If you are a true nylon lover with a focus on crossdressing then you should appreciate these stories. Please bookmark as more to be added.
OLDER SISTER’S NYLONS CH. 01
This took place in 1966. A time when the fashion called for women too wear girdles, garters, and shiny ultra sheer reinforced heel and toe nylons, spiked heel pumps/mules daily! A time when my fetish for nylons was young and in full bloom!
You little pervert! I jumped up, dropped the high heel pump in my hand that I had held over my nose and I turned around and found my beautiful older sister, Sharon standing in her bedroom doorway with her arms crossed.
I froze and was speechless. I thought I was safe and alone in the house. With my Mom having to work on Saturday’s and I believed my sister had left to go shopping with her girlfriend. In my mind I had a couple of hours to myself.
Caught up in my excitement, obsession, and in need for sexual release I did not even hear my sister Sharon open the front door down stairs and come up the carpeted stairs to her room.
I felt my heart pounding in my chest and could feel my face turning beat red with embarrassment. I started to stammer and stutter trying to find words of forgiveness praying and begging to keep this from Mom. There I was in my sister’s bedroom, on her floor with many of her stockings and heels around me jerking off with one of my sister’s nylon stockings pulled over, up and around my hard cock. Adding to my humiliation, I was also wearing a pair of her stockings and smelling one of her spiked heel pumps.
“How long were you standing….” I stuttered.
“Never mind that!” she snapped before I could finish my question. “Long enough to see my little pervert brother getting ready to cum on my stockings!” She yelled, her face turning red.
Sharon was loving but also always very strict, and almost cruel with me in her demanding ways. I knew I was in for it!
“I knew it! I knew you were getting into my nylons! I found some snags and
pre-cum stains on my nylons you little stocking pervert! I knew if I snuck back
home I would catch you! Oh my god your wearing my stockings and
smelling my heels!” she cried.
I see you always looking at my legs and feet and running into the bathroom to jerk off! Then always finding my nylons in my drawer a mess and my new ones not folded right in the boxes. I knew it I just knew it!” she repeated.
As she slowly walked into the room toward me I pulled off her stocking that was over my hard-on letting it fall to the floor. I tried to cover up my erection with both hands and felt the nylons I was wearing fall and gather below my knees. Her ultra sheer nylon legs swished, and the sunlight from the bedroom window made them sparkle as she walked toward me; her ankles wiggled from her pointed toe, tall, black, four inch stiletto, spiked heels as they dug deep into the carpet.
As she approached me, I stepped backward until I was up against her dresser with her blocking my exit from her room. She stopped and stood with her hands on her hips and her legs spread slightly. Wearing those tall four inch spiked heels she stood taller than I did, which added to the power that she knew she had over me in my submissive, begging for mercy state. She was dressed in her usual slutty style that she was known for, and it always gave me boners. Her skirt was so tight I could see the marks of her garter tab welts and knew where her stocking tops ended. Her skirt being so short I could just start to see the beginning of her shiny black stocking tops even though she wore very long stockings.
Just turning eighteen I was dealing with my life long passion and fetish for nylons.
My older sister did not help my obsession. She was nineteen looking like twenty four, tall, drop
dead gorgeous with legs of a model. She was always getting into trouble with our
Mom about the way she dressed but did not care. And loved the attention she was
getting from all the men. Her best friend, Sue dressed the same and both of them had a bad reputation already for being sexually active. Between my sister Sharon and Sue, both of them drained me. If I was not jerking off to my sister’s legs I was jerking off to the thought of Sue’s.
She starred at me up and down and she was close enough for me to smell her perfume and the hair spray in that classic tall beehive hairstyle she wore. With her heavy dark eyeliner I could see her eyebrow rise and the stern frown on her face turn into a more controlling smile.
“Please,” I begged, “you’re not going to tell Mom are you? I’ll do anything!”
“Anything?” my sister asked.
“Yes please, anything your ask, Sis!” I promised.
My sister removed her arms from her hips and pointed one finger at me.
“Your mine! You hear me your mine! You owe me big time! From now on you do as I command! Half of your allowance is mine for doing these nasty things to my stockings and you will buy all of my nylons from now on! You understand me?”
“Yes, oh yes I understand! Anything you want I promise!” I whimpered in front of her.
“Good, we understand each other then!” she said.
With that same controlling look on her face she turned and walked to one of her dresser drawers and fumbled for a moment through her lingerie pulling out a black short open bottom girdle. It had 6 garters attached to it with a side zipper.
She walked back over to me and held it out on one of her fingers and said “Finish!”
I stammered once again with question to her offering.
“Finish jerking off in front of me you little nylon pervert! I want to see you cum, I want to laugh at your male weakness for my stockings and heels!”
She looked at my stockings now hanging lose around my ankles. “If your are going to wear my stockings you must wear them right. Put this girdle on, and don’t act like you never have worn it before. I have found some crusty pre-cum stains on it. I know you have been into my lingerie drawer’s before.
“Well, haven’t you?”
With my face still red I lowered my head not to look into her eyes, “Yes, yes I have!” I confessed.
“Good” she said dropping the garment out of her fingers to the floor. “Do as your are told Sissy! I think I am actually going to enjoy this!” she smiled and laughed at me.
She turned and sat on the bed and slowly crossed her smooth nylon legs; the
room filled with the swish sound of her black stockings crossing against each other. Her skirt was so short as she sat crossing her legs, the stocking tops came into full view exposing her metal garter clasps and black tabs holding her stocking tops so smooth and taunt. She did not even try to pull her skirt down and then let her spiked heel slip off her nylon heel and dangle on her toes. She bounced her foot up and down and the sight of her smooth high arches and the
dark reinforced heel of her stocking foot was giving me an instant hard on again.
“Hurry I don’t have all day!” she said.
I turned my back to her to hide my erection as I went to pick up the girdle.
“No, No turn around and let me see everything! Let me see your little sissy hard-on!”
I slowly turned to her and felt my heart pound in my chest with excitement as well as a state of embarrassment. I removed my hands for the first time in front of her and exposed my cock. I picked up the girdle and slipped my stocking feet threw the girdle opening and pulled it up and over my now full erection. As the smooth but firm girdle touched my hard shaft I gasped for a moment at the cool satin touch. As it slid up higher my hard dick sprang out back into the open and stood up firm, erect and tall against the black satin front panel of the girdle. I loved the feel of her girdle on me as it shaped and hugged my ass so tight.
My sister’s eyes opened wider and she starred at my excitement. I reached over and zipped up the side zipper, I reached down and pulled one, then the other shiny, black, ultra
sheer stockings up my leg to the garters and hooked them as I have done so many times before. My sister pointed to a pair of her black 4″ mules that I had out laying on the floor.
Sis snapped, “Now the heels too!”
I held on to the top of the dresser as I slipped my feet into the tall thin mules, the feeling of the smooth cool leather soles of the heels against the silky nylon soles of my feet was something I loved. As I stood facing her now wearing her black nylons and the tight girdle I almost felt weak in the knees. My ankles were shaking from the tall thin stiletto heels as I tried to keep my balance on the thick bedroom rug.
I could feel the start of a little pre-cum as my cock strained upward against the smooth satin girdle panel. My balls ached and I felt as if I could just shoot ropes of cum into the air without even touching my cock.
The sight of my sister’s nylon legs in front of me, and the whole erotic feeling of standing in front of her wearing her stockings and heels made my body feel numb. Still embarrassed of being in front of my sister and fully exposed with my cock cum ready for launch, I began to feel a little more confident and felt my cock stiffen even more.
“Good, very good!” Sharon said in a now much lower and seductive voice.
“Come over to me now!” she said, pointing to a spot directly in front of her. I walked in short steps not to lose my balance from the towering heels in front of her. Her nylon legs were so beautiful I could hardly stand it. They were still crossed with her stocking tops still in full view and the high gloss and shiny stockings reflected light in the room and sparkled. Both of us wore the same nylons, the tops of her stockings matched mine with the thin green stripe at the top of each one. On one of her stockings I could see the writing of the brand label clearly against the jet-black shiny stocking top. “Hanes” in fancy script was stretched being pulled up and out of shape from the garter tab just above it.
Sharon was now staring at my cock and with almost a whisper but load enough for me to hear, “God dam your fucking big for your age!”
Then, with a blink of her eyes, she was back to reality and took her eyes off my cock and looked up at me. “On your knees” she ordered me. I was down on the soft rug on my stocking knees in seconds, with her crossed leg in front of me, and her high heel inches from my throbbing hard on.
“Good now start to jerk off sissy!” She commanded.
I grabbed my cock and started to stroke it slowly looking at her nylon legs and the dark reinforcements on her stocking toes. She stared long and hard at me and I could tell from her eyes so wide open looking at my stiff cock that she was in awe of it. She started to breathe a little heavily herself and her blank expression turned from a commanding smile to an erotic expression of sexual need.
“So you like smelling my shoes don’t you?” she interrogated me.
In shame of my weakness for the smell of my sister’s pumps I said in a low voice “Yes, yes I do”
“Your such a nasty little pervert! Your dying to smell my stinky nylon feet aren’t you?” she taunted.
With that she kicked off her pumps and placed her sole of one of her stocking feet up to my face and the other foot pressed firmly against my hard shaft. I almost fell back from the shock and sensation.
“Your always trying to brush up against my stockings aren’t you sissy? Act like it was just a accident that your hand happen to brush against my nylons, but I knew what you were trying to doing; trying to cop a feel of my nylons so you could run to the bathroom and jerk-off huh?” she demanded.
I could not believe the feeling of her nylon foot on my cock and my nostrils filled with her foot scent that I loved. I confessed in a moaning soft shamefull voice my weakness for her stockings and heels.
I still could not believe Sharon’s silky smooth nylon foot was rubbing up against my face and most of all, touching my cock. I moaned with pleasure as she moved her nylon foot against my rock hard shaft. I moved my nose right above the ball of her foot just under her toes and breathed in deeply.
Her foot was still warm from being in her leather pumps. The scent of the nylon & leather was stronger than just her shoe smell, which I was use to jerking off too. I just let myself go and started to lick and suck her beautiful nylon toes. The dark, reinforced nylon of the toes felt so slick and smooth against my tongue. I ran my tongue and kisses from her toes down and up her smooth high arches to the dark, reinforced nylon heel.
I grabbed the nylon calf of her other leg that was working against my cock and slid my hands up and down the ultra sheer stockings as I began pushing her leg closer to me humping the smooth nylon sole of her foot. Within moments, I was already on the verge of Cuming against her nylon foot. My sister knew it and reached for my hair and pulled my head back removing her foot from my cock.
She laughed at me and said “No! No not yet!”
With my heart pounding in my chest, I begged her for my sperm release! She opened her legs wide in front of me and pulled her skirt up waist high. I could clearly see her thin shiny black nylon panties that were now stuck against her pussy that was shiny and wet. I have only seen pictures and never seen a real pussy before and my body almost shook with nervousness.
“Now my little sissy nylon pervert it’s time to obey my commands!” she directed.
“Yes Sis, yes anything!” I cried, licking my lips at the sight before my eyes.
She grabbed the hair on my head and pulled my face down to just the top of her
nylon knees. Her nylons were so smooth and slick above her knees and thighs
because of the garters pulling the stocking tops so taunt. Her nylons felt even
smoother than I dreamed of in that area. I started kissing her nylon thighs and
followed her guidance from her hands on my hair upward.
I got to her stocking tops, kissed licked the dark shiny bands and felt my tongue rub across the
garter tab hooked to the nylon and up the length of one of the black garter straps. My tongue slid off the garter strap and against her smooth, soft, bare skin just under her panties. For the first time I could smell her pussy just inches form my face. It was a stronger scent than I was used to from smelling her panties in her hamper. She pulled me closer and my tongue found the wet spot
against her nylon panties.
She gave out a soft moan and I felt her body tense. I started to lick her pussy through the thin nylon panties and within moments the front of her panties was now totally damp and covered with slick pussy wetness. We were both now moaning and she let one of her hands go and reached down pulling her panties to one side. There in front of me was her slick pussy. The damp nylon panties were no longer holding her large pussy lips flat and they hung out for me. I started to suck, lick, and pull on them with my mouth.
“Oh my god she gasped! That’s it you little nylon sissy suck my pussy! Do as you’re told and suck it good!” she demanded.
She pulled my head tighter and guided me up higher. My tongue was going places it had never gone before but somehow knew where to go and with my sister’s moaning and whimpering sounds and body movements helped guide my eager tongue. I felt my tongue slip deep into her warm pussy; I started to tongue fuck her and made sure that she was going to be rewarded for this intense erotic moment. With her pussy moving all over my face and her moans of “Yes, yes, yes!”
My hands were now holding and sliding up and down her smooth nylon legs. I was in heaven just to be holding and feeling her beautiful stocking legs as I worshiped her pussy. She moved one of her ankles inward so my hard cock would rest against her stocking leg. I moaned and gasped at the feel of my sensitive shaft coming in contact with her nylons. I rubbed my cock slowly up and down and against her nylon leg as I served her needs. She guided my tongue to a higher spot and I felt her whole body shake. I sucked and flicked my tongue with ease against it. I never felt anything so wet and slick as her pussy juice dripped from my chin.
“There right there! That’s it lick it good, YES! YES!”
I felt her nylon thighs tighten around my head and felt her body begin to shudder and shake. She pulled harder on my hair and screamed with pleasure. I felt her pussy spasm in my mouth as she was gasping for air. She let go of my hair and I felt her body go from a tense state to a total relaxed stillness and soft moans.
I pulled my tongue out and my head back slowly and watched her shiny thin black
nylon panties slide back over and stick to her totally soaked pussy. I leaned
forward once again and my tongue found and licked the slick nylon panties. She
pushed my shoulders back and said trying to regain her breath “Good, that was
very fucking good!
“Ok now you get to finish what your started my nylon sissy pervert!” she whispered breathless. She returned her stocking foot to my still ridged cock and I once again gasped at the soft slick feel of her nylon foot. As she started rubbing my cock with her nylon foot she said, “Don’t think that just because you made me cum so fucking hard that you’re off the hook! Your still mine and owe me! I can tell Mom that my brother is a nylon pervert sissy that loves wearing stockings and heels!”
“Oh yes, Sis please anything you want!” I pleaded.
“Good then you will do what I say right?” she said snidely.
“Yes anything!” I promised.
“Good, How bad to you want to cum on against my nylons?” she teased.
“Oh my god Sis SO BAD!” I begged.
She slowly started to increase her strokes against my hard shaft with her soles
of her feet. I moaned with pleasure I never felt before. My sister (Name) was enjoying
her newfound power over me and somehow I knew it was not going to end yet.
“If you cum on my stockings you will have to clean them do you understand?” she asked.
Confused a little I responded, ” yes of course I will gladly wash them for you.”
“No not wash them lick them clean!” she laughed.
Having never tasted my own cum before I hesitated with an answer; she knew this was the ultimate humiliation for me. On the verge of blowing my load I would have done anything she asked of me. “Yes, yes I will do anything you ask!” I agreed.
With that she increased her foot speed on my still rock hard cock in between her smooth stocking soles of her feet. The sight of her nylon legs exposed to the garters in full view of me and the sight of her dark reinforced nylon heels and toes wrapped around my cock made my heart pound. As I looked down at my cock it was full and hard sticking out just below my open bottom girdle. The black bands of my stocking tops I was wearing were straining from the short garters. Her soles were so smooth they felt slippery form the nylons and I moaned from each stroke from the bottom of my shaft up to my now huge red cock’s head. I felt myself losing control with each new nylon stroke.
She told me to pick up one of her pumps on the floor next to me and smell it! I reached over and picked up the old worn leather spiked heel, held the open sole of the shoe to my nose and inhaled deeply.
“Smell my stinky shoe you sissy!” she said sarcastically.
That was it, the scent of her stinky shoe and the feel of my cock in her foot vice were too much and I began to lose it. I moaned with a whimpering muffled sound into her shoe as I felt my balls begin to release my floodgates of cum. My cum was there! I could feel it start to race then shoot up the length of my shaft. I was at that point of no return and that split second before the build up of sperm erupts out of the end of the pee hole. I dropped the shoe from my nose and grabbed my sister’s nylon ankles for balance as my nylon knees started to slip on the plush rug under my knees, I moaned out with a “Sis, I’m I’M CUMMING!”
My first shot of cum was like I was holding a hose with my thumb over the opening of it. It squirted so hard and high my sister’s eyes were wide open and gasped at the sight. My second shot was full and powerful. The huge gob of pearl white cum sprayed and landed across her black stockings legs. A second, third and forth spurt just made more of a mess on her nylons and the hot cum made my cock slide smoother between her nylon soles of her feet.
She held my cock in her feet and would not let go until the last of my sperm oozed out of the end of my foot fucked cock and down between the soles of her feet.
Totally spent, and out of breath she just kept sliding her nylon feet up and down my now
cum slick cock drawing out the last drops of my cum. I moaned with pleasure from
the biggest cum I have ever had.
She held up her foot to my face for me to perform my final duty. I hesitated for a moment staring at her stockings covered with my spent cum.
“Do it!” She commanded in a stern voice and I held her ankle to support her beautiful leg. I obeyed her command and started to smear my cum across her foot with my tongue.
She sharply responded with “Don’t smear it! Lick it off! All of it! Taste you cum sissy, you will get use to the salty taste of it!”
I licked clean her feet and finally the huge cum stains higher up across her nylon legs. The taste was bitter and salty but not as bad as I thought it would be. I started to get another hard on and she pushed my face off her legs.
“You nasty little foot slave, you’re getting another fucking hard on already?” She was happy with my cleaning efforts and laughed at me. “Enough for now you have things to do!” She stood up smoothed and adjusted her stockings at the garters and pulled down her tight skirt. She slipped into her 4″ spiked heels with her nylon feet still damp from my tongue wash. She told me to get dressed with my jeans on over the girdle and stockings and not to take them off. I was to wear them the rest of the day as we went out shopping.
“I am going to enjoy watching you ask the sales lady at the hosiery counter for nylons for me as well as yourself!”
She told me she was not going to change her stockings and she liked the feel of
my drying left over cum stains. As we started to leave the house, she said she
had to make a quick phone call. She sat down on the kitchen chair and waited
for the phone on the other end to answer she crossed her legs once again; I could
clearly see her stockings tops.
As she dangled her heel from her foot I could still see the patches of damp nylon especially over her smooth arches and dark reinforced heel. I started to get another boner from the sight of her nylons and the way the stockings I was still wearing felt under my jeans.
“Hey Sue, yes it’s me; I coming over now to pick you up to go finish our
shopping!” With a small amount of small talk and giggling she looked up and
starred at me and laughed still dangling her shoe. She then said, “Yep I was
right about my brother and my nylons. Yep I caught him, I was right and have the
evidence to show you! We’re both on our way over!”
To Be Continued…