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A Boy With Girly Hair - Part 5
🕑 Added 2020-08-08 05:55:06 +0000 UTCAdding a Wardrobe
I wouldn’t say I was “Insta-famous,” despite what Jenna said. Sure, 2,506 was a lot, but I totally think that Jenna is blowing this out of proportion. I mean, there are plenty of people who have over 2,500 followers that wouldn’t be considered famous.
Regardless, the joint effort between us (and by joint effort, I mean HER effort, and me just letting her use my hair) has garnered a lot of attention.
“You coming, Sam?” Jenna called from her room upstairs. I was headed to her room to help her out with her newest assignment for fashion class. All I know is that the assignment is “casual”. I guess we’ll see what that means.
I walked up the stairs and entered Jenna’s room. She was digging through her drawers and closet for clothes.
“Since the assignment is ‘casual’, I figured we wouldn’t need to try to hard and just pick out some basic everyday things,” she said. Her eyes lit up when she saw something in her closet. She picked up the garment and threw it towards me, “those are some skinny jeans. You have slender enough legs that they should fit you fine.”
I held them in my hands. I’d never worn jeans this tight.“Will these hurt my…you know.”
“Oh, no, you should be fine. They are a bit tight in the crotch area, but as long as you don’t wear boxers you should be fine.”
However, I did have boxers on. I took off my pants anyway and tried changing into the skinny jeans. I pulled them up to my waist, but they really didn’t fit as I’d hoped.
Jenna laughed at the sight of me. “You know, those jeans do look good on you from your ankles to just before your waist, but your boxers are all bunched up.”
“Yeah, these feel really awkward to wear, and not just because they’re girls’ jeans.”
“Here, I have an idea,” Jenna said, as she walked up to one of her drawers. She took something out of her top drawer and tossed it towards me, “Wear this, the jeans will fit better.”
I caught what she tossed to me. They were panties.
“You want me to wear…panties?” I asked nervously.
“Well if you want the jeans to fit, then I’d wear them.”
“Well of course YOU’D wear them. Aren’t they a bit feminine?”
“Sam, they’re just white cotton panties. And you don’t even have to think of them as panties. Just, underwear.”
For some reason that made it seem better. I mean they only looked a little bit different from white briefs. I excused myself from the room and changed in the bathroom. I figured there’s no reason to hesitate and think over my decision to put them on. I promised Jenna and myself that I would be more open, and I guess wearing these panties would be a start.
I put them on and they looked tight, but felt okay. I then put the skinny jeans on and they fit much, much better. The jeans hugged my legs and actually felt decently comfortable.
My sister then came in the bathroom to check, “Ooooh! They look really good! Let’s get the rest of your outfit on!”
I exited the bathroom and she escorted me back to her room. On her bed was a green crop tank and the black bra from before.
“Girls’ shirts always fit better if you have a bra on,” Jenna said assuringly, “I’ll stuff it too to help your figure,”
Jenna walked over to her drawers and pulled out what appeared to be pantyhose. She grabbed one pair, bundled it up, and placed it on the bed. She did the same with another one.
"First, let’s get that bra on you!”
I had put it on before, but she helped me out this time. What an odd feeling wearing a bra was! It’s a part of my body that never really has anything tight around it. It’s quite the experience with just the bra, but then Jenna placed the bundled up pantyhose into the cups of the bra. Now THAT felt weird. A very low percentage of guys ever get to feel what it’s like to have breasts.
Jenna then slipped the top over my head and the look was pretty much complete.
“Wow Sam! That outfit actually looks really good on you!” Jenna said, a bit surprised.
I took a look in the mirror. She was right. The jeans and top fit really well. I wouldn’t say that I have a completely girlish figure, but my butt is definitely a bit…more plump…as compared to other guys, and the skinny jeans really helped accentuate that feature. That was the same case for my hips as well. I never really noticed that they were just a bit wider than most guys until I put on these jeans. And of course the bra did what a bra does. I now had B-size breasts that obviously made me look girlier.
“I’m a little surprised at how well this stuff fits me too…”
“I just can’t get over those jeans! Your figure is honestly to die for! You have a cute little butt and just wide enough hips that I’m sure any guy—“
I cut Jenna off, “Please stop,” I said, red as a beet.
“Oh! Geez I’m sorry! I got carried away. It’s just that you look so good.”
“I understand. Just…just don’t flatter me THAT much.”
We both laughed, “So you need to take pictures or something you said?”
“Yeah if you’re okay with that, it’d be great." Jenna pulled out her phone, “Since the assignment is casual, you’d think that you just need to stand there, but girls ALWAYS want to look cute, even if we are dressed casually.”
“Uhh…okay,” I said, not sure of what exactly she wanted me to do, “what do you mean by ‘look cute’ though”?
“Well just do some cute poses…and that reminds me!”
Jenna ran into her closet briefly. She pulled out a pair of pink socks. “We’ll have a few shots of your feet, so you’ll need girls’ socks.” She then ran to her dresser and grabbed something else, “And of course you’ll need a headband too. I won’t need to do your hair today, but having since your hair will be in some of the shots, we need to show that you’re making at least an attempt to look cute with your hair."
I’d put on headbands before, but just not a pink one. It was a wide, plain elastic headband; it’s one that you’d find an average girl wearing, so I guess that this one made sense for the casual look.
Then it was time for the photoshoot. Jenna was smart not to make me think of girly or cute poses, as I would’ve been wrong and just embarrassed myself. Jenna told me to first lean up against the with my legs crossed—the “sassy look” as she referred to it. The next one was she had me do was also against a wall, but had me facing it with my hands on it, and one of my legs bent up. That one certainly felt like a "cute" pose. She took a few more with my hands in different positions and sitting in different ways. The final one that she took was me in a prone position on the bed with my legs bent at my knees and crossed. I then rested my head on both my hands. It felt like a very feminine position.
With all the pictures taken, I got up from the bed.
“Thanks for being my model today. Hopefully my class will like these pictures tomorrow!”
“Well if your reactions to how I looked were accurate, then they should definitely be a success,” I responded. I then began to take off the socks and fold them back up.
“You know, Sam, you can continue wearing the clothes the rest of the day if you want…”
“Uhhhh do you want me to keep wearing them?” I asked.
“It’s up to you, but since they seem to look good on you, and if you like looking good, then you might as well keep them on?”
I thought about it for a second. I mean, wearing these girls clothes aren’t the worst thing in the world. The jeans are super comfortable and so are the panti—i mean, underwear.
“Well I feel like it’s kind of weird walking around the house with breasts, so I think I’ll take the bra off…but I’ll keep the rest on.”
“Yay!” Jenna responded, “I mean you look good and feel good so, why not?”
Jenna then helped me take off the bra and took the bunched up pantyhose out of the cups. “Want to keep the crop top on?”
“That depends,” I said, “Does it look cute on me?”
“Well duh!” Jenna enthusiastically replied. We both had a laugh and I put the crop top back on.
The rest of the night I just did my normal routine: dinner with the family (which was surprising because my parents were totally accepting the way that I was dressed), homework, and then just watching Netflix.
———————————
Usually school is pretty inconsequential and boring, but today there was something very odd that happened. I was in my math class (which was my last class of the day) and we had a substitute teacher. However, this particular sub was the kind that literally didn’t care AT ALL about whether we did our work or not. So being high school freshmen, we talked amongst each other.
Me, personally, did not have any friends in that class, so I kind of just kept to myself. What I ended up doing was played on my phone until I heard my name called from right next to me.
I turned around and it was three really popular girls. Jessie (a blonde bombshell), Haley (a cute petite brunette), and Hannah (another blonde bombshell). I turned and they all waved to me. Why would they want to talk to me? I’ve never been approached by a really pretty girl, much less the three most popular in the grade. Could they be talking to me because they…like me?
“Hey Sam!” Hannah said, “I think you dropped your hair band.”
I guess I was wrong. She was holding a black hair band, “Oh, thanks.”
Hannah handed me the hair band, and I turned back to my seat.
“Oh and by the way, your hair looks really good,” Haley said.
I turned back around, a bit surprised at the comment, “Oh…thanks that’s really nice of you to say.”
Jessie then chimed in, “What shampoo and conditioner do you use? I really wish that my hair could be that soft and shiny.”
“Well it’s whatever my sister uses. She tells me it’s best for my hair and I guess she’s right. I’m pretty sure it’s like L’Oreal or something.”
“Well it is doing WONDERS for your hair.” Then, being very forward, Jessie leans in and smells and feels my hair, “Oooh! It IS soft! And it smells like strawberry!”
Then the other girls started to lean in to smell and fell my hair. They all said it was “delectable”.
Then the girls started touching my hair a bit more, fingering it, twirling it, and running it through their fingers. They seemed like weirdly engulfed in it. I looked around to see if anyone else was noticing how invested they were in my hair, but everyone was pretty much involved in their own conversations.
“Your hair is so lovely,” Hannah said, still staring at it. I briefly considered touching her hair, but figured that would be really awkward and weird to do. But it was also difficult to tell them to stop, as I didn’t want to be rude.
It felt like a while that they were touching my hair, even though it was probably only 20-30 seconds.
“Hey can I have that hair band for a sec?” Haley asked me. I was a little thrown off by that question, but I took it off my wrist and handed it to her.
Haley took the hair band and started to pull my hair into a pony tail. I thought that it was a relatively normal thing to do, as I’ve worn a ponytail many times, but she pulled it into an especially high ponytail. She and the other girls then fingered it around and spread the ponytail a bit to make it look fuller.
“You like this look?” Haley asked.
“Uhh…I mean I’ve never had a high ponytail before…”
“You don’t like it? But it fits you so well!” Hannah added, “I mean seriously this hair is too perfect, soft, and shiny to not play with.”
“Yeah you know there’s this girl on Instagram Sammi_Jaclyn32 who is totally the new thing at this school,” Jessie said, “your hair is almost up there with hers."
“All the girls are WAY jealous of her hair, and her body is just to die for!” Hannah added. She turned to the other girls, “Did you see the picture uploaded yesterday of her in those jeans and crop top?”
“Ah! She literally has the perfect body! I think I’m really gonna start working out more to get a butt like that,” Haley said with conviction. Wow, I guess I wasn’t aware of the impact these pictures were having, or of the fact that the account has reached popularity among the freshman class too. I mean, is my body and hair really that good? What if this secret were to come out? Is my body really that...girly?
