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.