Let me first start describing my family. It's just Mom and me. Dad cheated on Mom just after I was born, and Mom threw him out.
He disappeared, and I guess he did not care about me. The feeling is mutual. I never recall Mom dating anyone, but always wondered why. I was too shy to ask girls out and my Mom kept pestering my about it.
However, I enjoyed being just the two of us. I was always the man of the house, but Mom always treated me like her little boy not wanting me to grow up. For example, every time I do something wrong she will spank me, even to this day. I always tell her I way too old to be spanked, but she says that if I child misbehaving like a child that I must be punished like a child. I forgot to mention that when she spanks me, I must be completely nude.
I didn't care about it when I was young; except for a few times we had company. Yes, even in front of company. But when I started puberty, it freaked me out. I went through almost a year without being spanked because I thought I was too old for that. Then a couple of months ago, I did something really stupid (which is another story). I remember my Mom yelling for me. "Bill, get your ass over here right now!" she yelled. I always know I'm in trouble when she calls me 'Bill' because she usually calls me 'Billy'.
She gave me a big lecture about what I done wrong. Then, "time for your punishment. Strip!" "Mom, I too old for that.
Can't I be dealt with some other way?" I pleaded. "Nope, behave like I child, be punished like a child. Maybe when you start acting like your age I could take away your games, computer, or TV. But I'm afraid this will do." "Do I still have to be naked? I'm grown up now." I realized I was not going to win this argument. "Then why don't you act like a grown up. Since this really bothers you, for now one any punishment, like not doing the dishes, will result in spanking until you completely convince me that you are a man." I wondered why I keep making things worse.
She continued, "Are you worried that I will see you pee-pee? You should not be ashamed of your body. It doesn't bother me if you're all grown-up down there.
I have seen plenty." What the hell did that mean? I started taking off my clothes and then, "SHIT!" I accidentally said out loud. "All right, now I triple your spankings," my Mom reacted. "Shit!" I said in my head this time. What was the problem? Hormones, puberty, the stupid idea of getting naked even in front of my own mother are causing me to get hard.
My face started getting red and I started crying. I couldn't believe I was about to show my mother my hard-on. Once, I was down to my underwear, my mom said "oh, you got a little stiffie. Don't worry, I sure my spanking will make it go away." I eventually got my underwear off, and my dick was as hard as ever. My Mom sat in the chair and signaled me to come over. I went to Mom, bent over, and rested on her knees covered by her pants. Then she grabbed to old wooden paddle and started the spanking.
She was spanking harder than I ever remembered. Then, my dick somehow got between her knees and they were rubbing me from all sides. I started having sensations I never had before (I did not know how to masturbate then). Then, I had the feeling of almost blacking out and having the best feeling I ever had before.
I didn't know it then, but know I know it was my first cum. When the spanking was done, I got up and saw white stuff all over her pants and on the floor. I had no clue what it is or what I have done. I thought I peed white globs all over her. I was freaking out because I did not know what was happening to me and what my Mom would do. "Billy, look at the mess you made.
Can you not control yourself? Apparently not, since you are still a 'child'," she said firmly but not yelling at me which surprised me. From then on the spankings were more frequent. She started using a towel over her knees for my 'leakage'. Eventually my orgasms started going away during the spankings. I guess it was most likely due to figuring out how to masturbate. However, I always had hard-ons during the spankings. Last week, our neighbors moved out of there house.
They were an old couple that would always invite me for cookies or let me use their pool. Now we are going to have new neighbors, and why would they let me use their pool. I look outside my bedroom window to get a look at our new neighbors moving in. Eventually I see a gorgeous woman about in her mid-thirties with D-cup tits go out in the back yard. Awesome, maybe I'll get to see her in her bikini sun bathing or something hot like that.
Hey, I'm a horny teenager. Who is that? Is that her daughter? An absolutely beautiful girl my age with some perky B-cup breasts comes out to the backyard checking out the pool.
Maybe I'll get to spy on her too. The most beautiful girl I have ever seen lives right next to me. Soon, we will run into each other start talking and maybe hit it off.
But, I'm too shy. I am definitely going to freak out when I meet her. I needed to clear my head so I go downstairs to watch TV in the living room. I find my Mom is watching TV in the living room. "Hey Mom, who just moved in next door?" "Mrs. Calhoun and her daughter.
I have heard that they are very nice." "Is it just them two? Where is their dad? Was he an ass too?" Whoops, I brought up a sore subject. "Bill, Mr. Calhoun just died in Iraq. He was a Marine. Be careful what you assume especially in front of them.
How about we go say hello to our new neighbors?" Now I'm panicking. "Right now. I really don't want to. Can I just relax?" I reply trying to get out of it. "What's wrong with you? Too shy. My poor baby." Yep, I will find a way to never grow up. "That's right. Did you see Amy? She's cute. You need to get over your shyness so you could talk to her. Come on baby, try to be a man." We get up and head next door.
My heart is pounding. I should have stayed in my room and just listened to my music. Now I am going to embarrass myself in front of that beautiful girl. We go up to the front door and ring the doorbell. The mom answers and the daughter are right behind her.
Luckily, my Mom speaks instead of forcing me to introduce us. "Hi, I'm Joanne and this is my son Billy. Say hi Billy." "Um, hi" is all I can muster out. "Hello, my name is Donna and this is my daughter Amy," happily says the mom. Amy sort of speaking and whispering "hello". She looks nervous too. We were invited in, and both our moms were chatting the whole time luckily.
Mrs. Donna starts talking about setting Amy's desktop computer up and my Mom mentions that I am a computer whiz and I could help set it up. Mrs. Donna tells me "Billy, that would be wonderful, take those boxes to Amy's room get her computer running.
That would be so wonderful of you. If we had to do it ourselves, we would never figure out where each wire goes to." I am certainly no computer whiz but it is an easy task for me. Next thing I know, our moms stay in the living room, and Amy and I are in her room.
Now I am really scared. I am alone with this hot girl, and I mean super-hot beauty, in her room. I start unpacking the boxes and get started with the computer. "You know, you don't look like a nerd," Amy says. For me, that was an awesome complement. Now I needed to counter. But I could not say anything. I keep working on the computer. She sort of bends over to see what I'm doing, and I could see a little bit of cleavage of her tiny breast. I even see a hint of her bra.
I am trying not to stare. Eventually I say "I sorry to hear about your dad." She comes to me and gives me a hug. At first I think "I didn't screw this up" and then realize her hugging me and pressing her breast into my side. "I really miss him. He was strict but he was a loving father." She pauses then says "may I ask about your dad?" "Well, he decided not to be a part of our lives so I won't be part of his." She gives me another hug, but this time she lingers a bit.
Here I am having sexual thoughts about her but knowing she is going through an emotional time. It didn't take long, but I power up the computer and it starts up flawlessly. Thank God. I didn't want to screw that up.
I hear my Mom call my name. I was hoping for some free time with Amy in her room alone. Might as well quit while I'm ahead. "Billy, did you get it working?" my Mom asks.
"Yeah, no problems," I reply. "Wonderful, can you come back after our internet is connected so the wireless works?" Mrs. Donna asks. "Um, sure." "Well, we must go. It's getting late," my mother says. "Don't worry; Billy will always be available if you have problems with that thing." Now I can relax now that we are back home. I am going to jack off all night from my experience today. I wake up late due to my 'hard' night.
But, I needed to say bye to my Mom before she went to work. I should mention that it is the start of summer so I don't have school. However, I need to tell Mom 'good morning' and 'bye' before she leaves, or she might punish me. Well, we have our goodbyes and leave me alone for the day.
I go to my bedroom, or the 'jackatorium', and browse the internet and have my fun. Eventually, I peek into the back yard, and I see Amy walking out in her small green bikini.
Perfect. This is better than the internet. She turns around and then, Wham. She is wearing a thong. Her body is perfect. I completely strip and start jacking. I keep edging so I don't orgasm trying to save the moment. Unfortunately, I lose track of time. My bedroom door is wide open. My Mom walks in seeing me naked, peeking out the window masturbating. "What the hell are you doing?" I froze. She walks to the window and takes a peek to look at what I'm seeing.
"Are you spying on our new neighbors? And masturbating to them? That's disgusting. I'll give you five minutes to clean yourself. Then, come down to the living room for your punishment," she says disappointedly. I wipe my pre-cum off my penis realizing I jacked off all day without having an orgasm.
I walk down, and Mom is sitting on the chair with the towel on her lap. This time it is a long spanking and somewhat a relief as I let go my stuff into the towel. She gives me a good lecture about how perverted that was, and maybe I should not be allowed to see Amy. Again, I always know how to screw things up. A couple of days go by trying to be my best.
Fortunately, the episode wasn't too dramatic. My Mom and Mrs. Donna were hitting it off and were spending a lot of time together. But, I'm too shy to go over there on my own. My Mom comes in, "hey Billy, Donna and Amy have their internet hooked up and need you to get their router, wires, and wireless connected. Do you have time now?" She obviously didn't know about computers. "Um, yeah, could you come with me?" I didn't want to be there by myself trying to figure out things to say.
"Okay, my baby boy," my Mom again reminding me I'm still not grown-up. "Now, don't be perverted around Amy. I don't want to have to punish you there." Punish me at their house!
I haven't been punished in front of other people in years. Is she going to force me naked in front of them? I know she would, but maybe she is trying to scare me.
I will have to be on my best behavior. I didn't even argue with her knowing it would make it worse. We arrive at their house. Mrs. Donna is wearing a low-cut blouse revealing a ton of cleavage, strangely just like my mom. Amy is wearing a tight black button-up blouse which the buttons near her breast are struggling to keep them contained.
I can even see a hint of her bra from the side between the buttons. Well, my Mom and Mrs. Donna are chatting while Amy and I are in her room while I set up the Wi-Fi router.
"All done." I shout. Amy says, "thank you so much, you are so smart and cute." That made me blush red big time. Mrs. Donna and my Mom come in to see my progress. Mrs. Donna says "I don't see anything on the computer." So I fire up the internet browser and boom: A porn site pops up.
I completely don't know what to do and everyone is silent. The last thing I need is to be remotely blamed for this and be punished. Mrs. Donna asks, "Billy, you're the computer genius. How does a site like that pop up as the first page?" "Um, my guess is that it is set up to go to the last site that was visited," I slowly say. "Amy? Were you looking at this before?" Mrs. Donna asks. "I'm so sorry," Amy whispers as she starts to cry. I feel so sorry for her wondering if I can take the blame somehow.
Wait What! No. I can't be punished. Stupid me. Keep my mouth shut. "Amy, how could you embarrass me in front of our new friends? You are so immature. What kind of young lady looks at that crap?" Mrs. Donna shouts to Amy. "Maybe we should go," my Mom says also trying to get out of this embarrassment. "No, you two stay. She embarrassed me in front of you. Now she must be punished in front of you." Punished!
What kind of punishment? Amy's eyes grew extremely wide. "Take off all of your clothes. Time for your spanking." Mrs. Donna tells her daughter. I couldn't believe it. I couldn't believe what is happening to me. Amy goes through the same thing I do. And now she is about to get naked in front of my Mom and me. For the first time in my life I am going to see a naked female.
I feel horrible for what Amy is about to go through yet I can't help get excited. "Hurry up!" Mrs. Donna shouts. Amy starts unbuttoning the top of her shirt very slowing.
It was almost like a strip tease. I start seeing more a more skin and more of her bra. She undoes her last button and lets her blouse slide down her arms onto the floor. She has a real sexy black underwire bra with flowers on it. She starts unbuttoning her jeans and unzips. Her jeans slowly fall to the floor as she steps out of them. She reveals her plain black cotton thong.
Another thong. Her mom lets her wear thongs? I try so hard (no pun intended) to keep my composure. "Mom, can you just spank me over my thong.
My buttocks are exposed. That should be enough," Amy pleas with her mom. "No," her mom says firmly. "Humiliation is part of the punishment. Take off that underwear." Amy reaches back and unclasps her bra and slowly lets it fall to the floor with the rest of her clothes. Her breasts are perfect for me to cup in my hands, and her nipples are beautiful begging me to put them in my mouth.
She puts both of her thumbs into the sides of her thong and slides them down revealing a completely shaved slit with her clit poking out. "Finally," her mom says as she sits on Amy's bed readying her lap for spanking. Amy bends over and rests her stomach on her mom's lap with her ass and pussy pointing almost strait at a 45 degree angle of me. I have a perfect view of her pussy, ass, and breast dangling from her chest.
I resist the urge to rip of my pants and mount her right there. But I wanted to focus on the show and save my fantasy for tonight's masturbate-athon. Her mom grabs a hair brush and starts the spanking, counting to who knows what. I enjoy watching her boobs bounce with every spank, her ass jiggling, and her pussy actually getting wet. Eventually, her mom is done.
Amy stands up revealing all the tears falling from her face. "Joanne, Billy, sorry for tonight. Billy thanks for the Wi-Fi set-up. But I need to have a long talk with my daughter so let me show you two out," Mrs. Donna says in a normal voice.
As we walk to our house, my Mom tells me "if you do anything like that, I would be glad to do the same to you in front of company. You know that." She pauses for a second and asks me "is this your first time seeing a girl naked?" I slowly move my head up and down. "Honey, I know you seen a lot today. But that was not sexual.
That was a punishment. Not something to masturbate to. Yes, that's right.
I know you play with yourself almost every night. In fact, I don't want you to touch yourself tonight. You understand! Or else, you will have your own punishment.
And don't think you can hide it. A mom knows everything." I knew I was doomed.
I slowly wake up. My penis is extremely sore. I think I came seven or eight times last night, and did not go to sleep until 3 or 4 am.
I look at my clock telling me it was a few minutes past noon. Shit. I did not tell my Mom goodbye. Yep, I will be punished. Hopefully without Mrs. Donna or Amy watching. I go downstairs to get me something to eat and see Mom cooking dinner. Damn, Saturday. Mom is not working today. "You stayed up past noon!" My Mom yells. "I knew it. You stayed up all night.
What were you doing all night?" I knew I couldn't lie and get out of it. "Masturbating," I softly say. "And what did I tell you not to do last night?" "Not to touch myself." "All right.
You punishment is right now. Get ready." My Mom grabs her wooden paddle. I quickly remove my clothes hoping to get this done before anyone shows up. "Billy, your penis is swollen and blue. Honey, you keep doing this and you are going to hurt yourself. We are going to have to find a way to control your urges," my Mom says very worried. I get on her knee and take my punishment. I am not getting erect most likely due to my penis's hard work out the night before.
However, without that sensation, my spanking is the center of attention, and I feel every blow. This is the most hurt I felt in a long time. "Billy, I don't want you to play with yourself any more.
Maybe we could come up with a way to reward you for not touching yourself. You already know what the punishment it. Do you think you could handle that?" No, I cannot. "I'll try," I tell her knowing I'll fail.
My Mom goes work out upstairs, and I start washing dishes to get my mind off things. I finish that and do some more chores. As I am taking the garbage out, I meet Mrs. Donna and the lovely Amy. "Is your Mom home? We want to visit for a while," Mrs. Donna greets me. Amy is forcing herself not to look me in the eye. She still must be embarrassed from last night. "Yes, she is home, working out upstairs.
I'll let you in." I open the door letting the two beauties in our home. I go upstairs to tell my Mom we have company. I find her in the spare room where the treadmill is, "Mom, Mrs.
Donna and Amy are here." "Oh, that's great. Billy, have you done all your chores today? Dishes, vacuuming, and the garbage." "Yeah, I just finished." Whoa. That was close. I could have had two spankings in one day.
Rare but it happens. And Amy is here. I realize that one day I will screw up and they will get to see my large, erect penis. Crap! Now I'm getting hard. Wait; do I want this to happen? I'm really getting messed up. My Mom and Mrs. Donna are chatting up a storm and eventually Amy and I get talking. I have to break up the awkwardness and brought up the subject. I tell her, "I'm sorry about last night.
It must have been awful and extremely embarrassing." "I'm sorry you had to see that," she tells me. "My Mom has always spanked my like that. It has been a while since she has done that. I was very little since she done that with company. I just don't want anyone seeing my bits. I don't want anyone to see my awful body." "But, you're beautiful," I quickly reply.
"And you have the most perfect body I have ever seen." Okay, that was the most screwed-up sentence I ever said. 'Most Perfect'. And 'I have ever seen' does work because the only other nude body I ever seen was my own. "Oh, you really think so. You are the sweetest boy I ever met." She smiles as her eyes get wet. "And I should tell you. Look on top of the desk. See that wooden thing." "What is that? Is that a paddle?" "Yeah, that's for my punishments," I tell her as her eyes grow wide. "Also, I have to be naked too for my spankings." "You're kidding me," she says in a shocking voice.
"You too. But you're a boy and she's a girl. Don't you get embarrassed?" "Duh, yeah," I reply. "When was the last time?" I gulp and say, "An hour ago." "For What?" "Waking up late," I tell her leaving out fact that it was because I masturbated all night thinking of her nude spanking, wet pussy, and jiggles boobs.
"Um, what about in front of other people?" She asks. "Yea, that too. But that hasn't happened since I was six or seven.
But, I'm sure it wouldn't bother her to do that again." Amy and I now have this common bond. My shyness is not having an effect on me with her. I may be in love with this girl. Well, their visit went on without a hitch. Both Amy and I are hoping not to get in trouble while we were together. But, I can't wait to see her again. The next few days pass through without a problem and no spankings (at least with no one witnessing). Today, I tell my Mom goodbye before she goes to work. I watch a couple of boring court shows on TV.
I play some x-box and trying to enjoy my summer off. It was so far a beautiful wasted day. My Mom gets home and as she opens the door Mrs. Donna and Amy walk in. I get to enjoy being with my 'girlfriend'. I use it in quotes because we haven't gone on a date yet or even discussed the status of our relationship. However, I enjoy being with her, talking with her, and looking at her cute face.
Hey, I'm not thinking about her body. Progress.
My Mom and Amy's mom are chatting up a storm. Amy and I are getting to know each other. My Mom asks, "Anyone for drinks? I'm thirsty." Mrs. Donna asks for some kind of alcoholic drink. Amy and I both ask for a Coke. My Mom yells from the kitchen, "Bill, why hasn't the dishes been done?" OH SHIT! I went all day without doing any chores. My face turned immediately red knowing what's about to happen. "What's wrong?" Amy asks softly.
I couldn't answer her. I knew it was eventually going to happen. However, it is happening now. Mrs. Donna and my lovely Amy are going to see my dick with the largest hard-on I may ever had. I haven't masturbated all day. I knew I would not be able to take it.
"Bill," my Mom ask as she enters the living room. "Why you did not do the dishes today?" "Um, I forgot." "You forgot? What did you do all day today?" "Watch TV, play games, um," I say softly as I start to whimper.
I try to think of something to get me out of this, but no use. "I bet you spent the entire time masturbating. Didn't you?" Wow, that was messed up. In front of Amy and her mom. My relationship with Amy is doomed thinking that I'm some kind of pervert. I quickly reply, "No, I didn't. I swear. I promise. You must believe me," I plea trying to look like I'm not a creep. "Well, you seem insistent on that," my Mom says, "What about when you went to bed last night?
And the night before?" Looked down and couldn't even answer her. How does she know? "I can tell that you masturbate every night. How many times do I need to tell you that you must to learn how to control yourself?
All right. I'll get the towel. It is time for your spanking," she says with both Amy and her mom right there across the living room.
I plea, "no, please, I." "Are you really going to think I am going to back down? Strip." She interrupts. Mrs. Donna weighs in, "You know how society looks down upon spanking children today, but I believe it is the only thing that keeps our kids in check." "Absolutely, look at our kids.
They're not out dealing drugs, having orgies, or whatever else is getting them in trouble these days. Our kids make good grades and well behaved compared to those delinquents running around town," my Mom replies. They are both proud about their spankings and justifying it to themselves. "Hey, this isn't some kind of time-out.
Strip!" My Mom is just standing there waiting. I remove my shirt and throw it to the floor. Amy is actually smiling. She is enjoying this. Did I have that smirk on my face when this happened to her? I'm just standing there shirtless while the three of them are staring at me. My Mom is motioning me to continue. I slide down my shorts revealing my briefs. That's right, tighty-whities. I haven't grown up yet to boxers yet according to my Mom. My package is clearly outlined by my briefs struggling to hold down my erection.
Okay, here it goes. I slide down my underwear, and my erection is released by the waistband and pops up slapping my stomach making a loud sound. Amy un-controlling lets out a shriek. Her mom with an evil tone asks her, "You want to be next?" Amy moves her head left to right slowly. "Come on," my Mom says sitting in the chair waiting for my arrival. I bend down and rest myself on her knees covered by the towel. Whack, Whack, Whack.
I couldn't control myself. I feel it coming. I am having the strongest orgasm I ever had leaving plenty of evidence on the towel. I actually black out. "Billy, Billy, wake up," I hear my mother saying. I stand up looking at my deflated cock and then the blue towel full of white spunk. "Billy, you still haven't learned to control yourself.
You will never become a man unless you can control that thing or else it will control you," my Mom tells me. Here I am naked and crying in front of my Mom, Mrs. Donna, and most importantly Amy. "Put your clothes back on. We don't want to stare at that thing all day." I get all my clothes back on and sit next to Amy.
My Mom and Mrs. Donna start chatting like nothing just happened. "I do," Amy whispers to me. I give a quizzical look, and she clarifies, "I would like to stare at your thing all day." For once, I feel like a man because a girl likes my manhood. That's right.
Great, now I feel empowering because of that comment. However, I was just spanked by my Mom. I'm really going to be messed up for all of this. The rest of their visit became uneventful. Eventually, they leave to go to their home. Amy's mom and my Mom hug each other and say their goodbyes. Amy embraces me, giving me a tight hug pressing her breasts into my chest, and gives me a kiss on the cheek, "bye, sweetie." This girl likes me.
I should keep getting in trouble for more spankings especially in front of her. Wait, what am I thinking?