This choice: Jack does a decent job impersonating his normally vivacious Mother • Go Back...Chapter #5Jack does well filling in for his mom by: Kirafair   Jack Hughes’ personality naturally lended itself to following his Mother’s lead. Even in this setting where he was temporarily a dead-ringer for Chelsea Hughes. He put up only a feeble protest which she decisively swept aside.
“We have relatives and friends who have made plans to spend Christmas Day with us. I think you’ll agree we can’t let them down by canceling at the last minute. But I also want you to think of this as a wonderful opportunity”
He flinched at the word ‘wonderful’. “In what way is this an opportunity?” he whined
It was unbelievably weird to see his usual face looking so supportive knowing it was his Mother’s mind behind those eyes. She reached across the table and firmly grasped his now dainty hand in a subtle gesture of support
“You have a great future ahead of you. I’m so proud of you and what you’ve already accomplished. But keep in mind with an advanced degree, your colleagues at whatever company you land with will be looking to you for leadership”
She paused in preparation for the next part of her pitch. Drawing on her years of accumulated sales skills, she leaned closer and said in a soothing voice
“You’ve always been a follower. You are a good athlete and a great teammate when you played any sport in High School. But you never demanded the ball or seized the initiative when the team needed you. Today, I need you to do that. Be the leader of this house. Be the woman who is the vivacious host for today’s festivities. For one day, be Chelsea Hughes. I think it will help you in the long run”
By this point of her pitch, her energy level had become infectious. Jack was captivated.
“I believe you can do it. This is your moment to shine. What do you say?”
*****
On the other side of the dining table, Bethany Hughes watched this unfold completely mesmerized. She was convinced her Mom could sell ice to the Eskimos. Yet her mind began to wander off. What was it like for these two? To wake up one morning as the opposite gender?
Bethany began to ponder the feeling of a dick between her legs
*****
Jack had been swayed by his Mother’s appeal. She had managed to both challenge him to rise to the occasion while assuring him he could do it. The first step was getting dressed for the day.
Chelsea dismissed his shyness when he balked at undressing in front of her. “You think I haven’t seen that body before? Besides, you need to take a good look at it and take pride in yourself. It’s the result of a lot of hard work and exercise” she commanded
With a stream of encouragement, Jack gradually became accustomed to seeing her naked body. He agreed she should be proud. Still in her early 40’s, Chelsea Hughes was quite attractive. Slowly but surely, he began to feel that same pride.
With her guidance, getting dressed was relatively easy. Underwear, pantyhose, and a Red knee-length dress. She had him practice walking around in some low-heeled shoes while she got dressed for the morning’s religious service. He felt with each step he was growing more comfortable. Chelsea echoed those sentiments when she reappeared minutes later dressed in a Blue Sweater and Khaki pants.
“You’re moving around great already. One tip, women naturally move their hands around to emphasize both their body and verbal language. Keep that in mind.”
Jack found himself beaming from her praise “Thanks, umm honey? But I’m not done right? Do you wear makeup to church?”
She chuckled “It would be scandalous if I did MOM. But you are correct, a modicum of makeup is appropriate for you today. I got some new tech recently which I think you’ll get a kick out of. The device is called AutoFace. Not sure I would have gone with that brand name but whatever” she mused
This left Jack bewildered by what she was talking about. She ushered him over to the vanity table and bade him sit. A small Silver box he had never seen before sat directly in front of him.
“Repeat these words. AutoFace, initiate program. Run Day wear, formal setting”
Jack did as instructed. He jerked backwards when the box began to unfold into an impossibly larger construct. From behind, Chelsea from placed a hand on both shoulders and gently held him in place
“Don't worry. This tech will place a mask over your face and impeccably apply the makeup in less than 5 minutes.
Jack managed to suppress any anxiety as the device engulfed his face. A feminine sounding mechanical voice emanated from the box
“Good morning Chelsea. Program initiated. Please sit perfectly still”
As the timer counted down, Chelsea maintained a comforting dialog to fill the void.
“I’ve been using it for months now and I’m very satisfied. The box never fails to do a perfect job and it saves so much time each day. Supposedly, the manufacturer is coming out with a new tech line called AutoCloset. It takes care of dressing leaving you free to respond to emails or talk on the phone. I may have to look into having that module installed one day”
A soft chime indicated the process was complete and the box folded back onto itself. Jack marveled at his beautiful face. His eyes sparkled, the complexion was flawless and his lips were a vibrant Crimson Red. A little work on his shoulder length hair and the addition of jewelry finished the process.
Jack thought about objecting when she helped him clasp a Gold chain around his neck that looped through her plain Wedding band. A remembrance of his Father who had lovingly placed it on her finger many years ago. But this was her signature look. It served to remind him that for today, he was Chelsea Hughes. He needed to look and act the part.
*****
The rest of the day was a whirlwind. For Chelsea, it was pretty easy. She simply had to act like Jack and just hang out in the background. Occasionally, she found her own bubbly personality leaking into her impersonation as she interacted with some friends or relatives on her husband’s side of the family. But nobody appeared to notice her deception. They probably chalked it up to ‘Jack Hughes’ developing into a fine young man.
For Jack’s part, with each passing minute he grew more comfortable. He noticed that all he had to do was emulate his Mom’s bubbly personality and people responded positively. When it came time to make a toast once everyone was seated, Jack truly felt excitement welling up from within that he was about to take on the role of the head of the Hughes household
“I want to thank everyone for being here. It warms my heart to share this meal with all of you. Join me as I wish everyone a healthy and happy holidays as well as into the coming year”
As glasses clinked all around the table, Jack winked at his sister and Mother. Despite how terrifying this day had started out, they had persevered and everything turned out well. He felt an immense sense of accomplishment.
*****
The dinner party was winding down when the front door alerted them they had a visitor. It was Erika, Jack’s girlfriend who had stopped by to extend her well wishes and join them for a late dessert. With some difficulty, Jack managed to maintain a friendly smile when she greeted him with a hug
“Hello Mrs. Hughes. You look so pretty tonight”
As a testament to how well he was fitting into the role as hostess, he completely lost track of his Mom and Erika when they later slipped away from the party to head downstairs to the game/exercise room.
*****
Chelsea was unsure how to respond when Erika grabbed her hand and led the two downstairs. After a moment's indecision, she decided following Erika’s lead was very much in character for her son. She assumed Erika wanted to have a private conversation. Chelsea neglected to consider that both she and Erika were hormone-fueled young adults. As soon as the door closed, the young woman was all over Chelsea planting passionate kisses while simultaneously trying to pull the sweater over Chelsea’s head.
She struggled with how to respond. This was her son’s girlfriend after all. But many factors came into play. Chelsea was so laser-focused on her children and jobs, she hadn't known the touch of another human over a decade. In addition, her new male body was now pumping out sex hormones. In the end, she gave in to her growing desires.
Erika dispelled the concerns of her boyfriend. “This is unbelievably hot that we’re about out to have sex with your family upstairs.”
Chelsea didn’t trust herself to talk. She hummed contentedly while her lips and hands roamed over Erika’s body. To use a metaphor, this was a playground she had some familiarity with. She did worry she had done something wrong when Erika pushed away but in the end her fears were baseless.
Erika reached into her purse and removed a foil-wrapped square object. Condoms had not significantly changed in over a century as Chelsea sucked in a deep breath. Erika furiously ripped the packaging apart and to Chelsea’s astonishment, she placed the rolled-up condom between lips and teeth. After tucking her long blonde hair behind both ears, she began bobbing up and down on Chelseas’s erect cock. With each cycle, Erika managed to unroll the condom a bit more. Every time she went down, Chelsea’s cock went deeper and deeper into the young woman’s mouth. This was incredibly arousing.
A part of Chelsea’s mind was screaming it was wrong. But it was a tiny voice easily drowned out by her male body’s base instincts. Without a word, Chelsea maneuvered Erika’s body onto a Yoga mat and began to rhythmically thrust her cock into the welcoming pussy. Despite this being her first-time orgasming as a man, Chelsea delayed the eventual climax for a long time.
As the two savored the sexual bliss, Erika gently touched Chelsea’s face. “Oh Jack baby. That was so good. So good” she repeated over and over.
Chelsea felt a wave of shame overwhelming the feelings of ecstasy. Not only for what she had just done.
But for how much she enjoyed it.
What happens next?  indicates the next chapter needs to be written. |
| Members who added to this interactive story also contributed to these: |
<<-- Previous · Outline  · Recent Additions © Copyright 2025 Kirafair (UN: kirafair at Writing.Com). All rights reserved.
Jenny Amara has granted Writing.Com, its affiliates and syndicates non-exclusive rights to display this work within this interactive story. Poster accepts all responsibility, legal and otherwise, for the content uploaded, submitted to and posted on Writing.Com. |
View Portfolio
Visit Notebook
Send Gift Points
Awards
Badges
Send Email
Community Newsfeed
General Discussion
Sponsored Items
Book of Trinkets
Static Items
Books
Groups
Interactive Stories
Audio
Campfire Creatives
Community Notes
Crossword Puzzles
Documents
Folders
Images
In & Outs
Madlibs
Photo Albums
Polls
Product Reviews
Quizzes
Survey Forms
Web Pages
Word Searches
More by this author