I know this is kinda long, but it is fun to share with you all!
At a cabin resort for a week last week. We were checking in. I was in the check in office while the rest of my family stayed in the car with the A/C. I had to wait forever because a mom and a million kids were buying things at the gift shop, one thing at a time. But I noticed the mom was wearing a very thin t shirt and I didn’t see bra lines.
Eventually, she turned around, and no bra. Just pointy A cups and mis-proportionally large areola just dark enough to see through the thin white t shirt with hard eraser nips. She kept looking at me and smiling. (I later realized she was checking to see if I was looking; it will make sense later.) She was early 40s with the breasts of a 20yo. It was fun to see.
Eventually checked in, and my family got to our cabin, and I thought nothing of the woman until a bit later when we went down to the water.
There were about 20 cabins at the resort, but the two huge-group cabins were at the water. Kinda weird because the beach was for the entire resort, even though the two cabins comprised of one extremely large group of people literally 25 feet from the water made it seem like their own beach, but the beach was for the entire resort. But that turned out to be very good news. Jumping ahead a bit, the two huge cabins had a family of three guys and 8 women. I eventually learned that it was the mom/dad (grandparents), adult sisters (ages mid-30s to late 40s), an adult brother, a brother in law to one of the married sisters, and the wife of the brother. Then there was this 20yo young woman (she said she was a college sophomore). I never totally figured her out. I think she was hired to watch after the dozen or so rather young kids so the adult sisters could get a break, maybe? She literally only wore bikini tops and shorts the entire week. She was really annoying, too. Anyway...going back in time.
When my family walked to the water, I was sitting on a bench because of my tired heart while my family went into the water (I look super fit, but my heart issue keeps me from walking far or swimming at all). One of the sisters of the group pulled up in her huge SUV with her kids (no husband, I guess), and she got out and gave a huge hug to another sister. I noticed the second sister wasn’t wearing a bra. It was super obvious, but not see through like the woman in the office/gift shop, but large enough breasts with long nipples to get my attention...two women without bras in the matter of 20 minutes. Interesting for where I live. You don’t see that often outside of older teens/college age women around here.
The new arrival said, “Oh are we really doing the no-bras-allowed thing this week?” The other sister said, “Yep! Ana said it’s good for us and the best way to relax!” The first sister said, “I guess maybe I will try it one of the days.” The second sister said, “No, all of the days. Even Katie is braless already.”
“Katie? Ya, right. Then she must have a top that goes with going without a bra. She won’t even let her own husband see her without a bra.”
“Nope. A t shirt. Thin, too. You might even say see through.” (I later learned that it was Katie who I saw in the gift shop!)
“What? Really? Her husband would hate that. I don’t believe you.”
“Well, her silly Kyle isn’t here this week, and we won’t tell him.”
“Okay, I guess if Katie of all of us is braless, I can do it, too. I can’t believe we are doing this.”
“I don’t know what the big deal is. We are grown women.”
“You don’t care if your hubs sees these puffy things this week? I will think about it.” (I was hoping she was going to take her bra off right there, but she didn’t.)
“Nope. He will see all of us hanging free. Lucky guy!” (That would be the only male related through marriage there as the other guys were a brother and the dad who I literally only saw twice as he worked on puzzles inside the cabin the entire week. Very lucky indeed!)
Well, because my family spent most of the time at the beach with me sitting on the same bench, and the huge group had their cabins right there, needless to say that I got to enjoy all of them braless throughout the week, too. And none of them had tops that worked braless. Instead, lots of t shirts, tank tops, sometimes loose, sometimes wildly clingy, etc. And for all sisters, they all had very different breast shapes, nipple sizes, etc. The Ana whose idea it all was wore lots of shirts with large armholes. She had very small but extremely saggy boobs that were like thin flaps, but long nips that pointed straight out and sometimes up a bit. I saw into her armholes a lot. She was very proud of her idea to go braless for the week and giggled and brought it up and thanked all the sisters way too often.
I saw the Katie person much, much more than the others. Her kids wanted nothing to do with her because they had the older cousins to look up to, so she kept an eye on them while sitting next to me on the same bench most of the day every day. I talked to her a bunch, too. Like we were instant best friends who knew each other for decades although we had just met. She had a nuts marriage. Even my wife came by and talked to her a lot. My wife loved her. She was fun. Like 6’1” and super fit.
By the third day, I got the courage to tell her that I overheard the conversation of her other sisters talking about a no bra week, and she said it started as this joke last year and only Ana went through with it last time, and how this year they would all do it. She said none of them even packed bras except Sarah (the one who I saw pull up and ask about it...and when I eventually saw her, she had such puffy areola that it was like A cups on top of C cups. She wore a padded swimsuit most of the time to cover up while still following their no bra rule, but I saw her braless in regular clothes a few times). Katie said that she always covered all her skin in long dresses, never showed anything, and looked like a prude churchlady even though she promised me she isn’t, so this braless thing was absolutely enormous for her, and she was loving every moment of it. She said talking to me knowing that I was checking out her boobs through my sunglasses was very liberating for her and saw nothing wrong with it. I told her I wasn’t trying to look that much, and she said go ahead. So, I looked a lot more than I already was. She was almost my height, so I couldn’t really ever see down into her tops, so it was mostly just seeing the shape of her breasts with her nipples poking through that I enjoyed. One of the days she was wearing a sporty tank top that kept slipping, but she had pulled it out and up a bit to adjust it and I saw everything. She said, “I just flashed you didn’t I?” I said, “Yep.” She said, “You won’t believe me if I swear that wasn’t on purpose though.” I told her that I believed her. It was the only time I actually saw them without material covering them, though, with one exception (be patient).
I asked her what it was like having the one guy around who wasn’t their brother as I am the guy who married into a family with a bunch of sisters myself, and she said he stares a lot but she doesn’t blame him. She even likes when he stares but she would never admit that to any of them. She said she has been trying to get him to see more of her on accident but it hasn’t worked out yet. Some of the sisters tease him when they catch him staring, but she doesn’t tease him. I asked if his wife minds him checking out all his sisters, and Katie said his wife doesn’t mind one bit, but she does tease him the most.
Then I asked about the sister in law who married into the group, and apparently she hasn’t worn a bra a day in her life anyway, so she has been rolling her eyes at how the other women have been so giggly about it and is kinda annoyed by the whole thing like it’s this huge thing. I said that I can understand it from both sides.
Then I shared stories about how I am the one who gets seen naked all the time on large family trips and my wife’s family doesn’t care, but it’s always just me, although I have seen some of the women in my wife’s family topless on accident a few times. She said one of the sister’s ex husbands was like that. Often naked. She said it was fun for all the sisters but they never talked about it and they acted annoyed until the divorce and how they missed him running around naked once they all admitted that they liked seeing him on their large family trips. Back when there were more husbands and no kids running around, they would dare the other husbands to get naked, but none of them did, and the sisters got annoyed that their dares to get all the husbands to get naked in front of them never worked. Now there are only two husbands; the one that came with on the trip, and Katie’s who refuses to go because the other sisters call him out on his shit and he can’t handle it. They keep begging Katie to get divorced, but she won’t.
I asked if the only current brother in law does anything like that now, and she said she walked in on him in the shower at a cabin once a few years ago and he freaked out, and she was bummed because she was hoping it would have loosened up the entire group and everyone was upset at Katie for walking in on him, even though it wasn’t on purpose.
She said that she is known as the prude of the group, but when it came down to it, she was probably the most loosened up of them all, but only when her husband isn’t around. I told her she is the only one I saw in a see through top during the braless week so far, and she said yep. The other sisters have been checking their tops extremely carefully in bright light before stepping outside. She said they are boring. She said she brought up strip poker the second or third night and everyone looked at her like she was an alien. I asked if she would really let the brother in law see her, and she said of course she would if it came up the right way. I joked that if they do ever play strip poker to invite me so that there would at least be another guy playing!
Apparently, this no bras week was an enormous deal for them as they come from a background of ex husbands (and current husband in her case) of men who didn’t even want them being in swimsuits around other husbands, which is how the dares of the husbands getting naked started as a way to fight back, I guess. It got pretty deep in a hurry, but it made me understand why these 30-40 something sisters acted like giggly teens when it came to being braless.
Most of our conversations weren’t about this stuff, of course, but these are the most interesting topics that came up, of course. We talked about parenthood and jobs and blah blah blah a lot, too. Mostly those things, but she would hint at or bring up these conversations, so I would be sure to capitalize on it whenever she did!
Near the end of the week, I was invited to hang out with them all while my family was swimming (I can’t swim because of my heart defect), and I was having dinner outside with all of them at once (my own family went back and forth between the group and the water; I didn’t ditch my family this whole week!). And I was very amused by how free they had become by then. Loose tops with perfect nipple views, lots of downblouse views, t shirts, and the brother in law was checking out every single one of them. At one point, his wife was standing by me, and we were poking each other every time we caught him looking down one of their tops. Then Katie came over and took over the conversation. It all wrapped up, then the rest of the evening was spent with my own family after being beaten by the sun all day.
But much later that night, I was out walking to see the stars since I live in the city and I don’t see any, and I saw Katie change into pjs in front of her window, seeing her perfect little boobs with large areola, and her huge bush when she put pj shorts on without underwear. I couldn’t believe I got to see her on the last night, but for some reason I wasn’t surprised, either. Her window was facing the main dirt road of all the cabins, so it was kind of a central area anyway. All week I kinda figured I would see something from someone in that row of bedrooms at some point. I am glad it ended up being her!
The next morning, which was the final morning, my family spent a little bit swimming before leaving, and she ran out to see me and gave me a huge hug as they were packing and about to leave. I told her that I saw everything while on my walk, and I figured it was okay to tell her, and she said, “It was the last night, and I wanted to be as daring as possible, so I changed in front of the window, but it was like 11pm so I assumed no one would see!” I said, “is it okay that I saw?” and she said, “I don’t know. I really didn’t think anyone would see, but I guess it’s my own fault.” She actually seemed upset! I said, “Shoot. I shouldn’t have said anything.” And she said, “No, I am glad you did because I would have wondered for the rest of my life if anyone saw me last night! So now don’t ever forget what you saw.” She gave me another hug and I swear I felt her press her small breasts into me, then she went back to loading the cars. My family was still swimming, but I did watch all of them women load the SUVs with their swinging braless boobs, though!
Needless to say, we are friends on fb now, ha!
My wife came up to the bench while the rest of our small group was still swimming, and she was like, “What are you going to do now? Good thing we leave in two hours! You would be bored if we stayed longer without them here.” I told my wife everything that Katie and I talked about each evening throughout the week. My wife was actually really happy for me. She knows that I like meeting new people and that I get along way better with women, and she knows how much fun it was for me since I can’t do things like kayak, swim, etc like my wife was doing with our own kids (who are now adults themselves), and she knows I would love it if everyone was braless or naked on our own large family trips, so it was a great week!!!
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