Cassie’s College Journey — Part 11

Halloween Invite

Cassie Smith
8 min readFeb 11, 2024

Please note, this is Part 11 of a series. I hope you enjoyed reading Parts 1–10.

Harry and I quickly fell into a comfortable routine over the next couple of days. I would get up early, dress in a colourful yoga outfit and fix breakfast for the two of us. We would have breakfast together and chit-chat before he headed off to work. I would then domestically clean up the kitchen and proceed with two hours of yoga.

After yoga, I would take a shower and change into my drab boy clothes and take my pink bicycle to school, and to classes. Lunch with the girls, still obsessing over their Halloween costumes and back to the townhouse, where I would take another shower, choose something girly to wear for dinner and practice my cooking skills.

I was getting better at cooking and Harry was always very encouraging and praised my efforts, which made me feel good about myself. Post dinner, Harry would help me clean up the kitchen and we would go to the living area to watch one or two episodes of Mad Men. I was starting to enjoy the show, particularly the outfits the women wore. Harry was correct, women dressed much more feminine and classy than they did today.

Post Mad Men, we each retired to our rooms. I would change into a silky thong and comfy tee, followed by a predictable dopamine rush, and curl up in my nice pink bed and continue to go down rabbit holes on the internet regarding boys who dress in girls clothing, trying to understand it all, sometimes pleasure neurons dancing or skittering, and sometimes tingly feelings, before falling asleep.

One thing I found recently, was a lot of crossdressers referred to their phallus as a clitty. They did this to assign a feminine nickname, which caused the pleasure neurons to take notice, and the tingly feelings.

It was Thursday lunch with the girls, and I received a text message from Harry. He told me that he was going to take care of dinner tonight and for me to dress up extra-special.

I was reading the message and couldn’t help but to react. Bethany noticed, and teased me about receiving a text message from an admirer. This caused me to blush, and all the girls giggled.

I pedalled my pink bicycle home, wondering what Harry meant by “dress up extra-special”.

Arriving at the townhouse, I ran upstairs and took a nice long, hot shower. I decided it was time to freshly shave my legs and privates. Stepping out of the shower, I put on my familiar coral peach silky robe, the delicate fabric teasingly flirting and caressing my now freshly shaved legs, my now hairless clitty excited, while I felt the wonderful dopamine rush, that I felt every time I got dressed in girly clothes, the pleasure neurons dancing happily.

I went into my closet to look for something to wear. There was this really frilly white blouse that was ultra-feminine. I had been admiring it for a while, and secretly wondered if Harry approve. I also found a pair of tan shorts, that were cut fully with wide leg openings. Decision made, I moved to my lingerie drawer to locate appropriate lingerie.

I remembered that first pair of panties I wore with the white fuzzy sweater. The white satin string bikini panties with just a little frothy lace around the edges and a small white bow in the front. The pleasure neurons danced excitedly at the possibility, and my clitty tried to stiffen up before it’s imminent imprisonment.

Laying back on my pink feminine bed, I quickly and automatically tucked my freshly shaved and silky smooth clitty inside my sensual satiny panties and felt that much anticipated rush of dopamine and pleasure neurons dancing about. It was a wave of submissive, nearly orgasmic relief to wear pretty panties.

I pulled on the white blouse to discover it was built of a very thin fabric, so thin I could see my chest. I looked through the lingerie drawer and located a half-slip, which would cover my torso and then tried on the white sheer frilly blouse.

Next, I tried on the tan shorts. Once I had them on, I understood they were cut to look like a skirt, the hem of which came just above my knees.
I went to the closet to look for another option, when I heard Harry downstairs calling me.

I ran to the bathroom to check how I looked in the mirror and was pleasantly surprised. The shorts flared out, which accentuated how slim my tummy had become and gave the illusion that my hips were wider and more feminine. The hemline just above my knees exposed my toned and silky calves. The sheer white silky frilly blouse was tailored to perfectly frame my narrow shoulders and tapered in to snugly enhance my slim tummy. The outfit gave me a girly hourglass shape, which caused the dopamine to crash over me.

The lacy should straps of the half-slip were faintly visible through the sheer silky blouse and covered where my breast would be, if I had them. For some reason the pleasure neurons got exited with the thoughts of having perky breasts.

I was torn. This was the nicest outfit I had worn, and I desperately wanted Harry to see me in it. It was also the most feminine outfit and with a little makeup, I could probably pass as a girl, pleasure neurons bouncing excitingly with these thoughts.

Harry had promised “no judgment” and had delivered on that. If anything, he encouraged me to dress girly and consistently praised how I looked.
Harry was home now with dinner, and I was already dressed, so I hesitantly left my ultra-feminine pink and grey bedroom and went to the stairs.

I was nervous, really nervous. More nervous than that first night when I came down these stairs in the yellow sweats and fuzzy yellow sweater. More nervous than wearing the pink fluffy sweater, my clitty tucked in silky pink string bikini panties and skin-tight jeans when Harry took me to the art store and for ice cream.

The second Harry saw me, a tidal wave of dopamine washed away any trace of nervousness or self-doubt. Harry looked at me and beamed with pleasure. This was the most intense reaction he exhibited for how I looked.

“Wow Casey! You look amazing! Love the outfit, especially the skirt. Please give me a 360,” Harry enthusiastically said.

Blushing furiously, secretly relieved and pleased and excited, the butterflies swarmed and tingly feelings all over, I meekly explained they are shorts, it’s just how they were cut, and I didn’t have time to find something else, as I submissively turned so Harry could get a good look at me and my girly outfit from all angles.

Harry smiled broadly and replied: “Shorts or skirt, you look fantastic. A little bit of lipstick and maybe earrings and we could go out on the town.”

The pleasure neurons exploded in a frenzy competing with the butterflies and tingly feelings and dopamine crashed over me.

Unsure how to respond, I shyly smiled, blushed, and thanked Harry for the compliments.

Harry held my chair for me to sit, which I submissively did, then moved to his side and started serving the food. Harry had brought home Mexican, for him a massive burrito and for me a taco salad. He poured wine and excitedly told me about his day. The food, the wine and Harry’s happy optimism were infectious and soon we were talking and celebrating.

Harry explained he had a meeting with that department he had created the presentation for, and it went well, it went better than well. They loved it and were impressed that he had done some “outside the box thinking” and had potentially identified a market they never considered.

This department was hosting a private Halloween party tomorrow evening and had invited Harry to attend so he could meet more of the people in that department. I congratulated Harry, I was so happy for him.

Harry grinned broadly, grabbing my small delicate hands with his large warm ones, looked me in the eyes and said in a husky manly voice: “Thanks Casey. They said I could bring a +1. Would you like to join me as my +1?”

Stunned, pleasure neurons skittering and butterflies swarming, I blushed deeply and replied yes, but what costume should I wear?

Still firmly gripping my frail hands in his strong masculine ones, Harry looked both relieved and happy, as if he had been nervous asking me and replied: “You’ve got tons of options in your closet that Tiffany left behind. I’m confident you can come up with something, you are very creative and resourceful.”

I meekly asked how we explained my wearing girly clothes and Harry relaxed and let go of my hands. He smiled, and explained that it’s Halloween and anything goes, and we can always write it off as a dare.

I relaxed a bit and asked what he was planning for his costume, and Harry responded he was going to take the easy out, and dig up his college frat sweater and just do that. He paused and said at one point Tiffany belonged to a sorority, maybe that sweatshirt was still in my closet.

Dinner complete, I suggested Harry head to the living area and relax, maybe we watch the Mad Men episode about the Kodak Carousel, and I would clean up.

While Harry got the TV ready, I domestically cleaned up the kitchen and dishes. I was so giddy that Harry was so happy, that decided to surprise him and fixed him whisky, neat, while I mixed mine with mineral water.

I took his drink to him, to which he smiled warmly and happily as I nestled into my accustomed seat on the couch, adjusting the skirt-like folds of my shorts until they looked good.

We watched the episode and relaxed with minimal talking, just savouring the moment. The happy neurons frolicking in the gentle waves of dopamine, with my submissively small and soft and limp clitty contentedly tucked into my sensual white satin string bikini panties, and Harry’s calm and happy and strong masculine presence.

Harry was so happy and excited. And I felt happy and excited for him.

Tonight, I would search my closet for the sorority sweatshirt and scour the internet for Sorority Girl Halloween Costume Ideas.

Basking in contentment, it dawned on me this was our one-week anniversary from bumping into each other at the diner.

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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.