We've been to Hawaii, going to 4 islands and multiple beaches. Another good place to sun topless, right, but no. Her tops stayed on like she used glue. Another sexy spot wasted except for the fun we had in the rooms.
But there is something about the Caribbean. We went to Key West and of course started beach shopping. We started with the main beach but there were too many people and a possible gay undertone, not that we care about gays one way or the other. We had a car so drove to a more quiet part of the same beach, approx. 1 mile or so. We had beach chairs so set up halfway to the waterline. She had on her coral and peach bikini with the halter top. I love it since its sexy on or off, more later. Now I know Key West is not technically in the Caribbean but maybe the Caribbean effect is still in play. We were enjoying the scenery when it came time for more sunscreen. I did her back and then she loosened the halter ties around her neck so that we wouldn't get sunscreen on it. I did her upper chest as she held onto the ties. I finished and wiped my hands. She however didn't retie her straps. They stayed loose which made her top loose also. She then folded down the straps over her breasts-not wanting a tanline. I'm a voyeur (aren't we all) so was having fun keeping an eye or two on her chest. She would shift position at times and of course so would her top, showing the brown of her areolae sometimes. In addition, she needed to adjust her top for modesty sake. Have you noticed about many ladies at the beach, adjustments to their top or bottom start with them pulling the garment out away from their body first, then tugging it into the proper location. I've seen nipples and labia at times. Makes you watch for that. So the little lady would move things around thereby flashing nipples. We were at first alone but then I saw a man under a shelter about 50 'from us-how long he had been there I didn't know but suspected he got a good view or 2. I wasn't jealous but turned on a little. What is it about having your wife show her tits to strangers? We stayed another hour or so and then left. The man was still sitting there.
But now to the good stories. We decided to go to an all-inclusive in Cancun. We checked in and went to the room. It was on the back side and had a great view of the dumpsters. Not good, not good at all. Back to the front desk we went and complained. We were able to upgrade to an oceanfront room, about 7 stories up. It was on the corner of the floor with a view to another hotel on the right, the beach just below us and a pirate ship on the left. A channel ran along the left side( where the pirate ship was moored) and across the channel were more smaller hotels, maybe 3 or 4 stories. The first day was for eating and resting. The next morning was different. I brought a spotting scope(60 power) so started checking things out. I looked across the channel to the beach in front of a hotel. After some frantic focusing boobs began to appear. At least 6 ladies were sunning their tits. Great view. Of course I had to tell my wife. She was skeptical at first but couldn't deny her eyes in a minute. Then to the beach down below. One young girl(25 or so) was kayaking by herself. Her man helped her get started and then away she went. She went out 50 yards maybe and then took her top off. She would come in toward shore , put her top on and then go back out, taking her top off. My wife couldn't stop watching. We had to stop and go get breakfast. Then to the beach. Upon getting down to the beach, we decided to go to the right. We walked a short distance and had to actually walk around a fetching lass topless as well. We found a place and lo and behold, there was a black couple behind us with her topless. The reason I mentioned these was the effect it was having on wifey. She didn't go topfree but of course hated tanlines on her boobs so untied her top straps and rolled down her bra tops as much as she dared. I couldn't see how the top stayed up at all but it did. I finally was hoping for a stiff wind, a sneeze or just anything that might cause a revelation. No luck.
All quiet for 2 days but one afternoon we decided to take a double kayak out. We hadn't gone 100 feet or so when she untied the top straps on her bikini, and then pulled down the two triangles, letting her boobs free. All was great until a guy on a jetski started getting close. She still wasn't completely comfortable being topless so up came the top. He would make a swing in front of us and go back to the beach, at which point down would go the top. She repeated this several times until finally we were out so far that he left us alone and she could relax. Alas time came when we had to go back. I asked her about paddling by the hotels across the channel. To my amazement she agreed. I don't know if anyone saw the show but they could have. She was getting confident but unfortunately we left the next day
The next time happened some 10 years later. We wanted to go to the islands so found a spot in Punta Cana at an all inclusive adults only resort. She wore some sexy outfits to dinner. The beach and the pool saw her string bikinis or the coral-peach halter of which I've already introduced. Our room had a balcony which overlooked the pool just below. After 2 days at the beach, we decided to give the pool a try. I will say we were a little shy being a few years older than the crowd. However we were accepted easily. The booze flowed freely and the people were friendly, especially a mid 30s couple. Finally everyone got worn out from the sun and the booze and the party adjourned.