Community Sissy Ch. 04

The next 2 weeks bled together in haze of indoctrination, use and submission.

Monday: Mary's text at 8 AM. Come over. Mike just left for work. Sheila was at their house by 8:45, the French maid uniform under a trench coat, her heels clicking on the welcome mat. Mary opened the door in a silk robe, the strap-on already buckled.

Tuesday: Mike called at Noon. Lunch break. I need you. She met him in the parking garage attached to his office, her skirt bunched around her waist while he fucked her with a frantic, guilty urgency. She drove home leaking cum all over the leather seats in her car.

Wednesday: Mary again, but this time with a riding crop she'd bought online. "Bend over the kitchen table," she said, and her voice held no tremor now. Sheila's ass was striped pink by the time Mary was done, and she came twice on the strap-on while Mary's fingers worked her clit.

Thursday: Mike and Mary together, a double session. Mary fucked her from behind while Mike knelt in front of her, feeding her his cock. The symmetry of it, mouth and cunt both full, unspooled something in Sheila's brain that she didn't want to retrieve.

Friday: Marcus appeared at the house without warning. Jenny was out with Darnell. Marcus found Sheila in the kitchen, still in her robe, and bent her over the counter without a word. The granite was cold against her cheek. His hands were on her hips, and he took her right there, the slap of his thighs against hers the only sound for long minutes.

Saturday and Sunday blurred into a loop of sex and sleep and the constant hum of pantyhose against her thighs. Jenny had ordered a dozen pairs--nude, black, suntan, even a pale pink. "Wear them under everything," she'd said, handing Sheila a shopping bag. "Jeans, slacks, suits. Even to work. Especially to work."

By the end of the first week, Sheila had learned to carry condoms in her purse for those times when she hadn't prepped with an anal douche. She now carried her own little mini sex kit. Magnum for Marcus, Skyn Elite for Mike, lube and a maxi pad for whenever they took her raw. She kept a similar setup at the house in her nightstand. "Quite the little sissy slut, aren't you?" Jenny had teased with a smile when she saw Sheila loading the contents into her purse before leaving to meet Mike at his work one day.

And now the two weeks were over.

Monday morning. Fluorescent lights. The smell of stale coffee and printer toner.

Sheila, no, James stood in front of the bathroom mirror at the accounting firm, staring at his reflection. Navy suit. White shirt. Tie loosened slightly. Hair was cut short again, a concession to the office, but the sideburns were gone and the shape of his eyebrows had been arched at the salon into a permanent question mark.

Two tiny gold studs sat in each ear. One was maybe OK, but two screamed femininity in his mind as he stared at himself in the mirror, especially when you combined them with the brows. But, there was no hiding them. He'd tried to remove them, but Jenny had locked the backs on. "Leave them. People will assume you had a midlife crisis."

Under the suit: a beige camisole, smoothing his chest. Under the trousers: nude pantyhose, the waistband hidden by his shirt, the toes compressed into his leather oxfords. He felt the nylon slide against his thighs with every step, a constant reminder of the sissy he was inside.

His desk was exactly as he'd left it. Rick from accounting, two cubicles over, looked up when James sat down. "Hey, man. You look different. Did you lose weight?"

"Something like that," James said. His voice came out higher. He cleared his throat.

Rick's eyes lingered on James's ears. "You get your ears pierced? Kinda radical for you; you always seemed so buttoned up and stiff, no offense. "

"Yeah. Jenny convinced me that I needed to lighten up and try something new." James replied as he quickly walked into his office ending the conversation.

The morning crawled. Every time he stood, the pantyhose whispered against his trousers. Every time he crossed his legs, the nylon stretched and pulled, a ghost of sensation between his thighs. He felt exposed, hyper visible, and yet no one said anything beyond the comment about his ear piercings.

At lunch James was in the break room, microwaving a sad bowl of soup, when his phone vibrated. A text from Mary: Come to the House. Now.

His heart stopped. Then restarted at double speed.

Rick walked into the breakroom and stopped looking at the expression on James's face. "You okay?" he asked.

"Fine. Just some family stuff." James grabbed his soup out of the microwave, replaced the lid and shoved it back into the fridge. "I need to take a long lunch. Can you cover for me?"

Rick shrugged. "Sure." As James hurried away, Rick couldn't help but notice the way James's hips moved as he walked away, the slight sway in the way he walked that didn't remember and that in truth hadn't been there two weeks ago.

James rushed home in a daze, the sixty-minute window ticking in his skull. The routine was second nature now: douche, shower, shave every inch, moisturize, apply foundation and mascara, brush on the soft pink lipstick. He wore the navy sheath dress; the same one from the first date night. The pearl pumps. The nude pantyhose that were already on. He was ready in forty-three minutes.

Mary's house was a ten-minute drive. She opened the door in yoga pants and a tank top, no bra, her hair in a messy bun. "Good girl," she said, pulling him inside. "Mike's at work. We have the whole afternoon." The strap-on was already on the coffee table. A new one that was more lifelike. It was bigger, black, with veins molded into the silicone. Mary picked it up and handed it to him. "Put it on me."

Sheila's fingers trembled as she buckled the harness around Mary's hips. The leather was soft, well-oiled. She adjusted the straps, cinched them tight, and Mary let out a pleased hum.

"On the floor," Mary said. "Face down." Sheila obeyed. The rug smelled like carpet cleaner and something floral. Mary knelt behind her, squirted a bit of lube onto the toy at her entrance, and pushed.

The stretch was immediate. The new toy was thicker, longer, and Mary had learned to thrust with her hips now, not just her pelvis. She drove it deep, held it, then began a steady, punishing rhythm as the bullet vibrator worked its magic on her clitoris.

"You take cock in your ass like a whore, little sissy bitch. Not really an ass, I guess we should refer to it as your pussy" Mary panted as she thrust.

"Yes," Sheila gasped. "I - I think about it. When I'm at work. I think about you fucking me."

Mary's hand snaked around, found Sheila's clit. "You think about this?"

"Yes."

"You think about Mike?"

"Yes."

"You think about Marcus?"

Sheila's hips bucked. "Yes. All of you. Every day."

Mary's fingers pressed harder, her rhythm on the strap-on increasing. "You're our sissy. Our slut. You're nothing but a hole for us to use. Can't believe you pretended to be a man for so long."

Sheila's orgasm crested, surprising her, a sharp cry tearing from her throat. Mary didn't stop. She fucked her through it, kept going, and Sheila felt a second peak building before the first had fully subsided. "That's it," Mary crooned. "Give me another one. Give me everything."

James made it back to the office just before 3pm. Her makeup was gone, her hair combed back to a male style, the suit back in place. But the pantyhose were damp, a secret that he carried between his legs like a talisman.

Rick was at his desk. He looked up as James passed. "Everything okay?"

"Fine," James said. His voice was a little hoarse. "Just had to help one of our neighbors with something."

James sat down. Opened the computer. The screen glowed as he got ready to resume his work. A few minutes later, the phone buzzed again. A text from Marcus: Tonight. 8 PM. Be ready. Sheila typed back: Yes and even added a little heart emoji.

The grandfather clock in the hallway chimed 8pm, and Sheila was already on her knees by the door.

The French maid uniform had become her second skin over the past week; black polyester, white lace trim, the apron stiff with starch. The padlock at her crotch pressed cool against her skin, a reminder that she was sealed, contained, and owned. Jenny had left an hour ago with Darnell, murmuring something about a late dinner and a hotel room, and the house had settled into a waiting silence.

Headlights swept across the front window as Marcus turned into the driveway.

She heard his footsteps on the porch; unhurried, deliberate. The door opened without a knock; he'd stopped bothering weeks ago. He filled the frame for a moment, backlit by the porch light: lean, athletic, that sharp jawline cutting shadows. He was wearing a suit jacket over an open-collared shirt, and he looked like he'd just come from a boardroom.

"You still have that on," he said, eyeing the uniform. "Good."

She stayed on her knees as he walked past her into the living room. He loosened his tie, tossed it over the back of a chair, and poured himself two fingers of Henessey XO from the decanter. Jenny had made sure that the entire bar was now stocked with drinks preferred by Darnell and the men who came to use her sissy. Anything James used to drink was long gone.

"The McKesson property on Fourth came through," he said, settling into the armchair. "Closing's Friday. Twenty-seven units." Sheila tilted her head, uncertain whether he wanted a response. He wasn't looking at her. He was swirling the cognac, watching the amber liquid climb the glass walls.

"The first property I bought outright was a duplex in Rotterdam," he said. "Three bedrooms, a yard the size of a postage stamp. I'd just torn my ACL playing for the second division in Spain, and I had a settlement check burning a hole in my pocket. Everyone thought I was crazy for buying property in a country where I could barely ask for a glass of water."

Sheila's lips parted. It was the most he'd ever told her about himself. "You played professional basketball," she said softly.

"For seven years." He finally looked at her, and that intensity was back, dark and focused. "Darnell and I both got recruited out of the same high school. He was the point guard. I played small forward. He went pre-med, after college and my scholarship, I went to the European leagues and spent a decade bouncing around Madrid, Milan, and other places."

She couldn't picture it; him on a court, sweaty, competitive, surrounded by roaring crowds. The man in front of her was so controlled, every movement measured. Athletic grace, she realized. "After I retired, I came home and bought a hundred units in two years," he finished. "Now I manage six hundred. Turns out watching film for a decade teaches you something about anticipating what people need before they ask."

The front door opened. Darnell's voice filled the hallway before his body appeared: "Man, you telling war stories without me?"

Marcus raised his glass. "Just the origin story."

Darnell walked in, broad and unhurried, shrugging off a cashmere coat. Behind him, Jenny appeared; her lipstick looked like it has been freshly reapplied, her dress clinging to every curve. She looked like she'd been thoroughly fucked, and she smiled exactly the way a cat smiles at a bird with a broken wing.

"Jenny couldn't stay away," Darnell said, settling onto the couch with an ease that made the leather sigh. "Said she wanted to watch."

"I always want to watch," Jenny corrected, draping herself over his lap. She was wearing a burgundy wrap dress, and when she crossed her legs, she wasn't wearing anything underneath. "But Darnell was telling me about his day. Tell her, baby. She should know what my bull does when he's not wrecking her wife."

Darnell's hand slid up Jenny's thigh, unhurried. "I'm an OB-GYN. Been in practice for fifteen years now. You know that." Sheila nodded. She did know. Jenny had mentioned it back when the arrangement was still new, raw, a secret she'd carried for years before finally acting on it. But hearing it again, here, in this context, felt different. A doctor. Her wife's bull was a doctor.

Jenny was watching him like he'd hung the moon. Sheila felt something twist in her chest; envy and heat, tangled together. "You were a nurse, Jenny," Sheila said.

"I was." Jenny's eyes slid to her. "We had already started our arrangement a couple of years earlier. I knew Darnell by reputation before we ever hooked up. The whole hospital did. Nurses talk. The women he dates talk. He's got this, this presence. This way of walking into a room that makes everybody look up." She ran a hand along his chest. " I spent four years building up the courage to finally walk into his office and ask him out. Four years of watching him from across the nurses' station, wondering what he'd be like in bed."

"And?" Sheila heard herself ask.

"And he's exactly what I imagined." Jenny's smile was slow. "Better. Every single thing I imagined, he delivers. Every time." Darnell caught her chin and kissed her, thorough and unhurried. When they broke apart, Jenny was breathing harder, her pupils blown wide in anticipation of what was yet to come.

"Stand up," Marcus said. It took Sheila a moment to realize he was talking to her. She rose from her knees, the uniform skirt barely grazing the tops of her thighs, the padlock swinging gently.

"Turn around. Slow."

She obeyed. She'd learned to obey. The dress had no back, just a deep cut that showed her spine, the waistline of the pantyhose Jenny had made her wear beneath. Wolford Fatal Neon 40 in Nearly Black. A gift for special occasions she had said.

"That's a good look for her," Darnell observed. "The maid uniform suits her better than the men's clothes ever did."

"You think?" Marcus set down his glass of cognac.

"I think she's got a purpose now. Every woman needs a purpose."

Jenny laughed. "She's not a woman, baby. She's something else entirely."

"Something better," Marcus agreed. He stood and crossed to Sheila, his hand finding the zipper at the back of her uniform. The sound of it descending was loud in the quiet room. He pulled the fabric off her shoulders, let it fall to the floor in a whisper of polyester.

She stood in nothing but the black hose, thong panties and her bra, the outline of the padlock at her crotch visible under thong. The key had been hanging from Jenny's wrist all evening.

"Thank you for telling me about yourself," she said quickly, turning to face him. "I didn't know you played basketball. I didn't know about the property company." She swallowed. "I want to know everything. I want to know everything about both of you."

Marcus regarded her for a long moment. Then he stepped closer, his hand cupping her jaw, tilting her face up. "You want to know everything?"

"Yes."

"Then get on your knees and show me how grateful you are that I'm here at all. That any of us are." She dropped to the floor instantly. The hardwood was cold against her knees. Her hands went to his belt automatically, unbuckling it, unzipping him. She took his cock out of his pants with care. It was already hardening, the head a deep plum color and her mouth opened without a moment's hesitation.

"Look at her," Darnell said, amusement warming his voice. "She's been missing you all week."

Marcus's hand fisted in her hair. "You're a greedy little sissy. Aren't you?"

Sheila couldn't answer around him. She nodded instead, bobbing her head, tasting salt and skin. From somewhere behind her she heard Darnell's zipper, and then Jenny's voice, sharp with anticipation: "She's not the only greedy little slut here. I need this cock back in my pussy." Marcus glanced over at Darnell as the two former teammates once again paired up to fuck a pair of sluts all night long.

The doctors' appointment was the next morning. Sheila told work she would be late. Her blood work had come back clean. Denise was on vacation, so it was just the nurse practitioner's assistant. Sheila waited in the exam room in her navy sheath dress, heels, a fresh application of lipstick.

She had an hour until she needed to be at Mike and Mary's for her Wednesday afternoon session. That thought made her smile. Then guilty, then warm again. Dr. Harmon came in with her chart. The silver-haired doctor sat on his stool, his expression warming as he read her hormone levels.

"Sheila." He used her name easily now. "Your estrogen levels look excellent. Any side effects I should know about?"

Her hand drifted unconsciously to her chest in a small, protective gesture that he caught. "My nipples are getting more sensitive," she admitted. "And my skin's changed. Softer. And I don't know how to explain this, but my sense of smell is different."

Dr. Harmon made a note. "All normal." He set down his chart. "I want to discuss something that came up in your last visit. One of the things you mentioned in your intake was about the emotional shifts you're experiencing. You said that you feel more at peace than ever before, but also more anxious in public. That's not unusual. This is a big transition."

Sheila nodded. "I have good days and bad days. The good days are getting more frequent." She paused. "Yes. The bad days aren't about wanting to stop. They're about feeling like I'm moving too slow."

Dr. Harmon smiled. "That's the most honest thing you've said yet." He made another note, then looked up. "I'm going to increase your estrogen. And I want to recommend a few additional steps; nothing medical yet. But you mentioned you were interested in exploring voice therapy, and more permanent hair removal."

Her heart stuttered. "Yes. Both."

"I'll have my office send referrals." He stood, extending a hand. "You're doing beautifully, Sheila. This process; it's a blooming. And you're right on schedule."