A T-Girl and a Tomboy Pt. 01

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A closet CD is outed by the cheerleaders.
28.9k words
4.73
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135

Part 1 of the 4 part series

Updated 06/10/2023
Created 07/10/2020
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AlexBailey
AlexBailey
167 Followers

Outed by the Cheerleaders

_________________________

Hello!

This is part one of a full length novel in four parts. It's a gender-fluid, 'what if everything fell into place,' fantasy about self-discovery, coming out and coming of age. It explores pansexuality, cross-dressing and several fetishes -- especially for things like swimsuits and athletic-wear. Some parts have bondage and D/s themes. There are family dynamics and dysfunctions, social conflict and misconceived religious interventions. The enthusiasm and foolishness of youth is at play, and there is experimentation with drugs. Some characters are hostile and bring a touch of violence, and of course, there is a lot of kinky sexual adventure, often gilded with loving romance. All characters are 18+. Enjoy!

__________________________

****

Half Awake

Some part of my rum-soaked brain is trying to wake up, trying to adjust to the ambient din of the ocean waves and crying seagulls. Being cautious not to open my eyes too quickly, not knowing what I might find, I try to swallow and feel sand in my teeth. The acrid smell of burnt driftwood is all around and in my tangled hair.

I'm on my side, laying on a blanket on the beach. I'm sharing it with someone... It's Sam. He's behind me and we're using an open sleeping bag as our only cover. Oh wow! He's holding me. How did this happen? Sam, my twenty-one year old surf instructor, is cuddled up behind me, holding me close to his body. I'm using his huge bicep as a pillow.

A little more awake now, I feel his other arm slung over my side, fingers loosely splayed across my belly. His unconscious touch is a cross between coveting and clinging with an occasional twitch or caress in reaction to something in his dreams.

What are we doing here? I rack my brain trying to remember last night. Sam wanted me to have fun on my eighteenth birthday, so I went along to spend the night on the beach near Ballina, not exactly sure what he had in mind.

Why in the world would he be sleeping on a blanket with me when those two Aussie surf bunnies had been fawning all over him last night? He introduced me as his 'Yankee shark-bait brother.' The girls probably wondered why he was bringing a 'grommet' like me, thinking I would just be in the way of a good time.

Finally, more awake than asleep, I open my eyes to look for clues. Lifting the sleeping bag to peek around I see the two surfer girls asleep and snoring like the waves on a blanket across a smoldering fire pit from me and Sam. I think he invited them with the intention of pairing up — so why is he holding me?

The sun has risen just above the ocean. If we were fresh and ready we'd be headed out to surf the dawn patrol, but this daybreak I contently settle against Sam and feel him pull me back even closer.

Not knowing how I ended up here or how long it will last, I turn my attention to enjoying the moment, just grateful that it happened. I inhale his scent with every breath. The musky smell of his body is strong and alluring in spite of all of the dark rum we apparently finished off.

I already admitted to myself that I'd developed a crush on Sam, one of the few guys that I ever imagined being touched by, but I never let on to him...did I? Does he know how I feel? My mind races again, trying to figure out how he could know and wondering what may have changed last night. Nothing. I don't remember anything. I take a breath and try to jog my memory. I close my eyes, take in his warmth and feel his strength.

There is something about Sam and the way he makes me feel; respected and precious, sometimes even pretty.

When I'm home in California I often cross-dress in private, but away as an exchange student, I'm too busy and I have too little privacy for such pleasures. The sexiest thing I could easily stash in my luggage is a Speedo thong. With Sam's hands so close, the one I'm wearing now under my board shorts helps wake me up down there.

As if reading my thoughts, Sam lets go of my belly and slides his hand down the back of my shorts. His fingers find my thong, and he sleepily traces it up and down between my ass cheeks. My cock begins to rise to attention. I shift my shorts to make it more comfortable as things grow, just barely rousing Sam. His breath catches and his body tenses for a moment—but he settles back to steady breathing, slow and deep. The mere sound of his breath reflects how much bigger he is than me, a full foot taller and nearly twice my weight, with his well-defined muscles, and his beautiful surf-tanned body dwarfing my small frame. I'd been dreaming and having fantasies of resting in his arms, now here I am.

He sniffs suddenly and shifts his weight a little, becoming aware that he's wrapped around someone. His strong arms curl and he pulls me to him, his nose behind my ear as he inhales and lets out a soft sigh.

Shifting his weight again and pulling me closer, he nuzzles my neck, lets go of my thong, and grabs my ass through my shorts. I gasp too loud in surprise. He holds me even tighter with one arm underneath me, all the while massaging my ass and thigh with the other.

"Uh, Sam..." I whisper nervously, realizing he might be drunk and not know it's me.

"Yeah..." he says in a breath, "Hi."

His huge paw squeezes my ass again. His thumb hooks the waist band of my board shorts and pulls them down to my knees. I feel a rush of cool air and eagerly kick them off of my bare feet. Is this really happening?

He caresses my hip and his fingertips trace my thong again. His tongue goes in my ear and now he's sucking on my lobe, biting gently. I gasp. He grabs the t-back of my thong and yanks it up my back, pulling it up my ass and tugging at the base of my cock. Fuck! I'm completely overwhelmed! I've never been manhandled like this before. I can't believe how wonderful it feels—I just never knew! It's like how you can't really tickle yourself... I've never made myself feel this good; Sam is doing this to me! I roll over to face him and find his eyes closed.

"Sam?" I ask, not convinced he's awake. "Hey, Sam?"

He kisses my lips with his eyes still closed, my heart wants to race with joy and I want him to put his tongue down my throat, but I need to see his eyes first. I move to hold his face and his hands slip to my crotch... Uh no! A shudder tells me he's found something he didn't expect. Sam's hands falter and go stiff for a moment, he inhales sharply. Unfocused eyes burst open, fingers grasp and grope between my legs trying to figure out what the hell is going on.

"Alex?" he demands, apoplectic eyes finally focusing on my face. "Oh, bloody fuckin' hell!"

Adrenaline surges and he scrambles to his feet. The sleeping bag sails through the air and settles onto the smoldering coals of the fire. Stomping and staggering, cussing and swearing, he's off down the beach.

The surf bunnies are startled awake. "Hey, Sammy! Where you off to?"

Their disappointment is obvious as Sam leaves with no explanation. They turn and look to find me on my knees in nothing but a thong and eyes full of tears.

"Oh, fuck! Sam?" I cry, bewildered. He wasn't awake!

***

The Rear View Mirror

A week later I'm headed up the East coast highway of Australia, headed for the Brisbane airport to catch an evening flight back to the states. I watch out the back window as the beacon from the Byron Bay Lighthouse disappears from view.

My host family, Sam's mom and dad, are old college friends of my parents. Sam's dad is driving, talking about how glad they are they could take me in for the semester. I'm grateful but having a hard time listening to all of their stories about college days with my parents before I was born. Heartsick, I can't stop thinking about their son.

For my nine months in Australia, I'd spent nearly every weekend in Sam's cozy beach bungalow. How could I have gotten the signals so crossed? I knew Sam had brotherly feelings for me, but it wasn't until I woke up in his arms that I felt sure he was attracted to me. I'd felt some awkward tensions before, so it seemed possible that he was just shy and didn't want to let it show. He was asleep when he touched me—everything was fine until his fingers found my cock. How could I have let it go so far before I knew for sure he was awake? Did I take advantage of him?

All of my life, I have often been mistaken for female, but nothing like this. If I was a girl things would have gone very differently.

Sam had been planning to hang out with me for the week after the Australian school year ended and before I had to go back home, but after that morning he left a handwritten note about how he had to leave, but that I could stay in his bungalow -- there was some job he suddenly had to go do for a friend in another town. He wrote about how sorry he was that he would not be back in time to see me off.

This has been a pattern for me. I've never had much luck in relationships with men, no brothers, no close friends, I'm not even close with my own father.

Sam's mom tries to make conversation from the front seat.

"Too bad you and Kayla aren't going to see each other. It's funny that you've never met, but you've stayed in each other's rooms."

"Thanks, Jessica. I'm sure we'll cross paths someday. I'm grateful for the space. It would have been hard to get any school work done at the bungalow," I say, trying to perk up and not sound so depressed.

"I hope you can visit Oz again soon," Jessica says, "we've been wanting to get back to the States. Sam was talking about getting off his duff and going to school there. He's applying to UCLA for next fall, so maybe he can stay with you."

My heart floods with regret. I can't imagine Sam would want to come to California now. I'm miserable thinking about how differently things could have turned out. I try to avoid talking about him.

"Mom is always busy but she'd love to see you. You just have to plan ahead and find a spot on her calendar," I say, trying to smile and sound upbeat but I can't mask my disappointment.

Jessica turns and looks from the front passenger seat.

"Are you and Sam okay? I can't understand what job would make him miss your last few days. It must have been really important. I'm glad you two got to spend so much time and get to know each other—you're almost like real cousins."

A piece of my broken heart catches in my throat and I can't keep my voice from cracking.

"I'm sorry Jessica, I can barely keep my eyes open. I didn't get any sleep last night."

***

Big Ohana

My flight to California has a short layover in Honolulu. I'd spent my sophomore year on the Hawaiian island of Oahu, now I wish I'd planned some extra time so I could visit Auntie Tutu; the matriarch of the family I stayed with my sophomore year. I took classes from her while working at the botanical gardens reserve.

I doubt anyone knows how old Auntie Tutu is, probably not even herself. She'd lived at the reserve before it was designated and is a sixth or seventh generation matriarch. Smart as a whip, she knows nearly everyone who is originally from Oahu and most of the families of the other islands. Hawaii is that way, big 'ohana' -- big family. Everyone knows everyone's business there, and Auntie Tutu is an elder.

With an eerie way of knowing things, almost psychic, she managed to get my whole life story out of me the first time we worked the gardens together. When she would talk, I would eagerly absorb her stories of the Hawaiian legends.

She would come up with personal nicknames for the people she got close to. Once she came up with a nickname for you, everyone around would pick up on it too. She called me, "Haole' Māhū". When I asked, she said 'haole' is a non-islander and that the 'Māhū' were traditional healers and spiritual advisors. They were friends and consorts of the Hawaiian royalty and keepers of stories and traditions. She didn't make a point to tell me that Māhū were traditionally men who presented and lived as women.

Other kids laughed and told me that Māhū was Hawaiian for 'gay,' but Auntie Tutu told them, "It's kapu to mess with Māhū. Don't be disrespectful."

I learned the stories and was proud to have the nickname and became known by it, my own name nearly forgotten during my time on the island. Whenever I was introduced to another elder, the name seemed to be respected, often with a slight nod of deference.

I'd met some Māhū at the gardens when they came by to visit or volunteer. They seemed like eccentric monks to me. When I got home, I looked it up online. Traditionally, 'Māhū' is someone who is neither male nor female, someone who is, "thought to inhabit a place in the middle." Hawaiian culture has a lot of gender fluidity, including royal consorts and a tradition where the youngest son of a family of all boys could be raised as a girl so the mother would have a helper in the home. Unlike western culture, the Māhū are -- or were—a respected part of Hawaiian society. Nowadays, 'Māhū' is sometimes used derogatorily, but there is a large degree of cultural acceptance.

Auntie Tutu never made any point about gender, but when I thought about it later, while the other interns were separated in male and female dorms, I was always invited to sleep wherever I wanted. Work assignments were often assigned by gender too, but I was given tasks that were traditionally either men's or women's. Auntie Tutu liked to have me around as her personal helper.

Sitting in the Honolulu airport, I'm sorry I didn't plan a longer layover so I could visit her. She is the one person I could talk to about my confusion right now. Just thinking about her brings my spirits up. I board the plane in a better mood which only improves when we take off and I spot the reserve through the window as the plane banks toward LAX.

I promise myself that I will return someday.

***

California

Mom is on her cell phone when she picks me up at the curb in front of the LAX airport terminal. I load my baggage into the van and hop into the passenger seat. Mom flashes me an apologetic wink as we pull away from the curb and head home.

"Sorry, honey. I've got to make these calls—we can catch up at dinner tonight."

It was always the same with Mom, constant networking.

I watch out the windows as we sit in traffic on northbound Highway 101. The joggers on the frontage road are passing us while we're stuck in commute traffic. A girl in a pair of shiny turquoise tights catches my attention. I can't keep my eyes off her legs.

There's something about the smooth, taught fabric holding a body so snug and intimately; things like tights, or one-piece swimsuits -- either on someone else or wearing them myself... Unfortunately for my fashion sense, and unlike my twin, I wasn't born female.

My parents had three kids, my older sister Jess, my twin sister Tonya, and me. When Mom got pregnant for the second time, she had a sonogram showing twin girls. My parents bought our house in the school district in Ventura County where my mom had received all of her Olympic gymnastics training. Once we got to high school, she'd planned for us to attend the same all-girls' prep school she had gone to. She wanted to provide her three daughters with the same athletic opportunities she'd had.

The problem with her plan was me. I'm the boy who'd defied a sonogram. They were expecting twin girls, deciding on 'Tonya' and 'Alex', not Alexandra, not Alexa, but... surprise! A twin birth is a busy time in a hospital and no one thought to change the 'F' on my file to an 'M' and no one noticed the incorrect birth certificate until after we got home. Mom supposedly got it fixed over the phone and my new official birth certificate was to be sent in the mail. We were supposed to destroy the 'F' copy when we received it.

I don't know if we ever received the 'M,' but Mom never destroyed the 'F' copy. I've wondered if she planned it all along. I doubt she ever intended to send me to a different high school. After Tonya and I finished eighth grade, Mom probably went to the high school office, put our 'F' birth certificates on the counter, and said, "I'd like to register Tonya and Alex Bailey. Alex will be enrolling in the new off-campus independent study program." She didn't lie, she just avoided having me appear in the office by working with a friend who was my guidance counselor. I was enrolled as an independent study with an online student-porthole, so I never was seen on campus.

Mom had been on the US Olympic gymnastics team. She was a competitive gymnast and a cheerleader in high school and followed the scholarships to college. She got married and had kids and when her first daughter got into school, she worked and organized and made the school into a scholarship generator. Now she was able to cash in on some favors.

Since I wasn't into team sports, Mom and her friends made a special curriculum for me, creating an exchange program for on-location outdoor sports; sailing, surfing, biking, kayaking, snow sports, and backpacking. The plan was to create a network of outdoor adventure programs and internships with facilities and families willing to host them. When a classroom wasn't available, classes were online. They created a new program to expand the school's offerings.

For my freshman year, I was at sea in the Caribbean on a tall ship/boarding school. Our curriculum was intensive as we located several shipwrecks and researched the crew and cargo. Back at the school office, the fact that I was a boy never came up. After that I could simply remain enrolled as an off-campus student while I traveled overseas and experience more of the world than any of my peers.

***

Sisters' Love

The drive home takes more than two hours, with Mom on the phone the whole time. Eventually, the traffic lets up, and the van is able to move faster than the joggers again. When we finally get to our exit, we take the freeway off-ramp and pass through a beige town of brand-named franchise stores with palm trees scattered about the vast parking lots.

We drive a few miles up a narrow, forested canyon road to our driveway. Mom presses the clicker on the sun-visor, and the iron gate swings open. A long driveway makes several switchback turns up to our modern stone and stucco house with a red-tile roof. It's a multi-level five-bedroom, built into a hillside, with a backyard pool and a quarter acre of lawn. The attached garage is huge.

At the top of the driveway my sisters are waiting for me on the front steps.

My twin, Tonya, looks like she just got home from squad practice. She is a beautiful, athletic cheerleader in her black and red uniform with long auburn braids. She is the female version of me.

Jess, my older sister, is home from the college dorms at UCLA tonight so she can welcome me back. She's tall, broad-shouldered and muscled all over, with a square jaw and short bleached hair, looking her part as a college-student sports-coach for high school teams.

It feels unbelievably good to see them after so long. I'm closer to my sisters than anyone else in the world. The van barely comes to a stop before they rush it and open my door. We hug long and hard as a rush of tears sweeps over me. I lean back to wipe them and see that Tonya and Jess have the same. The three of us giggle and laugh and hug again.

Asking a million questions, they help me bring all of my stuff in and follow me around the house as I get settled. The requisite debriefing dinner lasts hours before they finally head off to bed and let me get settled back into my room.

On my pillow is a thank you card from Sam's sister, Kayla. She had been staying in my room while I stayed in hers. She thanked me for the use of my bike and surfboards and apologized for making everything smell like her perfumes.

The sheets have been washed, but my pillow and mattress still smell like girl—not that I mind. In the card, she's included a signed picture of herself and a dozen other smiling cheerleaders piled on my bed. I study their faces and recognize several of them. I imagine having them all here now, hanging out, welcoming me back home. I tuck the pic into the frame of my dresser mirror, wishing that I could be part of the squad.

AlexBailey
AlexBailey
167 Followers
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