Like clock work every six months I have a dentist appointment. Most of the time it is the usually cleaning with an occasional set of x-rays. After the cleaning I would collect my new toothbrush and make my next appointment with the receptionist.
I noticed that Mary the receptionist, was accompanied by a young lady behind the counter. When I inquired as to who she was, Mary replied that she was retiring and that Missy will be replacing her once she has been properly trained.
I informed Missy that my name was Todd. She laughed while holding my file and told me she knew that while pointing to the folder.
There was something about Missy that was off. She was pretty, not smoking hot, but cute girl next door pretty. Her hair was a light brown, shoulder length, and with loose curls. She had blue eyes hidden behind a set of black framed glasses. As she talked I stared at her plump lips coated in a subtle pink gloss.
With my credit card in hand Missy got up from the computer and walked over to the credit card machine. I was pleasantly surprised at her physique. Her white silky blouse outlined her small but firm breasts. The short black skirt showed off her sensual hips and perky ass. The slit at the back of her skirt revealed a sexy pair of legs wrapped in sheer white pantyhose. The whole outfit was finished off with a pair of open toed black heels.
As I signed the credit card slip I looked her over once more. Not being able to place the off feeling about her I scanned her from head to nylon covered toes. Scratching my head I collected my new toothbrush and took my appointment reminder from her extended hand. I thanked the ladies and went about my day.
About a month later I was surprised with a call from my dentist office. It was Missy asking me if I could stop by with my insurance card. Seems there was a computer problem when they switched programs she lost my insurance information. I informed her that I was working late and could be there by seven. She mentioned that they close at six but she will stay late sense it was their error.
I pulled into the parking lot around quarter to seven. The lot was empty except for a white Chrysler 200 convertible. I parked next to it and locked the doors on my Tahoe with the push of the fob button as I walked to the office door. As I approached the glass door I could see Missy cautiously looking around the desk and to the door. She bent the corner and proceeded to unlock the door to let me in.
I followed her down the short hallway to the desk. Without a second thought I was checking her out again. Her hair now pulled into a tail revealed a set of diamond coated hoop earrings that moved in rhythm with her ponytail and her step. She had a sleeveless white spandex top on that seamlessly poured into a short faded blue jean skirt. The frade tassles of denim lured my eyes to her gorgeous long legs covered in the most shiny tan toned tights. The outfit was completed by a bright white pair of Sketcher tennis shoes with white socks bunched up and pouring out the top of them.
As we walked to the desk Missy apologized for her informal wear and explained that it was casual day. I managed to stamper out that it was no problem and that she looked great. As she slid behind the desk she smiled at me and extended her hand out to me. I almost forgot why I was there and had to snap out of a trance.
After retrieving my insurance card I placed it in Missy's hand. She spun from the desk and walked over to the copy machine. On her tippy toes she reached for the lid of the copier. She bent over the machine to place my card in the top scanner. My jaw almost hit the floor when her blue jean skirt rose up enough to reveal the bottom of her ass.
With the copies in hand she returned to the desk and offered my insurance card back to me. As mesmerizing she was something still didn't seem right and I just couldn't place it. Missy thanked me for coming by as she slid the copies into my file.
After placing the file into a cabinet she asked if I would be so kind as to walk her out. Without hesitation I accepted the request. Shorty after she locked up the office we walked across the parking lot to our cars. As we arrived between them she leaned against her cute little convertible and thanked me for the escort.
I mentioned that it was my honor to escort such a pretty lady to her car and if it wasn't too forward possibly take her out to dinner. Missy broke eye contact with me and looked down to the pavement. She proceeded to tell me that although she was very flattered by the offer that she would have to pass. She mentioned that she would love to go out to dinner but only if I accepted who she was completely. Missy confessed to me that she was a crossdresser as she dug for her keys in her purse. In a hurry to leave she dropped her keys from her shaking hands.
I retrieved the keys and slowly lowered them into her trembling hands. She looked up at me as I told her that I did not mind that she was a crossdresser and that I thought she was stunning. Through her black framed glasses and her running mascara I could see her blue eyes got just a little brighter. With that she enthusiastically accepted the offer of a dinner date.
Missy requested that I drive so that she could fix her makeup and hair. With that I unlocked and opened the passenger side door for her. She smiled as she stepped up onto the step bars then placed her jean skirt covered ass onto my bucket seat. Slowly she brought one leg and then the other into the truck as the sun danced across her shiny tan tights.
We talked on the way to the restaurant as she utilized the makeup mirror and I drove. Every red light gave me an opportunity to look her way as we talked. At one light she playfully had to inform me the light had turned green as she was applying her lipstick and gloss.
As I pulled up to a popular Japanese restaurant she mentioned that the place was packed. Then she requested that I drop her off at the door so she could check us in as I parked. I watched as she exited the truck and walked to the restaurant door. Looking back at me she swung the door open and pranced inside.
The waiting area was packed but I managed to find my way to Missy. She was sitting on a full bench with other customers. Raising her hand she displayed a paging device. She got up and offered her seat on the bench to me. I insisted that she return to her seat. Laughing, Missy explained that she planned to sit on my lap.
With Missy nestled nicely on my lap we waited for our table. I playfully bounced her up and down a little as we talked. An older gentleman was staring at Missy with lustful eyes. When I pointed him out to her she buried her head in my chest in embarrassment while laughing. Our pager lite up indicating that our table was now available.
The Hostess collected our pager and directed us to a large shoe rack. I removed my boots and placed them in an open cube of the rack. Missy removed her girly Sketchers shoes and her white cotton socks. With just her shiny tan tights covering her feet she walked around the rack for an open cube. With no luck she placed her shoes on top of mine. As she returned I couldn't help but stare at her cute feet. The bright pink polish on her toes penetrated through the shiny hosiery.
As we were sat at our table I enjoyed watching Missy attempt to sit on the floor lady like in her short jean skirt. With chop sticks in hand we enjoyed some culinary delights, some saki, and each other.
Missy proceeded to tell me that she started crossdressing as a teenager in secret. She mentioned that a few years ago she decided to dress as a women in public and has been working on her self confidence and looks ever sense. She figured a behind the desk low profile job would be perfect for overcoming her fears of public dressing. I complemented her on her success and informed her that her hard work didn't go unnoticed.
We finished our meal and I insisted on picking up the check. She agreed only on the terms that she gets to pay next time. I offered a steady hand to her as she hopped up into my SUV. I still could not resist staring at her beautiful legs in those ridiculously shiny tights. With great hesitation I closed the passenger side door and ran around to my side.
As I drove her back to the dentist office to retrieve her car she fixed her lipstick once again. After nearing rear ending another vehicle, I decided to watch the road rather then her applying that slick gloss across her lips. I once again parked along side her car.
We were at the rear of our vehicles when I asked for another date. Missy nodded yes as she put her arms around my neck and kissed me. I kissed her back and we began to kiss more passionately. I lifted her up with a hand on each denim covered ass cheek and lowered her onto the truck lid of her car. With her legs wrapped around me we passionately kissed under the parking lot lights and in the cool evening air.
Missy looked at me with a seductive look in her eyes as she held the keys to the office in her hand. I followed her across the lot watching that jean skirt rock to the left then to the right. The parking lot lights danced on her shiny tights covered legs as she approached the door.
Once inside and the door locked again she giggled as she ran down the hall. Like a high stakes game of hide and seek I searched the various rooms and work spaces for my prize. I found Missy in the hygienists office, perched on a counter cross-legged with a water pic in her hand. She playfully screamed as I approached and sprayed me with water. We laughed as we fought over the free flowing water line.
Completely wet we turned the device off and started kissing again. She ripped the buttons off my shirt as she tore it open to fondle my chest. I lowered the shoulder straps of her spandex top to reveal her magnificent hard wet nipples. With one in between my thumb and index finger and the other in my mouth I worked one with my tongue as I pinched the other. She moaned as she threw her head back and enjoyed the attention her nipples were getting.
With lust filled eyes she ordered me to strip and sit in the dentist chair. In a flash, I was naked laying in the chair with a ragging hard on pointing straight to the ceiling. She slid her skirt down and stepped out of it leaving it on the wet floor. Her wet outfit was amazing, it wasn't a shirt after all but a white leotard over those super shiny wet tights. Missy straddled me on my lower legs pushing her ass against my feet. While looking me in the eyes she lowered her mouth onto my throbbing dick. Watching her work my dick in and out of her pink glossy lips as her diamond hoop earrings swung back and forth was a fantasy come true.
With copious amounts of pre cum in her mouth she moved up me and lowered her mouth to mine. We kissed hard with cum and saliva exchanging between us as we groped each other. She sat up and enjoyed grinding her nylon covered ass against my steel pole. Her own dick was rock hard and tenting the front of her leotard. The wet material completely wrapped her dick displaying every detail including a perfect mushroom shaped head. I continued to tweak her nipples as she slide my dick between her well parted ass cheeks.
With every thrust up and down her dick would rub against the silky nylons and spandex leaving a streak of precum in its path. I grabbed her cock through the slick material and pumped it as she continued the up and down rhythm. My dick couldn't handle her nylon covered ass thrusts anymore and erupted with strand after strand of cum. Missy kept pumping as my cum soaked into her leotard and tights. She shuddered as she had her own orgasm, flooding the front of her tights. I caressed more cum out of her penis into her nylons until her cum meet mine and up to her belly button.
The feeling of the slippery cum soaked tights got me hard again within minutes. Impressed, Missy removed her cum filled outfit but not before collecting a sizable amount of our cum and filling her ass crack with it. After tossing her tights and leotard to the tile floor she mounted me once again.
She easily accepted my stiff member utilizing our cum as lubrication. After bottoming out and with my dick deep inside her she became hard once again herself. Missy slowly raised and lowered herself onto me as her dick twitched and bounced on it's own. Clear droplets of precum oozed from her. As they did I collected them and rubbed them onto her nipples.
After completely coating her nipples in precum I flicked each one with my tongue several times before locking lips with her. Our kiss was deep and hard with our tongues quickly wrestling each other. Her thrusts up and down became faster and harder. The sloshing sound of our cum between us became louder. With one final slam down completely impaling herself on my dick she came again. Long ropes of semen splashed onto me as she shook and moaned while steadying herself with her hands on my chest.
Watching a hands free orgasm was intense and within seconds of Missy's orgasm I erupted my cum volcano deep inside her. Pleased with the feeling of fullness, she collapsed onto my chest. We laid there with my dick still inside her and our cum covered chest together while we caught our breath enjoying the afterglow.
Once we regained our composure we attempted to get dressed. With no buttons left on my shirt I tucked it into my work pants. Missy slid her spandex leotard up her smooth legs until it settled nicely against her cum filled hole and parted her bare ass cheeks. She wrangled into her wet jean skirt and put her socks and shoes back on.
With a playful gleam in her eyes Missy bunched up her cum soaked tan tights and shoved them down the front of my pants against my dick. She wanted to insure that I thought of her the whole ride home. We cleaned up as best we could before we left the dentist office again.
At the cars we exchanged numbers and a final kiss of the night. With the top down on her convertible, she waived as she pulled out of the parking lot onto the empty road. I rubbed my dick against her shiny tights several times as I made my way home thinking of her."
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Pub: 22 Jul 2021 11:50 UTC
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