue.

As I was laying my towel out one of the girls who normally stocked the towels and cleaned the pool area was walking past me and smiled and said "I didn't think you could kind anything smaller! but I was wrong!" then she said "wait til I tell the other girls!" Later on that afternoon as I was getting ready to go to my room two ladies walked out as I was wrapping my sarong around my waist and said "leaving so soon?" I said "Yes, but I will be here tomorrow."   

The next morning around 8AM I went to the pool after breakfast, as I had been doing for 3 weeks. Not once has anyone ever been at the pool before me. My normal routine is to grab a towel, set it on the same chair I use, and dive into the pool. Then walk out of the shallow end and around the pool to my chair.
Only today I noticed two chairs next to my normal chair already had towels on them, along with beach bags. I look over I see two ladies sitting in the hot tub looking over toward me. They are the same two ladies I ran into the prior day as I was leaving. Only this time I am wearing a baggie, that when wet is a bit transparent. As I dived in for my morning swim the ladies went to their chairs next to mine. As I came back to my towel soaking wet one of them says "I think I like this place!" and the other one said "Now I understand what they were talking about!"

I later found out that when the ladies called the hotel to book, they had asked about the pool area and if they permitted thong bikinis. They were told YES, they are welcome here. 

Traci, I completely agree with getting to know the hotel staff and being friendly towards them if you plan on wearing minimal swimwear.  I also try to stay in the same place if I'm in an area on repeated visits or extended stays. I have also noticed that some of the residence hotels where most of the guests are working during the day seem to have smaller staffs and especially during the day have fewer people walking around the property.
Last year I visited a hotel that I had previously stayed in a few years prior, and after checking in I went to my room and changed into a G-string before heading to the indoor pool which was right down the hall from my room. As I walked to the pool I passed a lady from housekeeping who did a double take but didn't say anything.  
A few minutes later, as I was swimming laps, the hotel manager walked into the pool area. When I noticed her I stopped and turned toward her. She smiled as she recognized me from my prior visits. I said hello and asked her how she has been since I hadn't seen her in a long time. She said she a a report of a "naked man walking to the pool", and then laughed and said the house keeper might have exaggerated in her story.

I got out of the pool and was standing on the side drying off. We noticed the same housekeeper filling up the towel bins. The manager called her over and introduced me as one of the hotels "preferred guests". Telling her that I had been coming to this hotel for years, and that anything they could do to make my stay more comfortable they will accommodate my wishes. Needless to say I had no other issues with any of the other staff since at that location.

I second Da6772, your complement was just right. 

We all like getting complements on our swimwear choice, when it does not come over as creepy.   So take every opportunity to complement others, but try not to come off creepy. 

We all worry about how other people are judging us, especially in a close environment with strangers, like a hotel pool. 

We know just how heart warming it is to get an hoist complements and approval. So work hard on complementing others, even if it is just a smile and thumbs up in passing. 

I find a warm smile and thumbs-up is the simplest complement, that is not misunderstood, and never comes across as creepy.