Boy to Bitch and Beyond Ch. 01

This series of short stories will be a mix of real life events that I have experienced and fantasies I wish to experience. The names of the people are changed and exact details will differ from actual events.

This is an adult story. You must be 18-years-old to read it.

Chapter One Summary:

My senior year of high school, a new girl started at our school. I tried to be polite which to her meant I wanted to be with her. But being with her wasn't a normal relationship. She began to mold me into her submissive and opened my eyes to a whole new world before leaving me a month into the year. This left me craving more even though I started a normal relationship with a girl I had a crush on for a while

Chapter one The New Girl:

You ever wake up in the morning and just know the day is going to be a good day? Like no matter what negative thing comes your way you still feel as if today is just going to end as a good day. Those are the days I know I am getting fucked by someone. No matter what happens I know it is going to be a good day, 'cause I get to be the real me—a dirty little sissy slut.

I should probably introduce myself first. My name is Joey Jacobs. Sorry, my name was Joey Jacobs. My new name is Jessica Jacobs (not officially, though) and I am here to tell you the story of how I went from being a normal teen to being a sissy slut.

It all started when I was 18. Well, I guess I would be lying if I said it all started when I was 18. I lost my virginity at 13 years old and had been sexually active since then. I was for a long time one of those guys that talked to every girl in school and hooked up with a decent amount of them. My birthday was in August so I was one of the older kids in my grade; very few were the same age at the start of the year. A lot of girls always told me they thought I was more attractive cause I was a little bit older. The point I am trying to make is I wasn't really new to sex but when I turned 18 my world got flipped upside down.

My birthday fell only a few days before school started back up. It was my senior year of High school. I woke up for school the first day and I woke having one of those feelings like it was going to be a good day. I did not like school by any means. I was a solid B student. But I'm a social butterfly, and during the summer I usually only see the same people I am closer with, so it's always good to go back and see some of my other classmates.

When I walked in the front doors of the high school, I headed downstairs to the senior lounge. The seniors at our high school got a good amount of benefits for being a senior, one of which was the senior lounge. It was right off of the cafeteria so we could eat lunch in there or use it for study hall. Before the bell rings though, a lot of the seniors hang out in there. It had three vending machines, including a pop machine. It had a pool table and a ping pong table. The best part was no hall monitors like in the normal study hall and cafeteria. They sat outside and checked your ID to make sure you were a senior. Other than that, they didn't really do anything.

I took a seat at one of the couches they had in the lounge because I was not a morning person and wanted to rest my eyes before first period. I wasn't there long before one of my good friends Christopher showed up. He came over to me and started nudging me. "Hey Jacobs, wake up!" When I opened my eyes and looked over at Chris my eyes immediately looked past him. Behind him, walking into the lounge was a new girl I had never seen before.

She was cute; not hot, but cute. She was probably 5 foot 5 inches tall, compared to myself at 6 feet tall. She was skinny with nice curves. She had long bleach-blond hair. She was wearing a tight-fitting, not-too-revealing, shirt with a light black Nike sports jacket and jean shorts that were probably not long enough for dress code but no one ever cared. The first thing my eyes ran to though, was her boobs. They were easily D-cup and I knew she wasn't wearing a push up bra because you can faintly see nipple piercings through her shirt. She was a cute-looking girl. But there was something about her. She walked with a sense of confidence that you don't see from many people at that age. It was almost intimidating to even approach her, which is probably why no one did. She took a seat at one of the tables not too far from where I was sitting.

Like I mentioned before, I was sort of a social butterfly. I talked with Chris for a little before telling him I wanted to go introduce myself to the new girl because no one had talked to her yet. He didn't even realize she was there. I headed over to the table she was sitting at and sat down. She looked up at me and I said Hello. I didn't know it at the time but that hello kind of changed my whole life. She smiled at me and said, "Hi, I'm Zoey. I transferred from one of the Catholic schools in the city." I never even asked her what her name was and she just offered it up. I was thinking to myself, though, 'Catholic school girl. She must not really be looking for anything sexual.' But then I remembered that Catholic kids in my area were sluttier and more experienced than public school kids. "Hi, I'm Joey Jacobs, but everyone calls me Jacobs," I responded. We continued to talk for a little and during the conversation something just seemed off. She didn't just act confident; it was everything. She seemed to be just a really confident person but something else was off. The conversation wasn't a normal high school conversation; it carried itself differently. I am not sure if it was just me but looking back at most conversations in high school, they always seemed to be centered around three same few things, childish things. But when I talked to her it was intellectual, like she was analyzing me. It kind of creeped me out, to be honest. She seemed to really be into the conversation and I wasn't a rude person, so I let the conversation go until the first bell rang to go to class. I told her it was nice talking to her and that I was sure I would see her around school.

We had a good-size high school and they usually put the same kids in classes together, not really sure why. I didn't really expect to see her in any of my classes and she already told me her lunch period which was not the same. So, I went about my day going to the first three periods. Environmental science was first. At my high school, you really had two routes when it came to most subjects in school. The smart kid route or the not-so-smart kid route. The smart kid route ended with physics our senior year and the not-so-smart kid route ended in environmental science. But the good news is that I ended up getting my first A+ in this class at the end of the year.

Second period was English 4 and like all other English classes it was boring and a waste of time. Third period was my math period which like science I was in the no-so-smart kids' class of Geometry 2, vs. being in Calculus. I am actually glad at this point I am in these classes because that means it's an easy senior year. Fourth period is my study hall period. I made sure to make it fourth period because my lunch period was fifth. This means I could be first in line. By my senior year I developed what I think is a perfect schedule. Get your hard classes out of the way early take a study hall to get any homework done and then immediately go to lunch so you are first in line. The rest of the day is filled with classes that don't give homework so you're free to do whatever after school. It really was a foolproof schedule.

With it being the first day I did not have any homework to do in study hall. I was the type of person that can get comfy and take a nap anywhere. So, I got comfy in the senior lounge and started taking a nap. That was until Zoey sat down next to me. I didn't even know until I got a hand on my leg—rather high up on my leg. I woke up to her staring at me.

"Hey, Joey, looks like we got study hall together," she said. She was acting like we had known each other for a long time. At first, I thought she put her hand on my leg just to wake me up but she never removed her hand, only moved it up and down my leg. We talked for a little bit. I really just wanted to take a nap this period because I was up late the night before. It was the first day back to school and I was still on summer time.

I wouldn't even really say we talked; it was more her talking to me. I really wasn't sure why she was so overwhelming with me. I saw her in the hall one time when she met other people. She just seemed to cling to me, but not like a lost puppy. She clung to me like a tapeworm needing a host. Her conversations got more and more personal. I just sat there looking at her blue eyes and her plump, smooth lips with a pinkish lipstick on. I could see the hunger in her eyes like I was prey. I was nervous like she was just buttering me up getting ready to pounce.

She began to move her hand, but this time she was feeling my cock through my shorts and boxers. She started asking me if I thought she was pretty and if I was attracted to her. My mind was already mostly Jell-o. I had the fight to find the words to respond.

"Yes, you are very cute, and I am attracted to you," I said. It was a simple response. She moved her hand to under my shorts now.

"How attracted are you to me?" she asked. The blood rushed to my cock, it felt like it left my head without any blood in it.

"I mean you are really attractive but I hardly know you," I proclaimed. I immediately got up and left the senior lounge to go to the bathroom, trying to hide my boner. When I got into the bathroom, I splashed some water on my face. My mind had gone blank for a few minutes; I wasn't sure what was going on. I was attracted to Zoey but it was different. She asked me these questions, not as if my response mattered, but to show me she was above me. She'd never even said she found me attractive. She was just a predator hunting its prey.

I must have spaced out for a few minutes because next thing I know Zoey was standing in the bathroom behind me. She approached me grabbing my cock firmly and just said, "Let it happen." At this point I kind of just said fuck it. If this is what she wants, who am I to stop her? She kissed my lips, biting my lower lip as she pulled away. She pulled my shorts slightly down as she went in for another kiss; her lips were like softened butter. Next, she pulled my boxers slightly down, as my 7-inch cock popped out. She now had her silky-smooth hands rubbing my cock. She massaged the head of my cock with her thumb and index finger before stroking me a few more times. Then she reached down, grasping my balls, before going in for another deep kiss. As our lips touched again, she pushed her tongue into my mouth. At the same time, she gave my balls a hard squeeze like she was testing to see if a lemon was ripe. I gave a small wince but her tongue was already swirling inside my mouth. Like she is showing me what she is going to do to my cock. Just as quickly as her tongue entered my mouth, she pulled it out. She dropped to her knees, kissing the tip of my cock just as passionately as she did my lips. She slid her tongue all the way down to my balls before taking the right ball into her mouth, swirling it around before taking the other inside. She then let my wet balls fall back towards my body as her tongue slid back up the shaft. My mind had gone completely blank, forgetting I was in the high school bathroom and anyone could walk in at any time.

She took the tip of my cock into her mouth swirling her tongue around. All while massaging my balls with her left hand. She slowly went deeper and deeper, picking up the pace as she went. She seemed like a pro and it felt like nothing I had experienced before. Before I knew it, my cock was at the back of her throat, with spit dripping down my balls. The whole time it felt like she was in charge; this new, innocent, Catholic school girl sucking my cock like she was a porn star trying to win a million dollars. She grabbed my ass and used it as leverage to face fuck herself. It only took a few seconds of this before I felt myself getting ready to cum. She kept going and just as I began to pulse, about to burst, she pulled off in one quick motion. My brain was blank and the ecstasy from almost cumming made everything blurry. I thought she would grab my cock and finish me off, but no.

As I came down from the high, Zoey was already back on her feet standing at the sink washing her face and hands. She looked back at me and said, "Good boys only get to cum after I get cum. You may want to pull your pants back up; the period is almost over." Time had flown by and no one had even come into the bathroom. I pulled my pants and boxers over my cock, which was still wet from her mouth. She started reapplying her lipstick just as the bell rang announcing fourth period was over. Before I walked out of the bathroom, Zoey turned to me and said, "You need to shave down there; ladies like it clean." I just nodded in agreement before going to get in line for lunch.

I went into the lunch line, still coming down from what just happened. A couple of my friends got into line right after. It was Luke and Tony; we had all been hanging out all summer. Tony looked at me and asked who I had been making out with this early in the year. I was questioning how they knew about what just happened. Tony was the football player of the group. He has also been in a "serious relationship" with a volleyball player named Amber.

"How do you know I was making out with someone?" I asked.

"I can see it in your eyes; also you have lip stick all over your lips," Tony said. Luke was the shyest one of all of and had only really ever been with one girl named Holly. They have been on and off for a little while. Holly was the type of girl that was kind of a pain to be in a relationship with, because she got too emotional too quick. I had dated her back when I was sophomore, when Luke was on a break with her. I always called them his mental health break ups. During the time we were dating, Luke refused to talk to me so he didn't talk to me for like two weeks. He said it wasn't cool to date Holly even though they weren't together. I tried to tell him it wasn't my idea but it all worked out in the end. But the funny thing was that Holly wore the same lipstick color as Zoey did, today. At the moment Luke was dating Holly. So, let's just say Luke thought I was making out with his girl.

So, not long after the best head of my life that didn't even end in my cumming, I was now faced with a situation to tell them the truth of who I was with. Which seems like an easy option, but something was eating at me. The way Zoey acted, the dominance in her character, and the way she talked to me. Like she was better than me. I wasn't sure if I really wanted to say it was Zoey and then it turned out she was some crazy nutjob. Or I could tell Luke it was Holly and I thought they weren't together. I opted to not get into it with Luke because he might be shy but he was big—like, real big. For a guy in high school, he was pretty jacked up, but yet didn't play any sports. So, I told them it was the new girl Zoey. They asked me a lot of questions but I only told them we made out in the senior lounge and that was it.

Tony, even though being a football player, was also in a lot of the smart kids' classes. He started telling me that Zoey seemed kind of weird for a smart kid. I didn't even know she was in those classes. He was telling me that she was 19 years old, and that she got expelled from her old school before she could finish her senior year due to trying to seduce a male teacher. I asked him where he heard this rumor from. But according to him, she was pretty open and she was telling some of the girls in the class that her grades started to slip so she asked a male teacher for the extra credit. The male teacher refused but she insisted she would do anything. The male teacher filed for Zoey to be removed from the class but the school had a strict policy and ended up expelling her. She was held back a grade and would need to retake her senior year in public school. He also told me that she was a vegan and ate fish food, aka seaweed chips.

After hearing that whole story, we finally sat down with our lunches. They always took forever on the first day because they didn't anticipate this many kids wanted hot lunches as the school always stated. I went to the same bathroom that everything happened and wiped off my face. Just like the lounge it was a senior only bathroom which is probably why no one walked in when it was all going down. I could still see where some of the spit dried on the floor. After I wiped off Zoey's lipstick, I went back to join Luke and Tony before Amber joined us with one of her friends, Sam.

Sam was on the girls' tennis team. She was a petite girl with a light brown hair and cute little dimples. I had a crush on Sam for years but every time I would ask her out she would say no. I was too much of a player and she was looking for something serious like Amber has. I really wanted to make it my goal to be with Sam. She was super smart, pretty, and down to earth person. I spent all summer single, and just talked with Sam every day, asking how her day was and how she was doing. I planned on asking her out again soon because I really did like Sam. Which is why this whole Zoey situation threw a wrench in everything. I knew that Tony would tell Amber about Zoey unless he knew it would hurt Sam. Sam was Amber's best friend, so in turn was Tony's best friend. I knew if I wanted to be with Sam that I needed to ask her out on date before Tony said anything.

As the period went on and we finished lunch we always had time at the end to do whatever. Another benefit to being a senior is we had the senior courtyard. We could go outside and hang out; it even had a path through a small garden that one of the clubs set up. I asked Sam if she would want to go for a walk in the court yard. She was wearing this really cute light blue dress with white tennis shoes. It was pretty flowing but complemented her body well. She agreed to walk with me only because I asked nicely. When on our walk through the court yard I asked Sam if she would go on a date with me. Like an actual date not just go to the Friday night football game dates that most high schoolers do. I wanted to take her on an actual date. I thought for sure she was going to say no again. But to my surprise she said yes. She told me that I seemed to have matured and that she would love to go on an actual date with me. We finished our walk but before we got back to the lounge, the bell rang to head to sixth period.

I had class with both Sam and Luke. It was the final boring class left in my day...history. This year's history course was Government. An entire year of learning about different governments and how they run. But the teacher we had was one of the cool teachers who let us pick our seats. I sat next to Luke and behind Sam towards the middle of the room. About half way through the class I get a text on my phone. It was an unknown number, it read, "Hey, it's Zoey. I got your number from Allen. Read this article when you get the chance." I clicked on the link and the title was, "How to eat pussy the right way." I immediately closed out of it and didn't even respond. Another text came in a few minutes later, " I am not saying you don't know what you are doing but if you want to cum next time then you better know how to make me cum." I ignored this text, too.

After class was over, I only had one more period, which was gym. I always liked taking at least one gym class at the end of the day. I did it every year for the whole four years. I took every class they offered and some twice. I found it was a good way to relax at the end of the day. On the plus side my gym teacher usually was my track coach, so if we had a meet in the spring that I need to rest for, he would still give me credit.