Cassie’s College Journey — Part 12

Sorority Girl Costume

Cassie Smith
11 min readFeb 14, 2024

Please note, this is Part 12 of a series. I hope you enjoyed reading Parts 1–11.

The alarm on my flamingo pink iPad signalled Friday had begun, the day of the Halloween party. I quickly pulled off my cream-yellow tee and pulled on my cute canary yellow sport bra and wriggled into my matching canary yellow yoga pants over my silky pastel-yellow thong, maintaining its firm suppression of my clitty and privates.

Finishing off what had become my favourite yoga ensemble, with sunshine yellow socks and hair scrunchy, I pulled on my lightweight canary yellow jacket and went downstairs, surprised to see Harry already up and preparing breakfast. He smiled sheepishly and told me he woke up early. I could sense he was a bit anxious, which was entirely new territory, as he had always been rock solid and unflappably confident.

We had a quick, but unusually quiet breakfast together, Harry preoccupied, and me, trying to figure out a what was going on, getting more concerned by the minute.

Before Harry headed out the door, he asked if I could be ready for the Halloween party by the time he got off from work. I told him I had the entire day, no school classes because all my professors were realistic about college kids and Halloween parties and had “unofficially cancelled” all classes.

I asked Harry if he was still planning on attending as a frat guy and if he wanted me to wear Tiffany’s sorority sweatshirt. With a puzzling look on his face, Harry asked if I was willing, and also if I could “pull it off”.

Butterflies swarmed in my tummy and the happy neurons skipped around, as I reassured him, that I would try my best. With visible relief, Harry thanked me and left for work.

I cleaned up the kitchen and did my yoga classes, my mind trying to process both Harry’s behaviour and words. Clearly this Halloween party was a really big opportunity for his career, and he was anxious.

After Yoga, I fixed myself a fruit smoothie and thought about Harry while opening my flamingo pink iPad to do some searching on the internet. I couldn’t find anything on this division at work he had created the presentation for. They must be a closely held secret at his company.

What did Harry want, but was afraid to ask? Did he want me to dress fully and passably as a girl? If so, how did that help him at work? Was it some sort of a joke he planned to spring on people? I couldn’t bring myself to believe this option. Harry had been true to his word to never make me feel “judged” for wearing Tiffany’s girly clothes. If anything, he had been positive encouragement for how good I looked, which had been boosting my confidence.

Did he want a pretty girl as his date, but had no one to ask? Maybe, but I was pretty certain I could call Brittany or Megan or practically any of the girls table and they would jump at the chance to be on Harry’s arm. Of course, they would probably get excited and overplay their hand, maybe trying to set up the next date with Harry.

Maybe that’s what Harry wanted, a known quantity whom he felt comfortable with, who would step back and support him while he focused on networking at this work party.

None of this made sense to me, I couldn’t read Harry’s thoughts and had lost my chance to ask at breakfast.

I could only go with what I knew for certain. I knew Harry needed to go to this Halloween party and it was really important for his career. I knew Harry asked me to attend as his “+1” and he confirmed that he wanted me to wear the sorority sweatshirt and more importantly, to “pull it off”, whatever that meant.

I tried searching on the internet how to support Harry for this party. After a bunch of failed search results, it dawned on me that I might need to change the question. What if I asked as if I was Harry’s girlfriend. This made me pause, uncertain how to wrap my head around this, however my pleasure neurons started dancing and the butterflies cautiously stretched their wings.

I hesitantly typed in: “How to support my man at a Halloween work party?”

Tons of helpful girly magazine articles popped up.

With a sigh of relief, I dove into the articles and sipped on my fruit smoothy.

The articles suggested that most men viewed having an attractive girl on their arm, projects success. For a work party, a girl has to be careful, from a patriarchal viewpoint, she is an ornament to enhance, but not steal the spotlight. The fine line she must walk, is to be sexy, but not slutty, it must be clear she is dedicated to her man, and not looking to “trade-up”. The costume and makeup choices would be key.

Armed with info from the girly articles, I went up to my tastefully pink and grey ultra-feminine bedroom to look for the clothing for my costume.

I immediately found the sorority sweatshirt. It was light grey with some Barbie pink and powder blue monogrammed Greek letters. I could always pair this with skin-tight jeans, but that wouldn’t be very sexy, the girls table at lunch would not give a high score for this ensemble.

I looked through the closet and located a baby pink and cornflower blue plaid pleated miniskirt that would go perfectly. It even had this cute snow-white frilly lace on the hem. I could hear applause from the girls table, while I felt dopamine rush over me as the pleasure neurons danced.

Next question, what shoes should I choose? I found some brown flats that could work, though the girls table wasn’t enthusiastic with this option.

I would need some sort of socks. I looked through my socks and found a girly pair of cotton-white ankle socks with frilly white lace. Those would match the frothy snow-white lace on the skirt, as the girls table nodded their support.

I pulled out the flamingo pink iPad and looked at schoolgirl costume ideas. Most of the girls wore high heels, and some wore them with frilly socks. I went back to the shoe shelves and located a pair of midnight black heels and a super cute pair of bubble-gum pink heels. Could I learn to walk in high heels, in a day? The girls table nodded in affirmation while the pleasure neurons bounced frenetically.

I tried on the cute bubble-gum pink high heels and dopamine crashed over me. Perched precariously in the heels, I felt wobbly, but didn’t fall down immediately and the girls table broke out in applause.

My tummy was complaining that it was time to eat, so I cautiously walked down the stairs, in the pink high heels, gripping the rail tightly, relearning how to walk.

I fixed myself a light salad and ate while digging through the internet. The cross-dresser sites I had found, had some helpful posts on how to walk in high heels, how to adopt girly mannerisms, and how to speak like a girl.

I also dug around and located how-to videos for makeup. Exhausted, mind processing all this new information, I decided to head back to my tastefully pink bedroom for a quick nap.

Walking back up the stairs, perched in the bubble-gum pink high heels, I could feel that I was starting to get the hang of it. The heels were pulling my calves and thighs taunt, while pushing my derrière back and out.

Back in my tastefully pink and grey girly bedroom, I stripped and replaced the canary yellow yoga outfit with my cream-yellow tee, and remained in my silky pastel-yellow thong, my imprisoned clitty begging for escape, the satiny strip of fabric hugging my perineum. I nestled under the smooth dark-pink sheets, gently caressing my silky legs, and soothing weight of the rosewood-pink comforter pressing down and fell asleep, mind still trying to process Harry’s behaviour this morning.

Waking up refreshed, I took a long, hot shower, paying special attention to my hair. While my hair was soaking up the girly conditioner, I double-checked that my legs were smooth and hairless, touch-up shaving where needed, and also, slowly and carefully, my privates.

Rinsing out the conditioner, I towelled off and used the appropriate girly lotions in the correct spots on my body, paying considerable attention to my legs, because they would be on display tonight. I blushed and felt confused by these thoughts, but my happy neurons danced, and a wave of dopamine rushed in to help sooth my nerves.

Donning my coral peach silky robe, I sat at my make-up counter in the fuchsia pink chair and dried my hair, while making some quick searches on the internet for schoolgirl hair options and decided to go for the cute version and pulled my hair into pigtails. The girls table was back and gave a “thumbs up” for this decision.

Next makeup. I remembered the girls table explaining that it was like paint for the face. They all thought I would be great at it because I saw colours and shades so well.

After much searching, I found a look I thought Harry would like and matched my facial structure well. I started, and quickly fell into my “art zone”.

For me seconds, and for the clock on the flamingo pink iPad, two hours later, I viewed my results in the mirror.

The girls table jumped to their feet in enthusiastic applause.

My dark-blonde hair pulled into high pigtails and my rose-pink cheeks and bubblegum pink painted lips evoked a girlish innocence while my dark-brown eyes were highlighted with a retro 60’s azure blue eye shadow and cat-eye eyeliner that evoked a more mature and provocatively intelligent look.

A tsunami of dopamine crashed over me while the happy neurons ricocheted around my brain.

Studying my reflection on the mirror, I instinctively started searching for pink ribbons to tie in my pigtails. The girls table cheering me on.

I studied my hands. They looked thin and feminine, thanks to my recent discovery of manicures, but painted nails would take this up a notch, the girls table nodding in agreement.

While looking for a suitable shade of pink nail polish, I also located some press-on nails, but stopped and considered how I would get dressed once I painted my nails. The polish would need time to dry.

Drifting over to my lingerie drawers to search for a suitable pair of panties to wear, my pleasure neurons frantic and my hairless clitty suffering from a stiffie, rubbing against my silky coral peach robe.

Looking through my panties, I located a spectacular pair of pearl white satin bikini panties that appeared to be exploding with lace. The edges of the leg openings had dainty frothy pearl white lace, while the derriere had rows of long pearl white lace, and the top front satin panel had a cute rose constructed of satin and lace. These gorgeous panties reminded me of something a French Maid would wear in the crossdresser fantasies I had discovered.

I remembered the girls table chat about choosing the right panties for your outfit, because you would accidentally (or on purpose for the intended person) proved a titillating peek, especially for Halloween, and and I knew these were perfect. The girls table conferred and nodded in agreement, while the pleasure neurons bounced happily.

Laying back on my dark pink sheets, I pulled on these sensual peal white panties and securely tucked my protesting clitty inside. As I had grown accustomed to, once everything was tucked inside my panties, a huge wave of dopamine washed over me.

Sighing in relief, and catching my breath, I rose and pulled on the baby pink and cornflower blue plaid pleated miniskirt with the snow-white frilly lace on the hem and the light grey sorority sweatshirt with Barbie pink and powder blue monogrammed Greek letters. I pulled on the cotton-white ankle socks with frilly white lace and the bubble-gum pink high heels and turned to look in the full-length mirror.

This was close. This was really close, but the sorority sweatshirt was flat against my chest. I quickly went to my lingerie drawer and looked for a bra and something to fill the bra with. I quickly found a pearl white lacy bra that had some built-in pads. I pulled off the light grey sweatshirt and struggled a bit, figuring out how to fasten and wear the bra, adjusting the straps until they felt snug and comfortable and pulled the sorority sweatshirt back on.

Again, the girls table stood and cheered and applauded while my pleasure neurons danced gleefully, and dopamine washed over me. I was pleased with the results and hoped Harry would be as well. Thoughts of Harry seeing me in this outfit, and his hopes for reaction, caused the butterflies in my tummy to join the celebration and tingly feelings in various parts of my body. The pink and blue plaid pleated miniskirt accentuated my hips and derriere, making them look pleasantly fuller, while making my waist a bit thinner. It was a bit shorter than I anticipated, the snow-white filly lacy hem falling just slightly above mid-thigh on my smooth and silky legs. The bra and padding added breasts to my image in the mirror, reinforcing the feminine silhouette.

I turned a 360 in the mirror, inspecting my outfit and makeup and hair from every angle. I even faced away from the mirror, looking over my shoulder and slowly bent at the waist, mesmerized by the sight of the lacy hem of my plaid miniskirt slowly revealing the backs of my silky legs, muscles pulled taunt by the pink heels and, as the girls table strategically discussed, showing my pearl white lacey panties dripping in frothy lace, as the finale.

Feeling flushed, I wobbled slightly in my pink heels as I made my way back to the make-up counter and practiced sitting in the fuchsia pink stool. I was a bit shocked, that the plaid pleated miniskirt did not cover my derrière when I sat, so my panty covered derriere was directly touching the soft fabric of the seat. I practiced crossing my legs, and then proceeded to follow online videos on how to attach press-on nails and to paint my nails with bubble-gum pink nail polish.

This complete, I looked at the time, and with a sudden panic, realized that Harry would be home soon, so I carefully made my way downstairs, getting used to the pink heels. With the imminent arrival of Harry, my nerves started going into overdrive. Would he like the outfit I assembled. Was it too much, too girly, too sexy, too tame. All these questions swirled in my head while the butterflies in my tummy fluttered about.

Maybe some food and a little bit of wine would help. I walked slowly to the kitchen area, keenly aware the high heels were making my hips sway back and forth as I walked, thighs and calves stretched taunt, derriere pushed out. The snow-white lace on the hem of the miniskirt playfully flirting with my smooth legs, bra straps pleasantly digging into my shoulders, pleasure neurons frenzied and dopamine lapping over me.

My bubble-gum pink long nails nearly dry, I carefully prepared a cheese and fruit platter for Harry and myself, poured myself a glass of white wine and readied a glass for Harry, when he returned from work.

I walked around the townhouse, practicing walking and sitting and my gestures and speaking to myself in, what I hoped was a feminine voice, sipping on wine and trying not to shake with nervousness.

Suddenly I heard the garage door and Harry’s heavy tread coming up the stairs. The butterflies frantically swarming in my tummy.

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Cassie Smith

After years of denial, I have accepted that I identify as a Sissy. I hope to post musings about the Sissy Journey. Also some naughty stories.