My Dingaling
Copyright© 2005 by Jack Spratt
Chapter 3
Erotica Sex Story: Chapter 3 - 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
Special thanks to Pete ‘the old fart’ 2018 for his expertise in reediting and reproofing.
All that went through my mind was the obvious fact I was in deep shit and Caitlin’s mom was going to castrate me. Caitlin finally came down to earth and the realization that her mom was on the warpath settled in. Caught with my hand in the cookie jar or should I say face, it must had been quite a sight for Vickie, me standing naked in front of her, my cock now in an infinitesimal state, my face coated with her daughter’s very tasty cream. There wasn’t much to say.
“Tom, I think you better get dressed and go home. I will talk to your mother tonight. Young lady you have a lot of explaining to do!”
I set the record for slipping on a wet bathing suit, my shriveled up status in the cock department sure helped, leaving the house I didn’t think my feet hit the stairs and getting home and rushing to the bathroom and locking the door. My heart was pounding. I’d had a gut feeling something shitty was going to happen as soon as Caitlin suggested we kiss, but did I heed the warning? No, my cock did the thinking and now I would pay the price. Mom would kill me for embarrassing her, and what was left of me would be permanently grounded, but at least Jayden wouldn’t be in trouble, and even grounded she would still be my salvation.
It was no longer if I got grounded, but for how long and under what conditions, hell maybe high school would be over. The only good thing was Vickie didn’t catch me trying to fuck her daughter because that would have been my next swan song.
My erratic breathing settled down, the sounds and scents of the house were all familiar; Mom was in the kitchen, there was an occasional bang as she prepared dinner and the smells told me we were having beef roast and the trimmings.
With my hearing set on acute, every time the telephone rang, the suspense nearly killed me. The anticipation of the axe falling kept me close to being sick, but so far each time the phone rang, the house remained quiet. An hour and a half later Mom called me.
“Tom, dinner is ready.”
Would this be my last supper? Sheepishly, entering the dining room, Jayden looked at me questioningly. Using direct eye contact and a shake of my head she got the message and engaged Mom in a conversation about her day. Eating took my mind off my problem momentarily, but that devastating feeling returned when Mom said,
“Tom, Mrs. Croley called and said she would like to see you after dinner, it is nothing especially important, but something to do with Caitlin.”
Just that statement, nothing else. Mom continued her conversation with Dad as if nothing out of the ordinary happened. Didn’t Vickie tell her? Why the reprieve? Did Vickie realize the torture she was putting me through, did she even care? I doubted it.
Dinner now over, I excused myself.
“Don’t forget, Mrs. Croley wants to see you. It is likely about you taking Caitlin to the pool, she mentioned how thankful she was, and it gave her time to finally get to the hair dressers.”
“Okay Mom, I will call her now.”
In the privacy of the rec-room, I picked up the telephone and it felt like it weighed nearly one hundred pounds, painfully dialing the number I waited.
“Hello.”
“Mrs. Croley, it is Tom. Mom said you wanted to see me.”
“Yes, young man, I do. We have to talk.”
“Can’t you tell me what you want over the phone?”
“No, we need to talk face to face. When will you be over?”
“Shortly, I will tell Mom.”
What was worse, not knowing what was going to happen with Vickie or the thought of Mom finding out and how she would be punishing me? After last night with Jayden, the day had started off with a lot of promise; even Lex and Brenda wanting to revisit what happened yesterday, but after this afternoon it might never happen again. In the matter of a few seconds all had changed for the worst.
The stress of the unknown had me feeling shitty and uncomfortable. A quick shower and clean shorts made me feel a bit better. The thought of facing Vickie quickly brought me back to reality.
Lightly knocking on her door, my hope was she wouldn’t hear and I could disappear. My duty would be done and the repercussions would be delayed. But that wasn’t to be, the door opened and there stood Vickie looking like a goddess, even with the axe hanging over my head, there was a tingle where there shouldn’t be considering the circumstances. Her flowing blond mane was shining, lips glowing with gloss, her luscious body covered in a soft yellow wrap tied at the waist. It did little to camouflage her memorable breasts. The scent of perfume and shampoo hit me; and again that aggravating tingle hit me.
“You wanted to see me?”
“Yes, come in.”
She lead me into the living room, Caitlin was nowhere to be seen. She was likely grounded in her room. My last image of her was with her gangly legs spread, her pussy lips opened and coated with her juice, the thought of which gave my tool another reason to tingle. Hell, given another fifteen minutes, her mother would have caught me with my cock buried in her daughter, assuming I could get it in.
“Sit down Tom; we have a lot to talk about.”
We sat in opposite chairs.
Even in this situation I couldn’t help but admire how beautiful she was. Vickie looked like a model, her hair shining, her eyes brilliant and me waiting to be castrated.
“I suppose you are wondering why I didn’t tell your mom about you and Caitlin.”
“Yes.”
“Well that was my intention until Caitlin told me she would make my life a living hell, she may be small, but she can be a handful. That is one of the reasons why I was happy that you volunteered to take her to the pool. Her willingness to let you be her guardian even in that small way makes her feel grown up.”
Watching her mouth move and concentrating on her luscious coated lips had my mind imagining kissing them rather than focusing on her words and their meaning. Vickie was a beautiful woman. She shifted her body and more of her lower legs were exposed. Her tanned skin was an exciting contrast to her yellow robe. She still hadn’t told me why.
“After Caitlin made me promise and cross my heart not to get you into trouble she told me how wonderful you made her feel with your tongue. Even my husband won’t do that for me.”
This was more information that I really didn’t need to know, a soft blush of embarrassment started at my neck and slowly filled in my face. There was nothing to stop it. Even with that confession, it still didn’t cover why she needed to tell me in person.
“Do you find me attractive?”
From a light shading of a blush to a full blown one in less than three seconds gave her the answer. She smiled.
“Shit, I shouldn’t even be asking these questions. You are just a boy. Now I feel ridiculous. Forgive me.”
This seemed to be going nowhere, but I felt better knowing Mom wouldn’t find out about Caitlin and me. The burden of guilt had been removed. But what was going to happen next? Vickie shifted her body nervously as if she was really uncomfortable, her robe rode up her legs and now I was staring at a pair of beautiful white lacy panties full of Vickie. The bulge between her legs was very sizable. The tingle was starting to grow ludicrously. Hydraulics were getting involved. My cock was growing.
“Maybe this wasn’t a good idea. Perhaps you should go home.”
Now totally confused, standing and about to leave Vickie blurted out.
“Can you do me like you did Caitlin? Now I said it. I feel so foolish.”
This couldn’t be happening, could it? We stared at each other than my eyes drifted to her pussy. Even from here an obvious spot of dampness seemed to spread outward on her panties. Vickie was wet and horny.
“You want me to lick you?”
Now the blush was on her. She looked at me, then my bulge, and nodded her head. This beautiful woman wanted me to lick her pussy. Now I was really hard. This was something all guys think about, now it was going to happen.
“What about Caitlin?”
“What about her?”
“What is to happen between her and me?”
“I could tell you both that it can’t happen again, but I can remember the first time I was with a boy, there would have been nothing short of locking me in a jail to stop it from happening again, just be very careful and above all else be gentle.”
What was to happen next? It wasn’t that I wasn’t game to lick Vickie, but she was an adult. My look of confusion brought a smile to her face; still sitting in her chair, she lifted her arms beckoning me to her. Quickly between her legs, she pushed me to my knees, lifted her bum and lowered her panties to her thighs.
“You can do the rest.”
The rest started with sliding her panties down her long legs and then off and gentling spreading her legs. What I was graced with was a woman’s pussy, framed in long blond curly hairs that look like they have been watered down as they were plastered to her thighs. Her vaginal scent hit me like a sledge. Unlike the girls, it was strong, potent and appealing. My face was drawn into the hairy abyss. Gently spreading the hair revealed two very thick lips and her tongue lips were so large I would only be able to get one in my mouth at a time. But the cap of this discovery was the protrusion on the top of her pussy; it was over an inch long and looked like a miniature Dingaling. When the tip of my tongue touched her extended clitoris, her body shivered. Wow, was it large. Running my tongue up and down her slit got numerous moans and groans, her body slid down in the chair then she lifted her legs and placed one over each chair arm, spreading her pussy lips and exposing one very large hairy anal pucker, now open and appealing. None of the girls had hair surrounding their puckers. With her clitoris in my mouth and me sucking, my finger found her anal opening; easily sliding deep inside, the heat penetrated to the bone. In moments her body was bucking, twice she slammed her pubic bone into my lip. Hell, I could taste my own blood. Then she grabbed my head and pulled my face into her nearly drowning me when she came. All the girls together hadn’t produced this much pussy juice.
“Caitlin is right; your tongue is as versatile as she said. Where did you learn that a woman’s asshole was so sensitive as well? My husband thinks it is dirty.”
“I don’t know, I think anything between a girl’s legs is breathtaking.”
“If you do this for every girl you get involved with, you and your tongue will be really in demand.”
It wasn’t that long ago that my face had been coated with her daughter’s pussy juice; although Caitlin’s was much milder, both mother and daughter tasted good. Now I was really hurting. Vickie fingers were running through my hair.
“That was nice Tom; I haven’t felt this way since my first love in high school, Ralph being the puritan he is.”
She noticed my problem.
“You would like to fuck me wouldn’t you?”
Again my blush answered the question. She reached over and ran her hand over my tool, looked at me inquisitively. She felt me again this time with more gusto.
“How old are you?”
“Fifteen.”
“Fifteen, you are packing a lot for your age. Show me what you have hiding.”
Standing, I dropped my pants and shorts, exposing my tool to her gaze.
“Hell, you are nearly as large as Ralph. Do you know how to use that?”
“I think so.”
Getting up from the chair, the robe slipped off her shoulders, catching it before it hit the floor she turned and beckoned me to follow. Her shapely ass movement seemed to flow with her legs; there was a large expanse of flawless skin, distinctively marked with tan lines. Her very well-muscled legs were taut and well defined. Upstairs we passed Caitlin’s room, the door was closed and the sound of the television told me someone was in there. I wondered if she knew what her mom had planned.
Vickie’s bedroom was large with a king sized bed as its focal point. Two doors lead to a balcony. Watching her every movement she pulled down the bedspread and the covers revealing maroon sheets of a very soft material. Laying down she spread her legs, opening her pussy lips. She looked at me and waited, but not for long. In seconds my clothes were in a pile and I was between her legs. Her hand guided me to her body; my cock found its home and slid into a very moist cavern. I couldn’t believe this; Vickie really wanted me fuck her.
“You feel good Tom, much lighter than Ralph, but you are in as deep. Please go as slow as you can, I want to enjoy this.”
There was no way to describe how it felt to be lying on a woman and one as well-endowed as Vickie. She was so soft and her large breasts were like pillows supporting my chest. Being tall for my age we were face to face. Vickie pulled me to her and kissed me. What a kiss! Her lipstick had a pleasant fruity taste, so I kissed her again. Then we got down to work. After establishing a rhythm she closed her eyes and gave a moan with every thrust. The pressure to ejaculate built, resisting soon won’t be an option. Every measured stroke brought me closer, finally there was a twinge in her body, and then her muscles tightened. That signal was the same with all the girls, she was close to cumming. Finding myself being lifted upwards, Vickie tensed, stopped breathing for a moment, then exhausted her breath and collapsed, that signaled for my cum to pour into her waiting opening. Then she scared the hell out of me, with a sharp piercing scream as she came. Now the sublime feeling rushed over my body from two sources, first with the knowledge that Vickie would not be divulging my transgression with her daughter to Mom after what we just enjoyed, of that I was certain, and secondly, the feeling of my first sexual act with a beautiful mature woman. What could be better than this? Well, maybe two women and their young willing daughters.
Caitlin had to have heard her mom cumming. Would her pussy stretch enough to allow my cock to penetrate her? Likely, as Jayden’s did and they were nearly the same size at the hips.
“Tom, I could feel every blast of your cum in me. Maybe it will get me pregnant, Ralph and I have been trying ever since Caitlin turned three.”
Pregnant?? She had to be kidding, she was a woman, and wouldn’t she be on the pill? Breaking out in a sweat, her hand ran up and down my back.
“Don’t worry about it Tom, if I was fortunate enough to get pregnant, Ralph would think it was great. He is the one that wants a larger family.”
This was all new to me, this pregnant thing. But if Vickie wasn’t concerned, maybe I shouldn’t be as well. All the articles on the net were about avoiding pregnancy, not the other way around.
Her hard nipples were pushing into my chest. When my cock slipped out of her pussy, I slid downwards to examine her breasts. Mouthing one nipple then the other, had Vickie grasping my head in a hammer lock restricting my movements, she didn’t want me to stop mouthing her nipples.
“That really feels good, you have managed to find both of my hot spots, my nipples and my asshole.”
At home, I hit the shower again. My lower body was covered with a crusty skin, Vickie’s dried pussy juices. Just before leaving she reminded me that Caitlin would like to go swimming tomorrow if I didn’t mind. To which I answered same time as today.
What tomorrow would bring should be interesting.
Later when Jayden joined me in bed, she whispered that she and Bree spent most of the afternoon between each other’s legs and she was exhausted, this was okay by me as I was pretty worn out myself. Cuddling up, my mind rehashed the day, the near disaster and then the wonderful development with Vickie. The sights of her luscious body flashed through my mind. With my face buried in Jayden’s soft hair and the scent of her fragrant shampoo, sleep overtook both of us.
Waking up we found that neither of us had moved. Jayden’s eyes opened focusing on me, and then a beautiful smile spread over her face.
“I love waking up with you. We should have been doing this year ago. What happened yesterday?”
As much as I wanted to tell her about Vickie, it was something that would have to wait until later if at all. Sitting up, she looked angelic, her soft skin seemed to glow, whether it was the result of sleeping with me or the new experiences she was enjoying with Bree really didn’t matter, just the fact that she was in my bed was all that really mattered. Leaning over, I kissed one nipple then the other; her soft hand went quickly to the back of my neck pulling me close.
“Humm, that feels so good. You and Bree should get together to compare notes, she likes my nipples as well. So, what are you doing today?”
“I’m going to meet Caitlin this morning and go to the park. She loves the water and swims like a fish. I will likely join the guys and play ball.”
“What about Brenda? I bet she loves this. Imagine, you in her ass and her pussy already. Save some for me tonight.”
Her hand was caressing my now morning woody. She looked at it and at me, was she going to give me a morning blowjob? She moved her body exposing her pussy, her lips opened and a few drops of white translucent cream gathered at the bottom. It was puffier now that she had been fucked and perhaps as a result of Bree enjoying her juice.
“Sis, for you, always.”
Leaning over, she gave the tip a kiss, and then tried to leave. But it was my turn and I leaned over and licked her cream, a very strong version of her love juice. She jumped out of bed and ran to her room.
Now at the table, the taste of Jayden’s juice was still strong. Looking at her, I was amazed as to how different things were since we discovered each other’s bodies. Mom was humming as she readied our breakfasts.
“So what are you two doing today?”
“I agreed to take Caitlin to the park. Mrs. Croley really enjoyed the time to herself yesterday. She thanked me last night.”
“That is nice, young people should show initiative as you did with Caitlin. It is something that pays back numerous times.”
Smiling, Mom would be shocked if she knew how Mrs. Croley paid. I wondered if she would let me do it again.
Getting my bike from the garage, Jayden waved at me. My urge nearly had me suggesting that we return to the bedroom, but Mom was moving about. It wouldn’t be a good idea.
Caitlin was waiting for me. As soon as I was on the street she was beside me.
“Morning Caitlin, how are you this morning?”
“Good and thank you for taking me to the park again. I am sorry about yesterday. I didn’t think Mom would be home that early.”
“It is okay, your mom was quite good about it.”
“I told her if she got you in trouble I would never forgive her.”
“It worked.”
“My Mom did it with you didn’t she?”
“Did it?”
“Let you put your cock in her. I heard the noise she made; it is the same as she makes with Daddy every time he comes home. They usually lock the bedroom door, have a shower together, and then get it on. I always listen and Mom always makes that noise except last night she was louder and longer. You made her very happy.”
“I did?”
“Yep, she was smiling this morning at breakfast; she is making an appointment for me to go to the doctor for some sort of pill. I am not even sick.”
The pill, it has to be the one that was on the net, Vickie was expecting Caitlin to be fucked. My cock was really hard. Caitlin noticed how uncomfortable I was, my cock pushing out against my shorts.
“I asked Mom about what she thought of your cock and she told me to shush. She did smile though like she was remembering something. Did you like her titties? I hope mine get as big.”
I was learning, my mouth remained closed and my feet on the pedals, instead of the usual place, my mouth. Once at the park the usual happened. Caitlin went to the pool, I to the ball diamond. It took nearly an hour to complete the first game, saying my goodbyes; I headed for the pool and my bench. Mrs. Wiebe was there as well as her daughter, Kaylissa. She was in the water and wearing the same outfit as yesterday. Caitlin was in the swallow part splashing Melodie who was laughing so hard she fell backwards with a splash.
“Good to see you Mr. Bates, I was hoping you would be here. You made quite an impression on Kaylissa yesterday.”
“I did?”
As far as I could recall all I did was stare at her body, especially the display of her beautiful white pussy. There was a tingling in my shaft. Looking at Mrs. Wiebe had me wondering if she, like Vickie, was also interested in young boys. She leaned over flicking some pesky flies from her legs and giving me a wonderful view of her starkly white breasts hanging in her halter top. Her skin might be ivory white, but her nipples were large and a deep shade of rose. When she looked up our eyes met, a smile crossed her face; she seemed to give me a few more seconds of the view then sat up.
“She said you were a hunk, whatever that means?”
It was something new to me as well, now uncomfortable, I moved to relieve the pressure on my hardon. It had a mind of its own. Mrs. Wiebe didn’t seem to notice my bulge or she was ignoring it. Sitting as close to each other as we were; her scent wafted over me and it didn’t help my problem. Ever since Jayden and I became lovers, a woman’s scent tripped off my uncontrollable urges.
Mrs. Wiebe was wearing a black halter top and matching short, shorts. Her tummy was sporting a dangling bobble from her belly button, something I didn’t notice yesterday. There was a slight protrusion of soft skin above the waist band of her shorts; her long legs were smooth and glistening with sun block. Her toenails, sticking out of her sandals were painted with a red hue that matched her fingernails and lip-gloss. She looked so sexy, mind you after last night every female looked sexy. We looked at each other.
“I am not sure what it means, I hope it is something good.”
“It is, she was impressed. I see you are keeping track of that young lady you mentioned yesterday, Caitlin isn’t it?”
“Yes, her dad is out of town often, and her mom enjoys a bit of time on her own.”
“Sounds a bit like me, except I am divorced and spend most of my time with Kaylissa.”
Should I or shouldn’t I? That was a question that was running through my mind. In Caitlin’s case, it provided an opportunity to fuck her mother, would it be the same with Kristina?
“Perhaps I can help. Do you live around here?”
“Help, how? I live on Brant Street.”
Brant Street was three blocks from our house, not an area where any of my friends lived so I was not there often.
“Do you think Kaylissa would let me take her to the pool and give you a bit of time for yourself? You could call my mom and talk it over with her. Also Mrs. Crosby would tell you I am responsible as well.”
“And want do you charge for this service?”
“Charge?”
“Yes, charge. The babysitters I do manage to find cost an arm and a leg.”
Charging hadn’t crossed my mind; beside I loved the way Vickie paid me yesterday. Running my eyes up and down Mrs. Wiebe’s body and thinking there were many ways payment could be made.
“I never thought about charging. Mrs. Croley is a neighbor and Mom thinks it is a good thing to do. She says all good deeds will be paid eventually.”
“Your mother sounds like a very wise woman. Let me think it over. Can I have your telephone number and that of Mrs. Croley’s as well?”
Giving her mine, Caitlin could provide hers when she was out of the water. We sat and watched the girls. Wondering why I didn’t bring my bathing suit had me kicking myself. Finally Kaylissa came towards us; her eyes brightened when she noticed me. Mine brightened as well waiting for her to come out of the water exposing her crotch. She seemed to sense my interest and reached under the water and seemed to tug. Her hips broke the surface; my eyes were glued to her. Her soft pussy lips were exposed and the narrow strip of the bathing suit was pulled deep into her cunt. What a view.
“You remember Tom from yesterday, he offered to escort you to the pool so Mommy can have some time to herself. What do you think of that?”
Kaylissa’s smile suggested she was in favor. Getting out of the pool she stood in front of me shaking the excess water from her body. My eyes were glued to her pussy that, with the exception of the narrow bit of cloth, was totally exposed. Didn’t her mom notice? For some reason it didn’t seem to faze her at all that her daughter was exposing herself to me. As she did yesterday, her mom dried her hair then rubbed the rest of her body, giving her the towel to do her legs. Twice she caught me ogling her pussy; both times she smiled and continued to dry herself.
“I am all for it. You need some time to yourself. If Tom doesn’t mind, neither do I.”
“I do play ball with the guys every morning so I won’t be at the pool’s edge until the game is over, but you can always call to me if something happens.”
“I have been swimming since I was six, and I only talk to the other girls. Mom told me never to talk to strangers.”
“Tom has given me his telephone number and I am going to call Caitlin’s mom as well.”
“Caitlin?”
“That is the other young lady that Tom watches over. There she is with the young oriental girl.”
“I know her, she goes to my school, but is in a different class.”
My eyes hadn’t left Kaylissa’s body. Finally I noticed she had hips and a very well defined body. From the side, the protrusions of her small breasts were noticeable. I still couldn’t get over how pale her complexion was. Her skin appeared flawless. Her legs were long and muscled.
“Kaylissa, we have to get going. Tom, could you get the number from Caitlin?”
“I’ll get her; we have to be going as well.”
Calling Caitlin out of the water she was followed by Melodie. After giving Caitlin’s mom’s number to Mrs. Wiebe, I watched them as they left the park then turned my attention to Caitlin. Melodie seemed to be studying me. Looking at her also caused my tool to get active; her coloring was definitely a focal point. Her lips were rosy red from the cool water.
“Got to go Melodie, Mom is likely home by now. I will call you tonight.”
“Okay, I should be getting home as well. Talk to your later.”
Leaving the park, I asked Caitlin if her mom was actually home.
“No, but I didn’t want Melodie to know that. I want you to lick me again.”
Bong, my cock was hard.
“Are you sure? What if your mom surprises us again?”
“She won’t, I told her not to come into my room if the door is closed, just like I didn’t come into her room when her door was closed last night.”
The house was quiet when we entered, Caitlin grabbed my hand and we headed to her bedroom. The door to her mom’s bedroom was closed.
“I am going to take my wet bathing suit off, I’ll be right back.”
Caitlin disappeared to her bathroom. Feeling very uncomfortable, I slipped off my T-shirt then my shoes and socks and waited. Water was running then stopped, more waiting then the door opened. Caitlin was naked; the sight of her puffy pussy did its thing to me. Her hair was tied back in a ponytail, her face radiant, she looked different. She was sporting lip-gloss and her eyebrows were darker. She had applied makeup.
“Do you like the look? Mom always wears makeup.”
“You look beautiful.”
There was a grateful smile then she crawled onto the bed and sat Indian fashion, her pussy was nicely spread open. The opening was a darker pink than the rest of her nimble body.
“Well, what are you waiting for, take your pants off and join me.”
For some reason, I still felt uncomfortable after yesterday, even knowing Vickie won’t tell my mom. I still couldn’t get over the idea of her letting me see Caitlin naked and licking her daughter’s pussy and maybe more. The more was the interesting part.
“Hurry up.”
Now in bed beside her, she looked at me then at my cock. She had an inquisitive look about her.
“Can I touch it?”
“Of course.”
At first her fingers just grazed the shaft and as she got braver she explored the length and finally pulled back the foreskin exposing my slit and the steady flow of precum.
“It is so cute. What do girls do with it?”
“Lots of things, you can rub it, kiss it and some girls even like sucking it.”
“They put it in their mouth?”
“Isn’t that what you like done to you?”
“I never thought of it that way.”
After the excitement at the pool today with the Wiebe, Caitlin’s soft hand felt good. My imagination went to the sight of Kaylissa’s so white and so puffy pussy. What would it be like to taste her? Then there was a moist feeling on the head of my cock. Looking, it was Caitlin with her mouth full of me, her cheeks deflated as she sucked and pumped. Now that was a good feeling. Caressing her hair she looked up and smiled, not leaving my cock. The sucking and pumping were bringing me to the brink.
“If you keep that up I am going to squirt.”
“Squirt?”