The first time I remember was when a friend of my mother’s came to the house to give her a permanent haircut. She was in her twenties, single, average build, a pair of long sexy legs, a red full mouth, and I was horny and in a constant state of sexual arousal. She kept smiling at me and licking her lips, giving my mother a perm. I think it was because I kept staring at her sexy legs with her fat high heels. I always thought she had a masculine face.

She wore a very tight red sweater, a tight black skirt, black nylon stockings and ivory stiletto heels. Knowing she had me as a regular audience, Karin shifted her weight from one stiletto heel to another, while rolling the rollers in my mother’s hair, knowing I was watching her every move. I tried to watch television, but my eyes remained fixed on the exciting, sexy woman in the other room. Karin continued to shift her weight from time to time, knowing that her thigh was pushing up her skirt to reveal more and more of her nylon collar and suspenders. She enjoyed it, teasing me with the view of her nylon-clad leg, not to mention the stiff cock in my pants that she saw. She knew I was watching her, and she became bolder and bolder, bending over to pick up deliberately dropped curlers, showing me more of her round, smooth ass, black nylon cuffs and suspenders. She shifted her weight, dropping her stiletto heel to the floor, then defiantly putting it back on and moving to the other foot for a repeat. When recess came, she paced slowly back and forth.

When the break came, she walked out slowly, teasing me, walking slowly past me and into the bathroom, deliberately leaving the door open. Then she placed her nylon-clad foot on the chair, lifted her skirt, straightened her black nylons, and tightened the suspenders. When it was time to leave, she asked me to carry some of her beauty items to the car. She slowly got into the car and showed me much more of her exposed sexy nylon legs and stiletto heels, all the while knowing that as soon as she left I would run into the house and masturbate, dreaming of her stiletto heels, nylons and legs. She pulled up her skirt a few more inches, looked at me and asked if I would like to come over to her house that evening and help her move some things around.

I stood right in front of her, she looked at the wet spot on my pants, licked her red lips, squeezed her legs together, winked and thanked me for the compliment. I arrived at her house that evening, and she greeted me at the door in a tight-fitting, low-cut, red dress that came to just above her knees, black nylons, twelve-inch black stiletto heels, and wet bright red lipstick. My cock immediately rose as she smiled and licked her red lips, knowing that she had me completely in her power. She invited me in, and as I followed her into the living room, she swayed her hips back and forth, walking in those fat horny stiletto heels. She knew she was going to cum in my pants at any moment as I watched her every move. I sat down on the couch and she sat in a chair across from me, crossing her legs several times to give me a good view of the hem of her black nylons and suspenders.

We exchanged small talk, but then she slowly stood up, walked straight over to me, lifted her foot to place it on the table in front of me, pulled up her dress, and smoothed her nylon stockings, looking me straight in the face and licking her red lips. When she finished smoothing both black nylon legs, she sat down next to me, pulled her dress up to her suspenders, and asked if I wanted to feel her nylon legs and suspenders. I felt the nylon material under my hand as I slowly rubbed her leg, wishing this moment would never end. She then stood up, walked a few feet away, pulled her dress up to mid-thigh, turned in a full circle and asked if I liked the view. She walked towards me again, brought her black stiletto heel to my cock and shifted her weight until she was rubbing the toe of her stiletto heel over my now super hard cock.

She told me that she had seen me looking at her legs and stiletto heels and wanted me to know that I could do anything that came to my mind. Natasha told me that she loved to wear sexy clothes and high heels. She moved her black suede pump over my hard cock, asked me to lift her dress higher, so I could see her suspenders, and lifted her stiletto heel up to my cock, shifting her weight until she rubbed the tip of her heel over my now super hard cock. She told me that she had seen me looking at her legs and high heels and wanted me to know that I could do anything that came to mind. Natasha told me that she loved to wear sexy clothes and high heels. Natasha moved her black suede high heel shoe over my hard cock and asked me to lift her dress higher, so I could see her suspenders and … the hem of her nylons and her soaking wet panties.

She lifted her black suede pointed high heel shoe to my cock and shifted her weight until she rubbed the toe of her high heel over my now super hard cock. Then she knelt down in front of me, took off my pants, and used red lipstick to make a mark on my underpants where the wet spot of pre-cum was. Then she kissed the spot again with a little more pressure, again leaving a red lip print. She then took my hard cock out of my underpants and started sucking on it, licking from the bottom up, engulfing the glans with her red lips and moving her head up and down as if there was no end to it. While she was sucking my hard cock, she crawled on the couch and pulled her dress over her smooth sexy ass while guiding my hand to her ripe breasts covered in a black sexy bra. The feel of her sexy lingerie only made my cock harder.

She sucked me harder as I felt her breasts through her sexy black bra; then she stood in front of me and teasingly undid her bra, sat up and placed my hand on her large delicious bare breasts. Her breasts were full, and her nipples became hard as I played with them. She then sat astride my cock and pulled her black silk panties aside before placing them between the folds of her wet pussy as she placed my hands on her sexy ass and guided a delicious breast to my mouth. I sucked on her nipples as she gave them to me, while she rubbed her pussy back and forth on my hard cock. She had left an imprint of red lips on my cock, and as she slid off of me, she reached across the couch to her red lipstick on the small table, painted her lips again, and lay down next to me on the couch.

Again, she placed her red lips over my cock and moved her head up and down over my swollen cock, which was on the verge of cumming. She moved my hand to her slippery ass and then to her wet pussy. My finger found the opening in her pussy and she encouraged me to explore her hot wet pussy. I then came in her wet mouth as she swallowed every drop. She then moved to the end of the couch, spread her nylon legs, grabbed my head and pressed it against her hot, wet pussy. I thought it looked great! I was born a man, she said, and this pussy was made by a doctor. I have to “work” a lot to keep it open. She taught me how to lick her pussy through her black panties, running my tongue over the sexy material. She lifted her nylon legs, took off her panties and wrapped her nylon legs and stiletto heels around my body while I worked my hard tongue over her pussy.

Within minutes, she was coming and I could taste her sweet, hot pussy juice. When she had calmed down a bit, she instructed me to lean back on the couch and she moved so that she could massage my now hardening cock with her stiletto heels. The feel of her stiletto heels against my cock excited me immensely, and within minutes my cock exploded in a cum spraying orgasm, with most of my cum landing on her black nylon stockings and stiletto heels. She laughed hornily and licked her red lips as this was just the beginning of a great friendship. She told me that she had many high heels and sexy clothes that she was very eager to show off and wear for me, not to mention more red lipstick. It had become not only an educational evening, but more importantly, a horny one.