Cassie’s College Journey — Part 8

Pink Bicycle

Cassie Smith
13 min readFeb 3, 2024

Please note, this is Part 8 of a series. I hope you enjoyed reading Parts 1–7.

Once again Harry’s polite knock on my door work me up.

“Wake up sunshine, I’m headed to work early. If you’d like to join me for breakfast, I’ll make an avocado toast for you as well,” said Harry in his strong and compelling voice.

I replied that sounded great as I stretched languidly and pulled myself out of my pink comfortable bed. I had slept so well, better than in ages. The hot bath and pampering and grooming last evening had done wonders.

I pulled on the peach silky robe over my pink tee and white cotton bikini panties and quickly went to the bathroom to brush my teeth and fix my hair.

Looking in the mirror, my hair looked wonderfully glossy and full. I pulled it back into a ponytail, opting for a lavender scrunchy and moved to the bedroom to locate a yoga outfit.

Opening the drawer, I immediately was drawn to a beautiful lavender set with a matching jacket. I opened my panty and bra drawer and found a silky lavender thong.

Pulling off my white bikini cotton bikini panties, my penis sprang free from being tucked against my perineum all evening. I quickly pulled on the cute lavender thong and adjusted my member and boy parts to fit inside. I could not achieve a full tuck, due to how the thong was constructed Still, my member was submissively imprisoned in the front of the thong, and it dawned on my just how small my penis was, that it would fit in this very tiny lavender girls’ thong. Suddenly curious, I went back to the bathroom, pulled up the hem of my pink t-shirt and looked in the mirror, both to see just how small my member was, and also at the results of my grooming yesterday.

The girly magazines were correct, I looked so much better in the tiny lavender thong having trimmed and shaved my unwanted hair, my small, now soft and limp phallus, barely visible. I also noticed my legs looked long and slim and silky smooth, which reminded me to apply more lotion, so they stayed looking pretty.

Back to the bedroom to pull on the lavender yoga pants and sport bra. Once again, the girly magazines were correct, it was so much easier pulling on the skin-tight lavender yoga pants now that I had shaved my legs. Quickly locating lavender socks and pulling them on my small and soft feet, the pedicure had done wonders, I ran back into the bathroom inspecting how I looked and finally pulling on the lavender jacket and bouncing downstairs to see Harry.

Harry was bringing the food to the dining area table, heard my light footsteps on the stair and looked up.

Smiling brilliantly, he said: “Good morning, Casey. I see you’ve decided to become a little adventurous in your colour choices. You look amazing! Also, perfect timing, I made avocado toast with scrambled eggs. I hope you like.”

Flustered and giddy with his reaction to my matching lavender yoga outfit, I blushed and thanked him, the pleasure neurons bouncing and a wave of dopamine, as the butterflies took flight and fluttered around my tummy, and Harry pulled out my chair and held it for me while I submissively sat down.

Harry was dressed in a sharp dark-blue suit that complimented his eyes, with a white shirt and yellow tie. He looked happy and upbeat and told me that he had his presentation complete, and he was going to send an email today reaching out to this division at work he had been researching. He thought he had discovered a market they had not considered.

We enjoyed breakfast, complete with coffee and some fruit, savouring the time together. Harry asked if I was taking Tiffany’s bicycle to school today to talk with my professors. I responded yes, I did plan to go after my video yoga class. Harry then reached into his pocket and pulled out two $20 bills and gave them to me in case I needed to purchase a snack or something. I blushed and docilely accepted the money.

With that, Harry looked at his watch and said he needed to go. I told him that I would take care of the breakfast dishes and kitchen. With that, Harry grabbed his briefcase and asked me to wish him luck and he went downstairs. I few seconds later, I heard the car start up and pull out of the garage.

I gathered the dishes and took everything to the kitchen area. I took off my lavender yoga jacket and continued in my lavender sport bra. Thankful that Harry had provided the yellow gloves, I put them on to preserve my soft hands and tranquilly washed the dishes and pans and cleaned the kitchen thoroughly.

Once the dishes were complete, I pulled out the pink yoga mat and proceeded to go through two lessons. Yoga was going great; I could really feel the difference and it was also calming and soothing at the same time. The lavender silky thong felt wonderfull under the skin-tight yoga pants, while the lavender sport bra clung to my torso. Once the lessons were complete, I put away the pink yoga mat and went upstairs to get changed to go to the university.

I remembered my bed sheets were in the dryer, so stopped and quickly folded then, then went into my room, took off the girly clothes and reluctantly put on my boxer shorts, jeans, tee, and sweater. It was astonishing how loose fitting the clothes were and how coarse the fabrics felt against my now silky-smooth skin. I changed out the lavender scrunchy for a brown one and headed downstairs to the garage for the bicycle.

As Harry mentioned, the bicycle was pink. Harry had hung the pink bicycle helmet on the handlebars of the bike along with a locking chain, which still had the key in it. I put on the helmet and took the bicycle out of the townhouse. I realized this was the first time I had set foot outdoors since Harry had brought me home.

I rode the bicycle to the university, found a place to lock it up, and went looking for my professors. I was able to locate all of them in their offices. It took a bit of running around, but I successfully talked to all of them. All the conversations were similar, I told them that I had missed classes because I had some personal issues that I needed to take care of, and had solved those challenges and asked if it was possible for me to make up the missed classes. They all said yes, without hesitation and gave me a list of art materials I would need for this semester and a homework list for me to do to catch up.

Having finished up with my professors, and it being lunchtime, I decided to grab a light lunch, so headed to one of the school canteens. As I was getting my food, I bumped into one of my classmates, and she gave me a big hug and suggested we sit together for lunch.

Brittany was studying to be a costume designer. She was about my height, with honey blonde hair, sparkling blue eyes and she was well endowed in the bust department, which i had found visually appealing in the past, but was somehow feeling jealous now. She was always positive and full of energy, and I had always liked her.

She and I sat and ate lunch and chatted. She told me that she, and the other girls were worried about me as I had suddenly disappeared and none of them had my phone number. I told her the same story as the professors, that I had had some personal issues, but had them solved and would return to class.

Brittany grabbed my hands and told me that she hoped everything was better now. She paused for a second and gave me a look that I did not understand. She suddenly smiled and told me that my hands were so so soft and my hair looked fantastic, I must tell her my secret sometime. She asked me for my phone number, and I had to admit I was without one. Brittany wrote her number on a piece of paper and gave it to me and made me promise that if I ever needed anything I should not hesitate to call. I promised that I would, and she gave me another big hug and we parted.

I found my pink bicycle and rode it back to the townhouse. Once I parked it in the garage, I went upstairs in need of taking a shower, and changing into something nicer and more comfortable. Taking off my boy clothes was an unexpected relief and I jumped in the shower. Once out of the shower, I put on my now favourite, silky peach robe, and applied lotion to my legs and body and dried my hair, wondering what I should do next.

It struck me that Harry had provided all the meals, and I should reciprocate. I didn’t really know how to cook, but I had my pink iPad and the internet and decided to try. The big question next was what should I should wear.

Harry responded very well to my blue chambray blouse and khaki chinos, but I couldn’t repeat again so soon. I remember he liked the skin-tight jeans and the white fluffy sweater. Maybe I could repeat the jeans and find a different sweater that he would like, so I went to my closet and started looking. I immediately saw a beautiful pink turtleneck and I remembered Harry’s positive comment on how I was exploring other colour options.

Choice made, I grabbed the pink turtleneck and jeans and went to my panty drawer. I guess I had pink on the brain, because I saw the most beautiful pair of pink panties. They were exquisite string bikini satin panties with lovely lace, my pleasure neurons danced happily, and a dopamine wave rushed in while now hairless member started getting stiff.

I laid back on the bed as I had done last evening, and pulled the satin pink string bikini panties on and then pushed my boy parts up inside, and pulled my penis back between my legs until it was nestled tight to my perineum. A tsunami wave of dopamine washed over me once everything was in place, nearly drowning the pleasure neurons dancing about, causing me to pant to catch my breath for a few minutes.

I found some cute pink socks and pulled on the skin-tight jeans followed by the fuzzy pink turtleneck and went into the bathroom to find a pink scrunchy for my hair. Checking myself in the mirror, I hoped Harry liked me in this outfit, butterflies swarming in my tummy.

I grabbed my pink iPad and went downstairs to the kitchen area. I searched for easy recipes and compared the ingredient list to what we had in the pantry and fridge. I finally decided on a hamburger casserole, so pulled all the ingredients out.

It dawned on me that I didn’t want to get anything on my fuzzy pink sweater, so I ran upstairs and grabbed the first pink t-shirt I saw. I pulled off the pink fuzzy turtleneck and pulled on the pink tee. It was another crop top. I went into the bathroom to see how I looked and was pleasantly surprised.

I ran back downstairs and to the kitchen area, getting worried about time. I studied and followed the recipe, put the casserole in the oven and set a timer. I thought a nice salad would be good as well, so went to work on making one.

Salad made, I went back upstairs and decided it would be easier if I had just worn the pink crop top under the fuzzy pink turtleneck, instead of running back and forth to my room, so that’s what I did.

Coming back downstairs, it occurred to me, that Harry would be home soon and started getting nervous. I set the table for dinner and checked on my casserole.
I heard the garage door and panicked. The casserole was starting to burn. The edges were already brown turning black. I grabbed oven mitts and pulled it out.

I heard Harry’s heavy tread coming up the stairs and I almost burst into tears. Harry entered the kitchen area and with a big smile told me that he loved my sweater.

I couldn’t keep the tears inside, they burst out, warm and salty and ran down my cheeks. With a puzzled look, Harry immediately grabbed me in a bear hug, his muscles locking my head against his broad chest and patted my head and lower back saying soothing things.

Harry asked what was wrong. Tearfully and embarrassed, I told him I made a casserole for dinner tonight, but I had burned it. Harry grasped my narrow shoulders with his large masculine hands and held me almost kissing distance apart and told me it would be OK, and he was really proud of me for taking the initiative.

Being held firmly by Harry and looking up into those deep dark blue eyes, the butterflies in my tummy swarmed around as a wave of dopamine crashed over me and the happy neurons skittered around my brain.
Harry released one firm hand and reached to my face and gently brushed my tears away. He released me from his strong embrace and my knees felt weak.

Harry turned to the casserole and started inspecting it. He smiled at me and told me that we can avoid the sides, everything else looks good. He then grabbed the oven mitts and proceeded to take it to the dining table.

In a daze, I docilely brought the salad out and Harry returned to the kitchen area and returned with wine glasses and a bottle of red wine, which he opened and poured for the two of us.

Harry then pulled out my chair for me to sit, so I submissively did.

Once Harry was seated, he smiled, and we clinked our wine glasses and drank a sip of delicious red wine. I offered the salad, which Harry served me first, and then himself. We started eating and I started calming down.
Harry asked how my day went and I happily told him all my professors were understanding and they gave me a list of homework to catch up on.

Harry smiled and congratulated me. With a smile he went to the top of the stairs and returned with a tote bag, which he presented to me. Inside were all my schoolbooks I had left at my apartment. I nearly cried again but was able to exert a tiny bit of control. Harry grinned and told me how he located the landlord and convinced him to return the books.

He then told me that he sent his proposal off he had been working on and mid-afternoon he received a meeting invite for Wednesday. He looked both excited and a bit nervous. I congratulated Harry. With the mood now positive, I was able to enjoy dinner.

We ate and talked about our day. Harry again told me he liked my outfit. I blushed and the dopamine started swelling and the happy neurons frolicked about, joining the butterflies in my tummy, soft limp penis safely tucked onto my silky pink panties.

Harry asked if I had sufficient art supplies for my homework, and I nervously replied I could make it work. Harry responded that he would cover some art supplies and then firmly asked if I had a list of needed supplies and then politely demanded I give it to him.

Embarrassed, and reacting to the dominant tone in his deep husky voice, I obediently retrieved the list and provided it to Harry.

Harry accepted the list, glancing at it before putting it in his pocket. He then got up and again went by the top of the stairs and returned with his briefcase. With a delightful smile, he reached inside and brought out an iPhone in a pink case and presented it to me.

Harry said: “You need a phone, Casey. I wanted to call you today, but we don’t have a landline here at the townhouse. This is an old phone Tiffany had. I located it yesterday and stopped by the cellular store and added you to my phone plan. I had them reset the phone and I added my number to your contacts.”

I was so shocked all I could do is meekly and tamely accept.

Harry looked at his watch and said: “Let’s go shopping for those art supplies. Why don’t I wash the dishes and clean up while you put away the leftovers. Your hands are looking much better, and I don’t want to disrupt your progress.

I felt a warm thrill that Harry had noticed my manicure efforts, while the dopamine surged, and the happy neurons danced joyfully, and the butterflies fluttered about, with the praise from Harry.

With that, we proceeded to clean up from dinner. Once I had put away the leftovers, Harry called over from his washing dishes and told me to run upstairs and grab my shoes and a jacket and meet him in the garage.

I was halfway up the stairs to my room when the implications of what Harry said hit me. He expected me to leave the townhouse in these girly clothes. My heart started pounding in my chest, the pleasure neurons suddenly bounced happily around, and dopamine crashed over my brain.

Panting for breath, I nervously reached my bedroom, racked with indecision. If I changed into my boy clothes, I risked displeasing Harry. If I put on my old ratty sneakers and torn coat with these pretty girly clothes, that might also upset him.

With these thoughts chasing each other in my brain, I instinctively went to my closet to the shoe shelves and looked for something to wear. I spotted some cute pink and white sneakers and quickly put them on. They fit perfectly and went with my fuzzy pink turtleneck sweater and skin-tight jeans. I then focused on a jacket. Looking at the options, a dark pink mid-thigh autumn jacket looked the best.

Dark pink jacket and pink and white sneakers on, I stepped into the bathroom quickly fixed my hair and applied lotion to my hands.

I nervously descended the stairs to the living/dining to discover Harry was already in the garage. I headed down to the garage and joined Harry in the car.

Harry turned to me with a big smile and said: “Wow Casey. You look great. I love your outfit. Let’s go shopping.”

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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.