Chairman of the Board

by

Zoneefem

 

Jon was a typical 14 year old junior high schooler-nothing much to brag about. At five foot five inches, he barely tipped the scales at 125 pounds. Athletics were too demanding-anyway, you had to take a shower with all the other guys who were three inches taller than he was(and maybe a couple of inches longer also). For an eighth grader, Jon's report cards were average at best-except for the computer class which was his only claim to fame. Ever since he was old enough to reach up to the keyboard on his dad's computer, he had spent almost every waking moment on that computer. He got so skilled that when his dad had a report due at work, he would get Jon to do the computer work.

One day Jon came in from school at the regular time and when he went inside, his mother met him at the door. She had obviously been crying for a long time-her eyes were red and puffy. She hugged him with all of her strength and he knew something was terribly wrong. "Jon, honey-I'm afraid your dad had a terrible accident on the way to work this morning and he didn't survive the crash. For now, you are going to have to take care of yourself until we get the financial mess he left straightened out."

"Sure mom, no problem," he bravely answered, but down in the bottom of his heart, he knew this would probably not be an easy time. His dad had been out of work for several months before finding his new job, so there would be no fringe benefits or insurance coming their way. He would just have to find himself a part-time job and work before or after school. Somehow they would manage.

A few days after the funeral, Jon decided to look for a job, but try as he might, nothing came his way. Mom was pinching pennies to make ends meet, and there was nothing extra for anything other than the basic needs.

Jon came home from his latest foray into the job market totally dejected. Oh well, maybe he could do something from the house on the computer to make a few bucks. He went into the den and turned on his dad's computer. At first what he saw on the computer homepage didn't register-must be an new effort by one of the big industry giants. But as he stared at the screen, something told him he wasn't looking at a regular web-site. In fact, this was definitely not something he had ever seen before.

About that time, his mother came home from work and walked over to Jon and gave him a big hug. She seemed preoccupied with something, but he didn't recognize her upset. "Mom, what is all of this on the computer?" "Your dad always wanted to start a home business and that is the last opportunity he ever looked at," mom replied. "It is some kind of gadgets. He told me he had set up part of a website and was going to start taking orders as soon as he could get it set up with a server. I don't know if he ever got to actually sell anything."

Jon had never really looked into e-commerce, but he had certainly heard about the opportunities available on the net. "Okay if I fiddle around with it?" "Sure son, I really don't know anything about this, but have yourself a ball." Mom went on into the kitchen and began cooking supper.

A bit later, Jon was still fooling around with the computer when mom came back into the room. She slowly walked over and put her arms around Jon. "Son, I lost my job today, and within a few weeks, we will probably have to move. There is no way I can pay the bills to live in this nice house. Maybe we can get enough from selling it to keep us going until I find another job."

"Hmm, what is this email from Interweb Direct Shippers? Must be a mistake -it refers to a check ready to deposit into dad's bank account." "Bound to be wrong son. Since there won't be much to come in, why don't you have them send the check to your savings account at the bank. Maybe it will help us through the tough times ahead." So Jon dutifully dashed off an email to Interweb,. with instructions to deposit the money into his savings account.

When he arrived home the next day, Jon was surprised to find a voice mail message from Mr. Jones, the bank president. He explained that customers substantially increasing their balances received special bank privileges and told Jon if he ever need anything to give him a call. He also said that he really had enjoyed his "shipment" and the "merchandise" was really nice. Well, apparently Mr. Jones must have purchased something from Jon's dad's new website. Great, maybe a small commission would be forthcoming.

A few days later, Jon decided to go by the bank and check his balance. His dad's computer hard drive had some problems and appeared to be overloaded with stuff. All of the junk email had apparently caused it to run so slowly, it was almost frozen. When he arrived, Mr. Jones walked out of his office and shook his hand. He was sorry to hear about Jon's dad, but glad that everything looked okay. Jon was confused-he knew how desperate things were for his mom. How could Mr. Jones think things were okay?

"I just need to get a few dollars out of my account to purchase a new hard drive. Hope there is enough in there for that." At that point, Mr. Jones grinned and winked. "No problem. Why don't you go see one of my customers who is in the computer sales business and get one of those up to date computers. They can't be all that much." Jon didn't want to miss taking advantage of an opportunity. Maybe the banker was going to loan him the money and because Mr. Jones referred him, he would get a super price.

"Tell you what, Jon, I'll talk to my computer gal and have her place the order. We'll be sure you get exactly what you need and debit your account. Okay?"

"Sure thing, Mr. Jones." Jon shook his hand and walked out the door. No need to stay and waste the bankers' time. When the saw his savings account balance, they would probably call him and cancel the order anyway.

The next morning as he was going out the door to go to school, he saw a "Freightways" truck parked across the front of his drive, blocking his access. "Say driver, could you move this truck?" "Okay son, just as soon as I deliver these boxes to this house. Obviously a mistaken address, but Jon kept his mouth shut and opened the door for the deliveryman. He signed for the boxes and the driver left.

Hmmm, he mused, wonder what all this stuff is. Then he remembered that Mr. Jones' secretary had ordered a computer for him, and maybe they had sent it out overnight. At least he would get to look at the new computer before sending it back. No way he could afford a new CPU and 21 inch screen flat monitor. And that new 32xx lazer printer was way out of his league.

After he got to school, his conscience began to bother him for letting Mr. Jones at the bank send him all of that top of the line stuff, so as soon as he had a break, he placed a quick call to the bank. "Mr. Jones please," he told the receptionist. "Who's calling ," was the reply. "Jon Johnson." "One minute Mr. Johnson, I'll find him for you. Oh, he''s in a board meeting-I'll put you right through." Soon the voice on the other end said, "I'm sorry, he's not available, may I tell him who called?" Jon told her, and right away she told him to hold on, Mr. Jones would be right with him. This seemed very odd, but oh, well, whatever.

"Jon, my boy, I'm glad you called. I was meeting with the board and your name came up. We have approved a small line of credit on your behalf to help you though settling you father's affairs. Feel free to draft on us for whatever you need." Wow, this guy was bending over backwards to help Jon and his mom out. "Thanks, Mr. Jones, but I'm not sure how I can accept this for now. Things at our house are a bit unsettled." "Don't worry about a thing, Jon, I'll cover this for you. Call if the line isn't enough."

Now Jon was really flustered-why would Mr. Jones be so super nice to him? On the way home, he thought just for fun he would stop and look at a new MP3 player. The new ones were really nice, but of course way out of his budget. When the saleman asked him if he was interested, he said sure, and just for kicks had him call the bank for approval. Jon was preoccupied just cruising around the store, so when the clerk walked up to him and handed him a package, he knew this had to be a mistake. "Thanks Mr. Johnson, and if there's anything else you need, please come by. I usually don't get to sell that top-of-the-line model these days." Jon was perplexed, but said thanks and walked out the door(fully expecting the shoplifting alarm to go off).

When he got home, mom was sitting in the middle of the living room with his unopened computer packages stacked in the corner. "Son, you know we cannot afford this, why did you order them?" Then, noticing his package containing the MP3 player, she started crying. "Jon, have you stolen someone's identity? Did you shoplift that? Why are you doing this to me? You know we can't afford this."

What had seemed to be a fun idea suddenly got very serious and sad. "I'm sorry, mom, but the banker Mr. Jones insisted that I buy the new computer. He even arranged a line of credit to help us settle dad's affairs. How could I say no?"

Mom immediately started crying. She knew that they needed help, and perhaps the few hundred dollar line of credit would get them through the tough times ahead. "Son, you can keep what you have for now, but realize we will soon have to return it. If I didn't need that line of credit I would send it all back today, but since the amount of loan is so small, let's keep it for now, but no more purchases-understand?" "Sure mom, I'm sorry. It just seemed too good to be true. I won't use it again."

That seemed to make mom happy for now, so Jon gathered up the computer and other boxes of stuff which had come this morning and headed up to his room. When he finished unpacking the new computer, he really was confused. This was no cheap computer-it had all of the bells and whistles. The monitor was a 21 inch super color flat screen. Jon had read about the computer but it had always been way out of his budget. In fact, the computer in the school office wasn't anywhere near this fancy. He was really going to miss this when they had to return it.

The next day when he got home from school, there was a service repair person waiting to install a new computer hookup. A T-4? Oh well, he could use the new computer to do all sort of things and he knew the T-4 had to be a mistake. For now he let the guy install the hookup and plug the new computer into the jack. The speed was incredible. He now had the fastest computer in town. Maybe he wouldn't say anything to mom about the T-4 connection. It would all go away soon enough anyhow.

When the phone rang a bit later, it was the banker asking whether his T-4 hookup was satisfactory. "Sure," Jon replied, "thanks". "By the way," Mr. Jones continued, "I received my second shipment today. It was all very nice. Thanks." Jon was now totally confused, but didn't want to irritate Mr. Jones, so he just said "you're welcome" and hung up and went on upstairs to his room.

It had been several weeks since Jon had been in his mom's bottom dresser drawer. Mom wasn't due home for several more hours, so he knew he could spend a bit of time without being interrupted. As the bureau opened, Jon carefully reached in and caressed the pile of soft, colorful silky panties. He picked up his favorite pair-a gorgeous pink with embroidered flowers around the waistband. Mom sure had a good eye for beauty. The label said "100% imported silk", and Jon knew from looking through the mail order catalog that this was the most expensive kind of panty available. Not only was this pair pretty and soft, there were many other pairs in different hues made of the same material.

Mom must have been very well off at some point in her life to afford so many pairs of undergarments. The next drawer up was full of matching bra's. Above that were the negligee's and again, they all matched the colors in the panty drawer. Jon slowly took the gorgeous pink panties and slid them across his face. So soft. He could feel a stiffening arousal in his pants, then felt the gooey come begin to leak into his underpants.

What he didn't see was his mom standing just outside the door watching him caress his chin, then slowly raise the panties to his nose while he breathed through the material. She had come in a bit early and had been on her way up to change clothes. Rather than embarrass Jon, she quietly sneaked back downstairs and loudly slammed the front door. "Honey, I'm home," she called out, "when you get a second, come on down here."

Jon was so startled he quickly threw the pants back in the drawer and ran out of mom's room.

Mom was sitting in the living room when Jon arrived downstairs. She seemed deep in thought, and when he popped into the room, she brightened up a bit. "Come over here and sit by me son," she told him. "It is time we had a serious talk about something that you need to know." "Sure, mom," he replied as he sat on the couch next to her. "What's up? Another problem?"

"Jon, your dad was a wonderful man. He did all he could for us to see that we had everything we needed. Hard work was not a problem for him. But, he had one side that you never knew about. He loved to dress in women's clothing. He wasn't gay. You know that bureau in my room with all of the nice panties and matching bras'? Those belonged to your dad. I know that you may have similar feelings about dressing in women's clothing, and if you ever want to talk about them, please let me know. I just don't want you feeling like you have to hide what you feel between us at home."

Jon reacted as if he had been shot with a bullet. Could this be true? He had just been up in mom's room caressing those panties. This was awful.

"Mom, I didn't want to tell you, but I do have that kind of feelings. I was just up in your room looking at those panties and bra's. Are you telling me those were dad's?" "Son, there is nothing better than the truth between us-your dad was a crossdresser and had been one all of his life. He was a wonderful husband and father, and that was just a small part of his being that he really enjoyed. Your feelings along that line are okay by me, and if you want to experiment with dressing up as a female, I will not only give you my permission, but will also help you do it the right way. When you are ready to give it a try, please let me participate. There are a lot of things you will need to know to experience the true feminine feelings you are seeking." Jon couldn't believe what he had just heard come out of his mom's mouth-she not only accepted his urges, she volunteered to help him do it right.

They embraced each other tightly for a long time, just sitting on the couch. Mom seemed relieved that the subject had finally been discussed and Jon knew that from now on, he wouldn't have to hide his true desires. After a while, mom suggested that Jon go upstairs and take a nice hot bath. Tonight was to be a special time they would both remember.

The water was steamy and Jon's young skin turned bright pink from the heat. After a time, mom knocked on the door and handed him three bottles containing skin softner,her favorite shampoo and a conditioner. "Be sure to rinse your hair thoroughly when you get out of the tub, and wrap this oversize bath towel around your hair. We will dry it later." As she looked at her 14 year old son in the hot bath, her eyes began to water. How many times she had done the same thing for her husband. They had such good times together. She closed the door and Jon realized that their relationship was now totally different-it would never be the same again.
After he finished rising his hair the second time, Jon applied the conditioner and according to instructions, waited five minutes to rinse it out. He then wrapped a towel around his head and walked to his mother's room. She told him to come in and have a seat at her dresser, and removing the towel from his head, draped it over his shoulders. Taking her good scissors, the trimmed his bangs to eyebrow level, and then notched the fringe to outline the line of fall.

Mom lovingly ran her hand through his now squeaky hair and saw that he had followed her instructions to clean it completely. Next, she took a long pointed comb and separated out a small portion of his hair. Then she wrapped it around a large hair roller down to the scalp and secured it with an aluminum clamp, and proceeded to roll the remainder in the same manner.

When she was finished, she pulled a large oversize hairnet and tied it in the rear. Soon Jon was seated under a hair dryer and he had trouble staying awake. Mom handed him a couple of magazines which contained pictures of girls and young women trying on clothes, makeup and hairdo's. Before he finished the first book, the dryer turned off.

Mom removed the net and then unhooked the clamps holding the rollers. Jon's hair stayed in springy coils. Taking her hairbrush, she combed thru the curls and soon had a funny looking comb attacking each strand by sliding the comb backwards toward the scalp. After a few minutes, she picked up the hairspray and "sssssst", soon the hair was in place and brushed into a very feminine style. It fell just above his collar and flipped up on the ends. Jon loved it!

Mom then went into her closet and returned with a lovely A-line skirt. It was one of her favorites and the hem came to just above Jon's knees. "Your dad loved this skirt-in fact he picked it out for me. He said it called attention to my legs." A beautiful silky blouse was also on a separate hanger. "You are almost my size." She also handed him a matching bra and panty set and suggested he go into the bathroom to put them on.

She watched as his now lovely curls bounced up and down when he walked. Just as he got to the door, the towel around his waist gave way, and mom couldn't help seeing his now engourged penis in its full glory. Just like his dad.

Jon slipped into the panties and decided to stuff the bra with toilet paper. Then, looking in the mirror, he was amazed to see a young teenaged girl staring back at him. Wow, could this be him? Then he slipped on the blouse and buttoned it up to the neck. Since he had never worn a skirt, he called mom to help. She stood behind him as he twisted and turned. She was amused at his efforts to straighten the skirt, and after watching him struggle for a while, she reached her arms around him to grab the waistband to relocate it. Ooops, she pulled on something that turned out not to be his skirt. At that point, Jon began to experience his first orgasm ever-it was almost painful. Mom quickly pulled away and Jon could feel his beautiful panties getting wet with his cum. "I'm sorry mom, I just couldn't help it." "That's okay son, its not your fault. Why don't you go ahead and take a quick shower while I get you another pair of underpants."

After mom had Jon try on several other sets of clothes, she reached into the bottom left drawer and pulled out a gorgeous babydoll nightie. "This was your dad's and he would have wanted you to have it. Let's put some more hairspray on your hair and tomorrow it will still look fine."

Jon was very tired-this had been a big night for him. Finding out that his father was a crossdresser; having his mother help him get dressed in feminine garb and experiencing his first orgasm. He went to his room wearing his dad's favorite nightie and tried to fall asleep, but he was too excited. After tossing and turning for almost an hour, he climbed out of his bed and tiptoed across the floor to mom's bedroom door. When he failed to find mom in her bed, he tiptoed downstairs to the den. Jon could hear her on the phone talking to someone, but she was almost whispering so he couldn't quite hear what she was saying or to whom.

Saturday morning quickly rolled around. He had decided to sleep later than his usual seven thirty schooldays wake up time, but at seven sharp, mom shook him awake. "Jon, you cannot see the full effect of dressing until it is done properly with the assistance of an expert in hair and makeup. So, slip on this pair of jeans and white blouse and come downstairs right away."

When Jon arrived downstairs, he was surprised to see his Aunt. Ellen Brooks was dad's favorite sister. Jon was still half asleep, so this all was a total surprise to him.

"Eat a very light breakfast and we will go," she said. "My friend's entire staff of hairstylists and aestheticians are waiting on you at the beauty shop. Don't worry about clothes-you are fine for right now."

"Okay, I guess," but I need to check my email. Ellen said, "Alright, but hurry, we don't want to keep the "Beautycrew" waiting."

Jon rushed over to his computer and within seconds he had retrieved numerous emails and he had another phone message from someone at the bank-a Mrs. Smith saying something like, "thanks for banking with us." Something was going on, but he was still sleepy, so whatever it was couldn't be too important. He did notice another "shipments made and check deposited directly to your account" message, but then he expected it to be a few bucks commission, so he just deleted the message and left to join Aunt Ellen in her car.

They drove for several miles in silence until Aunt Ellen cleared her throat-"hrrump". Jon, you know I was your dad's favorite sister, right?" "Yes, and he was always telling me about how much he respected what you had accomplished in your career and homelife. He was so proud."

Aunt Ellen's eyes began to tear up, so she wheeled into a parking lot for a couple of minutes while she tried to gain control of her emotions. "Did you ever suspect that your dad was a crossdresser, Jon?" "No, I guess I was just too busy with other things," he replied. "Your dad was very special to me, Jon, and I would have done anything for him. Now that he is gone, you are next in line to carry on the family tradition. Well, lets get this car back on the road. We don't want to keep the staff of Beautycrew waiting."

  

  

  

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