Chapter 1: Chapter 1

“Oh my god, what are you wearing?!” Kelsey shouted.

 

I turned around as my face burned red with shame. It was my worst fear come to life. My name is Josh Majors and I’m a crossdresser. 

 

It started out as a hobby when I was a kid, dressing up in my mom’s clothes when no one was home and by the time I was eighteen, I had a pretty healthy collection of girl’s clothes that I’d bought online or very discreetly in stores at the mall. It helped that I had a great girlfriend, Kelsey, so I was able to walk freely into a women’s clothing store and simply state that I didn’t know my girlfriend’s exact size, so I was getting two sizes, just in case. Entering college however, presented a new challenge, since I had a roommate, but my roommate went home most weekends so I had the room to myself and I kept all my things in a box hidden under my bed for when I got the chance. I didn’t often use makeup or do anything with my hair, mainly because I was terrified to miss a spot, but also because I just wasn’t that good at it, and I got enough of a thrill from just wearing panties and a skirt so I don't need anything else. This weekend was special because it was the first chance I’d had to indulge in my dirty little secret hobby in weeks, since Kelsey always wanted to go to a movie or, since Fall was in full swing, apple picking or a pumpkin patch, and Kelsey had gone on a weeklong trip back home for her aunt’s birthday and wouldn’t be back until the following day, Halloween.

 

I’d just gotten myself into an orange sweater, with socks stuffed in the cups of my bra to simulate breasts and a plaid skirt which I adored, along with a pair of black tights and chunky black heels to complete the ensemble, (and to save me from having to shave my legs which might cause questions from Kesley), and was so enraptured by the view into my laptop’s webcam as I inspected my outfit, that I didn’t hear the door to my room open.

 

Kelsey had gotten back a day early and wanted to surprise me, but it turned out that she’d gotten the surprise instead. I knew I should have locked the door, but with both my roommate and Kelsey gone, it hadn’t seemed important to do, since no one else would just wander in unannounced.

 

“Kels! I… I can explain!” my face burned red with shame.

 

“Josh, you’re… I don’t, I don’t understand!” Kesley sputtered as I stood frozen to the spot.

 

I’d be lying if I said I hadn’t run through this exact scenario in my head dozens of times, but it was always theoretical before, not something that would actually happen. I was careful! At least I usually was. I wanted to plead with her, to tell her that this was a dumb bet or that I was being blackmailed into it, but I couldn’t lie to her, no matter how hard I wanted to.

 

“Babe,” I reached out to grab Kelsey’s hand, but she recoiled in disgust.

 

Seeing that look on her face, of pure revulsion, shattered my heart into a million pieces.

 

“I can’t believe you’re a sissy!” Kesley started to back up towards the door. “I’ve got to get out of here!”

 

“I’m not…” I started to sob as my emotions got the better of me and I crumpled to the floor. “Please, Kelsey…”

 

“We’re through, you… you freak!” Kelsey slammed the door as she left, leaving me, still in a skirt and heels, collapsed in the middle of the room.

 

Processing what had happened took a while, and it was pure instinct that led me to undressing and tossing everything back into the box. I tried to text and call Kelsey, to no avail, and I felt angry. Angry at losing my high school sweetheart over this stupid hobby! Kelsey was right, I am a freak! At least if I was transgender, I could have a chance at being normal, but I’m not trans, I’m a boy. No, I’m not a boy, I’m a sissy freak who dresses like a girl! Why couldn’t I just be normal?!

 

Staring at the box of clothes sitting in the middle of the room, I shouted at it.

 

“This is all your fault!” I said as I got up and kicked the box across the room and returned to sit down on my bed, burying my face in my pillow.

 

Over the next few hours, every time I looked at the box, every time I remembered it was in the room, I felt the shame returning, bubbling back up, so I did the only thing I felt I could do to get rid of the feelings, get rid of the box. I couldn’t change the past, but I could change the future and make sure I never got caught like that again. And the best way to not get caught is to not do the thing in the first place. The box was going in the dumpster.

 

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As I walked towards the dumpster with my box in my hands I wondered if Kelsey was going to tell all of our friends about my crossdressing, hell, what if she told my parents? They acted liberal, but they’d probably disown me, not to mention all my friends, both here and back home… I’d be ruined! I was so engrossed in thought that I didn’t realize where I was going and slammed into a young woman who had also been distracted, staring down at her phone, knocking both of us, and the box, to the ground. Some of the clothes tumbled out of the box and I wanted to immediately scramble to pick them up, but chose to check on the young woman first.

 

“I’m so sorry!” I exclaimed. “Are you hurt?”

 

“I’m fine, are you okay? I guess I wasn’t looking where I was going,” she chuckled.

 

“Me either.” I said as I reached a hand down to help her up.

 

It was at that moment that she looked down at what had fallen out of the box, then back at me.

 

“I uh… just broke up with my girlfriend, so I’ve got some stuff to toss out.” I said, hoping she’d believe the lie, and why shouldn’t she? It’s not like I’m still wearing the clothes!

 

She was wearing a pair of ripped skinny jeans and a black hoodie with a backpack slung on her shoulder, all of which she brushed off before kneeling down and helping to pick up my fallen clothes and returning them to their box.

 

“I see… Well, I bet you’ll want to take your mind off the breakup, so here’s an invite to Gamma Alpha Lambda’s Halloween bash. We’re holding it with the Beta Omicron Upsilon frat at their place on Greek Row. There’s gonna be food, drinks, good music, why don’t you drop in?”

 

She handed me a small paper invitation that she pulled out of her backpack labeled with the same wording, which also read “Costumes Are Mandatory”.

 

“I don’t think I can go, I don’t have a costume ready.” I said.

 

A day earlier, I might have been able to come up with a way to convince Kelsey to go with me dressed up, maybe even in one of my own outfits, but now? I didn’t much want to be myself, let alone a crossdressing version of myself, but there was no one else for me to be.

 

“Don’t worry, I know someone who can help you.” the girl smiled and rummaged around in her bag for a piece of paper that she scribbled something onto. “Just go to this address and see my friend Tabitha, and tell her Max sent you.”

 

“I don’t know…” I stammered.

 

“Trust me,” Max grabbed my hand and squeezed it. “Go to Tabitha, get a costume and come to the party. You won’t regret it.”

 

“O-okay.” I said, I didn’t know why, but I trusted her, even though I didn’t know her. “I will.”

 

“Great, see you at the party!” Max beamed as she walked away, leaving me standing next to the box.

 

I sighed and picked the box up, walking the rest of the way to the dumpster and tossing it in. Maybe if this Tabitha person can make me a manly enough costume I can find a way to win Kelsey back…

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