Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Stories about girls getting pantsed, stripped and humiliated by anyone or anything.
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Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

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Charlie's Unforgettable Summer Swim - Titless Topless Tomboy
Contest prompt - Flat Girl (courtesy of Executions)

Not exactly the prompt but close enough I hope!
My initial deception of the boys wasn't on purpose. I had stayed at my Grandma's house by the coast most summers since I was a little girl. Growing up I was never like the typical girls my own age. I was a tomboy who loved to roughhouse and play boyish games and often avoided other girls. The friends I had made over the years local to my Gran’s house had all been boys. I had introduced myself as Charlie as I hated being called Charlotte to them. Quickly I realised my shortish hair, sports attire and general demeanor had convinced them I was too a boy. I was too embarrassed to correct them and year after year my deception only got worse. Initially It hadn't mattered much but as time passed and we grew older the fear of being caught out grew as our differences developed.

Two years had passed since my last visit and I was now a teenager. Despite this I was both short and vastly undeveloped in the boobs department. I could have easily passed for a much younger girl or as it turned out for a younger boy! My initial fears of discovery had been swept away quickly as Cody and the other boys greeted me out of the car having heard of my arrival in advance!

At first I was teased for still being a small fry as these boys had all matured and suddenly my heart was sent fluttering thinking back to our once innocent games and interactions. Any thoughts of confession drifted away as we fell back into our normal games and adventures. I just always made sure to dress as boyish as I could around them. The other boys just took my voice and stature of not going through puberty and something to tease me about.

Our wrestling games suddenly turned into something much more exciting for me. Dressed in only our shorts, vests or for the actual boys often topless, the close physical contact was unreal. I had never really noticed boys before but now my tanned, fit, playmates were all I could think of as we tumbled together and they easily forced me into submissive positions. I found myself flushed often as the powerful boys pinned me down laughing.

It turns out the boys had also found girls too. Many of our games turned into spying sessions trying to catch girls undressing or at the beach. Little did they know they had a girl right in their midst. We would hide in some bushes overlooking the beach trying to spy with one pair of binoculars as young teens or women got changed under towels not always so careful about their exposure. We also one evening crept onto a well facing the back of a local girls’ house as we tried to watch her get changed through a window. She caught us and we all ran off laughing as she cursed a few of the boys she knew from school loudly.

The boys shared many stories, most I’m sure were made up of seeing girls in their underwear, or naked, kissing girls or even copping a feel of their boobs. I could only blush as a contribution to these stories, much to the amusement of the boys as they teased me for still being a little shy kid.

I learned alot about male anatomy and the habits of teenage boys as they proudly declared about porn they had watched and played with themselves over or girls that they had seen and used for memory stimulation later. A few of the boys I had seen with tenting erections under their shorts during our spying missing or when they talked about girls as their hormones raged. For myself I often found myself flushed and getting very excited in the kitty area!

Everything was going well until a week in, a surprise swimming session caught me unaware! We were hanging around by a swimming pond and suddenly the boys all started stripping off. Only one was wearing trunks, the others wore boxers or briefs as I watched them in open mouthed shock. I was in heaven as I stared at them undressing to their private undies! To my young self the boys were like tanned gods, not the skinny runts they actually were. The boys soon noticed that I wasn’t joining them however and started shouting for me to get undressed too.

I tried to protest but this only brought the attention of every boy in our group as they teased me for my inaction. They laughed at me for being shy or too scared to strip in public. Worse still, they started heading over, probably to strip me themselves. Reluctantly I started to strip, my heart pounding as I quickly revealed my vest and then my white panties to the boys. I was so sexually charged and shaking now as I showed off my own private garments for the first time to them. They were plain white, big and luckily passed just enough for boy undies that the boys didn't really notice the subtle differences. They did tease me for being shy and wearing little boy undies however as I blushed bright red.

I had not worn a bra all week, not even the training ones I wore to school, for fear of being caught out. I did however have a vest that just about covered my budding little boobs. All six other boys were topless now and I knew it would look odd to be in a vest, dare I really strip off to join them I considered my emotions conflicted. I worried the boys would get suspicious so while their attention was mostly away from me I quickly stripped off this too. I could barely walk now as I tiptoed towards the waiting water and the boys splashing around nearly naked. Everything felt so surreal as I was practically naked in public, only my knickers covering me.

I wanted to cover up my little nipples and panties so badly but dare not attract attention to myself. I ran for the water quickly, my heart pounding, butterflies in my chest. A couple of the boys watched me closely, their own confusion almost reaching a conclusion as I bombed into the water glad for any covering I could get. Truth be told I may have been titless but in that moment of near nudity, wearing only my knickers I looked very feminine. If the boys had more experience of girls they would have surely noticed my elegant hips, the way my knickers were shaped without a bulge, the subtle difference in my ‘just about to bud’ breasts and the way I screamed as I jumped into the freezing water.

My previous deceptions however was the only thing that kept my identity hidden as I found myself splashing and playing along with the boys. How could their playmate they had known for half a decade not be a boy? My hormones were raging now as I jostled and played near naked with them, my worries slipping away. The sun and cold water kissed my exposed nipples and my knickers soaked through clinging to my privates, my womanly secrets only hidden by the waist high water.

The feeling of naughty freedom was unreal, I would never usually let a boy my age see my underwear, nevermind being totally topless only in them. I was ashamed of my undeveloped body, but somehow the boys thinking I was one of them let me live out every fantasy that washed through me on a sleepless night of exploration. It didn’t matter that I was flat, the boys only saw me as one of the gang.

My nipples were super sensitive, every slight touch or splash of cold water sending chills through my body. The water was murky enough from our activity that I could even give myself a few sly touches below, feeling the electricity of excitement explode through me. I ached to find myself a private place and looked forward to my bed for non-tiredness reasons that night. The boys weren't the only ones who knew how to enjoy themselves after a day of enjoying the opposite sex.

I watched one boy get out of the water in only his white briefs. My heart skipped a beat as I could see his willy and balls clearly through the soaked fabric. This would have been a brand new level of excitement for me, if only it didn't bring a new revelation. I suddenly knew I would have a similar and even worse problem when It was time to exit myself. This new fear damped some of my hormonal excitement, why hadn't I thought of this before. I was currently living a dream, but one that could easily turn into a nightmare. I was brought back to reality of my playmates finding the truth. How would I live it down if they knew they had seen me, a girl, in just a pair of knickers. However it turned out this was the least of my problems as our games raged on and a new group joined us by the swimming hole.

We didn't notice them at first but suddenly a cry of feminine delight erupted as a group of girls burst from the undergrowth laughing at us making their way to our discarded clothes. They were all around our age, I vaguely remembered them from years before but now they had filled out their swimsuits and blossomed into lovely young women unlike myself. Their goal was obvious catch some skinny dipping boys.

The boys made a run for it, covering their underwear as they ran for their own clothes or just ran the opposite direction away from the laughing girls so as not to be caught. I was too slow however. I had just made it a few steps on land, my hands clasped over my front as I was tripped by a skipping rope. Time seemed to stop for me as I fell to the floor, my whole world falling apart in a few seconds.

“Got one!” Laughed the girl as I found myself landing hard and pinned to the muddy bank with the wind knocked out of me. “Eh who is that anyway?” another girl asked, walking over to examine their prize. It was the girl we had been spying on the night before. I was hyperventilating now as I was stuck!

“That skinny city boy they’ve been hanging around with! Oh my god look at these little undies!” I tried to break free but there were too many girls now. They pulled my hands away from my bottom letting them all get a good look through the soaked fabric. My naked bottom, practically on show for them as they all giggled as only teen girls can do.

“Please let me go!” I begged in total panic now finding my breath. The girls only giggled at my plight holding me down tight as I tried to break free from them.

All five girls had me now and their words dug me deeper into pit that was my mortification "oooh look at the little baby bottom!" "Skinny little runt aint he?" “Turn him over!” “Yea lets see his willy bet it’s tiny!”

"No please don't! no!" I cried as I tried to fight but honestly against five bigger girls I had no chance. I was turned over and pinned to the floor again, totally exposed as they planned but with no willy to show for it. Their laughing and giggling was silenced as I gasped in shocked humiliation. My thin, white, soaked through knickers showed every inch of my kitty to the group. The girls had been hoping to catch a naked boy but had caught a girl instead. This was my worst nightmare, well at least the nightmare I could think of right then, it was about to get a lot worse for me.

“He’s a girl!” Screamed one group in total shock. The silent spell broke and the others all started laughing uncontrollably as I tried to break free and cover up my exposed self from them. The girls however had other plans, pinning my arms firmly to the side. “Do the boys know?” one asked me eventually between giggles.

I was crying now, the shame too much as the other teenage girls saw every inch of my undeveloped nudity “no, please don’t tell them!” I begged as the girls examined me closer. The girls had no mercy however, they were riled up and ready to totally humiliate me. “Look at these flat little boobies” one girl laughed, tweaking my nipples making me cry out in both shame and pain. "What a little weirdo letting the boys see you in just your baby knickers" "Yea what a freak!" laughed another snapping the waistband of my underwear.

"I've got an idea!" Laughed the ringleader "Get her up on her feet"

Using the jump rope they had brought along earlier they pulled me over to a tree and tied my hands above my head over a branch.I tried once last time to fight but after a few slaps and punches to the gut they had me subdued enough to get me into position. “Don’t worry we won’t tell them about you being a girl… We’ll show them!” They then yanked my knickers down to my ankles as I could only look down in horror at my fully naked skinny body on show. They ran off then shouting for the boys to come rescue their friend.

I was butt naked, hands tied above my head facing a tree with my bare bottom on display as my friends approached. No amount of tugging could free my hands, I was tied up good. The teens must have been girl scouts in their younger years from the efficiency of the knotts. I had to stand on my tiptoes to relieve any weight from my wrists. I squirmed trying to conceal myself against the tree trunk the best I could as the boys ran over laughing at me for being caught. My crying didn't stop and my boyish-borvado was now totally gone as they teased me for being stripped and letting the girls see my willy. The mortification of standing naked, almost exposed as being a girl was too much for me.

“Nice bottom Charlie!” Laughed one boy as I blushed bright red knowing they were now seeing me totally naked. My friends who I had known for years, staring right at my little pale girly bottom.

“Pull up my underwear please!” I cried hoping there was some tiny chance of getting out of this situation without being caught.

“Turn him around, let's see his willy that he’s been so shy to hide!” laughed one boy loving the humiliation from a playful banter situation. The others obviously just assumed my earlier shyness was because of a small willy, not a complete lack of one!

“Nooo” I wailed trying to kick back at one of the boys, but inovertandly I only managed to kick my knickers off my foot instead.

“Got your undies now!” teased another of the boys holding them up like a trophy. He looked down at my knickers confused, now in his hands the texture didn't seem right, he read the fabric tag at the waistband. “Girls 10 to 11! Hey guys Charlie is wearing panties!” He laughed holding them up for everyone to see

“What!” Laughed another boy grabbing my knickers off the first boy to look himself. “Oh my god he is wearing... ”

He froze looking over my naked form again, my messy hair, almost too long for a boy’s, my girly sobbing, my lovely pale bottom, my girlish figure “Charlie’s a..a...a girl...” He stuttered in total shock. My world fell apart as the unbelievable fact was spoken out loud.

I was broken, letting out a hopeless sob was all I could do now. The boys who were slowler on the uptake in disbelief turned me around for them all to see. I tried to pull a knee up to cover myself but the boys in singular purpose now pulled it away. Their playmate, their confidant, their friends had betrayed them. Naked in public, naked in public and unable to cover, naked in public unable to cover and surrounded by teenage boys! If you could die of humiliation I would have been ten feet under.

Any doubt the boys might have had quickly washed away as they stared down at my exposed kitty. A few growths of fuzz were all that covered me as I sobbed tied up fully naked in front of them. “Charlie’s a girl… a naked teenage girl” one added as if that wasn't totally obvious to the rest of them. I blushed the deepest red I ever had, a blush that spread to my chest as my once friends burst into laughter soaking in the lustful sight of my skinny naked form.

“A naked teenage girl with no tits?” laughed Johnny

“Maybe just a naked little girl who wants to play with us big boys”

“Well maybe we should show her how we play with naughty little girls who try and spy on us”

Any hope of being released quickly washed away. I noticed through the tears streaming down my eyes that all of the boys now had boners again. I couldn't enjoy this however as I was the cause. In the distance behind the boys I could see the girls laughing and pointing from behind a bush. However,the other girls witnessing my humiliation was a drop in the ocean of my shame.

“Please, I’m sorry” I wailed as my former friends looked me up and down, lust in every gase.

“What should we do with her?” One boy asked Cody the ring leader.

“Maybe give her a canning? Find some switches and warm her bottom up” Johnny added hopefully.

Oh god, I had thought being seen naked was the worst thing that could happen to me but maybe the boys would take some petty revenge on me for my deception now they had me tied up. The thought of my once friends hurting me brought a new wave of tears to my eyes as fear rushed through me. The worst thing was I would know it was deserved!

“Charlie? Is that even your real name? Why did you lie to us?” Cody asked me eventually. He had been silent on the whole situation so far. He watched me thoughtfully deciding what to do with me.

“Please … I’m ..I’m sorry I didn't mean to” I sobbed “I just ...just wanted to be your friend!”

The next few minutes were a blur as I cried trying to tell them my story. I could tell by their faces the boys quickly dismissed their earlier anger and betrayal. I’m sure most of it was the fact they now had a sobbing naked girl to look at. I tried to answer their questions the best I could but my sobbing lost most of my side of the story. They then let me down shortly afterwards as I quickly grabbed my clothes desperate to get dressed again. I covered myself and couldn't face the boys as I redressed, not that it did me any good, they had already seen my full nudity.

As I dressed Cody threw my knickers over to me and shouted, keeping a respectful distance. “Hey Charlie, we’ll see you again tomorrow but you better be wearing some girly clothes and nice knickers this time or you’ll be in trouble when we call for you” He grinned as I ran away back home. I couldn't believe what had just happened to me, my legs were shaky as I ran back to my Gran’s house. I still had two weeks of holiday left. How would I ever live down being tied up naked in front of the boys? How could I even face them again knowing they had seen my little nipples and exposed sex. Would they even want to hang out with me, a girl, now they knew my secret?

That night I tried to calm my nerves but also found the most confusingly intense sexual release of my life. The events of the previous day played out over and over again in my mind. The shame and excitement mixing into an intense eutrophic cocktail.

After a restless night I awoke terrified of the day ahead. Thinking on Cody's words, although not sure they would even call for me, I dressed in a pair of flowery knickers, matching bra and a short summer dress. My Grandma commented on how lovely l looked and even helped me with my hair. I was shaking as the boys actually did arrive to call for me, but they looked pleasantly surprised to see me looking like a girl.

The first few days were awkward but we soon fell into a new routine and group dynamic. The rest of my summer was one of firsts. Did they see my knickers again? Oh yes, almost every day! Did they see me naked? Only a few times to my relief and in less forced circumstances. However our games changed from that day on, I got my first kiss, my first real sight of a naked willy and learned a lot about growing up to say the least.
Last edited by SDS on Mon Jul 12, 2021 8:42 am, edited 3 times in total.
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Re: Titless Topless Tomboy - SSC 2021

Post by jimmythehand »

Very enjoyable story, as usual. I particularly liked the explanation for why the boys didn't recognise Charlie's obviously girlish traits, something which other stories where girls are disguised as boys often gloss over; they'd always known her to be a boy and that outweighed any other evidence to the contrary. Simple but effective.

I also enjoyed the double reveal - first displaying her to her fellow teen girls as an underdeveloped girl who'd been exposing herself to the boys, then the ultimate reveal to the boys, in which her flat chest and less than curvy figure go from assets in keeping her secret to humiliating secrets being exposed.
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Re: Titless Topless Tomboy - SSC 2021

Post by SDS »

Thanks for the kind words!

Yes I was trying to go for that explanation, I was glad it worked out! I tried to weave in some suspisions from the boys but what teenage boy would ever admit to thinking their friend looked like a girl!

I've also just done a fairly major edit of this story expanding on reactions and humilation scenes as well as correcting a few errrors. Mostly expanding the girls teasing, highlighting their thought on her exposing herself to the boys. So if anyone read it when I posted yesterday there might be a few juciy bits worth a reread! Also changed the story name haha!
Story Trivia: The first draft of this story I almost posted had the boys spanking, canning and being much more mean to Charlie while she was tied up. This however just felt too much like my other stories and didn't really mesh with the happy ending I wrote (a summer of naughty games and kisses with the boys).
With love SDS xx
Last edited by SDS on Mon Jul 12, 2021 9:06 am, edited 1 time in total.
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Re: Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Post by Hooked6 »

Another great story. I too loved the double reveal - first to the girls and second, to the boys. I must say, however, the girls were pretty unimaginative in taking advantage of their victim. I was hoping they would drag things out a bit before reaching the story's climax of revealing our titless wonder to the boys, but that is just me being selfish as I hate to see a good SDS story end. :D

Still, it was "classic" SDS material here and VERY enjoyable!

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Re: Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Post by SDS »

Thanks for the kind words Hooked!

Yes it could have been expanded but I tried to keep it short and sweet so I'd actually finish it. The girls were happy to have a quick humiliation of the weird smaller girl, but had no massive malice against her so didn't take it further!

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Re: Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Post by dublinjohn »

Another fine SDS story, well done.


Based on the ending there is a posibility of expanding this some time in the future and I hope you do (which is always the sign of a good story IMO).
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Re: Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Post by SDS »

dublinjohn wrote: Mon Jul 12, 2021 1:17 pm Another fine SDS story, well done.
Based on the ending there is a posibility of expanding this some time in the future and I hope you do (which is always the sign of a good story IMO).
Thanks! With reguards to a continuatiom, probably not but maybe a random short might fill in some of Charlie's new games with the boys one day... if the stars align and the inspiration catches me!
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Re: Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Post by dublinjohn »

SDS wrote: Mon Jul 12, 2021 2:36 pm
dublinjohn wrote: Mon Jul 12, 2021 1:17 pm Another fine SDS story, well done.
Based on the ending there is a posibility of expanding this some time in the future and I hope you do (which is always the sign of a good story IMO).
Thanks! With reguards to a continuatiom, probably not but maybe a random short might fill in some of Charlie's new games with the boys one day... if the stars align and the inspiration catches me!
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Re: Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Post by Executionus »

Great story (now that I've finally gotten the chance to read it)! It definitely fit pretty well with how I envisioned the prompt, and created its own unique setting as well. The reveal to the boys was great, with them seeing her bare butt hanging there and them still not knowing that she was a girl.

If I was going to critique it, though, my one big change would be that the "she's a spy!" ending would benefit from an increase in Charlie seeing things that girls aren't supposed to see over the course of the story, before the reveal, even if it wasn't the full package. It would add more to the sunk cost of Charlie's deception as the story went on, with greater risk of serious payback if she were ever to get caught (which, of course, she does). Some examples being the guys mooning each other, or the fact that boys very frequently will pee outside while their friends are nearby. Charlie trying very hard to secretly catch a look at all of their boy parts while peeing (and always failing) would escalate the sexual tension quite a lot just by itself.

I agree with you completely that it wouldn't fit for either the boy group or the girl group to be more extreme with their humiliations, though. Both groups were more in shock from the surprise than anything else, and for the boys this was one of their best friends after all.

PS: I've mentioned before that I look a lot like Loki (thin, long hair, big eyes, effeminate features) and I always have, so let me just say one thing right quick: Teenage boys will ABSOLUTELY tell their guy friends that they look like a girl. A lot. Daily. Hourly.
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Re: Charlie's Unforgettable Summer Swim - Titless Topless Tomboy - SSC 2021

Post by Therese »

That's a great little story. I'd love to read more :)
I think the description of her feelings and reactions are spot on perfect. Very exciting and really well written
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