Blackmail Trans Girl

Caleb Mercer sat alone at the far end of the community college cafeteria, the fluorescent lights humming above the long tables like an indifferent choir. His biology textbook lay open in front of him, the pages already marked with notes he barely needed, but his eyes kept drifting toward the entrance. He told himself he was watching for nothing in particular, yet the moment Elizabeth “Beth” Carver walked in, his pulse jumped hard enough that he felt it in his throat.

She looked exactly as he remembered from senior year and somehow better. Petite, barely five-three, with straight black hair pulled into a high ponytail that left the elegant line of her neck exposed. Tight black leggings hugged the perfect curve of her small, round ass, and a soft pink sweater clung to the modest but unmistakably feminine swell of her chest. She carried a tray with a salad and a bottle of water, chatting with two girls from the nursing program as if she had always belonged. No one looking at her would ever guess the secret Caleb had stumbled onto almost two years earlier.

He remembered that secret with the same mix of shame and heat that had haunted him ever since.

It had been October of senior year. His father’s old college roommate, the high-school principal, had been sitting in the living-room den talking about a new transfer student. Caleb had overheard the word “transsexual” and the careful instructions to keep the matter quiet. The girl would only be there one year. Parents had lawyers. Board had been briefed. The name had not been spoken, but the next Monday a new senior appeared in the hallways: Elizabeth Carver, slim, pretty, soft-spoken, already folding herself into the popular church-girl group as if she had always lived in their quiet New Jersey suburb.

Caleb had already been deep into the videos by then. Clips of girls with cocks, smooth bodies, soft voices, the way they moaned when they fucked or got fucked. The fetish had started as curiosity and grown into something that lived under his skin. When he realized the new girl was the one the principal had spoken about, the fantasy became dangerous and immediate. He had approached her in the lunchroom on a day when the tables around them were mostly empty.

“You’re the new girl from California, right?”

She had smiled, polite, feminine voice light. “Yeah.”

“I need to ask you something.” He had lowered his voice. “Do you like girls or guys?”

The smile had vanished. Her eyes had gone wide with pure terror when he said the next words. “I know you’re a tranny. I overheard the principal talking to my dad. I won’t tell anyone… if you and I can… you know.”

She had gone white. Tears had welled instantly. “You’re going to tell people?”

“I was hoping I wouldn’t have to.”

“Fuck you,” she had whispered, voice cracking. “You’re a real fucking asshole. No. No.”

A few heads had turned. Caleb had walked away before anyone could ask questions. He had never spoken to her again that year. The memory of her terrified face had stayed with him longer than any of the videos. He had jerked off to the idea of her more times than he could count, but every time the climax faded he felt sick. He had never told a soul. Not his strict, church-going girlfriend Paige. Not his friends. Not even himself out loud.

Now they were both at the same community college, and fate or the alphabet had put them in the same biology lab group. Last names starting with C and M had landed them at the same small table for the entire semester.

Beth sat down across from him that first lab day without looking at his face. “Don’t say a word about anything except the assignment,” she had murmured, eyes already glassy.

He had nodded. For two weeks he kept the promise, carrying most of the work while she struggled with the DNA sequencing charts. On the third week, when the homework required home research and she clearly had not finished, he quietly fixed the missing pieces.

“Why didn’t you say anything last year?” she asked softly, voice almost lost under the hum of the lab refrigerators.

Caleb looked up from the paper. “I felt like shit the second I walked away. I wanted to apologize the whole rest of the year. I never told anyone. I never even said your name out loud again.”

Something in her face softened. The next class she stayed after the others left. They talked. Careful at first. Then less careful. She still had it. No surgery. She liked both topping and bottoming. She had never dated anyone from the school. Joe Wilson had taken her to prom without ever knowing. Caleb admitted the videos, the fetish, the way her face had haunted him. By the end of that conversation she was smiling, a little wicked.

“You help me keep my grades up,” she said, “and I’ll help you with something else.”

He had thought she meant a toy. She clarified. “You thought I was going to fuck you, didn’t you?”

His face burned. “Yeah.”

“Do you want me to?”

His heart slammed against his ribs. “I… yeah. I want to try.”

That night she came to his parents’ house. His father was at the hospital until midnight. His mother was out of town. Paige was at a church youth-group meeting and would not text until late. Caleb had cleaned himself thoroughly with the enema kit he bought in a panic at the pharmacy, the cashier’s bored expression still burned into his memory. He answered the door in sweatpants and a T-shirt, already half-hard from pure nerves.

Beth wore a light summer dress that clung to her small breasts and floated around her thighs. Once the door closed she looked him over and simply said, “Get naked. I want to see your butt.”

He stripped. His cock, average length but thick, hung half-swollen between his legs. Beth pulled the dress over her head in one smooth motion. No bra. Small, perfect tits with pale pink nipples already tight. Between her legs a smooth, pretty cock, longer than his by an inch or so, not as thick, already rising. Neat balls, lightly furred. She looked like every fantasy he had ever stroked to, only real and breathing and standing three feet away.

“You have a nice dick,” she said, almost shy. “Do you want to kiss first or just do it?”

“Just do it.”

He climbed onto the bed on all fours, pillow under his chest, ass presented. She climbed up behind him, spread his cheeks with cool fingers, and dripped cold lube onto his hole. One slender finger pressed in, slow, testing. He groaned at the strange fullness. She worked him open carefully, adding a second finger, scissoring gently until the ring of muscle relaxed.

“Stay relaxed,” she whispered. “Breathe when I push in.”

The blunt head of her cock pressed against his virgin asshole. Pressure built. He forced himself not to clench. Suddenly the head popped through and a deep, involuntary moan tore out of his throat. She kept pushing, slow and steady, until her hips met his ass and every inch of her girl-cock was buried inside him.

“I’m all the way in. I’m going to go really slow. Just let go.”

She fucked him with long, careful strokes at first, letting him feel every ridge and the way his walls gripped her. The discomfort melted into a heavy, full pleasure that radiated straight to his cock. He was rock-hard without touching himself. She sped up gradually, short thrusts that made her small body slap against his. He reached underneath and stroked in time with her hips. The dual sensation was overwhelming. Pressure in his ass, friction on his cock, the knowledge that a pretty girl with a real dick was railing him in his childhood bedroom while his girlfriend sat at church.

“Oh fuck… oh fuck it feels so good…”

“Yeah?” she panted. “You like my cock in your tight little hole?”

“Yes… fuck yes… harder…”

She gave him harder. The bed creaked. His prostate sang with every thrust. He lasted maybe four minutes before his balls drew up and he came hard, thick ropes shooting across the sheets while her cock still pumped in and out of his clenching ass.

She slowed but did not pull out until the last spasm faded. When she finally withdrew, her cock was still hard inside the condom. He rolled onto his back, spent and shaking.

“You didn’t come,” he said.

“It’s okay.”

“I want you to. Jerk off for me. Look at me.”

She peeled the condom off and straddled his thighs, her pretty cock hovering over his spent, cum-smeared one. She stroked herself while staring at his soft dick. The sight of her feminine hand flying over that smooth shaft, the soft moans she made, the way her small tits rose and fell, made his own cock twitch back to life. He flipped his still-wet dick side to side so she could see the mess.

“Please,” she whispered.

He stroked himself slowly for her. Their tips almost touched. She came with a soft cry, thin ropes of girl-cum landing across his hand and the head of his cock. The warm splash made him groan. She looked horrified for a second, then saw his smile and relaxed.

“I liked that,” he said. “A lot.”

They cleaned up. She left with a soft kiss on his cheek and a promise to text. That night he stood under the shower and replayed every second until he came again into the drain.

The next day she blew him in his bedroom while his father worked downstairs. She took him deep, tongue working the underside, eyes looking up as she hollowed her cheeks. He came down her throat and she swallowed without hesitation. Afterward she sat on the edge of the bed and let him stroke her until she painted his stomach with her own load.

They started meeting three or four times a week. Sometimes she topped him missionary so she could stroke his cock while she fucked him. Sometimes he bent her over the desk and took her tight, perfect ass, slow at first then hard, until he emptied inside a condom and watched it drip out of her. She taught him how to clean thoroughly, how to relax, how to take a cock without pain. He learned the taste of her precum, the exact sound she made when she was about to shoot, the way her hole fluttered around him when she came from being fucked.

Paige remained oblivious. She still believed in waiting for marriage, still limited him to occasional hand-jobs and rare blowjobs that felt clinical compared to the filthy, eager way Beth sucked him. The guilt lived in the back of his mind, but every time Beth walked through the door in leggings or a short skirt, the guilt burned away under pure lust.

One Friday night his parents were both gone until Sunday. Beth arrived with an overnight bag and a wicked smile. They ordered pizza, watched half a movie, then she pushed him onto the couch and rode his face while he licked her balls and the base of her cock. She came across his tongue. He swallowed. Then she turned around, sat on his chest, and fed him her cock while he reached up and fingered her ass. When she was hard again she flipped him onto his stomach and fucked him bareback for the first time, long and deep, until she flooded his guts with hot cum. He stayed on his back afterward with her leaking out of him while she sucked his cock clean of his own earlier load. They slept tangled together. In the morning she woke him with her mouth and then climbed on top, reverse-cowgirl, so he could watch her tight little hole stretch around his thick cock while she stroked herself to a second orgasm.