Favourite braless situations?

[cuck4annie]

Bottom pic is for me tonight, you have to watch...

[gbdick]

Please enjoy it. Cum hard for me.

[gbdick]

I want to tell you a story about our accountant at our business, Ann. Ann lives with us now in our big house in the woods. We all ride into work everyday. If you've not followed my exploits, I'm the 60 year old hotwife that fucks BBC while my hubby watches. For 10 years now I've kept his little useless dick locked in a tiny steel chastity cage. It's not big enough for me to feel anymore since I've been taking great big cocks up my pussy. I haven't worn a bra since I was young. I like them free so I can tease men with them. (I rarely wear panties either. They just get in the way.)

Ann came to us 8 years ago, out of college, to apply for a job. Ann was a great accountant so we hired her. Poor dear was a flat chested nerdy frumpy girl with thick glasses. I decided to make her my project. She was enamored with my husband, the CEO of our business. Hubby is good looking and doesn't look his age. She was of course unaware that hubby's dick was safely locked away in a steel chastity cage. After a while I thought she might might be a little taken with me too. I always dress business sexy, skirts a little too short, thin somewhat unbuttoned cotton blouses thin enough to see that I'm not wearing a bra and of course thigh high stockings and/or a garter belt and high heel shoes.

One day she was looking at me and just for fun I got out of my chair with my legs spread while I stood up. I thought her eyes were going to bug out. She saw my pussy alright. I kind of thought she might be a virgin and sexually inexperienced and I found out later I was right. As I passed by her I whispered, "You like what you see, baby?" I heard her breathing hard and I knew I had her. Before the day was through I had her licking my pussy in my office. It was Friday so that night I invited her back to our house in the woods to spend the weekend. By Sunday my husband and I were licking her pussy all of us naked by the pool. She desperately wanted my husbands locked up dick in her to take her virginity but I would only unlock him and let her suck him off, which was a real treat for him. I later took her virginity with my small strapon. She loved it and had several orgasms. My poor hubby wants her pussy so bad. It's the perfect size for him too, small and tight. I'll never let him fuck her. He gets to lick her pussy when she wants it and sometimes I let him use the small strapon over his cage to fuck her. That really fucks with his mind.

Ann came to live with us. For the last 8 years she has helped with our household chores, and is a good cook. Since that first week I've changed her wardrobe. I had her ditch the frumpy bras and panties and start wearing sexy clothes. I got her eyes fixed, got her nails done and pussy waxed. (That's a good story too) She was my project. A new hair style, makeup, and eventually big stripper boobs so she has something to show under her thin blouses. Now she's a lot like me, I think you would say, a walking talking wet dream. Guys are always hitting on her but she's not allowed to take them up on anything. She is in love with me and my husband now so we keep her satisfied. Our circle of hotwife friends accepted her as one of their own so she's very happy with us now. Someday I've promised her that I will introduce her to BBCs so she can take over for me when I get to old. I think she will like that.

Here is a picture of her that she was nervous for me to publish, her first nude picture. She begged me not to show her face so I didn't. Hubby took it. This is what hubby eats when he's not eating mine. I know this will turn her on Isn't she sweet?

[Fred163]

A good friend of my wife invited us for a short visit and drinks. There were three other couples present, and the conversation was in full swing. My wife was wearing tight jeans and a short-sleeved denim jacket, which was buttoned up, so you couldn't see what she was wearing underneath. As the conversation progressed, she opened her jacket, and I heard her friend call out, "What's that amazing thing you've got there?" Then my wife was surrounded by all the women, holding her jacket wide open. When she turned to me, I saw why everyone was so amazed.

She was wearing a black, see-through blouse and nipple jewelry: nipple clamps and a chain that hung between her full breasts. Now the husbands also took notice and surrounded her, shouting in unison that their wives needed something like that too!

[Digitalzoom1]

Way back when we were in our 20s we went on a weeks holiday in GT Yarmouth, the kids were 5 and 6 years old, Maggie put a white top on , it was fairly tight especially over her 38 c boobs, it had a floral pattern on it each flower was a small hole in the centre and the petals were also holes, I looked at it and said to her it would be a sensation if she took her bra off, I didn't really expect her to do it but she came out of the bedroom just before we went out for the day along the front at Yarmouth, she had taken me at my word and removed her bra, I noticed she was attracting attention at times, we decided to visit the model village and as we stood in the queue the guy in front of us kept turning round and chatting to her, as I stood behind her I couldn't see why until that is she turned to speak to me and I could see her left nipple was making a break for freedom though one of the flower centres, it lined up perfectly and a good bit of it was protruding out and it really was very very obvious, she said later that it had been like it most of the time we had been out , it stayed like it most of the day as no matter how much she put it in it just came out again, she gave up and a lot of people had a good look at her nipple.

[Another Again]

in our 20's, a group of a dozen of my friends and partners went on a camping trip to the beach. Was early spring, so quite cold. Super shy fiancé was getting to know my friends.
The first morning, a bunch of us decided to go swimming. fiancé was keen. we were in our tent getting ready and she relaized she had forgotten to pack her bikini top, so she couldnt swim. we left the tent, and a friend's gf said she could borrow her rashvest top, so she grabbed it and we both went back inside the tent. she put the rashvest on and looked at me and asked "is this ok?" hinting that she was braless and did it look too obvious/showy. it looked totally fine, it was quite a thick top, so i told her it was 100% fine.

we all walked to the beach. it was 9 male friends and i. we all had towels around our shoulders because it was quite cold.
we get onto the beach and drop our stuff. walking to the water, i can tell fiance is a bit self conscious being the only female.

The water is freezing! we all walk in at different speeds. i run ahead and dive under.
we are out chest deep and chatting away. a large wave comes and some of us swim and catch it.
as we are walking back out, another one comes and she catches it.

standing chest deep again, i notice a few of the mates keep turning and watching her walking back out. when i looked, i saw her rashvest was clinging to her like paint. you could clearly see her body. her A-cups were clearly outlined, and her large nipples were poking out so far. so much detail. was crazy. she had no idea. was walking back out rubbing the water out of her eyes with no idea at all.

we swam for ages. catching multiple waves. i could see the friends absolutely loving it. they were grinning at me.

i still have no idea if she noticed at all, but would be very surprised, as she is super shy and self concious.

[mikeinluv]

Many years ago, there was a newly hired receptionist named Barbara that caught my eye. She was a very brassy and trashy redhead, a bit dumpy but very attractive. We flirted back and forth and within two weeks I had her bedded in a nearby hotel after work.
Though she was married, she told me her husband was a fat loser, and she needed more than he could give. Besides her trashy looks, the thing I enjoyed most about her was her big, soft and saggy titis. i loved the way they jiggled when she walked, the tops of her tits rippling above her bra that was having trouble containing them.
Before we fucked in the hotel room, I had her wear just a blouse and heels and had her walk around while I masturbated watching her. Her tits jiggling under the blouse had me ready to cum and she loved teasing me.
One day in the office she surprised me by removing her bra in the bathroom and calling me over to the reception desk, where she proudly leaned back and showed me her bold display. The blouse she was wearing was very thin and her titis and nipples we fully on display. I was a bit shocked that she would do this, and I wasn't the only one who noticed, as many of the other men in the office found excuses to stop by and chat.
We both managed to stay late that night and with no one else around, I managed to take a few shots of her in that very top.

[512KenStron]

Originally Posted by mikeinluv

Many years ago, there was a newly hired receptionist named Barbara that caught my eye. She was a very brassy and trashy redhead, a bit dumpy but very attractive. We flirted back and forth and within two weeks I had her bedded in a nearby hotel after work.
Though she was married, she told me her husband was a fat loser, and she needed more than he could give. Besides her trashy looks, the thing I enjoyed most about her was her big, soft and saggy titis. i loved the way they jiggled when she walked, the tops of her tits rippling above her bra that was having trouble containing them.
Before we fucked in the hotel room, I had her wear just a blouse and heels and had her walk around while I masturbated watching her. Her tits jiggling under the blouse had me ready to cum and she loved teasing me.
One day in the office she surprised me by removing her bra in the bathroom and calling me over to the reception desk, where she proudly leaned back and showed me her bold display. The blouse she was wearing was very thin and her titis and nipples we fully on display. I was a bit shocked that she would do this, and I wasn't the only one who noticed, as many of the other men in the office found excuses to stop by and chat.
We both managed to stay late that night and with no one else around, I managed to take a few shots of her in that very top.

The story details of your experience are great but having photos to show are what makes it so exciting!!

Thanks for sharing all of it!!

[dnice82]

Originally Posted by mikeinluv

Many years ago, there was a newly hired receptionist named Barbara that caught my eye. She was a very brassy and trashy redhead, a bit dumpy but very attractive. We flirted back and forth and within two weeks I had her bedded in a nearby hotel after work.
Though she was married, she told me her husband was a fat loser, and she needed more than he could give. Besides her trashy looks, the thing I enjoyed most about her was her big, soft and saggy titis. i loved the way they jiggled when she walked, the tops of her tits rippling above her bra that was having trouble containing them.
Before we fucked in the hotel room, I had her wear just a blouse and heels and had her walk around while I masturbated watching her. Her tits jiggling under the blouse had me ready to cum and she loved teasing me.
One day in the office she surprised me by removing her bra in the bathroom and calling me over to the reception desk, where she proudly leaned back and showed me her bold display. The blouse she was wearing was very thin and her titis and nipples we fully on display. I was a bit shocked that she would do this, and I wasn't the only one who noticed, as many of the other men in the office found excuses to stop by and chat.
We both managed to stay late that night and with no one else around, I managed to take a few shots of her in that very top.

very sexy! hope you have more of her to share

[Gnome72141]

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!!!