Internet Meeting

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We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear — discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures.

We chatted online. He claimed my emails made so hot he often came in his panties while reading them. I was thrilled. How I had secretly longed for the acceptance of another like minded person. His excitement was infectious.

We exchanged fantasies and it wasn’t long before I realized that Charles was directing the flow and subject matter. It was an exciting discovery. My adrenalin surged the first time he referred to me directly as a “Princess”. When he suggested that we each dress in our sissy best before commencing any emailing I readily agreed. From then he started every email with, “What are you wearing Princess?” That Charles seemed so pleased with my descriptions of my outfits thrilled me.

Charles inquired discretely about my life by asking innocent questions about my childhood, my exploration into the world of cross-dressing and sex. He was so understanding and accepting. His emails were full of praise and encouragement that eased my many fears and misgivings about leading my secret life of a cross-dressor. When he changed his query to, “What are you wearing for Me Princess?”, my heart fluttered and my body was suffused with??. I sat still staring at the computer screen, visibly trembling as I let the excitement of Charles ‘s words surge through me.

Then he asked for a pic. Nervously I complied sending him a self portrait of my panty clad bottom with any identifying detail blurred out. I drove myself to distraction checking to see if he had responded terrified that he would find me so unappealing that he would end our contact.

It was with a trembling finger that I opened his response. Relief washed over me as I read his message. He was, he claimed, awed by the loveliness of my pantied bottom. My dick tingled beneath my skirt as he described in detail how hot I made him. How hard he had cum when he masturbated while fantasying about using my pantied bottom for his pleasure.

My panties tented out embarrassingly my cock was so hard. Rereading his email I gently stroked myself to a numbing explosive orgasm filling my shiny panties with hot sticky cum. Panting I quickly sent Charles an almost incomprehensible message about how hot he had made me and how wonderful my orgasm had been.

He promptly replied. He wanted to see my cum filled panties. Chewing on my lip nervously but caught up in the excitement of the moment I complied. It was a fuzzy effort as I had to hold my skirt and slip up while pulling the front of my panty away so I could capture an image of my cum filled panties for Charles . I rushed to send it to him then sat back to bask in my post orgasmic fugue.

Dreamily I opened his response only slightly startled by a close up picture of a fully erect shiny cock protruding from a delightful pair of ruffled panties the tip slick with precum. “Like a taste?” Was the caption beneath it.

Drawing in deep calming breathes I licked my lips wetly and typed, “Would luv a taste!”

Charles insisted on a new pic with every message. I was hooked.

Charles was fabulous. He made me feel deliciously sexy sitting before my computer in a slinky dress, sheer nylons and a lacy panty. Charles added url links to various websites he hoped I would find interesting, always keenly showing interest in my opinions and thoughts about them. Soon I was routinely visiting websites regarding all things a cross-dressing sissy Princess should know.

Through these sites Charles introduced me to proper sexual hygiene, directions and hints on sexual pleasure, training and transforming ones body to better improve your looks, your performance, my behaviour. There were sites dedicated to the latest in clothing and implements where Charles would indicate items he thought I would look special in or things that I would enjoy. I discreetly began ordering İstanbul Escort various items – panties first, then sex toys and outfits, making my daily visits to the mailbox a thrill of anticipation. I couldn’t wait for something to arrive so I could share it with Charles .

Soon I was practicing proper anal hygiene and hair removal as per instructions and tips I garnered from the sites I was visiting regularly. Charles was full of encouragement and approval after viewing my now daily emailed pic’s of my latest acquisition or body transformation. He inquired after the most intimate details of my grooming often making helpful comments and kindly suggestions.

Other sites Charles sent me links to were simply and fantastically sex. Most were for cross-dressing but Charles ‘s interests didn’t stop there. Cuckolding, Bukakke, Domination, Bondage, Spanking! Charles lead me down into the dark exciting realms of what polite society would refer to sexual perversion. It left me trembling with cum filled panties while I distractedly typed mostly incoherent descriptions of my thoughts to Charles .

The discovery my first package in my mailbox left me weak kneed and twitching with excitement. Chewing my lip with the certainty that some one would know what the nondescript package contained I rushed back to my apartment desperate to discover what delightfully taboo item I had received. My heart thumped in my chest as I nervously dressed appropriately before delving into the package. Gasping with delight I beheld the Anal Trainer Kit. A collection of progressively larger anal plugs and lube. I could barely contain myself as I tore into the package. The excitement of taking a step further into the world of sexual deviation was driving me to distraction.

It was all I could do to wash the items as instructed, my trembling hands making a mess as I slopped soapy water everywhere. Hurriedly I prepared my body for its first ever insertion. Clumsily I set up my camera to capture the event for Charles before pulling my ruffled panties down and hiking up my short skirt to expose my soft, creamy skinned bottom. Using a mirror I directed the plug as best as I could towards my virgin Princess pussy awed at how hard my sissy clit was straining against my gurlie pink panties.

I gasped when the cold wetness of the lube coated beginners plug made contact with my sissy Princess hole. Panting with need and anticipation I pushed the slick tapered plug into my waiting gurlie-boi-pussy willing my body to relax and accept the intrusion. My body convulsed as spasms of mild pain then extreme pleasure emanated from my Princess bottom when the plug inevitably slipped in. I emitted a long “Aaaah,” as my gurlie-boi pussy sucked the plug deeper inside me.

Oh what a sensation, I swooned as the auto flash on the camera highlighted in the mirror the plug buried deep inside me. Trembling I slipped my ruffled panty back into place pulling it up tightly to keep the plug buried deeply in place. My sissy Princess pussy clinched in pulsing spasms as I learned to accept plug.

Chewing my lip with excitement I retrieved the photographic evidence of my adventure to attach to an email to C. It was terribly exciting to look at the series of pictures of my fingers pushing my first ever plug inside my puckered Princess hole. I could only hope that Charles would be equally excited.

And he was. Charles’ responding email was infused with positive energy as his professed awe of my wickedness. He wished that he could have been there personally to be a part of such an exciting moment for me. I absolutely gushed with pleasure. My sissy clit was oozing pre-cum soaking the front of my panties. Giggling with excitement I professed that the only thing that could have made the experience better would to have been able to do in front of him.

The plug in my Princess pussy had me so wound up and hot that by the time he suggested a discrete meeting I was beside myself with distraction. We agreed on a public location where we could check each other out and safely retreat if anything wasn’t to our liking. He told me he would wear panties Escort Bayan for me and bubbling with anticipation I told Charles that I would too. “And your friend?” Charles inquired archly. Swallowing hard my bottom clinching possessively about my “friend” I responded most definitely YES!

As I promised I wore panties and my friend to our rendezvous. Sheer powder blue briefs beneath my loose fitting trousers held my friend firmly in place as walked nervously to the meeting point. Charles said he would be wearing a brown leather jacket and I was slightly dismayed that it seemed like so was everyone else. In my distracted state I was startled when a older man with a foreign lilt to his voice asked if he could join me. He smiled benignly at my confusion allowing me time to realize who he was.

Charles. I hadn’t known what to expect but this gently smiling older guy with a receding hair line of grey hair and a goatee wasn’t it. I watched him warily trying to decide what I should do as he claimed the seat opposite mine. Without putting me on the spot with questions Charles starting conversing in a soft murmur about the weather, the days news and sports. Seemingly perfectly at ease he spoke quietly settling my rattled nerves with the steady monotone. My bottom clinched reminding of what I had done in anticipation of this meeting and I flushed a deep red as his eyes told me that he too understood what done.

I took the opportunity to check Charles out. He seemed to flourish with my scrutiny and continued presence. After a long sip of coffee and a casual scan of the restaurants cliental Charles turned is piercing blue eyes on me and murmured softly, “I wish to see that you have kept your promise.”

I gasped sillily, which made him smile, which me flush red again and look away. When I dared to look into his eyes again they seemed to twinkle as he murmured softly again, “Slip away to the men’s and lock yourself in.” Charles calmly waited until I nodded my head in understanding before continuing with his instructions, “When you hear me knock three times on the door you let me in.” Smiling shyly I expressed my embarrassed pleasure with performing such a naughty of act in such a public place by nodding my head enthusiastically.

C observed my enthusiasm calmly before indicating I should leave him with a discrete flick of his chin towards the back of restaurant. As I rose timidly to leave I started when his hand covered mine stopping me half way up. Smiling audaciously Charles purred for only my ears to hear, “Be wearing only what you promised Princess.” I gaped, awed that he would ask but beneath his piercing stare I could only nod my head numbly in consent before another flick of his chin sent me scurrying away to the men’s room in the back of the restaurant.

My body trembled mightily with nervous energy as I gasped in deep breaths trying to calm myself. I couldn’t look at myself in mirror terrified that I would scare myself and flee. Ignoring the reflection as much as the harsh light and limited confines of the toilet would allow I carefully slipped out of my clothes until I stood there shivering in a pair of sheer powder blue panties. I bit my lower lip to give myself the courage to steal a glimpse of my panties bottom in the mirror clinching my cheeks reminding myself of the friend buried deeply inside my Princess pussy. Charles’ Princess.

I gasped covering myself comically with my hands when Charles’ three sharp knocks startled me. Trembling visibly now trepidation I fumbled with the doors clasp before opening the door a fraction to peek out. Relief flooded over me at the sight of Charles standing there smiling. He arched his eyebrows waiting for me to open the door and let him in.

I stumbled back into the small room as Charles pushed in quickly closing the door and locking it. He seemed much bigger in the tight confines of room as he turned to silently to the mirror to look me over as I smiled nervously, hopefully pleasing. I licked my lips nervously wondering where to put my hands as Charles surveyed the reflection my almost naked pantied body in the mirror. Casually exuding strength Eskort and power Charles turned away from the mirror forcing me lean now cowed and slightly scared against the cold back wall.

With a swirl of a finger Charles indicated that he wished me to turn around. As I complied Charles stepped in closer forcing me to brush up against him as I turned. A firm hand in the middle of my back forced me into the wall and held me there. Speechless I could only mew my displeasure as I vainly summoned the courage to push back. My mewing turned to a squeak of distress as Charles’ hard finger traced the lacy edging of panties. Trembling breaths is all I could manage as Charles forced my body against the wall and explored my pantied bottom with his free hand.

Just as I was about to shriek with fear Charles murmured with his mouth close to my ear, “Very nice Princess. Yessss, very nice indeed.” A shudder of passion gripped my body sending me into convulsions as his fingers brushed over my friend pumping it gently into my sissy Princess twat. “OOh yes Princess very fucking nice indeed.” Charles growled throatily into my ear pumping my friend more forcefully. Gasping for breath I let my head drop back allowing my body slip into the erotic heat of the moment.

Charles chuckled knowingly in my ear as he turned my now supplicant body towards him. Charles’ hand again pinned me to the wall as his free fingers caressed my raging sissy-boi clit through the front of my panty. My knees went weak beneath the assault forcing Charles to hold his panting Princess pinned to the wall.

When Charles let go of me I slowly slipped to the filthy bathroom floor before him. As I watched mesmerized he slowly open his trousers to show me his raging erection poking out the front of a pair of sheer white knickers. The sheer material was slick with moisture that Charles had oozed with his excitement. I whimpered meekly as his fingers grasped my head by the hair and his other hand pulled away the shiny moist material from his throbbing member. The bulbous tip of Charles’ cock seemed to stare me in the eye as I watched transfixed as more clear pre-cum oozed from it.

Holding my head still Charles wrapped his free hand about his cock guiding it towards my lips. I sighed and shuddered wantoningly as Charles brushed the hot slick tip of his cock gently over my lips. Then back again. Again, more forcefully, spreading my lips so that his manhood brushed over my teeth. Charles’ hand pumped his erection to force out more of his pre-cum to flood over my lips. Instinctively I licked it away savoring the nutty sweetness.

Abruptly Charles’ cock was gone. His hand released my hair letting my head drop. Bewildered I looked imploring into Charles’ leering grin afraid that I had somehow disappointed him. Laughing gently as he put his manhood away, Charles shook his head at the wanton distressed look in my eyes murmuring quietly, “There’s your taste Princess.” Then he turned on his heal was gone.

I knelt there my body pulsing with passion and want. Panting I lapped away the traces of Charles’ fluid glazing my lips savoring the taste. When the door to the restroom was flung open to expose me I forced it shut with an angry, “Not finished!” Seething with anger and passion I quickly dressed and stormed from the restaurant not bothering to see who would be watching nor caring.

“How could he have done that to me,” I raged silently as I headed home. After a couple of blocks still angry my tongue flicked discreetly over my lips seeking out Charles’ nectar, probing the edges wanting more. By the time I got into my apartment my anger had turned to need. I rushed to the bathroom to look in the mirror to see if there was any Charles I had missed. Whimpering silently with frustration I woke my computer to find a message from C. In a dream I opened the email it said simply, “Did you enjoy your taste Princess?” While I sat there numbly another message arrived.

With a trembling hand I apprehensively opened it. There was no message, only an attachment. Opening the attachment I stared hungrily at a close up of the tip of Charles’ cock spurting a jet of cum towards the camera. Across the bottom of the image in bright pink letters was the message “For My Princess!” Involuntarily my sissy boi pussy cinched about the base of my friend as my gurlie clit spewed Princess cum into my powder blue panties.

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