Cassie’s College Journey — Part 14
Pizza
Please note, this is Part 14 of a series. I hope you enjoyed reading Parts 1–13.
I woke up to Harry gently rubbing a firm masculine hand on my narrow shoulders. Opening my eyes gingerly, I felt the aftermath of the party last night and whimpered quietly.
Harry smiled reassuringly, gently pulling my dark-blonde hair off my cheeks, and softly said: “Wake up sleepyhead. I’m going downstairs to fix breakfast. Why don’t you take a shower and change to something comfortable.”
After Harry left, I slowly crawled out from under my orchid-pink sheets and headed to the shower. Locating some aspirin, I carefully removed my pleated plaid miniskirt, sweatshirt, panties and bra from the party last night. My little clitty made a half-hearted attempt to achieve a stiffie, but my headache prevented progress.
Removing my Bambi eyelashes and makeup, I stepped into a long hot shower. My brain a bit fuzzy, I neglected to take off my bubble-gum pink press-on nails, so had to be careful shampooing my dark-blonde hair and grooming myself.
Post shower, feeling much better, I dried myself off with a fluffy carnation-pink towel, applied lotion all over, my now soft and smooth body, pulled on my comfy coral-peach silky robe and proceeded to dry my dark-blonde hair and brush it, pulling it into a high ponytail with a lemon-yellow scrunchy.
Memories of last night flickered like snapshots, images and sensations and feelings intermingled. Looking at myself in the mirror with makeup on my face and seeing Cassie, a beautiful girl looking back. Harry’s initial reaction when he saw Cassie in my baby-pink and cornflower-blue plaid pleated miniskirt with snow-white frilly lace hem, and the butterflies in my tummy responding to his reaction. The cool caress of an October breeze playfully flirting under my flaring miniskirt, and the tingly feelings as my silky nylon-encased smooth legs delightfully rubbed against each other as I walked. The sound of my bubble-gum pink heels click-clacking on the marble floor of the expensive hotel lobby. The hungry looks from men all evening, and Harry protectively pulling me closer with his stong masculine arms. Feeling vulnerable as I sat in Harry’s lap with my pearl-white satin bikini panty-clad derriere directly rubbing the course fabric of his trousers, feeling his hard penis urgently pressing up against me.
Butterflies and tingly electrical jolts, my heart beating rapidly, I went to my lingerie drawer, my thoughts like a hamster on a wheel.
I told myself that I dressed up last night to support Harry, and he clearly had been happy with my outfit and makeup. If anyone thought that I wasn’t a girl, they never showed their suspicions.
And I enjoyed myself. I enjoyed feeling pretty and wearing beautiful clothes. I enjoyed the attention from both men and women, something previously never experienced in my entire life. There was even a part of me that enjoyed my long, silky-smooth legs being on display and, as the girls table discussed, the naughty thrill that someone could catch a glimpse of my pearl-white satin bikini panties with all the frothy lace.
Standing in front of my panty drawer, my pleasure neurons bouncing merrily, and my stiffie tenting my silky coral-peach robe, I chose a beautiful pair of sunshine-yellow satin bikini panties with ivory-white frilly lace. Laying back on my orchid-pink smooth sheets, I attempted to tuck my small clitty securely inside, but it was proving difficult.
Laying on my back, knees spread wide, my silky sunshine-yellow panties snugly teasing my perineum and privates, my soft slender hands with bubble-gum pink manicured nails holding my stiffie, I instinctively started slowly stroking, the dopamine washing over me and delicious tingly feelings all over, especially the locations where my silky coral-peach robe playfully flirted with my soft skin and my long bubble-gum pink nails delicately teased my satin-clad perineum.
Again, images and feelings and memories of last night flickered in my brain. Jealous thoughts of Heather’s seductive French Maid costume, especially the frothy layers of frilly petticoats, wondering how the scratchy tulle fabric would feel against my silky legs encased in seamed stockings. The hungry looks from men. Harry’s hard cock pressed against my tender pearl-white satin bikini panty-clad derriere. Harry effortlessly carrying me up the stairs in his strong, muscular arms while my slender, frail arms were wrapped around his masculine neck, and him gently kissing my forehead as he tucked me into bed.
Suddenly my thoughts shifted, and I imagined Harry kissing me on my bubble-gum pink lips, his strong manly callused hands gently exploring my silky smooth legs, while my soft bubble-gum pink manicured hands were stroking Harry’s manhood, feeling the magnitude of his girth, and stroking the length of his hard masculine cock. Without warning, the pleasure neurons exploded, as did my twitching clitty and I caught the creamies in tissues, moaning and gasping and whimpering.
I melted into the bed for a few minutes, legs trembling, panting to catch my breath, my thoughts a scattered mess. I carefully cleaned up and tucked my now soft and limp clitty in my sunshine-yellow silky bikini panties and resumed dressing, brain trying to process what just happened.
I next found the pastel-yellow crop top tee and pulled it on, followed by my dark-grey sweatpants and my canary-yellow yoga lightweight jacket.
One final look in the mirror, brain still wondering where these thoughts came from, and I slowly went down the stairs to Harry and his promise of breakfast.
Harry smiled and held l my chair for me, butterflies flitting about as I submissively sat down. Harry then poured coffee and served me a plate of eggs, sunny side up, bacon, hash browns, toast, and a half grapefruit.
Smiling, Harry said: “Good morning Casey. Are you feeling ok? I think Cassie had a touch too many cocktails last night.”
I blushed deeply, unsure what to say.
Harry continued, smiling and told me that he was he hoped I had a good time last night, and he was so grateful for my attending as his “+1” and everyone loved my costume, a lot of people had commented on it.
Pleasure neurons bounced happily and the tummy butterflies swooped in giddy circles, me blushing deeper and happy that Harry was pleased with me.
Harry continued, saying we probably both need to take it easy today and asked if was I up for a bit of Mad Men binge watching. I smiled and said that sounded good to me.
With that, we started eating and Harry was very talkative and clearly jubilant over the party. He explained who the different people were that we met at the party and that Kristie had introduced him to even more while Heather and I had been chatting. He was very excited that these people wanted to hear more about his proposal, which was why he stayed longer, and Kristie came back to hang out with us girls.
I felt tingly and happy for Harry that the party went so well for him. We finished eating and Harry insisted he clean up and I go and relax on the couch.
I took my coffee and nestled in my accustomed spot on the couch, sitting side-saddle, Harry shortly joined in his masculine leather chair, after starting a fire in the wood stove, and we watched Mad Men, and chatted, Harry still exuberant over the party, and I snug and warm and comfy in my girly clothes, soft and limp clitty complacently tucked into my pretty sunshine-yellow silky bikini panties, dopamine lapping and soaking up Harry’s approval and happiness, and and I drifted off to sleep.
I woke, TV off, fire in the wood stove practically reduced to embers, snuggled under a dark-blue soft blanket, evidently Harry had covered me when I fell asleep. Stretching, I shyly went to the dining area and Harry was busy on his laptop. Seeing me, he stopped, smiled and asked if I had a good nap.
I blushed and tried to apologise, but Harry smiled that warm friendly smile and told me that he knew I went through a lot of effort to become Cassie yesterday, and to be Cassie for the Halloween party, and he really appreciated and understood that I must have been exhausted today.
The little butterflies in my tummy took flight and swarmed around, while I blushed even more and didn’t know how to respond.
My phone dinged with a text message, which provided a much-needed distraction. It was a message from Heather, she wanted to meet me for coffee tomorrow afternoon.
I was torn, I really enjoyed talking to Heather, and she was a lot of fun, and would like to get to know her better, but she only knew me as Cassie, and she was Harry’s co-worker.
Sensing my distress, Harry gently asked me if everything was OK, so I told him about the text message and Heather and coffee and my concerns.
Harry smiled with amusement and declared this deserved a glass of wine and told me to wait, as he jumped up and headed to the kitchen area. He quickly returned with a glass of white wine for each of us and a little cutting board with some cheese and fruit, which he proceeded to serve.
We talked and sipped wine and snacked. Harry told me he had no concerns with me going for coffee and building a connection with Heather, for him there was zero conflict of interest, in fact, he trusted Heather, which is why he also arranged for her to receive an invitation to the party. The real question he posed, was did I want to meet Heather as Cassie, whom she met last night, or Casey, whom she hadn’t met.
We talked some more, and I couldn’t reach a decision. Harry suggested I write back and set a time to meet Heather tomorrow. Tonight, we could grab pizza, and I could be Cassie, he pointed to my bubble-gum pink manicured fingernails I had neglected to remove, and I could see how comfortable I felt. If I didn’t feel comfortable, I could always meet Heather as Casey, and explain the situation, or cancel.
Harry made logical points that were difficult to counter. Did I secretly want to experience Cassie again, to indulge in wearing the sensual girly clothes, and feel pretty, and have people notice me. Harry must have sensed I was on the fence. He grasped my bubble-gum pink manicured dainty hands with his strong manly ones, looked me with his dark-blue eyes and firmly told me, in his deep husky voice, he really wanted to take Cassie out for pizza, to thank her for going to the party last night, now let’s go upstairs and get changed.
The butterflies burst into flight while the pleasure neurons skittered about, and tingly electrical shivers ran up and down my body. How could I say no, so I nodded submissively as Harry gently pulled me to my feet, placed a masculine hand in the small of my back, and firmly guided me towards the stairs.
Back in my tastefully pink and grey bedroom, I took off my canary-yellow lightweight yoga jacket, clad now in my dark-grey sweatpants and pastel-yellow crop top tee, clitty pleasantly swelling, but safely tucked in my beautiful silky sunshine-yellow bikini panties, and went to my closet to figure out an outfit.
The myriad of options was fairly overwhelming, but I was drawn to back to the ivory-white fluffy turtleneck sweater. I had fond memories of Harry’s reaction to this the first time I wore girly clothes, my tummy butterflies fluttering a bit as I remembered his reaction.
I decided that skin-tight jeans were too safe a choice, if I truly wanted to experience Cassie again, so looked at skirt options. I located a rose-pink tweed flared skirt that I thought would look really cute. On the shoe shelves, I saw some dark-pink high-heel suede ankle boots with cute light-pink fluffy fake fur trim. I could see the outfit coming together, and it would pair with the dark-pink coat I had been wearing, also as a bonus, my bubble-gum pink manicured nails would coordinate as well. I felt tingly feelings in lots of wonderful places, the happy neurons bouncing excitedly, and warm dopamine flooded my brain.
Outfit chosen, I took off my dark-grey sweatpants and pastel-yellow crop tee and donned my coral-peach silky robe and took a seat on my dark-pink makeup counter stool, the silky coral-peach robe riding up and my sunshine-yellow satin bikini panty-clad derriere delightfully brushing against the soft padding of the stool. I assessed the myriad of make-up options available, pulled out my fuchsia-pink iPad and did some internet searching for inspiration for both make-up and my dark-blonde hair.
After a little bit of searching, I found some inspiring photos and started in with my makeup brushes and products. I quickly got in the “art zone” and suddenly, I was looking in the mirror at Cassie, looking back at me.
My dark-blonde hair was pulled back into a loose low ponytail held with a cute flamingo-pink barrette, my dark-brown eyes accented with denim-blue eye shadow with shimmering highlights, cat-eye eyeliner punctuating charcoal-black curled eyelashes, nude-pink blush and matte rose-pink lipstick. Pleasure neurons bouncing happily and little tingly feelings, I moved to get dressed.
I searched in my bra drawer and located a lacy sunshine-yellow bra that matched my bikini panties. I pulled it on and reached behind my back to hook. Adjusting the shoulder straps, and filling the cups with breast forms, I felt tingly feelings flitting across my body. Next, I sat on the China-pink bed and pulled on nude-coloured silky nylon thigh-high stockings with decorative elastic lace. The feeling of the cool silky stockings nestling tenderly against the skin on my smooth soft legs was indescribable, the pleasure neurons bouncing excitedly as the dopamine crashed over me and my safely tucked little clitty swelled and strained inside my sunshine-yellow satin bikini panties.
Next, I pulled on the rose-pink tweed flared miniskirt, shorter than I anticipated, just barely covering the lacy elastic tops of my silky nude stockings, and the ivory-white fluffy turtleneck sweater, finalizing my girly outfit with the dark-pink high heel suede ankle boots with cute light-pink fluffy fake fur trim.
Checking myself in my mirror, I was ecstatic with how I looked and secretly wondered what Harry’s reaction would be, butterflies flittering in my tummy with these thoughts.
Grabbing my dark-pink fall coat, I carefully took the stairs down to the living/dining floor, still a little wobbly in high heels, but gaining confidence, my nylon-clad smooth legs rubbing delightfully against each other, feeling the snug and comforting lacy elastic tops holding them up, electrical tingly feelings skittering with the pleasure neurons.
Harry saw me coming down the stairs and smiled broadly. He reached out and took my bubble-gum pink manicured hand and with a playful grin, bowed slightly and said he was happy to meet Cassie “again”, and take her out for dinner. The butterflies took flight and swarmed in my tummy while the dopamine crashed over me. Blushing, I smiled and thanked him for his compliment. He continued to hold my hand in his warm, strong masculine one and led me down the stairs to the waiting Uber.
Harry opened and held the Uber door for me. I tried to gracefully climb inside, reasonably confident I did not flash my silky sunshine-yellow bikini panties. The lacy tops of my silky nylons were a different story, Harry noticed as the hem of my rose-pink tweed flared skirt rode up and exposed them, his eyes glued to my silky nylon-encased legs and smiled broadly.
Flustered, embarrassed, and the butterflies swooping in my tummy, I modesty arranged my skirt, making certain my lacy stocking tops were covered, desperately remembering to keep my knees together, feeling vulnerable as the cool smooth leather of the car seat caressed my panty-clad derriere.
Harry sat next to me and took one of my small, manicured hands and engulfed it in his large, strong manly ones. He leaned towards me and whispered in my ear, feeling his hot breath tickling the side of my smooth neck, and soothingly told me that I looked amazing, and he was proud to take Cassie out on a date, emphasising his words by firmly squeezing my slender manicured soft hand.
The butterflies took flight and dopamine crashed over me, and I felt tingly electrical sparks on my silky nylon-encased leg where Harry’s heavy hand was resting. For some reason, my small, soft, limp clitty, safely tucked into my silky sunshine-yellow panties also tingled and started embarrassingly leaking, a small damp spot in the crotch of my panties.
We arrived at the pizza restaurant and Harry gallantly opened the car door for me and offered a strong masculine hand, helping me exit the vehicle.
Harry continued to possessively hold my delicate manicured hand as we walked to the restaurant, the sound of my high-heels clicking on the pavement, a brisk, cool breeze exploring up under my rose-pink tweed flared skirt, flirting with my silky nylon stocking-encased legs, the cool air delightfully caressing my smooth bare upper thighs above my stocking tops and my silky sunshine-yellow bikini panties.
The sensual sensations made me realise how much of my body was on display, making me feel vulnerable. I instinctively reached over and grabbed Harry’s strong upper arm with my other frail manicured hand, pulling myself closer to his strong masculine presence, heart pounding in my chest, while the pleasure neurons danced happily and the tingly feelings coursing up and down my legs.
For some reason, I was terrified. More nervous than last evening at Harry’s work party. Last evening had been an overwhelming experience, I had spent the entire day worrying and planning and prepping and dressing and by the time we arrived at the party, I was a bit numb and focused on the immediate, talking with Heather and Kristie navigating the party. Exposure at the party could have been laughed away as a joke or dare. Tonight was different. Harry was showing me off as his date for the evening, no joke, no dare. The butterflies swarmed in my tummy and my safely tucked soft limp clitty started leaking again in my panties.
The waiter escorted us to our table, my hips swaying seductively while my rose-pink tweed flared skirt fluttered against my silky nylon-clad legs. He took my dark-pink coat and held the chair for me as I gracefully sat, crossing my smooth nylon-encased legs like a girl might do, and instinctively smoothed the hem of my skirt, immediately feeling the smooth, cool touch of the chair’s wooden seat directly against my sunshine-yellow satin bikini panty-clad derriere. Glancing back at the waiter, I saw his eyes transfixed on my stocking-encased legs, causing tingly feelings in delicious places. I nervously looked over to Harry, and saw him grinning at the waiter’s reaction while he looked at me and winked.
Harry ordered a bottle of red wine, and we each ordered a small Neapolitan style sour-dough pizza and a salad. The wine quickly arrived, and we toasted and started talking as we waited for the food to arrive, Harry cheerfully guiding the conversation. I gathered my thoughts and quietly asked Harry what if someone figures it out, about me.
Harry paused, reached across the table, and possessively engulfed both my slender manicured hands into his hefty masculine ones and responded: “Cassie, you look truly amazing. Every man in the restaurant watched you gracefully walked to our table. The waiter couldn’t take his eyes off you. The women were also watching, annoyed and irritated at their dates. Besides, if one person, or several people figure it out, I really don’t care. I am confident of who I am as a person, and don’t care what other people think. You look stunning, and I am proud to have you with me tonight as my date.”
Blushing, I nodded, butterflies swooping with glee in my tummy as a dopamine wave crashed over me, soft, limp clitty started leaking again, safely tucked in my satin sunshine-yellow bikini panties. Our pizzas and salads arrived, and we proceeded to enjoy our food and wine. I relaxed and enjoyed the ambience and our meal and our conversation and somehow felt comfortable being with Harry dressed all girly as his date, dopamine warmly washing over me, and the little pleasure neurons danced happily.
Midway through dinner, I suddenly realised this was the happiest I had felt in a very long time. I felt at peace with myself and with life. I enjoyed my classes and teachers and co-students and could see achieving my degree next spring. I felt grateful for Harry’s hospitality and support and enjoyed not only sharing his townhouse, but also being with Harry and spending time with him and talking and sharing moments like this. A part of me enjoyed dressing in the girly clothes, the fabrics, the colours, the makeup, and the options. I had never been noticed in life, and now felt very much noticed and on display, which I would have to admit, felt really, really good.
Dinner complete, our bellies full and the wine long gone, we had a quick espresso and Harry called an Uber. Like a gentleman, Harry assisted with my chair and my dark-pink autumn coat. I instinctively reached for his solid masculine hand with my slender manicured one as we weaved our way through the tables and out of the restaurant, I imagined the hungry eyes of men and jealous eyes of women, while my hips swayed in time with the click-clacking of my high-heels, and my soft, limp clitty tucked and leaked in my silky sunshine-yellow bikini panties. Outside the restaurant, the weather colder, Harry felt me shivering and wrapped his strong muscular arms around my waist, pulling me close to his chest. My heart thumping in my chest, the tummy butterflies burst into flight and tingly electrical feelings flitted all over my body.
The Uber ride home was uneventful, the cold leather seat fabric caressing my sunshine-yellow bikini panty-clad derriere, as I again remembered to keep my knees together, while I held one of Harry’s strong masculine hands in my lap with both of my slender bubble-gum pink manicured hands, and leaned and snuggled against Harry for warmth.
Once home, Harry wrapped one muscular arm around my narrow waist and guided me into the townhouse and up both flights of stairs, only releasing me at my bedroom door. Smiling tenderly, Harry gently grabbed my narrow shoulders with his strong masculine hands and told me in his deep, velvety voice that he had a wonderful evening and hoped I did as well. Firmly pulling me closer to him, looking up at him, despite my high-heels, my eyes locked and mesmerized with his dark-blue ones, butterflies swarming in my tummy and happy neurons skittering.
Harry gently leaned forward and brushed his masculine, yet soft lips against my forehead and leaned close to my ear and whispered: “Goodnight Cassie. Sweet dreams.”
Suddenly releasing me, my knees weak and my clitty leaking into my silky panties, I stumbled into my tastefully pink and grey bedroom.
