Community Sissy Ch. 03

The sun shone brightly through the window early Sunday morning bathing the living room in soft light and Sheila was already on her knees. Last night had been a blur of flesh and rhythm and Jenny's voice guiding her through it all. Somewhere between Marcus's third round and Darnell carrying Jenny upstairs, Sheila had stopped thinking of herself as James at all.

A few minutes earlier, Marcus had appeared behind her, barefoot, already hard. He fisted a hand in her soft waves and pulled her head back. "Morning, sissy." His voice was gravelly from sleep. "You slept what, maybe three hours?" as he pushed her to her knees.

She tried to answer but his cock was already at her lips, and her mouth opened on instinct. He fed it to her slowly, watching her eyes water as she took him deep. As she serviced Marcus, she thought to herself how the term cocksucker had a new meaning to her since that first time on Saturday night with her wife and friends watching her. A point of pride rather than an insult. And something that could never be undone. She was a cocksucker and a sissy slut now; for Marcus, for Mike, and for Jenny and Mary. The idea of being a man felt alien and unrealistic as she bobbed on Marcus' cock attempting to please him. Somewhere above, she heard Jenny laugh; a low, possessive sound that vibrated through the floorboards.

"That's it," Marcus murmured. "Breakfast of champions," as he erupted into her willing mouth.

By the time Jenny descended in a silk robe, Sheila's lipstick was smeared and her knees ached. Jenny tilted her chin up, inspected her like a prize mare, and nodded. "You need to call in tomorrow," she said, as if discussing the weather. "Your hair and nails are too pretty for that office. Two weeks vacation."

Sheila's heart stuttered. "Two weeks?"

"You heard me." Jenny's thumb traced her bottom lip, wiping away a strand of spit. "You're going to live as a woman full time. Every day, all day. Dresses, panties, bras, pantyhose, heels, makeup, everything. It's time to begin embracing who you truly are inside."

Sheila thought of her desk, her coworkers, the fluorescent lights of the accounting firm where she'd spent twenty years. Then she thought of the way Marcus's eyes had looked at her last night, like she was something precious and filthy at once.

"Yes," she whispered. "I'll call."

Jenny smiled, slow as honey. "That's my girl."

The day dissolved into a series of vivid, overlapping moments. Darnell took Jenny on the kitchen counter while Sheila knelt beneath them, licking clean whatever dripped. Marcus bent Sheila over the dining table, her painted toes curling against the hardwood as he fucked her from behind, her dress hiked to her waist. Mike and Mary returned Sunday afternoon. Mary was carrying a shopping bag that she presented to Sheila with a shy, wicked smile.

"I got you something," Mary said.

Inside was a French maid uniform. Black, with white lace trim, a white apron, and a zipper at the crotch that locked with a small padlock. Jenny had ordered it, but Mary had picked it up.

"Put it on," Mary said. Her voice was steadier than it had been all weekend.

After quickly touching up her makeup Sheila changed in the downstairs bathroom, her fingers trembling on the tiny buttons. The polyester was cool against her skin. The skirt barely covered her ass. She clipped the black stockings into the garters; Jenny had insisted on real garters and stepped into the black patent heels that added five inches to her height. She looked in the mirror and didn't recognize herself.

She loved it.

When she walked out, Mike's jaw went slack. Mary let out a breath that was almost a laugh. And Mike, traditional, conflicted Mike, crossed the room and pulled the zipper down at his crotch and pushed her to her knees without a word.

"I need this," he said, his voice rough. "I need this so bad."

Sheila took him in her mouth while Mary watched, one hand creeping between her own legs. It was the first time Mike had initiated. It wouldn't be the last.

Monday morning arrived too fast, and Sheila stood in front of the bedroom mirror trying to remember who she'd been a week ago. Her hair fell in soft, salon-perfected waves that brushed her bare shoulders. Her nails were glossy red, filed into perfect almonds. The dress, a navy sheath Jenny had picked out, with a modest neckline that still managed to cling to her hugged her waist, and the pantyhose beneath it felt like a second skin she never wanted to shed.

Her work phone buzzed on the dresser. A reminder: Team meeting, 9 AM.

She picked it up and called HR. Her voice came out softer than she remembered, an octave higher, maybe or maybe she was just hearing herself differently now.

"This is Sheila," she said, then froze. "I mean, this is James. I need to take two weeks. Personal. Family emergency." Sheila's hands were sweating and she could feel her heart pounding as she spoke. On the other end of the phone, the woman from HR acknowledged the request without another thought, oblivious to the slip-up.

When she hung up, Jenny was leaning in the doorway, arms crossed, a satisfied smile curving her lips.

"Good girl," she said. "Now get your heels on. We have a doctor's appointment."

Dr. Harmon's office still smelled the same, like antiseptic and lemon polish and something vaguely floral. Sheila had been coming here since she'd moved to town at age of 22, fresh out of college, nervous and unsure. Now she walked in on four-inch beige pumps, her navy dress swishing around her knees, and the receptionist's eyes went as wide as dinner plates.

"James?" the receptionist said. Then blushed. "I'm sorry--I--"

"Sheila," Jenny said, her hand a warm, grounding pressure at the small of Sheila's back. "Her name is now Sheila."

The receptionist swallowed. "Sheila. Of course. Dr. Harmon will see you in..., just have a seat."

They sat. Sheila crossed her legs, conscious of the pantyhose whispering against the nylon of the chair. She picked up a Vogue magazine from the table beside her chair and tried to focus on an article about fall trends. Her heart was hammering so loud she was sure Jenny could hear it.

A door opened. Dr. Harmon's nurse Denise came out, clipboard in hand, with her curly hair, full figure, and that warm, approachable face Sheila had known for years. Denise looked at her. Then she looked again in obvious surprise.

"James?"

Jenny smiled serenely. "Sheila now."

Denise's gaze traveled down the dress, the legs, stopping at the heels. Her cheeks flushed a deep, telling pink. She looked like she wanted to say something, swallowed it, and gestured toward the exam room. "Right. This way, then."

The exam room was small and cold. Dr. Harmon came in moments later with his silver-hair and warm-eyes, as fatherly as ever. He looked at Sheila over his reading glasses and didn't flinch. Didn't even blink.

"James," he said, his voice calm. "Or, I understand you're going by Sheila now?"

She nodded, her throat tight.

He sat on the rolling stool, folded his hands. "I've known you for twenty years. I've watched you come in here with terrible sinus infections and once with a broken wrist from a skiing accident. I've seen you..." he paused "unhappy. More than unhappy. Like a man wearing clothes that didn't fit."

Sheila's eyes burned.

"You look," Dr. Harmon said, "different. Lighter."

Sheila nodded slowly. She'd thought about it for years, in secret, in the dark, in the shower where no one could see. Now, sitting here in a navy sheath dress with painted nails, it felt inevitable.

Jenny prodded her gently, "go on, tell Dr. Harmon why you're here". I want to start hormones," Sheila said. Her voice didn't waver. "I want to be her. Full time. For real."

Dr. Harmon's smile was gentle and, she could swear, a little proud. "Then let's get you set up."

He walked her through the process. The blood work, the risks, and the timelines. Denise hovered at the door, pretending to update a chart, clearly listening. Her eyes kept drifting to Sheila's legs. Sheila pretended not to notice.

"I'll prescribe a low starting dose," Dr. Harmon said, scribbling on a pad. "Estradiol and spironolactone. You'll get changes gradually. softening skin, some breast growth, redistribution of fat. It's not a switch. It's a slow bloom."

Slow bloom. Sheila tucked the phrase away like a jewel.

He tore off the prescription and handed it to her. His fingers brushed hers; warm, steady, and reassuring. "Welcome to the rest of your life, Sheila."

The pharmacy was fluorescent-bright as Sheila stood in line, clutching the prescription, her heart hammering behind her ribs. The woman in front of her was buying cough syrup. The man behind her was on his phone, oblivious. Normal. All normal.

Then it was her turn.

The pharmacist was new; tall, lean, with dark hair and an intensity that made Sheila's skin prickle. His name tag read Andre. He looked up from the counter, and his eyes did something that made her feel seen in a way that had nothing to do with her prescription.

"Hi," he said smiling. His voice was quiet, warm. "What can I do for you?"

She slid the prescription across the counter. Her red nails caught the light. "I need to get this filled."

He picked it up. Read it. Didn't bat an eye. "Dr. Harmon. Good man." He looked up at her. "First time on these?"

She nodded, mouth dry.

"I'll have it ready in twenty minutes." He paused. His gaze dropped to her hands, then back to her face. "If you want, I can walk you through what to expect. Side effects, timeline, all that. I'm always happy to help."

Something passed between them, a thread, taut and electric. Sheila swallowed.

"That, that would be nice."

Andre smiled. It was a small smile, quiet, like he knew a secret he was willing to share. "Twenty minutes, then."

She was still floating on that when she got home. The bottle of pills was warm in her purse. Real. Hers.

Jenny met her at the door, took the bag, examined the prescription, and nodded approval. Then she tilted her head toward the living room.

"Mike and Mary are here," she said. "They've been waiting."

Sheila's stomach flipped, but not with fear. With anticipation.

Mary was on the couch holding the strap-on she had purchased earlier in the day, 8" long, the realistic looking black penis glowing in the lamplight. The harness contained a special pouch for a bullet vibrator that pressed against her clitoris at the base of the dildo. Mike stood by the fireplace, but his posture was different than Friday night. Relaxed. Expectant. When he saw Sheila in the navy dress, his eyes went dark.

"Uniform's in the wash," Jenny said, waving a hand. "But I think she looks just fine as-is."

Mary set the strap-on down and walked over. She cupped Sheila's face, tilted it up, and kissed her, soft at first, then deeper, a kiss that tasted like grapefruit lip balm and something else. Something newly powerful.

"I thought about the weekend all day," Mary murmured against her lips. "About you. About doing this whenever I want."

Sheila's knees went weak. "You can."

"I know." Mary's hand slid down her waist, down the curve of her hip. "But I want to hear you say it first. Tell me what you are."

The words came easily now. They felt like coming home.

"I'm your sissy. All of yours. I'm the neighborhood slut." She looked up at Mary, then at Mike, then at Jenny who was watching from the doorway, arms crossed, smile approval. "And now, tell us what you're not" Jenny commanded. Sheila paused briefly then replied softly, "I'm not a man, not anymore if I ever really was; I exist to satisfy the sexual needs of real men".

Mary's breath hitched. She turned to her husband. "Mike. Get over here."

He crossed the room in three strides. Mary pushed Sheila to her knees, and Mike's hands were already on his belt. Behind them, Mary picked up the strap-on and began buckling it into place, the leather creaking, a sound that had become as familiar to Sheila as her own heartbeat.

"Two weeks," Mike said, his voice low and rough. He threaded his fingers through the soft waves of her wig. "Two weeks of you like this. Every day." Whatever internal conflict had previously existed about the idea of using his former friend was now long gone.

Sheila looked up at him, at his flushed face, his conflicted eyes that were learning to love this and smiled.

"Maybe longer," she whispered. "I have pills now."

Mike's breath caught. Behind her, Mary stepped close, the silicone shaft brushing against Sheila's cheek. She heard Jenny laugh, low and warm, from the doorway.

"That's my girl," Jenny said. "Now show our friends what a grateful little sissy you are."

Sheila opened her mouth. For Mike. For Mary. For all of them.

It was going to be a beautiful two weeks.