College Chronicles Ep. 06

I was having more sex than I could have imagined before, with an absolute dream girl. It was humiliating, and sometimes too rough for my comfort... yet, it was also amazing, and a small part of me enjoyed the degradations Cindy convinced me to go through. Even worse, a tiny part of me, hidden deep, deep down, wondered when her cock would make another appearance... maybe even hoped it would, just a little bit.

But far more humiliating than her paying for dinner, or fucking me like a bitch, was the make-up. Each night, no matter what we did, or how Cindy played with me, we always ended up in front of a mirror. Cindy had been intrigued by the sight of me in lipstick and a dress, and I caught on quickly that she wanted to push my boundaries further. At first it was trying a few different shades of lipsticks or modelling a couple of dresses she had already picked out. As time went on Cindy's desires and plans got more complicated. We would spend hours in front of the mirror, Cindy fussing and clucking over me as she applied foundations, bronzers, mascaras, blush, eyeshadow and more. I was often the beneficiary of gifts she received from companies as she tested out new products and styles on me. She would hover around my head, drawing on me with all manner of brushes, pencils, and pens, explaining each product and her strategy as she applied them. Though I was usually high as a kite, I slowly began to pick up on the tips and tricks she taught me. Soon I could apply my own rudimentary version of most of the products.

The first time she had me fully done up, I was floored by my reflection. I've said before, I always had a little bit of pride in my physical appearance, my symmetrical face, my bone structure, and big brown eyes. But made up as a girl, I was downright gorgeous. My skin looked flawless and smooth, and Cindy had perfectly contoured to accentuate my cheek bones and slim jaw, as well as added a slight blush to my pale white cheeks. My eyes lashes were long and fluttered daintily as I blinked in surprise at my own face. They were highlighted by subtle bluish eyeshadow and not so subtle eye-liner that set off my big brown eyes. The look was pulled together by more nude lipstick and gloss, that made my lips look soft, shiny, and extremely kissable. I was dolled up like a slutty girl ready for a night out in a club, dressed to the 9's in the hopes of being humped by strange men. The slutty girls I watched click down the sidewalk with jealousy and envy. It stirred a strange feeling in me, and when Cindy enthusiastically asked how I liked it, I played it cool and shrugged (after politely thanking her of course). Thankfully, my opinion meant little to her, and so she continued to doll me up, sometimes even using me as a model for products on her social media, but never showing my full face.

Her fashion designs upon me also became more complex as time passed. She escalated from the modest if alluring dress she had first provided to more and more revealing dresses with large holes in the front or back, tiny crop-tops that would bare lots of my skin, and short skirts that would leave my little penis peeking out if you looked from the right angle. She began "training" me on how to walk in high heels. Starting me out in her smallest pair, she had taken my hands and walked backwards as I tottered after her. Eventually she would make me stay in heels while hanging out with her, forcing me to practice walking in them. I was far from graceful, and even after a few weeks of practice I walked more like a baby horse than anything.

I had objected to every one of these slights and indignities, in my own way. Cindy's spankings had taught me well that "no" was not in my vocabulary, so my complaints were more whined questions than statements of discomfort.

"Cin... are you sure... my lashes... should they be this long?"

"Are these heels supposed to be... So tall? They hurt to walk in!"

"Babe... this skirt... It's... so short? Isn't it... a bit... slutty?"

But she had a way of making me feel foolish and weak for stammering and stuttering in defence of my masculinity. All my complaints were dismissed easily by her matter of fact, no-nonsense tone, and if I refused to let the issue drop, I was punished with stinging spankings that would bring me to tears. It didn't take me long to learn to keep these problems to myself.

Even more humiliating than women's clothing and makeup, though, were the 'lessons' Cindy began teaching me. It could happen in public or in private; Cindy would say, do, or see something that would reminder of how a girl should act, and then insist on "teaching" me how to imitate it. It started simply, with her showing me how to shave my legs, body, armpits, and pubes, which was easy since I didn't have much hair to begin with. Then she jokingly showed me how to "walk girly" after she had me put on one of her outfits and pairs of heels. The hungry, devious look she had given me as I uncertainly sashayed around her room trying to sway my hips unnerved me deeply.

She didn't stop at how to walk. Cindy gave me tips and advice on all the things girls used to drive boys wild. She made me practice biting my bottom lip and making (in her words) "fuck me eyes." She showed me how to lay my hand lightly, delicately on an arm or chest just long enough to feel more than accidental, and how to bend down to reveal my heart-shaped ass in the best possible presentation. She taught me how to dance like she did, shimmying and gyrating and making the most out of the revealing clothing she wore. She went even further than that, lavishing me with products to keep my skin and hair soft and shiny, along with advice on how to use them. She took me to a salon and had my nails done on my feet and hands. She gave me crash courses in perfumes and fragrances and helped me settle on my favorite scents. She continuously reminded me to be girly—she insisted I speak in a higher pitched, more up-talky version of my normal voice, and avoid using more masculine sounding words like "dude" and "bro." This was easy, since my voice had never been low-pitched to start.

I didn't like most of the things she taught me, and I certainly wasn't interested in making 'fuck-me eyes' or 'driving boys wild'. But Cindy was a strong believer in pop quizzes, and her punishments for failure left my ass sore for hours, so I paid attention and tried my best to make her happy. And some of the lessons were pleasant. Since beginning to use her products, take her pills and advice, and shave, my body and hair felt different somehow. My skin was softer, my hair more lustrous, my complexion clearer. I felt like I was moving differently, with a grace and flow that I'd never been able to fall into before. I'd feel my ass, becoming sculpted and toned, and figure that it was because of Cindy's workout regime. I should have had a clue then; working out doesn't make you more hairless, doesn't change your skin, doesn't make you favor a higher voice... but maybe I didn't want to see it.

One weekend, Cindy said we were taking a "field trip" and took me to a local mall. I was confused when we approached one of the kiosks, but that confusion changed to fear and embarrassment when I realised it why we were there—I was getting my ears pierced in the mall, like a dumb teenager getting ready for her first party. I tried to complain to Cindy,

"But... Cin... Wha... I won't... I can't..." my voice cracked as I tried to protest, making my feeble complaints more pathetic. Cindy turned to me and explained,

"Awww, Sami... Look, lots of guys are getting their ears pierced now. Plus, I've already got a couple pairs of earrings ready for you at home. Don't worry, it won't hurt much, I promise!"

Her light, upbeat tone made me think there was a chance I could push back.

"But Cin...I don't want—"

Suddenly she was in my face, holding one of my arms tight. The gems of her eyes flashed with concealed anger as she nearly whispered through clenched teeth,

"Sami... You know I don't want to hear no... Do you really want me to have to punish you again? Here? Now?"

Thankful to break contact with her withering stare, I looked around the mall. It was a weekend, and the concourse was bustling; families dragging children behind them, groups of high school teens staring at their phones or gossiping loudly, octogenarian mall-walkers speeding in circles around each level. The mention of punishment had reminded me of the last spanking, evidence of which I could still feel in the soreness of my ass cheeks. Surely, she couldn't punish me like that in front of all these crowds? Her hand tightened around my arm, reminding me of the grip she had on me, literal and metaphorical. I looked back at her, and her flaming green eyes burned through me. Gulping down my anxiety, I quickly shook my head.

"Of course not! Let's go, silly!" The fire in her eyes receded to a playful glimmer, and she turned to thread an arm through mine and pull me along. She took total charge of the interaction, telling them what she wanted, and sat with me and held my hand while they punched holes in my lobes. When they were done, she wiped and lifted my hands to my ears, then produced tiny, diamond studs. She took care of me, and before I knew it, I had two new fashion accessories and we were leaving.

Later that day, Cindy dragged me to a hair salon. Cindy insisted that I grow my hair out long, and it felt like my hair had followed her command, was growing faster and with a wavy appearance and silky feel. I had a short bob at that point, and Cindy had the hairdresser give me small bangs and trim the sides into an alluring diagonal that crossed against and emphasised my cheek bones. Then she REALLY surprised me.

As the hairdresser was sweeping up the small clippings of my hair and I was checking my new look in the mirror in front of me, Cindy casually mentioned that she also wanted my hair blonde, almost flippantly, as if it was as obvious as "the sky is blue". I was aghast, my mouth wide open looking at her via the mirror. She had never mentioned anything this drastic to me! But another withering glare silenced me, daring me to even think of objecting to her decision out loud. When she mimicked a mouth closing with her hand, I picked my jaw off the floor and sat, staring at myself in the mirror, thinking about how I would look fully blonde, and considering what this would mean for me. Luckily, the process wasn't too long or painful, and soon I was staring at an unfamiliar version of myself with a cute, bouncy bob of bleach blonde hair framing my increasingly feminine appearing face. Despite my unease with the whole situation, I had to admit I looked good as a blonde, and Cindy's obvious pleasure at my transformation lifted my spirits as well.

With all of this going on, by the beginning of October, I was thoroughly confused. I spent my days as normal as a college student could be, going to classes, getting coffee, and playing video games. By night, I was having often painful, demeaning sex, and spending most of my time presenting as a woman. Cindy had suggested I separate the two identities, and she already had a name in mind... so that had been the true birth of Sami. But I overestimated myself, and the two lives quickly became difficult to keep separate. I sometimes found myself slipping into the mannerisms of Sami, which was troubling until the next time I saw Cindy, and my concerns were washed away by her compliments.

I was able to conceal most of the changes from Natalie. I don't think she noticed the transformations in my skin or my body—why would she even have been paying attention? The hair and earrings were a stretch, but she seemed to accept my awkward excuse about "wanting to make a change." She must have noticed some of the other more obvious differences; my new scents, the changes in my voice and behaviour—but if she did, she kept her thoughts to herself. In fact, our friendship grew as we commiserated about classes, pop culture, and Jaxx, and I had come to consider her one of my closet friends. While Cindy made me feel at peace behaving as a girl, being with Natalie made me totally unconcerned about gender and comfort, able to truly be myself. Maybe it was another clue that "my true self" with Natalie was incorporating more and more of the lessons I had been taught by Cindy...

Then one day, things changed.

As I said, it was the beginning of October, and at our college that meant changing leaves, cold weather, and pumpkin spice everything. All the students were settling into the routines of classes and work, and the parties from the beginning of the year had slowed to a smattering on weekends. It was around dinner time, but I was in 001, alone (thankfully) and slouched over my desk, banging my head against the brick wall of coding work with an impending deadline. I had been struggling to keep up with the combined demands of my relationship with Cindy and the responsibilities of classes and homework, so I was feeling a little down. I had been accepted to this school too, how did everyone else seem to be so much more secure in their work than I was? Was anyone else sitting in their room working frustrated as I was?

With this on my mind, I was grateful for the dinging of my phone to distract me. It was Cindy, and my heart jumped, beating a little quicker when I saw her name on the screen.

Hey slut. Dinner? B at mine in 15. 😘

Cindy's text made me smile, even though I had seen many like it. At first, I had cringed at the often insulting texts, which were uniformly dismissive of any opinions or feelings I had on her decisions. I had read her intent as cruel, a promise of pain and punishment. But now I knew Cindy better, I could hear the words in her frolicking voice, understand her playful sarcasm. Slut was just another endeared nickname for me, and I preferred it the dreaded "Pussy" she would spit at me when she really wanted to make a point. I responded immediately.

Yes please Cindy! Thanks! ❤️

I had learned my lessons well.

I dressed in a flurry. The first touch was a pair of panties; I wore black boy shorts decorated with a bit of a frill that hugged the curves of my butt and squeezed my small package. Cindy had bought me new skinny jeans that emphasised my ass, and a range of more stylish expensive shirts that fit more tightly than my old ones. I riffled through my now extensive wardrobe, eventually settling on black skinny jeans that I knew Cindy liked and a yellow button-down over a simple white-t. Over top I pulled a baby-blue fleece, also courtesy of Cindy, and one of her favorites. I told myself I was choosing these clothes because it would help avoid any punishment, but in truth it also provoked a warmth in anticipation of the smile and compliments I hoped to receive when she saw me.

Stopping to check myself out in the mirror, I was appreciative of my choices. My blond bob and bangs framing my face, no makeup but skin clear and pale complexion making my large brown eyes stand out. You could barely see the glint of the twin diamonds in my ears—Cindy left the more complicated earrings for Sami. My hair stood out against the vivid blue of the fleece, and a hint of my sunny yellow shirt was visible at my neck. I would never have worn these sorts of bright colors before meeting Cindy, but now I was beginning to cherish the shades and textures she had introduced to my closet.

I walked at a brisk pace to stay warm, as well as make Cindy's deadline. That wasn't an idle choice—she didn't like to be kept waiting. But I had lots of experience, and made it with time to spare, standing on the curb outside of her house waiting for her appearance.

When she did, I was stunned by her looks, even though I had seen her many times before. Her rusty hair was the same brilliant hue as the leaves in the trees, and her brilliant green eyes burned against all of it, twin torches against the freezing weather. She was dressed in a tight, red and yellow splotched dress with straps over a white long-sleeve turtleneck, both of which emphasised her attractive, fit body. For warmth, as if she needed it, she wore a very sleek black leather jacket with a large pure white fluffy hood and a very cozy-looking woolly interior.

She had on her signature vulpine smile as she approached, stoking the warmth in my gut, the sense of pride and shameful narcissism that she loved to throw fuel on.

"Oh my god Sami! Looking HAWT! Spin for me!"

I sheepishly spun, and when I had turned I was face to face with her. She leaned in to kiss me and forced her tongue into my mouth, ravishing me in broad daylight. The force of her kiss swept me off my feet, and I crumpled in her arms. When she pulled away and righted me on my feet, my knees were weak, and I gazed dreamily at her, in a bit of a daze. She giggled at my expression and linked her arm through mine, pulling me down the road.

"Come on! We've got a reservation at a place I KNOW you'll love!"

Fewer people watched us as we walked across campus now than had at the beginning of the year. I attributed it to people getting used to seeing Cindy, as well as the cold—fewer people outside, too much attention spent on staying warm. But in hindsight, it was perhaps also because of the changes that Cindy had made in me. We were less of a mismatched pair now, two slim, athletic figures dressed in brightly colored, trendy clothes. We still got a few glances when we happened to pass close to groups of people, and I could have sworn I received just as many glances as Cindy, but I reasoned I must still be dizzied by her kiss.

When we reached a main road, Cindy pulled out her phone and ordered a car through an app. When it arrived we hustled in and clung together for each other's warmth, holding hands and sitting next to each other in the middle of the seat. We rode into the city, giggling and chatting. I tried to pay as little attention to the driver as possible; he was older and badly kept and shaved, and his gut stuck out from below the edge of his frazzled shirt. When we got in, I caught him giving us a look that made me feel nervous. I kept catching him looking back at us in the rear-view mirror, checking out Cindy a bit lewdly, I thought. One time I looked in the mirror to find him staring at me. His wrinkled face split into a lecherous gap-toothed smile, and he winked slyly at me. I did my best not to look at the mirror or him after that.

We arrived at a small hole-in-the-wall Italian restaurant where there was already a table for two reserved in the very back. Cindy knew me well—I did love the place. It was quaint, with exposed brick and an atmosphere and serene and positive vibes. The food smelled good, and tasted better, and while the servings were fancy and small, I didn't mind; Cindy had been encouraging me to be more aware of what I was putting in my body, anyway. We sat and talked until I lost track of time, sipping wine, and nibbling at our dishes. I think that really was when Cindy finally had me fully wrapped around her finger. The cruelty and the humiliation and the denial were one thing, as much as they titillated and aroused me. But the true way Cindy had taken control of me was through her kindnesses, her nurturing, accepting behaviour, and the ways she spoke to me when we were alone. This date; getting drunk together and having our own little space, at a place that Cindy had known I would like, really struck home. She HAD to care about me. To do all this if she didn't, it would be insane.

This realisation made me feel giggly and warm, though that also could have been the alcohol we were drinking. Either way, our date's end snuck up on me, and I was a little disappointed when Cindy told me to get our coats and wait for her outside. I dutifully waited, first for Cindy to pay, then for the car she ordered to arrive. She had them stop at a gas station, and we picked up some more wine for the evening, Cindy inundating another unprepared cashier with flirtatious looks to distract from our under-aged purchase.