Caught Wearing a Bra! Pt. 02

Sandra stood and let her blouse fall on the chair behind her as she stared at Mike's chest.

"Oh, that's so pretty," she whispered when she saw the soft pink bra with darker pink lace along the top edge of the cups, with a tiny light pink bow in the middle between the cups. She stepped closer to Mike and put her fingers on a bra cup, feeling the satiny fabric. "So sexy!"

"So is yours," Mike said. He stared at her flat chest covered by a lacy bra. He could see her long nipples poking at the thin material of the cup and wondered why he'd never noticed her nipples before. Surely they showed through some of the tight blouses she wore. Then he remembered the foam rubber pads she usually had in her cups.

She rubbed her fingers across his small, hard nipple. Mike moaned a little and felt his dick start to grow in his panties. He reached up and ran his fingers over Sandra's nipples.

"OH!" she said when he touched her nipples. "My nipples are very sensitive," she smiled. "I think yours are, too."

"I guess so," Mike said. "No one's ever really played with mine except me," he laughed.

Sandra took a nipple between the thumb and forefinger of each hand and squeezed gently. Mike moaned and pushed his chest against her hands.

"Mmmmm, that is so sexy!" she smiled. She ran her fingers around both of his nipples, then gently pinched them again. "I've never played with a man's nipples in a bra before."

Mike moaned and stood up on his tiptoes. He gripped Sandra's nipples between his fingers and squeezed. Sandra let out a deep growl and pushed her pubis against him, then moved back.

"And your panties match it?" Sandra asked.

Mike nodded, blushing. She moved her hands down to his belt and started to open it. At the same time Mike found the zipper on the back of Sandra's skirt. He unzipped it and her skirt fell around her feet. She unbuttoned and unzipped his pants and they fell around his feet.

Mike used his feet to slip his shoes off and stepped out of his pants. He kicked them to the side and now stood before Sandra with his matching panties and bra on full display. Sandra kicked her skirt to the side so she was almost naked, too.

"Oooh! Pantyhose!" Sandra said when she saw him without his pants.

Mike blushed and nodded. "I've loved to wear pantyhose since the first time I put them on," he admitted.

Sandra laughed. "Me, too. Again, they made this unsexy girl feel sexy!"

Mike looked at her in her panties and pantyhose. "I think you are very sexy," he said quietly.

Sandra dropped to her knees in front of him. "Pretty, pretty panties," she said softly as she ran her fingertips softly across his lower torso, admiring his pink panties with dark pink lace trim. There was a tiny pink bow, just like the one on his bra, on the front waistband of the panties, just above the base of his small hard shaft. The panties and hose were holding his hard cock against his body, stretched to the side.

Mike moaned again when he felt her fingers run along his hard pantyhose and panty covered shaft. He was afraid he might cum if she rubbed him much more.

But she didn't. For now Sandra seemed to want to touch him, to feel his hosed legs and his nylon clad ass and torso. She grabbed his hips to turn him around so that his back was to her.

"Such a cute, sexy ass," she whispered as she ran her hands over his cheeks and hips. Mike moaned again when she grabbed his hips and pulled his ass back against her face. He thought for sure he might cum when he felt her rub her lips and cheeks around on his nylon covered ass.

She stood and put her arms around him, her hands over his bra cups. "You are so sexy!" she whispered hotly as she pinched his nipples and pushed her pubis against his ass. She lowered one hand to the front of his panties.

Mike tried to move her hand away from his cock, but it was too late. Just as she wrapped her fingers around it he felt the first pulse.

Sandra felt it, too. She could feel his cock pumping cum into his panties. "Oh, shit, baby! Are you cumming in your panties? Oh, fuck, that's so hot! You're cumming for me?"

Mike was embarrassed. But he couldn't stop it. He stood there, his shame building as shot after shot of cum exploded out of his swollen head.

"I'm sorry, Sandra," he gasped. "I couldn't help it. You touching me... I've never been touched like that... wearing hose... I got too excited... I'm so sorry!"

Sandra kept his grip on his cock as the last of the hard pulses shot through it. She hugged him tight to her, pressing as much of herself against his back as she could.

"Oh, baby, baby, don't be sorry," she whispered. "It's so hot! Mmmmm, I love that!" she cooed as she rubbed her hand over the front of his hose and panties. She could feel the dampness under the two layers of nylon.

She slowly sank to her knees again and grabbed his hips to turn him back around. She held his hips and ran her tongue around the outline of his cock, then hooked her fingers in the waistband of his hose and panties. She pulled them down just enough to get her tongue on his cock and pubis to lick some of the cum into her mouth.

"You taste good," she said softly as she pulled his hose and panties down a little more. She continued to lick him, tasting the cum he'd spewed in his sexy pink panties. She sucked his helmet head into her mouth and felt a gush of cum ooze out onto her tongue.

She pulled his hose and panties up as she stood and pushed her lips against his, her tongue against his lips. Mike opened his mouth when he felt her tongue. She pushed her tongue deep into his mouth, and Mike could taste the tart, musky flavor of his cum. He'd tasted it many times after he jacked off. But it was so much sexier this time!

Sandra wrapped her arms around Mike's neck to hold him in the passionate kiss. Mike put his arms around her chest and hugged her to him. He could feel her pushing her panty and hose clad torso against his. He could feel the wet mess of his cum in his panties.

Sandra slid her hands down his body and put them on his firm ass. She pulled him to her and humped her hips, pushing her pubis against his.

Mike broke the kiss and started to slowly slide down her body until he was on his knees in front of her. He looked at the almost sheer panties that matched the almost sheer bra she was wearing. He could see that she was shaved smooth. He could see her slit, and the moisture seeping from it, and the wet spot in her panties and hose. He could see her swollen clit trying to peek out from between her smooth lips.

He looked at the pussy barely concealed by two layers of sheer nylon. He'd never been this close to a real, live pussy before. Neither of his two dates had resulted in any kind of sexual play.

He pushed his face into her thigh gap, inhaling her horny, musky scent. Sandra gasped and spread her feet apart. She put her hands on his head and pulled his lips tight against her nylon covered pussy. Mike put his hand on her soft ass cheeks and pulled her tight against his mouth.

"Ohh!" Sandra yipped when she felt him licking the crotch of her hose and panties. She spread her thighs apart and pulled his head in. "Mmmmm, yeah, oh, yeah, lick my pussy," she groaned.

Mike could feel her hips rocking, pushing her pubis against his open mouth and probing tongue. He could taste her musky juices that had seeped through her panties and soaked her hose. He pushed his tongue hard against her, rubbing her clit with his tongue. He was glad for all those hours he'd spent reading stories describing men licking pussy... and women licking pussy.

He mimicked her actions- he put his hands on her hips and turned her around so he could rub his hands and face and tongue all over her round hose covered ass. He pushed his tongue hard against her crack, and Sandra moaned and pushed her ass back against his face.

Mike slowly stood, still behind her, and reached around her to pinch her nipples, much like she had done to him. Sandra's body shuddered when he pinched both of her almost inch long nipples. He bit gently on her neck and slid a hand down to her pubis.

Sandra moaned when he bit her neck, pinched her nipples and curled his fingers into the crotch of her hose all at the same time.

"Oh, Mike!" she gasped. "Oh, that feel so good! So good!" she moaned.

Mike pulled her ass back against his crotch. Even though his dick was only half hard, since it was confined in his panties and hose he still had a nice bulge that pushed into her ass crack.

Sandra raised her arms over her head and put them around his neck. "Mike, you're going to make me cum!" she whispered as she pushed her ass back against his bulge, then forward against his hand.

"Good!" he whispered hotly in her ear. "I want you to cum for me," he told her. "Mmmmm, let me make you cum."

A fairly continuous moan was coming from Sandra's mouth as Mike continued to pinch her nipple and caress her pussy while he pushed his bulge against her ass.

He knew she was close. Her movements were jerky, not smooth. Her breath was coming in small gasps going in and high pitched yips going out. He could feel her thighs gripping and releasing his hand. He could feel the crotch of her hose getting even wetter and hotter.

Suddenly she put one hand over his hand on her nipple and the other over the hand in her thigh gap. Her legs went rigid, then started to tremble. She stopped breathing in mid-squeal. Her body arched away from his.

Mike leaned back and used the hand between her legs to lift her off her feet. She curled her legs up, rubbing her hosed feet and legs against his hosed legs.

"Ohmygod ohmygod ohmygod!" she almost screamed when the peak of her orgasm finally hit and she started to slide down the other side.

Mike felt a flood of hot fluid gush out of her, coating his hand, soaking her nylon clad thighs. Her knees spread wide, then slapped together, then spread again. He felt a wave of sexuality sweep over him when he realized he'd just made a woman have an orgasm for the first time in his life!

She finally put her feet back on the floor to help support her weight. Mike still kept a firm grip on her, using her crotch as a handle to make sure she didn't collapse to the floor.

Sandra turned her face to the side and put her hand on the back of his head to pull his mouth to hers.

"Oh, my, god, Mike! I'm not sure I've ever had a cum that hard! Thank you!" she gasped as she pushed her tongue into his mouth.

"There's more where that came from," Mike smiled, his confidence growing.

Sandra turned her body to face him as they kissed. She put her arms around his neck as he put his hand on her ass. Her body jerked when he pushed the bulge in his panties against her pubic bone.

"We need to eat something," she said when they finally moved apart. "Do you want a robe or something to put on?"

"Yeah, a robe or gown would be nice," he said. "Or I can put my shirt and pants back on."

Sandra shook her head. "I'm not ready for you to do that yet," she said. She looked down at him and giggled. "But can I please take your black socks off?"

Mike looked down and laughed. He always wore socks to make sure no one noticed his hose if they happened to see his ankles. When he took his pants off he didn't bother to bend over to take the socks off. Sandra didn't seem to mind at the time.

He raised first one foot, then the other as Sandra knelt in front of him. She tossed the socks on his crumpled pants.

"Oooh, such pretty toes!" she said when she saw his ruby red nail polish.

"Thank you," Mike blushed. "Just one more thing to make me feel girly."

Sandra stood back up and looked at her own toes adorned in turquoise polish. "I agree," she laughed.

Mike followed her into the bedroom to get them each something to wear. He noted that it was probably the most feminine bedroom he'd ever seen. His was decorated more for a female than a male, but hers was over the top feminine.

Sandra went into her walk-in closet and came out with two sundresses. "How about a cute sundress?"

"Perfect," Mike smiled.

Both dresses fit tight around their flat chests and were mid-thigh length. Mike could see Sandra wearing these out running errands, shopping, even on a casual date. He accepted the one she handed him and slipped it over his head.

"I usually don't wear a bra with these," Sandra told him. "But today I want to keep mine on, and I want you to keep yours on, too, please."

"I want to, too," Mike giggled. "I pretty much wear one all the time. I even have some that I sleep in."

"Me, too!" Sandra laughed.

They decided to have pizza for supper. Sandra refilled their drinks and they sat on the couch, legs tucked under them, and talked while they waited on the delivery.

Sandra told Mike how it was growing up looking more like a boy than a girl, how her cousins and friends sometimes teased her. Mike told Sandra about growing up wanting to be a girl, and how his cousins and friends teased him when he wore his sister's clothes.

"So you wore your sister's clothes in front of everyone?" she asked.

Mike nodded. "Yeah, for a while. Then their teasing got cruel so I stopped."

They sat in silence for a bit before Sandra spoke.

"You want to hear something funny?" she asked quietly. "When I was in my teens I got teased when I wore a dress, too. I guess I looked so much like a boy they thought... I don't know what they thought. But for a long time I didn't wear feminine clothes."

"I'm sorry," Mike said. "I know that must have hurt."

Sandra nodded. "It did. Probably about the same as your family teasing you for wearing a dress."

Sandra drained her glass and looked away. "I was so jealous of the girls in high school, the clothes they wore. They could be all cute in a dress or skirt, or they could be all cute in jeans and a t-shirt. I just looked like a feminine boy when I tried to look cute in jeans and a t-shirt, and I didn't wear cute dresses for fear of being laughed at."

Mike laughed out loud. "That is hilarious!" he said. "I felt the same way about the girls in high school! I mean, it's not fair that they can wear my clothes and no one gives them a second look, but if I wear their clothes... well, that causes all kinds of problems!"

Sandra laughed. "I know. And it's still that way," she said.

Mike nodded. "I know. I mean, if we needed something from the store I'd have to change back into my clothes to go, but you could actually put my clothes on and go and no one would care."

Sandra nodded.

"You know," Mike said sadly. "Usually when I'm at home I'm wearing a dress and if I need to run out, even to get my mail, I take the dress off and put on sweats and a t-shirt and regular tennis shoes. Just once I'd like to be able to just grab my purse and run to the store without changing."

Sandra nodded again. "I know, sweetie," she said. She reached out to pat and rub his shoulder. "I want that for you, too."

She got up to refill their glasses.

"I have an idea," she said with a smile as she handed him his glass. "How about if, when the pizza gets here, you answer the door?"

Mike laughed. "You mean, like this?"

Sandra nodded. "Yes! You just smile and take the pizza and pay the driver. It won't be like going to the store, but it's a start."

Mike thought about it. "You know, I've said I was going to do that so many times when I'm home alone," he said. "But when the time comes I've always slipped on a shirt and pants to answer the door. I've done it in hose with no shoes on, but never in a dress."

Sandra held her hand out to him. "Come on," she said, pulling him to his feet.

Sandra took Mike to her bathroom and had him sit at the vanity. She brushed his slightly long hair up to give it some body and a somewhat feminine look. She brushed some pink blusher on his cheeks, then put some dark pink lipstick on his lips.

"Look in the mirror at us," she whispered as she leaned down to put her face on a level with his. "There's not much difference in how we look."

Mike took a deep breath and nodded. "Ok. I'll do it," he said as they walked back to the living room.

Mike froze when the doorbell rang. He looked at the door, then at Sandra. "Are you sure this is a good idea?"

Sandra smiled at him. "Yes, baby, I'm sure. I'll be right here."

Mike took a deep breath and stood. He picked up the money he'd taken out of his wallet when he ordered the pizza. He walked to the door on shaky legs.

"Hi! I've got a medium all meat pizza for Mike Alford," the young delivery man said.

Mike took the pizza from him and handed him the money. "You can keep the change, honey," he smiled.

The man looked at Mike, then at Sandra, then back at Mike.

"Um, thank you, si... ma'am?" he said hesitantly.

Mike laughed. "You're welcome."

The delivery man blushed and looked at Sandra, then back at Mike. "You're both pretty," he said before he turned and headed back to his car.

"Thank you!" Mike called after him.

"So, I have to ask," Sandra said when they were settled at the table to eat. "You said when you were young you wanted to be a girl? You mean, you wished you had girl parts?"

Mike laughed. "Well, to be honest, I didn't really relate my genitals with my gender. I just knew that girls got to wear a bra and cute dresses and cute shoes, so I wanted to be one."

Sandra laughed and nodded. "Ok, I'm going to get a little personal, so if it's too much just say so, okay?" Mike nodded.

"So, did it ever get sexual?" she asked. "I mean, where you got turned on when you put on panties and a bra and hose and needed to, um, take care of things?"

"Not really," Mike told her. "I mean, yes, I did, but not because wearing panties and a bra turned me on. Panties and a bra felt natural to me, not sexual."

"So, are you bi?" she asked.

Mike hesitated. "Yes. At least I think so. I actually don't have any experience with girls. When I went to community college I met some guys who liked to dress and play with each other. But when I think about dating and being in a relationship I always see me with a girl. Are you?"

Sandra laughed. "Why would you ask me? I'm not wearing boy's underwear!"

"Do you think all bi guys crossdress?" Mike asked her.

She laughed and nodded. "Okay, you've got me there. Yes, I've played around with some girls here and there, and enjoyed it."

"But you prefer men?" Mike asked her.

She tilted her head and looked at him. "I'm not sure. I guess I've been with men more because, well, men ask me out and women don't. But I'm not sure I prefer them."

They sat silent, eating, for a bit.

"I think I like them with a dick, but not all gross and manly," she said. "If that makes sense."

"You mean like me," Mike said.

"Exactly like you," Sandra said. "I think that's why I've been so attracted to you since I found out you like to wear bras. And why it was so easy for me to take my clothes off in front of you. Not very many people, male or female, have seen me without a shirt on."

"I can say the same thing!" Mike said. "Even with men, I tend to keep my shirt on. And my panties."

Again they ate in silence for a while before Sandra spoke.

"Hey, you think after we eat we could go to the bedroom and get completely naked? Both of us?" she asked.

Mike nodded. "I think I'd really enjoy being naked with you," he told her.

She smiled over her pizza and looked him in the eyes. "Full disclosure. I want you to fuck me."

Mike blushed. "I want to," he said. "But, um, I'm not very big. You might be disappointed."

Sandra shook her head. "Nope. From what I saw earlier, you are just the right size."

Later they stood face to face beside the bed. The dresses had been tossed carelessly on the floor near the closet door.

"Um, Sandra?" Mike said hesitantly as they faced each other.

Sandra looked at him, wondering if he was having second thoughts, and wondering why. Was it her body?