I have to share this story...
Posted: Mon Nov 04, 2019 6:12 pm
I’ve shared many little bits of my fetish with buddies, lovers, and friends in the local swingers community. I’ve never breathed a word of this to anyone until now. I’ve always had a fetish for heels, nylons and legs. I’ve never been a “foot” guy, or at least having feet all over my face. It’s just not my flavor. Well dressed, professional women in skirts, hose and heels are my absolute turn on.
It’s not right to speak evil of the dead, but it’s not evil, and I’m not mentioning her by name. Unfortunately I heard this woman recently passed away from cancer, and I’d like to share the impact she had on my life with someone who might appreciate it.
1987, my junior year, CP was the assistant principal in my high school. Her primary responsibility was to be the school disciplinarian. It’s a thankless position best suited for drill sergeant types who don’t take crap from anyone, and never give an inch. Ms. P seemed to fit the bill. She was a 40-ish divorcee with short styled salt and pepper hair that used to be a nice nut brown. Her face wasn’t unattractive, but she wasn’t interested in her makeup as much as her perceived position of authority. She instantly became my number one interest as soon as I saw her step out of the office wearing her grey suit, white blouse, knee length pencil skirt, tan hose and black patent 3 inch heels. Her figure wasn’t anything special, but she wasn’t rail thin, nor was she heavy by any measure.
It became my mission to pass by the office between classes as often as possible, to catch a glimpse of CP in her hose and heels. I’d pass her in the hallway outside her office and pretend to look at my watch, while analyzing her outfit to give me a good mental jerk-off image later. She had black, brown, grey, taupe, purple, white…pick a color. I’m certain she had enough to wear a different pair every day for the school year! Most were about 3-3.5 inches, but she had a couple that appeared closer to 4 inches high. Pretty much the whole school either made fun of her, or spoke ill of her being the one to bring the smackdowns when we fucked up or acted out. I, however would notice her speaking to other staff, or the secretaries in the office and see her smile. It was an honest, sincere smile that wasn’t at all in line with her hard ass façade she put on for us. I began to smile at her and occasionally say hello. She eventually smiled back and engaged my greeting with one of her own. I was always a bit of a goody goody, and never found myself in her office for disciplinary reasons, but secretly tried to find a way to get closer to her legs and heels. At the end of my Junior year, I was part of a few stage productions that required us to work with administrative staff. We had choir risers set up, and had taken a break from organizing the year end event. I sat on the riser and waited while others were working out some blocking on the stage. CP came and sat down right next to me, taking her heels off and placing them between us! I almost came! The scent was incredible. She seemed lost in thought, or concentrating on whatever was going on across the stage, so I leaned in to try to get a little closer to her shoes, pretending to pay attention to the teachers and students milling around on the stage. I had leaned over a couple inches, when she looked back out of the corner of her eye. I caught her looking back at me and was readied myself for whatever unholy hell she would unleash on me. Instead, she leaned back a bit as if she wanted to share some state secret with me, indicating that I should lean even closer to her. I still wasn’t sure if I was about to die or not, so I leaned over towards her, right above her delicious heels, and she observed how one of the other teachers looked like a drowning swan when she waltzed around the stage pretending to know what she was doing. I snorted out a laugh, barely able to control myself, and she snickered. I took my chance and breathed deeply over her heels before returning to me seated position, hoping she wouldn’t pick up on me being this little pervert. All was well, and I was safe. The year ended without any further contact between us, except her smile was a little nicer towards me when I passed her in the hall.
Senior year. Marching band started before the school year, and the band had pretty free reign over the school during the August weekdays. Teachers and staff were starting to show up and get ready for the school year. CP would occasionally come to the school, but always in jeans, slacks and trainers or flats. The band would march through the main hallway on our way out to the field for practice, and we’d pass by her office. I’d look in and try to catch a glimpse of her hoping she would be wearing the skirts, hose and heels I loved so much. No such luck. Aside from a quick “hello, how was your summer?”, there was nothing.
It was senior year! I was not about to let the year go by without making some serious memories to brag about to my friends and family years later. I participated in some fun things like a senior blockade of the parking lot, stink bombs in the bathrooms, and other silly shit. During an assembly, a couple of us decided it was a smart idea to take BB’s and randomly toss them around the auditorium. If course, We were caught and eventually got our summons to CP’s office. I was pretty embarrassed, but still longed to be near her legs and heels. All three of us were seated across from her desk, and getting the riot act read to us. Apparently on the tossed BB’s cracked a pair of glasses. I genuinely felt bad while the other two snickered about it. She immediately handed down detentions, an in-school suspension for each of us, and a warning to watch it. We got up to leave and she dismissed the other two, keeping me behind. I figured it was because I was the senior and the other two were only juniors, I’d have a special punishment to deal with.
CP got up from her desk and walked to her door. She looked me in the eye, exclaiming a stern “SO?” while pushing her door closed. I’m guessing everyone in the office knew I was about to get ripped in half. As quickly as the door slammed, her tone quieted down. She looked at me and simply asked if that was the most clever thing I could come up with, and did I think I was so damn cool now? She wasn’t barking at me, but I knew better than to smart off. She stood in front of me, glaring at me while leaning back against her desk. I lowered my head and stared at her feet. She was shifting from foot to foot, and would adjust her feet in the heels from time to time. I said nothing and pretended to be deep in thought while she put on the show of the year in front of me. I must have really lost track of time staring, because she simply asked if I was ever going to answer her or just keep staring at her feet and shoes! I felt myself turn six shades of red and looked up at her. She was all business and expected an answer. I simply stammered an “I…I, umm…I…” She gave a cocky smile and said that for a guy who can talk as much as I do, the cat sure has gotten my tongue. I apologized and looked back down, this time in shame of being discovered. She extended her right foot, and let her heel dangle from it, mesmerizing me once again. “My eyes are up here!” I tried another apology and looked into her eyes figuring honesty might be the better approach.
“I’m in lust with your legs and heels!” My face was flush, my heart was pounding, I started getting tunnel vision, and my ears were ringing. I must have been on the verge of passing out. CP said nothing, waiting for me to regain my composure. “Well, I wasn’t expecting that.” Her expression softened. “Honesty is the best policy”, I told her, hoping to gain a bit of dignity back. “This much honest could get you into a world of trouble, young man. This is the kind of honesty that gets people thrown out of their senior year”. I must have turned ghost white as she continued, “but you’re not going to get thrown out. Your honesty is to be commended, but I cannot publicly commend a student for professing his lust after my shoes. So, what am I to do? I can’t punish you for telling me the truth.” She sighed, and seemed to ponder her next move. She straightened herself up and sat in the chair directly next to me, pushing it back to be at 90 degrees to mine. She crossed her left leg over her right and extended it into my lap, resting it right in front of my hardening cock! “So, what is it about them you like so much?”
I almost passed out! I stared at her leg in my lap and described the gentle curve of her calf, the look of the nylon as it stretched around the contours of her ankle, and the line where her shoe met the side of her foot. I wanted to touch her, but couldn’t bring myself to be that brash. The sheen of her nylons and the smooth silhouette it gave her legs. The heels and how they create a sexiness in her posture, and the sound they make on the hard floor when she walks. I went on for about a minute detailing absolutely everything about her that turned me on. She quietly let me talk and just took it all in. When I finished, too scared to move, thinking she was going to give me the third degree, she simply asked if I wanted to touch her heels and legs, I just nodded, and she simply said, “do it”.
My hands were shaking and my heart was in my throat as I reached out and began to run my fingertips in the inside of CP’s left ankle, over her calf, and onto her foot. I looked at her to see anything in her eyes, and all I saw was that she was studying me. A slight smile was in her lips, but she wasn’t giving anything away. My amateur grope session lasted a minute or so, before she took her leg out of my grasp and stood, straightening the chair she was sitting in. My mouth must have been agape because she just blinked at me, saying, “you think I didn’t know?”
“No, I had no idea you knew”.
“I’ve known since early last year, when you made all the effort to pass by the office even when your classes were at the other end of the building, pretending to look at your watch while looking at my shoes, then on the choir risers…you had to know that was a set up”.
Oh shit, I never considered she could just look at my schedule and figure it out…and somehow, never thought an adult would be able to figure out the sexual desires of a young man.
“I’m flattered that you find me attractive, but It’s absolutely wrong to have any type of contact with one of my students. I’m sure you understand, and appreciate my position”. I was about to begin spurting my agreement to her position when she suddenly continued…”I wanna make sure you understand very clearly that anything we do has to remain as big a secret as your lust for my heels and legs…”
You could have knocked me off my chair with a feather…..Was she saying I could have more, and not here in the building? I simply nodded and confirmed that not a breath would be uttered anywhere, ever.
We began our “relationship” with my traveling to her condo in the next suburb once a week. I’d park on the street around the corner, and walk to her door, always after dark, and always in dark clothes. I’d make up some excuse to my folks about hanging with my buddy, at the library, or going to the movies with friends. We met Friday and or Saturday nights, for the better part of a year, continuing on after graduation, till she relocated to another city. We explored any fetish I could think of, and several she suggested that I never would have come up with myself. My clothing, nylon, leg, heel fetish was now permanently seared into my brain. Her heel collection was immense. She knew how good her legs looked, and enjoyed showing them off. The front hall of her condo was marble, and she’d tease me by slowly walking up and down the hall, letting her heels click on the hard surface. I can’t even imagine the number of times she either allowed me to use her nylon covered calves to masturbate all over her feet in her heels, or how she’d bend over to reach the floor, stretching her skirt over her ass, as I knelt behind her, feeling her body through the taught cloth. We explored sexual pleasures porn stars would never have imagined, but I never actually fucked her vaginally. That was the one thing she said we would never do (some personal boundary, I guess), but she taught me many things about pleasuring a woman, vaginally as well as anally. It was the end of summer after I graduated, when she told me she’d be taking a new position in another state. I tried to be the cool guy, and cook her some nice romantic dinner as a gesture of my affection and appreciation. It was less than stellar. She thanked me for my enthusiastic companionship, and I left. I tried calling her the following week, but it just rang. Out of respect, I never drove by her condo during daylight hours, or dared approach on foot at night, fearing some new tenant would see me and call the police.
I accepted that it was just as well. What was I going to do, date her? I think back and wonder if she had any other lovers like me, or whether or not any other young men came onto her as openly as I did? I think of her fondly and remember her as a lovely, sexual woman, and not the ballbusting drill sergeant my fellow classmates remember her as.
It’s not right to speak evil of the dead, but it’s not evil, and I’m not mentioning her by name. Unfortunately I heard this woman recently passed away from cancer, and I’d like to share the impact she had on my life with someone who might appreciate it.
1987, my junior year, CP was the assistant principal in my high school. Her primary responsibility was to be the school disciplinarian. It’s a thankless position best suited for drill sergeant types who don’t take crap from anyone, and never give an inch. Ms. P seemed to fit the bill. She was a 40-ish divorcee with short styled salt and pepper hair that used to be a nice nut brown. Her face wasn’t unattractive, but she wasn’t interested in her makeup as much as her perceived position of authority. She instantly became my number one interest as soon as I saw her step out of the office wearing her grey suit, white blouse, knee length pencil skirt, tan hose and black patent 3 inch heels. Her figure wasn’t anything special, but she wasn’t rail thin, nor was she heavy by any measure.
It became my mission to pass by the office between classes as often as possible, to catch a glimpse of CP in her hose and heels. I’d pass her in the hallway outside her office and pretend to look at my watch, while analyzing her outfit to give me a good mental jerk-off image later. She had black, brown, grey, taupe, purple, white…pick a color. I’m certain she had enough to wear a different pair every day for the school year! Most were about 3-3.5 inches, but she had a couple that appeared closer to 4 inches high. Pretty much the whole school either made fun of her, or spoke ill of her being the one to bring the smackdowns when we fucked up or acted out. I, however would notice her speaking to other staff, or the secretaries in the office and see her smile. It was an honest, sincere smile that wasn’t at all in line with her hard ass façade she put on for us. I began to smile at her and occasionally say hello. She eventually smiled back and engaged my greeting with one of her own. I was always a bit of a goody goody, and never found myself in her office for disciplinary reasons, but secretly tried to find a way to get closer to her legs and heels. At the end of my Junior year, I was part of a few stage productions that required us to work with administrative staff. We had choir risers set up, and had taken a break from organizing the year end event. I sat on the riser and waited while others were working out some blocking on the stage. CP came and sat down right next to me, taking her heels off and placing them between us! I almost came! The scent was incredible. She seemed lost in thought, or concentrating on whatever was going on across the stage, so I leaned in to try to get a little closer to her shoes, pretending to pay attention to the teachers and students milling around on the stage. I had leaned over a couple inches, when she looked back out of the corner of her eye. I caught her looking back at me and was readied myself for whatever unholy hell she would unleash on me. Instead, she leaned back a bit as if she wanted to share some state secret with me, indicating that I should lean even closer to her. I still wasn’t sure if I was about to die or not, so I leaned over towards her, right above her delicious heels, and she observed how one of the other teachers looked like a drowning swan when she waltzed around the stage pretending to know what she was doing. I snorted out a laugh, barely able to control myself, and she snickered. I took my chance and breathed deeply over her heels before returning to me seated position, hoping she wouldn’t pick up on me being this little pervert. All was well, and I was safe. The year ended without any further contact between us, except her smile was a little nicer towards me when I passed her in the hall.
Senior year. Marching band started before the school year, and the band had pretty free reign over the school during the August weekdays. Teachers and staff were starting to show up and get ready for the school year. CP would occasionally come to the school, but always in jeans, slacks and trainers or flats. The band would march through the main hallway on our way out to the field for practice, and we’d pass by her office. I’d look in and try to catch a glimpse of her hoping she would be wearing the skirts, hose and heels I loved so much. No such luck. Aside from a quick “hello, how was your summer?”, there was nothing.
It was senior year! I was not about to let the year go by without making some serious memories to brag about to my friends and family years later. I participated in some fun things like a senior blockade of the parking lot, stink bombs in the bathrooms, and other silly shit. During an assembly, a couple of us decided it was a smart idea to take BB’s and randomly toss them around the auditorium. If course, We were caught and eventually got our summons to CP’s office. I was pretty embarrassed, but still longed to be near her legs and heels. All three of us were seated across from her desk, and getting the riot act read to us. Apparently on the tossed BB’s cracked a pair of glasses. I genuinely felt bad while the other two snickered about it. She immediately handed down detentions, an in-school suspension for each of us, and a warning to watch it. We got up to leave and she dismissed the other two, keeping me behind. I figured it was because I was the senior and the other two were only juniors, I’d have a special punishment to deal with.
CP got up from her desk and walked to her door. She looked me in the eye, exclaiming a stern “SO?” while pushing her door closed. I’m guessing everyone in the office knew I was about to get ripped in half. As quickly as the door slammed, her tone quieted down. She looked at me and simply asked if that was the most clever thing I could come up with, and did I think I was so damn cool now? She wasn’t barking at me, but I knew better than to smart off. She stood in front of me, glaring at me while leaning back against her desk. I lowered my head and stared at her feet. She was shifting from foot to foot, and would adjust her feet in the heels from time to time. I said nothing and pretended to be deep in thought while she put on the show of the year in front of me. I must have really lost track of time staring, because she simply asked if I was ever going to answer her or just keep staring at her feet and shoes! I felt myself turn six shades of red and looked up at her. She was all business and expected an answer. I simply stammered an “I…I, umm…I…” She gave a cocky smile and said that for a guy who can talk as much as I do, the cat sure has gotten my tongue. I apologized and looked back down, this time in shame of being discovered. She extended her right foot, and let her heel dangle from it, mesmerizing me once again. “My eyes are up here!” I tried another apology and looked into her eyes figuring honesty might be the better approach.
“I’m in lust with your legs and heels!” My face was flush, my heart was pounding, I started getting tunnel vision, and my ears were ringing. I must have been on the verge of passing out. CP said nothing, waiting for me to regain my composure. “Well, I wasn’t expecting that.” Her expression softened. “Honesty is the best policy”, I told her, hoping to gain a bit of dignity back. “This much honest could get you into a world of trouble, young man. This is the kind of honesty that gets people thrown out of their senior year”. I must have turned ghost white as she continued, “but you’re not going to get thrown out. Your honesty is to be commended, but I cannot publicly commend a student for professing his lust after my shoes. So, what am I to do? I can’t punish you for telling me the truth.” She sighed, and seemed to ponder her next move. She straightened herself up and sat in the chair directly next to me, pushing it back to be at 90 degrees to mine. She crossed her left leg over her right and extended it into my lap, resting it right in front of my hardening cock! “So, what is it about them you like so much?”
I almost passed out! I stared at her leg in my lap and described the gentle curve of her calf, the look of the nylon as it stretched around the contours of her ankle, and the line where her shoe met the side of her foot. I wanted to touch her, but couldn’t bring myself to be that brash. The sheen of her nylons and the smooth silhouette it gave her legs. The heels and how they create a sexiness in her posture, and the sound they make on the hard floor when she walks. I went on for about a minute detailing absolutely everything about her that turned me on. She quietly let me talk and just took it all in. When I finished, too scared to move, thinking she was going to give me the third degree, she simply asked if I wanted to touch her heels and legs, I just nodded, and she simply said, “do it”.
My hands were shaking and my heart was in my throat as I reached out and began to run my fingertips in the inside of CP’s left ankle, over her calf, and onto her foot. I looked at her to see anything in her eyes, and all I saw was that she was studying me. A slight smile was in her lips, but she wasn’t giving anything away. My amateur grope session lasted a minute or so, before she took her leg out of my grasp and stood, straightening the chair she was sitting in. My mouth must have been agape because she just blinked at me, saying, “you think I didn’t know?”
“No, I had no idea you knew”.
“I’ve known since early last year, when you made all the effort to pass by the office even when your classes were at the other end of the building, pretending to look at your watch while looking at my shoes, then on the choir risers…you had to know that was a set up”.
Oh shit, I never considered she could just look at my schedule and figure it out…and somehow, never thought an adult would be able to figure out the sexual desires of a young man.
“I’m flattered that you find me attractive, but It’s absolutely wrong to have any type of contact with one of my students. I’m sure you understand, and appreciate my position”. I was about to begin spurting my agreement to her position when she suddenly continued…”I wanna make sure you understand very clearly that anything we do has to remain as big a secret as your lust for my heels and legs…”
You could have knocked me off my chair with a feather…..Was she saying I could have more, and not here in the building? I simply nodded and confirmed that not a breath would be uttered anywhere, ever.
We began our “relationship” with my traveling to her condo in the next suburb once a week. I’d park on the street around the corner, and walk to her door, always after dark, and always in dark clothes. I’d make up some excuse to my folks about hanging with my buddy, at the library, or going to the movies with friends. We met Friday and or Saturday nights, for the better part of a year, continuing on after graduation, till she relocated to another city. We explored any fetish I could think of, and several she suggested that I never would have come up with myself. My clothing, nylon, leg, heel fetish was now permanently seared into my brain. Her heel collection was immense. She knew how good her legs looked, and enjoyed showing them off. The front hall of her condo was marble, and she’d tease me by slowly walking up and down the hall, letting her heels click on the hard surface. I can’t even imagine the number of times she either allowed me to use her nylon covered calves to masturbate all over her feet in her heels, or how she’d bend over to reach the floor, stretching her skirt over her ass, as I knelt behind her, feeling her body through the taught cloth. We explored sexual pleasures porn stars would never have imagined, but I never actually fucked her vaginally. That was the one thing she said we would never do (some personal boundary, I guess), but she taught me many things about pleasuring a woman, vaginally as well as anally. It was the end of summer after I graduated, when she told me she’d be taking a new position in another state. I tried to be the cool guy, and cook her some nice romantic dinner as a gesture of my affection and appreciation. It was less than stellar. She thanked me for my enthusiastic companionship, and I left. I tried calling her the following week, but it just rang. Out of respect, I never drove by her condo during daylight hours, or dared approach on foot at night, fearing some new tenant would see me and call the police.
I accepted that it was just as well. What was I going to do, date her? I think back and wonder if she had any other lovers like me, or whether or not any other young men came onto her as openly as I did? I think of her fondly and remember her as a lovely, sexual woman, and not the ballbusting drill sergeant my fellow classmates remember her as.
