Jessie's Sissy Pt. 01

Much of my time in high school was spent fantasizing about Jessie, one of the prettiest girls in school. With her long, straight brown hair draping to the middle of her back. Her slender figure, accentuated by her perfect b-cup breasts and heart-shaped ass. And her unbelievably smooth skin, making her every touch a pleasurable experience.

But back then I had no idea how that felt. I had never so much as spoken to her, let alone been so lucky as to feel her gentle caress. It wasn't very long ago, really. It's only been a few months since she changed my life forever.

It began my senior year of high school. The school year had just started, and I had also recently turned 18. With both these events in mind, I was feeling a new found confidence. I had spent so much of my time daydreaming of Jessie that I decided it was time I make my move.

I spotted her alone at her locker during the passing period, looking stunning as always. She wore tight, white short-shorts which made her perfect ass look all the more desirable. She also wore a semi-see-through black top with the phrase "Stay Weird" printed upside-down across the chest, underneath which I could make out a lacy black bra.

She didn't look in my direction until I was right beside her. A second of silence passed before I spoke, "Hey Jessie, do you wanna go out sometime?" She looked at me for a moment, and then smiled.

"Yeah sure, sounds cool." She said, closing her locker. I tried to hide my excitement, I didn't want to seem desperate. She proceeded to give me her number and we went our separate ways as the bell was about to ring.

Later that night I sent her a text asking when she was free. She replied that she was free now and had a surprise for me, followed by her address and a winky face.

I was so excited that I nearly got in three accidents on the drive to her house. When I arrived she greeted me at the door and led me inside. Jessie seemed incredibly eager about our plans (whatever they were) and practically threw me onto a couch.

"Sit right there." She said in a seductive tone as she strolled out of the room, walking in a more dramatic fashion than usual, which made her hips swing hypnotically from side to side.

When she returned she had two glasses of clear liquid. "What is this?" I asked. She put a delicate finger over my lips. It felt incredible.

"Shhhhh. Just drink. Tonight will be a lot of fun if you just do everything I say, okay?" Her big, gorgeous brown eyes peered right into mine. I slowly shook my head in confirmation. "Good boy, now drink."

When I brought the glass closer to my mouth it was obvious that it was alcohol. I'm not much of a drinker considering that at my age it's illegal, but I wanted to make Jessie happy, so I tipped the cup back and drank it all.

When I finished it off Jessie's smiled widened. "Great. I can't wait!" She exclaimed.

"Wait for wha..." I started to say. And then everything went black.

When I woke up I had a severe headache, I was cold, and I couldn't see. A few moments later it occurred to me that not only was I laying in a very odd position, but I also couldn't move. I was laying on my stomach with my hands and feet draped at my side. Another moment passed and I realized I was naked.

"Oh good you're awake! The anticipation was killing me!" It was Jessie's voice, followed by a laugh. I tried to call out to her but I realized my mouth was being held open by something, making it impossible to do anything more than moan.

"Sorry sweetie, but I need you to be quiet. Just listen to what I have to say and I'm sure it'll answer all your questions." I was very confused by what she said.

"Right now you are blinded folded and tied to a bench in the school locker room. You'll notice I've secured your arms, legs, wrists, ankles, and mid-section to keep you from squirming." This only confused me more, why would I be squirming? And why am I at school? I wanted to vocalize these thoughts but I couldn't.

"I'm sure you also realize that you're naked. That's because we're going to have some fun. But before we do, I have to explain something to you." Her tone was becoming more and more serious, I was getting worried.

"From now on you belong to me. I own your body and your mind. You will do anything and everything I say or you will be punished. You will do only what I tell you and nothing more. As of today you are my slave." What the fuck was she talking about?

"As my slave you will live for my pleasure and amusement. More specifically you are going to be my slutty sissy slave. I'm going to turn you into a girl and make you take things in your mouth and in your ass solely for my enjoyment." She laughed as she finished that sentence.

I pulled against my restraints, I had to get the hell out of here! "Now for the fun part!" She giggled.

"As I told you earlier we're in the locker room at school, The boy's locker room to be specific. And you're probably wondering why." I hadn't thought about that. I was still trying to process the reality of my situation.

"It seems the most appropriate place for what I have planned. As your first act of becoming a girly sissy, you need to learn to love cocks and cum, because that will be your life from now on."

"What? But I'm not gay!" I tried to shout. But all that came out was an odd gurgle. This made Jessie laugh some more. Then she continued with her speech.

"And I feel that the best way to make you love cock is to give you a whole bunch at once. So I got all the guys from the football team and they're going to fuck you! And as part of every training session, you have to swallow every single drop of cum, whether it's theirs or yours, you'll swallow it!" Jessie's tone was getting increasingly excited as she said this.

I tried to shout and pull at whatever was binding me to the bench but it was no good. I was horrified at what was about to happen.

"I don't care if their cum is leaking out of your freshly fucked asshole, you'll lick up every drop with a smile on your face! Got it bitch?" And with that she yanked off the blindfold.

For a moment I was blinded by the sudden light, but when my vision returned I was filled with terror. Standing before me was the entire football team, 30 guys with big, hard cocks.

Not a single one could've been shorter than 9 inches, and they were all pretty wide too. All the guys were slowly stroking their dicks while they looked at me like I was a piece of meat.

"She's all yours guys!" Jessie exclaimed as she slapped me on the ass. They all rushed over and the nightmare began. A cock was immediately stuffed into my mouth, and I gagged from both the pain of having a huge cock slammed down my throat, and the terrible smell.

From both sides I was being slapped in the face by their enormous rods. I could feel droplets of precum hitting me all over. Many of them were taunting me, calling me a "sissy, slut, faggot, cocksucker, bitch-boy," and many other degrading things, but I couldn't focus on what they were saying.

Because behind me a monstrous cock was being forced directly into my virgin asshole with only a small amount of spit as lube. The pain was beyond belief. I tried to scream but was reduced to a painful moan as a dick was still being plunged in and out of my throat.

I could hear Jessie laughing and cheering them on, telling them things like, "Give that little faggot a fucking he'll never forget!" I couldn't understand why she was doing this to me.

I heard her move behind me and say, "Don't be shy, shove two of those fucking monsters in there at once, she'll love that!" And seconds later I felt my anus painfully stretch to accommodate another huge cock.

I couldn't breath from the relentless assault on my throat, his pole was slamming the back of my throat like a jackhammer. I was relieved when he slowed down, but seconds later my situation only worsened as he flooded my throat with hot, gooey jizz.

He began to pull out before he was finished cumming and splattered the remainder of his spunk all over my face. The taste of cum on my tongue was unbearable but there was nothing I could do.

As soon as a cock was pulled out of me, another would promptly take its place. I felt hot cum being deposited into my asshole, and moments later the culprits came around to my face to present me with the filthy rods which had defiled my bum.

As soon as the guy who was currently fucking my mouth dumped his load down my throat, the two guys who had fucked my ass shoved their dirty, gigantic dicks into my mouth.

The taste was horrific, and the smell was even worse. They tag-teamed my mouth with their disgusting cocks until they both blew a load into my mouth.

Cum was dripping from my face and asshole, I could her Jessie laughing over all the shouts of the guys. Suddenly my momentary concentration was broken when the biggest dick yet slammed into my butt.

Luckily there was plenty of cum coating my asshole as lube, but the cock was still far larger than any I had taken yet. I tried to scream and gagged on the enormous meat stick ramming my throat.

The pain in my ass only increased as he drove his snake further into the depths of my bowels. It kept going deeper and deeper and I was sure if it went much farther I would feel it in my throat.

Finally I felt his pelvis against my ass cheeks and was relieved that he couldn't drive the monster any deeper into me. My relief quickly faded when a large hand took a firm, painful grip of my hair.

"Get ready for a real fucking faggot." Said the guy with his dick buried inside me. He pulled the full length of His cock from my ass until his fat head pulled at my anal ring, and he then rammed it all the way back inside my ass in one thrust.

I felt cum erupt from my cock. "What's happening?" I thought to myself. "I can't be enjoying this! I'm straight!" I heard Jessie scream with excitement

."Look guys! The little sissy-boy loves it! I told you she was a natural-born slut!" Jessie squealed.

All 30 guys took turns fucking my face and ass, all the while Jessie encouraged them and gave them suggestions to further increase my pain and humiliation. Some fucked me multiple times. My stomach felt completely fully of cum, and my throat felt like it was being glued shut.

I could feel hot sticky spunk oozing from my full asshole. All the guys stood around me now with their dicks slowly softening. Jessie walked up to me and knelt down so she could be at eye level.

"Wasn't that fun sissy?" I shook my head no, I felt the dry cum on my face as I did this. "Oh yes you did fag. You're little clitty was leaking the whole time." She was right. I didn't want to admit it, but on some level I must have been enjoying it.

"Now you remember the rules don't you? You have to lick up and swallow every last drop of cum here." I had forgotten about that. There was no way I could do it.

She undid the gag in my mouth, freeing my jaw, and then proceeded to untie me from the bench. "There bitch, now get to work." She stared eagerly at me, But I didn't move.

She reached into her purse and brandished a pair of hand-held hedge clippers and waved them in my face. "Lick up all that fucking jizz or you lose your balls!" She didn't seems to be joking.

I slowly lowered my head and stuck out my tongue. I hesitantly edged towards the pile of sperm on the floor. When my tongue made contact Jessie giggled and said, "Good girl. Now speed it up."

I was absolutely disgusted with myself. How could I be doing this? But, despite my mental turmoil, I did as Jessie commanded. I licked up every disgusting drop as they all laughed and cheered me on.

When I finished I looked up at Jessie. She looked amused. "Don't you remember what I said earlier slut? I want you to eat EVERY SINGLE DROP! You've still got cum leaking from your ass, I want to see you swallow it."

She couldn't be serious. I began to voice my objections but she stopped me. "One more word out of you and I put all the pictures from our fun today on Facebook. And I'll be sure to email a copy to your parents and all your teachers." I quickly shut up.

"Don't worry sissy just do as you're told and everything will be fine. I'll even help you." She reached into her purse and pulled out a shot glass. "On your hands and knees." She commanded.

She put the glass up to my sore hole. "Now squeeze out all of your delicious treat for me. Make sure you get every drop, we wouldn't want mommy and daddy knowing their son is a sissy faggot now would we?"

I did as I was told which only made Jessie and the guys laugh more. After a minute or so Jessie declared that I was done. She walked back to my face and held the glass up to my mouth.

"Open wide." She said as sweetly as possible. I reluctantly opened my mouth and she tipped the glass back over my tongue. The cum slowly slid from the glass into my waiting mouth.

When I swallowed Jessie told me I could stand. "Now, before I take you home, I have one last thing for you to do." I couldn't imagine what she could possibly have in store.

"Thank all the guys for their cum. Tell them that you absolutely loved every second of being fucked by them and you are always available to be their little gay cumdumpster." She was overjoyed as she said this.

Thinking of the consequences for disobeying her, I decided I should comply. "Thank you for your cum. I absolutely loved every second of being fucked by you and I'm always available to be your little gay cumdumpster." I said, hating myself for doing it.

Jessie giggled and clapped her hands. "Good slut!That was fantastic. You can go now guys." Jessie waved a dismissive hand and the guys filed out of the locker room.

When Jessie and I were the last people in the room I spoke. "Why did you do this to me?" Despite my best efforts, I started to cry a little. "I thought you were a nice girl, I would've treated you like a queen. But then you humiliate me and degrade me and make me feel like less than a person."

She stared at me for a moment. "Because I wanted to. I decided that I wanted to humiliate you because it's fun. I already told you that I own you now. So shut up."

I couldn't believe what she was saying. "I'm leaving." I said as I turned my back towards her.

"Take another step towards the door and I will fucking castrate you." She said coldly. "A couple of the guys agreed to hang around incase you give me any trouble. They're waiting right outside." I was starting to get scared.

"They can't stick around forever." I said, trying to call her bluff.

"They won't need to after you sign this." She pulled out a few pieces of paper and held it in front of me. "This contract states that you willing agree to submit to my total control, and that I may do anything with you that I please. For all intents and purposes you will be me property. And if you don't sign it... bye bye balls." She smiled at that last part.

She handed me a pen and I stared at the paper. Was she really going to make me sign my life away to her? I started reading it and she was telling the truth. I began shaking with fear.

"Sign the fucking contract or I'll call James and Cody in here and we'll get to work removing your balls." She said, clearly irritated with my hesitance. With a shaking hand I signed my name.

What had I done?