The Greatest Liar Ch. 01: My Awkward Phase

Story Info
Alex Rios' furtive high school transition is exposed.
14.2k words
4.49
9.6k
16

Part 1 of the 2 part series

Updated 06/09/2023
Created 06/26/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter 1 My Awkward Phase

The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar.

Wannabees

I was hanging out with my friends Quinn, Barb and Anne in the Newspaper Office, our refuge at University High in Los Angeles.

A group of scantily clad Britney wannabees passed by, giggling inanely. I affected a haughty gaze but memorized their accessories and gestures. They ignored me, but my friend Quinn noticed my rapture.

"Having a Zen moment over that flock of mindless chicks?"

"Eye candy relieves my boredom."

"Eye candy rots brains like sugar rots teeth."

"Not to worry, they're fake as aspartame.'"

Quinn crumpled a sketch and tossed it over his shoulder.

"Then don't imitate life, get one."

"Life used to imitate art. Now it imitates celebrity, attains meaning only by analogies to tabloid dramas."

"Get off your sugar high, dude. Like Descartes said, 'I think, therefore I am.'"

I rolled my eyes.

"Now he'd say, 'I text, therefore I am'".

Quinn fist-bumped me, and Anne glanced up from her nearly-finished cartoon of a snake devouring a superhero.

"Alex, you put the 'con' into conformity."

Barb was on a computer, laying out our school newspaper, the Wildcat.

"How's this for my lead? 'Homecoming, Sadie Hawkins, Spring Fling, and Prom: A Four Course Feast of Fake Nostalgia for a Sketchy School."

Anne passed her the drawing.

"Here's your subtitle: 'Rituals for jocks and their chicks to feign monogamy.'"

Barb's fingers clattered on the keyboard.

"Perfect segue: 'So the Marlboro men and their Stepford wives can breed the next generation of Smurfs.'"

I nodded enthusiastic agreement. But my solidarity masked the dissonance I felt at their denunciations of male sexism and feminine submission.

Quinn sketched a caricature of Barb as Joan of Arc battling robotic football players.

"Everyone's been reprogrammed. We are the only humans left in this zombie zone."

I struck an orator's pose.

"I'll play devil's advocate. If we don't record these adolescent passages, aren't we abdicating our roles as journalists?"

Anne yawned.

"Been there, done that: we reported on date rape drugs last year, got a football player expelled."

"I was three years a hostage in a monastery masquerading as a prep school. I want memories to sustain me during college."

I gestured downing a shot, smoking a bong and snorting a line. Quinn crumpled and threw another drawing into the garbage can.

"Partying got you kicked back into this hell-hole?"

People often asked what Caulfield-esqe faux pas had gotten me ejected from my elite Jesuit prep school. The truth, that my Jesus-loving roommate reported me for dildo-masturbating while cross-dressed, was too embarrassing. I hewed to a safer fiction.

"I organized a rally for a suspended gay teacher, lost my scholarship."

Barb gave me a thumb's up.

"Their loss was our gain. Screw tradition, toss normalcy, and invoke chaos. Let's gay date on Homecoming. Me with Anne and you with Quinn."

"Truth or dare?"

"If not now, when?"

"Seize the moment."

We anointed ourselves the Intellectual Mafia, and dominated debate, academic decathlon, yearbook, and journalism, pursuits to which our classmates indifferent. The ordinary curriculum was beneath us, we took mostly AP classes. We obsessed over Existentialism.

We were outsiders, friends only with one another. Quinn was openly gay, Barb was lesbian, and Anne and I classified ourselves as 'questioning,' which in my case meant that I was too intimidated to come out.

Uni High had been a top public high school but had been reduced to mediocrity by the legacies of busing and budget crises of the Nineties. Wealthy residents of the surrounding neighborhoods sent their children to private schools. Only a handful of gifted students remained, stranded by their parents' modest finances.

In the traumatized aftermath of 9/11, the other students of Uni High had cocooned themselves in social certainties of the past. An overt display of our divergent sexuality at Homecoming would invite retaliation by the jocks who held high school rituals sacred, the Saved by Christ cult in whose eyes gays, lesbians and especially transsexuals were damned, and the gangsters who targeted LGBT students as vulnerable victims. The closet was the safest place to survive Uni High in the fall of 2001, so we held our fire at Homecoming and planned a more strategic escapade.

Secret Persona

Uni High was my neighborhood school, but I was an outsider. My parents shipped me off to an elite boarding school, St. Aybert's, after a traumatic eighth grade when my classmates bullied the skinny nerd whose puberty had lagged. But St. Aybert's had no tolerance for gender variance and stripped my scholarship after my junior year, leaving me no option but returning to Uni High, barely changed from the effeminate prepubescent that had left.

My male classmates had grown into roughshod manhood, and initially regarded the returning, half-forgotten waif with amused contempt. But that soon soured into resentment of my intellectual hauteur and derision of my androgynous appearance.

St. Aybert's stringent academics and practice of muscular Christianity had stunted me socially. Exposed to the vulgar whirlwind of adolescent fads at Uni High, I became a pop culture junkie obsessed with observing the Byzantine rules, and skirmishes between the cliques and the genders.

I affected the pose of a sarcastic social critic. But my image was a façade, a cage and fortress behind which a secret slut languished, awaiting her debauch. She would willingly be drugged and smuggled out of Homecoming by a heartless jock, submit to casual back-seat sex, and be cast off and recycled for the next guy's fun fuck. But she was imprisoned by ambition and inhibition.

I didn't dare reveal my feminine persona to the bigots and gangsters that ruled Uni High. I scuttled between my Advanced Placement classes like a refugee through a no man's land. Jocks bumped me in the halls, dopers mocked me in the quad, the born-again Christians lectured me about conversion therapy, and the gangsters glared and mouthed "faggot" at me. Did the gangsters' connections with crime and commercial sex let them peer through my intellectual condescension and see the submissive sissy slut inside?

She emerged only at night, when I stroked my tiny dick while fantasizing the assaults that I desired and dreaded. Imaginary thugs slapped my face and silicone breast forms while I dildoed my ass. I endured searing pain for the first moments of penetration, until my colon relaxed, and I plunged and tugged my way to orgasm.

I douched my ass to keep my toys and bedding clean. I practiced pulsing my anus to accelerate and accentuate the panic, pain and pleasure of penetration. I licked my toys and belly clean and learned to love the tastes of ass mucous, lube and cum. Each morning, I scrubbed away the sticky residues and hid my sex toys like my fantasies. I brushed and gargled the ass musk and cum from my mouth and resumed my pretense as a male merit scholar and class intellectual.

I cloaked my transsexual identity behind my intellect and accomplishment, imprisoned my inner girl until she could safely transform and take wing like a butterfly from its chrysalis. Secrecy was imperative, for when I was exposed at St. Aybert's, I'd been forced out. My ambitions required me to conceal my transition at Uni.

Teacher's Pet

I minimized facetime with the unwashed masses at Uni by taking all available Advanced Placement classes. Math AP wasn't offered at Uni, so I settled for Algebra II, which I'd covered as a sophomore at St. Aybert's. Mr. Rogers handed out marked up homework and was met by groans lamenting nearly universal failure.

"Let's go over your problems. Marta, you had some problems with quadratic equations. Do you want to explain how you approached the problem, so we can get to the source of your mistake?"

"I got stuck, and finally just guessed."

The class laughed, she blushed, and so did I. Marta Gonzalez had been an adorable sprite in Middle School, whose pert boobs, slim waist, olive skin and sleek hair foretold spectacular beauty. We became good friends, and I thought about her frequently after my parents bundled me off to St. Aybert's. We exchanged occasional emails and texts, but we had lost touch by the end of my exile.

When I returned, she'd become Uni's Jennifer Lopez, the girl I had always wanted to be. She had baby doe eyes, ballistic breasts, and pouty, full lips. She had dated the coolest jocks and coldest gangsters at Uni and floated between these mutually exclusive enclaves with ease. But her popularity must have distracted her from studies.

I raised my hand.

"Rios, go ahead and educate us."

I went to the board, solved Marta's problem in three easy steps, and she smiled and winked. The teacher called on a muscled, tatted Latino slouched in the back.

"Miguel, tell us your thought processes on the second question."

Miguel Carranza had been held back, but he'd turned this humiliation to his advantage and used his age and size to the lead a pack of fellow flunkers who persecuted smaller, weaker boys like me. He'd taunted me as a sissy, I called out him and his friend Jack as flunkers, he'd bloodied my nose and incited Jack to stomp my prostrate body. My father had bullied their names from me, they'd been suspended, but in the end, they bested me, for it was I who was exiled to St. Aybert's. .

"Let smartass Rios explain it."

"Give your paper to Rios. Alex, tell us where Miguel went off the rails."

"He never got on track."

"Show Miguel how to solve it."

I solved it and handed the paper back to Miguel, who snatched it.

"OK, Carranza, copy Rios's work on the board."

Miguel copied my solution, but added "Alex Rios, Sissy Faggot" beneath. The classroom burst into laughter; Mr. Roger's erased the slur.

"Carranza, take this pink slip to the principal's office."

I approached Mr. Rogers after class.

"Can't you get me out of here? Carranza hates me."

"It's a requirement."

"I'm sure I could ace your final today."

"Here's last year's final. Give it a shot."

I finished the test in twenty minutes. Mr. Rogers let out a low whistle when he finished marking it.

"Even so, I can't excuse you."

"Then have me tutor the others."

"These losers?"

"I need community service credits anyhow."

The next class Miguel was assigned to my front row seat and I sat at a table in the rear of the class, tutoring Marta. I coached her through the mysteries of multivariable equations, and she giggled with delight when she finally solved one herself. Miguel scowled over his shoulder and raised his hand.

"Can I have some tutoring now?"

"Only after you write an apology on the blackboard."

Miguel went to the board and wrote "Sorry for calling Rios a sissy faggot."

The class burst into a round of applause. Mr. Rogers handed him another pink slip

"Get out, and don't come back"

Miguel got suspended for sexual harassment and reassigned to a different section. Marta became my most frequent tutee and Mr. Rogers' most improved student. We once again became BFFs, best friends forever.

Formulary

Perhaps my physique destined me to be transsexual. I was pale, slender and weak, always the last picked for every team and the slowest in every race. My balls had failed to descend normally. After they were surgically extracted my genitals developed like a pre-pubescent's rather than a man's. Adolescent gynecomastia caused my breasts to swell to A-cups, and my boy boobs were still soft and jiggly when at 16 I finally jerked myself to my first orgasm, fantasizing about being a girl.

The summer after I got kicked out of St. Aybert's I noticed the onset of my long-delayed puberty. My pubic peach fuzz thickened, a wispy mustache sprouted, and my high-pitched voice occasionally cracked. I panicked at the imminent end of my androgyny and decided to delay the onset of my manhood until the girl inside of me could safely emerge. I'd studied the websites and done the research, knew what I had to do to keep my transsexual option open, while the ambitious boy and the romantic girl wrestled in my subconscious.

To keep me busy and out of trouble, my dad arranged an internship at the UCLA medical school coding data from drug trials. It was boring and lonely but gave me ample opportunities to rifle through medical supplies that the drug companies lay off at clinics. There were cartons of syringes and vials of estrogen and progesterone in the supply room. Fully aware of the transformative power of these drugs, I smuggled out needles and hormones and began self-administered hormone replacement therapy, or HRT.

I injected the hormones in my inner thighs, where the needle marks and the bumps left by the viscous progesterone would be less noticeable. The needles' pricks and my pain became symbols and signposts of my passage. I imagined that the proximity of my injection sites to their target intensified their assault on my incipient masculinity.

My acne worsened at first, and then suddenly disappeared. My hair became smooth and manageable. After a couple of months, my nipples broadened, my body hair thinned, my muscles atrophied, and my skin became luminous and soft. My emotions swung between giddy joy and gloomy melancholy, punctuated by frequent outbursts of tears.

By the time I started my senior year, I had entered awkward phase of transition, when the effects of hormones become discernible, but not definitive. The skinny wimp who had left for prep school three years earlier had returned an androgyne. My altered appearance made me the target of frequent bullying, at lunch, in the halls, and worst of all, in the locker room.

Solving for X

Marta and Thad Jones, Uni's star football linebacker, stared cluelessly at the equation I'd written on the blackboard. Thad shook his head.

"Only X's I need to know are in football plays."

"The world is full of X's, algebra solves these unknowns."

Marta cradled her face in her palms and smiled.

"Maybe they're supposed to stay unknown."

Was it New Age piffle, or sly innuendo about my chromosomal X' and Y's? I blushed and turned to the board.

"Thad, in football, what makes a good play?"

"Isolate a stronger or faster player against a weaker or slower one."

"Exactly the same in math."

I divided, subtracted, and multiplied the equation's numbers by their inverses until the X was by itself, and the remaining factors were on the other side.

"Now it's simple, X=5/Y. So if Y is 10, X is-"

Marta shot up her hand first.

"Two."

"Thad, what do you think?"

"I'll go with that."

"Close, but try this."

I erased the Y, replaced it with 10.

"5 divided by 10 is-"

They answered "half" simultaneously, I fist bumped Thad and shook Marta's hand, soft and delicate, it fit perfectly with mine. She blew me a kiss, I imagined her breath sweeping away the Y's from my genome like the one I'd erased from the blackboard and replacing them with her bountiful X's. I blushed again, turned to the blackboard.

"You're getting it, let's try one with three variables."

I wrote another equation on the board.

Physical Education

None of the athletic torture I had endured at St. Aybert's met Uni High's mandatory physical education credit, so I was required to take Phys. Ed. I had never been fleet afoot, but HRT had so slowed me that my mile time was the worst in my class. The coach made me run an extra lap, so I was late to the locker room, which was almost empty as I mopped cold droplets of my hurried shower from the goose-bumped skin of my buttocks.

As I finished drying, I sensed appraising eyes staring at my naked body, heard muffled snickers, ignored them, hoping my indifference would discourage their invasion of privacy. When I bent over to open my locker, the towel parted and slipped from my waist, displaying my naked, upturned ass. Miguel laughed.

"Nice ass, Rios."

"Isn't one harassment suspension enough?"

He slammed me into a locker.

"Don't forget middle school."

He turned to his friend, Jack.

"Let's fuck its ass in the laundry room."

He snapped me with his towel, raising a bright pink welt on the curve of my left buttock. I stifled a scream and spun around, covering my privates and the slight bumps forming under my nipples, frightened but aroused. How could Miguel know my secret fantasies?

"I'm sorry, don't hurt-"

"What sissy gets for messing with me."

Miguel pushed me against the lockers and forced me to my knees. He unzipped, seized my head and pressed my lips against the fly of his boxers. The smell of his groin suffused my nostrils.

"Suck it, maricon."

He'd tagged me with Spanish epithet for faggot. My face reddened but my terror was mixed with temptation. Part of me wanted to suck him, let him fuck me, but what would happen in the aftermath? Public exposure terrified me.

I wanted to transition in college, away from my bigoted classmates and my hovering parents. The policies of the school district mandated accommodation for transsexuals, but the practical reality was that transsexuals tended to disappear into a special school in Hollywood soon after they came out. If I got relegated there, my college applications would be toast.

A door banged, and Coach's footsteps approached. Miguel flung me aside, spat out "fucking faggot," and he and Jack sprinted to the exit. Coach eyed me with contempt.

"What's your problem, Rios? Crybabies don't get special treatment."

Coach taught "Human Development". He hated gays and probably thought transsexuals were even more despicable.

"I feel sick."

"No excuses. Just do it, Rios."

I promised I would, but instead, I faked a knee injury, forged a doctor's note, and got excused from physical education.

Retreat from Rubicon

Surreptitious HRT had brought me to the threshold of visible transsexual transition, the tipping point where androgyny succumbs to femininity. I was torn by conflicting priorities.

If I interrupted HRT my skin would revert to oily acne and my hair to a tangled mop. Testosterone unopposed by female hormones would irreversibly the change my face and body into a man's.

Transsexual transition delayed until adulthood produces imperfect results. Adult transitioners develop squared jaws and thickened brows, which even the most expert facial feminization surgeons cannot eliminate. Their voices are deep, their bodies are thick, so they are clocked, mocked and persecuted.

Adolescent transition produces a more passable result. If I continued with HRT, my breast and nipple development would accelerate. But the emergence of female secondary sex characteristics coincides with permanent and irreversible spermatic infertility.

I was ambivalent, determined to fulfill my female destiny, anxious about transitioning in a hotbed of transphobia and guilty over denying my father the continuation of the Rios lineage. The prospect of infertility worried me, but a future maturing as a male was even worse.

But my locker room encounter proved that I could not transition under the radar in the transphobic fishbowl of high school. I got a post office box for delivery of pharmaceuticals and found an online pharmacy to prescribe Aldactone, the commercial version of spironolactone (Spiro), an anti-androgen that stops masculinization. I curtailed my estrogen and progesterone intake and went in a gender holding pattern. I would resume my transition at college far from my parents and the intolerance of Uni High.