To everyone else, it was just a garage sale in one of the wealthier suburbs, but to seventeen-year-old Monte, it was the hopes of a dream finally coming true. There were ten tables on the driveway and the garage apron that were filled with above-average bric-a-brac, but these items were of no interest to him. He still stopped and gave them a passing look so he didn't look too anxious and to alleviate suspicion of anyone watching him as he moved closer to the garage door and there were the racks of clothing he had seen yesterday morning.
Monte's summer job was for a landscaping company. Besides the pay which was pretty good for the time, the work kept him in shape and helped him with his tan. Plus it also allowed him to see how the rich folks lived as the company had many accounts in this part of the "burbs". It was while tending the lawn next door to this lavish home that he had seen the racks of clothing being wheeled out and his sharp eye caught the shimmer of silk in the early morning sun.
The sign on the front lawn said the sale would start on Saturday and end on Sunday and as Monte had Sunday off he planned to attend and hopefully fulfill the longtime desire that burned in his heart.
He was now in arm's length from one of the racks and his heart leaped with joy for it was still packed with a collection of long silky robes and nighties in all manner of material that he had ever seen outside of a catalog. He allowed his fingers to gently trail across the sleeves of this collection as he stood there examining the clothing.
Just the touch of the cool silky material against his fingers sent a shock through his body and caused his cock to tingle and he looked around to ensure no one was paying attention to him because this was the sixties and any young man that wished to dress and act like a female was packed off to a shrink.
Now Monte had no idea where this desire came from but soon it was too strong to ignore. Anytime he came across a magazine that featured pictures of sexy ladies in their lingerie Monte could not tear his eyes away. The sight of the shimmer of silk, satin, and nylon against naked flesh always got him excited and filled him with the desire to wear them.
Now he had no sisters that he could borrow from and he couldn't bring himself to steal from his mother, so he did without for a long time. Finally, out of desperation, he shoplifted a pair of panties from a local department store and masturbated into them every night.
He fell asleep after each session with his cum-soaked panties wrapped around his slowly deflating cock and had the greatest dreams. In his dream, he saw himself dressed in the silkiest and sheerest fabrics imaginable and he looked and felt one hundred percent female.
"Beautiful aren't they?" he heard a voice ask from behind him.
Monte wheeled about and spotted a handsome older male seated in a lawn chair. By the coin changer on his belt, Monte reasoned that the male was the homeowner.
"They are beyond beautiful," Monte responded trying to keep his voice low.
"Look at the labels, they are not department store trash," the man continued.
Monte grabbed a few necklines and examined the labels, the male was correct. They bore the names of some of the top-of-the-line lingerie companies that he had read about in various publications. He returned to the male but further comments were withheld when a female attendee approached with some items in her hands.
"The whole neighborhood is going to miss you," the woman stated as the male made change for the bill she handed him.
"I'll be back in the summer," was his response.
They hugged briefly and then left.
"Allow me to introduce myself, I'm Jay," the male said as he extended his hand.
Monte took the offered hand and introduced himself.
"If you look behind the curtain you will find some other interesting items," Jay stated.
Monte parted the curtain and pushed them aside and stepped into the garage. There on the trunk of the car parked there and displayed on a white sheet was a collection of nylon stockings, garter belts, and panties, in every material and style imaginable. Monte felt his cock beginning to tingle as he examined these items.