Sent Away Ch. 06

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Harry takes his Sissy panty shopping.
2.4k words
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Part 6 of the 11 part series

Updated 06/11/2023
Created 03/10/2022
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This is the sixth chapter of a multi-chapter story of a young man being turned into a crossdressing sissy slut.

When Harry said, "Let's go get you some panties boi." I felt an unfamiliar warmth of happiness wash over me. Smiling coyly I shyly glanced from Harry's stare to his deflating cock in my hand and licking my lips sighed contentedly.

Harry's hand slipped from my hair to lightly stroke my cheek and my eyes fluttered as I pressed my face against it. In a placid daze I barely comprehended when Harry announced, "Showers first, then I'm taking my newest little Sissy shopping."

The next thing I knew Harry was leading me to the bathroom where I allowed him to strip me naked while he gently caressed my body. Humming happily Harry surprised me by removing my cock cage before guiding me under the showers pulsating stream of hot water. The big man washed me from head to toes with great care and tenderness. I felt like I was melting beneath his large firm hands as they lathered me up with soap before stroking away the suds.

Harry's attention turned to my boihood and ass, as he massaged me my cock sprang to attention. Harry's soapy hands and fingers kneaded, squeezed and caressed my cock and buttocks as I chewed on my lower lip and moaned wantonly. Harry's fingers danced lightly over my erection as I trembled and moaned in response. When his hand caressing my ass slipped between my cheeks and grazed over my anus I swooned. Harry's fingers clasped firmly over my cock to hold me up when my knees buckled as his soapy fingers pressed home against my anus. With Harry's fingers sliding into my body my cock erupted in his other hand as I groaned my pleasure.

Harry's fingers pumped against my anus causing my body to lurch and thrust my cock into his hand as he milked me dry. Once my body stopped responding to the stimulus of Harry's magical hands he released me to slump to tiles beneath him. I crouched there shivering with released tension and felt numb while Harry kept showering singing quietly to himself above me.

Limp I allowed Harry to pull me from the shower and dry me off before replacing my cock cage. Lifting my chin with a forefinger Harry smiled down at me arching an eyebrow dramatically while murmuring, "Be a good Sissy and go get dressed pretty like for Uncle Harry." I stared back at him uncertainly but his smile didn't change as he added, "Go on now boi, be the Sissy you know you want to be." With a firm shove Harry directed me out of the bathroom.

I hesitated in the hallway before scurrying to my room to get dressed. I had no idea what Harry would find 'pretty' so I settled for a turquoise t-shirt my mother had bought me years ago and a pair of jean cutoffs that were far too short. My ass cheeks hung out of them flamboyantly but Harry's loud demand of 'Hurry up!' told me I had no time to change them. Nervous and unsure I crept downstairs to find Harry dressed and ready to go. The man cast an appraising eye over my body but said nothing before heading out the door. I followed cautiously.

Harry held open the passenger door of his big car for me to get in, slamming it firmly shut behind me. I sat nervously wondering where he was taking me as he wound his way silently through traffic. Eventually he parked on the edge of the city center and got out. I was looking around for a recognizable landmark when Harry jerked my door open stepping back to let me get out. It the harsh glare of the unfamiliar street I suddenly felt exceedingly self conscious. Harry was cool and calm as his hand firmly gripped my elbow to lead me down the street.

He was pulling through the open door of a store before I could even determine what kind of store it was. After the bright heat of the street I was momentarily blinded and immediately shivering from the stores cold air-conditioning. Harry kept a firm grip on my elbow as he led me through the close musty smelling shop. We had to brush past clothes to get through to the counter of the haphazardly stocked shop. A harsh women's voice called out from the back somewhere, "Can I help you?"

Harry snorted with a half laugh, "I certainly hope so." Harry's hand squeezed my elbow as the woman bustled towards us but I wasn't sure whether it was comforting or a warning.

"Well, well, well," the woman huffed looking us over with keen eager eyes, "what can I do for you today...", she stammered, stumbling over how to address us. Harry smiled and despite his grip on my elbow I tried to hide behind him away from the woman's now penetrating look. Regaining her composure she addressed Harry a little more formerly, "Can I help you sir?"

Still beaming Harry assured her, "Yes I believe you can." Pulling me by the arm into full view of huffing older woman Harry humiliated me by announcing, "My young friend here requires some new delicates." When the clerk gave him an surprised, uncertain look Harry informed her casually, "The young man has recently begun showing a peculiar interest in his mothers underthings." The woman gasped dramatically in wide eyed shock as Harry continued conspiratorially taking great delight in embarrassing me, "And his poor dear mother is beside herself with shame."

While he tried not to show his pleasure too much Harry let the old harridan cast a scornful eye over me in my too short cutoffs and too small turquoise t-shirt before adding, "She thought she had tried everything until her friend suggested that perhaps public shaming might cure such sordid sissy behavior." Pursing her lips in obvious disdain the clerk looked far from impressed but nodded her head to indicate she probably agreed while Harry added hopefully, "His poor mother would be so grateful."

The old woman paused then after looking me over once more and offered half heartedly, "Well I suppose." Then looking around the dimly lit shop a wry smile creased her well rouged lips before she purred lewdly, "What ever did you have in mind sir."

Harry pounced enthusiastically assuring her in a grateful tone, "A selection of items you that think would be appropriate to these, uhm, peculiar circumstances." When she cast him a crafty cunning look Harry enthused, "Madame we are in your good hands."

Her eyes glittering with malice the old witch reached out to take my elbow from Harry. Digging her nails into my arm she chortled cruelly, "Come with me sweetie and let's get you sorted out." Flexing her nails into my flesh she then tugged me towards an overloaded rack of assorted women's underwear.

I flushed red with humiliation as she held a pair of sheer orange panties up to my waist while musing, "Do you know what size your young friend is sir?" Harry watching on with amused disinterest shook his head no, he was more interested in checking out the activities of the shops other clients. T'sk t'sking while rolling her eyes in mock weariness she quickly grabbed several different pairs of panties before announcing too loudly, "Well I suppose we'll have to try some on then."

With a fist full of various panties the old woman gripped my elbow hard enough for me to yelp in pain before dragging me to the back of the shop. Unceremoniously she propelled me into a curtained change nook stating curtly, "Drop those shorts Sissy." When she didn't close the curtain or look away I hesitated. The old witch gave me an appraising look before smiling evilly and hissing, "Now!"

Stung, I obeyed without worrying that I wasn't wearing any underwear and realizing too late that she was about to see my cock cage. Expecting her to be shocked I was mystified when I dared to look up to see her standing there with an evil glint in her eye and a malicious smile glued to her lips. Without a word the woman ogling me held out the pair of orange panties for me to take and try on. Gingerly and withering with humiliation I complied.

Once I pulled them up to my waist the old harridan was all over me. Crowding into the dressing room nook and squatting on her heels she began tugging and pulling the panties this way and that, musing to herself, "Yes yes, these do seem to fit but I suspect that we are going to require more space here." On 'here' the witch grabbed my caged cock through the filmy panty material to tug and pull on it objectively.

Rising she kept her grip on my cock and was standing so close that her heavy bosom pressed into my body as she breathed huskily, "Pity about your peculiar interests Sissy." When I could only stare at her uncertain and slightly terrified she tugged on my caged cock continuing hoarsely, "It feels like you would make a very acceptable boy toy." She peered deeply into my eyes with a knowing penetrating look that made my knees weaken and my cock stir in her warm hand.

With a flick of her wrist the moment was over and she was demanding, "Get those off and try on these." She was holding out a pair of red briefs with black lace. I had never seen underwear like them let alone tried anything as sexually sultry on. My cock throbbed as I pulled on and off various pairs of exotic women's panties as the shop owner hummed and hawed over how they looked.

Eventually she settled on a pair of looser pale blue briefs with rows of ruffles running across the front. Physically turning me from side to side she purred, "Yes, these will do nicely I think." Abruptly she had me by the elbow again and to my horror was leading me mortified back out into her store.

"Well, here we are," she sang out airily, seeming not to care who heard. As I died inside she dragged me before Harry who was chatting casually to a middle aged very well dressed woman. My head sank between my shoulders with shame as the two stopped their conversation to look me over.

Harry smirked, enjoying my degradation while the lady beside him appraised me in my ruffled light blue panties as if it was something she witnessed everyday. While the store owner hummed and dug her nails into my flesh, Harry continued to quietly smirk and the new lady gushed, "Oh isn't that sweet." The nails dug in deeper, Harry couldn't help snorting his amusement while I wished for the floor to open up and swallow me, while the lady continued merrily, "Surely pink is a much appropriate color for a Sissy to wear."

Harry chuckled, while the old harridan murmured almost contritely in agreement, "Why yes, yes of course. Give me a moment to correct that for you."

After retrieving the suggested panties from the rack the shopkeeper snatched at my elbow peevishly and started hauling me back to the change nook when the lady's voice stopped her cold, "Oh surely darling, that won't be necessary." The older woman turned and though obviously put out she took a deep breath waiting for the younger lady to clarify. With her hand now resting on Harry's arm she sighed with mild consternation, "Surely there's no harm in having a Sissy change right here."

Pursing her lips and trying to contain her emotions the older woman responded with thinly disguised irritation, "Well no, no not at all dear." With a huff she then turned on me, thrusting the new pair of panties at me and snapping, "Quickly now. Out of those and into these."

Over the commotion of trying to change from one pair of panties to the other as quickly and modestly as possible I heard first a gasp and then the squealed laughter as three young women shopping in another aisle caught on to what was happening. Their laughter seemed to annoy the shop owner even more and digging her nails painfully into my arm she hissed, "Quicker."

Flustered and on the verge of tears I finally pulled the ruffled pink panties up to my waist to the sounds of the young women's loudly whispered conjecture as to what it was that they couldn't believe they were watching. The shop owner held me by the elbow, her angry stance all but demanding that the lady leaning on Harry's arm hurry up and speak. While the girls tittered the lady mulled me over before posing to no one in particular, "I think maybe peach."

I thought the old witch was going to rip my arm off. Stomping off the older woman summoned the control to fetch a pair of peach panties, then get me into them. All the while the lady hummed pleasantly and the girls shrieked with renewed appalled hilarity and Harry slipped his arm around the lady's waist pronouncing officiously, "Peach it is."

I feared the old store owner was going to explode when the three young women fled shrieking from her shop. Turning on me she hissed, "Go get your shorts on."

By the time I had gone to the back, put on my cutoffs and returned, Harry had already settled the purchase and he was sauntering off with the lady hanging onto his elbow. When I paused the shopkeeper hissed, "Get out!" A quick glance at her tip lipped impervious glare told me not to tarry as I scurried after Harry and this new lady.

They ignored me, just expecting me to be following them. It wasn't until we were halfway back to the car that a couple's laughter told me that my cutoffs were too brief for the panties Harry had just bought me. I realized that the peach panty was peeking out from beneath the edges of my cutoffs every time I took a step. Flushing furiously red I tried to pull them down but it was futile and worse, the couple were now pointing as they doubled over with amusement. Harry and his lady friend sauntered on as if nothing was amiss.

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