A Femboys Life Ch. 01

Hi guys, this is another series I'll be working on. I am not a femboy, nor do I know any, so if this seems a bit off compared to what you or someone you know has experienced, that's why. This story is fictional. Any resemblances to real people, places, or events are coincidental. All characters in this story are eighteen or older. I hope y'all enjoy.

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BEEP BEEP BEEP BEEP!

"Uuuuggghhh," I groan as I shut off my alarm. Thank god it's Friday, sure the high school years may be the best years of your life, but that doesn't make school any less tedious or boring. I get up and head to the bathroom to piss and take a shower. I enjoy the warm water on my body and the feeling of cleaning off a day's worth of filth. I get out after I've dried off and check myself out in the mirror.

I'm a pretty feminine looking guy, in fact I've been mistaken for a girl many times. People have told me my face looks pretty feminine with my high cheekbones and narrow jaw. I've also got a small straight nose, under which sits some pretty full lips for a guys, and a round chin… I've also got dirty blonde hair that goes to the top of my shoulders, although I usually keep it in a man bun. My eyes are a bright green and upturned. Even my voice is a bit feminine, though most people can still tell I'm a guy when I speak.

I'm about five foot five and I don't have much weight on me. A fast metabolism and good diet helps with that. I've got slender arms and legs, as well as small, feminine hands and feet. I've got a flat chest and stomach. My waist is slim and my hips flare out to meet a small round butt, giving me a slight hourglass figure. Due to my size I'd say I'm petite. I used to hate how I look but I've grown to love myself.

I dry my hair, then head into my room and throw on some clothes. I pick a blue Led Zeppelin shirt, some blue jeans, and a pair of blue Converse high tops. I grab my wallet, phone, keys, and backpack and head downstairs. Mom is at the table watching something on her phone. She sees me and greets me, "Morning sweetie, how are you?"

"I'm good, how about you?" I ask. I give her a kiss on the head as I go to the kitchen to make breakfast.

"I'm doing fine. I have to work late tonight so I'm gonna grab dinner on the way home," she informs me.

"Okay, well hopefully it goes well," I reply in between bites of cereal.

She comes over and hugs me, "Thank you, I gotta go, love you," she gives me a kiss on the cheek and starts getting ready to leave.

"Love you too, have a good day," I tell her.

"You too," she shouts as she shuts the door behind her. I finish my cereal, clean it, and then head out the door myself. I get in my 05 Passat wagon and make my way to school. I know, I don't really need a wagon, but I got it for a good price. The drive takes about five minutes, which gives me time to listen to Fireball. I arrive, park in a decent spot, then head through the gate.

At lunch I go to an area outside by the cafeteria where there are some tables and see my best friend Ben. I sit next to him and say sarcastically, "Hey loser, how are you?"

He looks at me with a dumb grin, "Pretty good, what's up with you fag?"

I ask him politely, "Can you please not call me that?" I came out to him last week, and though he's taken it well, sometimes he makes inappropriate jokes or remarks. I think it's mainly cause I'm the first LGBT friends he's ever had.

He grimaces, "Sorry, won't happen again, and yes I do have plans."

"It's okay, just thought I'd ask," I assure him. We spend the rest of lunch chatting about Tales of Malanor a new fantasy rpg we've been playing. He's a bit further along than I am due to me spending a lot of time on side quests. What can I say? When I like a game, I get invested. We split up after the bell rings.

After school I get in my car and head home. Once I get inside I go to my room and look at my dresser with a smile. I take off my pants and boxers, open the top left drawer, and put on a pair of light blue panties, which bulge at the front due to my four incher. I know it's not even average but I'm a bottom anyway. I put on my light blue Thor Ragnarok pajama bottoms as well. I head over to the closet, swap my shirt out for a white women's Tales of Malnor shirt, and put the clothes I just took off in my laundry basket. Yeah, I'm a femboy.

I've always been pretty feminine but I started identifying as a femboy when I was fourteen. My sister Aleighna thought it would be fun to dress me up in some of her clothes since we were about the same size, with me having a smaller chest due to being a guy. I loved the way I looked and I had her put make up on me too. I asked if I could stay dressed like that for a bit she said I could keep the clothes if I wanted. My parents were a bit shocked when they got home and saw me but they accepted my new identity pretty quickly. The next weekend I went to the mall with mom and Aleighna and got myself makeup, girl clothes, and some bra and panty sets.

I plop down in my chair and start up my PlayStation 5, I was lucky enough to get one when they came out. I start up ToM and immerse myself in the world. At around five mom calls, "What do you want?"

"I kinda want Popeye's," I tell her.

"Okay, you want your usual?" he asks. My usual is a three piece tender box with Cajun rice and beans.

"Yup, see you when you get home, love you," I answer.

"Love you too, be home soon," she replies and hangs up. Not even a minute later my dad gets home. I go say hi and we chat about our day until mom gets home twenty minutes later. We eat, watch an episode of Firefly, then I head to my room. I play ToM for a couple hours before hopping on my laptop to watch YouTube. After that I take off my clothes and hit the hay in just my panties.

Monday rolls around and it's back to school. I realize getting dressed that I fucked up. I don't have any clean boxers to wear so I either have to wear panties or go commando. I pick the latter as at least then the worst people could say is that I forgot my underwear. I'm getting weird looks from people and even some snickers during the first couple classes. I'm wondering know they could possibly know about my lack of underwear but that's not the issue.

In third period I get paired up with a girl named Zoey for a history assignment. She looks like Megan fox in the first Transformers, but a couple inches taller, and prettier. She looks at my hand and quietly asks, "Is that nail polish?" with a confused look.

I look at my hand and see a bit of red from the weekend on my right middle finger, "I accidently spilled some of my moms cause she left it out on the table. I thought I got it all of."

"Okay, come see me at lunch, I'll help you clean it off," she offers politely.

"Thanks, where do you usually hang out?" I ask. We've never talked before so I don't know.

"I'll be by the theater, I'm Zoey by the way," she offers a hand.

We shake hands and I reply, "Aiden, let's get back to work." We finish about seven minutes before class ends and wave goodbye as we head to our next class. We meet up at lunch and she helps me get rid of it. I thank her profusely before going to meet Ben.

I manage to go the whole day without anyone finding out about my lack of underwear. As soon as I get home I change into a pink tank top, pink panties, and pink pajama bottoms. Today's a pink day for me. I throw my laundry in the washer, get my homework done, then hop on ToM. I'm in a party with Ben and he asks, "Is it true you had nail polish on one of your fingers today?"

I hang my head in shame, "Yeah, my mom left it out on the table and I accidentally spilled it. I thought I got it all off but apparently I didn't."

"You sure it wasn't yours?" he teases.

"No it's not, trust me," I says having a slight panic attack on the inside.

"Sure it isn't, I bet you keep it hidden," he says in a joking manner. I know he's not trying to be mean, so I don't get offended by it.

"I'm sure, I just got to Fairhaven, where should I head?" I ask as I go through the town gates.

"Head to the blacksmith, he's got some good gear," he informs me. I spend another hour playing before I head to eat.

I play some more ToM after dinner. I'm not gonna lie, Gordon, the blacksmith, is pretty hot. He's a six foot four grizzled looking half orc with green skin and short black hair. He's also got this mean scar on his chin, and his little tusks, yum. I can't help but imagine his big dick stuffing my ass. I turn off my game at around ten so I can watch some YouTube before I sleep. At around a quarter to eleven I start fantasizing about the blacksmith again and decide to masturbate.

I take off my shirt and pants, leaving me in just my panties, and lay down on my bed. I close my eyes and imagine I'm in his shop looking at something when he comes over and asks if I need help with anything. We flirt a bit and soon I'm lying on my back in his bed. I move my hand up my stomach to my nipples, mimicking what he's doing in my head. I tweak them slightly and let out some moans. My nips have always been sensitive.

As I'm toying with my nipple I take my other hand and start lightly stroking my cock. I imagine him doing the same, saying how cute he thinks it is. I get myself to the edge and stop, some pre comes out, but I manage to avoid cumming. In my head he takes this opportunity to give me some tender kisses. His tongue leads mine in a dance as he caresses my thigh. As much as I love some good foreplay, I'm ready for him. I let him know and he positions himself at my entrance, his eight inch girthy cock throbbing in anticipation.

I start stroking in rhythm as he thrusts his way into my asshole, not even caring if it hurts. It doesn't since this is all in my head. I start stroking faster as his pace quickens. I have to stop every now and again to keep it from ending. During the pauses I give other parts of my body like my chest and ass some attention. I keep this going until eventually it's too much and I cum all over my stomach. "Oh fuck, oh fuck," I moan as waves of euphoria rolling over me with each surge of cum. I bask in the afterglow for a bit, then I clean myself up and go to sleep. I imagine him snuggled next to me as I drift off.

Wednesday arrives and my car won't start, so I get a ride from mom. The first two periods go smoothly, although I do get some people asking where my nail polish went. It gets a bit annoying after the fifth time. During history Zoey invites me to hang out with her and her friends at lunch. I accept cause I would like to make some new friends.

I head to where she and her friends are and see that she saved a spot next to her. I sit down and she introduces her friends Rebecca and Chelsea. Rebecca is a black girl with long black hair that falls to her shoulder blades. She looks to be the tallest of the group with an athletic build. Chelsea is the same height as Zoey and very curvy. Her ginger hair is the same length as mine but it's more curly. I really enjoy hanging out with them, though I'm not sure if they'd accept the real me.

Ben calls me after school and I answer, "Hi Ben, sorry about lunch. One of the girls in my history class invited me to hang out with her and her friends at lunch."

"Ah okay, did you have fun?" he asks. I'm glad he's not upset about me hanging out with other people. I thought he might be since we really only have each other.

"Yeah I did, we mainly just talked about music," I tell him.

"You tell them you like Justin Beiber?" he jokes.

"Boy I will come over there and slap you so hard you become a woman," I retort.

"Haha, well if you wanna hang out with them more, that's fine. You're allowed to have more than one friend," he tells me.

"Thanks Ben, it's good to know I have a friend like you," a pang of guilt goes through me as I say this. I decide then and there that he deserves to know the truth about me. I decide to tell him Saturday morning.

Friday Ben invites me to hang out at his place after school. I accept and let mom know. We get in my Passat and head to his place once we're let out. We get to his apartment and head inside. It's a decent place considering his dad works at Home Depot. We go to his room and play some MK11 on his PS5. We have fun kicking each others butts and cracking jokes.

We're watching a video of Chris Hemsworth interrupting a weather report when he asks, "Would you bone him?"

I chuckle, "No, I'd let him bone me."

He laughs, "Oh so you're a bottom huh? Guess I shouldn't be surprised."

"I thought I told you before," I state in surprise.

"Nope, but hey, I won't judge," he tells me with a smile. We play for another hour before I head home.

I wake up the next morning to the scent of bacon and eggs. I throw on some red pajama bottoms and a black women's t shirt. I head downstairs and see dad making some. I go over and give him a kiss on the cheek, "Morning dad, what's the occasion?"

"Martin gave them to me, apparently his dad's chickens over produced a bit," He answers. My dad works at an auto parts store and Martin is one of his coworkers. His dad owns a farm if you couldn't tell.

Mom walks in, "Do I smell eggs and bacon? Cause I'd love some."

"Yes ma'am, they'll be done soon so get ready," Dad responds. We get everything set up and enjoy a delicious home cooked breakfast. After getting everything cleaned up mom and dad let me know they're going to the mall later and invite me to join them. I accept the invitation and take a shower.

After I'm done I decide to go in my girl clothes, but for now I just put on a white tank top and red bikini panties. I also paint my nails purple and let them dry while I watch some YouTube. I'm watching a funny dog moments compilation when I hear Ben say from the door, "What the fuck!?"

I stand up and face him, "Hi Ben, do you mind taking a seat?" I gesture to my desk chair.

He sits down and with confused and slightly worried expression asks, "What's uh, what's with the all this?"

I take a deep breath as the moment I've been dreading comes, "Ben, I've been hiding a side of myself from you since we met, as you can tell. Do you know what a femboy is?"

He nods and replies, "I'm guessing you are one?"

"Yeah, I have been since I was fourteen. I hid it because I didn't know bow you would react but I'm telling you now because you deserve to know," I answer.

He thinks for a minute, which gets me worrying, then asks, "Do the girls from lunch know?"

"No you're the only person outside of my family and the school counselor who knows," I respond.

He puts the pointer and middle fingers up to his lips, then states, "This is a lot to take In, I'm gonna need some time to let it all sink in."

"Take all the time you need, I know this is a big deal," I assure him. We exchange goodbyes and he heads out. I hope he accepts me but I'm not sure if me having hid it for this long will help my case.

Mom comes into my room a minute later with a worried expression. She sees me and puts two and two together, "You okay sweetie?"

"Yes and no, I feel like a huge weight just got lifted off my shoulders, but I'm also scared of what might happen," I tell her. I'm not afraid to be honest around her.

She comes over and hugs me, "Don't worry too much, whatever happens, you're dad and I will be right behind you."

I return the hug, "Thanks mom, we still going to the mall?"

She smiles at me, "Yeah, we're leaving in thirty minutes, so you might wanna start getting ready."

"Okay, let me go do my hair," I say as I rush to my bathroom. Normally I wouldn't be going out as my true self but I feel okay doing it now since mom and dad will be there.

I come out of my room with my hair in a wavy bob style, with some purple shadow and lipstick to match my nails. I'm wearing a black Katy Perry t shirt that hangs off my left shoulder, showing one of the straps on my black Calvin Klein bra. I throw on the matching panties, tucking my penis between my thighs, and some navy blue skinny jeans. I finish the look with black Vans Authentics. I've got my brown purse as well. I go out to the living room where mom and dad are waiting, "Okay, I'm ready to go."

"Alright, let's get going then," my dad says. We get in the Taurus and head to the mall. On the way we listen to some classic rock, my second favorite genre behind pop.

We get there and I step out, ready to be myself, if only in front of strangers. Yeah I'm not confident enough to dress like this around people I know, but complete strangers who I'll most likely never see again, no problem. We realize how hungry we are and head straight for the food court. We've got plenty of time to look around. I get a bowl from Panda Express with chao mein and Beijing Beef. Mom and dad get some pizza. After we're done we head out to window shop and maybe buy something.

We spend most of our time just looking at what the stores have. I do wind up getting this cute baby yoda beanie from Spencer's. It's a caricature of him sipping out his mug. Mom and I are in Old Navy when I hear a familiar voice, "Aiden, is that you?"

I freeze up, recognizing it as Zoey's. I turn to her, "Heeeeyyy Zooeeyy, how are you?" my self-consciousness starts to take over as I avoid eye contact with her.

She crosses her arms as she takes me in, "You didn't spill your moms nail polish, did you?" she asks. I can't read her face so I don't know what she's thinking.

"No, it was my nail polish, and I just missed a spot cleaning it. Zoey, I know what you're thinking-" I start to say.

"That you look amazing?" she asks as if nothing was out of the ordinary.

I just stand there bewildered, "Wait, you don't think this is weird? Like, at all?"

"Oh of course it's weird, you're a guy dressed like a girl, but I'm not disgusted by it. If this is who you are, then who am I to judge? Plus you look really cute," she states.

My heart fills with joy as I give her a hug, "Thank you, it means a lot to hear you say that, especially now."

"Did something happen after lunch the other day?" she asks with concern.

I assure her, "No no, this morning I just told my best friend about this, and he said he needed space."

"Okay, well I hope things work out with him. If they don't, you can always hang out with me and the girls," she informs me.

I hear my mom calling for me so I shout, "Over here mom."

She finds me and sees Zoey, "Who's this?"

"Mom this is Zoey. Zoey, this is my mom," I introduce them.

They shake hands and mom tells her, "It's nice to meet you Zoey. Aiden told us how you helped him with his issue the other day," she lowers her voice on the second sentence.

"Oh, it was no biggie. I should get going, oh but first, want my number Aiden?" Zoey asks. We trade numbers and she hugs me one last time heads to the back of the store. I thought that was gonna a lot worse.

Mom and I go find dad and we head home. The entire ride I'm on a high. I thought today was gonna be one the worst days ever after Ben but now I feel like this is the best day ever! I skip to my room when we get home and turn on my PlayStation after taking off my pants, cause I don't care about not wearing them right now. I just wanna relax in the land of Malanor.

Monday at lunch I make my way to where Ben and I usually eat and he's not there. I shoot him a text asking where he is and he says that he's busy. I get the message and go hang out with Zoey and the girls. When I sit down Rebecca asks me, "Hey Aiden, were you at the mall on Saturday? I'm pretty sure I saw you and Zoey talking at Old Navy."

I look over at Zoey, who looks just as shocked as I am. I sigh and answer, "No point denying it I guess. Yeah, that was me in the makeup and girl clothes."

Chelsea chimes in, "I thought that was you. You looked so good, I was honestly jealous."

I give her a confused look, "Really? I thought I looked okay."r"

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