Onania . Org/asm

Guided Masturbation Stories

Gert’s Stockings

alt.sex.stories, 1996

Excerpt from a dead man’s sexual diary, purchased at an estate sale–the late Bill W. Childhood Memories of Gert’s Stockings and Garters It is August, 1955. I am 12 and on vacation with my parents and another couple at a lake cottage in northern Wisconsin. I am in the only private place in the tiny cottage–the bathroom–jerking off with the door locked–or so I think.

My bloated young prick sticks rigidly out of my lap as I sit on the toilet, massaging my exquisitely sensitive foreskin, savoring the itchy, tingly feeling radiating through my balls. My ass twitches and squirms on the toilet seat as my newly discovered pastime causes muscles and nerves to twitch involuntarily in my crotch and legs. I stare at my hand in its vertical dance, wondering dazedly that I can give myself so much pleasure. The feeling is so good, yet at the same time somehow dirty and lewd, which makes it all the better.

My heart beats wildly in my young chest. Everyone has warned me against this ‘dirty’ pastime, but surely they can’t know how good it feels for me and me alone. I abandon moralizing, and relinquish myself to the throes of evil.

My balls are tingling mightily, and there is a swirling feeling in them as though my cum was boiling, ready to erupt like Vesuvius. I don’t want it to end, yet I can’t slow the steady increase of my hand strokes. The practical side of me tells me to slow down–to ease up and enjoy the feeling for a bit longer. But my raging glands cannot be denied.

What to do? I am gasping like a fish out of water, my pulse thundering in my temples. I spread my legs wide and slump farther down on the toilet seat, my chin resting on my chest, my gaze fixed on my bloated, quivering prick. A tremendous feeling of power sweeps over me. In everyday life, I am a skinny little kid who gets pushed around by my bigger friends and forbidden from doing almost everything by my parents. But here and now, I am the master–king of the world. I have a huge sensitive prick for my age that does whatever I bid it to do. For the moment, I need nothing else.

The thoughts prod me to the verge of orgasm. I look around hurriedly for something to catch my load. My mother’s nylons are draped over the side of the tub. I reach over and pick them up with my left hand while my right continues caressing my quivering cock. They are the stretch type and harsh to the touch. I drop them. I deserve something smoother. I see another pair draped on the tub. They must belong to Gert. She and her husband are good friends of my parents. I lean over and pick up the stockings. Oh! They are exquisitely soft and silky and almost slip from my hands like quicksilver. Oh, God! These are SO sexy, I’ve GOT to just see how they feel around my prick. They are coffee colored, with seams and dark tops and heels. I can smell her perfume in them! Just for a second–before I come–I’ll wrap them around my prick! I’ll take them away in time.

Trembling, I wrap the perfumed nylons around my bouncing dick, and the novelty of the feeling almost makes me lose everything right there. The sensation on my foreskin is like fine velvet. The mental stimulation–knowing that these were recently gartered up Gert’s shapely legs–is overwhelming. I beat my prick unmercifully through the gossamer wrapping. Only the dark purple head emerges from the wispy fabric, wet with my pre-emissions.

My whole being is centered between my legs. I’d sell my soul to the devil for just another minute of these exquisite sensations. My hips are twitching of their own volition, in time with my hand, as though trying to force me to a climax. I am shamelessly lost in lust, and begin groaning out loud, knowing that the adults are all at the tavern down the road, and not particularly caring who hears. I mumble deliriously about legs and tits and stockings and garters and pussy and keep picturing these stockings gartered tautly up Gert’s legs.

I lay my head back on the toilet tank and arch my hips upward, trying to eke out yet another iota of sensation before I lose my load. The silken wrapping is doing the trick for me. I yank viciously on my prick, forcing the orgasm up to a peak. My mind battles with my glands. I’ve got to take the nylons away, or they’ll be ruined, yet I can’t bring myself to do it. Just another couple of strokes and I’ll pull the nylons off. They come and go. Fuck the nylons, I decide, this is too good to stop. Thoughts race through my lust crazed mind. “I’ll clean them off! You can’t, you dumb shit! Maybe she won’t notice! They’ll dry fast! You’re crazy! Oh, God–she’ll tell my Mom when she finds them! Take them away–take them away before its too—-.”

Then it happens. “Oh Christ–Oh! Oh! I’m going–it’s going to c–it never felt this good.” The conflict makes it better. My hand is a blur. “Oh my God in heaven I’m going to come in her stockings!” The door opens! Gert is standing there, looking at me in surprise. She steps in quickly, closing the door quickly behind her. She’s an aristocratic looking woman about 45, with dark hair done up in an elegant twist and sparkling gray eyes. She has firm tits that bulge under her white silk blouse, and beautiful shapely legs, clad in suntan colored nylons with black seams, accented with black pencil thin high heels and a black pleated skirt that comes just below her knees. She is very proper and correct and wears stockings and heels almost all of the time, even when other women in the group are ‘dressed down’.

I look up at her dumbly, in the incipient stages of my crisis. The shock of seeing her has frozen it at its peak, and I know that if I don’t do something right away, it will waste away. I’m in trouble already, so what I’m about to do can’t get me in any deeper.

My hand doubles its speed in an effort to bring up my load before she can call my mom. Having her watching somehow makes it feel all the more perverse, and I look up at her, expecting a slap at any moment. As I begin to enter the last stage, and I feel the first drops leaking from my prostate, a lewd desire grips me. I reach for the hem of her skirt and jerk it up, revealing her legs, never missing a stroke. She slaps my hand away and tells me to behave myself. Then, shockingly, she reaches for her hem and holds it waist high allowing me to drink in the visual feast provided by her milky white thighs overflowing the fantastically stretched stocking tops held tautly in place by sturdy beige garter straps of her panty girdle.

I start to come from the visual stimulation of her legs and bulging hairy bush visible through the front of her transparent beige panties. She steps closer to me, hands on her hips holding up the front of her skirt. I’m in shock. She smiles down at me as she steps next to me, putting my nose just inches from her right stocking top.

My senses reel. I feel small and vulnerable, yet as I’m enveloped by her perfume and just a hint of her musky cunt, I stare in fascination at this personification of all of my boyhood fantasizes–girdle, stockings, garters and thinly veiled pussy!

She calls my name, and I look up at her quirky smile as she stands with her hands on her hips, and winks at me. “Go ahead,” she says gently, “I won’t tell your mom and dad. Finish. That’s not bad. All boys do that. My son did that all the time when he was your age and it didn’t hurt him.” My hand jerks mindlessly as I cross the line and pop my cork.

I groan in ecstasy, close my eyes and throw my head back as the sperm begins the one way trip from which there is no return. My hand is knocked away from my prick. My eyes fly open in time to see my wet dream wrap her red taloned fingers around my insanely convulsing prick, rubbing the nylon up and down with just the right amount of pressure, her thumb flicking the opening at the tip. I shoot again and again. My load spurts a foot into the air a drops back onto the nylons encasing my prick. I do what I usually do with my pinup magazine girls, only the stimulation is a hundredfold better–I look at her face–her tits–her legs–her garters–then back to her face, trying to drink in as much stimulation as I can with the hope of keeping the orgasm going forever!

She watches my prick intently, clinically, milking it with her talented hand, tugging just hard enough to stretch the cords and tendons between my legs to a pleasureable extreme and cause my ass to lift off the seat to force even more contact. I start coming all over again, spurred on the the emotionless way she’s manipulating me reproductive system. She points my spurting organ at her legs and a large glob of cum splatters just below the stocking top of her left nylon, and slimes down her shiny stockings in a ropy string. Her other hand grips my shoulder, both comforting and exciting me at the same time. “That’s a good boy,” she says, “shoot it all, don’t be shy, I know what you like. It’s not bad, no matter what your mother tells you.” I babble like an idiot as my ejaculatory convulsions lessen yet continue, each squirt giving me indescribable pleasure. She smiles at me with twinkling, hot eyes, and I almost pass out from the pleasure that causes between my legs.

Her hand is a mess of white goo. The nylons around my prick are soaked in sperm–ruined, I think in horror. My body goes limp, and I almost pass out. The after tingle is terrific and almost as strong as the orgasm. She carefully wipes off her stockings and hand with a wash cloth as she comments on the size of my load for a boy. Again, she smiles and winks at me as though we have a little secret–and now we do!

She tells me to save the nylons as a souvenir–and says they can be washed easily with soap. I’m still semi-hard and tingling. As she turns toward the door, she stops to check her seams. I boldly lift the back of her skirt for a rear view figuring I have nothing to lose. She stands patiently. Emboldened by her acquiescence, I left my hand roam over nylon and skin, then pull her panties aside and duck my head for a quick look at her pussy. I almost stick my nose up her ass and the sight and smell causes me to start jerking off again, my cock rock hard and tingling. She turns slightly and tries to push me away.

“Not now. I have to go back or they’ll miss me. We’ll do it again.” Crazed by lust I slip to the floor and bury my nose in her pussy from behind. “Oh, please, Gert–let me just do this for a minute. I’m almost there again.”

That’s a lie, but I whack my cock unmercifully figuring that if I can buy time by lying I’ll get off again quickly, and when she says “OK, but just for a minute. If you don’t come by then, I’ll have to go” I feel that evil tingle between my legs begin. It feels just like a wet dream–much better than when you’re awake and I come as though in a dream, inhaling deeply of her womanly, slightly gamy scent as my glands empty themselves for the third time in a couple of minutes, with a few weak squirts of watery sperm. After a moment, she pulls gently away and tells me there’s plenty of time for more of the same–and better. Then, as if to seal the promise, she turns around tipsily and leans over and gives me a deep tongue kiss and squeezes my cock gently with her red taloned hand. I can taste alcohol on her breath and it is strangely sexy. I quickly put my hand up her skirt for one more feel of her stocking tops and garters, but she straightens up, smiles and winks and leaves quickly.

In a few moments, I hear her talking to my parents and her husband outside the cabin about going out for the evening. She tells them that no, she hasn’t seen me, that I must be down at the lake with the other kids. I relax. She’s for real. I go back to jerking off, this time with fresh reality to bring me off instead of boyish fantasies. When I come again, this time I imagine that my cock is sliding between her stocking tops and the silky nylon and warmth of her skin make it feel heavenly. In my feverish imagination I decide that the next time she lets me do something, I will try to do that.

Unfortunately, that never happens. From that time on, she keeps up her flirty little winking whenever I see her and sometimes asks me if I’m “behaving” myself, but never allows me any more liberties. When I try she gently tells me to “behave”, although she continues to give me ample opportunities to look up her skirt “accidentally”, but never acknowledges our little secret moment again.

She remains the object of my jerkoff fantasies well into my late teens, even after I find a girlfriend who allows me to secretly recreate the scene over and over again, never suspecting that my fantasy actually happened. She even pretends like she’s older and talks to me in the same teasing, condescending manner that Gert did. I anoint many a pair of her stockings with my huge loads while she plays with herself and scolds me for being a nasty boy, but while it is good, it is never quite as intense as the real thing with Gert.

END