It was shortly after his sixteenth birthday that Ian discovered that he had the desire to wear female clothing, but not just any clothing, it had to be silk and or satin. He thought maybe it was a phase that he was going through. He figured if I ignored these desires they would pass. Ignoring them didn't work and they became more intense.
He often found himself sitting and staring at the large Sears catalog lingerie section with the same intensity as he once perused the toy section. The images on the slick pages of full and half slips, nylons, and garter belts along with the various wigs and nightgowns always got him as hard as a rock and he sat wishing he had some of them to try on.
Wishing was all one could do. This was the sixties and there was no internet so there was no online ordering. A young man attempting to purchase lingerie was sure to raise eyebrows.
Now his longtime buddy Gene also loved these same articles of clothing, except he had no desire to wear them. He wanted to lay with a girl that was clad in them. Now they weren't bad-looking teens but were very shy around the girls at school. So Gene's hopes were for naught. All they had was their desires, imaginations, and masturbation.
Ian remembered telling his buddy about the black half-slip and matching panties that he had recently shoplifted from a specialty shop when he was forced to accompany his Mom on a shopping trip.
"I wear them at night when I jerk off," he confessed.
As Gene and he were sharing embarrassing secrets that afternoon, Gene disclosed the fact that he had rescued one of his sister's silky nighties from the rag bag.
"I beat off into it almost every night," he admitted.
"It was a good thing I don't have a sister as a lot of her lingerie would be missing, " I told him after his revelation.
Gene fixed him with a slight smile before continuing.
"So you're saying that if some of her clothing disappeared and wound up over here you would wear them?" he asked in a trembling voice.
"Yes," Ian responded in an excited voice.
"Would you let me see you wearing them?" Gene asked.
"Of course," Ian responded.
Now Gene spent a lot of time at his house as he was the only male child in his family. They didn't hang out with the neighborhood kids very often as they all wanted to play baseball or some other such sports. They preferred to read, watch television, and play board games. Sometimes Gene borrowed one of his Dad's Playboy magazines and the teens devoured the pictures within.
Once Gene discovered that his Dad's file cabinet was unlocked and he came across an 8mm porno film from his Father's collection and brought it over. Ian would set up the old movie projector and they would watch the grainy frames of couples doing the down-and-dirty. Afterward, they would have great discussions about girls they wanted to perform those acts with.
Now in their childhood, they had built a fort in the corner of Ian's basement from three old refrigerator boxes and it became a variety of housing for the characters when we played. Ian was even allowed to sleep in it one night as he had outfitted it with an old sleeping bag, blanket, and pillow.
When they outgrew the place, they didn't throw it out but kept it together because Ian often hid there when he needed to be alone. It was shortly after school ended for the Spring break that Ian's Mom called him to the phone one evening, his buddy was on the other end.
"I have something for you," he said.
Ian's teenage prick jumped as he spoke the words.
"What did you get?" Ian asked barely able to keep his voice low.
"You will have to wait and see for yourself. So when should I bring them over?" he asked.
"Tomorrow," was all Ian said. "Mom's going shopping and Grandma is babysitting so we can use the fort."
The next day he flew to admit him when Ian saw him walking up the driveway with a shopping bag. He was met at the door and the bag was taken to our fort, he resisted the temptation to look inside. They lingered upstairs until Mom was getting ready to leave, she gave the speech about behaving and making enough noise to wake the baby.
As soon as Mom backed out of the driveway Gene and Ian headed downstairs. Gene occupied himself playing on the pool table while Ian entered the old fort. Once inside he could no longer stand upright, so Ian grabbed the bag and walked on his knees to the back of the fort. He emptied the contents of the bag and his hard prick almost tore through his jeans.
