Glass bottom pool
 

I remember back in my senior year of high school back in the 80s, our senior class took our senior trip on a charter bus from Massachusetts to Connecticut to a sort of run down country club that specialized in large group outings. There was a weird pool that was considered “glass bottom” but most of the glass panels were on the side. Some of the girls in the pool would pose sexy and in some cases flash near the glass panels beneath the water surface. Does anyone remember anything like that?

Where in MA are you from? I'm from Norton but I don't recall any resorts in CT with glass sided pools.

Holliston. The club with the pool was in Moodus CT and has been long since closed.

We had the Glass Pool Inn & Casino!
 

This place was in Las Vegas at the far end of the main strip and close to the Airport. It was kind of higher up on a hill and the Pool was located in the front side facing the street. That front side had a Glass wall so anybody driving down the street or walking on the sidewalk could see those inside the Pool.
The women as far as I remember could only be Topless but many went fully Nude! We had many fun times in that Pool and Casino too, I know that I have plenty of pics somewhere that we took in and out of the Pool.
They had knocked down the entire place many years ago and now it just vacant land, but the Good Times are still talked about today!
;)

Better still - doing subaqua pool training here in UK you could often see the ladies who were swimming above to keep up fitness levels have loose fitting costumes / malfunctions and swim along blissfully unaware for many lengths of the pool.

We haven’t been to Vegas for quite a few years now, I understand there’s less topless pools now unfortunately. Used to be a lot of really nice pools that allowed topless, was a fun place. Last time I was there for a conference, it seemed to me like they tried building too much on the strip. Just to packed in now.

I can only think of 2 that still allow Topless!
 

Sometime ago, they went for the Family deal trying to get Adults to bring the family or kids along! That really didn't pan out for them so they all just about put a stop to that now!
There are still plenty of Strip joints and Nude or Topless BAR's still. Some of our favorites have either Contests or Amateur hour where your able to get your wife up there to show off her Charms or enjoy seeing some of your neighbors too! lol
;)
Besides that the wife is able to walk out with a FREE T-shirt, that tells she showed her tits at "Cheetah's" :)

My friend goes to Vegas frequently and goes topless. There are still lots of topless pools, but it's common to have restricted hours now, like "topless until 11am" or "topless after 6pm" type of thing. And they are usually 21+ now, too. And my friend says a lot of time she is the ONLY one topless, which makes her slightly uncomfortable.

That is good to know, outside of Vegas I doing think there are a lot of topless pools at resorts (aside from South Beach in Miami maybe). It does suck when there are very few women topless. Toplessness is contagious, women are certainly more comfortable doing it when they're not the only one!

In Key West but the ladies remove their tops at the pools but no glass sided pools