Sunday Afternoon

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Old friends expand their cross-dressing fantasies.
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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. It will be fun to fuck it.

"Now, just let it work a little. Keep your head down and your butt up."

Greg did as he was told. He could see that Laurie was standing just in front of him. He concentrated on keeping his anus closed. He felt really full.

Laurie looked down on Greg. With the wig on, from this angle, he really did look like a big woman. She slipped one foot out of a sandal, and then the other. Well, in for a penny, in for a pound, she thought to herself.

She pulled her t-shirt up over her head and then dropped it on top of the sandals, then slipped her shorts off and added them to the pile.

"Keep your head down!" she ordered Gregg, catching him starting to look up at her.

Gregg put his head back on the floor. The enema rumbled a little inside him. He'd always thought Laurie was cute, but seeing her in her underwear turned him on a bit. She had a small, but really nice body. Now, with his head down, all he could see was the pile of her clothes. It was all he could do not to look up. A small pair of men's jockey shorts dropped in front of his face. The musky smell of an excited woman hit his nose.

Laurie turned and started to leave the room, heading for her bedroom. She turned back and looked at her neighbor as he submissively kneeled on the floor.

"Go to the bathroom and empty yourself. Keep your clothes on. When you're done, come back in here and stand at attention.

Greg got up, straining to hold his anus shut. He saw Laurie walking into the bedroom. She had no tan lines. His cock started to get hard.

Laurie went into her bedroom and closed the door. Her toy box was sitting on her bed, and she opened it. Her new toy was there on top, and she picked it up. Holding the harness in front of her, she stepped into it, spread some lubricant on the smaller dildo and slipped into her vagina. She adjusted the straps so everything was firmly in place. The larger dildo jutted from her crotch, black and menacing and lifelike, right down to the balls. Laurie felt her small, brown nipples harden even more and her pussy contract a little around the dildo inside her.

Greg emptied himself, then got up and washed his hands carefully, dried them, adjusted his clothes and walked back into the living room. His cock was hard, and he could feel its tip pushing out over the waistband of his thong.

He gasped when Laurie walked back into the room – and it wasn't just because of the 8 inch dildo jutting from her crotch. Naked, she wasn't just cute, she was gorgeous. She had an all-over tan and her skin looked soft and smooth. Her breasts were small and perky, capped with slightly darker small brown nipples. They were long and hard. Behind the harness he could see that her pussy was shaved naked. His penis jerked. In her hand was a tube of lubricant, and with the other hand she was smearing it all over the dildo. His ass clenched shut, knowing what was coming.

Laurie was equally pleased with the way Gregg looked. She could see his cock tenting his skirt out a little. The breasts he had chosen were in proportion to his body, so they looked fairly real. He wasn't a pretty woman, but if he shaved closely and put on some makeup he might be able to pass. Her pussy twitched a little. This was going to be fun.

"Get on you hands and knees," she demanded.

Gregg did as he was told.

Laurie looked at her neighbor, then stepped up behind him and knelt between his legs.

"Relax, big guy," she said to Gregg. "This is going to be fun."

She flipped his skirt up over his back and, once again, pulled the strap of his thong to the side.

"Pull yourself open," she commanded.

Gregg reached back behind himself and pulled his ass cheeks open. His face was pressed into the floor.

Laurie put a generous dollop of lube on her finger and pushed it into Gregg's ass, wiggling it around so his sphincters would relax. She knew she could get him to relax his voluntary sphincter, but the involuntary one, just inside his anus, needed a little stimulation. She pulled her finger out, put some more lube onto it and the finger next to it, and pushed them back into Gregg's ass. She felt him relaxing a little bit.

"Ok," she said. "Here I come. Relax. Tell me if it hurts too much and I'll wait."

She carefully positioned the dildo against his anus, shuffled forward a bit, and pushed with her hips, guiding the dildo into him with one hand.

"Oh god," Gregg moaned, feeling the invading dildo push his sphincter open. It burned a little, but it felt good, too.

Laurie pushed in deeper. From her experience with Claire, and, she admitted to herself, a few college boyfriends, she knew that this first bit wasn't too bad. The hard part was coming – getting over the flange around the head of the realistic dildo. It was pretty big. She pushed her hips forward a little more.

The dildo really hurt now, but Gregg was determined not to say anything. It had to feel better soon. If she'd just get it into him all the way. He pushed back a little against her.

At the same moment Laurie was pushing her hips forward again, and suddenly she found herself pressed firmly against Gregg's ass, the dildo buried in him as deeply as it would go.

"Oh fuck, yesss," he hissed. How could this feel so good? He felt full, stretched open, and really, really good.

"Do you really like it?" Laurie asked. She was a little surprised and she wondered if this was the first dildo up Gregg's ass. She even wondered a little if he'd had a cock up there. She'd dropped her dominant act and was concerned.

"Oh god, it's feels good. Fuck me, Laurie, fuck me."

"Ok, Gregg," she said. She pulled her hips back and watched as the dildo slipped back. Just before it pulled out, she reversed direction and pushed back in. The dildo in her pussy moved a little and she became aware of how the harness and the dildos were working together to stimulate her as well.

Slowly they developed a rhythm, Laurie pushing in as Gregg pushed back, both of them pulling apart, and then reversing direction. The dildo inside her squirmed around, stimulating but not satisfying her. Laurie increased her speed.

Faster and faster she pushed into Gregg's ass, trying to find the stimulation she needed to come. She heard Gregg's moans, but they didn't matter. This thing felt good, but her clit wasn't getting enough attention. She pushed harder, burying herself in Gregg's ass, then rubbing around in circles, trying to get the smooth leather of the harness to rub against her clit.

"Oh fuck!" Gregg yelled. "I'm going to come!"

The dildo in his ass was pushing against something (he figured out later it was his prostate) and he could feel himself getting close. His panties were rubbing a little against his cock, but Laurie hadn't touched him, and he hadn't touched himself. But if she would just keep thrusting and squirming a little more...

"Really," Laurie said. "Do you like this?" she asked, pushing hard into him and moving her hips in a circle.

"Oh gee, oh gee, oh gee...huuuh, huuuh, huuuh, huuh, huuh, huuh....COMING!" Gregg grunted. He felt the semen rush up the length of his cock and spurt out of him, soaking his skirt and dripping onto the floor.

Laurie just kept pushing. She was close, but she knew this wasn't going to make her come. Gregg was panting. Ok, she thought to herself, he's good, now it's my turn.

She pulled out of Gregg's ass with a moist noise and stood up. She saw his anus gape open and slowly start to close. Quickly she unstrapped the harness, pulled the dildo from inside her, and let the whole contraption fall to the floor.

"Roll over!" she commanded Gregg. He did as he was told.

Laurie straddled Gregg's chest and lowered herself over him, positioning herself above his face.

"Eat me," she demanded. "Make me cum." And she pushed her pussy down over Gregg's mouth and nose.

Gregg did as he was told. He stuck his tongue out and started licking her pussy, searching for her clit. Laurie was rubbing against him, smearing her musky juices all over his face.

"Lick me, slut!" Laurie demanded. "Make me come, now!"

Gregg licked harder, then pushed his tongue as far as he could into Laurie's vagina. She squirmed around. He could barely breathe.

"My clit, do my clit," she demanded. Her body was on fire. Her nipples ached and she could feel her juices flowing out of her. She didn't get this aroused often, and she new if Gregg would just suck and lick her clitoris she's have a really good orgasm. She pulled and tugged at her nipples, feeling the stimulation rush through her tiny breasts and down to her crotch.

Gregg reached up and grabbed Laurie's butt, holding her still so he could find her clit. Finally he found it – he could feel the hard little nub. He flicked his tongue back and forth over it.

"That's it, that's it," Laurie moaned. "Just like that."

As Gregg flicked and licked and sucked at her clit, Laurie kept tugging on her nipples, pulling and stretching them and her small breasts out from her body, and then letting them snap back into place.

"Hoo, hooo, hooo," Laurie started breathing hard. She was close now. She reached down and grabbed Gregg's hands and pressed them over her breasts. He started massaging them, still licking and sucking her clit.

"Hoo, hoo, hoo, hoo." Her breath came faster and faster. She was really close. Her groin felt heavy and congested and her muscles were tightening.

Gregg sucked Laurie's clit as hard as he could into his mouth, held it taught with his lips, and flicked his tongue, hard, back and forth across it.

"Hoo, hoo, hoo, hoo, HOO, HOO, HOOO! HOOO! HOOO!" Her groin couldn't get any fuller, her muscles any tighter. She was there, she was there, it was coming. "HOOO! HOO! HOOOOOOOOOOOO!!!" Laurie was almost screaming as she came, pushing herself hard down against Gregg's face. Her body shook and trembled. She felt her juices gush out of her with each contraction of her orgasm, flooding down over Gregg. It went on and on, seemingly forever.

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