A year of jockhood came and went, daily workouts, buzzed head, sweaty gym shorts. Though you were stronger and more comfortable than ever, you missed being preppy. Looking back at the old photos from when you wore chinos and polos instead, you remembered how you felt then: disappointed you werenât living the jock life.
âIâm not sure what to do,â you confess to Sir. Heâs the one putting you through your paces, holding you to your meal plan. He was the one who gave you your first buzz, clippers set to 1. âThough Iâm living my fantasy, and I feel confident, I keep feeling like Iâm missing out on all the other versions of me. This was supposed to be my final transformation, and despite all the mental training, I just canât stick with it. Iâm sorry Sir, I fear Iâve disappointed you. I know youâve put so much effort into training me.â
Sir isnât angry, nor let down. Heâs pensive, eyes out of focus, forehead furrowed. Then, with a sudden smile, he starts: âBoy, itâs no problem. Iâve seen this before. Sensed that it might happen. Itâs just that I wanted you to have the full jock experience you were so dedicated to when we first started. I know just what to do. Another year of trainingââ
âAnother year?â you blurt in disbelief.
âShush, boy,â he continues, stern now. âThis year will be unlike the last year. Rather than get you deep into one identity, weâll change things up every month. Weâll explore all the different versions of you. Then decide what to do next. Who knows, maybe youâll be begging to go back to jock mode.â
Your mouth is open. âW..wellâŠâ you say, processing what Sirâs suggesting. It tingles, excitement gripping you, and you decide to comply. âYes Sir!â you shout. Heâs already thinking of what youâll become, and within the week, youâre given your first identity.
January you kept your hoodies and trainers, but grew out your hair slightly on top even as the sides were shaved. You wore a steel necklace and a tracksuit. Manspreading, walking with a swagger. Drinking and cursing. Watching porn. Sir would catch you by surprise and pin you against the wall, getting his pleasure from you. You loved the sudden lack of discipline, the spontaneity, the cockiness.
February your hair was long enough to part and slick. Your wardrobe was entirely replaced with white briefs and singlets, gray and blue dress shirts, smart slacks, knee socks, shined shoes and even a pair of short elasticated wool shorts for home. You tucked in your shirt every day, followed a structured schedule, and learned the basics of piano and French every evening. Sir would spank you for the smallest transgressions. You came to enjoy his discipline, the way your energy was controlled and focused on learning.
March your hair kept growing. You returned to sporty shorts with matching silky shirts. Leg day every day. Running, endurance. Sir had chosen only two outfits for you to wear. It made decisions easy. He chose your food carefully for energy. By the end of all the workouts youâd be ready to head to bed, but you were quizzed on football stats every day from the games you spent hours watching. You lived through your teamâs performance, trained hard to emulate your favorite players. Sport, sport, sport. The month passed quickly.
April you didnât get a haircut, just put a little hair gel in it. Polos and khakis or bright, short shorts. Boat shoes. You started to drink again. Spent lots of time on social media, taking lots of selfies with vapid pearly smiles. A lot of them involved golf, which you were now taking up. Sir got you invited to a party on a yacht. Little discipline again, just spending money, and enjoying the money others spent, and the respect everyone gave you.
May you used a straight iron and bobby pins. Pink crop tops and pink high tops. Became a go-go dancer, shaking your butt every time someone slipped a sweaty dollar bill down the waistband of your glittery hot pants. Pumped your nips every night and morning. Sir worked your hole every morning until you could take a plug, then a thick dildo, then a fist. Sometimes, after your shows, youâd get the chance to fit other guysâ hands up your hole too. It felt good to be desired, great to be a slut, and utterly fabulous to be so flamboyant.
June you got a cut in front and a trim in the back. Button-ups with the snaps, tucked into tight Wranglers and secured with a massive belt buckle. You listened to country music the entire time you were awake. Spent time hunting and fishing, dressed in camo and/or waders. Beaten-up T-shirts and trucker caps half the time. Cowboy hats the other half. It was relaxing getting back into nature, relaxing listening to repetitive songs, relaxing to slip completely into this identity and hear the voices of anxiety silenced. Some time every day, Sir gave you hearty pats on the back, and butt, and you embraced him, totally at ease.
July you awoke in briefs and a singlet again. An extra-large polo shirt, sweater vest, and loose polyester dress pants were stuffed over you, and you were taken to a barbershop and given a tight waxed horseshoe flattop with a white, shiny, wide landing strip. Glasses for good measure too. The only fun you had was DnD, but mostly you were too busy reading academic papers, solving logic puzzles, and arguing with strangers on Quora to spend much time on the DnD sessions. Sir would turn the Internet off at 9 every night, though, and youâd have to wake up early the next day to catch up on your online pursuits. It felt good to know more than anyone else...except Sir, of course.
August you got tired of feeling like other guys were about to bully you and became the bully instead. Buzzed again, gym shorts, tank tops, lifting, protein shakes and meal plans: all the things youâd gotten tired of six months ago, but which seemed so comfortable and natural now. You almost didnât want to continue the cycle of transformations. Begged Sir, naked and on your knees, your prominent pecs quivering slightly. Sir denied you. You needed still more discipline.
September you were to follow a detailed schedule to the minute. Your buzz was shaved daily on the back and sides, clippered to a 0.5 on top. You were issued one set of clothes for PT, and one set of clothes for day-to-day wear: a polo and cargo pants with stiff black boots that gave you blisters. There was a final set of clothing for dinners and special outings: a dress shirt secured with shirt stays, immaculately creased trousers, mirror-shined black shoes. Punishments were severe and severely boring: standing at attention for hours, endless sets of push-ups, and marches in circles with the sun beating on your shorn head. Despite the unpleasantness, you felt proud to be held to such a strict standard, and to comply with it at least most of the time. Sir would occasionally reward your compliance with a treat like a single ice cream bar or 20 minutes of free time.
October you asked again to become a jock, or a frat boy, again, but Sir, tight-lipped, shook his head. You hadnât learned your lesson. Stripped of all clothing, you winced as you were shaved head to toe, and a chastity cage was forced on and locked. You were rubbed with lube before being covered in a thick black rubber suit that covered your entire body, zips held closed with a dozen miniature padlocks. You were let out of rubber only for your brief, intense workoutsâfor public matters, a thinner rubber suit that left your arms and legs exposed was fastened on you, after which you donned a plain black T-shirt, black jeans, black Converses and a black snapback. Half the time, a large plug was shoved up your ass. You didnât have a strict schedule any more, but the punishments more than made up for it. Perhaps your entire existence was one punishment. You were beaten, forced into painful positions, your balls stretched, made to drink piss and eat from the floor. You slept in a large dog cage. Slowly, you got used to it, hastened by Sirâs hypnosis and brainwashing sessions. You realized how much effort Sir was putting into the training and resolved not to disappoint him again. The border between pain and pleasure disappeared, and you grew content in the moment, constant intense sensations forcing your attention on the present. For Halloween you were paraded out in your full rubber suit, a collar and leash around your neck.
November you knelt, bound, ready for the next layer of intensity, for a fresh round of humiliation and torture. You accepted whatever Sir might inflict upon you. But he untied you, let you out, gently cleaned you in the bathtub, and had you lie on a towel. It was only when you felt a soft, pillowy sensation enveloping your chastity cage that you realized what heâd planned. You had a large wardrobe of brightly colored T-shirts and pants and a full rack of chunky sneakers. There were rules, of course, particularly around bedtime, screen time, and getting your diaper changed, but you were otherwise free to play as you wished. The lack of punishment initially seemed wrong, like cheating, but you settled into your new pampered lifestyle as Sir gently encouraged you and occasionally told you life stories to learn from. By the end of the month, you were making cucumber sandwiches like a pro, wearing a cartoon sandwich T-shirt and overalls.
December Sir trimmed the sides and back of your head, undressed you, unlocked you from chastity, and showed you to yet another set of clothing. You couldnât make heads or tails of it, but he didnât tell you what you were supposed to become, just smiled and walked out of the room. No kinky gear or implements anywhere, just a fleshlight in the back of the drawer, behind the boxer shorts and miscellaneous patterned shirts and jeans. Sir just kind of...left you alone, not telling you when to wake up or what any consequences of anything would be. With the horniness from the previous months of chastity and discipline built up, you started to jerk off at least three times a day. Sitting at the dinner table with Sir eating pizza, you asked him what this was all about. It felt so wrong.
âBoy, this month Iâm showing you what you havenât had for several years: a ânormalâ lifestyle. No control, no schedule, no denial, no punishments, just...freedom. You shouldnât forget, I can give you any transformation I desire, and this month I want you to be a regular guy. Whatâs light without shadow, a vessel without the internal emptiness, a crisp autumn day without the muggy summer before it?â
Almost crying at this point, you nodded. Youâd taken all this kinky artifice for granted, assumed that last month was Sirâs way of letting you off easy even though you were in diapers. You had gotten so accustomed to Sirâs control that youâd let yourself get tired of living your deepest fantasies as a prep and a jock.
You stood up. âSir,â you started, about to apologize, about to thank him, about to tell him how much you loved him, but you pushed your face into his and gave him a deep kiss, inserting your tongue, feeling his warm mouth relax in pleasure. You hugged him tight, and he hugged you tighter, and you were together, equals now. Wait, equals? That didnât feel right.
You pulled his arms behind his back and scowled. âI love you. Thatâs why Iâm going to do to you what you did to me. Weâll start with you as a jock.â Sirâs eyes widened. You kept your face stern, but worried heâd find some way to punish you. Suddenly, Sir sat up and straightened his shoulders. âSir, yes Sir!â he yelled. And so, another year began, with a Sir and boy playing through various transformations, except the Sir and boy were reversed this time, and a few times, for a month at a stretch, theyâd stop and live as equals, just to appreciate what they had. Appreciate each other they most certainly did.
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