What’s some of your “I can’t believe I got to see her naked” moments?
 

Obviously my idea so I’ll start. I went out to the bar with a buddy and after a while he got pretty hammered. I took him back to his place where his wife and the neighbor woman were drinking and playing cards. My buddy passed out pretty much immediately, and I sat up drinking with the 2 women. Somehow, someway we we ended up playing strip poker, I ended up I’m my underwear whole both women were left completely naked. The moment that is burned into my brain is when his wife stood up and walked to the refrigerator and asked me if I wanted a beer. Purposely posing for me. I’ve never seen her naked before or after that night, but the memory will always be there.

Probably my old coworker would be my #1.

My wife and I were at our favorite local nudist resort just enjoying a naked day by the lake. Suddenly this woman walks past us whose face looks very familiar to me. She turns towards me and gives me an "Oh shit!" look; and that's when I realize it IS her. At that point the "cat is out of the bag" and I just smile and say "Hi {her name}!"...

Now the background story. We had just worked together very closely on a project for several months. We never really got close; just cordial. She's a fairly attractive woman, often wore tight clothing; and like any normal guy I sometimes wondered the usual stuff (is she shaven or trimmed, are her breasts perky or is it just the bra, etc...) She moved on to another gig briefly after our project ended. The encounter occurred less than a month later.

Well I got all those questions answered on the spot. Shaven and perky lol! But tbh we pretty much were initially in shock; as she herself clearly couldn't believe she was seeing me with my dick out. But the shock wore off pretty quickly as we both came to terms with the fact that we'd just faced each other completely naked. We introduced our respective spouses and explained how we knew each other; which led to a few laughs. Which helped ease the tension and us adjusting to our new level of "knowing each other" LOL!

Co-worker
 

I've written about this elsewhere on this site, so I'll give the abbreviated version:

I worked with a woman for several months. She was sort of a hippy and wore dumpy, shapeless clothes. I got along fine with her until one day she came into the office and accused me of something (i had no idea what and she wouldn't articulate it). She stopped coming to work after that (she was a contractor) and I forgot all about her until one day I was at the local nude beach and who should arrive but this woman. She was with friends and didn't notice me. I got to see her completely nude. It turns out she had a great body, big bush and hairy armpits. I soaked it all in and then left before i was busted.

A couple of times at the tennis club last summer my hitting partner wore no knickers but only if we are hitting alone, but she said its because in summer its too hot to wear 2 layers around her waist. When we practiced doubles she wore undies every time, and also when we practiced on weekends she wore undies because the courts are full of people walking past us. I loved seeing her cheeks and pretty pussy when we hit alone but I'm straight :p

There are a couple of examples, but this one will be first.

I had a coworker who was gorgeous, late twenties and had short red hair. She kind of looked like Maggie Gyllenhal around the time she starred in "Donnie Darko". She had a pretty cool job, and was also very pleasant. It turns out that she was a part time model and had a modelmayhem account. Another coworker had found out about it, and told me. We kept it to ourselves because we liked her and didn't want to cause problems for her.

I would intermittently Google her name, along with her alternate "model" name. And one day, hit the jackpot. She had posed for Playboy in a "housewives" issue. Completely naked. And as if it could get any better. She also made a video for Playboy as part of the promotion. So, not only did I have a coworker who I had seen naked, but I also knew she had a clit wring, a tiny red landing strip, and her recounting cool sex stories with her husband. That was at least 10 years ago. Good times! :)

I had a co-worker whose daughter would pick her up from work, if mom was running late she'd come into the office. The daughter was drop-dead gorgeous with an incredible figure. One day mom was very excited to tell us her daughter, who had gone away to college, was going to be in Playboy. Sure enough, in a few months there she was, a full page of her nude pics. Mom was not embarrassed at all and a copy of that Playboy was around the office for months.

Piecenick just reminded me of two other personal Playboy stories - one good and one that was kind of a bummer.

The first one was when I was a teenager. I would rent VHS/Beta movies from a particular video store and there was a cute woman who was in her early twenties who worked behind the counter part time. Somehow, it became a discussion in the store that she had posed for a "Girls of [College]" Playboy issue. I don't want to say which one, but it is a Division 1 college football/basketball school. Anyway, I was really looking forward to it, and I finally saw the photo. She was bottomless kind of kneeling against bed, as if she were going to do her nightly prayers or something. Except she had a text book in her hands. She had this full round ass, and it was just pretty cool being about 16 and seeing someone you know partially naked in a magazine. Also, it turned out she was not a regular student but took a summer school class just so she could show Playboy proof that she was a student.

The second one was another coworker (at a different company than the one I described previously). This one really good looking and was a dead ringer for the actress Angie Harmon. Apparently, she told her customer this interesting little Playboy story, and then he (because he was such a big mouth) went and blurted it out and it got all around the company. It was a another College Girls issue. Because of her age and her school, I knew I had the issue. So, I'm flipping back and forth in it, and I don't see any pictures of her in the nude pictorial. So, now I'm going page by page, and I see a picture of her (clothed in t-shirt and shorts) with two other girls from her school. It turns out that Playboy would give you the choice - and different amounts of money - depending on whether you pose clothed, topless or completely naked. So, she wanted to be in Playboy, but not get in trouble. God, that was so disappointing, but I had already had more than my fair share of good luck.

Emily4- "...A couple of times at the tennis club last summer ..."
 

Sounds like an exciting experience for you both. An ex-gf of mine liked to dress like your friend- little tennis skirt with pleats, no panties at all. She never had an audience other than me, but we played often on public courts and she would roll up the waistband of her skirt until her bare pussy was constantly exposed, then play for an hour or so. I still have memories and photos of those times- very fun!

A friend in England had a sexy wife who took tennis lessons from a younger instructor, and he sent me photos of her on the court with him for several lessons, with her naked ass clearly on display even from a distance. It was never clear who enjoyed it more- her, him, or the instructor!

Every minute of my college's naked runs fits this thread. Saw tons of hot girls I knew naked. So much more exciting to me to see the cute girl from class naked than a random porn actress online.

Spencer tunick
 

I did a Spencer tunick with my gf and her best friend.
It was incredible to see her friend naked