Published Sex Stories / taboo-stories

Little Tommy

oioiandrea on Taboo Stories


They had been working together for a few months. Though Tommy was only 16, Vicky had a strange attraction to him. She was older, 35, been around the block in the bedroom and knew she could teach such a nieve boy a thing or two.

They made plans to have a few drinks together as friends usually do. She knew he was a lightweight, but didn't want him throwing up drunk. They played a few hands of 45s. She started getting flirty with Tommy, too see if he would bite the bait. In no time his hand was in hers and they were heading to the bedroom. Vicky told Tommy very firmly to do as she said, he ofcourse agre

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ed. She said "take off my shirt" right away he grabbed at the bottom and tried to lift it. She yelled "Stop!, unbutton it, I'm a lady, treat me with the respect I deserve." Tommy said "yes ma'am" and slowly began to unbutton the pinned striped black shirt she was wearing. He could feel his cock grow and get uncomfortable in his jeans.

Vicky's shirt slid off her shoulders to reveal a sexy leather bra with cleavedge much hotter than anything Tommy had ever seen in real life. Vicky went to the side of the bed and took out a pair of leather cuffs. Tommy felt as scared as he was excited. He asked shyly "what are you going to do with them?". Vicky simply said "shut the fuck up and give me your wrists". ofcourse Tommy agreed. She put the cuffs on him and attached him to a metal ring hanging in the doorway that Tommy had not noticed till then. She went to the side of the bed again, this time comming back with a blindfold. Vicky put it around his head covering his eyes. She asked nicely "can you see anything?" Tommy could see a very little from under the blind fold, just the floor and her feet. "no" he lied.

Tommy's cock was growing harder and harder under the weight of his pants. She liked watching him squirm trying to get his pants a little looser where he needed it. Vicky then got a pair of sissors from the night table. All Tommy could see was the sissors going towards his young belly. He tried to stay calm as she slowly slid the sissors up cutting the shirt off his hairless body.

"Are you comfortable Tommy?"

"yes ma'am" he repiled.

"Good boy".

Vicky unbuckled her belt and slid it through her belt loops, out of her pants. She wrapped the leather around both fists and in a quick motion had the belt at his throut.

"Have you ever been choked little boy?"

"Are you crazy?" he replied, "Ofcourse not"

She could smells his fear. she lusted after it.

She unwrapped the belt from her wrists, grasped it in one hand and whipped his back just once, but very hard.

"Fuck that hurt"

"Shut the fuck up"

"I don't mind a little ruff play, but you need to be carefull with me"

Tommy angered Vicky. She doesn't like being told what she could and could not do. He watched her feet as she went back to the bedside. She came back with a ballgag and stuffed it in his mouth. He wanted it, but was affraid of it at the same time. He gave little resistance, but she was still able to tighten it around his head. Now he was speachless.

Vicky stood infront of Tommy, face to blindfold. She grabbed both his nipples and began to squeeze lightly at first, harder, than harder till he started whimpering in pain. Tommy was sucking air and saliva, she giggled, She knew how saliva builds in the mouth when a ballgag is present. She went to the back of him again. She whipped him with the belt once hard, then a few more times a little lighter. She rubbed his back where the red marks were, and kissed them gently.

"Good boy"

From the back, Vicky reached around and unbuttoned Tommy's pants. She slid down the zipper, and slid down his pants with ease. He was a tighty whitey boy. She loved the sexy innocence of them. She pulled them down, just passed the cheeks to reveal his smooth flawless little bum. She smacked his ass as hard as she could with a flat open hand. The sting in her hand was sharp, but certainly not as sharp as the pain on his cheek. Tommy's muffled scream was loud, drool dripped from his forced open mouth.

Vicky pulled the pants down slowly, using both hands and running her nails down his fair skinned legs, leaving pink scratch lines the entire way down. She helped him lift his feet to take off the pants and undies. He quickly felt so very naked standing their at her mercy.

Vicky walked around Tommy a few times. Finally she stopped directly in front of him. She looked at his hardened penis, and couldn't help wanting a taste of it. She dropped to her knees and lightly started to lick his young tip. Tommy couldn't help but use his slightly off blindfold to his advantage. He watched her as she teased his cock, then finally took it all into her warm mouth. Tommy moaned a muzzeled moan of extacy. He couldn't beleive what he was watching and feeling from this beauiful older lady.

She started sucking harder and faster till Tommy felt he was almost going to cum. She looked up at his face with his cock in her mouth and to her surprise saw him peeking out the bottom of the blindfold looking back at her. Vicky got very angree, but ofcourse extramly turned on by his disobediance.

She stood up.

"You want to watch little boy?" she asked the gagged young face

He nodded yes.

She took the blindfold off him, and dropped it to the floor, she lusted his little puppy dog eyes.

"If I let you loose, do you promise to do as I say?"

Tommy nodded in agreement, excitment.

Vicky first took off the ballgag. She could see how thankfull he was for that. Next she unstrapped his hands to let him loose. Tommy felt great being cut loose. He moved in to try to kiss Vicky. Vicky leaned back and slapped Tommy square across the face. Tommy yelp like a puppy in pain. He wanted her. He needed her like he's never needed anything before.

Vicky felt excited. She felt more control than she's ever felt. This young boy is nothing but putty in her hands. She took Tommy's hands and led him to her bed.

"Have you ever tasted a woman?" She asked

"no ma'am" He replied.

Vicky bent down to remove her panties, and slowly slid her ass on the bed.

"Taste me"

Tommy moved in, unsure about what to do, He licked around till he found her clit. He licked it like a dog licking someones face. Long hard strokes. Vicky reached down and grabbed a fistfull of Tommy's hair. She held him were she wanted to be licked, then instrucked him to do it softer. She knows what she likes, and he knows he's going to learn. Tommy did smaller softer strokes. He flicked her love button with his soft deserate tounge.

Vicky grabbed his hair tighter, pulled Tommys tounge into her as she felt the pleasure inside her build. She wanted to cum so bad, but knew this amature could not do it. She at that momment, couldn't stand the feeling of his tounge in her.

"Come fuck me" She demanded.

Tommy climbed on the bed, unsure of what to do. Vicky told him to lie on his back, and he did as she climbed on his youthful body. She took his member into her moist pussy. She fucked him slow, she knew he wouldn't last long and she really wanted his first time to count. More than anything she wanted to fill her own void. It had been atleast a couple months since Vicky took a young boys life.

Vicky jumped off Tommy, and quickley moved to start sucking his boyhood again. She sucked with the same motion her pussy had on him just momments ago. She sucked harder till she felt the shaft of him start to bulge, ready to explode in her mouth.

Vicky took the entire shaft into her mouth just in time to sink her teeth deep into his cumming cock. Tommy screamed in pain. Vicky raised off of the bleeding mess rising herself to be next to Tommy. He was screaming waving his arms unsure of what to do. Vicky simpley wrapped her pretty hands around Tommy's neck and squeezed. He fought with the little life he had, untill Vicky took that little life away.

When I was 16

elainepwl on Taboo Stories

At 15 I had had an absolutely thrilling time with the owner of a local surf shop in Wildwood, NJ. My family took an annual summer vacation to Wildwood, renting a small cottage a few blocks off the boardwalk.  I had first sexual experience in Wildwood at 13. First with a boy a couple of years older than I, and then, later, with his father.  
 
The sexual experience with the boy's, dad established a life-long thirst for older men. His father had seemed to take me seriously as a female, and although he had "had his way with me" just once, the experience was so physically and psychologically pleasurable that I have spent a lifetime loving older men (I'm now 33). 
 
The next summer I had sex with the father of a girl I knew, Hol
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ly. It was wonderful, and he taught me to love my body, and to love the body of a man. He taught me much about oral pleasures, including sucking and nipping his nipples, and licking his balls and that wonderful ridge behind them he said was called "the bridge of sighs" by the Japanese.  He was the first to introduce me to anal stimulation when he expanded his pleasuring me from my clit, labia and vagina to my own tiny bridge-of-sighs, and my anus.  
 
I loved it when his tongue probed my tiny nether hole, darting in and out and sliding all around the sensitive rim.  After we showered, he allowed me to, for the first time, do the same to him, and I'll never forget how rapid his breathing became as I laved his backside from scrotum to anus.  Toward the end I jerked his rigid cock until he shot rope and rope of white, sticky sperm onto the tile wall of the shower as I tongued his sweet ass.  He let out a low, rumbling groan as he spurted his spunk, and I felt his knees buckle slightly. He was so covered in sweat afterward, that we showered again. 
 
I have always felt very powerful when giving a guy head. I know some women look on it as a form of submission to a guy, but not me. I know I am in the most powerful place a woman can be when I am pleasuring a guy orally. Truth is, he is at my mercy, even if he doesn't know it.  If you are a woman reading this you can discover my truth. Just stop sucking and licking and get up to "go to the bathroom," or whatever. You will be amazed at the desperate reaction of your playmate! 
 
Anyway, I thought I would tell you about an event that took place the summer I was 16. As I said earlier, I had been having sex each summer for the previous three years, but I abstained during the rest of the year. My mother, ever the wise woman, had figured out somehow, and I've never learned how, that I had lost my cherry when I was 13.  After we had gotten home, she had a quick girl-to-girl chat with me. She said that she "assumed" that I was sexually active at the Shore, but if I was a smart "young woman" (I really liked that!) I would protect my reputation at home. It would be "deadly" to me if I became known as an "easy" girl. I would spend my entire high school life fending off horny boys, and being hated by girls who I now counted as friends.  "So," she said, "If you are having sex while we are on vacation, please use a condom, but if you are smart, don't once we are home. At home you can be a virgin..." 
 
That was good advice, and I took it to heart.  So, I was virginal and pure at home, but a tad slutty at the Shore.  Although, I have to say that I wasn't much of a real slut, because I really didn't know how to be one of those.  But, I was a pretty fresh-faced, lean bodied young girl who loved learning about how to pleasure and be pleasured. 
 
With that said, let's visit my summer in Wildwood, NJ when I was 16.
 
This year I quickly became bored with the same old boardwalk routine, which was a gaggle of girls going one way, and a gang of boys going the other, occasionally coming together like galaxies passing through the same interstellar space; some bodies colliding, some being pealed off due to gravitational attraction, but most moving through each other with only minor distortion.
 
So, I saw a sign in the window of a small gift shop, you know, the kind of place that sells sea-shell based knick-knacks, t-shirts, cheap Chinese-made rubber sandals, etc. The needed a part-time clerk. I thought, "What the hell," and went inside. 
 
The store wasn't terribly large, and it fronted directly onto the boardwalk. I saw a woman behind the counter reading a paperback book. I wasn't a good judge of older people's ages in those days, but my reconstructed memory would put her in her early 40's.  I approached her, saying, "Hi!" all perky.
 
"Hello," she said, smiling. She seemed pleasant enough to me. She had short dirty-blond hair and pale, sort of washed out blue eyes.  She was slightly on the plump side and stood no more that 5 feet 3 inches. "Can I help you?"
 
"I'm here about the card... The job you have in the window."
 
It turned out that she and her husband owned the shop. We did the usual, but new to me then, interview. I told her I was only down for three weeks or so, which she said was better than nothing.  Next I knew, I was hired as a part-time store clerk.  She wanted me to work mornings, and that she would come in around lunch time, and then I was free to either work longer or to "run along."  I later learned that she wanted to "sleep in."
 
We spent the next hour or so going over some details, like how to work the register, where stuff was stored in the back, and so on. I was to report to work the next morning at 9:00 a.m. She said she would be there to introduce me to her husband, Joe.  Her name was Betty, so I now worked for Betty and Joe of Wildwood, NJ.
 
When I told my folks later that night, both seemed pleased. My dad said I was growing up. Clearly he didn't know of my principal summertime preoccupation with sex.  My brother acted like he couldn't care less, which I'm sure he didn't. He and I orbited in different plains in those days. He was about to start college in the Fall, so he felt that he was somehow superior to all us high school "kids."  I was pretty sure he was still a virgin.
 
The next morning I presented myself at the shop, ready to "get to work."  I dressed carefully in a pair of khaki shorts.., fairly short shorts, a white pullover blouse, simple white bra and panties.  Oh, and the ever-present flip-flops.
 
Joe was already there, sitting behind the counter reading the Press of Atlantic City newspaper with a cup of Starbucks in front of him. He appeared at first glance to be a pretty ordinary looking guy. Brown hair with just a hint of gray at the temples, slim in a gray polo shirt. Light tan complexion.  But, when he looked up and smiled at me, his face lit up!  What a smile. I felt myself melt inside.
 
"You Elaine?" he asked, and I nodded not trusting my voice.
 
"Well, come in," he said, standing, and sweeping his arm in a grand gesture. "Let's get to know one another."
 
We sat at the counter and talked for about an hour. I couldn't tell you exactly what we talked about, but I remember that he held my gaze, always looking directly into my eyes, his very light blue eyes expressive and animated.  At one point he touched the back of my hand lightly with his fingertips and I nearly swooned.
 
I was so taken with Joe that I couldn't help but act a bit flirty. I still get that way when I'm nervous, which sometimes helps me in business, but still leaves me feeling a bit flustered.  About lunchtime Joe's wife, Betty came in. She bustled about, fixing this and that before announcing that she had an appointment some place or other.  She gave Joe a peck on the cheek and me a quick glance that reminded me of how the nuns sometimes looked at me at school, and then, "poof" she was out the door and gone.
 
Joe looked at me and laughed. "Sorry for that," he said, "She's always been somewhat abrupt."
 
I just smiled and shrugged.
 
Sometime in the middle of the afternoon when the heat was at its peak and the boardwalk traffic had pretty much dried up, I moved about the small shop dusting and just sort of tidying up the place.  I went into the small store room, which wasn't much bigger than a long closet in search of a broom.  I turned when something blocked the light from the doorway.
 
Naturally, the "something" was Joe.  We stood very close together, and after a few beats he reached out one hand and placed it on my shoulder, saying, "Elaine, you are a very beautiful young woman.., do you know that?"
 
I know I blushed, but Joe probably couldn't see that in the dim light.  I said, "Er.., ah..."
 
He quickly snatched his hand away, saying, "Oh, I'm sorry, Elaine... I didn't mean to scare you."
 
My right hand followed his and before I knew it, my palm was resting on his chest. I could feel the hard muscles beneath his shirt, and, just barely, I could make out the beat of his heart.  My other hand also reached out, taking his hand in mind.  I said, having a sort of out-of-body experience, "You didn't scare me..."
 
I felt myself tremble as he bent down and placed his lips gently onto mine. At first the pressure was gentle, but soon I felt my mouth opening as his tongue slipped into mine, and I tasted him for the first time. He tasted cool and slightly of coffee, with cream and sugar. I felt my arms link around his neck as we kissed, and his hands gripped my hips lightly, his thumbs pressing slightly into the erogenous zone where my thighs met my pelvis. I pushed my groin against him, feeling his hardening member against my belly as I did.
 
He began kissing my neck at the base of my shoulders, his hands roaming over my khaki-clad ass, squeezing and kneading me, as he slipped one thigh between my legs, pressing hard against my cunt.  I could feel my heat against his leg as he ran his tongue over my neck, and I began to hump him slightly.
 
Gasping, he pulled partly away from me, and said, "Can I touch you?"  I could just make out his eyes in the gloomy store room.
 
"Yes," I whispered.
 
Joe slid his hand between the waistband of my shorts and my belly. His hand was smooth and felt wonderful against my quivering tummy. I sucked in my breath as his fingers slipped beneath the elastic of my panties, sliding over my lightly downed mons. He pushed his hand deeper, cupping my steaming pussy.  I could feel one of his large fingers pressing between my labia, pressuring my rapidly swelling pearl, and I could suddenly feel the slipperiness of my dew as it began to flow.
 
I quickly unhooked my shorts and pulled down on my zipper, and then rapidly pulled my shorts and panties down over my hips to mid-thigh.  Joe pushed with his middle finger between my damp folds, probing along my slick, pink gash until I could feel his fat finger begin to push into my vagina.
 
"Oh. Gosh," I mumbled, as I wiggled my legs to try to get my shorts off.  As I did, Joe reached down with his other hand and pushed them down to my calves. From there it was a quick move to release one leg completely.  I lifted it and rested my foot on a small carton as he began to finger me more fully.  I loved the feeling of his finger as he shoved it in, and out. In and out, and in, where he would sort of swirl it around inside me, the root of this finger pressing deliciously against my now swollen clit.
 
Before long I began to cling to his shoulders, my face against his chest as he finger-fucked me. I heard the squish, squish as he inserted his finger again and again. I could feel the void beginning to open in my center as my orgasm began to radiate outward from my womb, sliding down my limbs, numbing my fingers and sending a paralyzing jolt to my legs.  Then, BANG, it hit, and I lost all my strength as his fingers, now two, shoved deeply into my pussy. I must of cried out, because I almost always do when I cum.  But, I know I sagged against him, my pelvis trying to pull away from this hand as the almost overwhelming ecstasy bordered on pain.
 
I gripped his wrist with both hands as I alternately tried to yank his fingers from my sopping, swollen cunt, and forced myself, animal like, jerking back onto them as the spasms of pleasure and pain bolted through me. I know I must have been whimpering until.., at least, my orgasm began to subside, his fingers still buried to the top knuckle within my hungry womanhood.
 
I tasted the salty sweat on my upper lip as I opened my eyes. I could feel my cunt juices sliding down my inner thighs. "Oh, my," I said, "That was absolutely wonderful..."
 
I hadn't cum anything nearly like that since the previous summer, having only my own self to masturbate me. But, this was something even greater. I was pretty sure that I hadn't had such a blast ever before.

Suddenly, I felt a great vacancy as Joe pulled his cum-soaked fingers from within me. I felt them withdraw like a long, slippery eel, leaving me empty, wet, and cool.
 
"You are one hot thing," Joe said, looking at me in wonder. He first smelled my essence on his fingers, then licked one. "Want a taste?" he asked.
 
"Yes," I said, "Yes, I do.
 
Joe pushed the other damp finger between my lips, and I sucked it like a small penis. He fingered my mouth a few times as I tasted my salty, slightly musky self. I felt slightly woozy.  Joe must have sensed it, because he asked me if I wanted to sit down.  Before I did, he pulled up my panties and shorts, and, holding my shoulders, guided me down onto a small stepladder.
 
I took several shuddering breaths, then said softly, "That was wonderful... Incredible, actually."
 
"I'll say," Joe said, "I've never seen anyone cum like that before."
 
I could feel, rather than see Joe's eyes on me. Then he said, "Will you do me?"
 
I didn't need to be asked twice. I reached out and unbuckled his trousers, unbuttoned the top button and quickly pulled his zipper down hearing the whirring sound.  I reached and pulled his slacks and shorts down to his knees, and leaned forward from my sitting position.
 
I couldn't really see his cock well, but I grasped it with one hand, and cupped his heavy, cum-laden balls with the other.  His scrotum felt heavy in my cupped hand and his pubic hairs felt soft and silky. His organ was long and felt somewhat thinner than some of the few I had had in my short life.  I loved the feel of heat from it, and the hardness rigid under the slippery outer skin.  I ran my thumb over the crown, getting a feel for the sponginess of it, and smearing a small amount of slickness that dribbled from the slit. 
 
I leaned forward and placed my nose at the root of his cock where it sprang from his nest of hair and inhaled. I loved the smell of his maleness; a musky Oder with a light overlay of talcum powder. I felt the warmth of his body against my face, and the heat from his rigid penis radiating against my neck and jaw. 
 
I shut my eyes in pleasure as I began to rub the head of his cock over my cheeks, nose and forehead, reveling in the touch of his manhood.  I stroked him a couple of times, then let the head, just the crown, really, into my mouth; my lips wrapping it in a warm embrace, and my tongue sliding over the wonderful head. I felt his quick in-take of breath as his belly contracted when my warm mouth encased his cock head. I could taste him. His musky saltiness flooded my senses, and I could feel my tummy flutter again. He groaned deep in his chest.

I placed one hand under his scrotum, cupping his warm, full balls, and the other held his penis where it joined his body.  I leaned my head forward, slowly, slowly, taking more of his manhood into my mouth, over my tongue and then.., into my throat.

It felt magnificent. I loved feeling his cock filling my mouth, my lips wrapped tightly around his shaft, my nose buried in his pubes. I pulled back, suctioning his penis until just the head remained in my mouth, my tongue dancing over it and probing his pee hole. I could hear Joe's quick intake of breath as I played with his cock head.  I began to stroke him as I sucked and sucked on his head, my lips locked around his shaft just below the bulbous knob.

It didn't take long before I could feel his hips begin to move in the ancient rhythm, back and forth as I sucked him.  Then, I felt the rush of his sperm along the underside of his shaft just a moment before it errupted in my mouth, spraying my throat with his hot, hot, slippery sperm!  What a flood. He pulsed several times before the flood subsided, and his penis began to deflate, slipping from my lips.  In the dim light, I opened my mouth to show him the pool of his sperm, wiggling my tongue.

Then, then I swallowed his slightly salty discharge. He tasted very, very good.

Pulling me up, he kissed me, his tongue entering my mouth and slipping around sampling what was left of his cum.  I felt weak in the knees, but held onto his hips as he kissed me.

Suddenly, he pulled away, and quickly pulling his shorts up and over his wonderful cock.  "I've got to open again, just in case Betty comes back."  He turned and left me sitting on the step ladder in the store room.  With a sigh, I stood up, brushed my hair with my fingers, and walked back out into the store.
 
What a day.