Last summer I helped my friend move a large decorative pot from one side of her driveway to the other. And it was really heavy.

The backstory is that my friend has no issue letting people see her boobs, flashing to get what she wants, etc, but she had made it clear that she would never let me see anything, so don't ask.

Some eight years after meeting, and I helped her move the large decorative pot as stated. I got a very deep view down her tank top and into her bra. I didn't see her nipples because her bra mostly fit and it was stretchy, but it was very nice to see all that I could see. She stood up and her nipples were poking through her bra and shirt, and I was able to see how unusually upwards they pointed (even in a stretchy bra).

I know she let me get a nice look down her tank top as a thank-you for helping. She could have put her jacket back on or stood differently. It seemed like an accident, but I am certain it was on purpose.

And the way she stretched afterwards and didn't cover up when she saw my staring at her hard nipples...it had to be on purpose.

We never discussed it, and nothing has happened since.

Neighbor
 

Growing up my neighbor used to leave her blinds pulled up. I think it was when I was 16 til I was maybe 19.

Like clockwork she would take a shower, come in, and then walk around her room naked for at least 30 minutes. I swear she had to know. The only issue was that it was on the 2nd floor of their house, so I had to be on the 2nd floor of our house. Which meant being camped in my parent's bedroom window. I sat there w/ a pair of binoculars... every night. It was pretty awesome to be honest.

I set up our old VHS video camera to tape her sometimes too. I don't have the tapes any more. Once I set the camera up on the railing of our deck, so it could record them while I was inside. I heard the wind blowing... I didn't think twice of it. Until I heard a bang. I ran out, and the camera was gone. It fell off the railing and to the ground, maybe 20ft below. I had to tell my parents I was recording the dog and dropped it.

Anyway... I always wonder if she left them open on purpose.
I think she did... b/c she had a sister who would ALSO come in and do the same thing... but she would lower the blinds. Sometimes the blinds would have 1 or 2 slats not straight, and you could peek through and glimpse something good....
but the older sister would eventually pull the string and the blinds would be back open.
So I kinda feel like they knew I was there.

Not sure... funny thing, I am friends w/ them on facebook... b/c ya know, gotta keep in touch w/ the old neighbors as we all get older.
Yet here I am knowing they both were nude and dancing around and that was pretty amazing back then. This would have been in the mid 1980's.. so without the internet or access to porn or such.. you had to take what you could get.
Granted this was pretty sweet.
I forgot to say they were VERY attractive. and still are today....

Friend's mom bathing suit wedgie
 

I had a close friend in high school and his family had a really nice boat for waterskiing and tubing. During the summers I would sometimes get to go with them out on the boat at a nearby lake. My friend's dad was always there because he wouldn't let anyone else drive his boat. And about half the time my friend's mom would join on the boat too.

On one occasion when his mom came out with us she was wearing a sporty one-piece bathing suit as she always did. A typical "mom bathing suit" from the late '90s. Full coverage in the front and back - nothing scandalous about it.

Towards the end of this boat outing, everyone was done skiing and tubing. The boat was idle and everyone jumped into the lake for one last swim before we packed up and went home. Eventually it was just myself and my friend's mom swimming in the lake when his dad said, "ok everyone in, time to go home."

So both myself and my friend's mom swam towards the back of the boat to climb in. She was a little bit ahead of me so she began climbing up the boat ladder first while I was just behind her. And as she climbs up the ladder, I notice her bathing suit is completely wedged up her ass. Both of her buttcheeks are visible plain as day as I'm swimming towards the ladder. And then as she's almost out and standing on the top rung, she pauses and pulls the wedgie out so her bathing suit is back to normal.

I saw the entire thing from her big butt climbing up the boat ladder to her picking the wedgie out. It was quite the sight. And I don't think my friend and his dad had any clue what just happened. Only I had noticed and saw any of it.

When I climbed back onto the boat his mom was wrapped in a towel. We made a brief awkward eye contact with each other as the dad is starting up the boat again to go home. My heart was racing and I'm sure my eyes were widened from what I just saw. I think she was gauging my reaction. For some reason I was feeling a little shy or guilty about what I had just seen in that moment. So I was the first to break our awkward eye contact moment and look away.

I never mentioned it to anyone. I just enjoyed the memory. It was the greatest memory ever if I'm being honest. I've gone back and forth in my mind as to whether or not she flashed me intentionally. Nothing like that had ever happened before or after with her. And she did not seem at all like the type of mom to flash her ass to her son's friend on purpose. She was a very put together woman and it just didn't seem like her personality at all.

But I can't understand how that could have happened accidentally. Her bathing was full coverage in the back and there's just no way she couldn't have felt it being wedged up her butt as she climbed into the boat. And the awkward glances at me afterwards suggested she knew what she was doing and maybe felt like she went too far. I don't know. But the mental image of her ass climbing the ladder and pulling out her bathing suit wedgie was a gift to me that I will never forget.

I just remembered one that was "on accident" but on purpose for sure!

Night before my wedding, I stayed at the best man's house with his wife. His wife was in a thin pj top, but she kept her arms over her nipples the entire time. Bummer.

That night, I slept nude, and I woke up with morning wood and just a thin sheet over me, and my friend's wife came by the loft. It was all open, so she stopped, leaned against the wall, and stared at my tent. Her eyes were so wide.

She eventually left, and I thought she was downstairs, so I walked to the bathroom nude to take a shower. I saw a glimpse of her down the hallway. I am not sure if she was hanging out and waiting, or if it was just coincidence, doesn't matter. I know she saw me, still with my morning wood.

Now here it the accidental "on purpose" part.

Later that morning, I was dressed and leaving soon, and when I went downstairs, she was already downstairs in her same pj top from the night before. But instead of having her arms over her nipples, she was bending over in front of me as much as possible. Like she was looking for so many reasons to bend over. I really enjoyed the view. Super dark areola with pencil eraser nipples, and her mostly flat chest really filled out when she bent over.

We never spoke of it, but I am certain it was on purpose!

A few years later, I was there at night and she had another pj top on. When she would bend over in front of me with her husband nearby, she would hold her top back to the chest, but when she would bend over in front of me without her husband around, she would let her top fall. I didn't see anything that night, though, but I am certain she was trying to show me something. It seemed pretty obvious!