Guided Masturbation Stories

Unexpected Reward

alt.sex.stories, 1999   

By now Lisa had reached the edge of the chair I was sitting in. Still
she continued onward, until that one glorious moment occurred when I felt
that pressure between my legs, directly and precisely placed where it was
needed most. I suddenly noticed that during this entire time, I had been
holding my breath in anticipation of this auspicious moment. Now that it
had finally arrived, my breath just kind of squeaked out in a slow,
wheezing kind of way. As I looked down, I saw that my crotch tightly
cradled her wide left foot. Her toes were draped over its’ head, and the
balls of her feet were firmly placed at the point where the head meets the
shaft, with the rest of her foot running down its’ length. The feeling of
sexual pleasure, although most pronounced near the tip, was absolutely and
irresistibly pervasive.

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Guided Masturbation Stories

Early memories of masturbation

alt.sex.masturbation, 1999

My earliest memory of self stimulation happened when I was around 7. I
had begun to notice my penis more, probably due to
it’s newfound tendency to announce itself by getting stiff, like it was
trying to poke itself out of my shorts, or, in cases when
I was showering, say, “Hey, look at me. Touch me. Don’t I look like
fun?” I suppose it happened more often in the shower
with the blast of the shower jet stimulating it. I don’t remember any
sexual kind of feelings from the streaming water, but it
seemed to have some effect on my penis. One day after showering, I was
toweling off. My cock was still stiff from the shower,
and brushing the soft, but coarse fabric of the towel over it made me
shiver. Not the usual kind of shiver, like, it’s cold, or
something gave me the willies. This one started like a bolt of
electricity at the tip of my dick, shot right through it, and sent
tingles all through my body.

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Guided Masturbation Stories

I Meet Toni’s Mom

from the net, circa 1995 A college student takes lessons from his girlfriend’s mother.

I meet this girl, Toni, at a party when I’m a junior in college. She’s only a junior in high school. The age-difference is a stretch, but she’s so pretty and disarming and flirtatious that I an’t resist. Her breasts are so firm and her pubic bone so compact pressing against her tight pants that I can’t think of anything all evening except making love to her. She accompanies me back to my flat, and we neck a little, but the first time I try to touch her breasts, even with her shirt on, she deflects me. I’m too aggressive, she explains. The way she was brought up, females decide everything and males are grateful for the chance to please them. I ask exactly what she means. She picks up a pad of paer and starts to sketch as she talks. She tells me to get up off the couch.

“Do you really want to know?” I say Yes.

“I learned everything from mom,” she says. “I learned how to draw and how to dominate males. Why don’t you strip and let me draw you?”

It’s that matter of fact. I’m confused, but there seems to be some sex in it somewhere, so I comply. Toni says she’ll tell me what to remove when. When each item is off, she adds, I’m to turn slowly in a complete circle so she can look me over, make a few quick sketches of what she sees. “For mom,” she says.

“What do you mean, for mom?”

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Guided Masturbation Stories

Take Your Daughter to Work Day

by Schulzie, circa 1998 A man is treated by a woman doctor as her daughter observes. Note the passing reference to “Masters and Johnson”; does that date us, or what!

“Did you feel his testes jump, honey?” Dr. Young asked her daughter.

“I’m not sure, Mom. Can we try again?”

“Again, Carl?”

Once more, Carl turned his head and coughed. His balls jumped and his dick rose just a little more.

“Well?” asked Dr. Young.

“I felt them that time, Mom. That’s interesting the way they do that.”

Just then, Courtney pointed to Carl’s dick and said, “Look, Mother. Look at Mr. Walters’ penis.”

Oh, God, she sees it, Carl thought, realizing that the young teen spied the beginnings of his erection.

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Guided Masturbation Stories

Sister-in-Law Cockteaser

alt.sex.stories, 1996

I never thought I would be writing this down for anyone to see, but then, I never had a clue as to what would happen to me only a few months ago.  You see, my sister-in-law is, what I consider, the biggest and the most cruel “Cock-Teaser” of all time!  But then, maybe I had better back up and let you decide for yourself.

I am married to a very beautiful and passionate women, we have been married for three years and she is pregnant with our first child.  My wife is great where sex is concerned, we are both into pleasing the other and have an excellent sex life.  We are both 26 years old and are both career people.  As a matter of fact, we met in college and never let each other go since. Gloria (my wife) is a para-legal and I have a BSME degree and have a very good job.

My wife has two younger sisters, Donna, who this story is about, and Cheryl.  Donna is the middle daughter and up until recently was married and lived far away from us.  But a divorce from her husband changed all of that.  The divorce took its toll on her severely, so when Gloria asked if Donna could come out and stay in Dallas with us, I had no objection.  They were always very close and my wife wanted to help her.

During her stay with us, I, of course, was always looking at her, since she was an out-right fox, and had a body that would make any man get stiff.  As a matter of fact, I think her ex is one dumb fuck for letting her go.  Anyway, during her stay, that is all it amounted to was wishful thinking and looking on my part.  She never did or said anything off-color either.

She grew to like it in Dallas and decided to get a job and stay.  After a couple of months, she moved into an apartment with another girl at her work.  Gloria and I were kind of glad to see her go, since our sex life had taken on a suppressed tone during her stay.  Gloria is very vocal during sex, and having her sister in the next bedroom bothered her.  So when Donna moved, we were happy for her and happy for our privacy back.

We frequently included Donna in our travel plans and had her and her roommate over quite often for cook-outs and things like that.  It was a nice close family relationship, and that’s as far as it went.

That is, until recently.

Gloria was in her 7th month of pregnancy when she began having a slight complication, which caused her doctor to suggest no sex, at least, no intercourse until after the baby was born. My wife was a trooper through it and gave me oral sex whenever I was horny, and I would return the favor.  But I must say, that by the 9th month, I was in need of a pussy wrapped around my cock. I never knew I would miss it so much.  I was dreading the 6 weeks after birth, but here I was with about 14 weeks to put up with.

On a Friday night, Gloria got a call from her sister, saying she was trying to get a better job, and wanted to know if I would help her with a resume.  Of course, Gloria answered for me, not that I would not have.  So the next day, Saturday, Donna would be over to work on her resume.  My wife was already planning on shopping for the baby with one of her friends and got up and let me sleep in.

At about 9:00 in the morning, I was awakened by Donna calling up the stairs to me to see if anyone was home.  I got up and went downstairs to find Donna putting on a pot of coffee in the kitchen.  I was wearing my pajama bottoms with a “T” shirt. The pajama pants had a slit in front, but it had a type of flap that prevented accidental exposure.

When the coffee was ready, Donna and I went into the living room and sat on the couch.  She was wearing a blouse and skirt, that showed off her gorgeous legs while she sat there next to me.

She was wearing a perfume that would make any man horny.  So naturally as the coffee aroused my senses, her presence started to arouse my cock.  I didn’t even realize at what point I must have become fully erect.  But at one point Donna moved over closer to me to show me a page of her resume.  Her hip bumped into mine, causing me to slightly shift enough for my erect cock to exit through the pee slit in the pajama pants. 

At the same time I became aware of the cool air around my cock head, Donna glanced down and gasped.  “Oh, MY!  What have we here?”

Now I am no John Holmes with a super cock, but I do have a respectable 7″ shaft.  I quickly reached down and pulled the pajama opening over my erection and told her I was sorry.

“No need to be sorry, I understand.  Gloria told me all about it.”

“Told you about what?”

“That you can’t have any until the baby is born.  I can help you out, you know.”

My heart went to my throat at that statement.  Was she propositioning me?  Was I going to get the pussy I had been missing?  I flinched as Donna boldly slid her hand into the pajama slit and brought out my erect cock.  Her hand felt hot and very good as she slowly stroked my cock.  I turned toward her and went to put my arms around her.

She quickly batted my arms away, and said, “NO, YOU DON’T TOUCH ME.  I’LL DO EVERYTHING.  IF YOU TOUCH ME, I’LL STOP”

Her hand felt so good, that I obeyed and relaxed, laying back to enjoy the hand job, my lovely sister-in-law was giving me.

Still holding my cock in her hand, she stood up.  “Come into the kitchen”

She led me by the cock into the kitchen, where she left me standing in the middle of the floor as she went to the cupboard.

She looked back at me and said, “Take your bottoms off and lay on your back on the floor”

Her voice was kind of authoritative, so in no time I was laying on my back in the middle of the kitchen.  After looking in a couple of more cupboards, Donna came over to where I was laying.  She had a kitchen towel and a bottle of olive oil in her hands.  She squatted down and got on her knees by my side, facing me.  This caused her skirt to ride up her thighs, and I had a clear shot of her panty-covered pussy.  My cock which was standing straight up, lurched as I clearly saw a wet spot in the crotch of her panties.  She was excited, with what she saw.     “YOU BETTER LISTEN.  IF YOU ATTEMPT TO TOUCH ME OR EVEN MOVE, I’LL GET UP AND LEAVE YOU WITH YOUR HARD-ON, UNDERSTOOD?”

I could only nod as I watched her pour some of the olive oil into her hand.  Then she wrapped her olive oil-coated hand around the head of my  cock, and began a slow downward stroke.  I moaned and my thighs jumped.

“Spread your legs and put the soles of your feet together.”

As I positioned myself like she said, she moved over between my spread legs and kept up her slow stroking.  As I looked down past her shiny hand on my hard cock, I saw the wet spot had gotten a lot bigger at her crotch.  I decided to get bold and reached for a perfectly formed tit in her blouse.

Donna immediately jumped up and stood over me, “I TOLD YOU WHAT WOULD HAPPEN.  DO YOU WANT ME TO LEAVE?”

“NO, NO, Please don’t leave. PLEEEEESE!”

“ONE MORE TIME AND I’M GONE!”

Donna once more knelt between my spread thighs, pulling her skirt even higher than before.  My cock lurched as I felt the oily hand encircle the head once more.  Then her other hand went to my balls and began rolling them in their sack as she slid her hand up and down my erection.  I was close to cumming and still wanted in her pussy soooooo bad!

“Donna, please at least unbutton your blouse for me?”

“I have a new rule for you!  The only time I want you to talk, is when you are getting close to shooting.  Any other words, and I’ll leave!”

What could I do?  Here was this gorgeous female with her oil soaked hand around my horny cock and her other soft hand driving my balls in a fever.  I announced to her that I was going to cum.

She slid her hand to the base of my cock and squeezed hard. After a few seconds of that hold, the urge to cum went away and she started up again.

“If you ever cum, without telling me first, I’ll leave!”

I wondered what the heel was with this Bitch?  But my cock had the driver’s seat at the moment, not my brain.  Donna continued the teasing motions through about 10 more announcements of an impending orgasm.  And each time she would do the same to stop it.  I was about to go nuts with the need to cum, that my balls were beginning to hurt.

Then came about my 12th announcement to her that I was going to shoot.  To my relief, her hand picked up the pace of stroking my cock.  I have never in my life felt such a violent cum as that first one.  I groaned and arched my back as I felt the first spurt rush up my cock.  As I watched it launch from the tip of my cock, I gasped in awe as the stream of thick cum shot clear over Donna’s shoulder and splashed up against the kitchen wall. Before the next spurt came, she directed my  cock back, so that it went back over my head and landed on the kitchen table.  As I looked down to observe the next spurt, I saw Donna’s legs rapidly opening and closing and heard a loud moan escape her lips.  She was cumming.

Seeing that, of course, caused another tremendous spurt, straight up and back down onto my chest.  Several shorter spurts came and then a long time of oozing down my cock and over Donna’s hand.  She kept it up until I was done and then even milked it for more.  Once satisfied that there was no more, she went to the sink and washed her hands.  And left the house!

I laid there spent for about 15 minutes before I felt strong enough to get up.

This scene has been repeated many times over since then. Basically, the same except that now she warms the oil before doing me.  And only last week, she came over with no panties on and allowed me to see her wet slit.  She never fingers it, and can cum just by squeezing her shapely thighs together.  Many a time, the heat of the moment has gotten to me and I have either tried to reach for her or talk to her.  She abruptly gets up and leaves me laying there to pump myself off.  She is a real Bitch when it comes to that.  I guess I should be thankful for the view of her pussy.

I have learned how to read her reactions as to when she will allow me a release.  When she is ready for me to cum, her breath comes in small raspy gasps, and then when I announce it, she moans and begins her thigh masturbation. ..

Guided Masturbation Stories

My Sister and Her Friend

I clearly remember the first time I masturbated. I was on an outing with my family at a lake in the northeast US. I was 10 or 11 at the time and my sister, Karen, was 16. Initially I was very upset that my friend could not come along. After all, Karen had her friend along and I was all alone. I guess I whined enough that my mother instructed my sister to let me tag along with them during the day. Karen, as i said, was 16 and blonde. I had noticed that she was the center of attention of my friends and I always liked to look at her. Her friend, Denise, had black hair and hug knockers.

All day long I noticed them laughing and giggling and whispering at each other. I did not think much about it (girls always did stupid stuff like that) except I got the weird feeling they were giggling about me. Denise especially kept on looking at me when I was in the water. I sort of liked it and sort of thought it was spooky. Anyway, after a day of picnic and swimming and boating in the lake my Karen and Denise decided to take a walk in the woods. I begged to go on the walk (anything than being with the grownups - how boring!)and whined enough that they finally consented.

We walked into the woods and up a slight hill for 30 minutes or so. Karen and Denise in front and me trying to keep up. As soon as we were out of earshot of my parents Karen started ordering me about (’You are too slow, Hurry up’, etc.) She started calling me a little wienie. Denise kept on looking at me and wanting to walk behind me on the trail. It didn’t take long before she was bossing me about too and making fun of me. Both of them were. When they did that it made me nervous but it excited me at the same time.

Finally we reached an open meadow and field that was planted in short grass. We walked out of the woods into the late afternoon sunlight. As we walked on we found an outhouse and Karen said she had to pee. I did too and was sorely tempted to hold my dick but Denise was there and I would have been embarrassed to do so. So Denise and I waited outside while Karen. All of a sudden Denise smiled at me and looked like she wanted to say something to me. Right then Karen emerged and Denise insisted that it was my turn. I was glad that it was and I went in and pulled my zipper down and took my dick out and peed and it felt REALLY good. As I was peeing I happened to glance over to my right and I saw an eye staring at me through a knot hole in the wood. It was Denise!!

I was shocked but very excited by being spied upon. I was visibly shaking as I came out of the outhouse, not knowing what to do or say. I looked at Karen and Denise but neither of them said a word as we walked on towards the woods. I wanted to say SOMETHING about what had happened when Karen suddenly stopped and turned and looked at me and said “Now listen you little worm, you will do exactly as I tell you to do and you want tell anyone”. She had such fire in her eyes and I had never seen her so determined. All I could do was stumble for words when suddenly Denise came up between Karen and I and said “No One!” as her hand went to my crotch. I moved back, shocked and confused by what happened. Karen reappeared in front of Denise and grabbed my belt. She held me as Denise pulled my hands behind my back. My heart was pounding so hard and fast that what was happening was like a dream. Karen then looked me in the eye and said “You will do what I say you little worm or I will tell Mom and Dad that you masturbate” I wasn’t really sure what “masturbate” was but i knew it was bad.

Then something happened that I will never forget. Karen unbuckled my pants and, before I knew it, pulled them down to the ground. I looked down and was amazed. She grabbed my cock and it started to get hard. i felt light headed as the blood rushed to my rising cock. Karen moved back momentarily and said “Shit” as they both stared at my rock hard cock, right therein front of them. “Fuck, its so big” I heard Denise say. I had never heard either of them talk this way before and I was in shock but terribly excited and I didn’t want it to stop.

“Touch it” Denise said. “Huh” was all I could say. “You stupid!, touch it!”. I was terribly embarrassed and hesitated until Karen said “Now you worm!” Denise released my right hand and Karen grabbed it and pulled my arm around in front of me. “Come on” she said “I’ve seen you playing with it, DO IT” (Oh My God, I thought). I reached around and touched my penis. “Stroke it!” Denise said. I started to stroke it and it felt so good. My balls were tight and I was more excited than I had ever been (little did I know that there was more to come). Somehow it was so exciting to be doing this in front of Karen and Denise. I was trembling with excitement and my cock was harder and bigger that it ever had been. Neither of them could take their eyes off of it and that made me feel real good.

“Do it, do it” Karen said and to my utter amazement she put her hand down her shorts and the next thing I knew they were on the ground. There was her pussy right in front of me and she was furiously rubbing it and moaning. I closed my eyes afraid that I would black out and when I opened them both Denise and Karen were masturbating right in front of me! They were staring at my cock all the time. Denise kept on moaning and saying “Shit” over and over. I stroked my cock harder and faster as I heard Denise moan loudly as she came (I later understood). She then walked over and grabbed my balls and said “Make it cum worm!!” I looked at Karen and she had one hand on her pussy and another under her top feeling her tit. Suddenly she screamed with orgasm and as she did I shot my cum in great gobs all over her, Denise and the ground.

We then clean up and walked back to our picnic like nothing had happened. But there were to be many other times. It was the most erotic thing that has ever happened to me.

Guided Masturbation Stories

Sheila the Great

A precocious teenage girl introduces the neighborhood to the pleasures of the hand and CFNM. by schulzie 1998

The neighborhood in which I grew up back in the Sixties was full of “good” girls who had a strong interest in sex, but didn’t do much about it because virginity was somewhat more valued then than it is today. Guys in my neighborhood might make out and get a quick feel of boobs occasionally, but that was rare; that is,until Sheila moved to our neighborhood.Sheila came from another town where the girls were a step or two ahead of the young ladies in our neighborhood. Not that Sheila was a slut or anything, but she was a bit more daring than the other girls.

Shortly after she moved in, Sheila taught me a game called “Trust Me?” Ever heard of it? I hadn’t until Sheila showed me.

One summer night, we were sitting on my front steps talking,and she put her hand on my knee and asked, “Trust me?” Not being sure what she meant, I said,”Sure. Why?” Then she moved her hand an inch or two up my leg and said, “Trust me?” Now I got it. She wanted to play games. The “Trust me” question and “Yes” answer game continued as she moved her hand closer and closer to my crotch. I had a rapidly rising hard-on, but it wasn’t a fully developed woodie yet, so I stopped her before she got to my dick.

Then it was my turn to ask: “Trust me?” She let me get past her knee before she said: “No.” Then it was her turn again. This time I let her move up until she touched the head of my dick before I said “No.” By now, I was completely hard, and couldn’t wait until the next time. When it was her turn again, she led me get about halfway up her thigh before she stopped me. I asked about this little teasing game and she told me it was something the kids back in her old neighborhood used to do. I told her it was an interesting little game. Then, we started over again. This time I let her get a feel of my whole cock in its full glory. She gave it a little squeeze, and asked: “Trust me?” I said “Yes”, and then she gave it a much harder squeeze. This went on for awhile until she was rubbing the length of my erection through my pants. Being a virgin myself, I was getting real close to shooting a load in my pants right there. Suddenly, she stopped and said it was getting late and she had to get home. She started toward her house up the street. As she did, I thought to myself,”That dirty little prick-teaser.” Then she turned around and said, “Wanna play some more tomorrow night?” Did I? All I could do was look at her and say, “Yeah!” Damn right, I did. I went inside to my bedroom and immediately jerked off.

The next night, I waited on my front steps for Sheila. It and I was afraid she wouldn’t show. But in a few minutes, there she was. She said, “Is there anyplace around here that we can go to have some privacy?” I suggested we head for the field behind the woods down the street. Off we went.

When we got there, we talked for awhile. Then she began the game again. During the whole time we played, I never got a chance to feel her pussy which was frustrating since I’d never felt one before. But she seemed to enjoy feeling my dick. We got as far as we had the night before with her rubbing my dick through my pants. Then she took a detour. She asked: “Trust me?” Of course I said, “Yes.” She then started to work her hand up towards my waist and asked:”Trust me?”

“Yes.” Her hand moved up more.

“Trust me?”

“Yes.” Her hand moved up to my belt.

“Trust me?”

“Yes.” She began to undo my belt. My heart was beating like crazy, my dick was getting harder by the second, and with each “Trust me?”, she proceeded step-by-step to undo my snap, then my zipper, and slowly made her way down my briefs until she touched my cock. To make a long story short, she began to give me an unbelievable handjob. Being young, it took me very little time to cum which I did…all over her hand. She smiled at me and asked, “You like?”

“Wow!” was all I could say for the longest time. As she wiped her cum-soaked hand on my jeans, I asked her if that was the first time she had ever done that.(Duh)

She giggled and said, “No, I’ve made lots of guys come in my old neighborhood.” Wow! Lucky guys. I tried, unsuccessfully, to get my hand on her pussy, but she wouldn’t let me. She seemed pleased just to get me off.

We played this game a few more times in the following weeks. I got a handjob, while she continued to keep my hands away from her pussy. When we first started doing this, I thought maybe the reason why she wouldn’t let me touch her was because she was having her period. But a week or two had passed, so it wasn’t that. I guess she just was into getting guys off. Or maybe she didn’t want to go farther outside. At this point I didn’t care. I could now say for sure that she wasn’t a “prick teaser.”

One day, when her parents were at work, she called me up and invited me over to her house. Cool, I thought. Indoors. Maybe I’ll get lucky and get a chance to feel her pussy, maybe more. I got over there, but she wasn’t alone. Three other girls from the neighborhood were there. Damn, I thought, looks like there wouldn’t be any games today. I was wrong. We were all in the living room talking with Sheila sitting right next to me and the other girls sitting around us. Suddenly, Sheila put her hand on my knee and said, “Trust me?”

This really caught me by total surprise. She couldn’t be serious. In front of the other girls? I didn’t say anything. I froze up.

Again, she asked: “Trust me?” I looked around the room. The other girls were watching. They seemed interested and apparently knew what Sheila was up to. Sheila looked at me, then looked at them, and said to me: “I asked you a question: TRUST ME?” She WAS serious.

All I could do was say: “Uh-huh.”

And with that, the game began. I was a bit nervous about what was going to happen. On the one hand, I was already a bit of an exhibitionist at that age and this was an exciting opportunity. On the other hand, I had never shown myself to a group of girls at one time. These were girls that I had known and grown up with for several years, fantisized about, had made out with, and now here was a chance they were going to willingly look at my dick. My HARD dick (I hoped). It didn’t take long to get through all the preliminary “Trust Me” questions until Sheila had my pants undone and was ready to reach into my underwear. At this point, Sheila looked at the girls who leaned forward for a closer look,then looked me right in the eyes and said, very slowly, “Trust me?”

I nodded, my heart racing, my chest tight, and then…she reached in and pulled out my cock, exposing me completely to the room of girls. I never was so excited in my life. The girls had a whole series of different reactions as soon as they saw my hard cock for the first time. It must have been the first time they had seen a penis, or at least a teenaged boy’s penis, and certainly an erect penis. Their eyes widened, their mouths dropped open a little bit. I heard at least one or two tiny gasps, a “wow”, eyes gawking at my dick, then turning to look at each other, giggles, then more stares at my dick.

Jesus! I couldn’t get over this. It was overwhelming. The blood was rushing to my head as all these girls I knew were staring at my hard-on all the time while Sheila was gripping it tightly, shaking it at them. Sheila began to stroke my dick in front of the girls. Oh my God, I thought. She’s gonna make me cum right in front of them. I was so fucking hard by that time I knew it wouldn’t take long. I wanted to cum in the worst way, yet I wanted this moment to linger as long as possible.

The girls were continuing to react as they watched Sheila jerking me off. They continued gawking at my dick, watching Sheila’s hand rubbing the length of my dick, watching my reactions to the handjob. It was more than I could take. I shot all over my shirt and Sheila’s hand and arm. The girls were taken aback, I think.

I suspect they were not sure exactly what they expected to see. They looked at my dick shooting cum, they looked at my face, they looked at the cum. I was breathing as heavily as if I was running the mile, moaning uncontrollably as Sheila finished me off. Afterwords, I sat back on the sofa exhausted, a little embarassed to have them watch as the cum began to dribble down my cock as it began to shrink. The girls were murmuring and whispering among themselves, so I excused myself and went to the bathroom to clean up.

While I was in the bathroom, I began to catch on to what the little game was all about. I heard Sheila tell the girls, “See, that’s all you’ve got to do. If you make them cum, they’re happy, you don’t have to go all the way with them, and they’ll do just about anything you want them to do.”

It wasn’t long before Sheila’s little lesson seemed to have an effect on the whole neighborhood. There were a lot of us guys geting jerked off that summer.

Wherever you are, Sheila, thanks a lot.

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

“Guided” masturbation stories are fictional fantasies about males masturbating in the presence of, guided by, or masturbated by females. They are posted under the category

http://onania.org/asm/archives/category/stories/guided-stories

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Guided Masturbation Stories

Diddlin’    by Mr. E, 1998

I was about 12 or 13 years old and in my neighborhood we were all very friendly. The boys and girls would play together. We’d play war, cops and robbers, and even set up house together (to satisfy the wants of the girls), “marrying” each other, etc. This set up some low level sexual encounters such as kissing, petting and some fingering — but always one-on-one.

One time, we had set up a “house” where I was the “son” of an older girl (she was about 14, and 1 or 2 year’s difference is quite a lot for young people) while the other “girls” were my “sisters.”

Well, it so happened that the older girl wanted to pretend to punish me and had me sit in the corner, etc. Then she wanted to spank me over her knee. I protested mildly but the other girls were cheering her on. It started out good-naturedly at first, but then she started doing it harder and harder.

“Hey!” I said. But the other girls said to take my pants down. While a couple of them pinned my arms, my trousers were unbuttoned, unzipped and taken down below my behind.

It was at this point that I started to get turned on. I was protesting with my mouth, but my “little head” was doing all the thinking at this point. It had acquired a life of its own and had become hard as a rock. Now a couple of these girls had already seen — and even felt — my penis while we were fooling around. But this was different. They were all here at the same time, and they all had their clothes on.

Anyway, the punishment stopped and I put on a show that I didn’t like what they had done, etc.

Later, the older girl got me alone in her bedroom and said “I know you got a boner when we had your pants down. Did you get turned on?” Well, it’s impossible for a functioning male to hide arousal, so I admitted to her I got really turned on.

“You know,” she said, “I’ve heard that it’s bad for a boy to get turned on and not be able to spurt. It’s called ‘prick tease.’”

I didn’t correct her use of the term because at this point my head was swimming in an air of unreality. I couldn’t believe this older girl was discussing sex in front of me.

“Undo your pants,” she said. “I’ll make you spurt off so you don’t get ‘prick tease.’”

I protested automatically but it was half-hearted. She insisted. “Take your thing out and let me do it to you or I’ll give you a real spanking and I’ll tell the other girls!”

This was so embarassing. I was “showing” mine but she wasn’t going to show hers. But I was also aroused to the point that I was not thinking rationally anymore.

I unbuttoned and unzipped my jeans and took my now rock-hard cock out. Precum was dripping off the end. She was fascinated by it. I guess she had heard about this from other girls but had never seen one up close. She pulled my pants down around my knees, encircled my cock with her fist and began jerking me off.

I started to reach to feel her breasts, but she slapped my hand away and said, “Don’t touch!” Then she started jerking me again.

“Oh, you’re such a naughty boy to get a such a big boner in front of me. Are you going to spurt for me?”

Then, with her free hand, she began administering swats. “Spurt for me!” she commanded.

And I did. Jets and jets of cum spewed out, all over her hands, arms and even onto her lap and the carpet. I think it’s the most I’ve ever cum in my whole life.

She didn’t complain or anything about getting messed up. All she said was “Gosh, that was fast.”

Yes it was.

– Mr. E