When I was in school, the last year I lived in a big house off campus with five roommates, 4 girls and a guy. My roommate Hannah was especially open with nudity around the house, so I had seen her boobs a couple of times, and neither of us seemed to mind too much. She was a short, attractive girl with a beautiful figure, long hair and really nice medium sized boobs -- but our vibe was primarily very good platonic friends. I inferred she was actually more curious to see me in a similar state, hinting we should go skinny dipping sometime, but she never asked outright.
In one of our last days on campus, another one of the roommates, Sophie, was house-sitting for a professor in town, in a big two-story house with a pool in the backyard. Hannah's hometown best friend Maggie was also visiting for the day, a very cute redhead who I confess I had fantasized about seeing naked several times. One day, Sophie invited us over to swim in the pool, and we all brought our suits and some food for lunch. We swam around for a bit as on any normal occasion, then Sophie reminded us she needed to leave for work, but we were welcome to stay at the house as long as we want, utilize the pool, and enjoy the great weather.
A few minutes before Sophie left, I actually needed to skip out to grab something from a friend who was leaving for the summer. So I said "be right back!" and my way back down the driveway, when I heard Hannah ask Sophie: "would it be ok if I got nude?" I wasn't sure of Sophie's response; there were houses on either side, and while the yard was fenced in, second story windows were surely visible. I tried to nonchalantly glance over the fence as I walked down the driveway, but nothing was visible.
Needless to say, I rushed to meet my friend and then right back again as quickly as possible, probably returning 30 minutes later. I opened the gate to see Sophie had left (alas, I would've loved to see how she fit into this vibe) and both Hannah and Maggie were treading water in the deep end. Hannah, very self-confident but always emotionally considerate, shouted, "hey there, we're not wearing our suits anymore, just so you know!"
I responded without hesitation, "do you mind if I join you?" Both of them shook their heads, so I walked up to the side of the pool, stripped off everything I was wearing, and jumped in next to them. The vibe was immediately fun and playful, and we spent a while just swimming around talking, then went to the shallow end, where I noticed the girls were careful about how much showed over the top of the water. A couple of times, both of them propped themselves up by the elbows on a float but were careful not to expose their boobs.
This ended when Hannah suggested we all try handstands in the shallow end. Maggie and I started deeper, and our genitals were just barely covered by the water, but Hannah went straight for the shallowest part. She flipped her feet out of the water and held the pose for a long time, her very hairy bush exposed, spreading her legs as she fell down. I was surprised by her confidence but liked what I saw if I'm being honest, and it emboldened us all. Several minutes later, Maggie got out of the pool without covering herself at all, showing very lovely smaller boobs which fit her slight frame and a gorgeous pussy with just a bit of trimmed red hair covering it.
Soon, we discovered a basket of toys like snorkels, masks and diving darts and we all got into the pool and spent the afternoon playing like kids. It was so fun, and I got a bit of a thrill from several circumstances like Maggie bending down to pick something up, her pussy exposed from behind, or Hannah laying on a lounge chair with her feet towards me and spreading her legs to talk to me face-to-face. It was one of the first of many times I've hung out with close friends nude, which I think inevitably gets you closer and more carefree, and I was also slightly turned on by being a guy allowed to hang out with two old girlfriends completely naked.
Hannah recently got married, but once she shared a post to close friends asking if anyone knew good local swimming places (an area where I don't live anymore). The picture was her at a lake, nude, from behind. I responded with "How about the professor's house with a pool?" and she responded saying how fun that was. Nice to know it's remembered equally fondly
