Caught Wearing a Bra! Pt. 04

Mike walked into his house wondering what Sandra was doing. Had her friend arrived at her place yet? Maybe they were having a relaxing drink before they went to the bedroom. Would they have dinner before, or have sex, then eat something, then go back to the bedroom? Maybe he would leave after dinner and Sandra would text him to come over.

He went to the kitchen and looked through his refrigerator, but found nothing he wanted to eat. He poured himself a glass of wine and wandered to his bedroom to change clothes. He started looking at his dresses and skirts to decide what he would wear for his dinner date with Joe. He only had four dresses and three skirts, so the decision wouldn't be too hard.

He was almost sorry he'd agreed to the dinner date with Joe. He felt like he was betraying Sandra. But why did he feel that way? He'd been honest with her about his sexuality. And she knew he'd done something with Joe earlier in the day.

And, besides, she was probably naked and rolling around in her bed with 'The Liquor Guy'. Mike didn't know his name. Did that make Sandra a whore if she had sex with The Liquor Guy so that he would keep her liquor cabinet stocked? What if she didn't need any liquor so he offered her the money the liquor would have cost? Would that make her a hooker?

Mike imagined them naked in Sandra's girly bed. Her boyish body, his...Mike realized he didn't have a clue what TLG looked like. He pictured him as young and fit, stocky, with a moderately hairy body. And, of course, in Mike's imagination, TLG had a long, thick dick with a big round mushroom head that would stretch her pussy out so that she wouldn't even feel his dick in her anymore. Maybe she'd at least let him pleasure her with his mouth after TLG was done with her.

He laughed at himself as he started to pull the dresses out of his closet. She'd been with TLG before she had sex with Mike, and she'd said Mike's dick was just the right size.

He tried on each of his dresses, complete with the heels he'd wear with them. He stood in front of the full length mirror, turning this way and that, looking at how they fit him and how his ass looked and how his legs looked. He didn't really like any of them for his date with Joe.

He went to the kitchen to refill his wine glass and started on the skirts and blouses. He tried on different combinations, and still didn't find the look he was wanting.

"Maybe Sandra will go shopping with me and help me find something I like," he said aloud. He put his small silicone forms in the cups of Sandra's bra and changed back into his favorite 'around the house' dress- a simple dress that looked like a long tank top. It was a light turquoise that reached to just above his knees. He put his light blue ballet slipper style house slippers on and went back to the kitchen.

He sat at his small kitchen table sipping his wine and thinking about what he wanted to eat. He looked at his phone. Should he? He thought about last night and smiled. He picked up the phone and called the same pizza place. Maybe he'd get the same delivery driver.

While he waited for the delivery he rinsed his wine glass and put it on the dry towel, then got a tumbler and reached for the vodka in the cabinet. He took his vodka/ginger ale to the bedroom to put on his wig and some make-up.

He sat back at the table with butterflies in his stomach waiting for the doorbell to ring. He wished he could call Sandra and tell her what he was doing... or was going to do. That made him again think about what she might be doing. Was she naked? Was she still wearing his hose, panties and bra? Was that just a tinge of jealousy he felt?

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Sandra tried to not cringe when Jason (TLG) roughly rubbed her right breast while he grabbed her left butt cheek with his left hand. He kissed her on the neck, rubbing his rough five-o'clock shadow against her soft skin.

She thought about Mike's gentle touch and wished she could give Jason some pointers on how to touch her.

"You want to hear something sexy?" she asked softly.

"Sure, baby," Jason said as he moved his hand down to rub her panty and hose covered pussy.

"Do you like my panties and bra today?" she asked.

"Yeah, baby, they're sexy. Like always. Feels like you've already had a good cum in them, though," he said as he moved his mouth to hers.

"Mmmm, what makes you say that?" she asked him.

"They're kind of stiff and crusty feeling," he said. "What did you do, take care of yourself as soon as you got home today? Or maybe you did it in the ladies room at work?" He grinned. That was a recurring fantasy of his that she might masturbate in the ladies room at work. He pushed his mouth hard against hers and shoved his tongue in her mouth as he rubbed harder on her pussy.

She had her arm wrapped around his neck. She managed to move her mouth away from his to kiss him on the ear. She was confused about what she was feeling. She usually loved how Jason was kind of rough with her. She usually liked the feeling that he was taking her, not that she was giving herself to him. She usually liked that there was no pretense of making love or tenderness. But tonight his kisses were not turning her on, and she felt like he was pawing her, not caressing her.

"They're not mine," she whispered to him. "They belong to a friend of mine who wore them all day yesterday, then came over here after work."

Jason pulled back from her. "Your friend wore these panties and bra all day yesterday and you wore them all day today? You usually want to change panties before we go to bed when I stay over."

Sandra laughed. "That's true. But we were fooling around and this morning thought it would be sexy if we traded underwear. It's kind of kept me turned on all day," she smiled.

Jason grinned. "That's kind of kinky!" he said. "I thought you felt extra damp down there tonight." He rubbed his fingers hard on the crotch of her panties and hose, right over her hole. "So did you make your friend cum in these last night before she took them off?" he asked. Sandra could tell he was getting excited thinking about it. He'd often tried to get her to talk about being with other women.

She smiled and nodded. "Yes, I made him cum in them before I took them off of him."

"Mmmm, so sexy!" Jason moaned. Then he realize what she had just said and jerked his hand away from her crotch. "Him?"

"Yes," Sandra said in a sultry, sexy voice. She reached down to rub his hard dick. "He's a friend of mine who likes to wear panties and bras and hose. He wore mine from yesterday to his work today."

"So that's man cum I've been rubbing on down there?" Jason asked, pulling more away from her.

"Well, some," she admitted. "Some of it's mine, too."

Jason rubbed his hand on his underwear, as if to wipe Mike's dried cum off of it. "Well, take them off," he said. "I don't want to rub on man-cum."

Sandra knelt in front of him and hooked her fingers in the waist band of his jockey briefs. She leaned forward as she pulled them down and licked up and down his still hard dick. She took his bulbous head in her mouth while she worked his underwear off of his feet, leaving him naked. She put her hands on his hips and bobbed her head up and down on his shaft a few times before she let him slip from her mouth and stood back up.

"You know what would be really sexy," she purred as she put her lips against his. She flicked her tongue against his lips and teeth. Her hand were still on his hips. She pulled him against her, rubbing her nylon covered pubis against his hard dick. "What would be really sexy is if you lay on top of me and rub your dick on his hose and cum on them," she whispered. "Then I'll give them back to him and make him wear them with your cum on them."

Jason tried to pull away. "No, baby," he said. "Come on, let's just get naked and fuck. Please?"

Sandra sighed and pushed the hose and panties down her legs. She lay on the bed and spread her legs as Jason rolled on top of her.

She suddenly realized why she wasn't enjoying her time with Jason as much as she usually did. She felt like she was betraying Mike. Why? All they had done was spend a very enjoyable evening and night together. They hadn't made any promises to each other. They hadn't talked about being exclusive with each other. But she had so enjoyed her time with Mike that she didn't want to do anything to jeopardize what she felt like was the start of something good.

She pulled Jason's mouth to hers and shoved her tongue against his as she pumped her pussy up to meet his thrusts. She was surprised that she was thinking about Mike while her legs were wrapped around Jason. She wondered what he was doing, how he was dressed, if he was thinking about her and what she might be doing.

*********************************

A chill shot up Mike's spine when he heard the doorbell. Too late to change his mind now! He drank the last of the vodka/ginger ale in his tumbler and went to answer the door. He tried to smile as he pulled the door open.

It wasn't the same delivery guy. This time it was a late teen/early twenties girl. She looked down at the ticket as she heard the door open. "All meat pizza for Michelle?" As she said it she looked up at Mike's face.

"Yes," Mike said as he took the pizza box out of her hand and handed her some money. "Thank you. I don't need any change."

She smiled at him as she took the money and shoved it in the pocket of her apron. "Thank you, sir... uh, ma'am."

Mike returned her smile. He walked back to the table on lighter feet. He'd done it! He answered the door and faced someone as Michelle! And they didn't laugh or make snide remarks! Never mind that she was probably laughing when she got in her car, and that she would go back to the store and tell them all about the weird guy in a dress she just delivered to. Mike didn't think about all that.

He wanted to call Sandra and tell her. But he knew he couldn't. She was busy.

*********************************

Jason rolled off of Sandra and got out of bed. "I'm gonna take a quick shower," he said.

"Sure. Go ahead," she said, not hiding how she felt.

"You going to join me?" he asked. "I can put my magic fingers to work."

"Not tonight," she said. She waited until he went into the bathroom to roll over and get her phone to send Mike a text. 'Jason's taking a quick shower, then he's going to leave. Still want to come over?'

Mike was sitting at his table looking at dresses online. 'Of course I do,' he answered her.

Sandra: 'I'm all sweaty and have his cum in me. Do you want me to get in the shower after he leaves?'

Mike: 'NO!'

Sandra: 'lol you're funny'

Mike: 'I ordered a pizza again and answered the door as Michelle'

Sandra: 'Oh? Did it go okay?'

Mike: 'Yes. Delivery driver was a young lady. She called me ma'am!  '

Sandra: 'nice! Are you still dressed as michelle?'

Mike: 'yes'

Sandra: 'will you come over here as michelle?'

Mike: 'yes'

Sandra: 'great! Jason is getting out of the shower. I'll text you when he's gone.'

Jason came out of the bathroom still drying his naked body. He sat on the edge of the bed to put his underwear and socks on. "I'm not sure what I did wrong, but I'm sorry," he said.

Sandra smiled and laughed just a little. She reached out and touched his arm. "You didn't do anything wrong, baby," she said. "I'm just not in a very good mood tonight. It'll be better next time you come over."

He pulled his pants on, then pulled his shirt over his head and leaned over to give her a kiss. "Ok, baby. I'm gonna hold you to that."

She put her hand on the back of his head and opened her mouth to kiss him. "I promise," she said as he stood up. She didn't get up to walk him to the door. She listened to him put on his shoes and go quietly out the door. When she saw his headlights flash across her window she knew he was gone.

Sandra to Mike: 'Come on over. Just come on in. The door will be unlocked.'

She lay back in the bed languidly rubbing her still swollen clit with one hand while she used the other hand to pictures of men in lingerie on her phone.

Mike quickly cleaned up his pizza mess, then went to the bathroom to brush his teeth. He did that for two reasons- he wanted them to be clean when he kissed Sandra, and on the off chance he got stopped on the way to her house he didn't want to smell like wine or vodka.

He changed into a pair of black pumps with 2" heels, put his license, credit card and some money in a small purse, and he was ready to go.

He stood at the door for a long minute, listening for any noise outside. It was still early on a Friday evening, so there was a chance one of his neighbors might be outside. He'd never left this house dressed as Michelle before. Finally he opened the door and stepped out onto his porch. The motion detecting light came on, bathing the porch in yellow light! "Shit!" Mike said aloud as he reached back in the door to turn the light switch off.

He looked around and listened. He didn't see or hear anyone. Hopefully all of his neighbors were either gone for the evening or already settling in front of the tv. He hurried to his car and quickly backed out into the street. Once away from his driveway he relaxed in the knowledge that if anyone saw him they'd just see a young woman going out on a Friday night.

Minutes later he let himself into Sandra's house and locked the door. He walked to the bedroom, unsure how she would greet him. He stopped short when he saw her. She was propped up on her pillows facing the bedroom door. Her feet were pulled up so her knees fell apart to totally expose her well used pussy. With her left hand she was caressing her right breast and pinching her nipple; with her right hand she was gently rubbing her still wet pussy lips.

She looked at him and smiled. "Hey, pretty girl, you like what you see?" she asked in a sultry voice.

Mike smiled and shook his head. "No. I love what I see," he said. "You are so beautiful and sexy!"

Sandra giggled. "Aww, thank you baby. I could say the same thing about you!"

Mike posed and turned to the side to model his dress. "You like?"

Sandra sat up, the moved to her hands and knees and crawled to the end of the bed near him. "Very pretty," she said. "I may want to borrow that to wear to work one day."

"Oh, Sandra, that would be so hot for you to wear my dress to work!" Mike said.

"Mmmm, can I borrow your lingerie and heels, too?" she asked sexily.

"Honey, you can borrow anything of mine you want," he told her.

"And that goes for you, too," she told him. "If you ever want to wear something of mine all you have to do is ask." She crawled off of the bed and stood in front of him. "But right now I think I want you to be naked," she whispered before she pushed her tongue into his mouth. Mike opened his mouth to accept her tongue. He felt her grab his dress at the waist and start to pull it up his body. He raised his arms when she broke the kiss to pull the dress over his head.

"Oh, you have some little cheaters, too!" she giggled when she saw his silicone forms in her sheer bra. She put both hands on them and squeezed. "They feel so real!"

"Mmmm, to you," he said. "But it feels better to me without them."

Sandra reached around him to unhook the bra. Mike leaned forward and let the form-filled cups fall into her hands. She took the bra off of his arms and put it on the dresser. Then she knelt in front of him. She put her hands on his hips and pulled him to her so she could run her tongue across his panty covered cock.

"Somebody's been leaking," she giggled as she licked a wet spot near the tip of his cock. She hooked her fingers in the waistband of his hose and panties and pulled them down his legs. She kissed his pubic bone, his thighs right at the crease where his pubic area started. She pushed the panties and hose down around his calves, then put her arms around him. As she took his small hard cock in her mouth she reached around and ran the fingertips of both hands up and down his back crack.

"Not too much of that, baby," Mike gasped. "I won't last long."

She pulled her head back and looked up at him. "I want it now," she said in a deep, sultry voice.

"You want me to cum now?" he asked. He'd really hoped to wait a while, but he was so close he knew if she kept on it would happen.

"Yes, I want your cum now," she told him, her voice muffled by his cock in her mouth. Mike put his hands on her head and pumped his dick in and out of her mouth. Sandra knew it was going to happen and started to swallow. Mike's shaft throbbed and sent spurt after spurt of thick cream into her mouth and down her throat. Sandra swallowed it all and kept sucking until Mike relaxed. She pulled her head back and let his dick slip from her mouth. She leaned over and helped him out of his heels, then finished taking the hose and panties off of him.

"I want to lay back down and I want you to eat my pussy and make me cum now," she whispered as she pushed her tongue into his mouth. He could taste the tangy cum on her tongue. Mike turned them around and let her fall back on the bed. He fell to his knees beside the bed and wrapped his arms around her skinny thighs.

He could smell her sex. He could smell Jason's cum. He could smell her sweat and piss and the juices from her time with Jason. He drove his tongue into her gaping hole while he rubbed his nose against her swollen clit. He sucked a mouthful of juices out of her and knew it was mostly Jason's cum. He moved his head up and sucked her big clit into his mouth. He moved his hands up to pinch her hard nipples while he sucked her clit like a dick.

It didn't take long. Sandra grabbed his head and pulled his mouth hard against her pussy. Her thighs squeezed his head. She let out a moan that could only be described as guttural. Her inner muscles convulsed and filled Mike's mouth with the combination of Jason's cum and her own cum. This wasn't making love. This was frenzied sex!

She finally relaxed and let her ass fall back down on the bed and her thighs fall to the sides. Her flat chest was heaving as she gasped for breath. Fresh sweat glistened on her skin. Mike lay his head on her thigh, still licking her sensitive hole, savoring the amazing musky combination of tastes and smells between her legs.

She pulled him up to kiss her. "That was amazing," she said, her voice still breathy.

"Yes, it was," Mike agreed. He lay beside her softly caressing her sweaty body.

When Sandra was breathing normally again she turned on her side to face him.

"So, there's something I've been thinking about ever since I first saw hour bra and panties last night. Something I want to do," she said.

Mike smiled at her. "Well, I can't imagine me saying no to anything you want to do right now," he laughed.

"Good!" she smiled. "Come on," she said as she rolled out of the bed. "Let's take a shower and rinse all the sweat and cum off."

Mike followed her, still wondering what she had in mind. "Ok. Then what?"

She started the water in the big walk-in shower. "Then I want to dress you up on my clothes," she smiled. "I want to treat you like my little doll and try different outfits on you. And I want us to hang out in our bras and panties and talk and get to know each other."

"Can I have a clean bra and panties after our shower?" Mike asked as he followed her into the shower.

"Of course, silly!" she said. "I have a few different bra and panty sets I want you to try on. And this one dress I have that I think will look absolutely killer on you. And a skirt and blouse that I think will be perfect for you to wear to work."

Mike looked at her and raised an eyebrow. Sandra laughed. "When the time is right, dear," she said. "When the time is right."