Sunday Afternoon
Keywords: Afternoon, Sunday,
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On Sundays he always wore panties. If he planned on spending the afternoon alone, he'd get out and wear the rest of the clothes – pantyhose, pumps, a skirt, blouse, bra and a slip – but either way – women or men's clothes – he always wore a pair of women's panties on Sunday. It was a little strange, but it aroused him and at the same time, at least he'd tell himself, it gave him a better idea of what women felt like when they were wearing everything society told them they should wear.
This Sunday he chose a pink cotton thong. It barely contained his cock and balls, but it really wasn't made to do that, anyway. It felt nice, he thought as he pulled it on that morning, especially the strap that ran up the crack of his ass.
Laurie watched as Greg pulled on the pink thong. She knew that Greg wore women's underwear, and sometimes dressed completely in women's clothes. He'd told her one night, after a few too many drinks. She didn't normally watch him, but for some reason she was horny that Sunday, and had glanced out the window just as he was starting to dress. His curtains were open more than they should be. Fascinated, and more than a little aroused, she watched as he put on the thong, and then the rest of his clothes. He left. On Sundays, she knew, he liked to go out for breakfast.
She'd met Greg shortly after he moved into the building when she'd bought a new chair and he saw her struggling with it in the elevator. He'd helped her get it into her apartment and over the course of time they'd become friends. They'd even exchanged keys to their apartments, so that if one of them got locked out, they had an easy way to get in. Over the three years they had known each other, they'd gone out a few times, but nothing really had developed.
So, they were friends and neighbors. But Laurie had always thought Greg was pretty good looking, and he'd starred in a few of her fantasies. Greg was six foot, blonde, and kept himself in pretty good shape. She'd been ready to go to bed with him since the first time they met, but it had never happened.
Laurie had always been naturally slim and had taken to wearing her dark brown hair fairly short recently. It was just easier to take care of that way. But she had another reason for wearing her hair short, as well.
While she thought that Greg had never gone out in public dressed as a woman, Laurie did enjoy going out in public dressed as a man. She'd even bought a "packer," a life-like non-erect rubber penis that she could wear so that it would look like she had a cock. About once a month she'd go away for a weekend, checking into a motel in another city. After she checked in she'd strap down her already small breasts (34A) with an ace bandage, change into her men's clothes, comb her hair in a more masculine style, and go out. She didn't do anything stupid like hang out in cheap bars or bad parts of town, but she would go to malls and movies and eat alone in restaurants. If anyone asked her name she'd say Larry. It fascinated her how differently people treated her when she was in her male role. It freed her in some ways. At night she'd go back to her motel, read cheap porn novels and masturbate. She figured that was what most men alone in motel rooms did. When she came, she came hard and long.
But one night she ran into an old girlfriend from high school. And her friend had recognized her. After she got past the embarrassment, they'd ended up back in her friend's hotel room. And things happened, things that, well, that's when Laurie had her first experience with a strap-on. In both roles.
Laurie had wanted to go away that weekend, but a last minute Saturday-morning event at work had stopped her. But dressing and acting like a man was still in her mind. And Greg being in panties put an idea in her head. Today, Laurie decided, she was going to change her relationship with Greg.
The package had come earlier that week. It came in a plain wrapper. It was something she'd wanted for a while, but didn't really know what she was going to do with once she got it, unless she ran into that old friend one weekend. She'd spent too much on it, but sometimes you had to do that, she'd rationalized. After all, it wasn't that strange a thing to have. And it would be interesting to have it on her next weekend trip.
What had come in the package was a strap-on – a dildo and a harness for her to wear so that she could have the equivalent of an erect penis. She'd actually purchased a fairly elaborate one – it not only had a dildo shaped like a penis that hung in front of her, it also had a second place that held another dildo in either her vagina or anus. When she first saw it in the catalog it had intrigued her. When she finally decided to buy it Laurie had told herself that having a penis in front of her really was definitely exciting, but having something inside her at the same time might be a lot more fun.
Anyway, that Sunday morning she'd looked out of her window and seen into Greg's bedroom as he was stepping into the panties. He really needed to know that she could see so much.
Laurie cleaned her apartment up a bit and got things ready. Greg usually got back around 11 and she was watching when he came back into his apartment. Since it was gray and rainy, she'd hoped he planned to stay in and change into his women's clothes. She was in luck – as soon as he came back in he did. He put on a pink bra that kind of matched the thong he was wearing, a white blouse and a blue skirt. She was a little surprised to see him put on some navy blue pumps, but they went with the outfit. The only thing missing was a wig. She had her excuse.
Laurie watched as Greg went into the living room and switched on the TV. He sat down in front of his computer. It was now or never, she thought. Laurie went her room, put on a pair of loose khakis and a man's t-shirt, picked up a blonde wig she had bought a few years ago for a party, and walked out of her apartment. She wasn't wearing a bra, but the t-shirt was loose enough to hide her hardening nipples.
Like most Sundays, no one was around. She went down the stairs and around the corner to Greg's front door. She stood there for a second, took a deep breathe. This was where she had to get things right. If she hesitated, it would be all over and very embarrassing. But, if she was in command, it was going to be a very good afternoon.
Laurie put her key in the lock, turned it, and let herself into Greg's apartment. Quickly she walked into the living room. She saw he was looking at a picture of a woman wearing a strap-on. It was perfect. He turned around, a shocked, scared look on his face.
"It would work much better if you'd wear a wig," Laurie said to Greg, tossing it at him. "You look pretty good in those clothes, but the short hair is a giveaway."
"What are you doing here?" Greg asked. He was beet red, embarrassed, but a little annoyed, too.
"Just like you, I like to change things around a bit sometimes," Laurie replied. "So that's what we're going to do this afternoon. Do as I say and you'll have a good time."
She was a bit surprised at herself. Normally she was far from aggressive. Normally, the game she was going to play this afternoon was about as far from her personality as she could imagine. But she was horny, had a new toy, and had wanted to fuck Greg for two years now. Today was it. Even if it was all turned around.
"Put the wig on."
"What?"
"Put the wig on. We're going out."
"No!" Greg was terrified. Wearing women's clothes around his apartment was one thing. What if someone outside saw him? And recognized him? It was bad enough that Laurie knew.
"Nobody's around," Laurie said. "Just out of here and up to my apartment. Here, let me help."She took the wig and fitted it over his head. Except for the Adam's apple, he could pass. Even his breasts looked real.
"What are you stuffed with?" she asked him, taking him by the hand and leading him to the door. He was a little wobbly on his heels, but he'd make it.
"Umm, they're silicon. They make them for cross-dressers. I just ..." his voice trailed off. How weird was it that an otherwise normal, heterosexual man liked to wear women's clothes and had spent money on prosthetic breasts. What was Laurie thinking, anyway?
They walked out of the apartment, around the corner, and up the stairs. Nobody saw them and they got into Laurie's apartment both a little out of breath.
"Ok," Greg said, still nervous but now a bit curious, too. "What is this all about?"
"You told me you like to dress in women's clothes," Laurie said. "I like to dress as a man. I also want to fuck you. So today I'm going to make you more of a woman, and I'm going to fuck you. Do as you're told and we'll have a good time."
"Yes, ma'am," Greg said. This was not the Laurie he knew. What was next?
"Stay here for a minute. Get on your hands and knees. I'll be right back."
Greg watched as Laurie left the room. She was wearing khaki pants, a white t-shirt and sandals. He could see she wore no bra under the t-shirt. Her hips twitched a little, and he noticed how nice and tight her ass was. He got down on his hands and knees.
Laurie came back a moment later. She pushed his head down into the carpet and flipped his skirt up over his back, exposing his muscular ass.
"Nice," she said. "I'm going to enjoy this."
Gregg felt Laurie flip his skirt up over his back and then pull the band of his thong aside, and her finger, cold with something, probing at his asshole and then entering it.
"Relax!" she demanded. He tried.
Laurie slipped her finger a little deeper into Greg's anus, spreading the lubricant around. She pulled her finger out and quickly replaced it with the nozzle of the enema. Slowly, she squeezed the liquid into him.
"What the!" Greg exclaimed.
"You've got to be nice and clean for me. Keep your head down and hold this in for a little while."
She emptied the enema into him and slowly pulled the nozzle from his ass. It really was a nice ass, she thought.
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Keywords: Afternoon, Sunday,