Jack's Misadventures

MichelleCD

 

This Saturday morning, Jack who was usually a late sleeper, lay quietly in bed feigning sleep till he finally heard the sound that he had that he had waited to hear since being awoke with the sound with had awoke from his slumber. This was the sound of Sandy his wife getting an early start on her trip to her sisters house with the kids for the weekend.

 

Cindy had asked if Sandy and the kids would like to stay in their house during the weekend, while she and Larry took off for the weekend. Larry's boss had offered to let Larry use his cabin for the weekend.

Cindy was hesitant to leave her house because there had been rash of break-ins in the neighborhood while the owners were away, Cindy and Larry had just purchased the house earlier this spring and it was everything they ever wanted. The previous owners had built a spa and swimming pool and enclosed a deck to make useable the year around. Larry had suggested that they invite Jack, Sandy and the kids to watch the house while they were gone. Sandy told Cindy that they would be glad to help her. Jack backed out at the last minute and told her to go ahead and go.

Sandy reluctantly agreed to Jack's suggestion, although she still felt uncomfortable about having her kids alone with the problems that the neighborhood had been having.

Sandy started her car and warned the kids not to argue during the trip or promise or not they turn around and head back toward home. Backing out the driveway Sandy started on long drive to Cindy's.

Jack listened till he heard Cindy's leave, eagerly he head for the garage and quickly open the trunk of his car in the garage. He was going to have the weekend at to himself... Peering into the trunk; Jack found the sacks of items that he had purchased the day before.

Jack grabbed the bags and headed back the bedroom and eagerly emptied their contents on the queen size bed. The sacks contain various items. Several expensive bra's with matching panties, a couple of short and long tailored skirts, with shoes and boots. Jack examines the two pair of fashion jeans in his size. The clerk at the store in the mall on the other side of town had complemented Jack on the way that the fit of the jeans. Next he emptied the contents of the other sack which held sexy lingerie and stockings with attachable breast form and tush padding the clerk had called it. The last sack contained several small boxes. Each contained different styles and colors of wigs and accessories.

Jack had planned everything carefully and had even found several restaurants and clubs where transgendered were welcome. This was going to be weekend to remember he thought to himself.

Jack looked for the last bag which contained the needed makeup and other items to prepare for tonight's adventure. Then he remembered that it was the last thing that he had purchased and it was still under the front seat of the car.

After turning on the water he head for the garage and opened the car door and removed the bag from under the seat. Returning to the bathroom, Jack removed his clothes and picked up the bottle of nair and head into the shower. Jack carefully rubbed the nair onto his skin and carefully covered the hair attached to his private parts. After leaving it on for the suggest time he stepped up to showerhead which had been deliberately pointed away from his lathered body. Jack felt the water bead down on his body as the foam slide down his body. Finishing the shower he took a dry towel down from the rack and began drying his surprising smooth skin. Using the palm of his hand he felt of his now smooth skin. Its texture surprised him, smooth as a new born babe. He took Sandy lotion off the counter and rubbed it all over his body. Taking the electric razor he shaved his face as close as he could. He rummage through Sandy's drawer and took out a new razor to get an even closer shave. He picked up the bottle of shaving lotion and applied it to his freshly shaved face and shaved the remaining stubble until his face felt smooth to the touch The girl at the adult book store had suggest that he use a beard cover and then apply the makeup.

Jack applied the makeup and smoothed it out on his skin until he achieved the right look. A masterpiece in progress he thought to himself…Next he sculpted his eyebrows until he achieved the right look. After trimming them he applied carefully the eyebrow pencil and highlighted the desired areas. Looking in the mirror he could barely recognize himself. He finished off the eyes with shadow and mascara. This change was exciting him. Until now his only cross-dressing experience had been Sandy dressing him in one of her baby dolls with a little lipstick for a little spice during sex. This was when he realized that he like the feel of lingerie and the way it made him feel. Jack had forgotten Blush and "borrowed" Sandy's Next he capped off the look with red lipstick and a choker to hide the "Adams apple". Finishing the makeup job Jack looked at his creation. He had always taken care of his body and now it showed. Unless you knew it was him then you would never have recognize a male in that face. He looked that good.

Jack sit on the bed and carefully slipped into the pantyhose he removed from the bag and finish up by slipping on the panties he had bought over them. Jack took the newly purchase breast forms and following the instructions applied to his skin and waited patiently for them to dry in place. When he was certain they were through secure he stood up feeling the unfamiliar wait on his chest. So this is how it feels to have tits. He walked over to the bedroom mirror and pear at his creation, himself. I look good, I really look good. I never thought I would be able to pull this of so well. Next he took the corset and slipped it over his smooth skin fitted into place. And adjusted in to give him the hourglass type figure and zipped up the zipper. As he zipped it he felt him breathing capacity decrease. This gave him an awesome figure.

The only thing that was left to do was find the appropriate outfit and wig to wear to the to the beauty appointment. The girl at the adult shop had arranged an appointment for me at her friend's beauty shop.

Jack decide to look for the proper outfit to wear is his wife's closet. He slipped into a print dress that would be proper for daytime wear. It was a perfect fit. He could wear his wife clothes. He continued to rummage and found a purse which he took his license out of his pocket and put into the clutch bag which he put inside the purse. He also removed his debit and several credit cards. Look in the mirror wearing his wife dress he realized something. His wife could be his sister with brown shoulder length wig that draped his shoulders they could have been nearly twins. Jack went downstairs and opened the car door for his first adventure as Adrienne, as he had so renamed himself. For some reason the garage door would not open. He climbed out of the car and walked over to the manual switch that didn't work either. Oh my god, he thought to himself he has set door so that would have to be opened from the outside and now he knew what he would have to do. Go outside and open it with the override key. He went back into the kitchen got the key; and after making sure now no one was outside, went directly the security lock and disabled the safety lock. And raised door maintaining his balance in the heels he was wearing. He walked back and opened the door of his car and heard familiar exhaust sound that meant that Caroline, Sandy's friend and their next neighbor was returning from an errand.

Jack had not thought about this when he was formulating his plan. He just hoped that she hadn't seen him and would investigate why his garage door was open. Well it is too late now he as he climbed and in behind the wheel, dropped the visor and checked his makeup. It still looked great. With that he turned the key and the engine roared to life. Putting it in reverse he back up out of the garage. Caroline stood in her yard and look toward Jack's car as he back out. The window tint obscured her view. As he backed out he closed the garage with the door opener and head down toward his appointment.

Caroline thought to herself. , now I know why Jack wanted to stay home. Quite a dish he has got their and Sandy doesn't have a clue. Caroline searched for the number that Sandy had left to call in case there were any problems she dialed Cindy's number and reach the call blocker and left her number for Sandy to call. Well, she thought to herself I have done all I can. She forwarded her number to her cell phone in case Sandy tried to call while she was running errands. Sandy notices the blinking light on the phone beside her and picked up the phone and the caller id showed a number that was familiar to Sandy. It was Caroline's number. Sandy wonder aloud, "I wonder what Caroline wants; guess I better call her and see what is on her mind." Sandy picked up the phone and called the number that was shown on the phone. She heard a couple of clicks and a message that the cell number she was calling was temporarily unavailable. "Guess I'll try later"; Sandy said to herself. Sandy layed back down in the chair and let her scantily bikini covered body absorb the rays through the clear glass roof of the cabana while the children enjoy the water and splashing each other.

As the afternoon waned Sandy awoke and decided on a quick dip in the pool. She climbed on the board and dove elegantly into the water. She swam a couple of laps and climbed out of the pool. Her nipples were visibly hardened by the brief swim and the air hitting them as she left the pool. As she headed toward the house to change; she glanced toward the phone to see if her friend had called back. Sandy went into the guest bedroom and removed her damp swimsuit and climbed into the shower to wash the chlorine from the pool off. As the water beat down on her the pulsating stream began to arouse her and she began to manipulate her aroused, moist and enlarged clit until she worked herself into an orgasm. Standing in the shower she writhed as her body experience several waves of passion each orgasm was more intense than the last until they became a total body experience. Recovering from her orgasm, she quickly rinsed off and climbed out of the shower. Clad only in a towel she pressed the intercom and pressed the pool room button and told the kids to get out of the pool and get dressed.

As she walked by the phone she glanced to see if Caroline had called back. The message light still remained dark. Guess if must not be too important or she would have called back.

A thought entered Sandy's head as she passed the master bedroom where her sister and her husband. Slept and made love. A fragrant scent permeated the room, sometime type of floral smell. You know I bet that the Cindy is spending a fair share of dear old hubby's, money on lingerie and accessories. I wonder if we are still the same size. Sandy entered the bedroom and headed for her sisters dresser. Opening the top drawer should found it divided into two sections one for panties and other bra's. Sandy looked at the panties and bra's and found a matched set that were sinfully erotic. The panties were black with red embroidery saying simple "I'm a Tease". Sandy took them and stepped in thong style panties and placed her arms into straps of the front closure bra which was red trimmed in black. Sandy closed the bra and looked into the dressing room mirror. "I still have an awesome body", she chuckled. Sandy looked in the next drawer and found a matching bustier slipped it around her waist and zipped the hidden zipper in the front. Her breast exploded with cleavage and hourglass figure expressing itself. Sandy found stockings in the next drawer and several items she had not expected.

The rest of the drawer contained whips, tie downs, a gaff and attachable breast forms next to a can of spray adhesive. The bottom drawer contained lingerie similar to the type she was wearing only in size large. "So Larry had a little secret didn't he she mused" Larry was Cindy's love slave. The next drawer contained several blouses and skirts neatly folded the size showed that these too were probably for Larry...

Sandy carefully rolled the stockings up each leg, making sure that seams in the back were straight. When she finished she looked in the mirror and exclaimed. God I look good, maybe I'll go out tonight. She knew that Kellie, Cindy's next neighbor was home from college and loved the sound of the stereo DVD and the wide screen TV in the den. I wonder she is busy tonight. Cindy quickly applied her makeup and borrowed her sister jeans and a t-shirt and jogged over to Kellie's to found out if she was busy.

Jack arrived at the address a few minutes early and walked into to the deserted shop. He was the only person there. The girl in the shop introduced herself and said, "I quit taking appointments early; I thought that since this was your first makeover you might be more comfortable if we are alone." "The girl in the shop said that her friend had done several males and had gotten excellent results", Jack said. "We did an awesome job, I can make he really look convincing as a she". You would pass 95% percent of the time. Now I need to teach you a few little secrets that will change you facial style. Men have different shaped heads than women, but with a little magic no one will be able to tell you're not female.

Your voice timber might need a little training. The secret is not what you say but how you express it. Try this say little and speak from her throat not your chest.

"I will teach you to say hello do you have my table they way that I think it should sound and teach how to say it", Diane said. I followed her lead and spoke the way that I thought it would sound and after listening to the tape of my voice and then change my speaking patterns. Now I would be able speak with a feminine intonation. Diane, persuaded me to let her double pierce each ear and told me to put earrings in both holes and asked me pick the ones I wanted her to put in my ears.

Each bleed a little but soon stopped. She picked studs for the top holes. I took the earring I had taken from my wife jewelry and a matching necklace. This set was one of the few things that I had splurged on and since bought better jewelry where these were now just an afterthought when she pick jewelry to wear.

Diane fitted the diamond studs and drop earrings into their fresh holes and draped the necklace around his neck. Out the drawer she pulled a chocker that matched the earrings. Next took the wig that I had brought with me and carefully styled it for me and place the chocker around his neck. The subtle changes she made in the makeup and style of the wig hide the last vestiges of maleness in my face. Diane asked what name I had adopted for my second self. "I said that, "I have chosen the name of a goddess in story that read in a book once; Adrienne. Having finished the makeup she began to create my nails layer by layer. At first I thought about how I would explain long sculptured nails to Sandy, but I was entrance by the elegant look and feel as she applied polish carefully to the nails. The ruby colored polish gave the long nails an erotic look.

Next Dianne placed Jack's feet is warm water to let them soak. After his feet had soak for a while, she began to massage what appeared to contain crystals. Jack looked toward Diane and before he could ask, she told him that, "this compound was made up of salt from the Dead Sea and held remarkable powers of regeneration." Finishing the treatment she manicured my toenails and applied polish. When she was finished he stood and looked at the change in me. She realized by the look in my eyes that I could never go back. Even I had come to this conclusion. I made a beautiful woman.

How much do I owe Jack ask...? Looking into my eyes she said simply "my treat Miss.

Now that you have reached the top of your mountain you can't go back, it is your choice to make." I stood there and thought about making her take money, but realize quickly my efforts her in vane. "Go change and have your night on the town but down be surprised it you become the center of attention because my dear are drop dead gorgeous truly the goddess Adrienne. Diane said. With that she instructed me on how to put on the wig and she had styled.

I looked on the watch of my wrist and realized I had just enough time to go home and change and get ready for the evening. As I walked toward the car my steps became more feminine and natural. Each step I took had a sexy feminine sway. Driving home gave me the opportunity to practice the lessons Diane had given me. By the time I reached the driveway I had it down to a science. When I drove into the driveway I looked to see if any was watching me as drove into the garage and closed the garage door..

Exiting the car, I took wig from car and carried it in to the house. Reaching the bedroom I hurried removed the clothes I was wearing and head to the dresser and grabbed stockings and changed into my wife best lingerie and full length black bustier that had only been worn once. This took about four inches off my waist and created a very flattering cleavage. I attached the stockings and headed to the closet to find the perfect outfit.

Caroline left the movie she had decided to see while running errands at the mall. Taking out her cell phone she noticed that it discharged while she was in the movie. "I guess I will have to wait till I get home and change the cell phone battery to find out if Sandy has tried to call me." Leaving the mall, Caroline opened her car door and slid into the car seat and drove home.

Knocking on Kellie's door, she heard someone open the door and Kellie open door surprise to see Sandy. "What are doing in town", Kellie said. "I am house-sitting for Cindy and Larry. Are you busy tonight," Sandy inquired... "I decide since Jack decided to make me come by myself that I would treat myself to dinner and a little clubbing.' "You know any place that would be discreet and girl might enjoy herself." Everybody is talking about a new place that just open that is on the interstate called The Rendezvous. They have good music and good looking guys. "Sounds like my kind of place", Sandy said. You want the job or are you busy. All you have to do is make sure the kids are asleep and then you all the time in world to check out Cindy's video collection. You might as well crash on the couch because I won't be back until real late. Just don't get anything on Cindy's couch or we'll both be dead. Sandy knew that as soon as the kids were asleep that Kellie would probably get her hunk of a boyfriend to come over. God I wish I was seventeen again she thought to herself.

Sandy left after telling Kellie to show up in about an hour. Jogging to the front door she opened it and went upstairs to her sister's clothes and search for the perfect dress. She found just the dress. It was electric blue and strapless. It slit up to the upper thigh. Sandy tried it one and it fit like a glove. It flattered her figure and accented every curve.

She slipped out of the dress and lay down on the bed. She took a deep breath and tightened the ties on her bustier until the cleavage achieved the maximum effect. She checks to make sure her stocking seams were straight. Walking over to her sister's closet, she looked for the accessories to finish up the outfit. In the jewelry box she found a pair of drop earrings and matching studs. She also selects a diamond drop necklace and a black suede chocker. Sandy fixed her hair and modified her makeup so that it suited her evening look. Sandy unzipped the dress and slides it over curvaceous body... This time, as she looked in the mirror she notices her breast as they barely hide the nipple. The dress made her bust look awesome and her enhanced figure looked gorgeous.

Maybe I might get lucky tonight she thought to her. It had been a while since Jack and she had made passionate love like they used to.

Sex lately had been quick and methodical. Jack had changed lately, to spice up their sex life Sandy had encourage Jack to try to fantasize and had even encouraged him to try sex wearing her lingerie.

This seemed to excite him more than normal sex. I wonder she thought. The ringing door bell brought back to the real world. Putting on her heels she head down to the door to let Kellie in. Kellie walked in the door and looked at Sandy and simply said, "Girl you look hot." Sandy checked her makeup and headed into the garage. Her sisters black Jaguar was parked in her slot. Taking the keys, she opened the car and slid into the driver's seat. She was a gorgeous girl driving a hot looking car heading out on the town. The car roared to life and she backed out it out of the garage and into the street. She headed to the restaurant to eat. Reaching the restaurant Sandy parked the car carefully; leaving the car she noticed a young blonde haired male watching. She decided to give him a show and slid out of the car allowing her dress to hike up her thigh exposing her scantily covered crotch and bare thigh above the stockings. Sandy smoothed her dress and walked into the restaurant to get something to eat.

  

  

  

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