A Boy With Girly Hair - Part 19 (Patreon)

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Sister's Bet

By the time I had returned home, Spiro’s actions were still on my mind. Jenna was in the living room and had asked to be filled in on the night. My initial intention was to avoid mentioning anything at all.

“Fine,” I said. “Just a normal, enjoyable night.” Though by now, Jenna could see right through me when I was telling a lie. She got up from the couch looking accusatory.

“No no no, I see you’ve got a little bitty smirk on your face. What happened?”

My parents were in the room over and I didn’t want them to suspect anything and the way Jenna was speaking to me would undoubtedly catch their ears.

Conceding, I led her to my room upstairs where I closed the door behind us. I then began to detail everything from the night before the girly hairstyle I was given at the dance, meeting Angelica, and staying the night at her house, dressed in girl's pajamas as to not arouse suspicion from her parents.

I then went in-depth about meeting Angelica’s date that night, Spiro, explaining that he was a football player from another school and a good friend of Angelica whom he had known from a church group. I also told her about how I had sat on his lap while he brushed my hair, but I strategically left out how I accidentally let out a small moan.

“Jeez, Sam, you had quite the night! I’m really impressed you never got caught by Angelica’s parents though I suppose you’ve had a lot of practice with disguise.”

“But that’s the thing don’t you think it’s weird that I never get caught? I mean, how many boys would be able to avoid getting called out dressing as a girl for this long?”

Jenna sat back up on the bed as I nervously paced the floor. “You’re clearly not like most boys, Sam. And I don’t think that’s a bad thing.”

I let that sit with me for a moment. It’s true that I often find myself in situations where I’m displaying some sort of femininity whether public or private and I typically pull it off with ease. Maybe I should consider myself lucky that I can so easily fake the appearance of being a girl. Otherwise, I could be opening myself to a lot more judgment or bullying…

Jenna must have noticed the strained look on my face, as she quickly changed the subject.

“Are you excited for Homecoming Week?” Trust me, this is easily one of the most fun weeks of the year.

I was very much looking forward to it. Since I’m only a freshman, Jenna typically served as my introduction to each school function, often helping me determine my opinions on things before I even experience them for better or for worse. But she seems to think positively of spirit week.

“I’m definitely pumped, though I think it’s weird they don’t announce the themes until the day before,” I concluded. “Wouldn’t it be better for them to give us a chance to plan our spirit week stuff in advance?”

“Oh but that’s part of the fun. You saw they announced Monday’s theme right?”

“No, what is it?

“Denim Monday. Wear as much denim as you’ve got! Layers on layers!”

“Denim Isn’t that kind of dumb? Everyone’s just gonna is looking like hicks,” I said.

“Oh no no no! Denim is super in style right now  just because you wear baggy jeans and think of hicks wearing denim overalls doesn’t mean it’s not cool.”

“I’m sorry, I just don’t see it.” I started to lead Jenna out of my room. “Listen, I’ve got to get changed to go for a run. The 5K run this weekend is what I really care about.”

About an hour later I returned from my six-mile run one of my faster times in recent memory! I was hoping to spend the rest of this day relaxing and resting my body so I’d be ready for my next workout and not too sore.

I stretched, drank water, and then hopped in the shower to cool down and rinse off. I had gotten so used to using Jenna’s shampoo that it just came naturally at this point.

The bottle was a bright pink with flowers on it. Damn, it’s a good thing I’m only sharing this bathroom with Jenna, where she doesn’t judge me for using her flowery smelling shampoo.

I then immediately thought of Spiro and how he had earlier complimented the smell of my hair. I wonder if when he used to have long hair, did he also use his sister’s shampoo? Maybe using a girly shampoo is just a long-hair thing, as opposed to a feminine boy thing.

But even if he did, I thought, there’s no way he’d be able to pull out a pink shampoo bottle as a football player. Especially while showering with all those guys in the football locker room. He probably puts up such a manly front.

KNOCK KNOCK KNOCK. Sounds like a Jenna knock.

“Sam! Come into my room when you’re done. Got to prove something to you.”

I quickly erased the strange thought of Spiro’s shampoo choices out of my head and finished up in the bathroom. I wrapped a towel around my waist and my hair to let it dry and walked into Jenna’s room.

“Okay, are you ready?” Jenna said, nowhere to be seen.

“Where are”

Suddenly she popped out of the closet in a brand new look. She was wearing a sleeve denim top with a few buttons down. She wore lighter blue denim shorts with frayed edges and had white sneakers on below. The main event, however, was her white denim jacket left open and the sleeves slightly rolled up.

“The jacket’s brand new and the rest I already owned. What do you think?”

“I mean I’m never one to say that my sister doesn’t look good… but that’s a lot of denim.”

“Oh come on, it’s cute! You just don’t know fashion. Have you decided what you’ll do?”

“I haven’t really thought it over yet,” I said, “But I can never go wrong with classic jeans and tee-shirt look.”

Jenna scoffed, “You’re so lame. If it weren’t for me you’d have like no taste wait for a second” She got that look in her eye like she has a big idea. She pulled out her phone and opened Instagram, “As of today, Sammi_Jaclyn32 has 35,000 followers. How about you take a picture wearing this outfit and if it gets, says, 10,000 likes by the end of the day, then I win. If not, you win.”

“Wait, then doesn’t that mean you don’t get to wear the outfit to school?” I pointed out.

“Honestly, I don’t care,” Jenna said with confidence. “As long as someone gets to appreciate my taste. A lot more people will see it on this app than they would at school.”

I was a firm believer that the all-denim look while interesting, would NOT make for a successful post. It was too out there. And I was willing to prove it to Jenna in a little friendly competition.

“Okay, what are the stakes?”

“How about if you win, you get my share of the money we got from Trista’s salon.”

WOW. She was willing to offer up that much money just on a silly bet?

Jenna continued, “but if I win I get to pick one of your looks for spirit week.”

“Hmmm, but we don’t know the themes yet. And you’re not gonna make me wear anything that would jeopardize the Sammi secret, right?”

“Of course not! I’m not a monster, Sam.”

After a brief moment of final consideration, we shook on it.

“Yes yes yes!” she exclaimed. “Go finish drying off and come back in here for the transformation!”

I scurried back into my room to put on some underwear and then blow-dried my hair in the bathroom. Returning to Jenna’s room, she had already laid out the outfit on the bed.

“Okay I appreciate you stripping down already, but those boxers will have to go.

“For what?”

“Uh, panties Duh! These shorts are pretty short, you’ll need something to help them fit better.”

Jenna tossed me a pair of light blue soft cotton panties and instructed me to put them on. She politely turned around while I stripped off my boxers and I slipped the panties up my legs. I positioned my ‘package’ around a bit to make things fit better.

“These are comfortable,” I added reluctantly, “but they fit different”

She turned back around. “Oh, that’s because they’re a cheeky fit. It’s designed to make your butt pop a little more. Well, damn!”

Jenna was staring wide-eyed at my butt. “Look in the mirror Sam!”

I turned around and saw my figure in the mirror. It was crazy how plump my butt looked! “Oh god.”

“All that running must be paying off. Your butt looks great! Any girl would kill for one like that.”

“Alright alright that’s enough,” I complained, cutting her off. “Let’s throw on the rest of the outfit and leave my butt alone.”

Jenna helped me dress the rest of the way. We began by pulling the jean shorts up my body and fastened the button. Once again, these did nothing to help make my body look any less girlish it was the kind of butt that guys get caught peering at for too long.

The denim shirt was next, but Jenna immediately thought it wasn’t sitting right. She found a matching bra in the closet and helped me put it on to complete the illusion of a figure. Now the shirt fits much better, and we were able to tease with a few buttons down. The look was completed with the white denim jacket and white tennis shoes.

I brushed my hair to give it a tad more volume before Jenna picked out a white scrunchie for my hair. We put it up in a high ponytail and voila!

“You’re so pretty!” Jenna flushed with pride.

“Yeah yeah yeah let’s just get on with the bet. I’m ready to win my money.”

Jenna instructed me to make several poses in her room while she took pictures. Hands-on my hips, hands-on knees leaning forward, and of course a few pictures laying back on the bed making sure to leave my face out of each one.

I waited as Jenna compiled the pictures on her phone and scanned through them.

“I think I like this one… no wait, this one!” Jenna exclaimed as she gleamed over seemingly every picture.

“JUST PICK ONE!”

“Alright, fine. We’ll do this one featuring your butt and turning sideways. It’s a really sexy pic.”

She typed up a quick caption, a few hashtags, and a filter, and bam. It was posted.

“Now we wait,” I said matter-of factly.

By the end of the day, I’d hopefully be a richer man.

But if I lose… one of my spirit week outfit choices is completely in the hands of the person who’s been dressing and photographing me as a girl for weeks.