First-Time Sissy and the Three Shemales

Damon sat at his kitchen table with the laptop open, the blue glow washing over his lined face. Fifty years old, divorced three years, and the quiet of the apartment had started to feel like a weight. He had never been with a shemale. The thought had lived in the back of his mind for months, a private itch he only scratched late at night. Tonight he opened the dating site again and found Marlene’s profile. Thirty-two, long dark hair in the photos, confident smile, and a blunt line in her bio about loving to dress curious men and show them what her cock could do. His pulse jumped. He typed a short message, honest about his age and his inexperience, and hit send before he could delete it.

She answered within minutes. Her words were direct and warm. She wanted to meet at her apartment, not a bar. She wanted to dress him—stockings, panties, makeup, a wig—and see if he liked being her sissy. Damon stared at the screen, cock already thickening against his thigh. He typed back that he had never done any of it, that the idea made him nervous and hard at the same time, and that he wanted to try if she still wanted him. Marlene replied that consent mattered more than experience. They set the time for Saturday evening. He closed the laptop and sat in the dark, breathing hard, already imagining the feel of silk on his skin.

Saturday he stood outside her door with a bottle of wine he didn’t need. Marlene opened it in a short black robe, bare legs, the outline of her cock visible beneath the fabric. She was taller than he expected, perfume sweet and heavy. “Damon,” she said, smiling. “Come in. We can still stop whenever you want. Say the word and we just talk.” He nodded, throat dry, and stepped inside. The apartment was warm, lamps low, a full-length mirror leaning against one wall. She poured water instead of the wine and they sat on the couch. He told her again, voice shaky, that he had never been dressed, never taken a cock, but the curiosity had been eating at him. Marlene listened, then rested a hand on his knee. “I want to make you pretty and then fuck you until you understand what you’ve been missing. Only if you want that too.” He said yes. The word came out rough and certain.

She led him to the bedroom. Clothes were already laid out: black lace panties, sheer stockings with a lace top, a garter belt, a short pink slip, and a shoulder-length auburn wig on a stand. Makeup lined the dresser—foundation, blush, red lipstick, mascara. “Strip,” she said softly. Damon undressed with clumsy fingers, folding his pants and shirt on a chair. Naked, his cock stood half-hard, average and flushed. Marlene circled him, palms sliding over his chest and the soft give of his stomach. “Good. Now sit.” She worked slowly. First the panties, the lace cupping his cock and balls so the head peeked above the waistband. Then the stockings, rolled up his calves and thighs, the sheer nylon catching the light. The garter straps snapped into place. He watched in the mirror and felt a hot rush low in his belly. The wig settled over his short graying hair, soft and heavy. Marlene turned his face to the light and painted him—smooth foundation, smoky eyes, glossy red mouth. When she finished she stepped back. “Look.”

Damon stared. The man in the mirror was gone. In his place stood a painted sissy with wide eyes and parted lips, cock straining the panties. Heat flooded his face and his groin at once. “I love it,” he whispered. “God, I love how I look.” His voice cracked. Marlene’s robe fell open. Her cock was thick, heavy, already rising, the head dark and shiny. She stroked it once, slow. “On the bed. Hands and knees.” He obeyed, the stockings whispering against each other. She knelt behind him, pulled the panties aside, and slicked two fingers with lube. The first press against his hole made him gasp. She worked him open with patient circles, then slid a slim silicone toy inside, angling until it nudged his prostate. Damon moaned, hips rocking back without thought. “More,” he begged. “Please, Marlene, I need more.” She swapped the toy for a thicker one, fucking him with steady strokes while her free hand reached under to squeeze his trapped cock. Precum soaked the lace. Her own cock throbbed against his thigh, leaving wet streaks. “You’re dripping for it already,” she murmured. “My little sissy slut. Tell me you want my cock.” He did, voice breaking, ass clenching around the toy, whole body shaking with need.

She pulled the toy free, coated her shaft in more lube, and pressed the broad head to his hole. “Breathe.” Damon pushed back. The stretch burned, sharp and huge, stealing his air. He cried out, fingers knotting in the sheets, but he didn’t pull away. Inch by inch she sank in, the pain blooming then shifting as she bottomed out and held still. “Fuck,” he gasped. “So big—hurts—don’t stop.” Marlene drew back and thrust, slow at first, then harder, the thick length dragging over his prostate with every stroke. The burn melted into a deep, electric ache that made his cock jerk and leak. She gripped his hips and fucked him in earnest, balls slapping his lace-covered ass, the wig swaying. Damon sobbed with pleasure, pushing back to meet her. When she angled just right and hammered that spot, the orgasm tore through him without a hand on his cock—white-hot pulses, cum spurting into the panties, his hole clamping rhythmically around her. Marlene groaned, buried deep, and flooded him with her own release, hot spurts he felt inside. They stayed locked together, panting, until she eased out and kissed the small of his back. “You took it so well,” she said. “Come back next week. Dress yourself before you arrive. I have friends who want to meet my new sissy.”

He did. The following Saturday Damon stood in her hallway already transformed—stockings, panties, makeup, the same wig—under a long coat he shed the moment the door closed. Marlene waited in a silk robe, cock half-hard. Beside her stood Mei, twenty-nine, petite with a sharp bob and a sly smile, her own thick cock tenting tiny shorts. Roman, thirty-four, broader through the shoulders, long braided hair, stroked a heavy erection through open jeans and watched Damon with open hunger. All three were unmistakably adult, their cocks large and eager. “Our bitch is here,” Marlene said. Damon dropped to his knees without being told, heart hammering, and nodded. “Use me. Please.”

They did. Mei sat on the couch and pulled his painted mouth onto her cock first, the salty weight sliding over his tongue while Marlene knelt behind him and pushed back into his still-sensitive hole. The double sensation—throat full, ass stretched—made him moan around Mei’s shaft. Roman stepped in, slicked two fingers alongside Marlene’s cock, then worked his own thicker length in beside hers until Damon was split open on both, gasping, tears of effort and pleasure streaking his mascara. They moved in a rough rhythm, one thrusting while the other withdrew, prostate battered until another hands-free orgasm ripped through him, cum striping the carpet. They rotated. Roman took his mouth, deep and steady, while Mei and Marlene took turns pounding his ass, then both at once again, their cocks sliding against each other inside him. Dirty praise spilled from all three—sissy slut, cock-hungry bitch, pretty little hole—and Damon answered with desperate, muffled yeses, pushing back, sucking harder, chasing every thrust. They fucked him on the bed, on the floor, bent over the arm of the couch, spit-roasted until his jaw ached and his hole fluttered open and wet. Three big cocks claimed him over and over—mouth, ass, sometimes both at once—until he came a third time, shaking and empty, prostate singing, body theirs completely.

When they finally finished, spent and streaked with sweat and cum, Damon knelt in the middle of the room, wig askew, lipstick smeared, thighs trembling. He looked up at the three of them and smiled, voice hoarse. “Thank you. I’ll come back every week. I want to be your bitch. I want you to fuck me whenever you want.” Marlene cupped his chin. Mei and Roman nodded, already soft smiles on their faces. He gathered his coat, the cool air of the hallway brushing his stockinged legs as he stepped out. In the elevator he closed his eyes and let the quiet settle over him, already tasting next Saturday on his tongue.