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Rated: 13+ · Interactive · Comedy · #2232773

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Chapter #11

Julia stops by the next day

    by: Kirafair Author IconMail Icon
Chris did not immediately act on his urge to try on his Mom’s dresses or suits. Partly for fear of getting caught or just a feeling that a boy shouldn’t be doing this. He removed his Mom’s scrubs, returned the wig, and cleaned off his makeup.

Throughout the rest of the day, no matter how hard he tried, he couldn’t stop thinking about his experience and how the Cable Repair guy believed he was Cynthia Jackson. He almost welcomed the distraction when Julia stopped by in the afternoon. Chris tried to make small talk without referencing the challenge. Julia was more direct with what she wanted.

“Would you like to come over to my house tonight?”

“Sure, are your parents going out?” Chris asked hopefully. Some alone time could be a chance to repair the growing rift between the two.

“No” she replied nonchalantly “I wanted to watch the Pittsburgh - Philadelphia football game that is on tonight with you. Maybe you can point some things out to me.”

While schools all across the country were preparing for their upcoming football seasons, so to were the Professionals in the National Football League. During the run-up to the season openers, each team had several exhibition games scheduled and a few were broadcast on network stations.

“Julia, this game doesn’t even matter. None of the good players will be in the game for long. The teams don’t want to risk them getting hurt in games that don’t count.” Seeing an opportunity to reinforce his concern he pleaded with her “When are you going to give this football thing up? When you tear a knee ligament or break a bone?”

Julia bristled at his tone “So it’s okay that you could get injured playing football but you also get to decide what I can do with my body?” Chris could only stare at her as he could find no words to counter her argument.

“Never mind” she spat out angrily and stormed off.

Thus on this Saturday night, fans across the country were tuning into watch a totally irrelevant game in which many of the players wouldn’t even be on the final roster. The NFL did gain at least three new viewers. Julia, Jessica, and Tammy were all watching from their homes, excitedly texting each other about what they saw and what the commentators said.

Chris also tuned into the game for a bit before getting bored and turning it off. He turned his attention to his laptop and soon found himself going down a rabbit hole as he searched for information about boys dressing like girls. He found plenty of material including many TikTok and YouTube videos, Instagram pages and even two streamers on Twitch (F1NN5TER and RYNALI) who live streamed their transformations into girls. He was simply amazed with all the content at how pretty the boys could become.

Julia fell asleep that night imagining what it would be like to be on the field as fans cheered her for a big play and not just ogling her in the cheerleader uniform. Nearby, Chris’ thoughts dwelled on whether he should try dressing like his Mother again and could he do it better the second time.

*****
Sunday morning found Chris alone in the house. His Mom was out doing her Realty job again. He had resolved not to wear her clothes but as he was shaving his legs he had a thought:

‘What do pantyhose feel like on smooth legs?’

He soon found the sensation was exhilarating. Of course he had to try on some of her shoes and perhaps too ambitiously selected some Black 3 inch pumps. They were tight in the toes but his biggest issue was just keeping his balance as he walked.

The pain seemed to fade once he saw how his legs and feet looked in a mirror. He was captivated with the image. He had to add more. Putting on a bra with socks filling the cups began his torso transformation. His next action was the biggest decision. He went with what he thought was a rather plain dress but what his Mother would have called a LBD. A Little Black Dress. It was knee length, had 3/4 length sleeves, and a round collar. It also zipped up the back. Chris kicked off the heels and with building excitement stepped into the dress. He then discovered a problem. This dress was designed to snugly fit a women’s body and the zipper began to resist movement around his waist. He was ready to give up when he recalled an item in his Mom’s dresser. It was black and seemed to be made of an elastic cloth. Chris guessed that his Mom used this shapewear when she wanted to make her feminine curves a little more pronounced. With effort he was able to pull the garment over his hips and very tightly around his waist. It had the desired effect as his waistline was noticeably thinner. This time he was able to zip the dress all the way to the top. Chris twisted back and forth in front of a mirror loving the look. Like the previous day, he was driven to improve the overall image.

Thirty minutes later he had the wig on his head, modest makeup applied and even some jewelry on his right wrist. He was even more thrilled by how he looked than yesterday.

https://m.media-amazon.com/images/I/71uO...

Chris modeled several poses as he took some selfies. Having evidence that he was dressed like this on his phone was almost intoxicating.

Deciding that he had enough fun, he went to remove the dress. A surge of panic swept over him when he tried to lower the zipper and it only went down an inch and stopped. He was able to raise it back up but he got the same result when he tried to lower it again. With each attempt he tried harder to force the zipper past whatever was blocking it to no avail. His heart raced as he imagined how furious his Mom would be if she found him stuck like this and prayed for a miracle. It must have worked since the zipper cleared the blockage and he was able to remove the dress.

After putting everything back and cleaning up, Chris decided he needed to get out of the house and away from the distraction of his Mother’s clothes. This could have ended in a disaster. He jumped on his bike and went for a ride with no particular destination in mind.

*****
At that moment, Julia and Maria were sitting on the grass of the front yard at Julia’s house.

“You’ve done a great job Maria. Chris is my boyfriend and I doubt I could have gotten him to wear makeup and styled his hair like you have been able to do” Julia praised her friend. She didn’t notice that Maria’s body flinched slightly at the mention of the word ‘boyfriend’

“I’m surprised the boys have been this cooperative so far. I’m not sure what else we can get them to agree to though” Maria said softly.

Julia was deep in thought for a moment “Do you think you could get them to wear pantyhose? Stuff their sports bras?”

Maria shrugged her shoulders “Maybe. I’ll see what Chris is willing to do. Jake and Simon will follow his lead.”

Julia smiled “Go for it. I’ll check to see if anyone on the team has some clip in ponytail hair extensions they’d be willing to lend. I’d love to see Chris with hair down to his shoulders. Also, ask Coach Bosley if she could run a full dress rehearsal for the squad this week. I’ll get Tammy and Jessica to leave their uniforms with the Coach. This way the boys will get a hint of what being a Cheerleader is really like.”

These plans seemed to excite Maria as she too developed a broad smile.

*****
Chris was riding along when he saw a fellow 10th grade classmate, George Angelos, shooting a basketball at a hoop in his family’s driveway. Chris pulled up and said “Hey Gio” referring to his nickname. In elementary school, Chris and George had been close friends but the last few years they had begun to drift apart. The fact that Chris played some sports and had a girlfriend whereas Gio did not meant their social circles had little overlap. Chris greeted the thin, black haired boy “What are you up to?”

George seemed happy that Chris stopped by. “I’m thinking of trying out for the Basketball team later this year. Working on my skills until then”. He bounced the ball to Chris as an invitation to join him. They spent the next hour or so talking and practicing.

“Why didn’t you try out for football?” Chris asked. ‘That could have been a great way to get him more involved with school and our classmates’ he thought

Gio rolled his eyes “Parents wouldn’t allow it. Afraid I’d get hurt.”

Chris nodded his head in understanding ‘Only the girls seem to think playing football is no big deal.

Chris was grateful that George was polite enough to not mention Julia’s challenge. He did notice that his friend must have had a recent growth spurt. Gio was now several inches taller than him but his gangly body meant that he still weighed less by a lot. Chris hoped that his friend would be successful with basketball. Gio was both physically and socially awkward and making that team might help his self esteem.

*****
The two Coaches, Rebekah Bosley and John Forsythe had just finished eating at a local restaurant and were enjoying a post dinner coffee.

“What are your plans for the boys this week?” John asked his partner.

“Unless they quit, the usual cheer drills. I will also keep working on some tumbling practice. I have to admit they are picking that up surprisingly fast. How about for the girls?

John sipped his coffee with a thoughtful expression “This week will be a big test. I have Full Contact Scrimmages scheduled. Tammy will be fine since she is just kicking but Jessica and Julia will find out the drills last week were just a taste of what is to come.”

John had a strong suspicion that they only way Julia would quit was if she was taken off the field on a stretcher.

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