My Dingaling - Cover

My Dingaling

Copyright© 2005 by Jack Spratt

Chapter 1

Erotica Sex Story: Chapter 1 - Tom continued his enlightenment concerning the wonders of opposite sex. You will be happy to learn how he managed to get out of mess he found himself in at the end of "My Dingaling II" Enjoy!!

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Consensual   Fiction   Incest  

Very early in my awareness development, my young interest focused on the sensitive protrusion between my chubby legs. I can recall touching and massaging my little cock at the age of four or five. However, my mother and my aunts were always quick to point out to anyone who would listen, that my playing started when I was a baby. Whenever one of them changed my diaper, as soon as it was removed, my small hand found my source of continuous joy.

At the time, I had no idea why it was happening, but obviously it did feel good. Mom, much to my embarrassment, points out that my stub at the age of three would actually get hard as a result of my continuous manipulations. In the bath tub when other babies were playing with rubber duckies, I was enjoying my penis.

At the age of seven, not realizing the meaning of masturbation, I had my first climax. The feeling scared the shit out of me. I was sure that something had broken; hell I even used a mirror to inspect my jewels to make sure nothing fell off. As with all boys, the feeling derived from the first experience and my natural curiosity had me try it again. Realizing nothing serious had happened, it became a daily ritual, sometimes three or four times.

My name is Tom Bates, at the age of fifteen; my height of five foot eight made me stand out among my peers. Like most young boys of my age, my friends were male; girls had been the blight to mankind. However, over the past few weeks while masturbating, a few of my sister Jayden’s friends for some unknown reason now seem to appear in my imagination and they didn’t seem as revolting as they did a few months ago.

A strange awareness happened when Bree was around; a tingling sensation had my cock extending at the most inopportune times. Bree was a young redhead with noticeable sprouts on her chest. What did me in was her smile that brightened up the room when she looked at me.

With my skills masturbating honed to perfection, my duty was to educate the masses about the joys of pumping cock. At this age boys liked to compare the size of their willies. In all contests I had won hands down. My early manipulations must have had accelerated the growth of my hormones because I out-ranked my friends by an inch, a very sizable difference and something to be proud of. Of course, the fact that I was the only one with a foreskin made my cock the centre of attention.

As school had just ended for the summer, my time was spent playing various games of ball with my friends, then going to the pool to cool off. Usually after the pool, a group of us would hang out together talking about the important things like who could wack off more in an hour. Like all boys, everyone boasted ridiculous numbers, hell with all my experience my record was only four times in an hour and I was not that sure about the last one but it sure felt good.

Today my best friend Frank challenged the group to a wack off marathon; the event was to take place tomorrow and instead of playing ball we would meet at the pool and ride to Marion Woods. There was a small spring fed pond in the middle of it; swimming was great if you could stand the spring fed cold water. Just off the adjacent path there was a small area surrounded with trees and heavy underbrush. It would provide the privacy needed for this very important social event. The news of the challenge spread like wildfire. It seemed that Frank had challenged all the guys that played ball. All participants were to bring a lunch as it would be a very long day.

Mom never questioned me about the lunch; she was happy to see me outside enjoying the summer weather rather than watching television or using the computer. It took a lot of willpower not to masturbate tonight, instead I settled for a few soft rubs that did feel so good. My morning boner was very embarrassing, thank goodness Mom didn’t notice, but my sister Jayden did, she pointed and giggled.

Arriving at the pool, it was surprising to see eight other guys ready to take up Frank’s challenge. It took twenty minutes to reach the edge of Marion Woods; we could ride most of the way using the path, but to get to the clearing we had to push our bikes through some heavy underbrush. Finally, at the site, we all stashed our lunches under a tree near the water in an attempt to keep them cool. The sun was up and we could feel the heat. Now, all nine of us were standing, looking at each other, most with silly grins on our faces. Frank the challenger spoke.

“This challenge is to find out who can jerk off the most times in an hour. We should all get undressed and stand in a circle. Jimmy, did you wear your watch?”

“Yeah, it is right here.”

Jimmy was pointing to his arm where the watch he got on his twelfth birthday sparkled in the sunlight.

“Ok, you can be the official timer. Since there are nine of us, we can have three groups. Does everybody agree?”

There was a chorus of agreement. But still we stood looking stupid.

“Okay, let’s all get naked.”

All looked around for some place to pile our clothing; in no time, all the low bushes were covered with our clothing. Not surprisingly, we were all sporting hardons of various sizes, each of us sizing up the other. My six and a half inches surpassed all others, a few guys seemed to admire my size and a few might even be jealous. One seemed particularly interested, Andy Greenspan, a boy that lived a couple of houses from me. His three inches plus was dwarfed by mine. It was a bit embarrassing, his curiosity had my tool pulsing.

Frank took the lead again and picked the groups of three, putting Andy and me with him. Because of my size he wanted to beat me. The ground rules were the winners of each group would wack off after a swim and a lunch to find a winner. My thoughts were to get started as my need to masturbate was urgent since not doing it last night or this morning. The first one was going to feel so good.

Andy was still looking at me or rather my cock, the head was pushing its way out of the foreskin as I pulled my hand back, my balls were hanging proud under my shaft, and all was fascinating to Andy. Hell, if he wanted to look let him. Spreading my legs gave him a better view. A small smile crossed his face then a tinge of a blush.

“Okay Jimmy, what time is it?”

“One minute to ten.”

“Yell when it is ten, everybody stops at eleven, is everybody ready?”

All grasped their engorged tools and nodded yes. All eyes were on Jimmy who was staring at his watch.

“Go.”

Closing my eyes, I enjoyed the feeling of my hand gliding up and down the hard shaft; in seconds my desired relief was satisfied, as three long strings of cum ejaculated, just missing Andy and hitting the ground beside him. Looking at Frank, I saw he was still pumping. Andy’s eyes were like saucers as he stared at a blob of cream dripping off the end of my tool; his watching me as I played with my cock urged it to get hard for my second round. He was licking his lips as he pumped and stared at me. Frank gave a blast of pent-up air as he came.

“Dam it Tom, my plan was to beat you this time.”

He was coaxing his tool to get hard, spitting on his hands to make them slide better, once up he was beating his meat with gusto. Now hard, I followed his lead. Andy was still trying to get his first cum. Frank came again while I was very close, finally warm cream was emitted, but in a much smaller volume then the first. Andy was still pumping his monkey with no results, but the smile on his face indicated he was enjoying himself.

As it turned out Frank did win, he was able to cum five times to my four, poor Andy only managed to cum twice. The winners were congratulating each other and boosting that they would be today’s final winners. After a very cooling dip in the pond we grabbed our lunches. Andy followed me to a fallen tree we used as a bench. My hero was all shrived up due to the cold water; Andy’s had nearly disappeared.

“I wish I was a big as you Tom, hell I have nothing compared to the rest of the guys.”

“You are smaller because your body is the smallest, it will grow with you. As long as you enjoy masturbating, that is all that matters.”

“I never seen so much cream squirt as when you came, with me it is a little drop.”

“I have been doing it a lot longer then you.”

This discussion caused my cock to grow, awaking from its cold shock and growing to its full glory; my balls had recovered as well they were filled with blood and were now hanging proudly between my legs. Andy continued to watch, his eyes like saucers. He was totally smitten with my size. It made me feel a bit sorry for him.

“It sure is a beauty Tom. I like the way your foreskin goes back when you get big. My parents had mine removed.”

His little thumb sized cock head was just noticeable as he sat with his legs spread. Andy was small. I couldn’t help but wonder why he was so interested.

The final wack-off was about to begin, the three were in a circle, the others watched.

“Are you ready Jimmy?”

Jimmy looked at his watch; put his left arm in the air then sliced downward, the pumping had begun. As the balance of us watched, we were jerking off as well except Andy who was still fascinated with my cock. When I did shoot my cream he actually caught it in his hand then studied it for the longest time. Hell, he even tasted it.

When the competition was complete, Frank was declared the winner. In the two hours he actually jerked off nine times, his closest competitor only seven; he was the winner of the Marion Woods first ‘Jerk Off Challenge’. After dressing, we gathered our bikes and rode home. Andy stuck to me like glue. Saying good-bye to the group with a promise to play ball tomorrow, Andy and I rode down our street.

“You really taste good Tom, I have tasted mine but yours is better.”

“Never tried it myself, what does it taste like?”

“Humm, a bit salty but nice.”

As Andy and I rode home, I couldn’t help but wonder what was going through his mind. Strolling into the kitchen, Mom told me the lawn needed mowing and that dinner would be ready in two hours, it gave me more than enough time. The heat of the day was in full swing. Bree, sunbathing with my sister, glanced over my way every time I made a pass, she looked up and smiled. Her soft pink bikini was tight between her legs giving me a view of the mystery sandwiched between them. Finally the damn lawn was finished. After a shower, my bed looked inviting as it had been a long tiring day, there was a good twenty minutes before Dad got home.

As I lay pumping, for some reason the vision of Bree laying stretched out made me extremely hard even after the activity earlier today, then the thoughts of Andy filled my mind, him actually licking my cream and liking it, curious.


“Tom, are you coming down for dinner? This is the third time I have called you.”

After cumming, I must have had fallen asleep, it was a good thing Mom or Sis hadn’t looked in, as my hand was still wrapped around my flagellant tool. My sister and Bree were at the table; even after recently masturbating, the tingle was returning. She was now wearing a narrow white tube top clinging to her budding breasts, nipples pointing proudly. She and Jayden were nearly fifteen, now looking at Jayden I actually noticed her breasts, her nipples were in fact longer than Bree’s. Shit, that was something I had been looking at but never noticed Jayden’s buds, more tingling not only in my cock but my balls as well.

The seating arrangements had me sitting on Bree’s left, with Jayden on her right. During dinner, a wonderful scent hit me, it was of some sort of floral design. Then I realized it had to be Bree, she and Jayden were wearing perfume. Sitting this close to Bree and glancing at her budding nipples had me wired for sound. What the hell was happening to me? The girls had been in my face for what seemed like years, now for some reason they had me trembling, maybe I was sick! Could it be the heat?

“Mom, would you excuse me please?”

“Are you done?”

“Yes, Mom.”

“I just want to let you know Bree will be staying over for a few days, her mom and dad are gone to a convention, so make sure you don’t embarrass yourself, keep the bathroom door locked.”

A feeling of a blush ran over my body, both Bree and Jayden had big knowing smiles on their faces and their eyes were on my growing bulge. Quickly, I was upstairs, into the bathroom, thus avoiding any more embarrassing situations. Dropping my shorts, I grabbed my cock and exploded in a few strokes. The volume of thick creamy cum surprised me considering all the times I had cum today, since all I had been doing most of the day was beating my meat. Visions of Bree’s smile flashed through my mind as I came with gusto. Flushing the toilet, then washing my hands, I nearly crashed into Bree in the doorway. Our bodies hit, I was sure her nipples left an indentation on my lower chest.

“I am sorry.”

“No it is my fault; I shouldn’t have been standing so close to the door.”

So close to the door, was she listening at me grunting and groaning during my masturbating while thinking of her? A very serious uncontrollable blush filled my face and gave her reason for a very knowing smile. The nymph had been listening.

Over the next two days it seemed like everywhere I went in the house, when I turned around Bree was there; it had got to the point that I was looking for her, wanting her to be near me. What the hell was happening to me? Numerous times, the view down her blouse showed me the mysteries of her budding bosom, her nipples were breathtaking. She hadn’t got much, but to me it was like splitting the atom, everything was new. This was so confusing. Hell, even Jayden was looking good and had me wondering things that shouldn’t be. Something had to be wrong with me!

Even though nothing physical happened during Bree’s visit something did occur, I actually missed her hanging around after she left.

Riding to the park later in the week, Andy caught up to me.

“Hi Tom, haven’t seen you since the Marion Woods, have you been sick?”

“No, just bumming around the house, Mom had a few things for me to do.”

The last thing he needed to know was my apparent change in attitude towards girls. The rest of the guys would tease the hell out of me. Andy looked deep in thought.

“My mom does the same to me. Tom, can I ask you a question?”

“Sure.”

“Promise never to tell the guys or laugh?”

“I promise.”

Something was really bothering Andy, he was usually never serious about anything. He seemed to be trembling. Then he asked me nearly in a whisper.

“Can just you and me jerk off together, I love watching you cum.”

Andy wouldn’t hurt a fly and because of his size and demeanor had been the brunt of many jokes which he took in stride. Sometimes, I did feel sorry for him.

“What did you have in mind?”

“We could go to the tree house.”

Several years ago Andy’s uncle built he and his sister a tree house in the back of their property. Hell, it could be classified as a small house. I had been there a couple of times; it was large enough to stand in. Since there was nothing pressing and since masturbating was my passion, we turned and headed to Andy’s house.

Riding to the back yard, I saw Janna, Andy’s sister and three of her friends were in the pool. They were all wearing two piece bathing outfits; the wet suits were molded to their young bodies. My new appreciation for girls kicked in quickly studying all their chests for protrusions. All were very interesting and varying in size. Janna waved at us and then locked her stare to me. Her wet blond hair shone in the sun; there was an immediate blood rush to my cock. My sheepish wave got a giggle from her.

Andy rushed up the tree house ladder with me behind him. Once inside he pulled up the rope ladder, put it in a box and closed the trap door. There was a large sofa like bench running along the windowless wall, it was padded and covered with a number of throw blankets, there had to be six different colored pillows lining it as well. The single window overlooked the pool, looking out again my eyes locked on Janna. How quickly my attitude had changed concerning girls.

“It is completely private with the trap door locked. The window is high enough that we can take off our shorts and no one will have a clue of what we are doing. There is even a small pail and some tissues so we don’t make a mess. Janna and the girls often come up here and she would likely notice and tell.”

Interestingly, looking at the bench all I could think of was seeing Janna stretched out naked, what an imagination. Do they come up here to masturbate? That would be something worth learning about. My hardon was ready for action.

“Tom, take off your shorts.”

Andy was only wearing his T-shirt, rubbing his stub. Following suit, there was no need for me to rub mine as it was in full bloom. Rolling back the foreskin exposed the head and the very discernible slit seeping precum. Andy was aghast. As I stroked; my attention kept going to the view at the pool, especially Janna who was now lying on her back, legs spread wide looking up at me. For some reason the view was the source of desire that travelled straight to my cock.

While my interest was on Janna, Andy was taking in all of my equipment in great detail. Looking down, he seemed to be savoring the view as he beat his short but hard stub. Looking up at me, he smiled.

“Tom, I know this is going to sound stupid, but can it touch it?”

At the time it sounded like an odd request, but later on it clarified. Not really thinking about what the ramifications could be, my first desire was to enjoy the view Janna was providing me. In my mind her show was for my personal pleasure. Removing my hand from my aching shaft, Andy’s warm hand took its place. It actually felt good having someone else do the stroking, really exciting. Janna had raised her knees and had her legs spread wide. The strain on her bikini bottoms had them molded to her pubes; my interest in the female form was new and this view had me trembling. All I could see was two sizable mounds with a deep cleft between them. This was something we guys always talk about; today it actually had meaning for me. Janna saw me staring and then glanced towards the other girls. All were laying on their tummies their heads to the side not looking towards Janna. She looked me in the eye and then her hand slowly glided down her tummy and slipped into her bottoms. Hell that action nearly made me cum in Andy’s hand. Her finger movements were displayed on the cloth of her bathing suit, an up and down motion. She was masturbating for me. I had the urge to start pumping with my hips when the shock of my life happened. My cock was engulfed by a warm moist mouth; Andy had taken the head of my cock into his warm and wet mouth and was sucking me. The feeling was wild but embarrassing; my eyes were on him then his sister who was now vigorously fingering herself, eyes closed her hips raised.

She stiffened and came, opened her eyes and looked towards me smiling, then slipped her hand out of her bottoms and made a big production putting her fingers in her mouth and sucking each digit, just at the same time my surge of cum was plowing deep into her brother’s willing throat. He had given me my first blowjob. Not losing a beat Andy hung onto my cock and extracted every drop. It was a good thing my hand was on the window sill to support myself or I would have collapsed. Andy gently squeezed my balls while he continued to suck. What a feeling.

“Andy, what did you do?”

“Something I wanted to do since watching you in Marion Woods, you aren’t going to tell the guys are you?”

“Of course not.”

After letting him suck me dry and enjoying the wonderful feeling it created while watching his sister finger herself, telling on him was the last thing on my mind. All I could think of was seeing more of Janna. As the result of the blowjob I had never felt so exhausted. Usually after masturbating and within moments my prick started to get hard, not today, it was still hanging loosely between my legs. Andy was caressing it and rolling the foreskin back and forth over the head, but it wasn’t ridged enough to hold it back. Every now and then Andy’s tongue flicked out to remove a drop of clear liquid seeping out of the slit.

“Will you let me do it again, it is beautiful.”

He was still on his knees admiring my apparatus and hefting my balls. If he wanted to suck my cock, the least that I could do was accommodate him. Besides, visiting with Andy would give me a chance to see Janna again.

“If you like we can come here after our ball game tomorrow.”

“I would like that, I don’t think Janna and her friends will be using the tree house, if they are we can use the pool.”

My concerned look as to what he was suggesting had him laugh.

“We can swim, I don’t mean to suck it in the pool, but at least I can play with your cock. I really like the feel of it.”

Arrangements were made for tomorrow. As we climbed down the ladder, Janna walked towards us. We were eye to eye.

“Hi Tom, what were you and Andy doing in the tree house?”

“Janna, it is none of your business what we were doing. Tom, just ignore her.”

The feeling of exhilaration ran through me, just looking at her, the way her hips were curved, her bikini showing what had to be her beautiful pussy, something that had never interested me before, but now for some reason had become a priority in my life. What was like to see and touch what was between Jenna’s legs?

“Actually, we just wanted to rest, and with you and your friends at the pool we thought the tree house was a good place. I noticed you enjoying yourself.”

Touché, her face turned a wonderful color of crimson, her nipples were noticeably harder, and then she bounced back.

“Yes, I always enjoy myself.”

She accented the word ‘myself‘, so I knew exactly what she was referring too. She was very brazen. This talking to girls was new to me, but it seemed to be something that I wanted to pursue.

“I could see that, it looked like fun.”

“It is, maybe you should try it.”

“With who?”

“Me of course, Andy won’t mind will you?”

Andy was completely out if it; he had a confused look on his face as he didn’t know what we were referring too. Hell, it had taken me by surprise as well. Was Janna suggesting I put my hand in her bottoms and finger her? There were just too many things happening all at once.

“Janna, what are you talking about? Tom isn’t interested in anything you do, are you?”

“I really don’t know, but I think it could be interesting.”

With that Janna stuck her tongue out at Andy and left, her small tight bottom swaying with a lot of emphasis. Her bikini was pulled deep into her bum crack, she actually looked bare. The feeling was coming back to my weapon again.

“Do you really want to talk to my sister? She is a real pain you know. She is always trying to get me in trouble.”

“It can’t hurt for me to talk to her; maybe I can get her off your back?”

“Could you? She is always tattling to Mom about me, everything I do wrong, even when I get in trouble with the teachers at school.”

“Same with me, but we don’t have to worry about that until September.”

During the short trip home everything that happened today was overwhelming for me. First, Andy giving me a blowjob, the guys in the group talking about things they never experienced and a blowjob was one of them; now I would bet that I was the only one in my crowd that had actually enjoyed one. Thinking back, smiling, Andy did have a nice soft mouth.

In bed my handjob was inspired by the images of Janna masturbating and Andy on his knees sucking. What would tomorrow bring?


The day started as usual, with a pick-up game of baseball. With the daily heat at its peak around one, we usually hit the pool or just went and did our own thing. Today, my thing was to feel Andy’s lips engulfing my raging hardon.

“Hey Tom, are you ready to head home?”

That was for the benefit of the guys still hanging around; there was a glint in Andy’s eyes that told me he was looking forward to a repeat of yesterday’s performance. The uncomfortable feeling my erection was producing would welcome his manipulations.

“Yes, Mom has a few chores lined up for me, let’s go Andy.”

After a chorus of goodbyes and the commitment to returning for a game tomorrow we headed out. Once out of ear shot of the group Andy seemed more relaxed. I was sure he thought everyone had heard of what happened between us.

“Does your mom really have some chores for you?”

“No, but is sounds good.”

That brought a smile to his face.

“Good, all I could think about last night is how good it felt to have your cock in my mouth. I sure like your cream.”

“Did your sister say anything about yesterday in the tree house?”

“She did question me, not so much about the time in the tree house, but just questions about you. She thinks you are hot.”

That bit of information didn’t help my uncomfortable bulge. The only thing good about the trip to Andy’s was the knowledge that relief was on its way. So Janna thought I was hot, what else she was curious about. The vision of her playing with herself had that tingle running through my body and ending up in my shaft.

Finally at Andy’s, we parked our bikes and headed for the tree house. The back yard was devoid of anyone; I was hoping to see Janna. As soon as Andy had the rope ladder tucked away and the trap door closed, he was on his knees in front of me. I could feel his soft hand guiding the head of my cock to my fly, a quiet zipper sound as the tab was pulled, and then the feeling of air hitting my cock told me he had accomplished his goal. Andy seemed to take forever before the feeling of his moist mouth engulfing me that indicated my need to ejaculate would be forthcoming. There was a sound below, it was Janna strolling to the pool and she was alone, wearing a white cover-up. She looked up, saw me and smiled; with us eye to eye she slowly let the wrap slip off her shoulders. The display nearly had me cum prematurely. She was not wearing a bikini but just her bra and panties. Their sheer white colour had her looking naked. Even from this height, her dark nipples were very obvious and the area between her legs, the mystery was exposed.

Andy was oblivious of what was happening outside, on his knees and his mouth full of me; he was in a world of his own. The vacuum action of his soft mouth had me slowly thrusting back and forth. With my view of Janna on display before me, her brother joyously engaged in what he enjoyed, what could be better? Even at my age, masturbating as often as possible, the urge to hold back my inevitable climax had me fighting it off, wanting to savor the feeling for as long as possible. Finally at the point of no return, supporting myself on the window sill with my hips thrust forward, my cock totally embedded in Andy’s deep throat, he received my gift of hot thick creamy cum, just at the point of satisfaction Janna opened her eyes, smiled at me, pursed her lips and pumped her finger in and out. Did she know what her brother was enjoying?

Weakened by a great climax, legs were like rubber, I collapsed on the floor.

“Andy, that really makes me feel different, I have never cum hard masturbating on my own.”

“I like doing it Tom, and the fact you never told the guys means a lot to me. Don’t forget to talk to Janna. She was on my case yesterday.”

Janna, yes Janna, I hoped she was still lounging when we left. Just the thought of seeing her close-up started a spurt of growth to my tool, a motion Andy picked up on right away. Leaning over me his mouth engulfed me for the second time; this was something I could get used too.

“That feels so good.”

Andy just mumbled with his mouth full of my growing erection. His hands caressed my balls then his finger found my asshole. The sensation he produced was all new to me, with his sucking and probing, he had me fully erect and thrusting upwards. Every time my bum lifted, his finger seemed to push against my tight asshole. Eventually his finger was buried in me. With the combination of his finger moving in and out of me and his sucking, I came again for the second time and so quickly after the first one, it had to be a record for me. With his finger still buried in my ass, he used his other hand to work every drop of cream out of me. Now I was totally drained.

“Where did you learn that?”

“I do read a lot, and found some books about guys enjoying guys. Every time I read the parts about a guy sucking a guy, I get really hard; I have always wondered what it would be like to do it. I am glad you don’t mind me sucking you. But Janna found the books and has threatened to tell Mom.”

“Let me talk to Janna. When we leave, you go into the house; Janna is at the pool sunning herself.”

“Okay, when can we get together again?”

“Soon, I hope.”

A smile greeted me; he leaned over me and gave me one last suck. With Andy blowing me we never left any evidence of what had happened. After making sure that we were presentable we climbed down. Andy quickly disappeared and I headed to the pool area. Janna was still in the same position, legs spread. Up close she looked even better than she did from the tree house. The thick mound between her legs had a magnetic appeal to me. I wondered if Jayden and Bree were the same between their legs.

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