But how can a fantasy like that come to be safely? An older girlfriend sympathetic to his dressing desires named Cindy, and a tale written by Rikki........................the story begins.
"The Public Crossdressing Adventures of Mark "
aka "The Perky Walk"
Story written by: Rikki
Mark was very nervous when Cindy parked the car in the mall parking lot. It was a very cold evening as the sun was just getting ready to set.
Mark had always fantasized about being publicly humiliated, and found the thought of doing so very exciting, but as they pulled in and parked the car, his excitement of the fantasy began to fade and became a nervous fear of the reality.
Mark looked at Cindy as she shut off the car and turned to look at him. She met his eyes with hers and smiled.
"Ready for a little public humiliation Mark?" she said giving him a smile."I don't know Cindy. I've changed my mind. I'm getting cold feet," he said looking around to see if anyone was looking his way.
"Oh no you don't. You're going out there, and your going to embarrass yourself wearing women's clothes. I'm sure you will have cold feet seeing how it's 36 degrees outside." She grinned as she said it.
"Cindy," he said as he saw another car go by looking for a parking spot.
"This is what public humiliation is Mark."
Mark had never stepped outside the house in women's clothes before. He had gotten comfortable dressing around Cindy over the last six months.
Mark was a young twenty two year old, who liked mature women. Cindy was actually a friend of Mark's mother and she was in her early forties. Their relationship had started off quietly, with nobody knowing about the two of them but slowly had leaked out with time.
Cindy had found out about Mark's dressing and had been very understanding his desires. She would help dress him up and even ask him to dress up for her at tomes and listen to him talk of his fantasies of giggling girls looking at him or shocked women forming opinions of him based on what they saw. Cindy was the type that wanted to bring some reality to his fantasies, even surprising him at times, but keeping him safe.
Cindy opened the door and stepped out. She had to go around and open his car door as he sit there having second thoughts.
"C'mon Mark it's time. Let's go," she said helping him stand up.
Mark was wearing a dark blue sweat pants and sweat shirt with front zipper set. The hood on the sweat shirt was pulled up over his head. He also had on a pair of large, dark sun glasses.
His feet had a pair of white tennis shoes. He stood up and took the large plastic bag that said Dillards on it, and began walking to the store with Cindy. They passed several people on the way and not a single one lifted an eye at Mark. He looked like an average young hale trying to stay warm with his hands in his pockets. They walked up to the main sidewalk and detoured to the side of the store behind a wall where the dumpsters were located.
Cindy took the bag and pulled Mark over by the wall. She smiled and looked into his eyes and kissed him.
"It's time," she said reaching up slowly to take off Mark's sunglasses.
Mark's eyes were made up with dark eye shadows, and he wore false eyelashes with dark mascara and eyeliner.
Cindy smiled as she looked at the uneasiness in his body language. She undid the drawstring for the hood and opened it and pulled it off his head to reveal his hair was set in tight rows of 1" brush curlers. The pink pins were perfectly placed to make a straight line over the the top and up the sides of his head. Mark hung his head embarrassed. Cindy cupped his chin and raised his eyes to meet hers. She took a pair of gold hoop clip on earrings and attached them to his lobes. They contrasted with necklace he was already wearing.
Cindy took a tube of red lipstick and began applying it to his lips said, "Are you feeling it yet? A little nervous aren't we? Embarrassed? Afraid for someone else to see what a sissy you are?" she smiled.
She had him press his lips together then she stepped back to look at him.
"They will laugh at you when they see you, and realize you are not really a woman," she said finishing his lipstick.Mark said nothing as she unzipped his sweat top and pulled it off, followed by the breakaway sweat pants. Mark stood there wearing a white summer dress, with bright red and yellow floral print. It was sleeveless, and made of a light material. It had an elastic waist that showed his contours and a light full skirt that ended above the knee.
He was also wearing a c-cup padded bra that gave him a pronounced bustline as the dress was a tight fit in that area. Mark's legs were bare and shaved. Cindy took a pair of 4" white, high heel sandals out of the bag and Mark slipped them on. His bright red toenails were in sharp contrast and very prominent. Mark hung his head as Cindy took his hands to look at his long red fingernails and rings on his fingers.
"There," Cindy said stepping back and admiring him. She put all his stuff in the Dillards bag. She put a shoulder purse on him, and handed him the bag.
"You ready?" she laughed.
"Cindy. I can't be seen like this."
"Sure you can. I told you the first time it will be just a simple recognition. The person will not know you and you will never see them again anyway right? So what does it matter what they think," she said in the comfort of her winter coat. Mark was shivering wearing summer clothes in the 30 degree weather.
"I'm cold Cindy," he said shuffling his feet around. His nerves made the cold even more intense.
Cindy slid her warm hand under Mark's skirt and began massaging his semi erect penis. He wore no panties, and Cindy looked him in the eye with a smile She caused him to become more and more erect. She looked across the parking lot at two cars that had just pulled in.
"I think those two women would like to see you wearing your pretty dress Mark," she said grinning.
"I can't. Can we be a little less obvious," he tried to bargain with her.
"No Mark. The rollers in your hair and summer dress in freezing weather is to guarantee you are observed. I doubt they will just walk by a young lady dressed as you are without wondering about her appearance," she smiled still stroking him.
"You'll be carrying this Dillards bag with all your clothes in it, and you will look like you have been inside shopping. Then when they realize you're a man and not a woman, who has been shopping in a department store, well I'm sure they will have some sort of reaction," she looked at him with a raised eyebrow. "I know I would."
She put his skirt down now, and his erection pushed gently against it giving a slight tent effect. She then nudged him forward.
"Cindy, wait. I'm not ready to do this," he looked at her as he tottled forward in his heels.
"What's that Mark? To be publicly humiliated? Embarrassed? Laughed at by other people over your passion to dress like a girl?" she laughed.
"Please Cindy."
"Mark honey, you'll never be ready for that," she said as she pushed him into the open."Go on. Walk back to the car passed those two women who just parked. Let them see you as you walk by. I'll meet you at the car," she kissed him on the cheek. He walked out onto the sidewalk and looked back with a unsure look.
"I'll give you a blowjob once we're back in the car. Now go and show what a sissy or faggot or whatever they will think you are." She waved him off to his humiliation.
Mark stepped into the parking lot and nervously started walking toward the safety of the car. He saw the first woman had already gotten out of her car and was walking toward the mall.
Mark had his Dillards bag and his purse. A slight breeze was causing his bare arms, feet, and legs to chill even faster. Not to mention he wore no panties under his skirt. He became more excited as he approached the woman his erection now a concern for him as he noticed it pushing his skirt out even more. He breathed heavily as he walked himself into his inevitable humiliation. What would she say? What would she think of his appearance and why he would be dressed like this? His mind was racing.
As they approached each other they made eye contact from a distance and she smiled.
"Maybe she thinks I'm a woman," he thought.
Maybe the curlers were what had caught her eye. Didn't see women in major department stores with curlers in their hair, especially the way his hair was set.
She gave him a puzzled look as she approached and said, "Aren't you cold?" looking him up and down.
"I'm freezing," he said in his male voice. She gave an indifferent smile as she gave him a quick up and down look at the realization he was a man.
Mark had thought her eyes seemed to turn away from him when she saw his skirt. Was it his imagination or did she see his erection pushing against his skirt. Had she noticed? Maybe she just moved on with the fact he was a man dressed as a woman. She continued walking without another word.
Mark felt so humiliated as he had no idea what that woman must be thinking. He kept walking as the two young girls who had just gotten out of their car were now headed his way. As he approached him they both seemed to figure him quickly. With big grins on their faces and wide eyes as they walked very fast. As they got up to him they both looked out the corners of their eyes and gave a quick wave and said "Hi" as they walked by. Mark responded with a pleasant "hello". They passed him and one of them gushed out uncontrolled.
"Oh my god, that was a guy," they both laughed.
"He had curlers in his hair." He could still hear some of the remarks as the distance became greater he could only hear the outburst off laughter that continued to happen. He didn't look back and wanted to get in the car, as he walked faster now the show he was required to perform was over.
As he approached the car he looked back and Cindy was standing in front of the store talking and having a laugh with the first woman he had passed. He turned and was surprised by another woman who was just finishing putting things away in her car next to the one he was riding in. She was a thirtyish attractive woman. He stopped abruptly. She glanced up at him and said,
"You need to get some more clothes on. It's freezing out here," she smiled and then a puzzled looked overtook her face. She looked him over from his curlers to red toenails.
"Been doing some shopping this evening?" she said with a slight smile.
"Just got a few things," he said trying to move on.
"I see. You're a man. Why are you dressed like this?" she looked as if she was expecting an explanation that would make sense to her.
"I....uhm......I just needed to do some shopping," he said.
"Needed to dress like a girl to do your shopping?" she looked at his hair. "I'm sure those curlers didn't cause any unwanted attention," she looked him over as she talked.
Mark was very nervous now. He had not expected to have to have a conversation. He was just to walk by a couple of unsuspecting women and move on.
"Nobody said anything to you in the store while you were shopping?" she asked.
"No. I don't think anybody really noticed."
"Honey, if you walked in the front door of that store looking like that, I promise you everybody noticed," she looked him over again.
"I'm very cold. I think I need to go and warm up," he said with a slight laugh of nerves.
"You should have dressed properly for the evening. You're dressed for July. Your toes have turned red and I'm not talking about your nail polish," she tilted her head.
"Do your parents know you dress like this and go shopping?" she asked sounding pushy.
"I just dressed like this to come to the store," he began to make overly simple statements that were almost silly.
"Is this some kind of dare, or initiation? I mean, I know you had help. You could not have done those curlers like that by yourself," she followed him now.
"Um.......I, had my hair curled by a friend. I'm just dressed for the evening for fun," he looked away.
"Oh. OK. So you are a transvestite out for a little public frolic. Enjoying the outing?" she smiled.
"I would like to get in the car now," he said as he got to the car.
"You put yourself in front of me. For my amusement. I didn't force you to prance around in women's clothes. You know, I have a dick in my pants too. I'm a guy just like you are," she struck a suggestive pose and winked at him.
She looked so feminine. Mark was really stunned at this.
"Are you really?" he said eyes open in amazement.
"No! Do I really look like a guy?" she said and began laughing as she walked away.
It was dark now when Cindy got back to the car. Mark was inside still cold as the car wasn't running yet. Cindy slid in behind the wheel and looked at him.
"So how was your little walk miss?" she said with a giggle.
"I've never been so nervous. Those girls were laughing at me," he said looking about.
"Of course they were. What did you expect?" she slid over and took her gloves off and putting her warm hands under his skirt. She fondled his half limp dick and gave him a kiss.
"I tell you what I'm going to do. I am going to suck your dick and when it get's nice hard, I want you to get out and go stand in front of the car and masturbate," she cooed.
"Cindy! Are you crazy," he was shocked at her suggestion.
"Look at all these cars. You are standing between a lot full of empty cars, and we are far way away from the store," she smiled.
"It's dark out Mark. Jerk off and raise your skirt up high when you're ready to cum, so I can see you shoot your cum into the air and onto the ground." She smiled as she handled his semi erect dick.
"Nobody will know. I'll be watching though. Do it for me."
She then went down on him an started a rapidly sliding her warm lips up and down on his dick. The idea she had thrown out was very erotic and exciting, but the reality of standing outside in a public parking lot jerking off was more that he could agree with. The sucking felt so good though.
"OK Mark. Outside. Let's go," she said as she urged him out of the car.
"Start masturbating. Grab your dick in your hand and stroke it," she said again.
Mark was stroking himself now as she opened his door. An excitement ran through him that he didn't understand. There was nobody in sight. It was dark. He stepped out in his high heels, looked back at her and walked to the front of the car. He looked around and then he began to masturbate under his skirt as Cindy sat in the car smiling and watched. His summer dress and high heels sandals did nothing to shield him from the cold wind. His hair was in rollers, and he felt so self conscious.
Mark began stroking himself faster his eyes closing with excitement. His red toes curled under slightly as he felt the eruption coming from his loins. Mark lifted his skirt to his chin and just as he began to ejaculate, Cindy turned the car lights on. Mark was stuck in his passion throws now. His skirt pulled up and his semen shooting violently into the air in the bright lights of the car. He pulled down the skirt immediately. He was mad at her for doing that. He stomped back to the car, but Cindy had locked the door and rolled down the window just a bit so he could hear her.
"That was great Mark. You shot your cum really high in the air. It was easy to see," she grinned.
"Let me in Cindy," he grumbled.
"Didn't you enjoy that Mark. Big boy like you standing in a parking lot dressed like a girl jerking off. You must of had the time of your life," she looked serious, then a smile broke through.
"Cindy. Just let me in the car," he said again.
"Sure sweetie. Just take that dress off first," she grinned.
"I'm naked under this dress. You know that," he hissed.
"Oh Mark, stop exaggerating. You have a bra on. Just take the dress off," she smiled.
"Someone might see me naked Cindy." Mark nervously looked around.
"Oh no. A naked man wearing only high heels, in the parking lot, wearing makeup and hair curlers. How embarrassing and humiliating that would be," she laughed. "Look around you. Not a soul in sight. It's ok. Take the dress off and I'll unlock the door.
"No Cindy. This is all too much," he said in a panic.
"I see. I agree. It is a bit too much isn't it," she said as she pondered.
"How about if I give you this scarf to put over your hair curlers. That should make it much better for you," she laughed holding a scarf toward him.
"Cindy get real."
"Take the dress off Mark," she said again.
"Fine." He looked around and then he unzipped the dress and pulled it off his shoulders and let it drop to the ground. He stepped out of it and stood up naked.
"There. You happy now? Now let me in the car," he said.
"Walk around the car one time in your high heels and the door will be unlocked when you finish," she looked at him. "Well, go on."
Mark was stricken with fear at this little game she was playing. She was in a control position now. He looked around and nobody seemed to be in the area. He looked at her again as she signaled for him to get moving while she sat in the warm car. Mark put the dress on the top of the car, and then began to walk to the toward back. He walked fairly fast, his heels clicking on the pavement as he made his way around the car for Cindy's amusement. His dick hanging now rather prominently hanging and bumping about as he trotted in the heels . He picked up the pace and made it to the door. It was still locked.
"Cindy. Open the door!" he said looking in the window.
"I want the runway model walk Mark. Head held high and proud, heel over toe, and a little swing in those hips if you please. Not the I have to hurry and get in the car cause I'm naked walk." she giggled.
"No Cindy. Let me in. I'm not doing it."
"You have no problems doing the walk at home," she looked at him.
"Go on now. Head up, back straight. Once around the car, and then you can get in here where it is warm," she laughed.
Mark looked around again and began his strut to the back of the car. As he got there he looked both ways to make sure no one was coming and stepped out and walked behind the car. One foot in front of the other in those high heels, slight sway in his hips, arms very straight with hands slightly turned out. He walked past the drivers side and in front of the car again where Cindy hit him with the lights again just as he was coming from in front. When he got to the door it was unlocked. He opened the door and jumped in. Cindy was laughing as he tried to get warm.
"That wasn't funny at all Cindy," he scowled.
"Yes it was honey. It was hilarious," she said laughing.
"You need to be paraded like that more often I think. Don't you know your public awaits you?" she laughed as she started the car and backed out. They were back on the road when she asked if he had settled down yet.
"Other than I'm riding around in the car naked," he looked out the window.
"I'm lucky nobody saw me back there Cindy."
"Oh but somebody did see you. There was a older woman sitting in her car that saw you do everything in front of the headlights," she laughed.
Mark was stunned for a moment.
"She had such a shocked look on her face Mark as she was watching you jerk off. You were great," she smiled at him.
"That's why I had you do an encore performance around the car. It was so funny." she laughed out loud.
Mark had no idea that Cindy was just making that part up. Humiliation from thinking you were seen is just as bad as actually being seen, but safer. He had been brought out to experience public humiliation dressed as a woman and Cindy was making sure he was not disappointed, and enjoying herself at the same time. He was literally pushed to the edge on his first trip out. Cindy would never reveal to him that nobody had actually seen him doing those things at the car. He didn't need to know as far as she was concerned.
When they got home Cindy pulled into the garage and closed the door. She turned the ignition off and looked at Mark.
"Well? Did you enjoy it?" she looked at him smiling.
"It was quite a rush, that's for sure," he responded feeling so much more relaxed now that they were safely home.
"I was so really nervous most of the time, I was just real uptight you know? he broke a slight smile now.
"It will be so much fun to lay in bed reflecting on it. Don't you think?" she looked thoughtfully.
"Yes. Speaking of bed," he said giving her a look of desire.
"Oh my sweetie. My pussy was wondering if you had forgotten about it, with you dolled up and all." she reached over and put her hand behind his head a pulled him to her and kissed him. She rubbed his rollers with her palms as she released him.
"I'll be so glad to get these things out of my hair. What made you think to have me wear rollers instead of my wig?" He was feeling them now with his fingers.
"Mostly the look, and the looks they receive," she smiled her eyes on the rollers.
"Will you take them out first? They are very uncomfortable."
"No," she said looking at them again. "Wear them to bed tonight. Sleep in them for me. I'll take them out for you in the morning after breakfast. How's that?" she asked.
"Cindy. This is not public humiliation now. This is private irritation. I'd like to get some rest tonight if you don't mind." He gestured to the rollers.
"Sure sweetie," she said. "Would you like me to plan another little adventure for you some time?" she asked.
"Yes," he said in a bashful way.
"Whenever you think you want to do something like that, I'd like to be told and not asked," he said sheepishly with his eyes down, revealing more of his desires to her. She lifted his chin and gave him a soft kiss on the lips.
"Tomorrow morning then, after I take your rollers out, we'll take you out again for some public exposure with your hair teased up and sprayed," he started to interrupt, but she stopped him.
"The rollers stay in for the night Mark." She could see his dick starting to respond to her firm directness.
"Let's go in the house, get ready for bed, then we can have sex, and talk about your little adventure more." She looked at him now with true sexual desires of her own, like the whole evening had been a huge foreplay session for this moment.
Cindy lay on her back in the bed staring at the ceiling. She was completely naked as she relaxed. Her head was propped up on a pillow and she had one arm behind her head and the other she was rolling and gently pulling on one of her nipples. Her left leg was stretched out and her right leg pulled up with her knee in the air. She had her legs spread wide as she talked to Mark.
"I don't know which would be more fun, having you try on women's clothes in the stores or have you spend some quality time in a beauty salon," she said as she thought about new adventures for Mark.
"Let's see what do I want everyone to see when they look at you, hmmm. A crossdresser, fag, or a sissy? I think I could have a mix if I did it right." She looked down at him.
Mark lifted his roller head from between her legs. Though he was tired and had spent much time licking and sucking her pussy already, Cindy was not done yet.
"Oh no sweetie. I'll let you know when it's time," she said pushing his head back down and positioning her pussy against his lips.
"Hold still," she said as she gripped his rollers with both hands and began rubbing her pussy up and down his face. From his chin to his forehead, she humped his face for a few minutes, and gave a sigh of satisfaction.
"Gently continue sweetie. I want to read my book for a while before bed. Be sure to insert your tongue as deep in my pussy as you can as your doing it. You know I like penetration too," she said patting his head and opening her book now.
"Oh my," she smiled as Mark put his tongue in deep and also gently inserted his finger in her ass. Cindy held up the book to the lamp and read with a very happy smile on her face.
It had been a evening full of adventure for Mark. Cindy had plans for him for the morning, and all he could do was imagine what they could be. Especially after today.
Thoughts from the author:
HMMMMM..........I mean really, would a young twenty two year old man actually walk around in a mall parking lot dressed like a woman as described above and allow himself to be observed in such a way that everyone knows he is crossdressing?
Things like this can only happen in this little tale of public humiliation and perhaps maybe on that very chilly November evening in 1981, in a well lit parking lot full of cars outside Montgomery Wards in Big Town Shopping Center, Mesquite Texas. The mall was torn down in 2006.
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