Boy to College Girl

Full Novella Description:

Charles has battled against his feminine features all his life. It takes a single experience with a dominant, alpha high school jock in the locker room to make him know his place in the world. After he is gratifyingly used and abused, Charles completely accepts his sissy identity, and begins meeting strange men, having hot and risky experiences, and even taking on his sister's name, Jane.

After seeing the power of femininity, of being a girl, of pleasing men, she attends an all-girls college to learn not just how to dress like a girl, but how to act and talk like one.

But college isn't as dandy as Jane expected it would be. From unsuspecting roommates, spying on other girls, college boys, professors and bad grades, blue-collar contractors near the school, Jane is confronted with a mix of steamy new experiences and a stack of problems! There's only one way a sissy can solve any problem, and you can guess what way that is!

Ella Rose, author of a top-10 HEA transgender romance ‘Boy to Bride’, now brings you another fun and erotic HEA to add to your shelves!

Part 1: Admissions

Chapter 1: Meet Jane

Among the make-up kits and hair brushes scattered all over the top of her dresser, a lamp faced the open space of the bedroom. It set a warm, sensual, and intimate atmosphere in her bedroom where Jane felt safe to be herself. The tone it set was perfect, and it was just past midnight—the perfect time for sissy boy crossdressers to finally be themselves. Jane had wireless earphones plugged in, she was listening to upbeat sissy hypnosis music videos. Her neighbours only knew Jane as a quiet guy who kept to himself, but behind closed doors she lived her own secret life of a school girl sissy—and nobody had a clue!

Jane learned forward towards the mirror to apply her cherry red lipstick. She admired how well she had been getting at applying make-up, all those tutorials online have really helped out. As she pressed the lipstick against her full lips, she recited some golden sissy rules:

There should be no other purpose in life than pleasing the alpha.

There should be no other purpose in life than pleasing the alpha.

There should be no other purpose in life than pleasing the alpha.

She was dressed like a drunk, slutty schoolgirl. The dark forest green colour of her skirt and tie were the exact match for the private school she would be attending. This was no longer just fun for Jane, albeit it was fun, but it was also serious business! Yes—For about half an hour, she practiced walking like a lady, as if she had grown up in a normal upper middle-class nuclear family home. It was important for her to not only master the look of a sissy, but the mind of a girl as well. It didn’t take long for Jane to get turned on after realizing how deceptively well she could fool anyone into believing she was a girl.

Jane’s shirt is unbuttoned down to her stomach, and her matching skin tone silicone breasts were just asking to be squeezed. It looked like real cleavage! They were just asking to be grabbed, squeezed, and man-handled by some dominant alpha. She stepped away from the full-length mirror and assessed herself up and down. This really turned her on! She turned her waist to the side and lifted up her frilly skirt, showing her pale ass. She put a finger to her lips and made a sexy pouting expression, and slapped her ass with her other hand. She let out a girly “Ouu!” and a red hand print quickly began to show on her ass.

She turned to face her pelvis to the front, and lifted up her skirt. She was smooth and hung. She bent her knees, doing the little excitement bouncing action that girls do when they receive gifts from their man. She loved not only how her breasts looked when they bounced, but her flopping, erecting cock. Her sissy clit was desperately asking to be touched, so she teased bottom of the cock head with her soft finger tip; her long, pink fingernails lightly scratching the end of her urethra. “Ooh”, she said in a convincing girly tone. Her cock was throbbing, asking for more. She arched her back and leaned her head backwards in ecstasy, wrapping her hand around the base of her cock.

There was just an indescribable aesthetic of a hung cock attached to a slender, pale, wide-hipped crossdresser. The best part? Her pretty, innocent-looking face. She had an oval-shaped face with a trimmed jawline, big, round hazel green eyes, full lips, and a slightly-upturned nose. But looks can be deceiving, and not one of you, not even myself, would have known that Jane was genetically a boy if we were to see her out on the streets. She was the picturesque definition of a trap.

Chapter 2: Hello, I’m Jane!

Hey guys! My name is Jane Pritchett, and welcome to my world! I’m a first-year student here at Milton College, one of the most prestigious all-girls school in the country! Let me begin by saying that it wasn’t easy to pass as a college girl! Every girl here is so feminine and pretty!

Since I’m talking to you, and I know that you won’t tell anybody, I’ll let you in on a little secret that no other student here knows about me. I’m not really a girl! I was born a boy! But it just goes to show how convincing I can play the part if I’m surrounded by all these alpha women and nobody has figured it out!

So how did I get into Milton College you may ask? I mean, it is an all-girls college after all. Plus, I grew up in a foster home—so you can assume I was broke straight out of high school. Well, it’s a long story. So I guess I’ll begin with... no, that won’t work! How about we start with a little history lesson about me?

My real name is Charles Pritchett. I have a twin named Jane Pritchett. I know, confusing right? Long story short, I took her name when she moved abroad to teach english. I’m 18 as of this past January and right now its September! When we graduated high school, we were given a key to a lockbox at our local bank. All that was in it were old Polaroids of our parents. It was the first time we saw them. They were activists who died for some cause in Asia. We had no other family, aside from far-removed relatives in Europe who did not reply to our emails, letters, and phone calls.

Jane and I were out on the porch, drunk, laughing at how stupid we were to think that we were going to get some large inheritance... That our parents were rich billionaires on an island who were putting us through a test, and the contents of the lockbox would have some treasure map leading us back to them. We still looked at the Polaroids fondly, even though we never saw their faces before, they felt familiar. Mom was really pretty, and dad was a tall, dark, and handsome type. Strangely enough, both Jane and I mostly resembled our mother. Apart from my, well, my you know what... down there, Jane and I were practically indistinguishable growing up aside from her long hair. Oh, and she has blue eyes, while I had green.

Don’t get me started about the changes to our bodies once we hit high school. We both basically had the same slender, wide-hipped body until puberty. Except her figure filled out a bit more, and I only grew a few inches taller. She didn’t grow up as weird as I did. She was popular with the guys, obviously. Me, on the other hand, I got bullied because I never had the genetics for the height and muscles like the other guys did. The other boys got broad shoulders, wide chests, and facial hair. I had narrow shoulders, a slim, underdeveloped torso, and only could grow light baby hairs on my face. I sure got teased and called pansy and sissy a lot because of how twinkish I appeared.

I didn’t know why men were so mean. For almost my entire life I never understood men, until I picked up one of those psychology books by Freud. Once I read that real men were largely motivated by a sex drive, life became a whole like easier for me. I would practice the tricks I learned with random men in grocery stores or in the street. I felt so powerful seeing that I caused the possessed look in their eyes. I really owe this power to my sister, though. Growing up with a twin sister, it wasn’t hard at all to act effeminate. I had years and years of close contact with a feminine girl. Some things that were important were speaking in softer, higher tones. Smiling. Laughing, oh, laughing was very important. Always laugh at a guy’s jokes, even when they’re not funny. Sassy postures to show off your body. And don’t even get me started on finding the perfect, cute outfit! They’re just so many ways to feel girly and sissy-like, and I really hope to share how!

Oh gosh, there I go getting side-tracked talking about how much I love being a sissy boy! Well, this is going to be such a fun story to tell, I’m feeling giddy already, aren’t you? Where was I, again? Oh right! A poor boy at the all-girls college... how did I get here? It begins, like many of these stories do, with high school!
 

Chapter 3: Senior Year with a Jock

When we were growing up, why is it that adults would talk as if they knew every single damn thing? One of the lies that really got to me was that high school was going to be the time of your life. Boy, were they ever wrong. High school was the complete opposite of a good time. I was a 5’5”, a shrimp, nobody cared about me, and I had a girly face. Every guy was smarter, taller, and stronger than I was. I was bullied relentlessly for the first two years of school. I didn’t know until later that a lot of this was because I denied my sissy nature for such a long time! See, I was still known as Charles throughout high school.

I had zero confidence, a total loser! I never had girlfriend or any real friends. The only friends I did have only used me to get with my sister. It felt awful hearing the sounds they made through the bedroom walls. Jeez, I felt totally worthless every minute of every day. To stop the bullying, I eventually learned that staying in the background and keeping quiet would keep me out of trouble. So in my junior year of high school, all I did was go to school, choir practice, and then went straight home.

Then, it was senior year. Something deep within me changed during this year. I started having spontaneous sexual fantasies about my freshman bullies. I think these fantasies started when I began to notice they weren’t the same jerks they were before, but were actually growing up to be men. The popular girls definitely took notice too, they were always surrounding them. Wow, to be one of the alpha guys with cheerleaders wrapped around your arms, doing bench presses at the gym, or having laughs with the boys.

The boring science classes were actually my favourite period of the day! All the jocks were forced to take sciences if they wanted to be on a sports team... part of some school athletic initiative don’t ask me. Anyways, the outcome was that my class was filled with muscular jocks. I’d day dream of tutoring these monkey men after hours, making any excuse I can to get up from my seat to show off my ass and submit like a sissy, and then something would just set them off and they would just throw the books off the table and just have their primal way with me.

Haha, you could say I had a dirty mind. These thoughts stayed as fantasies for a while. I was slow to explore this part of my sexuality. It was my dirty little secret! Not even my twin sister knew. I started watching pornographic videos online of muscular, alpha men really giving it to twinks. I absolutely loved these videos. I loved the story of an alpha, who can get any girl he wants, but instead picks a low-life twink over a hot girl. It was such a turn-on!

I always looked for videos where they would have sex in public, so it always felt like it was from a sudden passion that the alpha pulled the twink into the public bathroom, or behind a tree in a forest during a walk, or behind a bush in the beach for breeding. What turned me on especially was seeing the sissy boy’s clit flopping up and down while the alpha fucked him from behind.

There was one recurring fantasy that was my go-to when I was masturbating. I would remember these two white trash bullies who would always swirly me. They’d always laugh and leave right after. But in my fantasy, they’d be laughing like usual walking towards the door but then the lights would shut off. I’d hear their footsteps against the bathroom tiles coming towards me. I’d then see a blinding light from their phones shining bright on my face. I can see myself a complete mess, drenched from the toilet water, my knees bruised. When I picture what the video looks like, I can see it from the POV of the bully who records the other bully pulling me by the hair and giving me some good, hard slaps. I’d be dazed from the blows and the bright light. Then, the bullies would have their cocks out and take their turn shoving their cock down my submissive throat. Whoever I wasn’t going down on would be cock-slapping my face. They’d cum ropes on my beaten face and flat chest. They’d flash the camera partly away from my face and down at my cock, and realize that I have been furiously jerking myself off to the abuse the entire time. They would laugh at how disgraceful I was and spit on me. They would turn off their phones, laughing, leaving me in the pitch dark. It doesn’t take me long to finish myself off as soon as they leave, and I cum all over my stomach and face.

It’s a shame these kind of things never happen in real life. For a few months, I even tried to provoke the same, old bullies again, but really I’d only get shoved aside. I even tried taunting new bullies, but they just laughed at me and called me a twink. I had to find another way to get a bully to treat me the way I wanted, to treat me like the sissy boy that I am.

* * *

“Hey, how was your meeting with the guidance counsellor?” Jane asked.

Because it was senior year, every student had a mandatory meeting with their guidance counsellor. It was for career planning, or something. I’m not sure, I don’t really listen to adults when they’re speaking. Again, they always talk as if they know more than they really do. I prefer to listen to myself—and the sissy voice within! Things just feel better that way! Even if it does get me into trouble sometimes!

My sister stood two lockers down from me. I hated the fact that the school assigned our locks to be practically right next to one another. She would always ask me questions during lunch breaks and after school that made me feel like such a baby. Things like how are you doing, are you feeling okay, is everything alright? It was all really embarrassing, and I wish she would stop.

“Just the usual stuff, like I need to try harder if I want to get into a good college.” I said, taking my PE clothes from my locker and shoving it into my bag.

“He’s not wrong, you know. You can achieve a lot of things if you make an effort, Charles.”

Before I can reply, someone pushes my shoulder and I spin around and get shoved into the locker.

“Watch where you’re standing, ya pansy!” Connor said. He gave a snarky laugh and he held out his hands. Two of his henchman beside him gave him high fives.

“Connor, why do you got to be so rude to him? He’s a nice guy!” Jane said, trying her best to convince him.

Connor walks up all cocky to her, looks over at me, then back at her. He grabs her ass. God, I wish he would just grab my ass instead. He laughs, “Sorry babe, I can’t control myself sometimes.”

“Connor, stop it!” said Jane, blushing. I knew she liked it. It’s the natural response when an alpha grabs your ass. But she liked to act somewhat like a lady out in public. When he took his hand off her ass, you could tell her mind was occupied on some hot thoughts. Maybe a flashback to a recent fuck session they had, or something of the sort.

“Babe, so I’m picking you up tonight.”

“Oh, I know.” she replies with locked eyes, and they kiss.

“See you my little flower.” Connor said in a sweet voice that made Jane visibly melt, then he glares at me. “You get off on watching your sister kiss, you weirdo?”

I divert my gaze to my shoes. I had these old, red converse shoes on, with holes by the toes. It suddenly occurred to me in a rush that I was a poor, lonesome, outcast. Connor lets out a cocky laugh at my submission, and he walks down the hall with his posse. I look up and see Jane looking almost embarrassed for me. She seems both angry and upset at me. It looks like she wants to say something but she doesn’t. She turns her back on me and walks the other way in a hurry.

* * *

I’ve fantasized about Connor for as long as I could remember. New rumours would spread monthly about him and the prettiest girls in school. You would hear about how some poor freshman fell for his pick-up tricks, how the cheer captain gave him a blowjob behind the bleachers, or how he got two girls to go down on him at the same time.

Everyone tried telling Jane not to go steady with Connor, but she didn’t believe anybody. Not even her BFF. Yet, the rumours stopped as soon as he dated Jane. Well, there was that one rumour from the crazy, goth girl that said Connor forced his way with her late one night in the school parking lot after she stayed until the evening finishing off an art project. But, nobody believed her, and she changed schools only a week after the rumour got around the entire school.

Pretty much everyone had stopped bullying me aside from Connor. Jane would always tell me during breakfast that she was telling him to leave me alone. I mean, if she truly cared, she’d stop sucking his cock which reinforced his asshole behaviour. But she probably got off too hard on the idea of sucking an alpha’s cock. And who could blame her? If anyone had that same opportunity, wouldn’t they jump on it?

As you may have guessed, I have mixed feelings about Connor. I secretly liked it when he bullied me. It made me feel so submissive, weak, and powerless whenever he would demonstrate his dominance. I would easily bend right over for him. It was so difficult to keep my sexual urges repressed around him, he was just so attractive. He was the football captain of our school, blonde, blue-eyed, and muscular. And just today, when he shoved me into the locker, he was wearing a blue polo, and his biceps were really roaring.

His ego was particularly inflated today because it was Monday and it was only yesterday that he carried his team through and won the state championship league. You should have seen the glares he got from the circles of girls by their lockers, the whispers they were making as he walked down as if he were some untouchable god... and in a way, he kind of was. I wasn’t much of a sports fan, but I did go to that game. So I can still see him on the field after the winning goal, being lifted by his teammates and the coaches pouring orange Gatorade from the cooler all over him.  My ears are still ringing from the crowd going berserk! Safe to say, all the girls wanted him and all the guys wanted to be him.

* * *

I hated gym class! I hated that you needed to take a physical education course to graduate this damn high school. Of course I missed the memo... I avoided these classes like the plague all throughout my other years because I knew that the other boys would bully the heck out of me in the locker room. Well, Jane luckily told me about this requirement in one of her usual mothering conversations. Granted, this time it was actually helpful.

At first I was so bummed out that the only course available to seniors was Weightlifting 101. I have no clue why I had this initial reaction of disgust. I thought to myself: “Oh great, going to be stuck with a bunch of doped up meatheads for the entire year.” What an old way of thinking. That was the old pansy-ass kid talking.

“Faggot!” said one of the two jocks passing by me on the track.

I tried to remind myself that I was 18 now, and I only needed to put up with this shit until summer then I would never see these jack-offs again. But, it didn’t work. I felt completely awful after that remark, and couldn’t really dig myself out of feeling blue the rest of the time I was running around track.

“Wrap it up everyone, let’s head inside!” said Mr. Lawson, our gym teacher.

I never could lift very much at the start of the year, and neither could I right now. To be honest, I didn’t really care about the “gains” like how some of the more masculine guys talked about. I would just show up, and that would be it for me. One thing I did enjoy doing were the thigh machines. Practically nobody else used it but me. I didn’t really know why nobody used them, but I always felt a strong pull towards them, like it was just right for me. The machine was put at a corner in the gym, and people avoided that machine, kind of like they avoided me, so I practically had that entire corner to myself. Which, I didn’t mind.

Connor was a real jerk today. He was mocking whoever wasn’t able to do as much weight on him—which was practically everybody... and, he didn’t help out the person he was spotting on the bench! He was letting him struggle, and I seriously think he would have let that guy die if Mr. Lawson hadn’t walked by. Connor seemed super dominating today... Anyways, this is why I liked my little corner. Nobody knew I was there, and I got to fantasize from afar.

Everyone had worked so hard, that by the end of class, everyone was out of breath and their shirts were drenched. They reeked of sweat. As we walked out as a group hurdling through the narrow hallway to descend the steps, I am among the group to be last. Before I put my foot touches the first step heading downstairs, a strong hand grabs me by the wrist.

It was Connor, “You’re not sweating at all Charles,” he said.

“I… wiped it all off.” I said in a smart way, then turned around and kept walking.

“You’re not going anywhere until you break a sweat today.”

I looked to see if others were around, but they had all left already, “Okay, what do you have in mind?”

“Step back into the weight room.”

As I step back into the room, I hear the door shut and a “click” of the lock. The idea of being alone with Connor was making me nervous. I was a bit terrified too. We walked over to an open area and started with some stretches, and when we did lunges, I noticed a substantial bulge in Connor’s shorts. My mind started thinking about the fantasies I'd had about this man, and felt a growing sensation in my own shorts...

"What’s the matter Charles, you okay there?" Connor said with a smirk.

I immediately brought myself out of fantasy mode, and found myself in the middle of the weight room, holding a lunge position. Thankfully my erection had decided to inch itself up the side of my shorts that was opposite from where Connor was standing.

"Oh, I...sure, I'm good," I managed to stammer in response.

"All right then, I was just saying that I think we're well stretched and we can start with the bench press."

I was back to worrying about how the weightlifting would go, especially after I jut witnessed him barely helping out the other guy. But it turned out okay. I could smell his sweat as he spotted me, and for some reason it turned me on. He also showed me the shoulder press, lat pulldown, chest press, and tested me on the chin-up bar. It was a challenging workout, but Connor gave me lots of encouragement, and I ended up being able to lift a lot more than I had figured. Connor announced that I just needed to push through this last set and we would be done. I managed to push through the pain to lift the bar one last time, before my arms dropped in exhaustion. I never knew this side of Connor existed.

"Buddy, that was awesome, you really pushed yourself! How good does that feel?"

I managed to push myself up into a seated position, and was surprised to feel Connor’s meaty hand on my shoulder.

"Pretty...pretty damn good. Yeah." His hand lingered on my shoulder for what seemed like an eternity, but was probably only a few seconds, before pulling it away.

"Alright, lets hit the showers!"

Thoughts ran through my head as I made my way to the locker room, but I convinced myself that Connor was just trying to befriend me. He was dating my sister after all. Maybe he was serious about her, and thought it was only right to befriend his girlfriend’s brother.

When we got into the locker room, Connor left and said, “Oh, I forgot something. I’ll be right back.”

I figured I could quickly shower and dress before he got back. So, I stripped my clothes off and threw them in a locker, before grabbing a towel and hopping in a shower stall. I hated showering, and often waited till all the guys left because they hated showering with the “closet gay dude”. But it had been so long, that everyone else had already showered and gotten dressed.

Something in the corner caught me eye. It was a huge duffel bag that sports team carry to bring their equipment around. Curiosity got the best of me, so I walked over to it, and opened it. Imagine my surprise when there weren’t baseball uniforms, basketballs, or soccer balls. Instead, there were cheer uniforms and pompoms. Budget cuts were terrible, were we now using locker rooms as storage facilities.

When I hopped into the shower area, completely alone, I lathered up my lean body, I found that image of Connor’s package coming back into my head. I started rubbing my ass cheeks, and looked down to see my penis erect at full attention. It stayed like this as I finished washing my hair and rinsing off, and after I turned the water off, I found that I couldn't help it any longer.

I dried myself off quick and look at myself in the full-view gym mirror that the guys would flex their muscles with and check if they had abs. For me, I was examining my smooth, slender body. My legs were like jelly from the work out, but I still had enough energy to stand. I took a cheerleader uniform from the bag and walked back in front of the mirror. As soon as I put it on, my cock protruded through the skirt. I looked like one of the younger girls, because I was flat-chested and skinny and slim, but still very passable. I didn’t realize how feminine my face really looked until I put these clothes on. Were those guys that bullied me expressing their sexual frustration with me with their taunting? When in reality, they just wanted to fuck a pretty boy but couldn’t?

I started stroking myself thinking about this, letting precum ooze out that I could use as lube. I closed my eyes and leaned against mirror, bucking my hips and pretending that Connor was fucking me. "Ooh Connor," I moaned softly.

Just at that moment, I feel a hand wrap around my waist. I open my eyes, and I see that Connor is standing behind me.

"I'd heard some kids talking about you, that you might be gay. I didn’t know they also meant you dressed up as a girl." he said.

For some strange reason, I didn’t feel scared. But I also couldn’t move a muscle. I wasn’t sure what happened to me, it was like sleep paralysis! I couldn’t move any limbs. I was in complete submission. He was in complete control.

"I don’t... but I just saw the uniforms there, and I always thought they looked cute... What are you going to do to me?" I blushed.

"I'm not the cocky asshole I portray myself to be you know,” he slid his hand down to my thigh, and up my skirt to reach my cock, “You’re quite hung for a sissy boy, you know that? That only turns me on more.”

He turned me around and lifted me up. My back was against the wall, and my legs were wrapped around him. We looked into each other's eyes, and became locked in a deep, sensual kiss. My head was buzzing: I was wearing a cheerleader uniform and making out with the star alpha athlete!

The way he was grabbing my waist made me moan uncontrollably.

"You like that, don't you?"

"Uh-huh," was the only response I could muster in my state of ecstasy.

"I've got something that you might like even more."

Connor pulled me further away from the wall and my legs dropped on the ground. He started pulling down his shorts. I took the hint and dropped to my knees. Right in front of my face was the cock I had always dreamed about. I had never done anything with a man before, so I tried to imitate the gay porn movies I had watched over and over on my computer. I started by licking the bottom of his penis from the base to the tip, before taking the entire head in and out of my mouth, with my tongue continuing to lick all around it.

"Mmm, yeah, that's right. Suck that big dick like the little slut sissy you are."

It ran through my head how Connor know immediately what a sissy wanted, much less what a sissy was. I didn't think it was possible, but being called a sissy slut by this total hunk just turned me on more. I tried to take as much of his cock in my mouth as I could, and I could feel my own cock starting to leak as well.

"Let's see how far you can go," Connor said, as he held my head with one hand, and started slowly guiding his cock down my throat. I tried to relax my throat as much as I could, and was able to take maybe half of it before I started to gag and Connor slid out of my mouth. I started coughing.

“Feels good, dirty bitch," he said, ruffling my hair. He started slapping my face with his cock. I started licking all over Connor’s penis again. He really seemed to enjoy it when I licked the bottom of his penis head while simultaneously stroking his shaft. Focusing on this for a few minutes, I suddenly felt his legs tense up, and Connor’s sighs of pleasure got more intense.

"Ooh, ooh, ooh, are you ready for my big load?" he bellowed. I didn't have time to respond before ropes of hot, sticky cum came flying out of his cock in waves, covering my face and chest. I licked my lips and looked up at Connor for the first time since I had started blowing him. We could both barely comprehend what had just happened.

"Uh...wow. I feel much better. Watching those cheerleaders practice earlier today really built up this frustration in me,” Connor began.

I know, I thought. I saw how much of a jerk you were acting to those other guys during training.

“I just fucking love cheerleaders,” he said.

Before he could say another word, I stuck my tongue out and with my other hand I squeezed the last few drops of cum into my mouth rom his softening cock. I stared into his dreamy eyes, feeling so weak and little, but loyal to him. I showed him the remains of cum in my mouth. I moved the salty semen around with my tongue, I loved how the ooziness felt. I swallowed the cum to show the alpha how much of a good sissy boy I was.