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Taking That First Step free porn video
Lance was seated on a bench on the tree-lined sidewalk waiting for the store to open. Despite the warm morning air he began to sweat and his heart pounded in his chest, this was a bold step for him. Now, this particular store was located in an older but still very popular outdoor shopping center despite the malls springing up everywhere. It was commonly referred to as a specialty shop, their specialty was women's lingerie.
Before he knew it he saw the attractive saleslady approach the door and unlock it. She gave him a brief smile as she flipped over the sign that informed everyone that the store was now open.
Lance fought the urge to forget this and leave, but another force made him stand and enter the store. The saleslady noted that he appeared nervous but determined as he slowly walked around the display tables and racks of sexy lingerie, he was like a kid in a toy store.
Lance had finally had it with borrowing his sister's clothing, mostly because he had been almost caught. He still didn't know where this desire to dress up came from, but soon it was too strong to ignore. So when the house was empty he would head to his sister's room and borrow pieces of her lingerie.
He loved the feeling of the cool silky garments against his bare skin and how his cock jumped with anticipation as he slid the silky panties up his legs. He couldn't wait until his cock and balls were bound in the silk and lace cocoon. His own nipples grew hard as he placed one of her bras on his flat chest. Lance loved how his whole body quivered as he allowed one of her full slips to cascade slowly down his body.
He would then sit on the floor in front of her full-size mirror and slid the borrowed panties down just enough to allow his cock to spring fee. Once exposed he grasped it and began to jerk off at the sight and feeling of his body in the silky lingerie. This went on for months until a few weekends ago when he was almost caught.
He was already dressed and in her room and was about to take his place on the floor when he heard the side door slam and his sister's voice call out. He managed to dart from her bedroom still clad in the borrowed lingerie and head to his room, with only seconds to spare he managed to jump into bed and pull the covers over himself. A heartbeat later his sister ascended the stairs and tapped on his door.
That close call was when he decided that he needed his own stash. Now borrowing his sister's clothing was so much easier than this. With the exception of breasts and some curves she was his height and build, so he knew everything she owned would fit him well. The problem was that she didn't own too many of the things that he really wanted to wear, so he made the decision to go shopping.
He had been saving his money from his part-time job for the last several months so he could pay in cash and not write a check. Now there would be there nothing that bore his name and address on it. So his only major concern was being seen entering this store. His friends knew that he was not seeing anyone so he could not lie and say her was buying for his girlfriend.
Lance had staked out this store for about two weeks and knew the entire staff on sight and the hours they worked. He, however, waited until early Saturday morning when he knew that the attractive older female was the only person on duty.
"Good morning, Can I assist you in finding something?" she asked coming around from behind the counter.
She was even prettier and taller up close than she was through the window, and he was finally able to read her name tag, it read Cassandra. Just her presence and the scent of her perfume caused his throat to close and his practiced response sounded strangled.
"Yes. I want to pick out some sexy things for my girlfriend," he responded.
Cassandra casually appraised this young man. He was slender and not bad looking, plus he had the kind of smooth and flawless complexion that any girl would kill for.
"Anything in particular?" Cassandra asked.
Lance timidly pointed to a black silk garter belt trimmed with black lace displayed on a mannequin torsos.
"You have excellent taste. Do you know her waist size?" she commented.
Lance mentally scolded himself for not writing down his sister's sizes, he knew women sizes were different than men. His courage began to fade.
"No, I don't. I'll have to come back," he said as a look of disappointment crossed his face as he turned to leave.
"Nonsense. I can figure it out if you give me some basic information," she informed him when she saw his smile fade.
Lance halted in his tracks and turned to face Cassandra.
"Now would you say that her waist size similar to yours?" she asked.
"Yes," he responded.
Cassandra produced a tape measure from behind the counter and had him step through the curtains one the other side of the shop and into one of the private fitting rooms. Once out of the public area Lance relaxed and didn't flinch when she wrapped it around his waist. She mentally marked the size and then went through the curtains to one of the many drawers under the counter.
She returned holding the item he selected and Lance's heart skipped a beat when she showed it to him.
"This is part of a set that comes with a matching bra and panty. Can I assume you do not have her bust size?" she asked.
"No, I don't. Is that a problem?"
"No, not really. It depends on of her torso and breast size. Now is she built like you?"
"Kind of," was all he answered.
" Okay, now are her breasts are as big as mine?" Cassandra asked as she gently rubbed her fingertips over her breasts.
"Maybe a little smaller," Lance responded unable to tear his eyes off of her white silk blouse.
Once again she went through the curtain and shortly returned with a bra that matched the garter belt. Lance's erection pushed against his jeans as Cassandra showed it to him.
"Now what kind of panties would you, I mean she like. Brief or bikini?" Cassandra asked.
"Bikini," he responded without hesitation.
Cassandra smiled as she headed back through the curtains and returned with a matching bikini panty that matched the bra and garter belt.
"Now to complete this ensemble all you need, I mean all she will need are a pair of nylons.I can assume she does not own any?" Cassandra asked.
"Yes."
"Does she have big feet or really long legs?"
"She is my height and can wear my tennis shoes," Lance reported.
Cassandra had him remove his tennis shoes and she checked out the size listed inside. She disappeared through the curtains and returned with a sealed package of black nylon stockings.She opened the package and withdrew one them and showed one of them to Lance.
Lance was hard as a rock and couldn't wait to get them home. Cassandra sensed his excitement and smiled.
"Now the only other problem does she know how to don them," Cassandra explained.
"There is a certain way?"
"Yes, there is. You don't, I mean she doesn't want to tear through them. Does she?"
While Lance struggled with an answer Cassandra went through the curtains again. He peeked through the opening and saw her flip the sign and lock the door. She paused once back inside the curtains and pulled them together tight.
"Now we won't be interrupted," she said with a smile when she returned.
"What happens if the owner or manager should show up?" was the only thing Lance could think to say.
"She's already here," Cassandra responded with a smile.
As Lance fumbled for a response Cassandra took a seat and asked him to do the same.
"Now how would you like to have these things for free?" she asked.
"I'd love it. What's the catch?"
"Honest answers are the catch. Can I safely assume that there is no girlfriend and these things are for you?"
"Yes," Lance responded with his cheeks reddening.
"Good, Now now stand up and strip off your clothing," she commanded softly.
"Why?" Lance responded standing up.
"So I can show you the proper way to wear these items," Cassandra responded.
"It's not my first time dressing up," Lance informed her.
"Have you ever worn a garter belt and nylons?" she asked him.
"No."
"Then you need to learn the proper way," Cassandra responded with a warm smile.
When Lance didn't move Cassandra approached him and gently pulled him to his feet. Once he was standing she began to pull his shirt out of his pants. His erection had wilted when she suggested he remove his clothing. but it began to return as her small hands pulled at his shirt. He held his arms up so she could pull the shirt over his head.
She ran her silky hands across the expanse of his naked chest, it was smooth and free of hair. Cassandra then moved to his waist where she began to unbuckle his belt. The feeling of her silk blouse against his skin and the heat of her breasts as through the silky material caused his own nipples to get hard.
Cassandra unzipped his fly and slid his pants down his legs. She noted that even his legs were also free of hair as she helped him step out of his jeans, she then instructed him to remove his socks. Lance was now standing in front of this attractive older female clad only in his boxers, he began to feel ill.
All that vanished when she began to unbutton her blouse. Once removed it revealed a bra similar to the one she had brought him, and the color returned to his cheeks. She then handed Lance the bra she had brought in and helped him donned it. She adjusted the straps and it felt good on him.
From a small drawer, she produced some padding and inserted them into the empty cups. The bra now fit him even better than ever and as he ran his hands over the now full silky cups.He had never thought about stuffing one of the bras he borrowed.
Cassandra smiled as she unzipped her skirt and stepped out of it. Lance discovered that underneath it, she wore a garter belt holding up black nylons. She then handed him the garter belt he had selected and showed him the proper way to wear it. The only problem was that the waistband of his boxers was in the way, she asked him to take them off.
When Lance didn't move Cassandra approached him and pushed her chest against his. She allowed her hands to drift toward his waistband and began to gently tug down his boxers. Lance panicked and felt embarrassed, he moved his hands to his waist to stop her.
"You need to relax," she said in a soft soothing voice with her beautiful face just inches from his.
Cassandra removed her hands from his waistband and wrapped her arms around him. She then placed her soft full lips against his cheek began to plant kisses kiss there. She moved to his other cheek and that's when Lance wrapped his arms around her and pulled her closer.
Cassandra then moved her lips to his and a long tongue kiss followed. As they sucked at each other tongues she allowed her hand to slid down and encircle his erect cock, it was as hard as steel. Lance moaned at her touch.
She released him and had him sit on one of the padded chairs. She grabbed the nylons and sat in the chair next to him.Cassandra handed him one and took the other one.
"Now do as I do," she instructed.
Lance watched as she rolled the filmy garment down to just above the toe line, he did the same. She instructed him to slowly insert his foot into the toe of the stocking and explained how to roll it back up. Inch by inch the bare flesh of his leg was slowly covered by the stocking, she stopped him when he reached the top of his thigh.
He was instructed to repeat the same movement on his other leg. Cassandra then showed him on how to attach the tops to the ribbons of the garter belt. He was then handed the black bikini panty and told to slide them on.
"This is the only proper way to wear these, no matter what you've seen in pictures," Cassandra said softly.
Lance slowly drew on the bikini panty and it barely covered his erect cock. Cassandra told him to go look in the mirror and she admired his silk covered ass as he walked by. As Lance stood in front of the three-way mirror and admired himself Cassandra appeared at his side carrying a pair of high heels.
These will make your legs look even better," she informed him.
"I tried it once and almost broke my nose when I fell to the floor," he responded.
"That's because you had no one to help you," she responded.
Lance leaned one hand on the mirrored surface as Cassandra knelt and slid the heels on his nylon clad feet. She stood up and offered her hand for support. Lance could not believe how great his legs looked wearing heels. He was then slowly led back to the chair as she offered instructions on walking while wearing heels.
Lance loved the feel of his nylons brushing against each other as he walked. Once seated he gently crossed his legs moved one against the other and enjoyed the sensation. He was even more excited by the sight of his feet clad in sexy high heels.
Cassandra stood in front of his chair and admired the sight of him, the lingerie look good on him.
"So now what usually happens?" she asked.
Without hesitation, Lance told her about sitting in front of the mirror and masturbating.
"Well there's the mirror," she said pointing.
Maybe it was the need for release that vanished his normal shyness. Lance managed to rise to his feet and walk to the mirror again. He was amazed that he didn't trip or stumble in his heels as he walked across the room and took his place in front of the mirror.
The minute he was in place Cassandra surprised by taking a seat on the floor behind him. He could feel her silky bra pressed against his naked back and her own long nylon covered legs against his.He was about to grab his cock and commence with his routine when Cassandra stopped him.
"Please, allow me," she said in his ear as her hand gently grasped his hard cock.
Lance didn't protest and allowed her to begin gently masturbate him. She kissed his ears and neck as she manipulated his teenage cock. He was encouraged to run his hands all over her legs as she continued jerking him off. Between the feeling and sight of his own legs clad in nylons and feel of the heat of her legs under her nylons, it didn't take long before he was ready to finish.
"I'm going to cum," he managed to say.
"Then cum for me," Cassandra repeated a few times as she increased her hand motion on his cock.
Less than ten seconds later Lance released himself all over the carpet and his own legs. He felt Cassandra's body shudder as he ejaculated. They remained on the floor for the longest time before Cassandra slid away from him and stood up, she helped him to stand in his heels and they returned to their chairs.
She dug out a cigarette and lit it and smiled at Lance.
"I have always been turned on by pretty boys in women's lingerie," she admitted.
"You've done this before? " Lance questioned.
"Only in my mind," she responded.
"Now next week I want you to be here two hours earlier than you normally show up," Cassandra requested.
"You've seen me?" Lance questioned.
"From day one. I was hoping you'd find the courage to come in" she responded with a smile.
She began to redress and Lance stood to remove his lingerie and dress.
"Take off only the bra. You can't be seen arriving home boasting a B cup."
So Lance pulled his jeans up over his nylons, garter belt, and semen soaked panties.It excited him to have these girly items under his street clothes. When he extracted a wad of cash from his pocket Cassandra stopped him.
"Save your money.You can spend it on the nightie I will pick out for you to wear next week," She informed him.
They shared one more long kiss before she let him out the back door.
Lance smiled as he walked home. It was the knowledge of what he had on under his jeans that caused his smile, that and the anticipation of what next Saturday would bring.
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- 23.04.2020
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