Missed Opportunity
 

Have you every missed a good chance to excite yourself from a nudity option.Thinking back I have many times.
Lets hear her missed opportunity here,I'll start..
Years back my first wife would nude sunbath out by the pool in the back yard,once Eric our teen neighbor down the road and mows our lawn walked in the pool area and did catch her sun bathing ,she jumped and covered up,we all laughed about it,how many times when I got home from work and my ex was nude sunbathing,I should have called up Eric and said come to the front door and just look out the back window,wish I did now,but I never thought about it then.At one time Eric came to my work to get paid for mowing so I took 3 topless photos of my wife then and hung them in my locker and when I opened it he got a god eye full of her tits.

I'm sure if I searched my memory banks from high school through today I could come up with a dozen or more instances like this. One that comes to mind right away is this "party" my little high school clique of band geeks threw at one house where the parents were away one night the summer after senior year but before college. I put "party" in quotes because our parties were all decidedly lame non-racous affairs with relatively little alcohol, no real dancing or sexiness or anything, video games and board games were often played. There was usually about 15-20 people, fairly evenly divided by gender. This one party was lame even by our standards, we watched the first Spider-Man movie on DVD, some people were quietly chatting in little groups, video games were turned on, some people were even passing out on the couches and stuff. My friend and I decided to bounce around 11, go grab late-night burgers or something.

Then I found out the next day that the party had somehow picked back up around midnight, some more alcohol was consumed and a game of strip foosball had broken out at the foosball table in the den, and this one cute band girl I had known pretty well since elementary school - the sort of girl so sweet and geeky and innocent-seeming you couldn't picture her being sexual in any way ever, and who all the way through finishing high school dressed so conservatively nuns would approve - had taken her top and bra off for about five minutes to the cheers and applause of everyone there. (This was before the age of the camera phone.) Apparently she was blushing and laughing like crazy and did the covering-her-nipples-with-one-arm thing for a couple minutes before just giving up and letting it all hang out for a couple more minutes. Apparently she even briefly stood around holding her beer and chatting with some guys wearing nothing but her jeans before getting dressed again. No one else girls or guys stripped beyond underwear.

Needless to say I was very unhappy to hear this and to know that several of my friends had now seen this girl's tits that I assumed would probably never be seen by anyone but her future husband. I attended more band clique parties that summer, most of them with her there, but nothing similar ever happened again. She was right back to dressing like she was on her way to church. This was like 13 years ago and the girl in question is now a standard suburban mom, and I kick myself to this day for leaving that party and not witnessing her night of life on the wild side!

Who Else Was Watching My Sisters-In-Law?
 

No one specific moment here, but in general I wish I could go back and do things a little different.

I used to perv my sisters-in-law a lot whenever my wife's family got together – whether it was looking for the times they left doors ajar when changing, wearing sleepwear or underwear around the house, bathing suits on vacation, upskirts, downblouses, tent windows zipped down when camping, sitting close enough to make physical contact on crowded couches, extra long hugs or kisses, etc.

Later, I wished I’d paid more attention to who ELSE was perving them, either other brothers-in-law, or later, nephews when they became of age. Only about three times can I recall catching any of the other brothers-in-law checking one of them out just a little. And the teen nephews had cute teen cousins to keep them occupied. But mostly I was on a constant guard to make sure that nobody was noticing ME perving the SILs.

Rather than always lurking around looking for a view myself, I wished I had just lurked silently in the back or out of sight and seen if the SILs were getting watched by other men, or if the SILs were checking out or flirting with their BILs or nephews. There were just a few occasions where the SILs’ actions could have been interpreted to be flirting with or touching or watching their late teen and early twenties nephews, but most could be explained away rather easily.

Surely I can't be the only sicko in this family that ogled his SILs, or when younger, ogled my own aunts.

Oh yeah...

That was back when my ex and I were active social nudists.

I had a co-worker I befriended and became close to - I'll call her An. An was pretty darn hot. My wife knew her and she didn't seem to care about our friendship. Even though there definitely was some sexual tension between An and I, we were both respectful of each other's marital status.

I told An about my nudist lifestyle. And she became interested in my nudist stories and they became frequent topics of conversation. One day she came to me asking me about home-nudity. My stories had inspired her; she wanted to ty it out but was concerned about her son. After I gave her some pointers she came back to me later with a big smile on her face. She had decided to make "the jump"; after taking a shower one morning she made her mind to just stay naked, and it had been a success! She'd loved walking around the house naked! After that our talks of nudity became mutual; I'd tell her about my nude weekend, and she'd tell me about entire evenings spent nude relaxing, doing chores or playing nude with her son. It was quite a thing.

There were hints or side comments about taking it "further." They never really turned into serious conversations though. I even asked my wife about her joining us; she was against being nude with people she knew, but since she didn't know An all that well, she wasn't closed off to the idea.
Maybe because I thought being nude around her would be weird (I had a strong attraction for her) or because I thought it would affect our work relationship, or because I'm just chicken; I never outright asked her if she'd like to be nude with us.

Shortly afterward An got laid-off; and I subsequently took another job. We kept in touch and we decided to have lunch together. We met and it didn't take long for her to ask if I was still nudist. I was, and I decided to just ask her the "$1,000 question": "would she have been interested in trying out social nudity with us?" And her response stunned me.
After being nude at home so much, she had considered taking it "further." She'd looked into nudist resorts but was daunted by the idea of going by herself. So "yes" she would have gone with us to "check it out."
After this revelation I decided to ask her the "$2,000 question": "but would she have gotten naked?" Her response stunned me even more. She said that it certainly would have been a little weird to see me naked, but my wife being there and nude would have helped. And whereas going naked on her first try would have been improbable, she most certainly would have gone bottomless.
My reaction was "Whaaaaaaaat!!!" Bottomless!!??" Besides the "odd" choice of going bottomless, there was the fact that she had obviously given it some thought - to come to the conclusion that she'd go bottomless! And the fact that she was showing that she would have had no problem being bare ass'd and bare puss'd (she had already told me to kept it smooth shaven) around me.

At that point it was too late. An had divorced and was now dating a possessive guy who didn't want her naked around anyone else but him. The opportunity had passed. But forever etched in my mind is the image that would now never happen -of us getting to a nudist resort or get-together, me getting naked while she took off her short/skirt and panties to reveal her beautiful ass and shaved puss. I'm sure I could have gotten naked just by getting her into the hottub or pool; but I guess we'll never know.

What a missed opportunity!!!!

nakked
 

I missed another time,wife was out in the pool,I knew her mother was stopping by that day before she went away for a week,I knew what time she would be there so as I was in the house I seen her slow down at put on her blinker light,I took off my swim suit and had the side door wide open,I was in the diningroom totally nude waiting for her to walk in on me,as I pretended to be talking with great anticipation and half a woody,she never came in,just backed out and drove away....b*tch.......LOL,she caught me nude a year or 2 later in the pool,,that was great.

Sure, if you go back to HS & College there are a number of "missed" opportunities. More like situations interrupted - you just unhook the front clasp of a bra when someone walks in, a sweet tight redhead with puffy nipples chickens out just after she lifts her bra on a dare, a girl has second thoughts about cheating on her boyfriend after a few licks, the list can go on.

But more recently and this is something I missed: I had been helping my SIL move some furniture around her house and when we were done we were supposed to meet up with some people. I left and she said she would shower and meet us. Her driveway is long and secluded, so I drove about halfway down and walked back to see what I could see. There she was in her room, starting to undress. I didn't see anything, yet and knew that around the house I could see into her bathroom. So I gambled and snuck around to try my luck. Saw the light come on, but the angles must have been wrong, but I waited anyway. Still nothing. Finally decided to move back around to her bedroom just in time to see her clasping her bra. Missed the whole "show" by picking the wrong window.

Still had the rush of possibility and the resulting massive hard-on, but oh if I would have picked right.

Cousin's Wife
 

This may not precisely fit, since it was something beyond my control and not something I set up, but it was the very first thing that came to mind when contemplating failed voyeuristic events. I’m not a world-class voyeur that sneaks around the neighborhood peering into windows or anything, but I do keep my eyes open for opportunities for seeing nudity, and perhaps I’ve crossed a line once or twice. And as any experienced voyeur probably knows, there are more failures than successes.

I previously posted a story about how I saw my cousin nude while we were staying at a lakeside cabin on a family vacation. She was staying in a bedroom that had a window overlooking the enclosed porch, and my bed was on the porch. The window was only covered with a sheer curtain, so when the light was on in the bedroom I could see my cousin changing clothes. The same week that I saw my cousin naked, I also saw a family friend in that room, an attractive woman with dark hair and B cup breasts, in her bra. She was staying in another cabin, but happened to be changing her outfit in that room.

Which leads up to my major disappointment. A year or two later, we were staying in the exact same lakeside cabin. This time the people staying in this cabin were my brother and me, my grandma and grandpa, and my older male cousin and his wife. His wife was in her early twenties, had long dark straight hair, pretty. Her figure was slim, but with curves – nice hips and C cup tits that looked real large on her slender frame. I didn’t see her often, but to me in my late teens then, she was an “older, adult woman”, and one of my top regular fantasy objects.

When we arrived at the two-bedroom cabin, my grandma announced the sleeping arrangements. My brother and I were to sleep on the enclosed porch. My grandparents were to stay in the front bedroom, and my cousin and his wife were to stay in the back bedroom, the one with the window and sheer curtain overlooking the room I would be sleeping in.

My heart immediately raced. There was almost no way that she could change in that room for a whole week and I wouldn’t catch her naked at least once, especially since I would be on a constant vigil for the opportunity. At that point I could have died happy if I’d seen my cousin’s wife’s tits, fine ass, and dark bush. I had dreamed about them so many times.

Then, as we all went about unpacking our gear in our assigned rooms and I was on the porch, I heard my cousin’s wife whispering to my cousin in sort of an angry tone. After a minute, my cousin went and whispered to my grandmother. I instantly guessed that my cousin’s wife realized that she would be staying in a bedroom that two “younger” teen boys could see into. And then I heard my grandma announce that my grandma and grandpa would stay in the bedroom with the window, and my cousin and my wife would take the front room. A major disappointment for me. I realized that it was likely a once-in-a-lifetime opportunity, and I never did see my cousin’s wife’s tits.

There is a thread in this story forum entitled 'family exposures' which would be just the place to tell this stòry 'Outbog'

Chojun

I've got another missed opportunity...

This was back in my post-college retail days. I was good friends with one of the store employees, who happened to be a backyard nudist. At that point I was a burgeoning nudist myself so we'd joke around about being naked. But for whatever reason we never got to be naked together. I had been to her house but only for a quick beer; being nude in her backyard never came up - I guess maybe we both thought that me being her boss might make it too weird. Or maybe it was just me being chicken.

One day she tells me that she's throwing a pool party - and that she's thinking about making it clothing-optional. I tell her to "go for it"; and then she asks me to come over and, since I like being naked, to come over and "encourage everyone to get naked." I knew a couple of other people from work were going to be there, as well as her "very hot" teenage daughter; and I wasn't going to be the "guy" who just jumps up, gets naked in front of everyone and just yells out: "Everybody get naked NOW!" What if no one else got naked and I stood there, like a jackass, butt naked in front of co-workers and her hot teenage daughter?
The day of, I ended up working a second shift. My friend finds out and asks me if I can trade shifts. I lie and tell her no one will trade with me.

Later that night she calls me at work. The party is kicking off. I say "sorry I've got to work." A couple of hours later she calls me again. "We're in the pool...naked!!" I start sweating. "Who is naked?" She tells me she is, along with a co-worker, a neighbor, a couple of friends...and her hot teenage daughter. My friend was the one who called out "let's get naked", her daughter then tossed her bathing suit, followed by these other people. I could hear them in the background having a blast.
I was doomed. I was running the store by myself and had no way to close early. I damn near kicked the last customer out of the store and hauled ass. I then grabbed the phone to call my friend; of course the party was winding down; people were leaving and the last few had put their clothes back on. It was fewked.

I asked her later if she was planning another skinny-dipping party. Nope. They had made such a ruckus that the neighbors had complained. She had a tall fence but one of the neighbors had managed to get an eyeful of her daughter. So it was a one-time deal.

Totally fewked up opportunity.

Barbarella has an exhibitionist streak that we are still exploring and each year it grows. A few years back we had been out for dinner and drinks. I hadn't been drinking as I was driving, but B had consumed quite a few and was feeling very frisky. And it turned out that on the way home she was in one of those "we can do anything you want" moods. They happen on those rare occasions when the stars align for her. It's at these times that we are able to go boldly into new territories and push ourselves to the next level... BUT it was that time of the month, so instead of being able to do anything about it, she just started to tell me some of the things she would have done, like...

- get totally naked and masturbate for the ride home (we've already done that before though)

-let truck driver's look at her if we pass any (we've kind of done that before, but this time it was her idea)

-Go into a convenience store and let the clerk see down her top (she never wears bras - and we could have actually done that one, but she said no because if we were going to start, she wanted it to continue, and by continue we are talking a massive session and that just wasn't possible)

- She wanted to go to the red light district and look at all the prostitutes (all dressed up in cosplay) and masturbate as we slowly drove through the area.

- she wanted her legs spread and tied up in the back seat and masturbate (we had talked about that one before and want to make it happen at some point)

and finally stopping at a love hotel on the way home with SM gear in it. (we have done this before as well, but that was at the beginning of her journey into exhibitionism and SM play)

She really squirmed in her seat the whole way home.

A while back
 

Back at my old house and my first wife,she was out in the pool like alway,she was 34DD 22 38,big tits and a big ass,all silicone too,I was upstairs with the old VHS video camera getting some video of her and our neighbor John who was near 80 was walking around his yard,the gate was wide open and she was nude on the float,watching this short video of her i always said to myself I should have ne out to talk to john and said I'm going in for a dip and john was kind of slow,and then I should have dropped my towel and ran around the stockade fence quickly and instead of going into the pool gone into the house and watched john go into the pool and get an eyefull of tits and a bush...............

Ordering a pizza while on lockdown reminded me of a missed opportunity from about 10 years ago ...

I had just started dating my eventual wife, maybe a month or so in. She came over on a Saturday morning, the clothes came off, and she basically spent the weekend buck naked in my apartment. Well at one point we decided to order a pizza. She's sitting on the couch, which is against the wall, and to the left of the couch is the front door to the apartment.

The delivery guy knocks, I quickly pull on some shorts and answer it, hand him the money, take the pizza, and he leaves. Took all of about 10 seconds. Only as he's walking away and I look over at my gf do I see she's beet red, all curled up, unsuccessfully trying to cover up her good bits. And that's when I realize what a glorious ENF opportunity I missed.

All I had to do was ask the guy to hold the door for a minute while I got the money. Or asked him to put the pizza on the table just inside the door. Or something. Anything. And he'd have gotten to see everything she had. All I had to do was find an excuse for him to poke his head in. Damn.

I mentioned the incident to my wife the other night, and I was surprised to find that she totally remembered (rather vividly) being absolutely terrified that I was going to expose her. Yet at the same time, she seemed a little turned on by what could have been.

My wife teases me like that...I will have an idea, she seems mortified that I might do it, so out of respect for her I don't end up doing something. Then months or years later I will mention it, and she always says, "Well, why didn't do you do it anyway? I probably would have loved it!" Grrr...

I've mentioned to her that I like the idea of her showing off, yet she's too self conscious to act on it. But secretly I think she's got a little bit of an exhibitionist streak. When she was maybe 19 or 20 she once flashed her boobs but her bf at the time was not nice about it afterward. What an insecure bonehead, he probably derailed her from developing into a fun loving exhibitionist.

A few weeks after the above pizza incident, she showed up at my door in nothing but heels, stockings, and a long coat. So perhaps she was a little intrigued, although she said she was scared about being pulled over during the entire 25 minute drive.

I've also told her that she'd make a great figure model for an art class. She surprisingly didn't dismiss it out of hand, but said she wanted to get back in shape, and lose about 20 lbs. We shall see.

But I still fantasize about that pizza delivery and what could have been.

reminds me of this cartoon

Wife in highschool.
 

My wife told me once when we first got together that she flashed the football team after they won the championship.

Now she says that didn't happen. But it's still a cool vision to think about.

Back in college after a night out, we went to a local pizza place many of the students stopped at after a night of drinking. Our large mixed gender group crammed into a booth, with me on the outside struggling to keep myself from falling off the edge while sitting next to a cute dark haired girl I was pretty good friends with. Across the aisle and a couple booths away was another group that I noticed when a girl on the bench facing me got up from the booth in a very unladylike fashion, stretching one leg out then the other, which gave me a very good view of her black panties under a denim mini skirt. She walked past our table to the trash can to throw some items away, and while passing our table my dark haired friend said out loud to nobody in particular "Oh, I have that same skirt!" referring to the girl who I just upskirted. I watched as she walked back to her table and got back into the booth in the same unladylike manner and continued to sit with her legs further apart than they should be for the length of skirt she had on.

That's where the truth ends because of the size of the group we were with, but in my head I'd love to think that I pointed out this girl to my dark haired friend with a comment like "Do you sit like that when you wear the skirt too?" In my mind it gets even better when she replies "No, I can't do that because I usually don't wear panties!":)

A looong time ago, I want to say 2012, my now-wife and then girlfriend once tentatively brought up when we were cuddling in bed after having sex whether or not I would ever want to do an MFM threesome situation or watch her fuck another guy. Being more young and jealous and still having my hangups, I grimaced and politely but firmly turned the notion down, and she never brought it up again.

Cut to a cool dozen years later and now I'm the one who finds the notion of kissing her while she gets pounded doggystyle by another guy indescribably hot, and I fantasize it about it a lot! The other week while we were making out before having sex - in a full reversal of twelve years ago - I tentatively asked whether she would ever fuck another guy for me while I watched, and she was the one who said it was fine as a dirty talk fantasy thing but politely but firmly said that she had zero interest in ever actually doing it and my dick is the only one she intends to have in her for the rest of her life.

So opportunity gone it seems! What was hot to her in her early 20s as someone's girlfriend no longer appeals to her in her mid 30s as someone's wife. In retrospect I do wonder whether her offer back then was more specific that it seemed - i.e. whether she had a specific coworker she had a crush on in mind or something and if I'd agreed the thing would have been suspiciously arranged in a matter of a few days - but man would I love having the memory in the spank bank of getting a live action hardcore porn of my wife play out in real time before my eyes. I wish I'd gone YOLO when the chance had been offered!

But ah well, seems that's a fantasy for another life. C'est la vie.

Or she aldedy had another guy when she asked you then, and now she doesn't. Girls who have more than one often fantasize of having them all at once.

Possible but seems highly unlikely to me - she never cared about leaving me alone with her unlocked phone if she went to shower or something, was always happy if I dropped by unannounced or unexpected, no odd or secretive calls or texts or unexplained absences, would check her social media messages on her laptop in bed right next to me, no evidence of anyone else ever at her place. If she was going behind my back at any point, well, kudos for getting away with it because she was hiding it MASTERFULLY.