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.
