One Possibility

"Go take a bath, perform your ablutions, and find something sexy to wear," she said.

He was nervous. It was their first time together, in person. Until now their relationship was purely digital. He was a sissy, she accepted this. He felt shame, but then she smiled warmly and spoke a few words.

"It's ok sweet sissy. I know what you are and you know I know. I will never hurt you."

He felt a tingle in his stomach and then kissed her lovingly. She returned the kiss and began undressing him. He went to undress her but she stopped him and continued undressing him until he was naked and she, fully clothed.

"Go get yourself ready," she said. "Let me know when you're ready and we'll paint your face. I'll show you some tips, it will be fun."

He was hard standing in front of her unashamed. He was fully aroused.

He shaved...everything, legs, crotch, underarms, and chest. He looked and felt like a flat-chested girl. He admired his smooth body in the mirror. He bathed, cleaned himself and then picked his outfit. Florida bejeweled sandals, pink spaghetti strap chemise, wide-net hose, pink microfibre/polyester blend thong with an extra-large silky and stretchy pouch. His favorite outfit. He stretched a hairnet over his short hair and put on his dark brown, almost black wig. It was just over the shoulder-length, silky smooth and straight hair. It reminded him of her hair.

He put it up in a ponytail for the makeup.

"Lets go to the vanity, We're all set up and ready," she said.

They talked while she applied makeup. They'd known each other a long time, since before they'd started their digital affair. They were colleagues then, and after he moved away they started writing each other and eventually discovered they had feelings for each other. Because they were both married and he lived on another continent, a digital relationship began and went on for 10 years until now. He'd come back to visit family. He hadn't intended to let her know he was in town. When they ran into each other at Panera they were just going to leave it at that, but then he wrote her. She responded. Then this.

So they caught up. While she painted his face, showing him tricks, demonstrating technique, they talked and before long it was natural. He was aware that he was with his old friend, but also aware that he was a sissy. He was dressed up for her in a way he'd only ever done alone. Fully dressed, wig, and makeup. He watched as she worked magic on his face. He was stunned at how much better she was at makeup than he was. His reflection seamlessly transitioned between man and woman before his own eyes. He felt himself lurch with arousal.

He looked down. A small drop of precum had seeped through the pouch of his thong. She dipped her finger into it and fed him.

"Stroke your clit sissy," she said. "Stroke your clit while we talk and I work on your face."

She was smiling sweetly and she watched him carefully. He pulled out his clit and let the pouch embrace his smooth balls, his pussy they would both refer to it thereafter. He used only the tips of his forefinger and thumb and he stroked his hard clit.

Oh he felt wonderful inside. Complete relief and release. He was sissy now. They continued. She wouldn't let him stop stroking.

"A good sissy knows she must be aroused and consumed by thoughts of masturbation at all times. You are a good sissy right?" she asked.

"Yes, I'm your good sissy," he replied.

"You like masturbating don't you?"

"Yes," he said.

"What do you imagine when you masturbate?"

He thought for a while, he wanted to tell her the truth. He masturbated over many things, fetishes, images, experiences, but he wanted to be specific. He wanted his response to arouse her.

"This," he said. "This right here. You're painting my face, I'm so aroused that I am compelled to masturbate for you. Like I've always wanted, to masturbate with you the way I can only ever do alone."

"Thank you sissy." She kissed him lovingly. "I am thoroughly enjoying our time right now. The more truthful you are with me, the more arousing this becomes. I want to see the you only you know."

He lurched again. She dipped her fingertip into the newly formed dollop of precum and fed him again, this time fucking his mouth as if her fingers were a small cock. "Stroke," she reminded him.

"You love cock," she said. She was still fucking his mouth with her fingers. He was still stroking his clit with his thumb and forefinger.

"Use your other hand and rub your pussy. Slow, deliberate, really find your spot down there and push on it."

He began rubbing his pussy. He called his balls and perineum his pussy. It was, he imagined just like a pussy. His started at the perineum all the way up his balls to the base of his shaft. That area he used like a pussy. His smooth balls were like labia and his perineum was like a g-spot. He'd trace his fingertips along his labia and feel the tingling sensation all the way up his spine. He wiggled two fingers between his balls and push on the root of his hard clit through the silky material of his thong rubbing it up and down the way he'd seen women masturbate. Then he'd get to his perineum and grind against it pushing his hips toward his fingers with urgency, feeling just like the women he'd seen.

She knew he did this from his stories and letters, but she watched in fascination at how he imagined a woman masturbated. She watched his eyes closed as his facial expression, timed to the movements of his fingers, reflected the movement and intent of his actions. He looked like he was enjoying it.

"Stop stroking," she said. "But continue playing with your pussy. Show me how good you can make your pussy feel. Only feel your fingers there, nowhere else, concentrate your pleasure only on your pussy. No stroking, only jilling." She laughed when she said "jilling" and so did he. His laughter was one of total release and acceptance.

"Jill your pussy sissy," she added. "Slap yourself there. Lightly, but squarely. I want to see you make those little jumps I've seen in your videos."

He spread his legs and scooted forward so he was sitting on the front edge of the chair and slapped his pussy, He lurched at the suddenness, and his subsequent slaps grew sharper and more precisely placed, whipped him into a frenzied state. He was rubbing his pussy along the root and slapping his balls and he grabbed her hand and brought it to his mouth and she knew what to do. She began fucking his mouth again with her cock.

"Suck my cock sissy," she said. "You love sucking cock huh sissy...no, no, don't speak, just enjoy my cock, feel how hard it is in your mouth, show me how much you love sucking it."

She marveled at him. He looked so much like a woman, but like him, when she looked at him, his sissy and man image shifted seamlessly back and forth. She caressed his cheek and stroked his throat up and down to encourage him.

"Cock is good for you," she said. "You love sucking cock and eating cum. Do you want to eat your cum for me tonight? Nod if you agree. Good, where do you want it? No, I think I'll decide that. I love watching you sissy. Your face looks lovely, keep your eyes closed and let yourself go."

She took her cock away and he started to calm down instinctively. He sat back in his chair and relaxed.

They finished the makeup and they kissed.

"I know you've never mentioned it before," he began. "But for me, it feels like I'm seducing you into lesbian sex." They both laughed.

"Think of it like this," he said. "I am a woman. I'm a sissy to me, a sissy to you, but you are a woman. You are engaged in sexual activities with what I imagine is a woman, so you are behaving like a lesbian."

She thought about it. Lesbian experimentation is widely known as one of the most common fantasies "straight" woman have. She never really thought of it, and when she tried it never went anywhere in her mind. Now she looked at him and suddenly the woman remained, she hardly recognized her long-time man friend.

"Stand up," she said. "Do a dance for me. Wait, go put on some heels."

He came back with 3 inch Ralph Lauren leather sandals. He danced for her. He walked around the room swinging his hips and posing.

"Lie down on the bed and pose for me." She got out the webcam and set it up on the tripod with the bed center frame. He posed on the bed, legs together, crossed at the ankles, and sticking straight up into the air as he lay on his back. His long smooth legs encased in spiderweb hose, plus the shoes, he looked like a porn actress.

"Show the camera your pussy," she said. She activated their live account and started recording.

He rolled onto his stomach and pushed his chest down on the bed, arched his back, and stuck his ass into the air.

"Slap your asshole sissy," she said. "Show me sissy, be my sissy and show me."

He did.

She went to her nightstand and squeezed a dollop of lube onto his ass and balls. "No touching your clit," she added. "Only your pussy and asshole. Fuck your asshole for me." Then she tossed a vibrator onto the bed.