Naked pranks, accidental nudity and other funny naked/sexy stories
 

I found a couple threads that had similar themes but not quite exactly. Just a thread to share funny stories that involve nudity and sexual situations. I’ll start with one but I have a few to share and look forward to reading others.

When I was 18 I went to my Greek friends house for a pool. Her best friend, Jenny was over. They were both also 18. A day with two young pretty girls in bikinis? Sign me up. It was sunny but not the warmest day so we went to the heater and tried to figure out how to turn it on. Suddenly Jenny screeched and ran back to our seats exclaiming there was a mouse. I looked around and sure enough found it, however it was dead. Probably killed by their cat. I got the heater working and we swam a bit but it took so long to heat up it was chilly and we decided to spend our day poolside rather than swimming.

After lunch Jenny laid on her stomach and undid her top to prevent tan lines. My girlfriend at the time gave me a “watch what I’m about to do” look. She crinkled her napkin up and tossed it onto Jenny’s back. “Here’s that dead mouse!” Obviously she would never have actually done that but Jenny’s instincts and extreme fear of mice kicked in before reason. She shrieked and stood up swiping and swatting at her back before realizing it was just a napkin. Then the reality set in that she had stood wearing only bikini bottoms, in front of her friend’s boyfriend, her b cup tits jiggling and swaying as she panicked. Her hands finally quickly went to her tits. She held them in hand bra fashion and began to laugh her ass off. My girlfriend already was. I was almost forcing laughter to hide how fucking horny I had become. All in all it was probably an 8 second show but it seemed to play out in slow motion and the view of her young puffy pink nipples is forever burned into my brain.

First let me say I proofread that story but didn’t catch that I said “Greek friend” instead of “girlfriend”. She was definitely not Greek.

Another funny story though is from that same time frame and with the same girlfriend and her same pool.

We had a group of friends over when her parents were away for a weekend. I stood at the edge of the pool with our friends (two guys and two girls) swimming. My girlfriend came behind me and depantsed me. My trunks got to my thighs and my cock was exposed. I’m not one to get embarrassed but our friends were hooting and hollering.

Needless to say I started exacting my revenge in my head. Perhaps she allowed the situation because she knew and wanted it, or maybe she figured I wouldn’t expose her but I swam to the edge of the pool where she stood at one point facing away. I hopped up and hooked my fingers into her bikini bottoms and as I fell back into the pool I pulled them down. I figured it may be difficult and maybe I’d only expose her bum for a brief second. But this was a bikini with strings on the hips and one side became completely untied and they fell to her ankles. She shrieked and yanked them up. The guys were all in the pool facing her nice round butt and as she kneeled to retrieve the bottoms her pussy popped out beneath. Her girlfriends were out of the pool with her so her pussy faced them as she frantically retied them. She called me an asshole and I said I didn’t realize they’d come off like that. But she was laughing so I knew I wasn’t in any big trouble. I didn’t tell her about her rear pussy exposure though. That might have changed things.

Here's my 'prank' story which I've posted before but it's worth repeating:

To bring you up to speed; I had this girlfriend, I'll call her Tina although that was not her name. Several years younger than me, 5ft 10, curvy, bloody gorgeous (think Kate Bush circa 1980) and sexy as a very sexy thing.
Anyway, with me still living at home and her sharing a flat with two other girls, privacy was a little hard to come by, so it became our custom, particularly in the summer, to head out of the city to a country pub, where we would sit and wait for the sun to go down. Then when we’d decided it was dark enough, we’d drive down the road to a deserted lane, where we would park, and enjoy a glass or two of wine before stripping off for some steamy rampant sex. (As the lady herself liked to call it!)
One night after we had done the deed, I had to answer a call of nature so got out of the car. While relieving myself I heard some shuffling, followed by a loud click and a giggle. And when I tried to get back in … I couldn’t. She’d locked the doors.
So there I was, twenty miles from home, stuck outside the car in a country lane where anyone could walk or drive past at any time, and totally starkers. (25 years before I became a naturist by the way!) I spent a very uncomfortable few minutes trying to persuade Tina to let me back in (during which time she was jumping up and down laughing, sounding the horn and flashing the lights) and making a supreme effort not to let her see how annoyed I was. Eventually, she relented and unlocked the door. (She couldn’t drive so at least I knew she wasn’t going to shoot off and leave me stranded.)
A week or so later we were back in the same situation and, as before, I got out. And as before, I heard the shuffle, click and giggle. This time I simply let myself back in using the spare key I’d had cut the day before, hidden in the door pocket, and palmed as I got out. What puzzled me, though, was that I never got my revenge by locking her out on some future occasion. Perhaps I just wasn’t as mean as she was!

That reminds me of years ago when I was driving a former girlfriend and her friend around. They got the idea to moon people. This was the early 2000s. They were both 18 or 19. Imagine a girl thinking this is anything but incredibly sexy to a random guy. Oh no a sexy 19 year old girl is showing me her naked ass. Anyway, I drove by the movie theater and there was a line of about thirty people. I stole this idea from the movie Dirty Work with Norm MacDonald. He does this to his friend. I drove by the line honking, my girlfriend and her friend screaming “whooo!” As they hung their bare asses out the passenger and rear passenger window. Then I stopped the car. “What are you doing? Drive!” My girlfriend shouted. I did not. After giving the line a view of their asses for nearly thirty seconds the girls started to go from giggling to mad at me so I finally sped off laughing all the while. A funny prank on them but also a sexy favor to all the fellas in that line. I bet some of them still think about it.

Maybe they were horny and were planning a threesome with you, but lost the mood after your prank. Don't annoy horny girls if you could maybe fuck them 😆

I don't know if this counts, but back when I used to cycle 30 miles every day, I used to get flashed by women A LOT. They would honk their car horn, I would look, and their passenger(s) would flash me. It happened almost every ride!

Then for the past 10-12 years, I haven't been flashed a single time. I don't know what was going on a decade ago, but it's a bummer that it stopped!

I assure you that was not the case lol.

To be honest I think it’s the current crop of teenagers and 20 something’s. They’re just kind of party poopers. All the people I know who are gen x and older millennials partied in their day and have stories of wild times. Younger kids are so tame. Maybe because their social lives have been mostly online.

The old ones sepnd their time telling about their past wild parties. The young ones are still busy 😁

Prank
 

My girlfriend was over one day and had to run out to her car to grab something. I locked the door behind her and when she came back I told her to get naked if she wanted back in. I expected her to say no and then I'd just let her in, but to my surprise she got naked right there on the front porch.

--- which reminds me of another story I've posted before, same girl:

She once told me about a male friend of hers who went round to visit his girlfriend, and when she opened the door to him, she had no top on.
I thought this story a bit tame but said, “I bet you wouldn’t do that.”
She said, “I bet I would.”
I said, “A pound says you wouldn’t.”
She said, “Right.”
I was on a roll now, because I’d just remembered something that I was pretty sure she had forgotten.
So I said, “Furthermore, I bet you two pounds you wouldn’t come to the door … with nothing on.”
A few days later I called round to have lunch with her and when the door opened she was hiding behind it. As soon as I was in and she shut it, I could see why. There she stood in all her glory, completely naked. And I do mean glory; don’t forget, she was five foot ten and quite curvy.
Then I said, “You remember that two pounds you owe me? Well, you don’t owe me it any more.” Tina said nothing, but I could see by her expression that she was decidedly not happy.
(She was quite happy to stay naked the rest of the lunch hour though, and for us to shag each other’s brains out before I returned to work.)

unexpected flash
 

I was at lunch today with a coworker. We were sitting by the windows where the cars waiting for their food from the drive thru were waiting. I just happened to take notice as the restaurant employee was running the order out to the car closest to me. The driver rolled down her window and just started to reach out to take the food when her female friend in the passenger seat reached over and yanked down the drivers shirt exposing one breast. The worker got the eyeful and so did I. The passenger was laughing up a storm as the driver had a brief shocked look then a slap at her friend with a I can't believe you just did that look. She covered up and took the food. The worker walked away with a smile on his face. As the girls drove away they were both laughing now.

I started this thread hoping for stories on the funny side of life that involve nudity, accidental or otherwise, not just pranks. So here’s a funny story.

My wife and I visited a botanical garden once about 5 years ago. We were both 30. It was a warm day and my wife wore a black summer dress with flowers on it. We have pictures of this day and every time I come across them I’m reminded of this story. It was quite boring but we ended up going inside a greenhouse for tropical plants. As soon as you entered you felt how they kept it very warm and humid inside. You could hear the whir of loud heaters and misters. My wife walked a bit ahead of me and stepped over a wide vent that ran across the walkway. Her dress was immediately blown straight up. Not just to her butt cheeks but to about her stomach. It caught her off guard and it took a second for her to react by trying to push it down before realizing the real solution was to step away from the vent. When it finally was back down, she glanced around to realize no fewer than 15 or so people had turned her way when she shrieked. Half of which were males of all ages that had been treated to a three second view of her ass in a black thong and her jiggling cheeks and thighs as she dealt with it. She was beet red but laughing.

A little later we circled the whole gardens and found ourselves back there. My wife pointed to a couple and said that lady’s skirt is gonna do the same thing. The woman was Asian. Probably mid 20s. I said maybe you should warn her but my wife uncharacteristically had a case of schadenfreude. So we followed them into the greenhouse and sure enough the woman had the same embarrassing moment. She had fuller bottom lacy red panties. About half her cheeks hung sexily beneath them. She grabbed her boyfriend’s hand and stormed out avoiding eye contact with everyone.

If lived in that city I would be an annual member and make my way to the gardens every sunny day and just camp out in the greenhouse.

I have two friends who are twin sisters. I used to go to the beach with them from time to time, sometimes wit other friends joining (but usually just the three of us). I don't particularly like the beach, but who would say no to going with two pretty young girls. One is thin, with long brown hair, and is quite shy. The other is a little on the heavier size, with large boobs, and is more outgoing.
One time, as we arrived, I changed into swimsuit under a towel, while they removed their sundresses to reveal modest bikinis that probably showed more than they realized. As I removed my boxers, and was looking for my trunks in my bag, the towel slipped and fell to the ground, leaving me naked and on full view to them, while both hands are in my bag. I was naked for maybe 20 seconds while both were laughing hysterically.
Once covered again, I was super turned on, and tried covering it by acting embarrassed. Then the shy sister did something that surprised me. She went behind her sister and did a tugging motion with her hands, and then yanked down her sisters green strapless top. Her large round boobs with pink puffy nipples jumped on jiggling while she shrieked and struggled to cover again.
Her revenge would only come weeks later, when we went to the beach again. The shy sister has just come from a job job interview and was dressed accordingly, while me and the outgoing sister were already there in our swimsuits. The shy sister undressed under a towel. She struggled with it and flashed her panties a couple times, so she asked her sister to hold the towel. While she was taking off her panties, and with one leg raised, her sister pushed her. She fell on me (I was crouched at that moment), naked. She had a full bush, bright brown colored. Her boobs were larger than expected, and had a bit of a teardrop shape with large brown nipples. From the impact I fell on my back myself, with her boobs touching my face. She let out a scream, got up and turned her back to me while taking back her towel.
After that we all laughed, and this was a start of a prank war between the three of us, and anytime we would go to the beach that summer someone would be exposed in some way.

Reminds me of one of my favorite memories. I’ll post it as my wife recounted on another site:

I had an amazing experience at a fun-house one time. Ed likes to have me dress up in revealing
outfits when we go out. During the evening I then often "accidently" expose myself to him in the
course of whatever we're doing. However neither of us had been in a fun-house since we were kids,
and we got more than we bargained for!

I was wearing a tiny little white cotton dress. It was tight on top, and although not see through at all,
it was obvious I wasn't wearing a bra. The bottom of the dress flared out much like a pleated skirt, but
without the pleats, if that makes any sense. The dress was so short that it only covered my butt
cheeks by an inch or so. The dress and my shoes were all I wore. (I've never been much for panties)
We were getting a lot of looks just walking around the fair grounds (more than a pretty girl in a sexy
outfit might normally get). Ed even saw one guy actually bend over to try to see up my dress after we
walked past him! (and I'd have to guess that he could see quite well!).

We went into the fun-house just for the trill of trying to navigate through whatever might be inside in
my skimpy outfit. I was nervous about just entering the ride, because you had to climb up 3 or 4
moving stairs on the outside. Once inside things were fairly uneventful. I climbed up a ladder, but
there was no one behind us. And Ed fondled me a little in a dark mirror maze.

As we emerged for the mirrors, we were probably a little disoriented, both from the fondling and from
entering a brightly lit area. We emerged onto a platform about 5 feet in the air. On the platform were
hand rails snaking back and forth like a ticket line, leading to a ladder to get down. Below was a
spinning tube you had to go through to exit the ride, with 3 or 4 carnies standing there watching the
platform. I was wondering how I was going to climb down the ladder with the carnies watching me.
Neither of us noticed the guy in the booth about 5 feet straight in front of us. You can probably guess
what happened next...

As I stepped out ahead of Ed onto the platform I put my hands on the rails and got about two steps
when I was hit by a blast of compressed air. As I let out a little yelp, my dress flew. The flared part
shot straight up, folding the dress in half. I was naked from my ankles to my rib cage!!!
The booth guy laid on the air for what must have been a good five seconds. I struggled to get my
dress down, but because my hands had been on the rails the dress had come up under my armpits
and with the force of the air blowing the dress around I never even came close to bringing it down.
Finally I made the not too brilliant move of jumping out of the air-stream... backwards.
You've never seen guys with such big smiles on their faces! We were laughing too, although I was
quite embarrassed. And I knew that I was still standing on the platform and would have to cross the
air vent again. Worse, I had to climb down a ladder, with 4 guys at the bottom who now knew I had
nothing under my little dress!

After I regained my composure a little, I moved quickly across the air vent, managing to only let the
back blow up a little. The carnies were very nice about the whole thing (none made any obnoxious
comments), but they also weren't shy about moving closer to the platform and ladder, and trying to
get another view. Somehow, by wearing what I was (and wasn't) and by reacting good naturedly, I'd
given up my normal right to have men not be so obvious about trying to see up my dress.
I got down the ladder as quickly as I could, although I can only image what kind of view they got from
below. At the time I thought of that as less embarrassing than standing there naked in front of them
with my dress flying, but as I thought about it afterwards, I realized that a couple of them had gotten
an even more intimate view as I backed down the ladder!

They tried to convince my that the safest way thought the tube was to crawl, but I wasn't buying it!
I've been seen many other times in various degrees of undress, accidently and "accidently". But
somehow those five seconds of forced exposure are the most naked I've ever felt

Great story, thanks for sharing! Did this series of events lead to more casual nudity, pranks with nudity, etc. moving forward since everyone had seen basically everything of each other?

Absolutely. We used to go to the beach in mid morning during the week, and off season (we all worked part time/were students at the time), so the beach was nearly empty, which made it easier for that.
Things like pantsings, wedgies, untying bikinis and sn*tching towels became a normal occurrence for us when we were at the beach (which we went to very often). One time the outgoing one pantsed me while I was talking to two girls from my high school I ran into on the beach. I later untied her bottom while in the water and she walked out, bottomless in front of a group of younger guys before noticing.

Another time, the shy one came in a new bikini, and said that the old one was too small (it had a tendency to show a lot of cheek and cling to her butt, showing more than she liked with the occasional buttcrack), and didn't cover enough. Naturally I gave her a wedgie and slapped her butt.

The whole prank thing usually remained just between the three of us, but extended beyond the beach. For example, one time the shy one pulled apart her sisters button-down dress while walking along an empty street, leaving her pink bra and panties exposed on the front.

As for casual nudity, not as much. We did once go to a secluded undeclared beach unplanned, and wanted to get in. While this place was secluded, skinny dipping was still out of the question. However, we all went in in our underwear. One sister was wearing white lace underwear (that became see through). My own boxers were tight and clinged to my dick, not leaving much to imagination.

Wait, did the one whose bikini you untied find her bottoms?

It was in my hand, so yes. She would never admit it, but I think that being exposed like that really turned her on.

My wife had send me a tasteful topless pic a few days ago using WhatsApp. She does that sometimes to suprise me.
When she came home yesterday, she told me she was sending me a message again using WhatsApp. That pic was still visible in the top half of the screen. A male colleague of her was standing right next to her and was watching at the picture. At home she was laughing it off, but I know secretly she likes being exposed like that. Keeping plausible deniability cause her colleague was never supposed to see that picture.

Too bad it was a "decent/tasteful" pic, cause she has send me lots that were more explicit and more clear to see. Pic is included. Judge for yourself.

Nice nipple!

Workplace Texting Prank
 

I was the "victim" of a cruel work prank back in the day. I was in a junior sales position. Most of the office was fairly young in age (23 - 35 mostly). And it was a very social group amongst everyone. But I was a new guy and more introverted than everyone else, so my working tenure there I was mostly an outsider to that workplace's social environment prior to this story.

When I was there I had sort of a "work wife". She was my sales lead and mostly managed my day-to-day as well as trained me in when I first started. She wasn't officially my boss that I reported to, but I interacted with her more so than any other person there. She was a bit older than me - I was probably 27 and she would have been maybe 32. She wasn't married, but had a serious boyfriend and she was WAY hotter than me. I had a mini-crush on her but since she was out of my league and taken, I never even considered it a possibility.

Anyways, one Saturday evening I got a text from her - totally out of the blue. We had each other in our phones for after hour work emergencies, but we never actually used texting to communicate until this day. It started with small talk and slowly got more and more flirty. I'm paraphrasing but her messages went like this:

Hey!! How'd it going? My boyfriend is hunting this weekend and I'm bored. Just thought I'd say hi and good job on the {random work account} this week. You did a great job!

And of course I took the bait. I texted back every time she texted me. And we had convo going from about 6 pm until 10 pm. I got a new message from her maybe every 10 minutes or so. And then towards the end of the night I got a yoga pants booty pic from her and she requested a dick pic from me. I couldn't believe this was happening. I was so turned on it was like a dream come true. And of course it wasn't real.

The next morning I got a phone call from a random number. Then they called right back when I didn't answer and left a voicemail the second time. I listen to the voicemail and it was my work wife crush basically saying, "Hey, call me right when you get this. This is my number. Call me at this number immediately." I was thinking that maybe our text flirt from the previous night got her in trouble.

Anyways, I call her back and she explained to me that it was a prank done to both of us by 4 others in the office (two guys and two girls). They had gotten together and orchestrated this elaborate prank in which they switched out the contacts of each of us in our phones to one of their phone numbers. So my work crush was getting texts from who she thought was me at first and of course I thought the texts I was receiving were actually from her. But in reality the texts I was receiving were from the 4 pranksters playing a joke on us. I felt like the biggest idiot ever.

She told me it wasn't my fault. I sent her screenshots of our entire fake convo. And she was beyond pissed whereas I was just more embarrassed. She told me she was going to HR first thing Monday morning and I begged her not to because I thought I was going to get in trouble considering my texts got awfully flirty towards the end of our fake convo. And the group of pranksters took the dick pic I sent and forwarded it to my work wife crush. So it was just such a complex situation that I felt like I was going to get in trouble over it.

Thankfully my work wife crush didn't go to HR. She just held a meeting with the 6 of us (myself, her and the 4 pranksters) and she ripped the four of them to shreds in this meeting and stopped being friends with them afterwards. Then she took another job somewhere else about 3 months later, which was a bit sad for me. But it was awkward between her and I after that entire incident anyways.

There was a silver lining for me, which was that everyone started liking me after that because I thwarted off the nuclear HR scenario - which would have been a disaster for everybody. And I hooked up with both of the female pranksters from that incident over the following year - not at the same time, but in separate hookups. And of course I had the yoga pants booty pic of my work crush - even though it was more of a cruel reminder than anything else.

Nickerboxer, sorry man that sounds rough. Couple questions though.

So did she send the yoga butt pic to them thinking it was to you or did they just end a pic of someone else to you saying it was her. If she sent it thinking it was to you, surely she had some interest in you.

Also did she ever comment on the dick pic?

Years ago at a restaurant I worked at a rumor started that I was fucking a new prep cook we hired just because we may have been a little flirty. It escalated and got to the point where a manager had to intervene. Eventually everyone realized it was a rumor only. However the situation caused me and the girl to become friendly and even though she wasn’t my type (mousy, skinny) we did end up having sex. Something that never would have happened otherwise.

No. I was wondering the same thing after everything calmed down. But when I asked one of the pranksters, she said they already had it. I don't know how they got that particular pic. I was definitely of my work crush though. They were decent enough friends with each other before that incident that I assumed they saw it and saved it at one point.

It was a side-angle yoga pants pic that showed the shape of her ass. But it wasn't some crazy sexy pic with any nudity. It was also kind of dark and fuzzy from early generation camera phones too.


No. From my understanding, when my work crush got the dick pic in a text think it was from me, that's when she started getting really upset and threatened to go to HR. Then the pranksters copped to the prank and it fell apart from there. Then she felt bad for me when she realized I was being pranked upon too.

There's no indication that she enjoyed any part of that prank. She was pretty pissed about it (not at me, but at the others) and left for a new job a few months later. And for me the embarrassment part was fine after the first week. The stress of thinking I might get in trouble was the worst part about it.

Back in 2004 I worked with the woman who was head of large contract sales. She was tall, blonder, slender, she had such an elegant was about her, she always wore heels. One day she had to drive about 60 miles to do a presentation to a client, she had A PowerPoint show, product to show, I offered to go with her to run the PowerPoint, and to set up the product, I wasn't busy, she was always busy.

WE get there in plenty of time, I set up the electronics and the displays and Charlotte nails the presentation, by the end of the day we have contracts signed. WE leave about 5:00 and Charlotte says she's buying us a drink and she'll even give me a cut of her commission, pretty generous since I didn't do much.

We stop at a nice hotel bar, have literally one drink and we head back. Well, we should have skipped the drink, it is raining torrents and for safety I pull off the highway under an overpass to escape the hail. I check the weather radar, we aren't going anywhere for a while until the front passes, it's dark out, the highway only had a few brave souls on it. Charlotte say she needs to find a bathroom, I go a couple of exits and find a Hampton Inn next to an Applebee's.

My the time we get in the Applebee's, we're both soaked, Charlottes silk blouse is see-through to her lacy bra, and she is cold from the AC. We have something to eat and coffee, weather looks better, so we go for it. I put my coat over Charlotte, I get go the car and pull up to the front door, but a gust of mind and cold rain soaks her again. The poor lady is shivering, even with the heat turned up. Charlotte says "to hell with modesty, I'm freezing, you're a married guy, you know why breasts look like." Off come all the wet stuff and Charlotte puts he ample boobs against the heater vents. I'm married and I've seen boobs, but not like those.

We agreed to never mention it, but at a boozy office party, she spilled the beans.

I saw a girl next to my apartment come out wearing towel, hang the towel there to dry and go back in i was so hard

Going back nearly 20 years to when I was in my first year of university, I lived in student accommodation on campus with five others - 1 other guy and 3 girls. It was a real mix of personalities but we all got on fairly well.

One of the girls (I’ll give her the name Jenny) was really sweet and easy to talk to, but she was quite different from the rest of us, in that she took her studies very seriously, didn’t drink much and always seemed kind of quiet/reserved. She was actually quite attractive in a geeky sort of way - slim with ginger hair and glasses. I learned from talking to her that she’d never had a boyfriend and I noticed she always tended to wear fairly plain, un-revealing outfits. She hung out with a small group of similar girls from her course and was a member of the charity / volunteering society.

Although we were quite different, we got on well and we had long chats whenever we were in the kitchen at the same time. I sometimes helped her with computer stuff and she always offered me cake when she did baking and even brought me soup and took my laundry one time when I was really sick.

One night, right at the end of the year, I was up late doing last minute prep for my final exam. I’d gone to the kitchen to make something to eat, when I heard a commotion in the corridor. Jenny had already done her last exam that day and had been to a party at her friend’s place to celebrate. Unusually, she’d been drinking and when I went to see what the noise was, I found her being guided to her room by one of her friends. She was way more drunk than I’d ever seen her before, but she seemed happy and her friend was taking care of her, so I went back to the kitchen.

Maybe 10 minutes later, I was alone in the kitchen taking my food out of the oven, when I heard the door open behind me. I turned around and couldn’t believe my eyes. Jenny had walked from her room down to the communal kitchen wearing only a cropped vest-top. She was completely naked from her belly button down to her feet.

When she saw me she smiled and started making small talk - despite the fact she was half naked and her bright orange bush was on full display. Her top was thin too, giving obvious pokies. Although she was obviously drunk, she spoke perfectly clearly and seemed genuinely oblivious to the fact she was naked from the waist down. I asked her if she was OK, she said she was, and then I remember her rummaging in the fridge, taking out something - maybe a pack of sliced cheese - and just standing there casually eating it while we talked.

We must have stayed in there a good 10 minutes longer - luckily for her it was late so no one else came in and saw her - after which I walked back down the corridor with her (a few steps behind, naturally) as we went to our respective rooms. The whole thing was totally bizarre - there was nothing suggestive about it and she just acted completely normal the whole time. I don’t think for one minute she was trying to initiate anything - she knew I had a girlfriend and that just wasn’t her.

She was the last one of my flatmates I’d ever have expected to show anything revealing - I’d never seen even a hint of cleavage all year - yet she was the one whose naked bottom half I got to see, front and back, for about 15 minutes straight. The main things I remember are her thick, bright orange bush, that her bum was disproportionately shapely for someone so slim and that her nipples looked quite puffy through the top.

Nothing about it was ever directly mentioned afterwards, but I still remember those 15 minutes vividly, nearly 20 years on.

Much less exciting than my other post, but very relevant to the thread title. During that same year of university, one of my female flatmates was quite jokey and liked to do stupid stuff / prank people, especially when she was drunk. For a while she was into pantsing people (or lifting skirts/dresses) for a laugh and I ended up seeing several of her friends in tiny thongs and lacy underwear.

It worked both ways though - she did it to me and the other guy flatmate a bunch of times. Maybe it was coincidence, but she always seemed to do it when we were in pyjama bottoms (going commando), so her and a couple of her friends ended up seeing me and the other guy full frontal several times. One of the times I was carrying a plate of food, so I couldn’t do anything to cover up straight away so they got a much longer eyeful.

I think it stopped after a guy friend of hers gave her a painful wedgie in return which was so hard it snapped her thong.

"she glanced around to realize no fewer than 15 or so people had turned her way when she shrieked. Half of which were males of all ages that had been treated to a three second view of her ass in a black thong and her jiggling cheeks and thighs as she dealt with it. She was beet red but laughing."

that is SO HOT!!!! I would love to see her cute facial cheeks blushing furiously after she realized she just inadvertently mooned everyone (what I'm sure were) her delicious bum cheeks (_!_) I'd have been sure to walk past her and give her a big knowing smile. Maybe even say something nice and teasing to her. There's also something very hot about 'males of all ages seeing her'.. especially am jealous and thinkin of the younger guys who I'm sure were THRILLED to see the bare bum of a pretty ENF MILF... no doubt they all filed that memory into their long-term spank bank.

I'm a huge fan of office sex fantasies... and have been around enough very attractive office women in their skirts and high heels to have developed quite a fetish for this. Unfortunately got to admit I never had a great serependitious encounter, but certainly had plenty of fun, teasing, flirty encounters. Anyway I bring that up cause I find this story of yours SO FRIGGIN' HOT!!! For starters, love the way you described Charlotte (tall, blonde, slender, elegant, always wears heels.. and I'm sure nice dresses and teasing skirts!!... and then of course, the see-thru silk blouse and lacy bra). What a great image! I've found that some women who dress and appear that way might also look 'nice' but not necessarily be a total knock-out, yet over time seeing them dressed so nicely in this 'formal office setting' and interacting with them in a professional manner leads to one day you looking at her and thinking.. woah.. she is actually quite a bit hotter than I thought! And maybe its a simple accidental peek up her skirt or seeing her bending down over your desk in just the right way or some small image like that that sparks that fire. Or, even better as in your case!!!

So back to your story.. she's all excited about landing this huge deal, decides to let her hair down and grab a drink with you.. and then it all starts going (wonderfully!) topsy-turvy. Her blouse gets soaked.. becomes see-thru... its as if she's modeling her sexy lacy bra just for you.. as if she's not even wearing a blouse (!)... her pretty hair is all wet, all disheveled.. and she suddenly and WONDERFULLY throws modesty out the window and decides its okay to fully show (not just flash.. but FULLY SHOW) you her ample bare breasts. Sitting in your car.. in her sexy heels... her sexy skirt (?).. and 100% topless!!! I can not imagine how HOT that was!!! I would love to hear more if you can share about what her demeanor was like? shy at all? care-free? matter-of-fact? laughing with that 'I can't believe I'm doing this' expression? I hope you found some way to politely compliment her on how wonderful her boobs were and how fantastically exciting this was for you without coming across as a creep. No doubt you knocked out a few thinking about Charolette's boobs.. or thought of them next time you were having sex. No? btw, how old was she? you? .. I'm sure you didn't, but I'd like to think you offered to massage them for her to get the blood flowing and warm her up faster :)

the stories on here are just absolutely great.... love this one! certainly have had a few female roommates, female friends or girlfriends of my roommates of mine spend the night and would have LOVED to have had such an encounter with!!! LOL gotta say (hopefully without being creepy) I would not have been able to resist at least giving her cute little bare bum cheeks (_!_) a few little pats as you dropped her off in her room and told her with a smile "good night.. hopefully you wont rememebr much about this in the morning"

Shower peep on colleague
 

I forgot about this one because of the woman's attitude when she left and only remembered through this thread's title. This happened 11 years ago.

We were sent on a training in Singapore. The woman I'm with was a replacement. Kat was 25 years old that time (5'5, pretty, slim, small breast but has a very nice butt).

Since she was a replacement from my buddy, we had to share a room in a hotel (paid prior). The room has a weird setup that you can see from the side of the bed/s the top of the head of the person showering (atleast 5'5"). The shower and tub positon is parallel to the beds. For a week, if she showers, I go outside for a moment and go back after some time.

On the 8th day, I had to support a colleague that was having trouble on site and have to stay. Kat knew this but proceeded to shower and didn't say anything. When I saw her using shampoo on her hair, I quickly put a chair to check her. The problem was I can only see her back (not tall enough). Then it crossed my mind to jump. I jumped 3 times from the chair and saw Kat's heart shaped butt.

I brought the chair back to the desk and pretended to do stuff. Kat got out of the shower. I looked back as she passed by while reimagining her butt. She faced me and said she felt a little vibration while in the shower. I replied that it was maybe the room on top of us.

I "pranked" my wife her first time at a nudist resort. This could have really backfired...but I just couldn't resist.

Her goal was to not be seen openly naked. So she wore her towel tightly wrapped; and in order to get in and out of the hot-tub without being seen nude, she had me hold her towel in front of her every time.
The third time I decided to rip the band-aid. I had exited the hot-tub, and she held her arms up motioning for her towel laying on a bench. And I grabbed her arms instead and started lifting her (she's not very heavy). Surprised, she started flailing her legs, trying to balance herself, and rested her feet on the hot-tub ledge, in a semi-squat. Her ass and pussy completely exposed to the people still in the hot-tub. I then pulled her completely out and walked over to her towel, leaving her standing completely naked and slightly embarrassed. I then handed her the towel and she gave me a "WTF?" look while I returned an "Oops" look.

She wrapped herself back in her towel, and I thought: "Oh...maybe I did screw up." But it had in fact ripped the band-aid. As we walked back into the pool area, she suddenly stopped, looked around; and tossed her towel on a lounge chair. She'd been seen naked; and now she no longer saw a point in still covering up. So this "prank" actually helped her get over her anxiety at being seen naked. Lucky me!

just did something today
 

I just did something that gave me a massive thrill.
I streaked butt naked (not even footwear) to the floor below my floor and ding-dong-ditched a family

Flea Market
 

Headed to a flea market as soon as we get a good dry weekend to set up and sell a truck load of junk again,one thing we tried to sell last year but no takers was a picture viewer that takes only SD cards or flashdrive to show pics,5 bucks brand new but this year it will be different,three dollars and they get a SD card with some pics,if no takers I plan on walking around with it and you see a lot of single guys there selling and I plan on telling them 3 bucks and you get a SD card with about 50 real pics of my wife,and if they ask or I tell them,lots of bikini thong pics and I think a few topless ones,which about half will be topless and nudes,lastyear we sold some homemade paper weights with some very risque pics on and some knife sheaths with nude engravings on,one couple said these pics look like her and the guy said if it's not her it looks just like her.