Tales of a Secret Femboy (Ch. 01)

Tales of a Secret Femboy

The chilly October wind felt like it cut down to my bones as I walked the tree-lined path leading to my campus apartment. All around my feet, the mix of orange, yellow, and red leaves whipped around in the breeze, making a raspy sound. This time of year was my absolute favorite. Spooky Season, I liked to call it. Scary movies, horror novels, haunted trails. I loved all of it. Luckily, my college was nestled in the heart of the Midwest, the crown jewel of the Halloween holiday. Black and orange decorations danced across all the buildings and dorms. It made my heart feel happy. I swiped my key card and entered into my apartment.

"Hey Alex, I'm home!" I chimed to my roommate, as he sat watching the latest horror series he was dug into. He looked up from the show, giving a soft smile.

"Hey Sammie, how were classes today?" He asked, both of us still learning about each other as we had only been roommates for a little over a month now. He was really nice, and a bit of a gamer nerd like me. We clicked well.

"Oh not so bad, I guess. Only 4 papers due by Sunday." I said in a sarcastic tone with a coy smile.

"Damn... sorry dude. Keep your head up, at least you have your looks!" Alex replied in kind with sarcasm. I couldn't help but feel like sometimes he was... I don't know... flirting with me? But there's no way, he knows I'm dating Sarah from back home. Plus he seems straight as an arrow.

"Yay me!" I jokingly reply. "I'll be in my room, if you need me."

As I walked back to my room, book-bag heavy with textbooks, I couldn't help but get a little bit giddy. My stunning girlfriend Sarah had messaged me four times as I walked over here, and I hadn't checked them yet. But I kind of knew what it would be. She attended a different college about an hour away. She got accepted into their highly ranked art program, so we had to go our separate ways. But we were trying to make long-distance work.

I opened my phone, and clicked on her name in the text messages app. I smiled like a dork as I saw she sent 3 pictures and a text along with them. Her text read, "I think you need to rock these undies for me, my little soft boy." Along with several kissie and heart-eyes emojis. My face grew warm with blush as I scrolled through the 3 photos, all of them a different set of soft, cotton panties with orange, black, and purple Halloween designs. This is my favorite part of being a secret Femboy. My girlfriend gets to pick out all the adorable outfits, and she has great tastes.

"Hmmm... no thongs this time?" I send back, with blushing emojis and pink hearts. All of the undies she sent were full cut, to show off the Halloween designs.

"I suppose I'll just have to see what's hidden under all that cotton. Especially with your little bulge poking out. All excited to spurt cummies for me in under 30 seconds." She replies, heart eyes emojis and laughing emojis reinforcing my smol-penis femboy status to her. She knew exactly how to press all my buttons to get me worked up.

"Ugh... not fair, baby. I want these undies NOW." I playfully typed. "When will they get here?" I hit send.

"Did you not see them at your apartment door? It says they've been delivered. I wanted it to be a surprise since it's your favorite month!" She texts back.

"Oh really? That's so sweet. But I didn't see them, not at the front door at least." I reply back.

"Hmm... maybe check with your roommate? Maybe he brought it in and forgot to tell you?" Sarah asked.

"I'll check! But thank you for the surprise panties, baby. You didn't have to do that!" I reply, as i walk out of the room, finding Alex in the same spot.

"Hey uhh, did you bring in a package for me? My girlfriend sent me something." I asked Alex, a bit embarrassed by having to ask. Especially knowing the contents.

"Oh, uh, yeah, I totally forgot about that. Here it is bro." He says, handing me the package from the coffee table next to the couch he was sitting on. I smile and take the package thankfully.

"Thank you! I'm glad it wasn't taken from our doorstep." I say, only half joking as I know college kids are always doing stupid stuff like stealing packages. I walk back to my room, eager to break out my new girly underwear. I text Sarah immediately that I've found the package.

"Ooooh I've got it! Luckily Alex brought them in for me." I send with a smiley emoji.

"I guess you owe me a little femboy photoshoot, honey buns." Sarah texted back with a sly face emoji, using her nickname for me ever since she saw my butt in cute panties after dating for roughly 3 months. I fell for her dominant female vibes very quickly.

"Ahhh I knew these undies weren't free. You just want to see my butt in them." I send back with wide eyes emoji, playfully flirting. As I set down my phone and grabbed a pair of scissors, I noticed the packaging had a clear cut in the top of it, with tape hastily planted over it to cover it up. I frowned a bit, confused. Maybe the delivery guy accidentally cut it and then re-taped it? But that didn't make sense, why would he need in it?

Suddenly, my heart dropped. Alex. What if he had opened them on accident, thinking it was his package? My mind swam with the possibility that my roommate had opened a package from my girlfriend to me that was full of girly, spooky panties. I dreaded the thought of that. I would never be able to live that down. What if he told everyone? I would be the laughingstock of college. I forced myself to stop thinking, and calmed my heart rate. Right now, I needed to try on the panties and take some pictures for Sarah since they were a gift she was excited about. I was determined to try and suss out any information I could from Alex later about the contents of the package, if he even knew what was in them.

I opened the package, and spilled out the colorful, spooky undies onto my desk. I felt a little too excited to have these sent from a girl who was so out of my league. It was like a dream, and yet... I was living it. I quickly strip my baggy boy clothes, which I wear to hide my feminine frame. My shapely hips and bubbly boy butt are sculpted perfectly when I glance in the mirror, happy at the progress I've made in the gym. I slide on the orange panties with little bats on them. I get an idea and slip on a pair of knee-high Halloween socks, completing the look. I lie down on my bean bag chair, and take a picture of my adorable undies and socks, my little bulge growing already.

"I found the undies baby... and I think they fit quite nicely." I text Sarah, adding pink heart emojis.

"Fuck. Why are you just the cutest soft boy ever?" Sarah replies, adding heart-eyes emojis to emphasize that she loves how they look.

"Hmm... well I do have a girlfriend who keeps me in the cutest outfits ever." I reply back, smiling like a dork. As I smile, my small cock continues to eagerly rise.

"That is true... you've had some help. But I bet we can get those panties all warm and gooey pretty fast, can't we baby?" She texts back, with suggestive emojis.

"Ugh... I might already be leaking..." I reply, looking down at my poor eager little dick that's creating a wet spot in the new panties. I've always been so bad at premature ejaculation, and Sarah has mastered the art of femboy undie-cummies.

"Awww already worked up, baby? It would be so bad if you ruined your undies, just a few feet from your roommate. What would he think? You being a total soft boy that wears panties on campus everyday."

As soon as I read her text, my cock strains in the soft, stretchy fabric of the new panties. I moan softly, clenching my thighs together. She's so good at manipulating me, even over text. I feel like warm putty, molded in her hands. I begin to type back.

"Omg... I couldn't handle him knowing. Actually... the package you sent seemed like it was open and resealed when he handed it to me... I, I'm not sure if it was him or not." I admit to Sarah, my heart racing at the admission.

"Wait- your total gamer roommate found your panties? God that's making me wet. How does that make you feel baby?" Sarah asks.

"I... I don't know... I'm just worried he'll tell people." I say nervously, my cock shivering with excitement.

"Honey... what if he wants to see you in them? Maybe he jerks off thinking about your cute boy butt strutting around the apartment in panties like a boy toy for him." Sarah replied, deepening the dirty-ness as she always so perfectly did. As I read that, my mind raced at the thought of a boy jerking off to the thought of me in panties... and out of nowhere, BOOM, my gooey white hot jizz began to spurt from my little cock inside of the underwear. I gripped my bean bag chair, groaning as each rope emptied into the soft fabric, my toes curling in pure soft boy delight in the ever sought-after hands-free orgasm. I was so not prepared for the intensity, and I finally relaxed all of my tensed muscles, panting for breath. I picked up my phone, Sarah still waiting for a reply.

"Ummm... this is so embarrassing. I just made cummies without touching myself..." I texted her.

"FUCK. That's so hot. So you like being a lil gay for Sar Bear? We can have so much fun with that baby. God... I'm about to fucking cum riding this huge black dildo." She replies back, feeling my face fill red with shame as she talks about that giant black dildo she loves, how it can reach places in her I could never dream of reaching.

"Ugh... please cum so hard, my goddess." I say, using a nickname I had selected for her since she was so out of my league.

After a few minutes of radio silence, presumably while she rode that big black dildo like she needed it's babies, she finally replied.

"God I don't think I've ever cum so hard... I literally squirted on this thing. All because my BF is a lil secret gay boy and he never told me!" She texts, with little hearts and kisses to tease me even more.

"I'm not gay, alright? That was just like a super dirty text I wasn't expecting..." I say back, weakly defending myself as I lay there in soiled cum-undies.

"You're right, you're not gay... you're bisexual!" Sarah replied with laughing emojis. I blushed even in the privacy of my own room. I didn't expect my girlfriend teasing me about my sexuality to have an effect on me.

"Whatever, I like GIRLS. I'm dating you, and we have sex like all the time!" I reply back, trying to convince myself as well.

"Oh honey... we don't have "real sex." That can only happen with real men. I just help you make cummies, and I enjoy my dildos. I mean when is the last time you've been allowed inside me?" She replies back with snarky emojis. I feel a little embarrassed, and open my notes app to find the note where I keep track of days since I was allowed to have any pussy.

"Ummm... 64 days ago." I text back, along with a humiliated emoji.

"See? So don't pretend like you're somehow out here owning pussy! You're a lil soft boy and that's fine! The world needs you. But it also means you're into boys." She says, adding laughing emotes for emphasis. I squirm in my bean bag chair, feeling my cock begin to grow again, but knowing I need to compete some homework.

"I don't admit to any of that!" I reply back, jokingly. "I need to write a few papers. I'll call you later, my love?"

"Yes I need to do some work as well. Stay cute, and send me some panties pics!" She replies and I smile. Then quickly another text comes in, "Ooh and tell me if you catch Alex staring at that cute booty of yours!" With a winking emoji in tow. I giggled but set the phone down, determined to get at least one paper done after I cleaned up the gooey mess in my panties.

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