Jerry Ch. 06: Getting A Do

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He gets his hair styled and mind blown.
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Part 6 of the 10 part series

Updated 06/09/2023
Created 12/29/2018
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Disclaimer: If gay or bisexual male/female sex turns you off, it would probably behoove you to skip this tale. There is a bit of incest and mild cross-dressing in here for good measure. It starts slow for series plot reasons, but gets warmer (hopefully you'll think so) before the end. Some things will make more sense if the previous chapters are read, but except for one silly mystery the reasons for things can be inferred.

The action takes place in the Silicon Valley. The places and organizations named are mentioned to give local color only. As far as I know, there is no web cam business like the one described here. So there are no actual students involved. All characters in my stories are figments of my imagination. Unfortunately.

On with the play.

*****

"How's my girl?" Tom asked when close enough to Jerry no one could hear. At least Jerry hoped not.

"Fine, but I'm not a girl," Jerry replied blushing and looking around to see if anyone heard the exchange.

"Sorry little buddy," the athlete said. He stopped jogging a couple of feet in front of Jerry. The man reached out and mussed Jerry's mop of red hair.

"Where were you? We were going to review chapter four before your test," Jerry's concern for his friend's performance was real, but he longed to talk about last night. Their lunchtime Geometry review in the library would've provided at least little time to chat.

Jerry waited in the mostly empty library for Tom to show up, but he never did. After lunch period on his way to his Physics class he saw Tom jogging in from the student parking lot.

"I had a hot lunch date," Tom said flashing his trademark grin.

"Well I hope you're ready for the test. You're getting concepts down, but proofs -" Jerry began to explain.

"Don't get your panties in a twist about it," Tom said cutting him off and clearing up a lingering mystery from the previous night.

"I can't help it. I worry about you," Jerry said adding, "You better hurry or you'll be late for the test."

"No worries, Ms. Fisher isn't back from lunch yet," Tom stated.

Just then a light green Prius drove up near where they stood and parked in a spot reserved for teachers. Jerry noticed Tom watched the person getting out of the car with interest. The person turned out to be Ms. Fisher herself. Tom turned toward Jerry and flashed his trademark grin once again.

"Told you," he said.

The two of them stood on the walkway leading to the Math teacher's classroom so there was no way she could avoid them. It seemed strange to Jerry when she passed them without a word and avoided his eyes. As her best student for the three previous years Jerry normally received a nod or a smile when they saw one another.

"That is one fine teacher," Tom said.

"I've always thought so," Jerry agreed. She only taught the standard high-school math classes, none of the Advanced ones. Jerry took only Advanced classes so their paths rarely crossed this year.

"Good luck on the test Tom," he added.

Jerry saw an unfamiliar expression steal across his friend's handsome features, uncertainty, maybe even a little embarrassment. "Little buddy I was thinking it would a good idea to end our tutoring sessions. They take up too much of your time and I'm too dumb for them to do me much good anyway," Tom said.

If Tom said anything else Jerry couldn't hear it. He was in free fall. A big hand mussed his hair again, then his friend followed the teacher. A buzzer indicating the start of the class period sounded not more than thirty feet away, but went unnoticed.

For the first time ever Jerry skipped a class and began trudging the two miles home. He couldn't think of anything except for Tom's horrible decision. True the sessions took some of his lunch hours each week, but he considered those hours the highlight of his life.

When he thought about it later, he wondered how he made it across Capitol Expressway without getting run over. He walked the familiar route home on autopilot, tears threatening to come.

Jerry entered his front door and discovered three women looking at him. He found it disconcerting to say the least. In addition to his mom and sister who shouldn't have really surprised him, Aunt Carol was there too. Though not a true aunt, as the life long friend of his mother he thought of her as one. Carol sometimes called herself Auntie as well.

His Mom and Carol sat close together on the large living room couch. Diane sat on the floor apparently doing stretching exercises. Diane wore her favorite gray sweat pants and a baggy T-shirt. The older women were dressed in matching fluffy bathrobes short enough Jerry looked away to avoid staring at their bare knees and thighs.

All three silently stared at him and he sensed his entry interrupted an intense conversation. His Mom shared Jerry's pale complexion and tendency to blush when embarrassed. Her pink cheeks showed her embarrassment now.

"Hello Jerry dear, what a surprise to see you!" Aunt Carol said.

"Hello Auntie," Jerry replied.

"Why so woebegone dear?" she asked. Obviously his despair showed.

"No reason really, I just ...," Jerry's answer trailed off as the tears began to flow. He turned to the right and rushed up the stairs as fast as his blurry sight allowed. Now he felt worse for breaking down in front of the three women.

At least the body shaking sobs were over when Diane came in and closed the door behind her. She was the one person who would understand.

"Tell me about it," she said as she sat on the edge of the bed he was sprawled across.

He told her the whole story, or at least everything he thought important.

When he finished, she ran her fingers through his hair. He wondered if she knew how pleasant and comforting it felt. She looked as if she was deep in thought.

"I think you must have left something out. I have some questions for you," she said.

Diane preceded to interrogate him asking him at least a dozen questions. He answered them the best he could, but didn't see what light they shined on his situation. What did it matter if Ms. Fisher was wearing pants or a skirt? Or, if she was wearing heels or not? Or, if she was carrying her briefcase?

Before he answered her final question, she was grinning. "How did she react to seeing you?"

"Well it was strange, she walked pass us like we weren't there," he said.

"More likely she just wished you weren't," Diane said with a laugh. "But your problem with Tom is nothing to get your panties in a twist over, that's for sure."

He left Tom's use of the phrase out of his story, so why would Diane use it? The mystery of the twisted panties went back in the unsolved X-file.

"Why not?"

"Jerry, Jerry, Jerry," she said shaking her head. "You're too naive for your own good. Tom had sex with Ms. Fisher to make sure he passed the test."

"What?" Jerry exclaimed, "That's like cheating!"

"He's just using his talents to maximize his gains, just like I did," his sister replied smiling down at him.

Jerry's mind was boggled. He listened to his sister's story of how she passed Algebra 4. He heard why Diane asked about Ms. Fisher's shoes. She said Ms. Fisher liked to dress sexy when meeting a student. Ms. Fisher wore a skirt when easy access would be required. Access given to male or female students as fancy struck her. Diane's oral use of that access was required in exchange for a passing grade.

"Don't you admire Tom's solution to his grade problem? It's the simplest and most elegant solution of them all," Diane said coming to an end of her explanation.

Of course Jerry couldn't agree with the statement. Besides the unethical aspects for both Tom and his teacher, what would the world be like if everyone did it? It seemed wrong on so many levels he couldn't count them. More to the point, by choosing to take this path Tom no longer needed his help. What did Diane mean by 'Nothing to get your panties in a twist about'? It was the exact reason his panties were in a twist.

"But I don't see how it helps me! Tom doesn't need my help anymore," Jerry said.

"He didn't break up with you silly. An ass like Tom would have said something nasty if he wanted to end what you two share," his sister said stroking his hair again. "He didn't do that did he?"

"No, I suppose not," he replied. "Are you sure?" he asked eyes searching hers.

"I'm always right," she replied with a laugh. "Wait and see. In a couple weeks, if not sooner he'll be back looking for another great blowjob."

Jerry blushed in embarrassment, but her words managed calm his fears. If his sister thought Tom would be back then he probably would be. She was usually right about people.

"Now I have to go out and I want you to go with me," Diane said standing up suddenly. "Hurry up and get ready, because we need to hurry to make it to my appointment," she added.

As she was speaking she stripped off her sweat pants and T-shirt. Jerry saw his sister in a different light since their love making last night. He felt his penis stir in his jeans at the sight of her nakedness. She gazed down at him apparently pleased at her sexual appeal, despite his gayness.

"Get up and change please. I'm serious, we have to run," she urged. "Put on your gym clothes. It's too nice outside to wear those things you have on." With that she ran out the door leaving the pile of her clothes behind.

Diane's energy seemed to infect him. He rose from the bed and within five minutes stood before the mirror fully changed. Now dressed in his new gym clothes with the too short shorts and T-shirt. Why he wore the pair of pink socks he couldn't say, but they seemed part of the outfit. His tennis shoes gleamed in white newness. No one would know he wore the lacy black panties his sister gave him last night under the shorts.

"Are you ready to go?" Diane called before sticking her head in. "Oh, good you are and you're looking good."

"So do you Sis," he replied. Diane looked stunning in a short light-weight, off-the-shoulder sun dress. Its pale yellow contrasted nicely with her bronzed skin.

"Thanks now get in my car and I'll be out in a minute," she said holding out her car key. She beeped off the car alarm and unlocked the doors of her pride and joy.

To Jerry's relief his mom and Carol weren't in the living room. He hurried from the house and climbed into his sister's red Miata. It was a rare treat for him to sit in the snug leather passenger seat. The car interior remained as spotless as the day she drove it off the lot, quite an accomplishment for Diane the slob.

He grew curious about how neat the glove compartment would be. He reached out to open it, stopping when he saw his sister come into view. She walked gracefully in a happy carefree manner with a smile on her face. Seeing her like this made him almost as happy as before the Tom incident. Irritating her by going through her glove compartment was the last thing he wanted to do.

"It's so nice I'll put the top down," she said to Jerry's dismay. As a redhead his skin could burn in no time, but he knew it wouldn't do any good to argue with her.

It took his sister three minutes to pop the latch and push the top into its storage cavity. The sudden brightness of the open sky made him squint.

"I thought of that. Here put these on," Diane said as she settled into the sports car. She took two pairs of sunglasses from the satchel which served as her purse. She took one and passed him the other. They were identical as far as he could see.

He put his pair on and immediately wondered why he didn't wear sunglasses every sunny day. He turned towards his sister and saw she was smiling at him.

"They look great on you Jerry," she said adding, "They hide your red teary eyes."

Jerry considered if comfort and disguise sufficed as reasons to wear these glasses. They were girl's sunglasses, obviously so. Sure they looked fantastic on Diane, but must look silly on him.

"Just wear them until we get there," she said.

He thought about asking where they were going in such a hurry, but it didn't really matter. The open air and warm sun on his skin worked its magic, chasing care away. Plus just to be with Diane proved a joy. He watched the pleasure she took in making the tiny car dance amongst the SUVs and eighteen wheeled behemoths on 101 then 680. To keep his nerves still he looked exclusively at his sister.

She smiled and waved at drivers who let her in front of them when changing lanes. She remained unruffled when a driver didn't. Quite different from their father whose profanity laced tirades while driving were the stuff of legend. She managed this with nimble handling of clutch, stick-shift, brake and gas petal which would forever be beyond Jerry. Her sheer competence made her sexy.

They were off the freeway on city streets when he began to take an interest in their surroundings. He knew they were near USJS, because he went to the main library from time to time with Sidney. He wasn't familiar with the residential area around the college. So he was lost when Diane pulled up into the driveway of an old, but well maintained two-story house.

"We're here," Diane announced cheerfully.

She hopped from the car and immediately put the top back up. Once Jerry placed the sunglasses on his seat she locked and set the alarm. The neighborhood looked better than their own, but Diane wasn't taking any chances. He told himself to remember not to sit on the sunglasses when getting back into the car.

Curiosity finally get the best of him and he asked, "Um, why are we here?"

"For my pedicure of course," Diane said as if it was obvious.

The Hispanic woman who opened the door appeared to be in her early thirties. Her hair cut short showed no trace of gray. He was taken aback by her attire, a white men's dress shirt. The lacy bra she wore under it could be seen since half of the shirt's buttons were undone. Her bare legs reminded him of Diane's, long and firmly muscled. On her feet were red shoes with the tallest heels ever.

He noticed this in the second or two before she threw herself into Diane's arms and hugged his sister tight. There followed much kissing and words of greeting in a mix of English and Spanish. Jerry gathered they normally saw one another more often than they had recently. It was three weeks since they'd last been together.

"Isabella, this is my little brother Jerry. Jerry this is my best friend Isabella," Diane said getting formal all of a sudden.

Isabella reached out a hand. He didn't know what to do with it, but since it was done in movies, he lifted it to his lips and gently kissed it.

"You are so gallant," she said with a warm smile.

"Come in and let's get started," she urged pulling Diane inside the house. He shyly followed them.

His mind was blown as if he fell into another dimension. He walked into a scene he could never have imagined. In the living room two of the walls were dominated by huge screens each showing people engaged in sex acts. All of them stark naked.

One screen showed two young men and a middle-aged woman. The other showed two young women and a young man. All looked extremely attractive. The sounds of sex surrounded him and he immediately became hot and light headed.

"Oh Jerry ignore those. They're just feeds of some live cam shows we have going on," Isabella said as if it would be possible for the 18-year-old to ignore sex.

"I thought my sister was here for a pedicure," he said.

"Si, she is. Sit in the usual seat Diane," Isabella said indicating a recliner on one side of the room.

The sound from the screens went off making the assault on Jerry's senses less overwhelming. He still found it impossible to ignore the images of sex and nudity. Especially the three hard cocks.

"Thanks Dan, I think it's a bit much for my brother Jerry," Diane said to someone behind him. "Jerry meet Dan, Isabella's husband."

Jerry turned and found himself facing a handsome gray-haired white man. He held a remote pointed towards the screens. He seemed tall, but almost all men were taller than Jerry. The man also seemed too old for his younger wife.

Dan took one of Jerry's hands giving it a firm shake. "Pleased to meet ya," he said.

"Dan do you have time to work some of your magic on Jerry? He really needs a haircut," Diane asked.

Dan brought a chair out of the dining room and Jerry sat on it. From his vantage point he could see Diane lounging back in the recliner while Isabella sat on a cushioned foot rest working on Diane's pretty delicate feet.

Dan draped what looked to be a checkered table cloth around Jerry. He rummaged through an old shoe box until he found a pair of long scissors. Jerry felt uncomfortable when Dan studied his head and features from all angles, using a strong hand to turn his head from side to side.

When Dan finally started to work it felt like any other haircut. The clicking of the scissors and fingers gently arranging the clumps of his hair were quite relaxing. Working in silence at first, Dan put him at ease.

"I bet you find all this a bit strange don't you Jerry?" Dan asked with a chuckle.

Without waiting for an answer Dan launched into an explanation. Beginning with the way Isabella and Diane met. It happened at the club where Diane worked and the older woman once did. Isabelle showed Diane the ins and outs of the dancer's craft.

After Isabelle retired from dancing he worked out other ways of paying the bills. One of the ways involved hosting web cam shows. The nearby college provided a never ending supple of talent and with the infrastructure in place it was a cash machine. The scheduling and payroll tracking could be brutal, but it worked out.

The screens were there so they could monitor for illegality such as drug use. The cameras for paying customers were under the control of either a director or sometimes the talent themselves. The media department at the college provided plenty of volunteers to do the behind-the-scene technical stuff. What leaves the house is much sexier than you see on these monitors.

Dan told him all this between snips of the scissors without the need for any questions or response from Jerry. It distracted him from the orgy of sex taking place on the walls, especially when Isabella would throw in a comment here and there. Something about her pleasant smiling face provided a point of normalcy to the bizarre scene.

The tale came to an end when Dan picked up a hair clipper from the shoe box. He plugged it in and used it on Jerry's hair. The loud buzzing made it impossible for him to hear anything Dan might say. Jerry watched Isabella as she worked on his sister's feet. She finished one foot and was painting the toes of the other one.

"No wonder Diane's feet always look so exquisite," he thought. He was surprised to feel himself getting stiff. He rubbed himself discreetly under the cloth.

The abrupt end of the loud buzzing and the sweeping away of the table cloth signaled the end of Dan's work. "We'll have to wait until your sister comes so she tell us if it is okay. We might as well get comfortable while we wait," Dan said as he plopped down on a couch.

For the first time Jerry noticed Dan wore a baggy pair of pajamas. Something in Jerry's expression must have alerted the older man to the shock they caused. He explained, "The business requires late nights, so we sleep in late." The older man indicated a spot next to him for Jerry to sit.

He sat next the older man, but evidently not close enough. Dan put his arm around him and pulled him closer. Jerry experienced mixed emotions when the man removed it. He felt a rush of blood to his cheeks.

"We're like two wallflowers at an orgy Jerry," Dan said, using the remote to turn the sound up on the two screens. The sounds of sex surrounded them.

Dan pointed to the screen with two men and one woman. Jerry stared at the older woman mounted on top of an younger man. Her heavy breasts hung down between their naked bodies jiggling as the man thrust up into her. Behind her large butt the other man squat, trying to put his large cock into her ass. He would stick it in managing only a couple of thrusts before it popped out.

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