Finding Our Real Selves

Both of these protagonists are transgender. I swap the pronouns I use for them halfway through the story so if you suddenly notice that change, it's intentional. All characters 18 cuz I said so etc etc.

If you notice weird breaks it's cuz this story was initially written as 7 different individual submissions.

***

"Sam? No partner yet?" The 'life skills' teacher Mrs. Fredericks called to him. Sam looked up, slightly startled. He didn't know anybody in this class, and had been looking around the room for someone as lost as him to partner with for the assignment. Talking to people had been out of the question of course. His plan had been to create uncomfortable eye contact and then just sort of wander over to them.

Sam looked back at his teacher and shook his head. "Right, pair up with Brittney then," she said, gesturing to someone sitting at a table in a secluded corner just like the one he was sitting in, except on the other side of the classroom. Sam nodded and picked up his things, making his way across the classroom to... Brittney.

He'd never actually interacted with her before, she wore loose clothes, her dirty blonde hair was cut in a very short somewhat disheveled pixie, that didn't exactly look masculine but wasn't especially feminine either. She was about the same height as Sam - which was more because Sam was short at 5'6", rather than Brittney being tall.

"Call me Britt," she said, shooting a look the teachers way, seeming annoyed that she'd used her full name.

"I'm Sam," he replied, raising his hand a little to begin the motion for a handshake, only to lower it again as his brain's overactive second-guessing instinct kicked in. Britt, however, showed no hesitation, extending her hand and offering him a cool smile. He took her lead and returned the shake, if a bit awkwardly.

The assignment was to interview one another and then describe the other person to the class. Sam had been dreading it, but Britt proved to be easy to talk to and he found himself talking easily, and learning a lot about her. When she cracked a joke, he found himself giggling at it a lot louder than he realized, and stopped only when the teacher cleared her throat and gave the two of them a dirty look. The attention made him blush and put his head down. Britt re-engaged him though, and they kept chatting for the rest of the class about music, books, and games. They didn't actually have THAT much in common interest-wise, but it worked anyway.

"I'll... umm... see you next period?" Sam offered, figuring that since the assignment wasn't due until that period that he didn't have to worry that she'd think he was hitting on her with the statement.

Sure! See you then," she said, standing up and heading out the door ahead of him.

As Sam got his stuff together and started getting ready to leave, he found himself thinking about her quite a bit. Not just because he had testosterone in his blood and that's what testosterone does, but more broadly, because he'd found girls attractive before but had never really liked or been comfortable around one. It was... odd. Especially since he wasn't 13 anymore by a long shot, wasn't it too late to start liking girls now? Maybe he was a late bloomer or something, he'd heard people say that to him before. Then again, people said... lots of things about him, and most weren't flattering.

His reverie was broken when, as he walked past the gated off tennis courts on the school grounds, someone abruptly came up behind him and shoved him. He stumbled and fell straight into the fence. Luckily it broke his fall and he didn't faceplant into the concrete.

"Hey, Sammie," the all-too-familiar voice of Jared called out. "When I'm hitting on Sabrina I don't need your faggy little laugh interrupting me in the middle of class," Jared towered over him.

Sam looked down at the pavement. "Uhh... sorry..."

"If you wanna act like a little fairy don't do it around us norm..guh" Jared continued his rant, but was cut short when he fell forward, with no fence to catch him, he certainly did do a faceplant on the grass.

"Whats your fucking problem, Jared?" It was Britt. She looked pissed.

Jared picked himself up quickly, and glared at her. "Your Dyke girlfriend here to stand up for you, Sammie?" He sneered.

Britt took a step towards Jared "Don't look away from me and harass Sam again, I'm not done with you." Jared... paused. The gears were clearly turning in his head, and people were starting to notice the spectacle.

"Fuck this," he grumbled, and stormed off.

"Uhh... thanks..." Sam said, standing up and grabbing his backpack from where it had fallen on the ground.

"Happy to. That shithead give you trouble like that a lot?"

"Yeah... kinda," Sam said.

Britt looked at him and smiled. 'DONT BLOW THIS DONT SCREW UP' "Umm. Do you wanna maybe hang out? Sam offered, never having felt more nervous in his life.

Her face lit up. "Sure! I kinda wanted to go for pizza anyway," she said, grabbing him by the wrist and dragging him a few steps with her until he started walking fast enough to keep up with her. The pizza shop she'd been talking about was just across the street from the school, and soon they were seated on a stone bench just outside the store, eating their food.

Britt broke the silence, "I think youre really pretty you know, Sam." She was quiet, she sounded thoughtful, where she'd seemed so casual before.

His eyes went wide. He'd never actually been complimented... well, ever before. Let alone 'pretty' she was the girl, not him. Britt started laughing at his expression. "I... thank... uhh..." several different responses died in his throat.

"I'm glad you asked me out. I was afraid you'd think I was gross or a lesbian or something." She spoke not really looking at Sam, as though she was still a bit worried about what he'd say.

"course I don't think you're gross. Wasn't really sure about the.. other thing..." Sam said, starting to feel a bit of confidence welling. Britt was just as anxious as he was! Or, maybe not quite, but still.

"Well..." Britt started. I've been wondering that myself. Especially when the boy I kinda like is pretty girly. I thought maybe it was just me trying too hard be normal and straight like my mom wanted. But then i saw that shithead Jared pushing you around and I dunno. I got really protective. It felt right."

Sam winced a little. He had been called girly a lot. Like, a lot. But it was always derisive, bullies, his older brother, his Dad, and even one of his teachers. It was a thing they used to make fun of him. "I guess I am pretty girly, huh?" he mumbled.

"Hey," Britt grabbed his hand. "I like it. Don't be ashamed." Sam looked up into her eyes, through the tear that had formed in the corner of his. Her expression had changed. All day with him she'd been casual, joking. Now there was something else, an intensity. "You're mine. And if anybody gives you shit about being yourself, I'll deal with it. Okay?"

This new side of Britt scared Sam a bit, but at the same time something just felt very... assuring. "Yes Ma'am," he said quietly. He wasn't entirely certain where the Ma'am came from but it seemed appropriate.

Britt, however, pursed her lips at the word. "Ma'am? Hmm"

"Sorry it's just you said..."

"No, it's not that. Buuut..." Britt grinned "I think I'd rather you called me Sir."

"Y...yes Sir."

*****

The next day passed, Sam texted Britt a few times but they didn't have any classes together and she was busy with guitar practice after school. The next day, Sam arrived a tad early to the stupid life skills class, and sat down in his usual spot. He'd briefly considered sitting next to where Britt had been two days ago, but he wasn't sure that he wanted to impose quite like that. When Britt came in, she walked straight over to Sam, planted a quick kiss on his forehead, ruffled his hair, and sat down. Sam blushed bright red, positive that quite a few of their classmates had noticed the affectionate gesture.

"Come with me" She whispered to him, after the class ended. She led him to some... mostly out of the way corner of the school.

"Sir, what are we..." Britt silenced him by pressing him up against one of the lockers, pinning him and leaning in close.

"I want to play with you a little, pet," she whispered in his ear, her hands roaming over his slender chest. Sam shivered as her hot breath sent tingles down his spine.

"Sir, people will..."

"Shhhh, I don't care." As she pressed herself into him, Sam found himself getting very hard very fast, and there was no way she didn't notice his erection poking her in the stomach. Sam let out a feminine whimper as she roughly kneaded his chest. He was quite surprised at how good it felt and how sensitive it was even though he didn't have breasts. Britt growled and leaned in, pressing her lips to his. Sam had no real idea what he was doing, but Britt seemed pretty happy to take the initiave. After several moments that seemed like an eternity, Britt pulled back, staring into his eyes as he panted softly.

"Mmmm, that's a good boy" she whispered heavily to him.

"My... my house should be empty until 6 today?" Sam offered.

Britt laughed softly, "Hmmm... I dunno..." she teased. "Can you entertain me if I come over?"

Sam nodded vigourously.

The rest of the schoolday passed by in a haze, Sam barely got any work done and rushed out of class as soon as the bell rang. Britt met him at his locker. "Lead the way. Can we walk there?"

"Yeah, it's like fifteen minutes." Sam led her to his house in just under ten minutes, barely realizing that how fast he was going. Britt didn't complain though, maybe she was just as eager as he was.

Two steps into the entry hallway she pressed him up against the wall, grabbing his ass roughly and growling at him as she nipped at his neck. She spent several minutes aggressively groping him. A painful set of teeth on his neck, a rough set of nails down his sides. Sam was whining and writhing in needy desperation before long. After several minutes, Britt pulled away a short distance from the nigh-delirious girly boy she had pinned to the wall. "Where's your room?"

"Up... follow..." Sam babbled, stumbling up a set of stairs to his room. He led her into the sparse little room he'd always had because he'd never bothered to pester his parents for a bigger one.

"So, this is-" Britt cut him short by shoving him face-first down onto his bed, laughing playfully. Sam spun around as Britt descended on him, tugging down his pants and underwear. His cock bounced up at attention, hard with a glistening drop of precum already leaking out of the tip.

"It's so cute," Britt giggled, wrapping her fingers around it gently, "Just like you. But don't worry, I dont think I want you sticking that in me anyway." Part of Sam wanted to protest her calling his cock 'cute' but right now seemed like a ... bad time... Britt stroked him slowly but steadily, her other hand keeping gentle pressure on his chest, an unspoken reminder to stay still for her.

'Ahhh... fuu I..." Sam groaned as he felt his orgasm approach, his hips starting to buck wildly, humping his cock into her grip. As he did, Britt stopped abruptly, eliciting a needy whine from him.

"Pet, I want you to ask permission first, understand?"

"Uhh... wha?" Sam babbled.

Britt released his cock and flicked the tip lightly.

"Ow!" Sam cried, the sharp pain drawing him back into lucidity.

"You need to ask me permission before you cum, slut. Do you understand?"

"Yes! Yes Sir," Sam responded quickly. For such a small motion, the flick had actually really hurt, and he was eager to avoid another.

"Good boy..." She grinned down at him, wrapping her fingers around his length again, resuming stroking him. She leaned down as she did, rolling his shirt up and finding one of his nipples with her teeth. Sam braced himself, expecting her to roughly maul them, but instead she was... veerrrryyy gentle, sucking and teasing him with her teeth until he was seeing stars. With how much Britt had been teasing him literally all day, Sam found himself once again on the brink very quickly. "S-Sir can I please-" Sam panted

"Yes," she answered immediately, breaking her lock on his chest for only a second as she switched over to his right nipple.

"Ah! Ahhh! Siiiii" Sam's words were lost to his feminine cries and moans as an orgasm crashed uncontrollably through him. Britt didn't lose a beat, continuing to stroke him as he spurted all over her hand and his stomach. Even as the waves of his climax began to ebb away, Britt continued stroking, the pleasure quickly transforming into something akin to poking an over sensitized nerve ending.

"Please, Sir, too much," Sam gasped, reaching down to feebly try to push Britt's hands away. He didn't have the strength left anymore to actually push her away forcibly, but mercifully she stopped anyway, laughing at him softly. She lay down on the bed next to him and brought her hand up in front of his mouth, her fingers absolutely coated with his glistening ejaculate. She looked at him expectantly. Sam was... fairly sure he knew what she wanted, but wasn't quite sure enough to just dive in and lick his cum off her fingers.

"You got my hand all messy, pet," She gave him a hint, grinning. Sam gulped and opened his mouth a bit. Apparently not requiring any further initiative from him, Britt slipped her fingers inside, slowly thrusting them in and out as though she were finger fucking him. He diligently sucked her fingers clean over the next several minutes, letting her go at her own pace, the wicked gleam in her eyes indicating how much she was enjoying this.

"Very good boy," she whispered, the slightly humiliating praise sending a pleasurable shiver down Sam's spine. She reached back down, running the tip of her finger up and down his slit. He was hard again. "Flip over, kitten. I want to try something."

Sam had no idea what she meant but did what she asked anyway, flipping over onto his stomach. Britt wrapped an arm around his stomach and pulled him up onto all fours. Almost immediately he felt a slick digit rubbing against his pucker.

"S-Sir! What? No..."

"Shhhhhhhhh..." Britt whispered. "This is going to happen, pet. If it hurts, let me know and I'll slow down but I don't want to stop, and that means you're going to do your best to make it so I don't have to, isn't that right?"

"Ahhh... Y...Yes Sir..." Sam whimpered, feeling his obedience to Britt overtake his anxieties.

Britt very slowly worked her index finger inside him, pausing briefly when Sam started to breathe heavy or start to squirm in a panic. With her free hand, she stroked his back and whispered soothingly to him. It didn't take him long to fully relax, and shortly after he did, he felt a second finger join the first.

"You can do it, pet, you're already doing so well." Sam let out a gentle sigh as the second finger worked its way into him, the pain of the stretching had never been that bad and now it was pretty much gone, leaving a strange tingling behind. It wasn't unpleasant, bu-

'Ah! Oh fuuu-" Sam cried out suddenly as Britt's fingers rubbed up against something inside him.

"Hmm? Did that hurt, pet?"

"Noooooooooo..." Sam groaned. It had most certainly not hurt, the shock of pleasure was just something he'd never expected.

"Oh? Well then why don't I just..." Britt started to rub against that spot much more deliberately. Sam shuddered, losing his voice as the persistent rubbing against the spot in his ass drove him crazy. It felt like he was constantly on the edge of another orgasm, he just needed to flip the switch, to drive himself over the edge. Without thinking, he reached his hand down to rub his cock for that little extra push. His hand never made it, Britt slapped it away long before he ever got there.

"You can cum if you want, slut, but no touching."

"S...Siiiiir, but I..."

"What's that? Do you need some encouragement?" Britt asked, gleefully, as she started pumping her fingers into him mercilessly, jabbing into that spot repeatedly.

Sam screamed and cried as Britt dragged him over the edge, his neglected cock leaking a constant flow of fluid onto his bed as he thrashed and spasmed through his orgasm. For the most part, Britt held him down securely, but he eventually got away from her, dragging himself forward and removing her fingers from his ass. To his credit, he was barely even aware he was doing it, he wasn't really aware of anything anymore, he stared up blankly at the ceiling. A drop of moisture hitting him in the forehead slowly drew him back to reality. He was looking up, directly at... what was definitely Britt's vagina.

"Suck me off you little bitch, we're not done yet" she hissed, lowering herself down onto his face. Sam opened his mouth and mostly just sort of guessed at what he should be doing, but Britt seemed not to care much, instead much more interested with grinding herself against him, her hands gripping his shoulders tightly, almost painfully so.

"Fuck.. yes... You little..." Britt cursed and spouted obsenities as she rode his face. Before long, her legs clamped down, squeezing his head tightly, and her hands dug into his shoulders. "Such a good boy... grrrr" Britt's voice went deep and almost sounded feral as she came, her juices flooding his mouth and covering his face. She repeated the process a second time, the second orgasm seemed to take less than a minute before her hands dug into his shoulders so hard he thought her nails must be drawing blood.

"Ahhhhhh..." she sighed, finally loosening her grip. Sam, having not been told to stop, flicked his tongue out over the little nub of flesh nestled at the top of her vagina, which he was at least 90% sure was her clit. Britt immediately squealed and pulled back. "You cheeky little bitch!" she laughed, pulling away from him. Sam smiled sheepishly, not sure whether or not it would be a good idea to tell her he didn't do it on purpose. "I'll get you for that later," she said with a laugh as she lay down next to him and put her arm around his shoulders.

"We... should do that again, Sir."

Britt chuckled. "I'd like to see you try to stop me, slut."

--

Sam closed the door to his room behind him and straightened out his clothes. It wouldn't do to look like... well like what had happened.

"We will do this again, pet, I'm very happy with you." Britt beamed at him and Sam felt his heart skip a beat. Not just because of how great that had been but also because he'd pleased her. It felt like she'd just put a dent in his veil of low self-esteem that he'd only half realized was there.

Sam froze as the two of them got halfway down the steps. The TV was on. It hadnt been on before. Right?

"Heyyy Sammie," his older sister Fran came around the corner from the living room. What was she doing here? She had a soccer game didnt she?

"Sounds like you guys had fun. Gotta say it's about time you came out of the... wait... you're a girl?"

"What does it matter?" Britt demanded, stepping up to Fran before Sam could respond.

"I mean I'm just... surprised? Im sure Dad and Jake would be relieved, but I think we all just kind of assumed..."

"Next time, ask him instead of assuming," Britt said, her voice not quite snide but not exactly warm either."

Fran laughed "okay, okay. Jeez Sam you might not be gay but i guess youre still not the one wearing the pants in this arrangement huh?"

"Uhh... Fran please don't tell-"

"Im not gonna rat you out Sammie, but if you keep bringing her over you'll get caught eventually. Dad might be so happy youre seeing a girl that he'll forget to be mad but Mom will flip."

Sam nodded. Hed remembered when mom had caught Fran's boyfriend staying over one night. It hadn't been pretty.

" It was nice to meet you," Britt said, sounding a bit less hostile now but was still clearly a bit miffed. She dragged Sam to the door with her and put her shoes on. "Walk with me for a bit, Sam."