Cassie’s College Journey — Part 13

Halloween Party

Cassie Smith
16 min readFeb 16, 2024

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

I heard the garage door closing, followed by the familiar heavy footsteps of Harry climbing the stairs. My heart pounded in my chest, and I felt lightheaded, as I moved behind the kitchen counter, suddenly terrified for Harry to see me in a skirt and makeup.

As I gripped the kitchen counter tightly, to keep my hands from trembling, Harry rounded the corner, and saw me, with my dark-blonde hair pulled up into high pigtails held with baby-pink ribbons, retro 60’s azure-blue eye shadow, Bambi false eyelashes, and cat-eye eyeliner highlighting my dark-brown eyes, rose-pink cheeks and bubble-gum lipstick painted lips. My light-grey sorority sweatshirt with Barbie-pink and powder-blue monogram Greek letters, pleasantly filled out, giving me the illusion of small breasts, thanks to the pearl-white lacy bra’s helpful pads.

Holding my breath, afraid to move, heart racing, I watched Harry stop dead in his tracks, smile wonderfully and with a sparkle in his dark-blue eyes say: “Wow Casey! I’m stunned and impressed.”

I blushed warmly and felt tingly all over, the butterflies swarmed in my tummy and dopamine crashed over me, as I slowly walked out from behind the counter, so Harry could see the rest of my outfit, the baby-pink and cornflower-blue plaid pleated miniskirt with the snow-white frilly lace on the hem, the cotton-white ankle socks with frilly lace, the bubble-gum pink high heels, and a considerable amount of my bare, silky-smooth legs on display.

Holding my breath, butterflies swarming in my tummy, I watched Harry’s eyes travel from the top of my head to the tips of my toes and back up to my eyes, before he spoke again: “Casey, I’m speechless. I asked if you could pull this off, and you exceeded my hopes, far beyond what I thought possible. I don’t know how I could thank you enough.”

I blushed deeply, while a tsunami of dopamine washed over me, the pleasure neurons skittered, and I felt tingly feelings all over. I nervously told him, if it’s too much, please tell me. I can change from the skirt to jeans and clean off the makeup. It wouldn’t take any time at all.
Harry approached and firmly grabbed my narrow shoulders with his strong masculine hands. Looking down at me, despite my 3” tall high heels, he smiled and told me that I looked perfect. I swooned with relief, and happiness, butterflies taking flight as another wave of dopamine crashed over me.

Harry spied the wine glasses, gathered them, and proclaimed this deserves a toast. He handed me my wine glass and took his own. We clinked our glasses and took a sip, Harry staring at my bubble-gum pink manicured nails. Smiling warmly and fondly, Harry suggested we sit in the living area, for me to go ahead, and he would bring the snacks I had prepared.

I carefully walked to the living area, still getting used to balancing on the 3” tall pink high heels, my hips gracefully swaying slightly, which caused my pink and blue plaid pleated miniskirt to delightfully swish from side to side, while the lacy white hem playfully teased and caressed my silky-smooth legs. Pleasure neurons happily dancing.

As I reached the couch, I looked over my shoulder, somehow feeling Harry’s eyes on me, and was rewarded to see him gazing at my derrière with an expression I both understood and somehow felt thrilled by. The girls table was right, there was something satisfyingly naughty and empowering seeing a man notice you. The butterflies and tingly feelings flitted around while a warm wave swept of dopamine flooded in.

I carefully sat on the couch, smoothed out my plaid pleated miniskirt, again alarmed how short it was, my panty covered derrière directly against the couch cushions. I felt a bit vulnerable how exposed my body was, how thin the fabric of my pearl-white bikini panties was, and thankful for the cross-dresser advice regarding tucking my small clitty snug against my smooth perineum, which provided a nice, flat feminine front to my pretty panties.

Smiling excitedly, Harry brought over the fruit and cheese platter I had made, sat in his expensive masculine leather chair, and proceeded to tell me how delighted he was with my costume and that I looked great. I blushed and lapped up the praise like a kitten with a bowl of cream, tingly feelings and butterflies playfully chasing each other.

Harry suggested we agree on our cover story. He said the truth always works the best because you don’t have to consciously remember it. We met a while ago at our mutual art classes, bumped into each other last week at the diner and caught up, went out for ice cream a few nights ago and Harry invited me to this party as his “+1”.

I nervously agreed, my mind spinning that Harry wanted to introduce me as his date, while wearing this outfit. Butterflies gleefully swooping around. Harry continued, asking me how I felt about the name Cassie. It was like Casey, but a more feminine name.

I felt a strange warm glowing feeling inside and quickly agreed, repeating “Cassie” and how Harry said it over and over in my head.

Harry glanced at his watch and suggested that he should get changed, while I check my makeup and perhaps pack a small “repair kit” and grab my coat.

Harry smoothly rose to his feet, offered one strong, masculine hand, which I grasped with my now dainty bubble-gum pink manicured one and he effortlessly pulled me to my feet. Standing close to Harry, I couldn’t help but notice again, that even with 3” heels, he still towered over me. Tingly feelings skittered about while the butterflies swarmed.

Harry took my wine glass and everything to the kitchen area, while I carefully walked to the stairs, more comfortable in the bubble-gum pink high heels with every step.

Harry caught up with me halfway up the stairs, and I suddenly remembered just how short my pink and blue plaid pleated miniskirt was. I glanced back at Harry and his eyes were fixed to my derrière swaying back and forth, he clearly had a good view of my pearl-white satin panties with all the frothy lace. I squeaked, and instinctively moved one manicured hand to hold my pleated miniskirt down as I had seen girls do, and Harry looked up to my eyes with an amused grin and naughty twinkle in his eyes.
I blushed deeply while the butterflies fluttered about and felt those, now familiar, tingles in wonderful places.

Back in my tastefully pink feminine bedroom, I refreshed my makeup, checked my hair and located a small makeup bag to pack some essentials. I looked for a coat to go with my outfit and tried the dark-pink coat I wore with Harry art shopping and for ice cream. It looked perfect, the hem of the coat just below the snow-white lacy hem of my baby-pink and cornflower-blue plaid pleated miniskirt.

Back down the stairs where Harry was waiting for me. He smiled broadly and unexpectedly grabbed my shoulders firmly with his strong masculine hands. Submissively looking up at him, despite my 3” tall pink heels, he told me in his deep resonant voice he truly appreciated my going with him to this party. Again, the butterflies fluttered about, and I felt tingles all over my body, while we both went downstairs to catch the Uber Harry had called.

Stepping outside Harry’s townhouse wearing a pleated miniskirt was surreal. I immediately felt a cold October breeze playfully swirling around my silky-smooth legs and flirting under my pink and blue plaid miniskirt and caressing my satin panty covered derrière and tightly tucked clitty. I felt even more vulnerable than sitting on the couch earlier, which for some reason caused the tingly feelings to intensify.

Harry protectively held my arm, to which I was grateful, then opened the door to the Uber and helped me inside, while I futilely tried to avoid flashing my pearl-white satin bikini panties. Once inside the car, I was trembling with nervousness. Harry must have noticed, because he reached over and reassured me by holding my small bubble-gum pink manicured soft hands in one of his large manly ones, leaning over and whispering, his hot breath in my ear, not to be afraid, I looked wonderful and he was proud of me, and he would protect me. The dopamine washed over me in a strong wave, delicious tingly feelings in delightful places and I relaxed a tiny bit.

The Uber pulled up to a high-class hotel, a doorman opened the car door for me and respectfully looked away, so he did not see me flash my pearl-white satin bikini panties getting out of the vehicle. Harry was instantly by my side, linking my arm in his, as we walked into the lobby.

Harry protectively guiding me and preventing me from stumbling, I heard the click-clack of my bubble-gum pink heels on the marble floor of the lobby and felt my hips gently swaying back and forth with every step, causing my baby-pink and cornflower-blue plaid pleated miniskirt to swish, and the surreptitious glances every man in the lobby, and most women were giving me. Blushing, butterflies flitting about, I squeezed Harry’s strong, muscular arm tighter and tried to control my breathing and fast-beating heart.

We followed signs to the division Halloween party, checked our coats and stood in a queue to enter the hotel ballroom. They had set up a spooky forest photo op area, and every couple was having their photos taken prior to entering the party. When it was our turn, Harry wrapped one strong arm around my narrow waist, pulling me close, while I tried nervously tried to smile for the camera. The camera person, a woman, adjusted our poses, showed me how to “bevel” and best show off my silky-smooth legs, whispered reassuring words, telling me I looked fantastic, the prettiest girl so far, and Harry looked scrumptious, how lucky I was, and quickly took some photos.

After the photos, I instinctively grabbed and held Harry’s firm masculine hand as he led us through the “spooky forest” into the hotel ballroom and the Halloween party. Clearly some money had been spent on this party. The hotel ballroom had been transformed into several movie set like locations. There was a graveyard and a witch’s cave and a mad scientist laboratory and a haunted mansion parlour. It was incredible.
Still firmly holding my small, soft bubble-gum pink manicured hand, Harry steered us towards a drink station and ordered two glasses of champagne, smiled a broad grin at me and toasted “Happy Halloween”.

We heard someone call out Harry’s name, turned and a gorgeous petite redhead with emerald-green eyes wearing a sexy French Maid costume, complete with layers of frilly white petticoats, seamed black stockings and black stiletto heels approached. Harry smiled cheerfully, grabbed a fresh glass of champagne and handed it to her, which she gracefully accepted with her crimson-red manicured feminine hand. Smiling and toasting, Harry introduced me as Cassie to his co-worker Heather.

Heather smiled a beautiful smile and asked Harry where he had been hiding me and why hadn’t he mentioned me. It was Harry’s turn to blush, and he stammered that we just started dating this past week, which caused the butterflies in my tummy to take flight and now I blushed.

Without missing a beat, Heather told me I looked awesome, and demanded a 360 so she could get a good look. I bashfully thanked her and submissively turned 360, pleasure neurons bouncing happily. Harry suggested we sit and chat, and Heather laughingly agreed, stating her stilettos were killing her feet.

We located a small booth in the haunted mansion parlour, Heather and I both sat, femininely crossing our legs and Heather arranging her French Maid dress and layers of frothy white petticoats while I smoothed out my pink and blue plaid pleated miniskirt, again feeling extremely vulnerable that my pearl-white satin bikini panty covered derriere and small limp tucked clitty were against the Booths velvet seat. Heather suggested that Harry go and find some food for all of us while “us girls talk”. Smiling broadly, Harry agreed and left.

Heather turned to me once Harry left, and we compared manicures, she complimented me on my Bambi eyelashes, eyeshadow and cat-eye eyeliner, and we did the whole girl chat thing. I started to relax, and enjoy myself, thankful for spending those days at the girls table at school, because I understood the flow of the conversation.

Harry returned with finger snacky food and fresh glasses of white wine. We toasted and ate and drank and chatted and laughed, Harry having to go get a second round of wine. Heather thanked Harry for scoring an invite for her, to this party. She confided that their co-workers were insanely jealous. Harry responded it was the least he could do, because she had proof-read his presentation to this research division and had helped him refine it.

We had nearly finished up the snacky food when a stunning Wednesday Addams costumed lady arrived at our table. Long jet-black hair in braids, midnight-black mini-dress with crisp paper-white rounded flat collar and chalk-white knee socks and glossy-black patent leather schoolgirl shoes with raised heels, pale make-up, coal-black lipstick and glossy-black talon-like manicured nails. She immediately turned to Harry and told him he was glad he could make it, could he please introduce his friends to her.

I had never seen Harry so nervous. He quickly sat upright, smiled nervously as he shook her hand and turned to introduce Heather, his co-worker, the French Maid and myself, his friend, Cassie, the cute Sorority Girl. Her name was Kristie, and she was the Senior Project Manager for this work division, who’s party we were attending. Heather and I shook Kristie’s hand and thanked her for this amazing party.

Kristie smiled and graciously said she was happy we could attend. She teased Harry for having cornered the two hottest women at the party, and then insisted both Heather and I give her a 360 for our Halloween costumes. I was relieved that Heather, in her sexy French Maid costume, was equally embarrassed and blushed as we stood and submissively showed off our costumes.

Kristie insisted she must have a photo with the two of us and handed Harry her phone. She stood in the middle, sultry Wednesday, while I was to her right, cute Sorority Girl, and Heather to her left, sexy French Maid. Harry nervously took a few photos, while I tried to remember how the photographer girl instructed me to “bevel” for photos.

Kristie then asked me to use her phone take a photo of Harry and Heather and her, with Harry standing in the middle, which I happily did. Kristie then asked for all our phones, so she could take a photo of Harry in the middle, with the sexy French Maid on one arm and the cute Sorority Girl on the other.

After the photos, Kristie insisted that she take the three of us around the room to introduce us to a few people. Harry and Heather looked both surprised and giddy with excitement, like kids on Christmas morning.

Harry reached and possessively grabbed my dainty, bubble-gum pink manicured hand and held it firmly as Kristie steered us around the room.
Kristie led us from table to table, group to group introducing Harry and Heather as the promising Marketing Associates and myself as Harry’s date. The men tried hard not to look at Heather and I like kids looking at candy, while simultaneously looking at Harry like he was an Alpha wolf. The women were mostly friendly, positive and supportive and a few, a bit jealous.

I imagined hungry eyes appraising my pert derrière as it swayed provocatively in my baby-pink and cornflower-blue plaid pleated miniskirt, which made the happy neurons dance and tingly feelings skitter about, encouraging me to add just a touch more movement to my hips as we walked through the party.

Once Kristie had completed a circuit of the room introducing us to various people, she turned to me, and thanked me for my patience, with her pushing work into this party, and suggested we find a quiet place to sit and rest our feet and enjoy some more food and reminded us that it was an open bar.

With a sigh of relief, Heather and I scored and sat in a booth in the haunted mansion parlour, again experiencing that vulnerable feeling of my pearl-white satin bikini panty covered derriere and tucked limp clitty, caressing the velvety fabric of the booth seat, while Heather and I both femininely smoothed our skirts and crossed our legs.

Heather grabbed my soft bubble-gum pink manicured hands in her crimson-red elegant, manicured ones, giving me a squeeze and started gushing how excited she was that both she and Harry had this opportunity to network. Heather was practically quivering with excitement.

Harry arrived, not only with more substantial snacky food, but mixed drinks. I recognised Harry’s favourite, an Old Fashioned, he gave Heather a Chocolate Martini, which she loved, and Harry presented to me a gorgeous, pink semi-frothy dreamy-looking drink, smiling broadly, he said the bartender called it a Strawberry Prosecco Smash.

We toasted to the Halloween party and started nibbling and chatting, mostly Harry and Heather giddy about networking, and enjoying our cocktails. Harry sitting extra close to me, and snaking his muscular arm possessively around my waist, while I savoured the waves of dopamine lapping over me and the pleasure neurons swam and frolicked, I leaned back contentedly against Harry’s broad chest.

I saw Kristie, threading her way through the crowd, in tow some geeky looking guy dressed as a Beaker from the Muppets. Kristie made it to our table, smiled apologetically, and introduced Kevin, one of the lead scientists. We all shook hands, and Kristie asked Harry if he could spare a minute, to which he immediately jumped up, then he and Kevin followed Kristie off to destination unknown.

Heather and I resumed our girl talk, which was enjoyable, Heather being a fun person, laughing about how the men reacted to our costumes while simultaneously jealous of Harry, exchanging phone numbers, when suddenly Kristie appeared bearing replacement cocktails for both Heather and I. Kristie joined us, with her vodka martini, and she apologised for taking away Harry from me and she hoped I was enjoyed the party, to which I affirmed that I was.

Us three girls then chit-chatted for a while. Heather at first incredibly nervous, then warming up. We talked and laughed and complained about how uncomfortable our shoes were and had a really good time. The alcohol was having an effect, and I was feeling more mellow by the minute.

Eventually Harry made it back from wherever Kristie had taken him. He was bearing Blood Moon Shots for all of us, including Kristie. Before we could toast, a photographer appeared, the girl from the entrance to the party, and asked for a group shot. After a few, she turned to Harry and asked him to have his girlfriend sit in his lap.

Before I knew what was happening, Harry grabbed my narrow hips with his strong masculine hands and effortlessly pulled me onto his lap, then wrapped his muscular arms around my slender waist, firmly holding me in place.

I yelped and pulled my pink and blue plaid pleated miniskirt down in the front, my pearl-white satin bikini panty covered derrière now resting firmly against the coarse fabric of Harry’s trousers.

The girls laughed and giggled and leaned closer to Harry for the photo, while I became aware that Harry was wearing boxers under his coarse trousers, because I could feel his very large manhood rigid, and pressing up against my tender, panty clad derriere. The pleasure neurons exploding in activity and dopamine crashed over me.

We toasted to the party, me still nestled in Harry’s lap, feeling tingly and the butterflies swarming, then Kristie thanked us for coming and wandered off, Heather looked at her watch and said it was getting past her bedtime, so the three of us decided to head out.

Both Heather and I were feeling a bit tipsy, and high heels did not improve the situation. Harry laughed and placed a strong arm around each of our hips as we made our way to the coat check, and then the front of the hotel, every man openly watching and jealous of Harry.

The company had made arrangements for private cars to get people home. Harry offered to Heather, that we accompany her home as the first stop, to which she gratefully agreed. The three of us got into the private car, both Heather and I tipsy and failing miserably to prevent Harry from seeing our panties.

Harry sat behind the driver of the sedan, while Heather was on the passenger side, and I wedged in the middle. Harry protectively placed his masculine arm around my narrow shoulders, and I instinctively snuggled close, and rested my head on his chest, the alcohol having caught up.
We dropped a tipsy Heather to her apartment and Harry walked her to her door, I stayed in the middle seat, too tipsy to move.

Once Harry was back in the car, I rested my head against his muscular chest while he placed his right strong arm around my narrow shoulders and held me close. I reached over and hesitantly grabbed his left masculine hand and pulled it to my lap, holding it gently with both my small, soft manicured hands. The butterflies swooping in a dopamine tide.

We arrived home and Harry gently and effortlessly helped me from the car and into the townhouse. Once inside, he scooped me up in his big strong arms and carried me up the two flights of stairs, while I wrapped my arms around his neck.

Harry carefully and tenderly laid me in my tastefully pink feminine bed, modestly adjusting my baby-pink and cornflower-blue plaid pleated miniskirt to cover my pearl-white satin bikini panties with the frothy lace, carefully pulling off my bubble-gum pink high heels and cotton-white ankle socks with flouncy lace, and gently pulled the dark-pink sheets and comforter over me, tucking me in like a caterpillar in its cocoon.

I urgently grabbed his strong masculine hands with my slender manicured hands, pulled Harry close and drunkenly whispered asking if he was happy with me and my costume.

Harry leaned in close to my ear, whispering in his dark velvety voice: “Yes Cassie. I was so proud of you and happy with you and your costume. You were the prettiest girl at the party and made me so happy.”

My butterflies fluttered and dopamine washed over me as Harry gently kissed me on my forehead and I drifted off to sleep.

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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.