Jerry Ch. 08: Day's End

Mom comes home early.

Disclaimer: The action at the heart of this tale is incestuous but the story brings in elements which deserve a warning. There are male bisexual and cross-dressing things happening here. If those ideas bother you, then you should skip this one. This story can be understood without reading the previous chapters, but I hope you will take the time to read them.

All characters are over 18.

On with the play.

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"Are you going to be late for work?" Jerry asked his sister Diane. She had to be at the club in Sunnyvale by seven o'clock and it was almost six. With the terrible traffic it would be next to impossible for her to make it.

"It'll work out somehow," she replied as she pulled into their driveway.

It never ceased to amaze him how laid back his sister could be. He would be frantic in her situation. Climbing out of her sports car he saw his friend Sidney come into view. The tall gangly teenager had probably been waiting on the porch for them to arrive.

"See, problem solved," said Diane as she strode towards the front door. "Nice to see you again Sidney," she said when she came up to the black bespectacled youth.

"Nice to see you too," the 18-year-old replied in a monotone voice. His eyes scanned her body from head to toe. Her sundress it did little to hide her figure from his gaze.

"Come inside while I get ready. I have a favor to ask," she said as she passed.

She didn't even turn to see if he would follow. She seemed sure of her power over Sidney.

Instead of following sexy Diane, Sidney gawked open mouthed at him. Earlier in the afternoon Jerry experienced a less extreme version of the stare from another black man. That one at least managed to keep his mouth from gaping. Sidney lacked certain social graces.

"Hi Sidney," he said in greeting.

"Wow. Jerry you look ... nice," said his friend in an emotionless voice. "Really, really nice."

"Thanks." Apparently he did, since the girl's shorts, T-shirt and sunglasses he wore made men stare at him with lust in their eyes. He liked the attention. It made a pleasant change from his usual invisibility.

"I looked everywhere for you after school. Then nobody was here. Where did you go?" Sidney asked.

"I didn't feel very good so I came home early," Jerry replied with a half truth. The last thing he wanted to do was get into a Q-and-A about Tom. Besides after all his adventures the Tom incident didn't seem quite so painful anymore.

"I like your new haircut. It looks like Servalan's," Sidney said. Jerry realized the truth of the remark. His hair was a redhead version of the style worn by the villain in the old-school science fiction TV show, Blake's 7. The character was very much a woman.

Diane disappeared into the house in a rush leaving the front door open. He followed with Sidney trailing behind. On the living room floor lay his sister's pale yellow dress, which meant she was naked. From upstairs he heard the shower turn on. His sister was cleaning up for work.

"Sidney where are you?" Her voice came from on high.

Jerry turned to urge his friend to go upstairs. Sidney was staring at his bare legs and rubbing a long pipe-like bulge running down one pants leg. It looked extremely long and thick. A couple of days ago he'd watched Sidney ejaculate massively in his pants without even touching himself.

"Sidney!" called Diane.

Jerry pictured himself dropping to his knees, undoing Sidney's belt, yanking down the pants and releasing his friend's huge cock. But his sister would not take kindly to him detaining the solution to her problem. He didn't understand how, but it was clear Sidney played a big part.

"Hey Sidney. Sidney!" Jerry resorted to shouting to get his friend's attention.

"You don't have to yell," Sidney said in a flat tone, finally looking up.

"My sister needs your help. Go upstairs and see what she wants please," he said.

"Okay, but you look ... nice," Sidney said as he passed by Jerry and climbed the stairs.

The shower shut off and the glass door rolled open as he followed his friend up. Sidney stopped on reaching the top of the stairs and stared towards the bathroom. On reaching the top too he saw why his friend was staring. Diane stood outside the shower dripping wet. Except for a white plastic shower-cap she was naked. With her luxurious mane tucked away she appeared completely hairless, her groin was shaved smooth.

After giving both of them an eyeful of her beauty, she reached for a big fluffy towel and began to rub herself dry.

"Sidney could you ride along with me when I drive to work?" she asked in a silky voice. She ran the towel on her shoulder blades sawing the towel back and forth. This displayed her large firm breasts to perfection. The twin pink nipples were fully erect.

"Um, I don't know," Sidney replied.

"I can use the carpool lane if you do," Diane explained her reasoning. She whipped off the shower-cap letting her honey-blond hair cascade about her soft shoulders. Jerry could see she was putting all her goddess-like loveliness into her sales pitch.

"Where do you work?" his friend asked.

"The Panther Club on -," she began, but Sidney cut her off.

"I've seen it. It's near Fry's in Sunnyvale right?" he said.

"That's the one. How about it Sidney dear? I'm sure there's a bus stop near the club," she said, giving Sidney a chance to show off the specialized knowledge which made him a true nerd.

Even standing behind Sidney, Jerry knew what his friend's expression showed. It would have Sidney's usual look of deep thought. Eyes looking up to the right, tongue sticking slightly out of the left corner of the mouth. It would be the same face Sidney made since childhood.

His friend's obsession was public transportation. He carried all of VTAs routes and schedules in his head. This was in addition to the usual Sci-Fi stuff expected of a high-school nerd. Sidney retrieved the required information in the time it took Diane to seductively dry one long tanned leg.

"Yes, there is a stop close to the club. I could catch the 26, transfer to the 522, then to the 61. I could be home by nine-thirty," he announced in his emotionless tone.

"You are amazing Sidney. You have a beautiful mind," Diane said.

Jerry doubted Diane's hold on his friend would be powerful enough to convince Sidney give up an entire evening. Even the sensuous manner in which she dried her other elegant leg wouldn't do the trick. As she'd done with the first, she placed her dainty foot on the toilet seat in a wicked arch. Then rubbed the painted toes dry, the arch and heel, then up along her firmly muscled calf. All the while her perfect firm round naked ass pointed at them.

"I guess I could go with you," Sidney droned.

"Oh goody! You're a lifesaver Sidney," Diane cried out. She tossed the towel down, pranced up to the tall awkward teen and threw her slender arms around him. Jerry felt disappointed.

"Maybe I can take care of your not so little problem once we are safely in the carpool lane," Diane said in a low sexy voice while one arm disappeared from Jerry's view.

"O ... kay," came the response from Sidney. Jerry knew where her hand had gone.

"Poor Jerry was hoping for a hat-trick," Diane said smiling as she disengaged from Sidney and hurried into her room.

"What?" he asked.

"Score three goals in one game," came the answer, surprisingly from Sidney.

Staring at his friend Jerry asked, "How do you know that?" Sports talk was a foreign language to him and he assumed to Sidney as well.

"I am a huge Sharks fan. Go Sharks," Sidney said in the same flat tone.

"That's the first I've of it," Jerry said in wonder at this news.

"I guess we all have secrets," came the rejoinder.

Jerry blushed brightly for the first time since arriving home. First because his secret was no longer hidden from his best friend. Sidney had witnessed him giving Tom a blowjob a couple of days ago. Second because his sister was right. He hoped to get a chance to suck Sidney's huge cock. He remained pretty sure he'd get a chance at some point, but three cocks in one day would've been prime.

'But two is a prime number too,' he thought. This a brought a measure of comfort.

"Grab a towel Sidney. I don't want you getting cum on my leather seats," Diane called from her room.

His friend displayed uncharacteristic speed in going into the bathroom and finding a clean towel. Sidney also gathered up the bottle of body lotion from the counter. "For lubrication," he said.

Diane stepped from her room dressed for work, or a least for her commute to work. As a dancer she undressed for work. She wore another short dress, this one blue and clingy. On her feet were sensible pumps with low heels, but in her hand were a glossy red pair with at least four inch heels.

"Would you please carry these for me Sidney? Try not to get them covered in drool," She said handing them to the wide-eyed teenager.

"Sure," Sidney replied as he took them. He held them as if they were sacred objects.

She held out a medium sized duffel bag for him to carry as well. "These are just some odds and ends for my costumes," she explained.

"Hope you have a quiet relaxing evening Jerry," said Diane, blowing him a kiss. "We're off."

Jerry watched the two go down the stairs leaving him alone at the top. He hoped to the last Sidney might change his mind and stay. He sighed when the front door closed behind them. It wasn't the first Friday night he would spend alone.

Maybe he could use the time to catch on of his favorite shows, or watch a movie if he could decide on one. A wild idea popped into his head. He could go to the school and watch the big football game. He knew he would see Tom playing for their team, but the other aspects of the game held no appeal. He wouldn't know a good play from a bad play. Then there was the crowd, the noise and before the end of the game, the cold he'd have to deal with.

No it would be much better to stay home. He opened his bedroom door and was taken aback by the flood of light streaming through the windows. The late day sun turned the East foothills bright and golden. Against the clear blue sky they shone as if on fire. When the light didn't bother his eyes, he realized he still wore the sunglasses his sister gave him.

He walked to his desk, flipped open his laptop and powered it up. Taking off the sunglasses brightened up his world. This day certainly resembled a roller-coaster ride. High as a kite at the start, to the plains of Mordor at mid-day. Thanks to his time in his sister's world he felt like a new man. Even if the new man looked like a girl.

Waiting for his laptop to boot, he turned toward his bed and saw a couple of shopping bags. One was a Macy's bag and the other fancy pink with a light-blue 'Pink' on the side. He went to look in the Macy's bag first. Inside he found a note. He recognized his mom's handwriting and read:

Dearest Jerry,

I hope you are feeling better.

Just a few things I thought you might like.

I'll see you soon!

Love,

Mom XOXO

He figured it would probably be new underwear or socks. He was half-right. There were several pairs of low cut socks in the bag. They were girl's, much like the one's he wore now. There were many colors to choose from. He wondered how his mom knew he liked them. Then he remembered he was wearing the pink ones when she saw him asleep with his sister last night.

Digging under the socks he found three pairs of pantyhose. Berkshire Ultra Sheer Control Top. His wiener stiffened at the sight of the white, black and nude colored hose. Since he watched his mom put some on for her date awhile back, he wondered what they would feel like. His sister didn't own any and as tempting as it was, he couldn't go through his mother's things. Now thanks to his mom. he could wear his very own.

He started to rip open the package of the nude hose and then remembered the pink bag. On top of whatever was inside he found another note. He read:

Hello Jerry,

I was so sad to see you upset this afternoon.

Hope you're feeling better.

New clothes always cheer me up,

so I got you some things.

Love,

Auntie

Inside the bag he found a leopard skin thong, a pair of faded demin shorts, a Pink brand tank top, and most surprising of all a black sports bra. All of the items were obviously girl's clothes. He wondered why Aunt Carol would buy them for him. All of the women in his life seemed to be playing the same game.

He realized he should feel thankful for auntie's gift, but he felt a bit confused. The thong looked interesting, but he couldn't really see himself wearing leopard skin anything. The tank top and short looked comfortable, but hardly practical for a guy. What in the world did he need a sports bra for?

He would try them on, but he needed to shower first so he wouldn't mess them up. Maybe auntie could take them back and get her money back if they didn't fit, or looked too silly.

It took longer to shower than usual and he wasted water shamelessly. With the hot water cascading on his naked flesh his thoughts turned to the plethora of cocks he'd seen today. Counting them took time since he pictured each one. Dan's beautiful curved one, the three nameless dicks seen on the monitors, Esteban's lovely member, Roger's smooth one, deep voice's large one and finally Bob's big black cock, made a total of eight. Three of them he either touched or sucked or both.

If only he'd seen Sidney's it would've been nine, the third perfect square. That number seemed significant somehow. Maybe because of the talk of a hat-trick.

Reentering his bedroom naked, his slender body was squeaky clean even if his mind wasn't. His upright penis revealed the track his thoughts were on. He knew he shouldn't start stroking it right away. He wanted to enjoy the long evening alone with his pantyhose, but first he must try on auntie's gifts.

Jerry sat on the bed and put each foot into the thong. There was no mistaking front and back with this thing. He stood to pull them up and they fit snugly. The head of his erection stuck out the top band, but they would do a better job at containing his erection than the lacy panties his sister gave him.

The thong ran up his butt-crack which would take some getting use to. On the plus side his ass cheeks were totally bare. This too would take time to get use to, but it felt great already. He stepped over to the mirror on the door. The leopard print and black straps looked fantastic against his pale skin. He had to admit Aunt Carol got it right.

Looking over his shoulder while walking back to the bed, he studied his naked butt cheeks. The twin orbs were separated by a narrow line of black fabric. The black waist band crossed above them like the bar on a 'T'.

He slipped on the demin shorts. The edges of the legs looked like those of cutoffs, but were neatly done. They were short enough the white fabric pockets could be seen hanging below the edge. They were much shorter than his gym shorts.

The pink tank top emblazoned with 'LOVE PINK' in white was even more girly than the Bebe shirt which caused so much confusion at BJ's. Of course guys hadn't worn cutoffs as short as these since the seventies. Seeing pictures of grandpa in his silly cutoffs always made Diane howl with laughter. So if Jerry wore these shorts he might as well wear the tank top too.

It felt loose and too big for his slender frame at first. His reflection showed it was more a question of the style then size. The arm openings were large enough they left his sides bare almost to the bottom of his ribs. He could see his nipples if he moved the wrong way. He could see where the sports bra would come in handy to conceal them.

Now he needed shoes to go with the outfit. He knew how his tennis shoes would look with it. Men's shoes with such a girly getup would be incongruous. He decided to check out his sister's extensive collect of footwear. He picked up the T-shirt and sweat pants Diane dropped on the floor earlier in the day. He could use the clean up to justify his entry and rummaging through her closet.

He tried on a pair of her sneakers first, but they were too small. Even though she was taller, Diane's feet were smaller than his. This drastically cut down the number of shoes he could wear. The ones without backs would probably work. For some reason Diane called them her mules. He always noticed when she wore them, especially the high heeled pairs.

There were many pairs of backless shoes in her closest in a variety of styles and colors. He wondered how his sister could decide which pair she was going to wear. It would drive him crazy. Thinking about it logically he chose the color first, white. This narrowed it down to three pairs, low, medium and high heels.

As much as he'd like to try the highest heels he knew better. He would probably fall and break his neck. So he picked the medium heels to try first. He sat on Diane's bed and stuck his toes into each of the glossy white shoes. His toes felt crammed in the pointed toe box. It was worst when he stood up.

When he caught sight of himself in the mirror he was stunned. His legs looked down right sexy. He couldn't believe the difference the shoes made. His legs appeared longer and calfs fuller. He tried to turn around and look over his shoulder to see what they looked like from behind, but he almost fell over. It would take practice to be able to walk in them, much less prance like his sister did.

He carefully and somewhat painfully walked back to his room. The light from the window was now gray. His evening alone was speeding by. He wanted to enjoy the pantyhose for a good long time. He kicked off the shoes and shimmied out of the shorts. He tossed the tank top on his bed and took off the thong.

Standing naked in the gathering gloom he tingled with excitement. He picked up the package of nude pantyhose and tore a hole in one corner.

"I'm home!" His mother called from the front door.

"Darn," he said softly. He would have used a stronger curse word if he was the swearing type.

"Are you home Jerry dear?"

"Yes Mom. I'm in my room," he replied tossing the package back on the bed. He began looking for something to coverup with, but all he could see laying around were girl's clothes.

"Oh that sister of yours always leaves a mess," his mom sighed. He heard her steps on the stairs. This surprised him since he figured she would immediately change out of her work clothes. He urgently searched for something to wear. His inability to make a quick decision betrayed him. When his mom reached the top of the stairs he was still naked.

"Hello Mom, you're home early," he said blushing, one hand covering his stiff penis.

His mom tossed his sister's sundress into Diane's room and smiled at him. She came into his room and flicked on the lights.

"I took off early so I could keep you company. You looked pretty upset this afternoon. How do you feel now?" she asked.

"I feel much better thanks to Diane," he smiled, thinking of his cock-sucking adventures.

"Oh good! It looks like you got a little too much sun," she said. "Do you want me to put lotion on it?"

Jerry remembered seeing the sunburn, but he didn't feel it. His mom often rubbed lotion on his burns when he was little. He enjoyed her gentle touch as the lotion cooled the inner heat in his flesh. Thinking about it now, stark naked in front of her the heat came not from the burn, but from his boner.

She wore a white nurse's dress which came down to the knees, but her voluptuous figure filled the modest dress spectacularly. Her womanly hips made her waist look small. So did her large breasts. He noticed she wore white hose on her shapely legs. The sensible shoes on her feet were meant for comfort not sexual appeal. Her auburn mane was pinned up in a bun topped off by a white nurses cap.