Cassie’s College Journey — Part 15

Teddy Bear

Cassie Smith
5 min readMar 15, 2024

Please note, this is Part 15 of a series. I hope you enjoyed reading Parts 1–14.

Back in my tastefully pink and grey bedroom, legs still quivering slightly, heart pounding and pleasure neurons skittering around my brain, I took off my dark-pink high-heel suede ankle boots with cute light-pink fluffy fake fur trim and sat on my plush China-pink comforter, acutely aware of the damp spot in the crotch of my sunshine-yellow satin bikini panties, where my small tucked clitty had been leaking all evening.

Without the dominant masculine presence of Harry, his manly scent fading away, my small clitty started deliciously swelling and urgently pleading for attention.

This thrill of constant arousal I’d experienced all evening, provocatively putting my silky-smooth legs on display, nude-coloured nylon stockings coolly and tenderly nestling against my soft skin, the decorative elastic lace tops snugly embracing my upper thighs, a delightful constant reminder of their presence, powerless and vulnerable as the cool autumn breeze explored up under my rose-pink tweed flared miniskirt, sensually teasing and caressing the naked skin between my silky stockings and my satin panty-clad derriere, while the hem of my miniskirt playfully swished and swayed with the motion of my hips, accentuated by wearing high-heels.

Overwhelmed with the sensory overload of the evening catching up, laying back against the orchid-pink pillows, I ran my bubble-gum pink manicured hands gently against my soft and smooth stocking-encased legs with the intent to carefully pull them off, sliding them down, patiently avoiding snagging them with my nails. Instead, I found myself, basking in the electrical tingly sensations they created as I rubbed them together, and mesmerised by the visual imagery of my slender manicured hands exploring my long and deliciously luscious legs.

Seemingly of their own accord, my dainty manicured hands continued up my smooth thighs, slowly and tantalisingly lifting the hem of my rose-pink miniskirt, revealing my lacy stocking tops, the soft silky bare skin above, and finally my sunshine-yellow satin bikini panties, the ivory-white lacy front smooth and flat and feminine, my privates pushed up inside my pelvis, my swelling clitty tucked safely back in the crotch of my panties against my silky-smooth perineum, leaking insistently, the damp spot growing in size.

In a trance, a warm current of dopamine flowing through my brain, I nestled back against my soft pillows and slowly spread my silky nylon-clad legs wide apart, pleasure neurons excitedly dancing, my manicured fingers gently teasing and caressing my smooth inner thighs and satin panties, electrical tingly sparks every point of contact.

I replayed the evening, the images and feelings and sensations, remembering the hungry animalistic stares from men and jealous looks from women, remembering Harry protectively holding my hand and holding my chair and opening the door and holding me in his arms as he guided me up the stairs to our townhouse, butterflies swarming in my tummy.

My manicured slender hands moved to my swollen clitty tucked tight against my smooth perineum, bubble-gum pink nails contrasting against my sunshine-yellow panties with frilly ivory-white lace. Sensitive fingertips savouring the smooth and silky satin and the pleasantly scratchy lace, pleasure neurons happily swimming in a dopamine tide, tingly feelings up and down my nylon-encased legs.

My heart beating faster and breath quickening, my padded breasts a comforting feminine weight on my chest, my sunshine-yellow bra straps constricting, a reminder of their presence with every breath.

I closed my eyes and became lost in the sensual sensations of my feminine clothing, my clitty straining against the crotch of my panties, deliciously rubbing against my smooth perineum, my privates tucked up inside my body. My manicured fingers gently rubbing and pinching and pressing my swollen clitty against my perineum.

Suddenly I felt a warm glowing feeling in my tummy spreading outwards to the rest of my body, my legs started quivering as my manicured fingers instinctively increased their attention, pinching and rubbing my swollen clitty tucked between my legs, and a bright light exploded in my brain and my clitty discharged a creamy in my panties while I whimpered and moaned and gasped.

Catching my breath, brain spinning, I mechanically undressed and cleaned up, removing my Bambi eyelashes and makeup, Cassie reverting to Casey in the mirror before my eyes. I left on my bubble-gum pink nails for coffee with Heather tomorrow, then stepped into the shower where the hot water cascaded over my smooth silky body while my brain ran in directionless circles.

Post shower, I focused on applying lotion and grooming my hair, pulling on my silky coral-peach robe, clitty drained and listless and went to my dresser for fresh panties and a tee to sleep in.

I laid out the Persian-pink yoga outfit for tomorrow. Without conscious thought, my bubble-gum pink manicured hands opened the pretty lingerie drawer, and I was drawn to a fluffy and frilly babydoll nightgown dripping with lace and little pink bows.

Pulse quickening, I gazed in wonder at this ultra-feminine lacy pink-sherbet babydoll nightie, spaghetti straps held delicately in my bubble-gum pink manicured hands, trembling as the pleasure neurons danced happily and dopamine flooded my senses. The frilly babydoll had a matching thong, which I quickly pulled on, confining my clitty in the front before it could achieve a stiffie.

The lacy pink-sherbet babydoll floated like gossamer down my lean smooth body, electrical tingles every point it touched. My brain eagerly welcomed the stimulation that overwhelmed my senses, unable to process the sensations and feelings.

I saw a fluffy misty-grey teddy bear and brought him to bed, snuggling under the orchid-pink sheets. Wrapping my thin arms around him, holding him close to my narrow chest, spooning and slowly stroking his fluffy fur. Feeling the snug embrace of the lacy bodice of the pink-sherbet babydoll, the frilly lace tickling and flirting with my silky skin, my small clitty imprisoned in the the matching thong, the thin strip of silky fabric squeezed between my derrière cheeks and pleasantly rubbing my smooth perineum.

Wondering what tomorrow would bring, I drifted off to sleep.

College Journey Part 16 Coming Soon . . .

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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.