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Mindy fashionista

Part 3 of the Minday series - Cross dressing man hires Laura and Mindy for some girl fun
Laura’s escort business was becoming very successful, and she was able to pick and choose her clients. She shied away from any who she felt uncomfortable with, and she stuck to her rule of no sex, no matter how much money was offered. Her friend Mindy, who had escorted her on two of her “dates”, was so intoxicated with the thrill of exposing herself that she longed to be able to go into business with Laura. She knew, however, that there was no way Jeff would ever go for it.

They spent their time together at Laura’s house, since she needed to be on-line as much as possible, so as not to miss out on any business.

One morning, as they sat at Laura’s kitchen table talking, Mindy said, “Well, my days of leisure are over.”

“What do you mean?”

“Megan starts driving next month, and I promised Jeff that when she did, I’d go back to work to help with the finances.”

“What do you plan to do?”

“I don’t know. I haven’t worked in so long, I’m probably not qualified to be much more than a receptionist. I don’t want to work evenings or weekends, so retail or waitressing are out.”

“You know, it seems a shame to have to go to an office every day just to make what you can make in two or three hours in my business.”

“Yeah, but my husband wouldn’t be very understanding.”

They sat quietly for a while, then Mindy said, “Hey, Laura. If I did go into business with you, do you think there would be enough demand during business hours to make any money? And do you think there’d be enough demand for two girls at once to make any money?”

“As for the daytime hours, most of my demand is at night. But I do get requests for playtime during the day. As for two girls? I don’t know, I’ve never advertised that.”

Laura had a website that was advertised on a number of adult personal ad sites. Men saw her on those sites and connected with her via on-line messages, if she was on-line, or they sent private messages if she wasn’t that she could respond to when she got on-line.

“I could tell Jeff that I have a friend that has an organizing business. You know, going into people’s houses and organizing their closets or whatever. I could tell him that I was going to help you with it. He’s never met you, he wouldn’t know.”

Laura logged into her account on the adult personal sites and changed them, advertising the availability of naughty friends for those gentlemen who needed extra attention.

“We’ll see what happens,” she said.

A couple of days later, as they sat in Laura’s kitchen, an on-line message popped onto her computer. As usual, Laura quickly went to the guy’s profile to see what she could learn before responding.

It turned out to be a forty five year old guy who liked to dress up in women’s clothes. There were lots of pics of him in all sorts of women’s garments, though none of his face.

“His profile says he’s straight, but he is definitely twisted,” Mindy said, looking through his pictures. “Hey, look at that,” she said, pointing at the screen. “He’s only 5’7” and 145. That’s really tiny. Look how small and delicate his hands are.”

Laura responded to his request to chat.

“Hi, sexy. Do you like to have fun?”

“Hello,” the man replied. “I like your profile. Your lingerie is beautiful. Do you like men in women’s clothes?”

“It sounds delicious,” Laura wrote. “What do you like, besides wearing women’s clothes?”

“I’d like nothing better than to be watched wearing women’s clothes, but it wouldn’t be a good career move. So I usually just enjoy them in private.”

“Would you like to party with me? I’d love to see your wardrobe.”

“Would you bring your lingerie too? I’d love to see you in different outfits.”

They asked him all about himself, and he seemed eager to chat. It seemed that the guy had always preferred the company of women. As a child, he always hung out in the kitchen with the women during family gatherings, rather than play outside with his male cousins. He enjoyed the smell of perfume and the conversation of the women.

His secret fantasy was to be included in the female discussions that occurred when they were by themselves, with no males around. He could only imagine what they talked about. He longed to share in intimate “girl talk”. He longed to go shopping with the girls, and try on intimate clothes with them in the dressing room.

“Where do you live?” Laura asked him.

“I can’t be seen coming or going from my home dressed up. I’d have to do this elsewhere.”

“You’ll have to get a hotel. I’ll charge you $125 for the first hour, and $100 for each additional hour.”

“I wonder if he wants another spectator,” Mindy said.

Laura typed in, “I’ve got a friend here that likes to party. Would you be interested in two girlfriends?”

“Definitely, if she’s as hot as you,” the guy wrote back.

Mindy’s heart was beating rapidly and her palms felt clammy, anticipating that she was actually going to go through with this. She had been on two of Laura’s dates previously, but she knew that each time she was risking her marriage. She didn’t want anything to happen to her family, but she was addicted to exposing herself.

“Let me take a photo of you,” Laura said as she got out her cell phone. “I won’t include your face. Take off your shorts and top.”

“What? No way.”

“Come on, it won’t have your face. Let’s see how much money lover boy has.”

Mindy nervously took her clothes off in front of her friend.

When she was down to her panties and bra, Laura said, “Now turn around so I can shoot your ass. Turn your body toward me so I can get a profile of one of your cups. Perfect.”

She uploaded the picture to her computer, then forwarded it to the guy.

“See, she’s got a better body than I do,” Laura wrote. “And she’s dying to see you in pantyhose. She’s got a thing for men in pantyhose.”

They giggled as Laura wrote that last part.

The guy was obviously well off; he didn’t quibble about the price, even though Laura charged him dearly. It was, after all, going to take an entire afternoon for both of them. After the arrangements had been made, they signed off. Mindy was so excited she could hardly contain herself. They planned to meet at a mall for lunch, then shop for lingerie and try them on together. Later they would meet at his hotel room for a fashion show.

Mindy and Laura arrived on time at the Cheesecake Factory restaurant in the mall and got a table, telling the hostess their friend Carol would be arriving shortly. As they studied the menu, a lady approached.

“Hello, Dears,” she said, giving them both an air kiss.

He was drop dead gorgeous; he must have spent a mint on the blond wig, it looked so realistic. His makeup was impeccable, and he was dressed in what appeared to be a very expensive suit. He wore a fashionable skirt with a silk top and a jacket over it. He had nude pantyhose over his shapely legs, and his jewelry was just right; classy, but not gaudy. He made Laura and Mindy look like his country cousins, he was so well dressed.

“You look beautiful,” Laura said. “I’m Wendy and this is Jenny,” she said, motioning toward Mindy.

“I’m Carol. It’s so nice to meet you both. I’ve been so looking forward to this. Have you chosen yet?” he said, as he grabbed a menu.

“No, we just sat down. Everything here is good.”

“I’m so excited, I don’t think I can eat a bite. I think I’ll just get a salad,” he said, putting the menu back down. “You girls are even prettier than your pictures.”

“Thank you,” they said in unison.

After they had ordered, they resumed their conversation. Carol did most of the talking. He had never been able to act out his fantasy anywhere in public with other girls, and he was gushing with excitement. His voice was high enough to actually be a girl’s voice.

“I’m so looking forward to shopping with you,” he said. “There’s not much I enjoy more than shopping, especially for lingerie. I just love everything feminine and lacy.”

“Oh, me too,” Mindy agreed. “Although I hate shopping for bras. It’s so hard finding one that looks sexy but is still comfortable and doesn’t show your nipples. And finding one that fits everywhere is another hassle. That’s why I always just get the same ones; at least I know they fit right and the straps won’t keep falling off.”

Carol was in paradise; this was exactly the sort of girl talk that he so badly craved. To be one of the girls was something he’d long fantasized but never experienced. His dick had been swollen since he first slipped on his pantyhose, but now it was fully erect, plastered against his body by the tight pantyhose.

“Oh, I’m an expert at fitting bras,” he said. “I’ll help you. What kind are you looking for?”

“I’d love to find something thin enough to not look like heavy padding, yet not show my nipples when they get hard. And if it were lacy and pretty, that would be a bonus. Also, I’d like to find a strapless one that I didn’t have to tug at all the time, to wear with spaghetti strap tops. I think it’s so crass to have exposed bra straps.”

“Oh, I know,” Carol said. “So many girls show their straps these days. I just think it looks so trashy.”

Carol picked up the tab, and they walked out into the mall.

“Victoria’s Secret?” Carol asked.

“Sure,” the girls agreed.

When the salesgirl learned that “Jenny” was shopping for a new bra, she offered to size her.

“That won’t be necessary,” Carol said. “Do you mind if we use your tape measure for a moment?”

Carol took Jenny back to the dressing room. Once inside, he said, “They mean well, but they really have no clue. They measure you with your clothes on, and they give bad advice. They have beautiful product, but they just don’t know how to help a girl with the right size.”

Carol had Jenny take off her blouse, explaining that the ruffles around the neckline would make it hard to get a good reading otherwise. She felt awkward standing in only her bra, but Carol acted as if it were nothing.

“Lift your arms,” he directed. “Now, exhale and hold it.”

When she had done so, he wrapped the tape tightly under her bust.

He took a pen out of his purse and made a note on a scrap of paper.

Facing her, he wrapped the tape around her back and over her bust at its fullest to get the cup measurement. He wrote something on the paper, then did some quick calculations.

“Okay, this is only a guess, especially since you’re wearing a padded bra, which throws off the calculations. First of all, with your breast shape, I would try a demi cup bra. I think you’ll find it much more suitable than your current bra, and I think you’ll find it sexier looking. It appears that a 34C would be about right. I’ll go get a couple to find the right size. You can wait here.”

Wendy was looking at panties, killing time while the girls were measuring. When Carol came out, she joined him, and they looked at the demi cup bras. He picked up both a 34C and a 36B black, lacy bra, and went back to the dressing room.

“Here, try this one on,” he said, handing her the 34C. “Have you ever worn a demi cup?”


“I think you’ll like it.”

Jenny’s heart raced as she unsnapped her bra. She felt slightly dizzy as she removed her bra in front of this stranger.

She quickly put the new bra on and surveyed herself in the mirror. Carol tested the fit by putting his fingers under the band at the sides and in the back.

“Wow, this really is comfortable,” Jenny said. “And it looks great.”

Carol said, “I think you should try the other one.”

“But I’ve always worn 34C. I’ve never worn a B cup.”

“Let’s just try it,” he said. “I’m not completely satisfied with the fit on this one.”

She took the bra off and hung it on a hook. She could feel the man’s eye’s on her, surveying her bare breasts. She quickly put the 34B on.

“Wow, you’re right, this one feels even better.”

“This is the perfect size for you, dear,” he said. “Ruffle your nipple and see if it shows through the material.”

Jenny played with her nipple until it was hard, and looked in the mirror. Even though the bra wasn’t heavily padded, her nipple didn’t show through, perhaps due to the quilted pattern. It was beautiful, comfortable and it fit just right.

“I love it. Thank you so much. You can’t imagine how long I’ve been trying to find a good bra.”

“No need to thank me, glad to do it. Now let me go find you a strapless.”

Jenny wound up buying three demis; a nude, black and white one, plus a strapless that fit perfectly, stayed up when she moved, and felt comfortable. She never would have thought it possible. She gushed with appreciation for Carol.

Carol was in heaven. This day was turning out even better than he had anticipated. Having girl friends to hang out with was so cool, and these girls were beautiful, fun and exciting to be around.

The girls walked through Macy’s, looking at clothes and trying on a few. Carol went into the dressing room with Wendy as she tried on jeans. When she took off her skirt and stood there in her pantyhose, Carol thought he was going to cum. He absolutely loved the look of a woman’s tight ass in a pair of shimmering pantyhose.

Finally, they took their purchases and left to head to Carol’s hotel. When they got there, Wendy and Jenny took in a duffle bag with the outfits that they would model. Carol was so excited he could barely contain it. He talked non-stop on the way up the elevator. He had rented a suite, giving them plenty of room to change clothes.

He had a bottle of wine chilled and poured a glass for each of them. They sat and sipped their wine, talking.

“So is there anything more uncomfortable than pantyhose on a hot day?” Wendy asked.

“No, but there’s nothing sexier either. A woman of a certain age; say, over thirty five, simply must wear them with a skirt,” Carol said.

“Yeah, but that doesn’t mean we have to like it,” Jenny said.

“Imagine my situation,” Carol said. “I have an extra appendage to deal with, and there’s really no room in pantyhose for that.”

“How does that work?” Wendy asked.

“You’ll see. It certainly holds everything in place, that’s for sure.”

The girls giggled. Carol topped off their drinks with the rest of the bottle of wine, and said, “Let’s get started.”

“First you must tell me where you bought that outfit,” Jenny said. “It’s absolutely gorgeous.”

“It’s an Albert Nipon. I got it at Neiman’s.”

“Okay, that explains why it’s so beautiful.”

“All my outfits are wool. I detest polyester. The designers would never get away with selling men’s suits in polyester. I don’t know why women stand for it,” Carol said.

“Why don’t you show us some of your outfits, Carol. I know you’re dying to,” Wendy said.

“I am,” Carol said.

She was positively beaming. She went into the other room.

“No peeking,” she said.

The girls sipped their wine as Carol changed.

“Ready?” he said.

“Ready,” said the girls.

Carol came into the room wearing a stunning bikini. The girls were amazed. His breasts were so lifelike, they couldn’t tell he was a guy. The skimpy bottom showed off his shapely legs, which were as smooth as a girl’s. The girls got up and admired his suit. Up close, they could make out the lines where his breast forms met his body.

“Do you mind if I touch?” Wendy said, knowing that he would enjoy that.

“Not at all,” he said, beaming.

It even felt life like. The nipples were stiff and showed through the swimsuit. She looked incredibly sexy. The bottoms were skimpy, yet you couldn’t tell that she was a man.

“Where’d you hide the sausage?” Wendy joked.

“Wouldn’t you like to know,” Carol said.

“Well, that swimsuit is gorgeous,” Jenny said. “I wish I looked that good in a swimsuit.”

Carol strutted out of the room with a huge smile on his face to change into another outfit. The girls were amazed, wondering how he was able to wear such a skimpy outfit and not show any bulge.

“Ready?” Carol called from the other room.

“Ready,” said the girls.

Carol came strutting into the room on a pair of 5” high heels wearing a tiny thong and a short, short, see through nightie.

“Wow!” Jenny said. “How sexy.”

Carol strutted and preened, striking sexy poses.

“Where are the boys?” Wendy asked, looking at the absolutely flat front of his thong.

“Hey, a girl’s allowed to have her secrets,” he answered.

“Seriously, where’s the beef?” Wendy asked.

“Okay, okay,” Carol said. “I’ll let you in on my secret. It’s called a hiding gaff. Tight underwear that holds everything in check.”

He turned away from the girls and bent over at the waist. They could just make out the bulge under his thong toward the rear.

“I have different ones for wearing under different types of garment.”

He sashayed out of the room to change into another outfit.



This time he wore a little black dress. He was stunning. The short dress was off the shoulder, and he wore a pair of black elbow length evening gloves and a beautiful strand of pearls. He wore a pair of nude pantyhose, which highlighted his beautiful legs.

“Well, if I were a man, I’d be all over you,” said Wendy. “Us normal girls wouldn’t stand a chance.”

“Don’t sell yourself short,” Carol said. “You’re both quite stunning. It’s your turn now.”

“Okay, but first you gotta change back into your pantyhose, okay?” Wendy said.

“Alright,” Carol said, feigning reluctance, even though the girls knew that he loved nothing more than wearing pantyhose.

Carol came back into the room in nothing but a pair of pantyhose. His breast forms were uncovered. His dick was hard, and the tight pantyhose plastered it against his body, making it look even harder and larger than it actually was. The girls went into the other room to change.

They came back in, hand in hand, wearing dominatrix outfits. Wendy was dressed in a pair of black shoes with stiletto heels, a pair of black fish neck stockings held up with garter belts, a skimpy pair of black satin panties that barely covered her cheeks, and a cupless black leather corset. The corset laced up the back and had a metal zipper up the entire front, as well as four metal buckles up the front. Her large breasts stuck through the openings in the corset. She had a riding crop in her hand.

Jenny had on a red corset that was laced on the front and the back with long laces that left exposed a large section of the middle of her body, which included most of her breasts. The sides and nipples were covered, the rest of her cleavage exposed. She wore a red satin g-string, and red high heeled shoes.

“Wow, I’d hate to be on the wrong side of you girls,” Carol said.

“You have no idea,” Wendy said. “Stand up and bend over.”

Carol stood and bent at the waist, presenting his ass to Wendy. Wendy rubbed his butt with her crop, then with her hand. She swatted his butt a couple of times, then ran the crop between his legs, rubbing his dick. He moaned as she rubbed him.

“Not so fast, big boy,” Wendy said.

They went back into the other room to change. They knew their next outfit would be Carol’s favorite. They came back into the room wearing nothing but pantyhose. They had a pair of nude pantyhose on, plus they had removed the legs from another pair and wore the tight nylon panties around their upper body as a tube top. The tight, elastic, see through, shimmering material pressed their tits flat against their chest. Their stiff nipples pushed against the tight material.

“Wow!” Carol said. “I like that.”

“I thought you might,” Wendy said.

They took Carol’s hand and helped him to his feet, then rubbed their bodies seductively against his. The feeling of nylon against his body, coupled with the aroma of the girl’s perfume was incredible. He wanted nothing more than to take these girls, rip their nylons and pound their pussies with his hard, aching dick.

Wendy wrapped her arms around Carol’s body and grabbed the front of his pantyhose, pulling them out to unleash his dick, then pulling them up as high as she could pull them, trapping his dick in the crotch of the pantyhose. He moaned loudly as she repeated this, over and over.

Carol grabbed Jenny and hugged her from behind. Jenny jutted out her butt into his crotch. He reached around her and grabbed her breasts, rubbing them through the nylon material, finding the nipples and rubbing them. Jenny allowed him to rub her butt with his crotch. The feeling of nylon on nylon was very erotic. She could feel Carol’s hard dick rubbing against her.

Wendy continued stretching his nylons, pulling them up as high as she could. His hard dick was trapped in the tightly stretched pantyhose as he rubbed it against Jenny’s nylon clad butt.

The friction was too much. Carol’s body slumped, held up by the girls as he grunted and spurted into his pantyhose. Jenny felt the warmth spreading onto her butt as Carol leaned onto her. His knees buckled, and it was all he could do to keep his balance. Jenny pulled away, and Wendy helped him to the bed. The girls gathered their things, got dressed and left.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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