Favourite braless situations?

[hbctrapper]

A month into dating this one girl, we went to the wedding of one of her friends. At this point we had made a lot, but so far clothes had stayed on. On the way back she was complaining about the bridesmaid dress being uncomfortable so she through a big t shirt on over top and undressed it, till she was wearing nothing but her underwear and that t-shirt. Her tits were an E/F cup and she was on the slimmer side of average, so her boobs were obvious in the shirt especially with the seat belt that kept working its way between them. The AC was also helping my situation as it was blasting right on her, but I wanted a little more action. So I told we could take a short cut back through the national forest. That route gave us thirty minutes of super bumpy dirts roads and her tits were bouncing all over the truck.

A couple weeks later after we had become a bit more familiar, she asked if I picked that bumpy road on purpose and I came clean. For the next couple weeks that we dated she joked about it and one road trip she took her bra off for the entire trip, though unfortunately it was mostly smooth, paved roads.

[fattykathy_jax]

Is it wrong that my favorite situation to be braless is around family? I am 46DDD, low hanging breasts due to my weight. Family seeing me like that is very embarrassing, but also exciting.

[Naddy3]

Originally Posted by hbctrapper

A month into dating this one girl, we went to the wedding of one of her friends. At this point we had made a lot, but so far clothes had stayed on. On the way back she was complaining about the bridesmaid dress being uncomfortable so she through a big t shirt on over top and undressed it, till she was wearing nothing but her underwear and that t-shirt. Her tits were an E/F cup and she was on the slimmer side of average, so her boobs were obvious in the shirt especially with the seat belt that kept working its way between them. The AC was also helping my situation as it was blasting right on her, but I wanted a little more action. So I told we could take a short cut back through the national forest. That route gave us thirty minutes of super bumpy dirts roads and her tits were bouncing all over the truck.

A couple weeks later after we had become a bit more familiar, she asked if I picked that bumpy road on purpose and I came clean. For the next couple weeks that we dated she joked about it and one road trip she took her bra off for the entire trip, though unfortunately it was mostly smooth, paved roads.

I'm always looking ahead for bumps in the road and will glance at the wifey to see her tits bounce or jiggle, even though in bra and top

[Gnome72141]

Yesterday, the 19yo down the street was walking to the creek to get her younger brothers. She has HUGE boobs and is very thin, looks way younger than 19, etc.

She had some weird brownish swimsuit thing on that wasn't lined. Nips poking out a mile. Boobs softly jiggling the she was in a slow-motion porn or something.

People were walking the opposite way, and she looked down then put her arms over her boobs. But when she got to me she uncovered them (I am sure it was just coincidence; she wasn't uncovering them just for me). I am normally not into women younger than 30 nor huge boobs, but I looked. Very lovely moment.

[jiinx81]

I got a great story from yesterday. DW and I were at a restaurant at lunchtime for their $6 burger Monday special. We were seated outside on their patio, near the door to the main part of the restaurant. The only other party on the patio was a group of friends who looked to be in their 20s, mixed genders, ages and body types. They were having a rollicking good time until an unexpected shower started. I had to run to the car to roll up the windows, and when I came back the whole group was going indoors. One of the crowd as a tall, lean beauty who was on the upper end of the age group - maybe near 30.

When I first saw her coming toward me I thought that she wawsn't wearing a bra because her nipples were very prominent under her thin yellow top, and her tits were gently swaying as she walked. As she got closer, I changed my mind because I could see something other than flesh pressing through the top, and I decided that she must be wearing one of those "why bother" bras that hide nearly nothing.

But as she got within a couple of feet I realized that I was looking at her pierced left nipple and a bar that adorned it. No piercing on the right one that I could tell. I'll bet she was a C-cup, with just enough sag to match her 30-ish looking face. She had kind of dirty-blonde hair worn shoulder length. I loved it that she was so casually dressed in this large group of acquaintances. Too bad they went inside before that thin shirt got soaked.

(Took me a while to get to 100 posts, but I don't post fiction and I only faintly remember the hotter parts of my life pre-sobriety.)

[Rachd]

Originally Posted by Macmmot

It's your body and your life. Do what makes you happy and to hell with what your mother thinks

Thanks haha. I guess my mom just doesn't know how to say things nicely. Like I said I wasn't with a hundred people. Just didn't see the point big deal to just walk my dog. Thanks anyway 😁

[rold63]

Originally Posted by Rachd

Thanks haha. I guess my mom just doesn't know how to say things nicely. Like I said I wasn't with a hundred people. Just didn't see the point big deal to just walk my dog. Thanks anyway 😁

She's just looking out for you but a lot of parents like to blow things out off proportion. It definitely does sound like she doesn't know how to say things nice, at least in that moment.

[Rachd]

Originally Posted by rold63

She's just looking out for you but a lot of parents like to blow things out off proportion. It definitely does sound like she doesn't know how to say things nice, at least in that moment.

Thanks. I think that's what it is

[Gnome72141]

Originally Posted by rold63

She's just looking out for you but a lot of parents like to blow things out off proportion. It definitely does sound like she doesn't know how to say things nice, at least in that moment.

Ya, I can relate. For example, I am pro-breastfeeding, pro-free-the-nipple, etc, but for some really strange reason when a friend of mine was trying to nurse her baby and her nipple came into full view of a handful of people, I made some really off-the-wall comment that was intended to be nice but came out really, really mean and hurtful. I still feel guilty about it and it was over 20 years ago.

I guess I didn't know what to say because I was trying to be sincere, yet I didn't want people to think that I was a perv enjoying the view (even though I was), and I knew that my ex-wife at the time was jealous that I saw another nipple and she was going to take it out on me later (she was abusive), so the words that came out in that split second were not very nice.

Another example, when my sister and I were younger, I remember her boob falling out of her swimsuit. No one saw but me, but I knew she would be incredibly embarrassed if anyone else saw, so I let her know about it before anyone else knew. But, because I was scared of her getting mad that I saw it and I didn't want her to think that I was enjoying it, I made some stupid comment that came across as totally mean instead because I had to think up something in a split second.

Both of these incidents I still feel badly about and are not my normal character at all; not even close, but those are the moments that people remember, unfortunately.

[jimmybob69]

I'm no psychiatrist but I can tell you this. Those two incidents probably bother you more at this time than they bother the ladies involved.
In any case, may I make a suggestion.
You have let the thing with your sister bother you for a long time. I assume you are still on speaking terms with her. Give her a call, tell her that you thought of the event and are embarrassed by way you acted when you were younger and stupider, and ask her if she remembers it and, if so, how she feels about it. I would guess she doesn't remember, but if she does, apologize and get rid of it.
If she doesn't remember it, your in the clear.
If she does remember it, she will probably laugh it off and she will appreciate the fact that you even got to that point.
I learned a long time ago that sincerely apologizing works every time.

If it works with your sister, you could try the other lady.
Good Luck