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It was a very hot, very windy day in the Loop when I saw the girl of my dreams. I had just ducked out of another boring meeting where I was listening to the rationalizations of senior management about why our raises and bonuses would be so small again this year.
My only interest in the meeting came with the occasional flash of thigh I caught when a young female executive crossed and recrossed her fine long legs across from me at the "U" shaped table. I was restless, and a bit uncomfortable as my cock stiffened in response to her "almost" beaver shots.
Unable to listen to any more of the bad news, I went to the phone during our break, and called my number one account to concoct a good enough reason to bail out of the session. Luckily, they needed a real copy of a proposal I had described on the phone the day before. They said I didn't need to get it there until the end of the business day or first thing the next morning. "No problem" I said, "I'll get it over as soon as I can." Armed with my fortunate "emergency", I headed out to find a cool place to have a beer and maybe watch the Sox game, knowing I'd get the proposal over on my way in tomorrow.
The place I stepped into was filled with a noisy conventioneers playing hooky from some trade show at McCormack Place. Not my cup of tea, so after one quick one, I strolled back out under the El tracks on Wabash Avenue to find someplace a bit quieter. As I approached the stairs from the station overhead, my eyes were drawn to a pair of bare legs in high heels just in front of me, coming down the stairs. A bolt of electricity shot through me as turned my head just in time to see how a gust of wind flipped the white gauzy dress up around her waist.
Bare legs all the way up to a pair of full cut, stretch lace panties! She brushed at the floating material, but could not get it to settle back down with that hot wind swirling around the corner of the building. I realized I had unconsciously stopped even with her as she stopped to poke her dress down. Now I was obviously staring up at her pretty legs and panties as busy shoppers brushed on past me. My face flushed as I realized how geeky I looked, a middle aged guy in a conservative blue suit, standing and looking up a woman's dress.
She got control of her clothes again without noticing me, and continued down the stairs. She darted across Madison against the light, as I was caught by the "Don't Walk" light. I stood at the corner watching as the wind picked up the light material of her dress and sent it sailing up around her waist again.
I was not the only one gawking this time; a cabbie almost rear-ended a long black limo when he turned and stuck his head out his window to get a better look; an older gentleman walked right out into the traffic and was almost run down by a CTA bus whose driver was paying more attention to our damsel in distress than to his bus's whereabouts; and a young high school aged kid bumped into a lady who promptly dropped an armful of packages.
It felt like my eyes suddenly developed telescopic capabilities, because I was sure that I could see the nametag through the stretchy white lace of her panties. Certainly all my attention had been focused on the sight of her batting at that floating dress, and the way the afternoon sun streamed down onto her perfect ass and legs. She must have worked out regularly, because her thighs seemed sculpted of marble and her ass cheeks flexed strongly as she walked on down the sidewalk. I took advantage of a break in traffic and headed out west on Madison where she had finally brushed the pesky dress back into place.
The strong sunlight washed though her dress, revealing in dark shadows, the outline of her body. Another gust arrived and up went the skirt, not as high this time, but I was fairly close behind her and enjoyed the sight of lace encased cheeks and elastic pressing into tanned flesh. A quick brush brought things under control again, but I realized that I was now following this woman, and had never even looked at her face. The loud bleating of a car horn startled both of us, and she turned to see what the commotion was all about. What a face! Not a babyfat kid, but a woman not too much younger than me.
I almost walked right into her as she slowed to watch the almost accident in the street, but caught myself and scrambled to come up with a reason to say something to her. Just then she turned to the right and walked into the lobby of an older office building I vaguely recognized. Instinctlively, I followed and stood next to her at the elevator. No one else was there with us, and I strained to see the list of tennants with my sunblinded eyes. I tried to look casual when I looked over her way, and fortunately she was looking up at the little dial showing the elevator's progress down towards us. The air conditioning had done wonderful things to her nipples which poked out nicely against the fitted top of her white dress, and little goose bumps on her arms raised the fine hairs there to attention as well. Back to the listing, why did I know this place?
A bell rang, the doors opened and an older couple tottered out into the lobby as we stepped into the vacant car. She pressed 11 looked over to me and I smiled weakly and said "my floor too." I could smell the lilac perfume that drifted over from her and immediately flashed back to a beautiful, tall model I had spent a very long time watching at the Chrysler exhibit at the Auto Show I had gone to when I was twelve. She had worn the same perfume and I always think of her whenever I smelled lilacs. The doors opened and she turned left down the dark hallway.
White glass doors were painted with the names of doctors and dentists who practiced here. The faint medicinal smells of their offices slowly took the place of her flowery scent, and then I realized why I knew this building. A dentist I used to go to years ago when I lived in the city had his office here...Dr Kahn. Down at the end of the hall, a door rattled shut, and I realized I was still standing by the elevator, with no reason for being where I was except that I had fallen under the spell of a beautiful woman with a floating dress and pretty white lace panties.
Now I had to at least find out where she had gone, so I quietly walked down the hall to the last door and read, "Dr. Robert Kahn, DDS". "There is a god!" I thought as I reached for the doorknob. Inside, I saw the familiar small waiting area with five chairs separated by small tables holding well thumbed magazines. Not a soul in sight to distract me as I looked around and recalled the long hours I'd spent in the reclining chair in back during two endlesss root canals. "Can I help you?" asked a voice from behind the counter dividing the waiting area from where the secretary sat. I looked over my shoulder at the face of the woman I had so letcherously followed. "Ahhh....I was in the Loop and thought I'd see if I could get an appointment with Dr. Kahn for a checkup" I managed to blurt out. "It's been a while since I was here last and wasn't sure if he was still in this building.
"Yes, he is, but he's not here today, it's his day off. His secretary went home early today, and I'm just finishing up some paperwork. Would you like me to schedule an appointment for you?" "Gee, ah...I don't know, I was just hoping he could clean my teeth since I was downtown today. I live up in Highland Park now", I said, not having any more plan than I'd already put into play.
"Oh, if that's all you need, I can take care of you, I'm his hygenist" she said, filling in the blank in my pitifully thin strategy. "OK, that'd be great, but I don't know if the doctor still has my records here, it's been a few years since I was here last" I said. She took my name, walked back to the files and bent over to scan the folders in the lower drawer. Long, long legs again brought back the image I'd first seen coming down the stairs from the elevated tracks.
"Oh, here you are, we were just getting ready to put your file into our inactive section. I can do a cleaning, and then when Bob is back tomorrow, he can set up a time for an exam, OK?" "Sure, great...Are you sure that you're not too busy to do a cleaning now?" I asked, still a bit unsure why I was here when all I'd set out to do was ditch a meeting and get a beer. "No problem at all, I was just fininshing up. It won't take long at all."
After she finished with my teeth, I realized I had a "semi" erection from her leaning and brushing against me while she worked. Later, I kept up a conversation while she did the paperwork on me. I suggested that if she was going to be leaving the offfice soon I'd like to buy her a drink or a bite to eat for being so helpful.
No elaborate story here about sex in the chair, or other adolescent fantasies. But fortunately, we did go out for a quiet drink and ended up at her place a couple of nights later after going to the movies. She was wearing a similar gauzy dress and later, while kissing her on the sofa, I ran my hand up along the outside of her hard thigh to the place where I could feel the elastic of her panties.
Not stretch lace this time, but smooth satin finish nylon; my weakness. Our breathing got more and more labored as we kissed, and I moved my hand up around her butt feeling electricity course though me from the nylon. Full cut briefs that enclosed her tiny waist with a fabric covered elastic band! As I reached around to the front of her panties, I felt her mound and soft pubic hair through the smooth nylon, and slipped my middle finger down to the double fabric of her panty crotch. It was very warm and damp, and when I pushed my finger in to massage her clit, the fabric became drenched with her slippery fluids.
After more petting, she stood up and slipped the gauze dress up over her head revealing a white bra and full cut white satin nylon panties. She must have noticed the catch in my breating because she stopped undressing and helped me out of my shirt, pants and jockey shorts. My erection was full and she pushed me back on the sofa and planted one knee on either side of my legs, pinning me to the back while she reached back to release the clasp on her bra. It fell away and now she wrapped her arms around my head and pressed my face between her beautiful breasts. As she did so, she slid her hips forward so my cock made full contact with the panties she was still wearing. Unconsciously, I began to thrust against her smooth belly as I licked and nibbled her breasts. We kissed deeply, and she started counter thrusts with her hips, matching mine. I rolled her over onto the sofa, never losing the position we were locked in. Massaging her pink nipples, and rubbing my cock on her nylon panties, I realized that my fantasy woman was helping me to fulfill my darkest dream.
She hooked her legs up around my waist and raised her hips up to meet the thrusting of my cock, while I worked myself to a position where my cock was rubbing along her pussy slit and against her clit. The feeling of nylon panties against my dick was almost more than I could stand. I could feel how the fabric had slipped into her pussy's opening and was now soaked with her lubrication. She trembled and came first once, then a second time, and as she bucked against my hard cock, I felt the head catch against the opening to her vagina. I pulled back and thrust again, but again the slippery nylon led me into her cunt opening. She was now coming with abandon and bucked against me tightly, pushing my nylon covered cock more and more deeply into her.
The nylon fabric followed our thrusting, and put the additional pressure she wanted against her swollen clit, rubbing her to a frantic climax. My cock was likewise being rubbed, encased as it was in smooth, wet nylon surrounded by hot lubricated cunt walls. The combination of nylon friction and the excitement of this fantasy woman cumming in wild abandon generated the most fantastic orgasm of my life.
I must have roared pretty loudly, because she looked directly into my eyes and took hold of my face in both hands and kissed me so deeply I was sure she could see into my soul. Locked into her as I was, we kissed for long minutes and she continued to rock us back and forth with gentle hip movements. As I felt myself growing smaller inside her, I could feel the wet fabric of her panties sliding across my super sensitive cock skin.
The combination of kisses and sliding in wet nylon soon had my erection back at full staff, and we began our gyrations again.
The second time I came, I had waited for her to begin to come for the third time before I let myself go in order to prolong the delicious sensations inside her pussy. When we finished - together, I rolled off and out of her and looked down for the first time at what we had done. Her panties were drawn down from the waist halfway between her belly button and cunt, and were pulled deeply into her ass crack from behind. Her slit was entirely covered by the panties, and my semen was forming a slow rivulet down her ass crack and onto the sofa cushion.
We kissed and rubbed each other silently for a long time before anything about what we'd just done was said. She told me she had not ever experienced an orgasm before where she hadn't been touched by a hand; her's or her partner's. She looked down for the first time and saw what had been touching her clit as we fucked, and didn't know what to say. I bumbled on about having been so excited by her and the moment that I didn't realize that I had pushed her underwear inside when she started to come the first time.
She thought it was pretty kinky, but couldn't get over the strength of her orgasm and the different way it felt than when a finger or vibrator touched her. I said I'd tidy her up a bit and slid the panties down her hips until they started to pull out. She stopped me and asked me to touch her clit through the panties one more time. I complied and she came again, much quieter this time, but gripped my hand with her strong thighs as she rode my nyloned fingers to completion.
Later, she told me her first boyfriend had played with her through her panties whenever they had parked to make out. She was also from an older time and was "saving herself" so never had really fucked him. She has strong memories of being rubbed with nylon covered fingers under her dress.
She said her boyfriend never tried to force her to have sex to prove her love, but needed to be relieved just as he made her come. She would rub him through his chinos, but was afraid of making a wet stain he'd have to explain at home, so either unzipped him and rubbed him with her hand, or (years later) took him into her mouth.
When she jacked him off by hand, he often didn't have a hankerchief to catch his cum, so she would skin off her panties and use them to keep from messing up the car seat. She remembers that he seemed to be extra excited whenever she did that, and seemed to get forgetful about hankies pretty often.
She also remembered the quick "dry humps" they'd occasionally have when he'd roll over on top of him, hike up her skirt and rub against her mound through her slip and panties. Sometimes she'd notice that his cock had "slipped" out of his shorts and was rubbing directly against the nylon. Instead of his shorts catching his load, her underwear would end up wet and sticky.
We talked for a long time, and I admitted to having had similar experiences growing up, and how I did like the way nylon felt when I touched it with my hand, or when it was rubbed around my body. After we went together for a few months and re-played our impromptu coupling a couple more times, with almost the same excitement level, I began to talk more and more honestly about myself, including how I thought I got my interest in panties. We stayed together for almost a year until my job took me out of Chicago to the West Coast, and I eventually lost all contact with her...after she got married to some doctor.