Sissy Slut Ally

There was a time when we were the kings of the school, having our pick of the girls on campus who were slavishly devoted to us as stars of the football team. That all changed when a new feminist principal took over and decided that everything would be different now that she was in charge. It was bad enough that she wanted to focus the school on its academic pursuits instead and started moving funding away from the football team, but she decided to ban cheerleaders as well!

All these changes were simply too much for us, particularly after taking away our primary outlet for our raging hormones and sexual desires, and we stormed into her office and began demanding that she reinstate the cheerleading team. She smiled at us calmly, which only infuriated us more, but when she began to speak our tempers cooled and we began listening to her intently.

In an almost monotone voice, she asked, “you’re both mad because the cheerleaders are gone?” We nodded in unison as we sat down in front of her desk to hear more of her words.

“It’s because you really admired them.” This was much more a statement than a question. She continued, “The time you spent preying on them, exploiting their vulnerabilities to serve your sexual needs, you were trying to learn how you could be like them. You wanted to learn how to take their place so that they could be free to study and become strong women while you worshiped cocks and could serve as outlets for the pathetic male frustrations in the school.”

Her words became our truth as our psyches were rewired to accept what she told us we had always wanted. We watched as she reached into a drawer in her desk and pulled out a couple of the old uniforms that we had always admired… not because they flattered the girls we lusted after so nicely, but because they made us feel slutty when we wore them and helped us attract more guys. She set them in front of us and we quickly disrobed from our ugly male clothes so that we could put on the sexy uniforms that we had clearly wanted to wear our entire lives.

She handed us each a clitlette cage, since we were such horny and naughty gurls that needed more supervision to prevent us from playing with ourselves all the time. As I stuffed my flaccid sissy stick into the metal cage, it felt extremely affirming to be locked up and have my out of control desires taken care of for me. I smiled at my bestie as we heard the loud “click” that trapped us in our metal prisons for the foreseeable future and then happily handed over the keys to our sissy sticks to her for safe keeping. We were so lucky to have a strong woman look after us once we decided to begin transitioning into outlets for male pleasure.

As we slipped on our blonde wigs that we would wear until our hair grew out, everything about our appearance felt natural. She told us to leave her office and have some real girls fix our appearance before waving us off so that she could explain some things to our parents. I took my bestie’s hand and we bounded into the hallway, looking for our former girlfriends to show us how to look as pretty as they did. If our former girlfriends thought anything was amiss with seeing their former boyfriends bound up to them in cheerleader uniforms begging them to help them look more girly, they didn’t show it as they enthusiastically took us under their wing and hurried us to the girl’s locker room to help us remove all our ugly hair and to slather on the makeup that we would learn to become obsessed with for the rest of our lives.

We were far from the perfect specimens of femininity that we were now, but even on that first day a few of our former teammates on the football team noticed our new looks and responded by groping our smooth bodies. One brave boy went as far as shoving a finger in my ass, which I responded to with a loud and appreciative groan, before noticing that it was one of the nerdy kids that I used to bully. A sneer crossed his face as he pulled me away from the group of admirers who were distracted by my bestie and dragged me into a bathroom before throwing me into a stall.

I knelt in front of the boy… no, the man and looked up at him in both a mixture of trepidation and excitement. I had been on the other end of this exact scene myself with countless girls so I knew exactly what he was thinking as the excitement of having so much power over a scared creature who only needed a little push before becoming the cock-hungry slut she was born to be. As he clumsily reached for his fly, I instinctively backed away as my natural fear took over my body, causing him to slap my face hard enough to knock the wig off my head. Although I was still frightened, I could feel my sissy stick stir in its cage, as the memories of me treating other girls in much the same way flooded my mind.

I realized that the reason why I kept preying on those girls was because I had always wanted to feel what they were feeling… the joy and ecstasy of submitting to a real man. Now that I was honest with myself and the principal allowed me to become a sissy, I was able to experience the fantasies that I had been too afraid to admit I had only a few hours ago. If my femme-boy appearance revealed by the loss of my pretty blonde wig turned the boy off, he didn’t show it as he grabbed by natural short hair and pulled me to his now free cock. Although I now realized that my experience with girls was a form of repression, I did learn exactly what men want and how girls can make them happy. It’s how I inherently knew how to handle the cock in front of me, kissing the head and discovering firsthand the wonderful taste of a real man’s musk before reaching out with my tongue to slowly lick the shaft.

I could hear him moan in pleasure at my ministrations, but he soon grew impatient and forced my mouth open before shoving his cock inside my waiting mouth. As I felt him lower himself into my throat, I realized that my pleasure should always be secondary to the needs of the person using me. It didn’t take long before he started to violently fuck my face, the sounds of my gagging encouraging him to be more forceful, but despite the physical pain I was feeling I was practically in a state of bliss with each painful thrust down my throat. I could feel my own body building to an orgasm at the same time as the boy raping my mouth and my mind exploded into an indescribable ball of glorious pleasure when his cock twitched and his seed began to shoot down my throat.

When he started pulling himself out of my mouth, my mind started to clear and I was so happy that I could finally experience the pure joy of servitude that I had desired all along. I didn’t even notice that my little clitlette was still painfully struggling in its cage, emitting my sissy juices onto the cold tiled floor of the bathroom, as I simply sat and basked in the overwhelming happiness I felt discovering my true self. As I reached down with my hand to wipe up my mess from the floor, I watched as the boy who deflowered my mouth picked up my wig and used it to wipe his cock clean before placing the wig back on my head. He gently pet me and told me, “I look forward to using you every day”, to which I responded by swooning and playfully licking the sissy juices on my hands clean.

He quickly left to go to classes, and I took a few minutes to compose myself from the bliss of being used before standing up to try to clean myself in front of the mirror. I was thankful that my ex-girlfriend had given me her makeup kit so that I could quickly reapply the thick globs of foundation, mascara, and lipstick to my tear and cum-stained face. Moments later, I heard the door open and saw my bestie stumble in with a dazed and happy look on her face. From her equally disheveled appearance, I could tell that someone had their fun with her as well and I practically leapt on her to give her a congratulatory hug.

She was so happy telling me about her own first experience, of how the English teacher he used to annoy in class pulled her out of the hallway and started raping her mouth in the faculty lounge, that I couldn’t help but give her a passionate kiss midway through her story. She looked surprised, but her shock soon faded to excitement and adoration and we spent several minutes with our lips locked together as we heard the metal grinding of our caged sissy sticks rubbing violently against each other. Knowing that we could share our love for each other but could only seek relief from serving someone else, we reluctantly broke off our kiss and tried our best to help make each other presentable. This would become a near hourly ritual in our lives soon enough.

No one minded that we reeked of cum when we scampered into our next class late – in fact it only encouraged more of the braver boys to use us and add their own cum to the collection that was slowly drying on our wigs and uniforms. By the end of the day, I had served four of five cocks and was content, but could definitely feel the urge to serve more men building inside me. But it was time for us to go home to our loving families and tell our parents the great news.

My bestie and I just knew that we should both go to my home because that’s where we both lived. By the time we arrived at my house, we remembered that our mothers had moved in with each other and became lovers shortly after realizing our fathers would never be able to satisfy their sexual desires. When we walked through the front door, we could see our pathetic fathers dutifully prancing around the house in maid uniforms performing the chores while other mothers sat in the living room happily sipping glasses of wine while playfully flirting with each other.

When my mother noticed us, she motioned for us to approach them so that they could examine us more closely. As they looked over our garish makeup and our cum-soaked cheerleader uniforms, they nodded approvingly, particularly at the metal prisons that had affirmed our sissyhood. My mother explained that the principal had called them and had a long conversation with them, explaining many things but most importantly emphasizing how as mothers they had an important role in supporting our transformation. They’d keep a strict eye on our behaviour, diet, and of course our consumption of female hormones to make sure we were on track to becoming the cute cheer-sluts we so desperately wanted to be.

I watched out of the corner of my eye as my bestie’s mom was gently caressing my bestie’s body, especially her ass, before my mother explained that they would make sure our bodies were properly trained as well. I didn’t have time to ask her what she meant as our mothers quickly slide off their skirts to reveal moderately sized strap-ons pointing appetizingly up at each of us. My bestie and I quickly dropped to our knees and began sucking, which made our moms laugh before patting our heads in encouragement. After a few minutes, our mothers told us to stop and stand up, directing us to lay down stomach first across from each other on the coffee table.

My bestie’s mom told us to look at each other and hold each other’s hands tight, telling us that we were going to start the next phase of training at home before she stood behind my bestie and hiked up her short cheerleader skirt. As I looked deeply into my bestie’s eyes, a flicker of recognition crossed each other’s faces as a part of us knew that something was wrong. Before I could think too much about what that could be however, I could feel the violent entry of my mother’s cock plunging itself into my ass and a flash of pain spread throughout my body.

I could see a look of confusion spread across my bestie’s face as she struggled as much as I did with her mother fucking her ass. Why were we so happy as sissy gurls? Why did we accept our new lives so readily? We were going to speak to the principal about something important to us, but…. what was it? These questions were literally fucked out of us as I saw my bestie’s eyes roll up in pleasure as she started to squeeze my hands tight with each thrust her mother gave her. I could feel my own doubts slip away as my mother’s violent pounding built to a fever pitch, as the only thing that mattered to me in that moment was the full feeling in my ass-pussy as it was being fucked by my goddess of a mother.

My fingers dug into my bestie’s hands as I felt my own orgasm build to a fever pitch before my sissy slut exploded and released its goo onto the floor. I could feel my mother reach her well manicured hands around my neck before grabbing me by the throat and leaning down and pressing her heavenly breasts against my back so that she could whisper in my ear and tell me that I was her beautiful little sissy slut girl. Joy and pride washed over me as I built to another orgasm due to my mother’s expert fucking and her encouraging words. I remembered what I was trying to formulate in my mind before – I wanted to thank the principal for making me realize what I was and being so supportive of my transformation.

After what felt like hours of being fucked, our mothers finally stopped and dismounted us, giving me a moment to rest and look at by bestie who was probably as tired but as happy as I was. Our mothers sat down on the couch next to us and began to kiss each other as they admired their beautiful girls and the training they just provided. It wasn’t long before my mother barked at us and told us to stop being so lazy and return the favour. I didn’t understand what she meant, but when our mothers spread their legs and began to play with their own clitorises, I gave a knowing look to my bestie and knew exactly what she wanted us to do.

We dragged our tired bodies off the table and crawled over to our mothers, nestling our heads between their legs before tentatively reaching out with tongues to gently lap at their pussies. The smell of my mother’s womanhood, a mixture of precum, piss, and blood, aroused me to no end as I practically dove in after my initial probing and began probing the folds of her pussy with my tongue as if I was licking clean the most delicious plate of food I’ve ever had. Yes, there was a pure joy that came from being used by a man, especially one that treated me with contempt, but there was something completely different about serving an older woman who used me out of genuine love. Feeling her thighs press against my head as her body clenched in pleasure made me so happy that I was able to bring her as much pleasure as she just did earlier when she took the time to take my anal virginity.

When our mothers were satisfied with our ministrations, they praised us again for being such good gurls before waving us off to go clean ourselves up and to get ready for dinner. We left our mothers to enjoy each other’s company after their own orgasms as we bounded upstairs to get clean and have our first shower together. Since my bestie was also now my sister, it made sense that we’d share everything – not only our bedroom and the same bed, but our baths and showers too. We tried our best to focus on getting each other clean instead of licking each other’s bodies – we noticed that our nipples in particular were extremely sensitive and would send us jolts of pleasure – but we were reminded that our mothers were waiting for us and reluctantly stopped so that we could dry ourselves off and ran to the room we shared so that we could reapply our makeup and our wigs and put on the cute pink pajamas our fathers had laid out for us as part of their chores around the house.

By the time we went back downstairs for dinner, we could see our fathers dressed up in fancy gowns ready for an evening out with a series of dates that they would take back to my bestie’s old home. It was only right that they’d spend the night whoring themselves to bring in some extra income for our mothers after all. We gave them the compliments that they were clearly fishing for as they waited for us to notice them before they left and went into the dining room to have dinner with our moms. It was a wonderful meal that we shared as a family as we dished about the boys we served and gushed about how wonderful our principal was. We ended the night by kissing our mother’s heels goodnight before bounding hand-in-hand to our bedroom, where we cuddled up in my tiny twin bed and we dreamed of new ways we would be used the next morning.

This began our slow transition into full femininity through the school term as the people not only encouraged our new whorish personalities, but several members of the now defunct football team saw our example as an opportunity to become cheer-sluts themselves and joined the new sissy cheerleader team that we captained. Even our former coach, who we thought would never agree to disbanding the team, not only happily encouraged us to live our new lives serving the boys we used to look down on, he quit his job so that he could live his life as a beautiful woman working as the principal’s personal secretary. In fact, we’d often hear her under the principal’s desk when we went for our special guidance counseling sessions, envious of how the coach was able to serve the strongest and most beautiful woman at the school.

To outsiders, it was a principal focusing on academics and creating a welcoming environment where gender roles were questioned and students were free to express their identities without the shackles of toxic masculinity. In a way, the principal was right… however she just realized that all men, even the meek bullied nerd or the tormented teacher, would need an outlet for their evolutionary urges, and rather than try to have them repress their desires, it made sense to give them an outlet. And what better outlet than misogynist men who were simply “repressed” sissies that needed a little “push” to get them to embrace their true purpose in life? The fact that our mothers needed a little speaking to in order to come to her way of thinking was just part of her service, working with parents to ensure the best for her students.

By the end of the year, our bodies had really begun to blossom thanks to the cocktail of hormones. My bestie was even gifted with a set of breast implants to make her look much more voluptuous. I was jealous at first, but the principal told me that keeping me flat reminded her of her most troubled student that she had helped and she enjoyed seeing my tiny tits on my small frame… and who was I to question how she enjoyed me? Both of us even got our final bottom surgery, long removing our sissy clits and replacing them with wonderful cunts that would help use serve more men and older women in the future. Certainly our grotesque pleasure derived from our sissy releases weren’t important to anyone but us, and our pleasure didn’t matter at all, so it was fine if our orgasms were now muted and mostly for show. As long as our partners came, we were happy!

Of course, even after our surgeries, the principal kept us locked in chastity belts to which only she held the keys. Even our mothers didn’t get to see our new cunts, but they were happy enough with our oral skills and our asses if they felt like exerting their own masculine energy and wanted something to fuck with their strap-ons. At first, we thought this was so that we could properly heal, but we had been kept locked up for much longer than that. It was today, on the eve of the final days of the school year, that she told us that to wait outside the school by her car for a special surprise.

We lent against the wall, standing with her hands together, and smiled as we saw her leave the school and walk with purpose to her car. Our former coach practically waved her off before crawling back into the school to help relieve the sexual frustration of some of the school’s administrative staff, but she ignored him and strutted toward us before giving each of us a deep kiss and telling us to get into the back seat.

As we drove off to her house, she noticed our sexual frustrations bleeding through our obedient girlish personality despite our best efforts. She had told us not to fuck anyone today, and we obeyed her unconditionally and spent the day fending off the advances of many men and some of the women who wanted to us for relief. We were lucky to have such a large and dedicated team of sissy cheerleaders who could fill in for us, but there were always people who wanted to fuck the captains. She waved back at us and told us that we could kiss each other while we were en route, which we happily did, practically jumping on each other as we shoved our tongues into each other’s mouths.

It wasn’t long before the car stopped and we stepped out, entering her fairly expansive and well kept home. A beautiful but whorishly dressed woman welcomed us at the door, teetering on her impossibly high heels and in an extremely tight and low cut pink dress, who we soon realized was her former husband. Apparently her sissy husband used to play football as well, before he saw the light and realized his place was as a sissy. She shooed her sissy husband away and he meekly obeyed, giving us a sad look of envy before mincing away to his next chore.

She turned to us and pulled our chastity keys out from between her breasts, jingling them in front of us with a sly smile on her face. She turned around and started walking to the set of stairs, the clacking sound of her heels on the hardwood floors mesmerizing us as much as the jingling sound of the keys as we followed behind her like a pair of puppies. As we reached her bedroom, she sat down on the bed and told us to step forward. My new cunt was practically gushing as I could feel her reach for the lock on my chastity belt and slip her key into the hole. I could have sworn I came the moment I heard the distinctive clicking sound of the tiny lock opening itself before the belt slowly felt from my body. My bestie was next, and from the small gasp that escaped her lips I could tell that she felt the same amount of joy at being released from her prison and having her cunt finally exposed and ready to be used.

Our principal explained to us how she grew extremely fond of us, something she hadn’t expected when she decided to use us to help shape the school in her image. Our cunts simply dribbled out precum as we watched her strip in front of us before reaching for a massive strap-on dildo that she had neatly placed on her nightstand. She smiled appreciatively at our cunts and joked, “I won’t have to use lube now, will I?” before giving me a violent kiss and grabbing me by the hair so that she could throw me onto her bed. My bestie whimpered because she wasn’t chosen first, but knew better than to pout too loudly lest she seem ungrateful, and watched as she hopped up after me and spread my legs, watching me as my body quivered in anticipation at finally losing my virginity.

She roughly flung my legs open and climbed up on top of me and give me another kiss before expertly penetrating the cunt she had a huge part in helping me get without breaking eye contact with me. She said something cryptic, “I want to see the last part of you die as you learn to love the feeling of my cock and learn to serve me forever,” as she started violently thrusting inside me. I didn’t know what she was talking about, but I could feel tears starting to form in my eyes as she continued to fuck me with a sneer on her face. I’m sure these were tears of joy, even though there was some lingering doubt in my head, but I pushed those doubts away after she reached down for another kiss before licking some of my tears away. She continued to pound me and it wasn’t long before her rhythmic pounding led me to my first orgasm as a fully-fledged girl.

In a height of madness, I blurted out “I love you!” which was met with a howling cackle as she slowed down and started come down from the orgasm she had from dominating me and confirming my servitude to her. She quickly climbed off of me and motioned for me to move over beyond telling my bestie to take my place. As she started to fuck my bestie, I could see tears forming in her eyes as well as she was being fucked by our wonderful mentor, and I reached out and held her hand and smiled knowing how happy she felt now that she wasn’t a virgin anymore. We were both so lucky to have such a wonderful woman guide us into womanhood.

It wasn’t long after that our principal collapsed in between us and we cuddled next to her, giving her gentle kisses before she started to explain how she had decided to keep us. My heart was practically bursting as she told us how she would hold us back indefinitely so that we could help find equally troubled boys who were born to be members of our sissy cheerleader squad and how we would be her playthings both at school and now at her home. As she reached with her hands down to our crotches and started fingering our still eager cunts, whatever silly doubts I had were forever gone as I was happy to be her collaborator and servant for the rest of my life. From the silly look on my bestie’s face as she had yet another orgasm, I’m sure she felt the same way.

If I wasn’t so horny and tired, I’d almost want to jump up and start doing the school sissy cheer to show my pride at being chosen by our principal. But there would be countless more opportunities to show her how happy I am to be a co-captain of the sissy cheerleader team!