I'd never fit in at boarding school. Never had too many friends. Never hung out with the 'cool' kids. Never got with the 'popular' girls. Not for lack of trying. I'd hoped things would have changed in my final year. I imagined a summer of adolescence would see me come back transformed. But unfortunately not. The only dramatic changes were the girls. Skirts got shorter, shirts lower and curves started appearing. This made my time as a lonely kid on the outskirts all the more frustrating.
That's why I was so confused when I received the message.
'Hi, saw you looking in class. Don't be so shy. Come see me in the old groundskeeper's hut. Tonight. 12:00. Don't tell anyone.' - Phoebe
There was every chance she caught me looking in class. She was by far and away the best looking girl in school. And her best friends were the next best three.
Phoebe had long blonde hair that waved down either side of her face, framing her shocking blue eyes. She was tall and slender, and on her return from another summer away to some tropical beach, she'd acquired a stunning new golden tan. Which she didn't hesitate to show off. Her shirt only buttoned half way, collar pulled wide open. Flaunting her chest and cleavage. Something about the contrast in her tan, and the pale skin left from where her bikini had been sitting drove me wild.
I spun round when I first opened the message. Expecting to see crowds of people bursting into fits of laughter, pointing, but nothing. I say first opened the message, as I must have opened it once every five minutes since I received it. Checking it was still there, that I hadn't imagined the whole thing. Could this be real? Imagine if it was and I didn't go? I couldn't risk missing this opportunity.
Sneaking out of the dorm at 11 was a breeze. An art all decent boarding school boys had perfected after years of sneaking out to smoke and drink. The groundskeeper's hut sat at the very edge of the school grounds, nestled just inside the edge of the woods that bordered the school. It hadn't been in use for long before I started at the school, everything was sub-contracted out now. But still the decrepit hut stood, a reminder of times past. Half collapsed roof and smashed in windows, it was where most of the lads went to smoke weed and start fights. What on earth would a girl like Phoebe be doing in a place like that? That should have been the first of many red flags. But I was too excited to be partaking in any vexillology.
I skirted the edges of the forest for fear of being spotted in the open, by the time I'd reached the hut the moon was at its highest. Illuminating the place in an eerie light, my stomach filled with nerves. This was my chance, my chance to change my life. I'd never kissed any girl before, never mind done anything else. And my first was going to be Phoebe. Hottest girl in the school Phoebe. Gets dropped off at the start of the year by helicopter Phoebe. Holidays in Greece with the children of actors Phoebe. What on earth was she doing seeing me? Red flag number 2.
It was 15 minutes to 12 when I reached the back door of the hut. The sound of my heart pounding in my chest only drowned out by the steady creak of the door as I eased it open. Anticipating what was waiting for me inside. It only took a couple of seconds for my eyes to adjust to the dark so I could see I was alone. I was here first. Was she on her way? The thought of her skirt in the breeze outside, revealing the bikini line on her perfect ass, had my dick growing in my pants. Oh my God I was so excited. What was she going to do? The vibration in my pocket answered the question.
'On my way, we don't have long. Be ready for me. Naked. And hard. I can't wait to see your cock.'- Phoebe.
I usually think of myself as quite intelligent. But in this very moment my dick overruled all other sense of thought. Without hesitation I started kicking my shoes off and unbuckling my belt, fully thinking I was about to lose my virginity to the hottest most popular girl in school. I threw all my clothes in a pile on the floor, left standing in the middle of the room fully naked. I spat in the palm of my hand and started stroking my cock, desperately trying to get it to look its biggest for when she arrived. That's when my world turned upside down.
The doors of the cupboard and two other rooms in the hut all burst open simultaneously, out jumped 3 girls. I recognised them immediately, Phoebe's best friends. Chloe, Amber and Ruby. All wearing the same uniform; emerald green plaid mini skirts, crisp white shirts, and knee high grey socks. In each of their hands their iPhones, torches on, pointing directly at me. Hysterical laughter filled the room as they all pointed, I desperately crouched trying to cover up as much as I could. But it was too late, they'd gotten everything the needed. I heard the familiar creak as the door opened again behind me, I spun to watch as Phoebe slowly walked into the room smirking.
"You really thought I was going to fuck you?" The other three girls all tittered as she spoke. "You're even stupider that I thought. Smile for the cameras."
The flashes surrounding me all started going off sporadicly.
"No, wait, please." I stuttered, desperate to get my words out.
"No, wait please." Her imitation whiney voice stung. "Look, we have all the pictures we need to ruin your life. Videos of you desperately wanking your little cock, spitting on your hand. Imagine if these got out to the school. Your life wouldn't be worth living." I couldn't help but agree, that would be social suicide. I wouldn't be able to move at school without hearing the laughter and abuse. No-one would be seen dead near the boy that sneaks to abandoned buildings to strip off and jerk off.
"But we have a way to make all this go away. All we want to do is play a game."
"A game?" I was curled into almost a ball at this point, desperately trying to hide my cock from the girl of my dreams.
"Yes." She threw a clear plastic chastity cage on the floor in front of me. My heart sank when I saw it, years of getting off to literally anything and everything on the internet meant I knew exactly what it was. "This is your incentive to play our game. You lock your little dick in this chastity cage and play our game, and we won't send out these videos to the entire school."
"A chastity cage... I can't"
"It won't be on forever. You will be unlocked at the end of the game. We promise. What reason do you have not to trust us?" This circle of girls all began chuckling again as I reached down to pick up the cage. I had no choice. The embarrassment and cold had quickly sorted my erection out and it was depressingly easy to slide my flaccid cock snugly into the small plastic sheath. Everyone watched intently, the room seemingly holding its breath as I slowly looped the open padlock through the loop.
"Lock it." Phoebe ordered.
That click pierced the silence like a dagger, a moment that will stay with me forever. As will the way the faces of all the girls lit up immediately. Ruby grabbed a chair from the corner of the room and placed it behind me. Chloe gently pushing me into a seated position.
"Now what are the rules of this game? I'm sure you're thinking. Well we each have key." Phoebe pulled the chain around her neck up, and a small silver key rose from deep within her cleavage. "Only one of these is they key for your cage. Every Monday at midnight in this room you will get a chance to guess which key will unlock you. If you are correct you a free to go, unlocked, safe in the knowledge our little videos will be strictly for personal use. Game Over." She paced back in forth in front of me as she spoke. "Or! If you're wrong. You'll get a punishments, which you have to complete for each of us. Until your chance to guess again a week later. Simple really?"
I nodded.
Week 1:
"Well let's not waste any more time and get stuck in. Which of us has your key?"
They all stood in a line in front of me, holding hands. I stared at each of their tits, and they chains that fell between them. The shining silver on Ruby's darker skin caught my attention.
"Ruby?"
Silently she stepped forward and knelt between my legs. Gently placing the key inside the lock, careful not to touch any part of me, she turned it. Nothing.
"Ohhh, unlucky. Tonight you're ours." Ruby looked up at me as she spoke. She had deep brown eyes and frizzy hair. As she stood up and walked away I couldn't take my eyes off her ass. It was much larger and rounder than the others, the mini skirt made no attempt to cover it up.
Phoebe stepped forward again, not even trying to hide her delight. "You're first punishment? Dress up. Complete a task for each of us now, and you'll have the opportunity to guess again next week."
It was Chloe's turn to step forward and speak now.
"It's such a shame we're all matching but you, you must feel so left out!" Chloe was the shortest and slimmest of the girls. Long brunette hair, a shocking pink bra clearly visible beneath her see-through shirt. "Good job we brought you a spare. Amber?"
"Shit." Amber slammed her forehead into her palm. "Why did you leave it with me, of all people?"
"Fuck it." Chloe didn't hesitate. "He can have mine."
She slowly started to unbutton her shirt further. I was transfixed as she revealed her large soft tits, she threw her shirt to my feet. She unzipped her skirt and I felt my dick start to strain against the hard plastic as I saw she the matching shocking pink thong she had on. She turned and bent over, ass inches away from my face. So close I could smell her pussy as she gently pulled the thong down, exposing her glistening pussy lips. At this point all the other girls already had pulled their skirts up, rubbing themselves through their own panties. Enjoying the show as Chloe removed her bra and placed it on top of pile and stood there, as naked as I was. They key round her neck hanging low between her tits.
