Caught Wearing a Bra! Pt. 05

"So tell me what happened in Crawford's office today," Sandra said as she helped to hook the first bra around Mike's chest. He already had the matching panties on. She was still naked.

"Yeah, I probably need to tell you about that," Mike said. He gave Sandra a brief description of how Joe asked to see his bra and panties and he ended up rubbing his nylon clad pubis against Joe's dick until he spewed cum on both of them.

"So the old man cums a lot?" Sandra asked when Mike told her how it spurted up on their chests. She went into her closet and came out holding a long cotton dress for Mike to try on.

"Yeah, quite a lot," Mike told her. "I rubbed on him and smeared it all over both of us. I wiped some of it off, but a lot of it dried on me."

"I know," Sandra laughed. "I could smell it. Remember?" She bunched the dress in her hands and held it up to put over Mike's head. He raised his arms to let her put the dress on him.

Mike blushed and nodded. "So anyway, after we got dressed Joe told me he has an apartment near the office for when he works late or has a client in town. He asked me to come to dinner with him."

"Dressed up?" Sandra asked as she pulled the dress down around his body.

Mike nodded. "Yes. He wants me dressed up. Wig, make-up and all."

"How exciting!" Sandra said. "Have you ever had a date like that? As Michelle?"

"No, I've never been on a date as Michelle. Well, sort of. A guy I played around with in college took me out to eat one time. But I think this will be different," Mike told her.

Sandra nodded. "Yeah. Joe is a grown man. He's also a married man. How do you feel about that?" Sandra asked. She pulled him to the side of the bed so he could look at himself in the full length mirror.

"A little conflicted," Mike admitted. "But I don't think it's so much about him cheating on his wife as it is about him being curious about his own sexuality. I like this dress! Well, except for that little bulge in the middle of it."

The dress was an ankle length cotton sheath that hugged his body. The top was like a tank top with wide straps over the shoulders. There was a slit in the left side of the skirt from the bottom hem to the middle of Mike's thigh that showed a lot of leg when Mike moved around in it.

Sandra laughed. "I actually think the bulge is kind of sexy," she said.

Mike laughed. "Maybe for around the house. But if I was going to wear this out in public I know how to deal with the bulge."

Sandra laughed. "Yeah. I've read a little about guys who dress doing a tuck. I've never been fully sure of what that means, though." She went back into the closet for another dress.

"There's a little cavity down there they can push their balls into, then they pull the dick back and some even tape it in place. I did it once and decided I didn't like it," Mike explained as he took the dress back off.

"So why didn't you like it?" Sandra asked when she came back out of the closet taking a shorter dress off of a hanger.

"Well, it's a lot of trouble to do. My balls didn't want to stay up in the cavity, and trying to keep them there while I tucked the dick back and taped it in place wasn't easy," Mike explained. "And when I got it all done it was uncomfortable when I walked and even when I tried to sit down. And, to go to the restroom you have to undo it and then re-do it. The first time I had to pee I was done with it," Mike laughed.

"I'll bet," Sandra laughed. She unzipped the back zipper on the cocktail dress she was holding and held it out for Mike to step into it. He did and turned around so she could zip it up for him.

The dress was black with silver threads running through it. It had a high neckline and a tiered bodice with layers of ruffled fabric going all the way down to the mid-thigh hem. The shoulders were cut in toward the neck so the straps of the bra Mike was wearing showed.

"Oh, Sandra, this makes me feel pretty!" Mike sighed when he looked at himself in the mirror.

Sandra reached out and ran her hand across his butt. "You are pretty, Michelle," she said softly.

"Do you have a strapless bra to wear with this one?" Mike asked.

Sandra shook her head. "You don't need a bra with it," she said. "The tiers hide that you don't have boobs. Turn sideways and look in the mirror."

Mike turned and looked at himself. "You're right," he said. "No need for a bra in this one. I like that. And no bulge, either!"

Sandra laughed. "Nope. You could get a full-blown hard on in that one and no one would know. I think this might be in the running for you to wear on your dinner date with Joe. So you think he's just curious? Maybe wondering what he's been missing out on?"

Mike nodded. "Yeah, I think so. That happens to a lot of men his age. I've talked to them online. Most of them won't ever take the step of finding out, though."

Mike faced her and took both of her hands in his. "Be honest with me, Sandra. Are you okay with me having this dinner date with Joe?"

She smiled at him. "Yes, I'm fine with it. This is our second night together, and we haven't talked about a future or being exclusive or anything like that."

Mike blushed and smiled. "Yeah. I guess I'm kind of jumping the gun even thinking about things like that. I, uh, I've never had anyone act like they... like how I feel matters to them."

Sandra pulled him to her and hugged him. He felt a tingle when he put his arms around her naked body. "How you feel does matter to me, Mike... Michelle. I'm still a little confused by all this myself."

"Thank you," he said.

She stepped back and again held both of his hands in hers. "What about you? How did you feel earlier when you knew Jason was here?"

Mike took a deep breath. "A little jealous," he admitted to her. Then he laughed. "And a little turned on."

She cocked her head to the side. "Oh?"

Mike blushed and looked down. "Well, it's a really long story, but one of my fantasies involves being with a woman who has been with another man. That's, uh, that's why I didn't want you to shower before I came over here."

"Was it what you dreamed it would be?" she asked.

"Pretty much," he said. "Ideally I would have been dressed in some slutty lingerie and spent more time licking your body... and perhaps the body of the man you were with. Maybe taste your juices on his dick."

"Oh, my," she smiled. "Well, I should have known you'd be a little kinky when I saw you in your matching bra and panties!"

"So you're not, um, repulsed that I think about things like that?" he asked.

"No, baby, not at all. Maybe even a little turned on!" she said. "I know I was turned on earlier knowing you were licking my pussy with Jason's cum in it."

"Mmmm, me, too," Mike laughed. "Will you be jealous when I'm with Joe and probably sucking his dick or maybe even letting him fuck me?"

Sandra laughed and nodded. "Probably a little," she said. "But I'd also love to be a fly on the wall watching it, too! Um, I've never told anyone about this, but I've done some of my best masturbation watching guy on guy porn."

Now Mike cocked his head and smiled. "Do tell?"

Sandra blushed. "Yeah. Something about it is just... primal. I love watching two guys kiss."

"You mean like two manly men, not a manly man and a man like me, right?"

"Well, I've gotten pretty turned on watching a man kiss a pretty crossdresser, but, yeah, when it's two manly men..." She fanned her face. "Whew!"

Mike laughed. "Yeah. Me, too!"

Sandra hugged him again. "Oh, Michelle, I think we're going to be such good friends!"

"Now turn around and let me unzip this dress," Sandra said. "I have one more outfit I want to see on you. That is if you're not tired of trying on clothes."

Mike turned his back to her and laughed. "I'm not sure I could ever get tired of this," he told her. "This is a dream-come-true for me, to have a sexy woman helping me play dress-up in her clothes!"

She helped Mike step out of the cocktail dress then handed it back to him with the hanger. "Take care of this while I get a few things out of the closet."

She came back out of the closet with a skirt and three blouses. She tossed the blouses on the bed, handed Mike the skirt and took the dress from him. "Put that on while I hang this up," she said. "Then we'll work on which blouse looks best on you. This will be for Michelle's first day at the office!"

Mike shook his head. He wished! But he took the skirt from her and stepped into it. He pulled the side zipper up and looked down at himself. The skirt was a pretty sky blue that was tight around his waist and hips but flared out as it went down to the hem that hit two inches above his knees.

Sandra picked up the first blouse and held it up to his chest, still on the hanger. "Hmmm, I'm not sure about this one," she said as she tossed it back on the bed and reached for the second blouse. After holding the other two up to him she went back to the first one. "Okay, put this one on," she said.

It was a simple off-white front button blouse, with long slightly puffy sleeves that buttoned at a cuff around his wrists. The blouse fit loose on his chest.

"Will I need my bigger forms with this?" Mike asked.

Sandra shook her head. "I sometimes don't even wear my enhancers with it," she said. "The way it's cut it makes people wonder if there are tits under it or not. You will notice that a lot of my blouses are like that."

"But I can wear a bra, right?" Mike asked.

"Oh, of course you can, sweetie!" Sandra told him. "In fact, sometimes I'll wear a darker colored bra so the straps will show just so people will know I am wearing a bra. That makes them wonder even more."

Mike laughed. "I like it," he said. "Maybe someday I'll actually get to wear it to work."

Sandra smiled. "I think you will. Let's see how your dinner with Joe goes."

Mike stood looking at himself in the full length mirror, trying to picture himself walking in to the office in this skirt and blouse. In his mind he could hear Sandra's friend Anita say 'Hey, Mike, you look so pretty today!" and another faceless female say 'Cute skirt, Mike' and a faceless male say 'Yo, Mike, lookin' hot today'. And he would walk to his cubicle and sit like a lady and do his work.

"I'm ready to get into a nightgown and sit on the couch and have a glass of wine," Sandra said. "How about you?"

Her voice pulled Mike back to the present. "Yeah, that sounds good," he laughed as he started to unbutton the blouse. He handed the blouse and skirt to the still naked Sandra. "Of course, if you don't want to put a gown on that's okay, too."

Sandra turned and smiled at him. "Oh? You like me like this, do you?"

Mike blushed, but nodded. He reached out and pulled her to him and wrapped his arms around her, running his hands over her bare skin. "Yes, I do. But I also like you in a sexy bra and panties."

Sandra put her arms around his neck and put her lips close to his. "I'll stay naked if you want me to," she whispered as she kissed him.

Mike put his hands on her bare ass to pull her against him. He ran the fingers of his right hand up and down her hair lined crack. He dug his middle finger into her crack to toy with her puckered hole. His body tingled when he felt her let out a little moan and push her ass back against his hand. He was surprising himself. It was as if he knew what to do to turn her on. Surprising considering he was only 24 hours removed from his very first time being with a naked woman.

He opened his mouth when he felt her tongue against his lips. He moaned when their tongues touched. His dick had been soft while he tried on Sandra's clothes, but now it stiffened in his panties.

"As much as I love you naked I think I want us both in sexy bras and panties and gowns right now," he whispered while they kissed.

"Good," she responded. "Me, too."

Sandra took the bra Mike was wearing off of him and reached into her drawer. She brought out two bralettes, both pink. "Do you have any bralettes?" she asked as she pulled one of them over her head.

Mike shook his head. "No, I don't have many. The one I had on yesterday is what most of mine are. I have two with bigger cups for my d-cup silicone forms."

"I think you'll like this," she said as she helped him put it on. "This is what I wear most of the time. I usually wear the ones with small cups when I want to wear my enhancers but I've worn them with a bralette, too."

The bralette was a piece of ribbed cotton that fit snug around his chest. The bottom hem that ran just under his pecs was a half-inch wide strip of spandex that actually made his pecs look like small tits. The sides of the bralette that went around his back weren't quite as wide as the part that covered his chest. Spaghetti straps over his shoulders would keep it from sliding down his chest.

Mike looked at himself in the mirror, and liked the look. Sandra reached into her panty drawer and pulled out two pairs of pink cotton bikini briefs. "You can put those on or just wear the ones you're wearing," she said as she sat on the edge of the bed to put her panties on.

"I like the matching pink," Mike said. He pushed the nylon panties down his legs and reached for the other pair of panties Sandra had gotten for him.

They sat on the couch, feet pulled up, facing each other in their pink nylon gowns and bralettes and panties, sipping wine and talking softly.

"Ok," Mike said. "I'm not saying this will happen, just a big 'what if'."

"Ok," Sandra smiled. "What if me."

"So, if we were to decide that we want to be exclusive, where would it go?" he asked.

Sandra took a sip of her wine and pondered the question. "As in the long term future?" she asked.

"Well, long term, short term... just the future. I guess what I'm asking is, will you decide you want to meet a normal guy and settle down someday?" he said.

"Define normal," she said.

Mike laughed. "How about a guy who doesn't want to wear your underwear."

"And that is how we define normal now?" she asked.

"Well, I don't consider myself to be a normal guy," Mike said. "I've never felt like a normal guy. Well, until now. You make it feel almost normal to sit here in a gown and bra and panties and sip wine with you."

She reached out and put her hand on his cheek. "Here's how I see you. You are Mike, a normal, sexy guy. And you are Michelle. A normal, sexy girl with a little something extra. I don't see that changing as I get older." She put her hand on the back of his head and pulled his lips to hers. "I'm ready to go to bed and finish what we started earlier," she whispered as they kissed.

The next morning they sat at the breakfast bar separating the kitchen from the dining area in Sandra's small house. The breakfast dishes were pushed out of the way and they were enjoying the last of the pot of coffee.

"So, you wanna have a little adventure today?" Sandra asked, grinning.

"Depends on what you mean by a little adventure," Mike laughed.

"Today is my mani/pedi day," she told him. "How about if we put on some cute sundresses and go have our nails and toes done and then go to the mall and window shop?"

Mike stared at her. 'Yes!' he wanted to say. Many times he'd sat around his own small house on a Saturday with nothing to do and thought about what it would be like to just go walk around in the mall. And to go get a mani/pedi, too? That would be so wonderful! But, while his mind and his heart said 'Yes!' his mouth said, "Umm, that sounds fun, but I don't think I'm ready or that much exposure yet."

"Nonsense!" Sandra said. "With your cute wig and just a touch of make-up...you can even wear your little forms if you want to... or my enhancers."

"Oh, Sandra, I want to. I really do. But what if we see someone I know? Or what if someone makes me?"

"Well, we'd just have to deal with that IF it happens... but it probably won't. I'm guessing no one will give you a second look," she said. "Please, Michelle? I know you want to. I've done enough reading online to know that it's something gurls like you dream about."

Mike nodded. "Oh, definitely something I've dreamed about," he laughed.

"Okay, so let's do this," Sandra said. "Let's go take a shower. Do you need to shave your legs? I don't. And then we'll get ready to go. I'll do your hair and put some make-up on you. When we're all ready to go, if you don't want to do it, you can hang out here while I go get my mani/pedi and we can just hang out here."

Mike nodded. He let her take his hand and lead him to the bathroom. In his mind he was already thinking about what he would do if someone made a comment about him being a man.

In the shower Sandra used her soapy hands to masturbate him. She had him turn so that the spray was hitting her back, not him, and used one soapy hand to stroke his hard cock while she ran the soapy fingers of her other hand up and down in his ass crack. When she thought he was getting close she pushed the tip of a finger into his tight hole. Mike moaned and pushed his ass back against her hand. She worked the finger in to the second knuckle and worked it in and out a few times. Mike's hips jerked when she finger-fucked his puckered hole. When she felt his cock start to throb she worked another finger into him. Mike groaned. "You like that, baby?" Sandra asked in a low, sultry voice. "You like when I finger your tight little hole?" "Oh, yes!" Mike said as his body tensed. Sandra felt his body tense, too, and then felt his shaft throb hard and watched a big spurt of white cream shoot from his dick against the wall of the shower.

Mike turned and put his hand between her legs, rubbing her clit as he kissed her. Sandra put her arms around his neck and spread her legs for him. Very quickly Mike rubbed her swollen clit to an orgasm, with Sandra hanging on his neck as her hips jerked her pussy against his hand.

When they were breathing normally they laughed. "I guess we both needed that," Sandra said as she rinsed the soap off of Mike. "I'm thinking so!" Mike agreed.

Out of the shower they dried each other's bodies, then Sandra worked quickly to get them ready to go. She dressed Mike first. She chose a mid-calf length sundress with spaghetti straps. The dress was yellow with the outlines of green and blue flowers on it. It had a ruffle along the top of the shirred bodice. Mike put it over his head and pulled it down into place. Sandra adjusted the bodice around his flat chest.

"You can either go like this or use a set of my enhancers," Sandra said. "I don't think this top is strong enough to hold your silicone boobies in place."

"Are you going to wear enhancers with yours?" he asked her.

"That's up to you," she told him. "If you do, I will. If you don't, I won't."

Mike looked in the mirror again. "I think I'd like some enhancement," he said.

Sandra smiled. "I have just the thing for you." She went to her dresser and took a satin bag out of a drawer. "Sit down at the vanity and pull your top down," she told him. In the bag were two foam rubber tits, natural colored and complete with slightly darker areola and noticeable nipples.

She got a tube of body glue out of a drawer in the vanity and ran a bead around the edge of each foam rubber tit. She pushed the first one against his chest, smearing the glue on the skin around his nipple and on the back of the tit. She set the tit aside and did the same with the other one on the other side of his chest.

She picked up the first one and pressed it into place on his chest. "Hold that. Keep it pressed firmly against you," she instructed him. Then the repeated the procedure with the other tit. Mike sat at the vanity, the bodice of his dress around his belly, his arms crossed so he could hold the two tits in place long enough for the glue to set.

"Now, just sit still while I do your make-up," she smiled. She put just a hint of blue-green eye shadow on his eye lids. She brushed some mascara on his lashes. She added some pink blusher to his cheekbones, then light red lipstick to his lips. "We might go with the ruby red lipstick later, but for now this will do," she told him. She had him pull the bodice of his dress back up and straightened the straps over his shoulders.