Disclaimer:

First NSFW and you better be over 18.

A good boy spanking is one where the man-boy being spanked has an erection, orgasms, or just ejaculates sometime during the spanking scene. That is a little clinical and it isn't an official definition. I stole the term from another blog post (strictjuliespanks.blogspot.com) that seemed to be the closest things to what happens to me (or I would like to happen to me).

This is my travelogue as I explore this part of myself. Enjoy!

Monday, September 7, 2020

The Game

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

Caught Playing With Myself

I was just so horny that it made me stupid. It isn't that I am not allowed to masturbate but she gets so jealous when she finds out. It seems that she wants to be my only sexual outlet and though she knows that boys need relief sometimes, she would prefer we had sex instead.

What she doesn't understand is that I might really need it and then if I ask her and she says no or not now or whatever, I still have a hard little problem. It isn't like I can be rejected and then slink off to do my business. I don't think she likes that at all. Sometimes relief is better than taking the risk.

The problem is that if she wants some lovin' from me but I'm not ready, willing, and able, that is bad too. Ideally, she would like me ready for sex all the times she wants sex but for me to just calm down when she isn't in the mood.

The scene played out in my head all day making my penis hard and head foggy. I had seen a picture of a male transvestite trying to stroke his penis. S/he was hairless with small breasts and hips that flared like a woman's. The pale penis and testicles were flaccid, soft, and small like a boys. This beautiful creature invaded my thoughts. I imagined gently sucking on that delicate penis/clitoris. Something about the feminine beauty and the male genitals had me confused and aroused.

I found myself home and alone with an erection that was almost painful. At first, I went to the bathroom for a quickie but once my pants were down, I got braver. I undressed and decided that I should be more comfortable so I left my clothes in the bathroom and got naked into bed. I found the lube in the nightstand and got some tissues ready for cleanup purposes.

At some point, I had missed the telltale sounds of my wife coming home. She realized something was amiss and was standing right at our bedroom door as I made my naked entrance, got comfortable, lubed up my member, and prepared myself for a little self relief.

Admittedly there is no way to announce that you are watching someone masturbate that is anything besides jarring. Still, she was upset because to her, it looked like I was taking more care to make love to myself than I usually do to make love to her. Also, as I got started, I was very much enjoying myself. In fact, for all my preparations, I wasn't going to last a minute.

She walked in and I, of course, froze. I spoke first and said, as one could imagine, the stupidest thing possible: "Oh, I didn't know you were home." Like, why would that matter?

Worse yet, my penis just pulsed in my hand. I wasn't ready to pop yet, but the lack of more stimulation was annoying to the little fella.

I will spare you the lecture she gave me which didn't really make much sense but when one is naked in bed with a luxuriously lubricated erection thinking about nuzzling the tender penis of a tranny, it is really not the right time to argue. The upshot was that she was mad, hurt, and offended. Her solution to all of this was to spank me.

This happens sometimes. Spankings hurt and she can really deliver the heat but I get sort of aroused by spanking. She knows that sometimes spankings can be a real turn-on for me but she knows that once my penis goes soft after I ejaculate, I am just the saddest sorriest and most contrite little boy ever.

Truth is that if I know I am going to be spanked after I orgasm, the fear of how much that spanking is going to hurt makes the orgasm just amazing. I am almost thankful for how bad it hurts because I know that I'll take the fear into my next spanking and it will fuel my next orgasm. It is a feedback loop of pleasure and pain. The more severe the spanking, the better my orgasm; it doesn't even matter which order anymore.

Getting caught masturbating, however, was new ground. I wasn't sure but I didn't think she was going to want me to enjoy my orgasm this time. She also knew I wasn't going to 'appreciate' my spanking unless that pesky hardness was gone. Clearly, I had a problem.

"Get up," she ordered as she dropped her purse. "I am going to give you such a spanking," she mused kicking off her shoes.

I struggled to my feet. It was tricky with one hand covered in lube. I ended up standing awkwardly with my erect penis bobbing lewdly as I tried to think of something to say. Nothing came and I just stood there stupidly.

She disappeared into the closet but was back in what seemed like seconds with the hairbrush in her hand. My penis bobbed approvingly for some reason. She just tsk-tsk'd annoyingly and sat down on the chair that 9 out of 10 times is where I get my spankings. She didn't say anything but just waved me over.

I shuffled over and expected to go right over her lap but when I got next to her, she said, "OK, you better finish up." I looked confused. "Go ahead, get it over with. Hurry up."

As aroused and scared as I was, I was also self-conscious. Nervously my lubed hand met my slippery already lubed up erection and started making the motions that I had been making since I was twelve. My knees buckled right away but I didn't want to look like I was enjoying myself too much. Still, it felt awesome and the tingles that feel so good just before I pop started in my belly.

I tried so hard to not look like I was enjoying myself but that made it just build slower. The slow build was amazing and the tingles spread down my legs and across my bottom. I knew that just seconds after I had my little fun, that delicious tingle across my bottom was going to replaced by just blinding pain. The thought propelled my orgasm forward and almost without warning, I exploded. Neither of us had really thought that part through and I sprayed all over the skirt covering her lap before catching the last little bit in my already sticky hand.

She didn't look at all happy. "What a mess. Oh well, you get to lay in it. Come on, get over."

My knees buckled as I climbed over being careful to not make more of a mess. I carefully protected my right hand and navigated clumsily with my left. My post orgasm weakness didn't help me be any more coordinated.

I was only over her lap for a second before the hard wood of the hairbrush tapped gently on my right cheek. With a sigh the wood disappeared and with no warm up, she was in full swing. The pleasure of the moment before disappeared entirely and was replaced by first a ferocious sting and then a bonfire. She spanked hard, fast, and covered every bit of the pale skin of my bottom methodically. I knew she wouldn't be done until it was all bright red.

For my part, I was as brave as I could be. I tried not to kick but I kicked. I tried not to complain but I protested like a little boy. I didn't bother trying not to cry. The tears poured out of my eyes like the semen had from my penis just seconds before.

She stopped when her anger was spent. I was done kicking and my words were just wailing. I was truly sorry. I had been a naughty little boy but I had been spanked clean.

Wednesday, September 2, 2020

One Boy's Journey -- Part 8

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

One Boy's Journey -- Part 6

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

One Boy's Journey -- Part 7

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

One Boy's Journey -- Part 5

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

One Boy's Journey -- Part 4

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

One Boy's Journey -- Part 3

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

Tuesday, September 1, 2020

One Boy's Journey -- Part 2

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

One Boy's Journey -- Part 1

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

The Pool Incident

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

Hot Day

Disclaimer: This is a story of fantasy and is not only not intended to condone or approve of the behaviors contained herein, there is absolutely nothing about treating children as sexual objects that the author approves of, desires, or would dream of doing to an actual child. This work is written in the context of age based role play.

If you cannot understand this, have difficulty distinguishing fantasy from reality, or are in any way confused about what is appropriate and legal sexual expression, stop reading now.

Lastly, I am not a pedophile, don't approve of sexually assaulting children, and only use these themes in my writing because I empathize and identify with the victims of these stories; not the perpetrators. Some of us like to be embarrassed, ashamed, humiliated, spanked, and to be nervous, anxious, and afraid. Weird, right? To read more about why these stories were written, please see the "What This Blog is and is NOT -- READ THIS FIRST" post.

Dress Up

It seemed like a fun game. A little dress-up and pretend. Sure there were rules and the penalty was a spanking if he was “naughty”, but she was paying attention to him and his penis was thinking for him. 

At first, it was just a little weird. She looked pretty and was so excited about finding him clothes and making him looking “pretty”. He didn’t know why he was even playing the game but the more she paid attention to him, the more he was pulled into the game.

It started modest but as the game progressed, he found himself dressed in skimpier, tighter, and sexier clothes by the older woman. She was thrilled with each outfit, each adjustment, and she kept touching him gently, tenderly, and sensually. 

She was searching for the perfect outfit, she told him. He tried on pants, shorts, and then dresses and skirts. The skirts became shorter and then he was standing before her only in a pair of silk panties. His hard penis strained against the fronts as she praised him for looking so pretty. He felt pretty, sexy, and aroused but also nervous. Where was this going? What did she have in mind? He realized that he had no idea how the game ended.

The outfit was frilly but also tight with stockings, delicate shoes, and a locket. The panties didn’t match and worse still, there were none that would match. She decided that he didn’t really need the panties. He was shy but she insisted that he take them off. His privates finally bared, he fidgeted wanting to cover up but not sure if that was allowed. “Oh, perfect!” she exclaimed, “let’s go get some ice cream at that restaurant you like so much.” 

He didn’t know what to say. He wasn’t leaving the house dressed as a girl and certain not naked from the waist down. He looked shocked and immediately forgot how he promised to do everything his mommy asked of him. Thinking it was a joke, he suddenly laughed. She didn’t laugh back. “I’ll just put some other clothes on,” he said tentatively. 

She just shook her head, “no, like this. It’ll be fine. Lots of little girls play dress up. You will fit right in. No one will even look twice at you,” she said with not even the slightest hint of humor. 

“I don’t want to,” he whined. 

It was the excuse she had been waiting for. Seemingly from nowhere the brush appeared in her hand as she patted her lap. “Time for spanking, I think,” she declared. “That will teach you to obey me.” 

Sure, he knew this was a possibility but suddenly he realized this was what she intended all along. Maybe he could get out of it but she wouldn’t play with him again. And she was bigger and stronger, too. Even as he nervously weighed his few options, he knew she was going to spank him.

My New Mommy

I walked in the door and as soon as we could, I was up against the wall getting spanked through my pants with the thinnest and stingiest paddle. I used to wear jeans but they were too thick. This was just a warm-up spanking so that we could do the real thing as soon as the scene began. Her real spankings were always on the bare and always were very hard. It is essential to have a little warm-up or I just can't take too much. 

Once that was over, we could get down to why I was visiting my 'mommy'. "OK, baby, take off your clothes and tell mommy why you are getting a big spanking tonight," she commanded. I'm white and in my late forties. She is black and in her early twenties. Though I pay this nice young lady to pretend to be my mommy sometimes, she has admitted to enjoying our little games and has confessed that she has masturbated or booty-called her boyfriend after our sessions. Lately she has worn more provocative clothing when I come over and taken to shedding clothing as the night goes on claiming that it she is hot, constricted, or worried about something getting ruined. I've seen her in just a bra and panties but never anything less.

Tonight she was dressed in a simple loose and flowing lilac dress that reached almost to her knees. She was clearly not wearing a bra but there was nothing immodest about it and, in fact, she looked modest, chaste and even motherly. Her large but youthfully gravity-defying breasts swayed gently beneath the thin fabric. The dress hugged her young but full lines smoothly. She is not a small woman but not overweight either. Her very dark skin under the light lilac was beautiful and smooth and she wore her hair in a severe business bun. 

I peeled off my shirt and pulled down my pants and underwear revealing my hairless body and hard little penis to her. I left my pants around my ankles for the moment while I explained, "I was playing with a neighbor girl. We were playing mommy and daddy." The story I was about to tell hadn't really happened but was based on something that had happened decades ago. 

"Wait," she interrupted. "Is this neighbor girl younger than you?" 

"Yes," I whispered knowing that mommy was about to figure out how super naughty I was pretending to be. So far, the story was pretty accurate to what had actually happened. She was younger by a couple years but like most girls at that age, she was more mature. 

"How much younger?" she pressed. 

"She is in fourth grade." We pretend that I am in sixth and that she is not actually half my age but more than twice my age. The real story was more an eighth and sixth situation. 

"I do not like where this is going. What were you doing?" she asked sternly. This unfortunately made my penis bob a little. 

"We were pretending to make a baby," I said softly. She just made the 'go on' motion with her hand. "She had taken off her panties and pulled up her dress and I had pulled down my pants and underpants. I was laying on top of her rubbing my pee-pee against her tickle when her mom caught us." This was what I hoped had happened in real life but we didn't get nearly that far. 

Mommy thought for a second. "Did you put your pee-pee in her tickle?" she asked. 

"No," I paused, "we were just rubbing but..." I trailed off. She just looked at me sternly. "It went in accidentally just a little." Then quickly, "she didn't like that and told me to take it out but she was a little loud and her mommy heard, I think." 

"Did you make squirties on her tickle?" mommy asked angrily. Then, before I could answer added, "Or in her tickle, heaven forbid." 

"No!" I said quickly and then, "her mom caught us too quickly." I realized before she said anything what I had just done: clearly I had intended to squirt all over this little girl. 

"Oh my goodness," she said with disgust. "Did she know that you were going to do that?" 

I softly said, "probably." 

"Why 'probably'?" she pressed. 

I was quiet for a second and then offered, "well, we didn't really talk about it but I thought she would know what happens. She's seen me squirt before." Something about having pants around your ankles makes you just say way too much. Or maybe it was all the blood in my penis instead of my brain. 

"She has!", mommy said with a gasp. "When did that happen?" 

"Um, a couple days ago," I offered. She seemed to want more and, well, I was in pretty deep. "We were playing doctor and she was fixing my pee-pee. Cindy was touching me and asking if that was making me feel better and I said it was. Then it just happened and went all over my tummy. She thought it was neat and wasn't mad at all." I quickly explained like it mattered that talking a pre-teen into giving me a satisfying hand job that hadn't totally grossed her out was somehow going to make this better. It didn't. 

Reality check: all different girls and different times. Lots of doctor happened over the years. I ejaculated a couple times during the 'sex play' years and usually it freaked me out more than anything or anyone else. I realize now that what I was playing with was risky and that if things had gone a little further, well, I might have done something really awful. It is that sense that I was always lucky--never smart--that makes me feel so guilty that I crave this punishment. Each time I visit my new mommy, I share another facet of the truth. Indeed, this isn't what happened but what I wish had happened. This story and others like it continue to fuel my masturbation sessions (when I'm not fantasizing about spanking). 

"What did her mother do when she caught you?" mommy asked. 

"She was real mad. I got up and we both tried to cover up our parts but she knew what we were doing. She said that she would tell my mommy what I had done if I didn't and then she gave Cindy a spanking while I was still there. I didn't know what to do so I just pulled up my pants and watched Cindy get spanked. 

"Cindy's mom doesn't spank as hard as you," I added, "but Cindy was really crying." I thought maybe it would make it less bad if I compared my mommy's spanking ability favorably to Cindy's mother's. That naughtiness was probably not going to go unnoticed, however. By the way, I was never caught though it was close a couple times and I am sure one time the adult totally knew what was going on but didn't want the hassle of dealing with us, thought it was normal, or didn't care. 

"Well, you certainly have earned a real bottom blistering tonight. Let's get a look at you, little boy. Take those pants off and come over here," she said as she moved to the wooden chair that she puts in the middle of the room for spanking. I kicked off my pants and then thought it might go better for me if I put them neatly someplace but, well, nothing really worked. I tried. Then I walked stark naked across to the room to the woman that was going to make the next hour or two extremely painful and humiliating. 

She started right in talking to me like I was a little naughty boy. "Remember the rules: if you have to make pee-pees or poopies, just tell me and I'll take you to the potty. No making squirties without permission either. I will use the hairbrush on your bottom if you do. You have to be polite to me at all times or you will get the punishment paddle on that little bottom of yours. 

"Now, we are going to spank you a lot tonight for doing sexy things to the that innocent little girl and making her have to get a spanking. Then, since you want to make squirties so bad, I am going to spank it right out of you. We'll do that later after your bottom is super ouchy. That will make you learn that you need to be older before you start doing sexy things with girls." 

She patted her thigh like I think she would when it was time to go over her lap and I felt my penis involuntarily pulse probably pushing out a little more pre-cum. No matter how many times I get spanked, it always surprises me that I create so much pre-cum that clearly goes to waste. I walked to her feeling the wetness at the tip of my penis feel uncomfortably cool. 

"He is a cute little guy," she said taking me in hand. 

"Oh, be careful; he really wants to squirt bad. He keeps leaking the slippery stuff. That happens before the nice squirties come out," I said trying to sound like a naive little boy. 

"Oh yes, I see you are leaking. Poor baby," she cooed. Her cool hand felt electric on my erection though she avoided touching me where I would be most stimulated. Instead, she felt around the base and stroked the top like she was petting a kitten. With her other hand, she caressed and gently squeezed my scrotum that was holding my testicles nice and tight just like when I am about to cum. "It is like he is crying already. Soon you both will get to cry together. Won't that be nice?" she asked hypothetically. 

I groaned from the faint stimulation and frustration it produced. "That makes your little pee-pee feel good I bet." Then she leaned in close so that her face was just inches from my throbbing erection and taunted, "yeah, this wittle-wittle teenie weenie pee-pee thinks it is a big boy cock. Oh no your not, no your not." She pursed her lips and raised her voice like she was talking to a baby, "look how cute you are. All hard and ready to squirt but you are so little. Little pee-pees can't cum like big penises. Oh no they can't." 

He just bobbed inches in front of her mouth. I was just a few strokes from orgasm and wanted nothing more than to cover her face with my cum. My hands were clenched tight at my sides. 

Looking up at me, she said, "I think he is about ready to pop." I nodded and then she returned to speaking directly to my little guy, "is baby ready to make? Does little baby want to have his little squirty? Of course he does but we can't have that. Nope. This little guy is just going to have to wait." Then, dangerously, she did actually kiss my penis right on the tip but above my slit. "Bye bye for now. 

"OK, turn around and let's make sure you are all clean," she commanded switching gears abruptly. I turned and faced away from her. I knew what to do before she asked but waited anyway. "Bend over," she said annoyed that I hadn't already. Hoping I was squeaky clean, I bent over as far as I could and then felt her pry apart my cheeks even further. The cool air on my pucker was followed unexpectedly by one of her fingers that poked and prodded the area. Then it was gone and when it came back it was wet. She pushed right into me. "Relax," she commanded, "I know what I'm doing." 

It is really hard to relax when anyone unexpectedly intrudes but I figured that it would be OK if I stayed in character; this would be especially difficult for a twelve year old boy passing through puberty. I whined a soft and elongated 'no' in what I thought would be an appropriate high pitch. She just shushed me and probed deeper eventually finding what I knew was my prostate and giving it a nice massage. 

"I have to be sure you are clean inside and out. This will help fill you up and make your squirt bigger too. I know this isn't very nice but it will be nice to make a big squirt later, won't it?" I just mewed because my character would and because I knew there was likely a big penalty to pay for making a big mess. 

She spent less than a minute probing me, extracted her finger and sent me to fetch her a wet washcloth. It was curiously uncomfortable walking after having been diddled and it also was very apparent that her ministrations had created even more 'tears' from my hard penis which were now sprinkled all over my legs. 

She wiped off her finger while saying, "you can't trust little boys. They say they don't have to poop and they look all clean but really they are just too embarrassed to admit it. I had to check, of course." Then, she put the rag on the floor and stood up. "OK, bend over the chair. Let's heat up that bottom of yours," she said just a little too happily. 

We switched places while she fetched the paddle we use for the warm-up time. On the bare and swung with purpose, it was going to sting blindingly. After such a build up, the spanking started with little additional fanfare. She didn't ask if I was ready or even say anything more. As I leaned over the back and held the seat of the chair, I felt the paddle tap my left cheek twice, disappear, and then a gunshot of sound and pain exploded in the room. It was followed by countless more as I struggled to stay in position. It probably only lasted a minute or two but it felt like an eternity. I questioned every decision that brought me to be naked in her messy little living room. 

To ground me in the moment and the real (though pretend) reason for why I was there, she asked rhetorically, "Do you think this is a little bit of how Cindy was feeling today?" Then, not waiting for an answer, "I am going to make sure you regret taking that poor little girl's virginity. Even with that little tiny penis of yours, I am sure that you hurt that little girl." 

With a flourish, it was suddenly over and the only sound in the room was her heavy breathing from the exertion and my mewing little boy getting spanking ouchy noises: ow, sorry, no, .... She never lets me recover and quickly directed me to the first chore: load and start the dishwasher. It is strange that I pay her but I'm the one that cleans the apartment. Our little sessions end usually when we are either out of time or more commonly, when her apartment is clean. It was pretty messy so I was thinking my bottom was in for a rough night. 

I was back in position after the dishwasher for a repeat with the paddle. The sting hadn't lasted long from the first round. This is part of the pattern where she works the meaty parts of my bottom until there is a lingering burning sting and then she moves on to other implements and techniques. 

I cleaned the kitchen (oval warmup paddle) and then vacuumed the living room (leather tawse), made her bed (more with that stingy wicked tawse), and even dusted (the tawse again though I was begging for anything else). Then I got working on the bathroom. The bathroom cleaning was interrupted by sessions with a medium size wooden spoon. She uses it to spread out the sting to the places that a flat paddle and that evil piece of leather just can't get to like down and inside my crack. During every spanking, she talked to me about Cindy. I heard how she could have gotten pregnant, how she was hurt, and how she wouldn't be virgin on her wedding night. It was awful hearing what a terrible person I could have been. 

My bottom was already sore and swollen when the punishment paddle came out while I was working on the bathroom. Mommy asked me to be sure to scrub the toilet and I said I would but I didn't say 'mommy' in the sentence. It is a strict rule when I answer a command: I have to call her 'mommy' every single time. I didn't notice the mistake until I came out after doing that chore (and doing it quite well, if I may say so myself) and saw the punishment paddle out next to the spoon. 

It is a terrifying implement consisting of a heavy hard wood oval that can cover an entire butt cheek. To add to its effectiveness, holes are drilled through it. The first infraction calls for two swats on each cheek and though that is a chilling thought, each infraction adds two more to the count. One time I was so bad that I got the punishment treatment four times. I started crying before the last session and mommy rubbed my back and whispered sweet things to me before giving me eight quick and hard spanks on first my right cheek and then eight more on my left. It was over in less than thirty seconds but left me in ruins. 

Four spanks with the monster wouldn't be too bad but she was in good form and I wasn't recovering between spankings anymore. At the beginning, the sting dissipates during the chore and I go into the next spanking like it was the first. After a few trips over the back of the chair, I start to feel the sting during the entire choir. After a few more, I am positively dragging my feet. My bottom already was burning and the sight of the punishment paddle ripped the apologies from my throat.

"Mommy, no, I'm sorry, mommy. Please mommy not the punishment paddle. I'll be good, I promise. Please mommy, no punishment paddle," I pleaded. I do plenty of pleading during my spanking time anyway but this was more desperate. Perhaps it was the memory of the night with so many punishment extras that made me so scared. Or possibly it was just that my bottom had taken a real beating already. Either way, she wasn't moved and, in fact, looked very pleased with herself for getting such a reaction out of me. 

"I'm sorry too, baby, but you didn't call me 'mommy' and we just can't have that. I have to give you extra punishment spanks or you just won't learn," she patiently explained to the little boy standing before her. "I think this lack of respect for your mommy is the same lack of respect you had for Cindy today so we are going to have extra spanks with the punishment paddle tonight. I think six on each cheek will do it. A nice even dozen." 

And that is when I realized that my fantasy was coming true. What I really wanted to be was broken, controlled, and pushed beyond what I could handle. It was more than the pain. The game was getting real and though I could say the safe word, if I stayed in the game, I was going to go to a place that I craved but didn't understand. Something was happening and if I let it, the punishment was going to be real for the first time. 

"Come on, baby, let's have your regular spanking first and then we'll take care of your punishment spanks," she said patting the chair. 

I shuffled closer slowly and heard myself say, "I'm scared, mommy," in a voice of a little boy about to cry. She took a step toward me, took my hand, and pulled me the last couple steps to the spanking chair. Instead of helping me over it, she instead pulled me close and hugged me tight. Never before had she done this and I let myself melt into her maternal arms. At first my penis hung free between us but her firm but gentle right hand rested on my left bottom cheek and she pulled me close and then patted the abused flesh. I let myself be hugged by my mommy. Her breasts pushed against my naked chest and my mostly soft penis pressed against stomach. 

"Baby, mommy has to give you a big spanking now. Your boom-boom is going to hurt real bad. You can cry if you need to. Spankings are supposed to hurt and everybody cries sometimes. You were very naughty today. That little girl cried because of you, right? I think you should cry too." 

It was all folding in on me for some reason. I was finally paying for all the 'naked games' I played when I was younger but it was like the weight was being lifted off me. All I had to do was let it go and accept my punishment instead of fighting it. I sniffled into her neck and it was like the sound triggered a chain reaction. I felt my face contort as I started to cry. "There-there, baby," she said patting my bottom for just a few seconds before pushing me away and helping me over the back of the chair. 

The world was all watery from the tears in my eyes and with my head down it was worse because the tears had nowhere to go. I felt a wooden spoon tap my bottom and her left hand caress my middle back and then push down slightly as if to hold me in place. A sob escaped me a second before the spoon produced purifying fire. 

My ouchy noises were louder than ever and mixed with crying as she reignited the fire on my bottom. I gripped the chair and danced my feet but stayed in position. In fact, I was at peace staying right there and letting it happen to me. It needed to happen even though it burned and stung with mind-erasing intensity. 

Then there was a pause and a new larger and heavier tapping on my bottom replaced the stingy spoon. Her left hand pressed down harder on my back and the wood disappeared from my bottom. "Hold still, baby," she said before the punishment paddle crashed into my bottom. Twelve quick but very hard strokes were over in seconds leaving the only sound in the room that of a well-spanked child crying. I was suddenly in her arms again but only briefly before she led me to her couch where she sat me down on the rough fabric. I wasn't looking at her so I didn't see her take off her dress before she sat down to my left. 

She pulled my shoulders so that I was facing to my right away from her and then pulled me back so that I would be lying on my back on her lap. "Put your legs up on the couch darling and just lay back on mommy's lap," she encouraged. I did and then rolled a little to hug her only to feel a naked breast on my face. I almost forgot about the rough fabric of the cheap couch torturing my bottom as I twisted. "Here you go, sweetie. Nursing always made you feel better when you were a baby," she said guiding my mouth to her nipple. 

We were never sexually involved and this seemed pretty close to the line but I was afraid to disobey here so I put her dark nipple to my lips and started to gently suck. She gasped but held me tight with her left hand. She cooed, "its OK, baby. You were so brave. That was such a hard spanking. Mommy is very proud of her little boy." Her breathing betrayed her own arousal. 

I tried to nurse on her breast like a baby but curiosity got the best of me and I explored her nipple and areola with my lips, tongue and teeth. I was suckling on her for only seconds before I felt her right hand on my thigh, then scrotum and then on my still very soft penis. He was still slippery and covered with pre-cum even though not erect any more. She gently fondled me and whispering encouragement: "that's right, baby. Let mommy nurse her little boy." I felt her shiver. 

Her words were stuttering a little as she taunted me, "see baby, this is why you need to wait to have sex. You are just a little baby yourself." I was probably a combination of the stimulation of her nipple, the hardening penis in her hand, and the power of a grown man, but she was clearly enjoying herself. "Is nursing from mommy making you feel better?" she asked breathlessly. I nodded and moaned. "Of course it does. Nursing always makes little ones feel better even after big spanking on their botty. Oh, and now your pee-pee is getting hard again. Mommy knows how to make baby's pee-pee nice and hard. It is so slippery; just covered with tears like your face is too. You've both been crying a lot. 

"Mommy had to spank you for being so naughty today. We can't let you be a naughty boy. You have to be punished when you are bad and you were very bad today rubbing your penis on little Cindy's tickle. You aren't old enough to do that. You need to have a big penis with hair all around it before you have sexy time with girls. This little pee-pee isn't ready to satisfy even a little girl and certainly not a woman. No, not yet." 

She sighed again and said, "baby nurses so nice but I think that breast is all done." She twisted away from my mouth and used the hand that had been holding tight to pull me away. Then, taking her right hand off my now completely hard penis, she guided her right nipple to my mouth and sighed deeply as I started to suckle eagerly. "Good boy," she breathed returning her hand to my bobbing penis. With her left hand, she held me tight again. 

"I think your pee-pee is ready to make squirties, isn't it?" she asked. I moaned the obvious answer. I was indeed enjoying her ministrations. "Mommy knows how to make her little boy feel better but because you were naughty, I can't let you squirt like this. Naughty boys only make squirties with spankees, right?" I groaned. "I know baby's botty is already very ouchy. More spankees are going to make it really sting but that will help you wiggle and squirt. Then you can clean up mommy's lap. That will be nice, won't it?" she asked knowing that I hate that part. I just groaned and tried to concentrate on her fingers softly gliding up and down my shaft. 

Then her hand was gone and she was pulling my mouth from her breast. The nipple popped out of my mouth and I moaned with disappointment. "Get up and bring mommy the hairbrush," she said with a little more joy than I was happy with. I got up slowly on shaky legs and immediately had a head rush and stumbled over to my spanking bag, crouched down and searched through it for the most conflicting spanking item. Something about this little brush makes for a blistering and blinding spanking but when my bottom is being spanked with it, I almost always have a fun little squirt and sometimes the squirt feels really good. 

When I turned around, my naked mommy was facing me but bent over in front of the spanking chair straightening out a towel on the floor. She stood up straight and my eyes stared straight at her crotch. Her pubic hair was trimmed but was long enough to still obscure what hid beneath. Still, her young frame was beautiful, feminine, and sensuous. She sat down primly and patted her thigh. Pointing at a bottle on the table right by me, she said, "bring over the slippery and make mommy's lap ready." 

I picked up the bottle, walked over, handed her the brush, and then froze staring at her naked lap. "Go ahead, sugar, make mommy's lap all slippery. It will feel good and make it easier for you to make squirties during your spanking." 

I knew all this, of course, but she was enjoying torturing me, I think. I knelt down, popped open the top and squirted the strawberry scented lube on first her right and then left thigh. I tried to gauge where about I would be making contact with her and focusing there. I didn't want to be inappropriate and put lube too close to her sex. Using my right hand, I spread the lube in a thin layer over her thighs. She took my hand in hers and brought it closer to her vagina. "Make sure you cover everywhere. I know how you wiggle when you get a spanking on my lap." I complied and even squirted a little more lube on her thighs. My fingers just grazed her pubic hair. 

"OK?" I asked. She nodded and asked, "are you ready to make?" 

I tried to look away but ended up just staring at the oily dark skin of her thighs and that mysterious tuft of black hair between them. I nodded shyly and whispered, “yes, mommy.” 

"Good boy," she cooed. "I'm going to give you a big spankee so that you make big squirties and when they are all out, it is going to be super ouchy. You are going to do some crying, I think but when it is over, I want you to clean up your messy like a good boy. Do a good job or I will put you right back over my lap. Understand?" 

In spite of the beautiful woman sitting naked in front of me, the promise of more punishment on my already very tender and abused bottom caused me very real concern. I remained in character but protested, "no, please, mommy, I just want to make stickies. No more ouchies. Please, mommy." My whining sounded childish and annoying in my own ears. 

She was patient but firm. "I know your boom-boom has had a lot of punishment today but mommy would be a bad mommy if she let her little boo-boo make squirts without a big ouchie spanking. You know little boys aren't allowed to make their squirties like big boys. You are just a naughty little boy." 

Her beautiful thighs had me mesmerized. I imaged what they would look like covered in my messy semen and what it was going to be like kneeling between them and licking it off. My penis pulsed excitedly. In spite of the impending torture awaiting my bottom, I nodded and whispered another breathless, "yes, mommy." 

"That's a good boy. It will all be over soon. 

"OK, over you go, baby." 

I was shaking with anticipation as I bent over her lap and slid effortlessly into place. She put her left around my waist and pulled me closer. I felt her left breast graze my back and the softness was electrifying. 

The wood of the hairbrush rested on my right cheek and I braced myself for what I knew was going to be a ferocious sting. I whined a last 'no' of protest as the hard wood tapped gently. 

I am terrible lover. My penis is a little shorter than average and on the thin side. I probably prematurely ejaculate three quarters of the time but sometimes I can go the distance and make my lovers happy. In spite of feeling like a hotdog in a hallway during vaginal intercourse, I still pop too quickly probably because of some biological drive to attempt procreation coupled with the sheer joy of finding a woman that will allow me to enter her. 

Anal sex is better because almost every woman is so tight. That is a rare treat for me and since I am so worried about hurting her, I seem to be able to hold out a little longer. 

Of course, if she is charitable enough to put my little guy in her mouth, it is an act of pure will to not immediately ejaculate. I always warn my lovers that if my penis is in their mouth, my semen will follow very soon after. One woman didn't believe me and laughed thinking that I was just being nice. To say she was surprised would be a gross understatement. It was our last date and clearly it ended poorly which upset me since I had been very honest. 

I say all this to make the point that I know what 'real' sex feels like; my mommy's thighs weren't the only lovers my penis had ever experienced. Still, they felt delicious, slippery and soft, but also uneven with the valley between them. I thought I could feel pubic hair on my shaft even but wasn't sure if that was just wishful thinking. My penis pulsed with anticipation and I tried to force myself not to start rutting right away. 

The wood disappeared and my need for stimulation overruled my stoic desire to prolong the moment. I dragged my raging erection across her skin and felt my bottom clench tight. The hairbrush crashed into my tensed muscles and I grunted in protest. The sting followed as did more spanks from the hard wood. I twisted and wiggled under the punishment. Soon, my bottom jiggled under each spank when I wasn't clenched tight and I was humping with abandoned trying to simultaneously escape the brush but also recapture the good feelings in the tip of my penis. 

My orgasm was upon me suddenly. I would love to say that it was mind-blowing fireworks but really it was more of a release. Like the ejaculation of a man being hanged, it was my body's last attempt at procreation. Semen sprayed from the tip of my penis onto the lap of my lover and I only registered the slightest tingling at the very tip as the thick liquid forced its way out. 

Sex was over and done. The good chemicals flooded my brain and mixed with the pain she was delivering. I went limp over her lap and felt my bottom cheeks jiggle and bounce with each strike. The hard wood lit a fire on my bottom that penetrated through my entire body. A boy was crying. All hope was lost. Fire consumed me. 

"OK, that's enough. Up you go," she said a second after the last gunshot of wood on swollen bottom cheek was heard. I was sobbing but knew better than to give her more opportunity to punish my naughty bottom. Struggling to my feet, I caught a glimpse of my sticky ejaculate stretch like glue between us for a fraction of a second. 

Crying still but quietly I stood on wobbly feet beside her and inspected the damage done to her beautiful thighs. Because she had pulled me close to her, I had indeed squirted my seed nearer to her crotch than normal. In fact, some of it was tangled in her pubic hair. Slowly and with ceremonious intention, she spread her legs revealing her young sex. Had I not spent myself seconds before, I would possibly had spontaneously ejaculated at the sight. Her dark skin shown through the sparse black pubic hair framing first deep dark red outer lips and then electric pink inner folds. Her clitoris poked out from under its protective hood like an erect penis. 

Her thighs were covered with semen and it was my final duty to lick them clean. Long ago I had admitted to her that this was something I hated but needed to do. Only once did I protest. I knew the penalty I was going to receive even for pausing not to mention ask for reprieve. Never again did I even pause. 

I was on my knees between her legs staring at her beautiful sex as much as I could as I started licking up the impossibly salty and tangy semen that thankfully also had just a hint of strawberry. With her hand on the back of my head she guided me in my task and forced me to complete it. As I felt the semen coating my soft, pale, and hairless genitals cool as it dried, she pulled me closer to her treasures and finally held me in place as she made me service her. 

It took less than a minute for her pleasure to be complete as well which surprised me because--like all of my skills with women--I am passable at best when it comes to cunnilingus. Perhaps it was the burning of my bottom or the threat of more that made me better that night. Perhaps she was excited by our game as well. Whatever the reason, I found myself with her clitoris between my lips as her muscles contracted under my chin and her still wet thighs covered in lube, semen and my saliva pressed hard against the side of my head as she groaned through her orgasm. 

She pulled me off of her when she had enough and I sat back staring at her beauty. I reached up to wipe my face but she stopped me. "No, baby, no cleaning up." Then, after a pregnant pause, "I want my boyfriend to see you." 

The doorbell rang and she said with a wink, "can you answer the door for mommy, please? You know how he doesn't like to wait."