Ella’s Anniversary

It had been exactly one year since Master had found me. One year ago, I still called myself a man. But after Master took me in, I realized what a really was. I was a sissy girl who had been tricking herself her entire life.

It took a few weeks to break me in, but eventually Master helped me realize that I was only meant to serve him. Now, I eagerly help him everyday with his chores, cooking, and most importantly, his sexual desires.

About a month after I met Master, he locked me in a chastity cage, telling me that sissies don’t get hard and don’t deserve to cum. Well of course! My only goal is to pleasure him, and my own pleasure is secondary.

However, with our anniversary night coming up, Master told me that he would give me a nice surprise, and I couldn’t help but get excited for what was to come.


“How long have you been my little sissy girl, Ella?” Master asked. I gushed at the way he said my sissy name.

“I’ve been your little sissy for one year now, Master,” I responded energetically. I was kneeling in front of him on the floor of our bedroom. I was only wearing a pair of stockings and a bra underneath my dress, so I could feel my little clitty dripping out of my cage onto the floor. But I did nothing about it, since Master told me not to move.

“And do you remember the last time you had an orgasm?” Master asked.

I turned red, both because the question turned me on so much and because I couldn’t really remember. “I think the last time I had an orgasm was about a week after I met you, Master,” I answered. The thought of my own orgasm was enough to make me leak even more. There would definitely be a puddle on the floor under me.

After the one time I had an orgasm, Master hadn’t let me cum again. It had been a long year of constant denial.

“Do you know why I don’t let you cum, Ella?”

Shortly after meeting Master, I had come to find out why he was always denying me an orgasm. He never directly told me, but I had come to figure it out soon enough. “B-because a good girl should only focus on serving her Master,” I stuttered.

“That’s right, Ella. And if you are able to simply cum whenever you want, that wouldn’t be fitting of a sissy like you, right?”

“Yes, Master.”

Every time Master fucked me, he would always bring me right to the edge of an anal orgasm, and then deny me. Usually, he came inside me right before I could cum myself or he would finish in some other way. Sometimes he would let me beg to be allowed to cum, and sometimes he would just tell me to clean up quietly. I always did what he wanted me to do, but he had never allowed me to cum. Because of this, I was constantly horny, always ready to please him in hopes that he would let me cum if I did a good job.

“Well, Ella, I think it’s time for a reward.”

My eyes lit up. “Really, Master?” I couldn’t hold back my excitement. Before I could say any more, Master pulled down his pants, revealing his large member, which had already started to get hard. He must’ve been just as excited as me.

Looking at his big cock, I could tell why I was a sissy. Even when he wasn’t fully hard yet, it must’ve been two or three times bigger than my own when I was fully hard. And with the cage on it, my little clitty seemed comically small in comparison with Master’s cock.

Master held his cock in front of my face. I knew exactly what he wanted me to do. I could smell his strong, musky scent that I had only dreamed of having when I still called myself a man. The tip of his cock was already glistening with his precum.

I greedily opened my mouth wide and took in the girth of his member. Even after one year of being with him, I hadn’t gotten used to his size. With my jaw stretched wide, I was just barely able to wrap my lips around his cock, which was now pulsing with heat and masculinity.

Master grabbed the back of my head and started thrusting his cock into my mouth. I greedily took it all in, allowing the head of his cock to push past my throat. I gagged and started tearing up, but I held the position, knowing that I was pleasuring Master. He pulled his cock all the way back out, then pushed back into my waiting mouth. Every time the head of his cock pushed past my throat, I gagged and coughed. I could tell my mascara was starting to run down my face. But I knew he loved that look. And I did, too. I was feeling like a true sissy slut.

After a few minutes of Master’s rough throat-fucking, he pulled his cock out of my mouth.

“Fuck, Ella, I’m about to cum,” he groaned.

I grabbed his thick shaft. Using both of my hands, I worked up and down his thick cock, coaxing the cum out of his heavy balls. It wasn’t long before Master sprayed his warm cum all over my awaiting face. I put the tip of his cock back in my mouth and sucked out the rest of his load.

Even though Master had just cum, I knew he was far from being finished. And I wasn’t close to being done either.

Master picked me up. In his arms, I felt so small and weak compared to him. I was truly his little sissy girl. Master dropped me on the bed. In his wild lust, he ripped the dress off me, exposing my slender body. I got on all fours and faced away from him. I wiggled my bare butt at him, giving him a little tease.

I could only imagine the sexy sight that he saw. A sexy little sissy girl, caged up and only wearing a lacy bra and a pair of stockings. I waved my tight little hole for him, and my locked clitty swayed between my legs, dripping a long, thin line of clear precum.

I turned my head to see a wild look in Master’s lust-filled eyes. He grabbed my hips and aligned his member against my smooth, hairless crack. The rough mouth-fucking that he’d just given me was more than enough to lube up his cock. Master pulled his cock backed and lined it up with my eager hole.

He waited a moment, which seemed like forever to me. I was so turned on and horny, I tried to push backwards into him. I needed his cock so badly.

Then he gave me what we both wanted.

“Oh, fuck!” I moaned when Master drove his monster cock deep into my sissy hole. Master had not fucked me for the past three days in preparation for this night, so it felt like my first time again. My tight little hole could barely handle the size of Master’s huge cock.

With a deep groan, Master started fucking me with a passion that I had never felt before. Master’s cock felt like a hot iron rod repeatedly thrusting into my worthless little hole. Every time he bottomed out in me, his large balls slapped against my own tiny sissy balls, reaffirming his dominance over me. My clitty didn’t stop leaking as Master continued his tireless thrusting.

About a month after Master put me in a chastity cage, my clitty no longer tried to get hard. But with the intensity of Master fucking me, I felt the unfamiliar sensation of pressure on my clitty as it tried to grow.

And even though I was locked up and unable to use my useless sissy clitty, I felt more pleasure than I had ever felt when I still called myself a man. I couldn’t imagine ever trying to masturbate with my poor excuse of a penis ever again. All I could want was Master’s hard, thick cock reaming my slutty asshole.

Master changed his grip so that he was grabbing the flesh of my ass. I’d spent so many hours working out my butt so that it would be nice and big for him, and I knew he liked it. In between thrusts, Master spanked my ass until I could feel it turning red.

Our fucking session felt like it went on for hours, and every time Master bottomed out in me, I felt like I was getting closer to orgasm than ever before. My entire body tingled with the excitement and lust that radiated from my nether regions.

Master knew exactly how to get me to the edge. With every thrust, his cock rammed into my prostate, causing me to go crazy. My face was dripping with mascara and cum, and my mouth was hanging wide open, unable to control my moans. My eyes rolled back in my head from the pleasure, and my arms weakened. I was about to fall forward when Master grabbed my hair, pulling me up. With his other hand, he grabbed my own hands and held them behind my back.

I was completely at Master’s mercy. He was fucking my sissy hole relentlessly as I was about to pass out from the pleasure.

Suddenly, my clitty twitched inside its cage. I felt a feeling that I hadn’t felt in a year. A shocking sensation came from my little balls. I started panting as Master continued to drill my hole.

Suddenly, with one final thrust, deeper than I ever felt before, Master buried his cock inside my battered sissy hole. My clitty twitched, and then I shot a thin string of my sissy juice, followed by another, and another, and another, until it just turned into a slow and continuous leak from my locked up clitty. The sensation that I felt from my caged, hands-free orgasm came in waves of pleasure, crashing against my tiny and exhausted sissy body.

My own orgasm, which caused my asshole to clench tightly around Master’s cock, caused him to cum as well. With a deep groan, he filled my sissy hole with another huge, potent load of his seed.

I felt like my muscles were completely locked. I stayed in that same position, panting and moaning like a bitch. My own juices dripped from the tip of my clitty down along my crack, where it mixed with Master’s cum, which was dripping out of my used hole.

Master’s cock slowly shrunk out of my hole with a pop, followed by a gush of his cum.

After I had received the orgasm which I had been denied for an entire year, I couldn’t move. I was in ecstasy.

When I came down from the high of my orgasm, I realized for the first time the true reason why Master never let me cum. I felt a clarity which I hadn’t felt for a year. Now that I wasn’t horny, I felt a small tinge of regret.

How had I become such a dumb, slutty sissy? I let this man take over my life and turn me into a woman!

After an entire year dedicated to only serving my Master, I felt a little bit of my old masculinity coming back to me.

Then, Master spoke. “Ella, happy anniversary. You’re such a good sissy girl. Master loves you very much.”

His deep, soothing voice was all it took to complete shatter the tiny fragment of masculinity I had left. I involuntarily started sniffling, before then breaking out into a full sob.

“What’s wrong, Ella?” Master asked.

“N-nothing, Master,” I spoke between sobs. “I-I love y-you so much! Thank you, Master!”

I didn’t know what to say besides that. I turned around, and wrapped my arms around him. I was wary not to make a mess of the cum that was now all over me.

Master chuckled and returned the hug. “You’re welcome, Ella. I’m glad that you’re happy.”


After that, we showered together, where Master couldn’t help but fuck me a few more times. As usual, he brought me close enough to an orgasm that I was mindlessly horny. But I didn’t care. I loved what he was doing to me.

My only goal is to pleasure Master and make him cum.

Our anniversary night only marks the beginning of our beautiful relationship and my journey to be a true sissy.


From the Author:

Hello, thank you for reading my story! I wanted to just write a short, one-part story here, but if you would like more stories about Ella and her Master, please let me know! Also, let me know if you have any feedback or if you just want to talk at:

[email protected]

Thanks for reading!

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