Grant returned to his room on rubbery legs due to his recent masturbation session. Clad in his sister's nightie, panties, and pantyhose while he masturbated gave him the most intense orgasm that he had ever experienced up to that time. He thought about the nightgown that he had worn, washed, and hidden in the basement and decided not to return it to his sister's room.

Since his sister admitted that she no longer wore them, he was sure that it wouldn't be missed. He would recover it and hide it in his room and maybe wear it to bed one night when he was sure that there was no chance of being disturbed in the morning. He then questioned himself about this temptation. He had no desire to be with a man or to wear makeup, as there was no way he could be made up to look female. No, he was happy just to feel the silky clothing against his body.

On his next trip to the basement, he headed to the rack that held his mom's and sister's clothing. These were older and out-of-fashion dresses, skirts, and blouses that were still in excellent condition and had been earmarked for donation. Since his parents and sister were not home yet he took his time examining these hanging garments.

There were a few silky almost see-through black blouses with tiny buttons along with some white ones. The blouses shared the rack with numerous dresses in all styles, but again they held no interest to Grant once he discovered the sheer blouse. He then came across the skirts and the tingling in his groin began.

The skirts were in a wide variety of colors and styles, there were minis and knee-length. He found a few pleated skirts among them similar to what cheerleaders wear and a few that had a small slit that allowed the wearer to show off a little more thigh, he selected one pleated one in a deep blue. He then grabbed the sheer white blouse and hid them where he was sure that no one could find them, then hastened to his sister's room.

Grant then went straight to the drawer that held her pantyhose where he dug out the thigh-high stocking and garter, these he hid in his room. Later that night he fired up his laptop and searched on how to wear nylons and a garter belt, he was not disappointed.

The temptation was on him but he resisted as this wasn't the proper time. His family would be home soon and he didn't want to risk discovery, so he ignored the urge to dress up.

The opportunity to submit to his temptation presented itself that weekend. His parents were going golfing and his sister was heading out with a group of her friends. Grant blew off invites from his buddies to hang out telling them he wasn't feeling well.  As soon as the house was silent Grant decided it was time.

His first stop was the master bathroom where he dug out his razor and shaving cream. The sight of his hairy legs under the pantyhose spoiled the illusion, so he decided to remove the hair. With careful strokes, we ran his razor the length of his legs as the internet had shown him.

He then recovered all the items he had hidden and was soon in the basement. Grant then stripped down naked and began to dress. First came the nylon stockings. Following the instruction he had seen online he commenced to cover his newly shaved legs with them. Just the sight and sensation of drawing the filmy stockings up his legs had him as hard as a rock but he managed to will it away. A pair of her clean panties were taken from the laundry basket and he slowly slid them up his nylon-clad legs enjoying the sight and feeling.

The panties were black in color and buttery soft and the moment they touched his cock and balls his erection began to return, and once again he willed it away. He found a bra that was also black among her clean clothes and quickly fastened it around his chest. He solved the problem of the empty cups by stuffing them with her clean pantyhose and was pleased with the results.

Grant became excited at the look and feel of his fake boobs and couldn't resist running his hands over the silken cups. He then reached for the blouse and slowly slipped an arm into one of the sleeves. The feeling of the cool silk against his warm flesh caused his cock to jump, he then inserted the other arm and proceeded to button the blouse.

Next, he stepped into the short skirt and pulled it up, and then zipped it. It was even shorter than he imagined and showed off a lot more leg. Grant then headed to the old padded chair and the dresser with the faded mirror and took a moment to admire himself.

His legs covered in the mesh cloth of the nylons looked as good as any of the girls at school. He ran his hands down his front brushing the phony breasts hidden under the silky blouse, they looked and felt as real as any he had touched. Grant then did a pirouette causing his short skirt to flair up and reveal more of his nylon-covered thighs and part of his butt.

Finally, the pressure of his hard cock against the silky panties became too much and Grant decided not to delay the next step any longer, that is when the idea hit him. He headed to the old padded chair and with some difficulty pushed it so it was in front of the dresser. He then angled the mirror downward as far as it would go.

Grant then took a seat and remembered to smooth the back of his skirt as he's seen the girls at school do before his butt was in the seat. The reflection in the mirror only showed from his neck down. He kept his knees together at first and enjoyed the sight and feeling of his hands running up and down his nylon-clad legs before he slowly spread his legs open and draped them over the padded arms.

Grant ran his hands up and down his nylon-clad legs a few times before he gently seized the hemline of his skirt and gently pulled it up until the tops of his nylons and crotch were exposed and he took a moment to admire the sight. He then encircled his hard cock that was pressing against his panties and began to masturbate right through his panties.

His free hand went to his chest where he gently squeezed his makeshift breasts and enjoyed the sensation of the pantyhose tucked into the cups rubbing against his hard man nipples. His hand left his breasts and went to the waistband of his panties and he stopped long enough to tug them down far enough so the head of his cock was exposed.

The sight and feeling were too much for his senses and a massive orgasm took control. He didn't close his eyes but watched as his cock spewed all over his panties and skirt, only then did he lay back in the chair and enjoy the after-effects. 

A half an hour later his cock began to thicken again and he quickly removed his cum stained panties. Grant then grasped his erection and began to slowly masturbate again. This time when the end was near he manages to point his throbbing erection toward the tops of his nylons where he released himself onto the lace tops of his stockings.

Later after putting the basement back in order he removed his sister's clothing in preparation for washing them. He didn't know where this temptation came from but was happy that he was able to fulfill it.