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Anything Goes
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Bi-Sexual Male / 46
I've been with my girlfriend for three years now. We've been living together for over two years. Her son just recently turned 12. About six months ago, I noticed the tell tale signs of masturbation. It started with long self sequestering in the bathroom. That was followed by asking me to install a lock on his bedroom door. Then long periods of loud music coming from his room. Other signs were crusty underwear in the laundry, stains on his sheets and so on. I consulted his mom who had no understanding of male puberty. I gave her a crash course and she decided to turn his sexual education over to me and was glad to be relieved of it. So wanting to be a good surrogate Dad I went out and bought a few sex education books. Two of them were intended to educate middle school students. The others were sexual guides for adults.
So I took him aside and sat him down for the talk that most adults dread. His mother would be at work all day so I had plenty of time to do it right. I told him he didn't have to say anything. I told him I was just going to give him a short lecture on the mechanics of reproduction concentrating first on where babies come from then going over various types of contraception and ways to protect oneself from diseases. So once the basic lecture was done with I opened the bag I had and pulled out the sex education books. I showed him the two intended for middle school kids and then I showed him the ones intended for adults. I explained he should read the middle school texts first then read the more advanced ones. Then I asked if he wanted the advanced ones or just the middle school ones and he just said both and I put them on his dresser. Next I pulled out of my back three packages of condoms. I put them on his dresser and explained that they were three different sizes. I told him that there were instructions on how to use them in the boxes and that he should experiment with the the different sizes to make sure he was getting a proper fit. I reminded him that his penis would get much bigger as he got older older so he would need larger condoms as he got bigger. I told him that 90% of all boys jerked off and the other 10% are lying. He laughed at that. It was nervous laughter. That's OK. The whole conversation was awkward but after a while we both relaxed.
I then pulled out a bottle of lube and explained what that was for. I explained that using a condom while jerking off meant that the sheets would not get messy and his mom wouldn't see his cum stains on the sheets. I explained a lot of things about sex and boyhood. One of the things I explained was that all boys go through a period, mostly their teenage years, where half the time they would be walking around with a hard-on and there pretty much was nothing they could do about it. I told him he would probably feel embarrassed about it and yes girls did notice and were probably giggling to themselves about it but also often girls were curious and sometimes enjoyed looking at those tented front of pants.
Then I told him what my profoundly wise uncle told me. When I was 11 my uncle explained to me several things a boy entering puberty could do to increase his penis size. What few adults know and fewer are willing to share with a boy entering puberty is that there are several things a boy can do during puberty to enhance his penis size. I explained that frequent masturbation encouraged an increase in testosterone production and that in turn causes an increase in penis size. I explained that using a penis pump repeatedly throughout puberty would result in a larger penis. Then I pulled out of my bag a penis pump. I explained that this model was for smaller penises and that it had all the instructions in the box I told him they were good for about a year before they needed to be replaced. I told him I would get him a new one every year for as long as I knew him. I told him about the various supplements and vitamins he should take during puberty to enhance penis size. These are secrets that nobody ever wants to tell a boy in puberty. I also told him about avoiding foods with plant estrogen that inhibit penis growth. Mostly wheat flower but there are other foods that have plant estrogen as well. While it's not a huge influence on penis size it does have a minor adverse affect
My next lecture topic was on how to seduce girls. Mostly I told him to keep in shape, continue his involvement in athletics, never take up smoking, drugs or alcohol. I lied to him and told him that all three would stunt penis growth. I figured that sort of white lie wouldn't hurt. I told him to mostly just be himself and that if he kept himself in shape girls would notice him. I told him even if he is shy (he is shy) that girls would approach a good looking athletic boy. I told him about the importance of hygiene since girls don't like guys that smell like a locker room. And then just to make sure I covered all bases, I explained that if it turned out he was gay, the same rules applied and that yes it was O.K. if he turned out to be gay and his mother felt the same way. I then went on to explain that boys his age often felt bisexual and later would discover their true sexuality, either gay or straight or bi and that the only correct choice was to choose to be his real self whatever that was and to be happy with it.
I gave him a lot of practical advice like suggesting he NOT send naked pictures of himself to anyone since he could go to jail even if he only took them of himself. I then explained all sorts of sexy poses he could do that would not be illegal and how to tell the difference.
So figuring I was done with that very long lecture I got up and stretched my legs and suggested we brake for lunch. We sat out back on the patio eating sandwiches. I had on shorts and a t-shirt. He had shorts on and nothing else. I couldn't help but notice how beautiful he was with his long blond hair down his shoulders and almost reaching his nipples. I couldn't help but notice his beautiful blue eyes and long lashes and kissable lips. I restrained myself but felt my cock get hard in my shorts. After lunch we stood up to bring our stuff inside and noticed when he stood up he had a tent in the front of his pants. He made no effort to hide it but I discretely hid my erection.
After lunch we sat back down on his bed and I offered to answer any questions he might have. I honestly figured he would pass on the questions and suggest I leave so he could explore those books which admittedly would seem somewhat pornographic to a typical twelve year old boy. To my surprise he immediately asked me how old I was the first time I jerked off. I told him I was 12 the first time. He then told me he had started at ten when the older brother of a friend told him how to do it. I was not expecting that little confession. He admitted to watching internet porn while he jerked off. He reached over and handed me back one of the boxes of condoms and said he already knew his correct size and that he would not need the smallest size. That was quite a surprise that he had any idea about condom sizes. I didn't bother asking how he acquired that knowledge.
If I thought things were going in a surprising direction I was in for even more shocks. He asked me if I was bisexual. I told him yes. He asked me if I was sexually attracted to boys his age. I figured what the hell and answered honestly. I said yes. He asked if it was normal for 12 year old boys to want to have sex with men old enough to be their dad. How naive of me not to realize what he was getting at. I told him it was probably not common but that it was probably not unheard of. I told him there was no such thing as normal or abnormal when it came to sexual desire. I asked if he had any more questions but he said no. So that was it as far as I was concerned but I started to get the impression that he was hinting at wanting to get intimate with me. Assuming that I was mistaken I decided not to explore or pursue that possibility.
The next day he practically dragged me into his room and locked his door behind us. His mother was at work again so we were alone. He showed me a porn website specializing in "twinks" and asked me if he was a twink. I explained the definition and that yes in a way he was but that it might be more accurate to say he was jailbait and explained what that meant. Next he clicked on a link in his book marked web sites and that took him to another gay porn site, this one specializing in videos of young boys and their "Dads" in simulated i****t scenarios. The boys were all over 18 but were very short, slender and mostly looked like they could pass for still being in puberty, some looked as young as 12 but the site guaranteed all the boys were over 18. The "Dad's were all in their 40's to 60's and all were big and muscular and had big cocks. On the front page was a little boy with long blond hair mounted on his "Dad's" huge cock. They were in a 5 second loop fucking endlessly. The "Dad" had a mean look on his face and was grunting. The "son" had a look of adoring bliss on his face as his ass was being pile driven. I got hard instantly. Then he asked me if I had ever fucked a boy his age in the ass. I told him no that I hadn't but that when I was in high school I had fucked a 14 year old boy in the ass and that I was 17 at the time. Not such a huge age difference but enough that had I got caught I would have gotten in trouble for it if caught. Luckily I was never caught. He asked how old I was the first time I got fucked in the ass. I told him I was in my twenties. He asked if it hurt. It old him the first time in the ass often did but that if a guy practiced with a well lubricated dildo he can stretch his ass so he could take a dick there. He shocked me yet again by asking if I would get him a dildo to practice with. I told him yes and later bought him three sizes of penis shaped dildos and a set of five different sizes of butt plugs and an extra bottle of lube. I figured what the hell. If he wanted to fuck his own ass he should be allowed and if he really wanted to be some old bear's twink fuck hole he should at least be properly prepared for it. I noticed his dick was hard throughout the whole conversation. I also noticed he sneaked his had between his legs constantly and being less and less discrete about it. Finally I stood up and told him he was naughty for doing that in front of me and that from now on every time he plays with himself in front of me I would punish him by scolding him for doing that. It was like a light bulb going off. He stood up, pulled his pants down and jerked off in front of me. I kept my word and punished him by scolding him throughout the entire process. I told him he was a naughty pervert fag and repeatedly berated him the whole time telling him how bad he was and naughty he was. When I got verbally vicious and interrogated him asking why he was jerking off in front of me and why he was such a pervert and fag and asked him why he liked to suck cock and asked why he wanted me to fuck him in the ass he just convulsed and screamed and shot his load across and it landed on me. Of course I was watching very up close so naturally I got some on my face. But I truly didn't think a 12 year old could shoot that much and so far. In fact I was a little surprised he shot out anything at all. When he was done and had caught his breath I told him it was O.K. and that he was not in any real trouble. I told him I could not actually have sex with him but any time he wants to jerk off in front of me like that I would scold him in exactly the same way.
So for the next few days, every time his mom left for work, he would invite me into his bedroom and then he stripped down naked and jerked off in front of me while he had some gay porn video playing on his computer. Mostly the gay porn involved some middle aged man fucking an 18 year old boy that looked like a little 12 year old boy. He just stood there naked and I went right into scolding and berating and interrogating and each time he got more involved in the whole thing and then started to confess to having committed the most bizarre and wild gay sex acts. Of course I realize it was all him expressing his fantasy desires so I went along with it "punishing" him as we went along. At one point he started to chant "I'm a faggot, I'm a gay, homosexual, cock sucking sissy faggot." He just blurted it out and repeatedly chanted that and variations while I said "yes you are you naughty little pervert sissy faggot" and he would come on my face, at this point I was kneeling in front of him to get a really good view. No touching but it was sure nice watching his streams of cum squirting on my tongue or in my eyes. After I ran to my room and jerked off frantically while watching the same video imaging I was fucking the living shit out of that gorgeous little prick tease.
A couple of weeks after all this started after inviting me into his room and locking the door as usual and after he stripped down naked and standing there with his adorable little hard on bobbing up and down he simply said "would you please spank me?" I asked him what he had done to be so naughty that he deserved to be punished. At that point yet again, he shocked me. He confessed that, that morning when he woke up he jerked off, without my permission and while he did that he watched a video of a man fucking his real son and that he fantasized about me being his real dad and fucking him in the ass. He said that in his fantasy he magically transformed into a girl and that I then fucked him in his pussy and that I made him pregnant. He said to me that he truly was a very naughty sissy faggot and said he deserved a severe spanking. So I agreed to spank him. He jumped up on my lap laying across it so his erect dick was right at my crotch and pressing against my erection through my pants. I looked down and saw his ass was already red. I asked him about it and he hopped up off my ass and pulled a leather belt out from under his sheets. He said he had been whipping his own ass and crotch with it while imagining that I had tied him up naked and was whipping him all over with it.
I damned near came in my pants after that confession. It's one thing to spank a naughty little sissy faggot but to whip him with a belt, I felt that was going too far so I told him to put the belt away and proceeded to give him an old fashioned over the knee spanking sans belt. He actually wore me out. I thought he would cry uncle. I stopped counting after 200 strokes. My arm began to ache so I just gave up. He looked up at me with a look of disappointment on his face. I could not believe he was actually enjoying what I considered abuse. I had told him before it started that he could stop the spanking at any moment by calling out the word "red." He never said a word but only grunted. When he got up I could tell that at some point he had cum all over my shorts.
A few days after that incident, after his mother had gone off to work, he strutted out into the living room, his hair in pigtails, lipstick on his lips, fingernail polish, and he was wearing his mom's bra, panties, garter belt, stockings and pumps, all black. He turned around and bent over to show me one of the butt plugs shoved all the way up his ass. He told me he was a very naughty girl and needed a spanking. without any further words he hopped up onto my lap. I could see only the very end of the butt plug sticking out of his ass. The rest of the six inch plug was deep inside his bowels. He arched his back in anticipation and so I proceeded to spank him. With each stroke I could feel my hand slam into the end of the butt plug which must have sent reverberations up his ass with every stroke. He grunted with every stroke but never yelled out his save word. Again I gave up before he did. But this time he hadn't cum from the spanking. He walked back into his room and a moment later he came back out. He was walking funny but in a funny way that he was obviously getting off from. He then folded the belt in half and commenced whipping himself between the legs with the loop of the heavy leather belt and just grunted out all manner of vile perverted confessions. I followed his lead by tailoring my berating and scolding him to whatever he was confessing to at the moment. I wanted to grab that belt from him and whip him to within an inch of his life for making me so horny and wanting to fuck his tight little ass. but I restrained myself and just limited my self to extreme verbal assaults. He shot his load just as he was describing the three foot long six inch thick black cock he planned to choke himself to death on. Again I sat on the floor and kept my mouth wide open with my tongue out to catch the cum. I was amazed that he had made himself cum by beating his groin with that belt and not by jerking off.
I'm kind of handy and had toyed with the idea of designing and building a testicle beating machine. But until now I have not found a willing partner to play with. My girlfriend's son has inspired me. So what I did was I went out and bought an electric fan. I took it apart and took off the blades. I altered them and then remounted them so they were at a different angle. Now they are like paddles on a central axis. With the guard off and the blades turned at a different angle like that if a man or boy were to squat over them lowering their testicles into their path as the fan was spinning, their balls would get paddled at a rate of about 900 strokes a minute or about 15 strokes per second. I showed my new invention off to the lad and I thought he was going to cum just from looking at it. He immediately figured out what it was for and how it worked. He plugged it in and turned the dial all the way to the highest setting and squatted right down over it. It took about two seconds for his testicles to retracted right up into his groin. He liked it obviously by the smile on his face but I think his balls were less than enthused. He stood up and ran back into his room and was gone for a few minutes. He strutted back into the room led by his bobbing throbbing little cock and sporting a pony tail elastic bound around his scrotum. His balls stuck out prominently unable to escape their impending fate. He squatted back down over the ball bashing machine and it sounded like a machine gun going off. It took about fifteen seconds of him screaming and his balls being beaten by my little machine for him to shoot his load further than I ever saw him shoot it. He never even touched his cock. He fell over right after than tipping the machine over as he did. I shut it off and set it aside and examined him. He was out cold. I was scared that I had done something horrible to him. I was also concerned about having the flow of blood cut off his little balls. So unable to arouse him and not wanting to castrate the little pervert I bent over and retrieved the pony tail elastic from his scrotum. I figured that, that was an acceptable excuse for touching his private parts without getting into too much trouble.
A few minutes later he came to. He immediately threw his arms around me in a tight embrace, told me he loved me and that was the most "awesomest" thing that ever happened to him. He described it as a handgrenade of orgasm exploded between his legs. He said it was the most painful thing he had ever experienced and at the same time was the best feeling he had every felt. It looks like I had create a monster, a little hyper masochistic pervert monster.
But it seems my little pervert protegee no longer needs my assistance. now his daily routine is as follows. He waits for his mom to go to work. He opens his bedroom door wide open. Yells out a few confessions at the top of his lungs, lowers himself onto the ball beating machine, screams for a moment or two then goes silent collapsing to the floor in a fetal position. This happens half a dozen or so times a day now. I have warned him that if he doesn't cut back on smashing his balls he's going to end up destroying them and lose all sexual desire and essentially he would become a eunuch. He told me that would make it easier for him to turn into a girl. He expressed a desire for me to kick or stomp on his balls to destroy them and I told him that if he wanted them destroyed he has to do it himself.
I have to admit though, it is awfully fun listing to his screams from his room while I lay in bed in my room jerking off to those delightful sounds imaging just how much fun it would be to take a hammer to his balls fulfilling the little sissy fagot's ultimate wish.
So I took him aside and sat him down for the talk that most adults dread. His mother would be at work all day so I had plenty of time to do it right. I told him he didn't have to say anything. I told him I was just going to give him a short lecture on the mechanics of reproduction concentrating first on where babies come from then going over various types of contraception and ways to protect oneself from diseases. So once the basic lecture was done with I opened the bag I had and pulled out the sex education books. I showed him the two intended for middle school kids and then I showed him the ones intended for adults. I explained he should read the middle school texts first then read the more advanced ones. Then I asked if he wanted the advanced ones or just the middle school ones and he just said both and I put them on his dresser. Next I pulled out of my back three packages of condoms. I put them on his dresser and explained that they were three different sizes. I told him that there were instructions on how to use them in the boxes and that he should experiment with the the different sizes to make sure he was getting a proper fit. I reminded him that his penis would get much bigger as he got older older so he would need larger condoms as he got bigger. I told him that 90% of all boys jerked off and the other 10% are lying. He laughed at that. It was nervous laughter. That's OK. The whole conversation was awkward but after a while we both relaxed.
I then pulled out a bottle of lube and explained what that was for. I explained that using a condom while jerking off meant that the sheets would not get messy and his mom wouldn't see his cum stains on the sheets. I explained a lot of things about sex and boyhood. One of the things I explained was that all boys go through a period, mostly their teenage years, where half the time they would be walking around with a hard-on and there pretty much was nothing they could do about it. I told him he would probably feel embarrassed about it and yes girls did notice and were probably giggling to themselves about it but also often girls were curious and sometimes enjoyed looking at those tented front of pants.
Then I told him what my profoundly wise uncle told me. When I was 11 my uncle explained to me several things a boy entering puberty could do to increase his penis size. What few adults know and fewer are willing to share with a boy entering puberty is that there are several things a boy can do during puberty to enhance his penis size. I explained that frequent masturbation encouraged an increase in testosterone production and that in turn causes an increase in penis size. I explained that using a penis pump repeatedly throughout puberty would result in a larger penis. Then I pulled out of my bag a penis pump. I explained that this model was for smaller penises and that it had all the instructions in the box I told him they were good for about a year before they needed to be replaced. I told him I would get him a new one every year for as long as I knew him. I told him about the various supplements and vitamins he should take during puberty to enhance penis size. These are secrets that nobody ever wants to tell a boy in puberty. I also told him about avoiding foods with plant estrogen that inhibit penis growth. Mostly wheat flower but there are other foods that have plant estrogen as well. While it's not a huge influence on penis size it does have a minor adverse affect
My next lecture topic was on how to seduce girls. Mostly I told him to keep in shape, continue his involvement in athletics, never take up smoking, drugs or alcohol. I lied to him and told him that all three would stunt penis growth. I figured that sort of white lie wouldn't hurt. I told him to mostly just be himself and that if he kept himself in shape girls would notice him. I told him even if he is shy (he is shy) that girls would approach a good looking athletic boy. I told him about the importance of hygiene since girls don't like guys that smell like a locker room. And then just to make sure I covered all bases, I explained that if it turned out he was gay, the same rules applied and that yes it was O.K. if he turned out to be gay and his mother felt the same way. I then went on to explain that boys his age often felt bisexual and later would discover their true sexuality, either gay or straight or bi and that the only correct choice was to choose to be his real self whatever that was and to be happy with it.
I gave him a lot of practical advice like suggesting he NOT send naked pictures of himself to anyone since he could go to jail even if he only took them of himself. I then explained all sorts of sexy poses he could do that would not be illegal and how to tell the difference.
So figuring I was done with that very long lecture I got up and stretched my legs and suggested we brake for lunch. We sat out back on the patio eating sandwiches. I had on shorts and a t-shirt. He had shorts on and nothing else. I couldn't help but notice how beautiful he was with his long blond hair down his shoulders and almost reaching his nipples. I couldn't help but notice his beautiful blue eyes and long lashes and kissable lips. I restrained myself but felt my cock get hard in my shorts. After lunch we stood up to bring our stuff inside and noticed when he stood up he had a tent in the front of his pants. He made no effort to hide it but I discretely hid my erection.
After lunch we sat back down on his bed and I offered to answer any questions he might have. I honestly figured he would pass on the questions and suggest I leave so he could explore those books which admittedly would seem somewhat pornographic to a typical twelve year old boy. To my surprise he immediately asked me how old I was the first time I jerked off. I told him I was 12 the first time. He then told me he had started at ten when the older brother of a friend told him how to do it. I was not expecting that little confession. He admitted to watching internet porn while he jerked off. He reached over and handed me back one of the boxes of condoms and said he already knew his correct size and that he would not need the smallest size. That was quite a surprise that he had any idea about condom sizes. I didn't bother asking how he acquired that knowledge.
If I thought things were going in a surprising direction I was in for even more shocks. He asked me if I was bisexual. I told him yes. He asked me if I was sexually attracted to boys his age. I figured what the hell and answered honestly. I said yes. He asked if it was normal for 12 year old boys to want to have sex with men old enough to be their dad. How naive of me not to realize what he was getting at. I told him it was probably not common but that it was probably not unheard of. I told him there was no such thing as normal or abnormal when it came to sexual desire. I asked if he had any more questions but he said no. So that was it as far as I was concerned but I started to get the impression that he was hinting at wanting to get intimate with me. Assuming that I was mistaken I decided not to explore or pursue that possibility.
The next day he practically dragged me into his room and locked his door behind us. His mother was at work again so we were alone. He showed me a porn website specializing in "twinks" and asked me if he was a twink. I explained the definition and that yes in a way he was but that it might be more accurate to say he was jailbait and explained what that meant. Next he clicked on a link in his book marked web sites and that took him to another gay porn site, this one specializing in videos of young boys and their "Dads" in simulated i****t scenarios. The boys were all over 18 but were very short, slender and mostly looked like they could pass for still being in puberty, some looked as young as 12 but the site guaranteed all the boys were over 18. The "Dad's were all in their 40's to 60's and all were big and muscular and had big cocks. On the front page was a little boy with long blond hair mounted on his "Dad's" huge cock. They were in a 5 second loop fucking endlessly. The "Dad" had a mean look on his face and was grunting. The "son" had a look of adoring bliss on his face as his ass was being pile driven. I got hard instantly. Then he asked me if I had ever fucked a boy his age in the ass. I told him no that I hadn't but that when I was in high school I had fucked a 14 year old boy in the ass and that I was 17 at the time. Not such a huge age difference but enough that had I got caught I would have gotten in trouble for it if caught. Luckily I was never caught. He asked how old I was the first time I got fucked in the ass. I told him I was in my twenties. He asked if it hurt. It old him the first time in the ass often did but that if a guy practiced with a well lubricated dildo he can stretch his ass so he could take a dick there. He shocked me yet again by asking if I would get him a dildo to practice with. I told him yes and later bought him three sizes of penis shaped dildos and a set of five different sizes of butt plugs and an extra bottle of lube. I figured what the hell. If he wanted to fuck his own ass he should be allowed and if he really wanted to be some old bear's twink fuck hole he should at least be properly prepared for it. I noticed his dick was hard throughout the whole conversation. I also noticed he sneaked his had between his legs constantly and being less and less discrete about it. Finally I stood up and told him he was naughty for doing that in front of me and that from now on every time he plays with himself in front of me I would punish him by scolding him for doing that. It was like a light bulb going off. He stood up, pulled his pants down and jerked off in front of me. I kept my word and punished him by scolding him throughout the entire process. I told him he was a naughty pervert fag and repeatedly berated him the whole time telling him how bad he was and naughty he was. When I got verbally vicious and interrogated him asking why he was jerking off in front of me and why he was such a pervert and fag and asked him why he liked to suck cock and asked why he wanted me to fuck him in the ass he just convulsed and screamed and shot his load across and it landed on me. Of course I was watching very up close so naturally I got some on my face. But I truly didn't think a 12 year old could shoot that much and so far. In fact I was a little surprised he shot out anything at all. When he was done and had caught his breath I told him it was O.K. and that he was not in any real trouble. I told him I could not actually have sex with him but any time he wants to jerk off in front of me like that I would scold him in exactly the same way.
So for the next few days, every time his mom left for work, he would invite me into his bedroom and then he stripped down naked and jerked off in front of me while he had some gay porn video playing on his computer. Mostly the gay porn involved some middle aged man fucking an 18 year old boy that looked like a little 12 year old boy. He just stood there naked and I went right into scolding and berating and interrogating and each time he got more involved in the whole thing and then started to confess to having committed the most bizarre and wild gay sex acts. Of course I realize it was all him expressing his fantasy desires so I went along with it "punishing" him as we went along. At one point he started to chant "I'm a faggot, I'm a gay, homosexual, cock sucking sissy faggot." He just blurted it out and repeatedly chanted that and variations while I said "yes you are you naughty little pervert sissy faggot" and he would come on my face, at this point I was kneeling in front of him to get a really good view. No touching but it was sure nice watching his streams of cum squirting on my tongue or in my eyes. After I ran to my room and jerked off frantically while watching the same video imaging I was fucking the living shit out of that gorgeous little prick tease.
A couple of weeks after all this started after inviting me into his room and locking the door as usual and after he stripped down naked and standing there with his adorable little hard on bobbing up and down he simply said "would you please spank me?" I asked him what he had done to be so naughty that he deserved to be punished. At that point yet again, he shocked me. He confessed that, that morning when he woke up he jerked off, without my permission and while he did that he watched a video of a man fucking his real son and that he fantasized about me being his real dad and fucking him in the ass. He said that in his fantasy he magically transformed into a girl and that I then fucked him in his pussy and that I made him pregnant. He said to me that he truly was a very naughty sissy faggot and said he deserved a severe spanking. So I agreed to spank him. He jumped up on my lap laying across it so his erect dick was right at my crotch and pressing against my erection through my pants. I looked down and saw his ass was already red. I asked him about it and he hopped up off my ass and pulled a leather belt out from under his sheets. He said he had been whipping his own ass and crotch with it while imagining that I had tied him up naked and was whipping him all over with it.
I damned near came in my pants after that confession. It's one thing to spank a naughty little sissy faggot but to whip him with a belt, I felt that was going too far so I told him to put the belt away and proceeded to give him an old fashioned over the knee spanking sans belt. He actually wore me out. I thought he would cry uncle. I stopped counting after 200 strokes. My arm began to ache so I just gave up. He looked up at me with a look of disappointment on his face. I could not believe he was actually enjoying what I considered abuse. I had told him before it started that he could stop the spanking at any moment by calling out the word "red." He never said a word but only grunted. When he got up I could tell that at some point he had cum all over my shorts.
A few days after that incident, after his mother had gone off to work, he strutted out into the living room, his hair in pigtails, lipstick on his lips, fingernail polish, and he was wearing his mom's bra, panties, garter belt, stockings and pumps, all black. He turned around and bent over to show me one of the butt plugs shoved all the way up his ass. He told me he was a very naughty girl and needed a spanking. without any further words he hopped up onto my lap. I could see only the very end of the butt plug sticking out of his ass. The rest of the six inch plug was deep inside his bowels. He arched his back in anticipation and so I proceeded to spank him. With each stroke I could feel my hand slam into the end of the butt plug which must have sent reverberations up his ass with every stroke. He grunted with every stroke but never yelled out his save word. Again I gave up before he did. But this time he hadn't cum from the spanking. He walked back into his room and a moment later he came back out. He was walking funny but in a funny way that he was obviously getting off from. He then folded the belt in half and commenced whipping himself between the legs with the loop of the heavy leather belt and just grunted out all manner of vile perverted confessions. I followed his lead by tailoring my berating and scolding him to whatever he was confessing to at the moment. I wanted to grab that belt from him and whip him to within an inch of his life for making me so horny and wanting to fuck his tight little ass. but I restrained myself and just limited my self to extreme verbal assaults. He shot his load just as he was describing the three foot long six inch thick black cock he planned to choke himself to death on. Again I sat on the floor and kept my mouth wide open with my tongue out to catch the cum. I was amazed that he had made himself cum by beating his groin with that belt and not by jerking off.
I'm kind of handy and had toyed with the idea of designing and building a testicle beating machine. But until now I have not found a willing partner to play with. My girlfriend's son has inspired me. So what I did was I went out and bought an electric fan. I took it apart and took off the blades. I altered them and then remounted them so they were at a different angle. Now they are like paddles on a central axis. With the guard off and the blades turned at a different angle like that if a man or boy were to squat over them lowering their testicles into their path as the fan was spinning, their balls would get paddled at a rate of about 900 strokes a minute or about 15 strokes per second. I showed my new invention off to the lad and I thought he was going to cum just from looking at it. He immediately figured out what it was for and how it worked. He plugged it in and turned the dial all the way to the highest setting and squatted right down over it. It took about two seconds for his testicles to retracted right up into his groin. He liked it obviously by the smile on his face but I think his balls were less than enthused. He stood up and ran back into his room and was gone for a few minutes. He strutted back into the room led by his bobbing throbbing little cock and sporting a pony tail elastic bound around his scrotum. His balls stuck out prominently unable to escape their impending fate. He squatted back down over the ball bashing machine and it sounded like a machine gun going off. It took about fifteen seconds of him screaming and his balls being beaten by my little machine for him to shoot his load further than I ever saw him shoot it. He never even touched his cock. He fell over right after than tipping the machine over as he did. I shut it off and set it aside and examined him. He was out cold. I was scared that I had done something horrible to him. I was also concerned about having the flow of blood cut off his little balls. So unable to arouse him and not wanting to castrate the little pervert I bent over and retrieved the pony tail elastic from his scrotum. I figured that, that was an acceptable excuse for touching his private parts without getting into too much trouble.
A few minutes later he came to. He immediately threw his arms around me in a tight embrace, told me he loved me and that was the most "awesomest" thing that ever happened to him. He described it as a handgrenade of orgasm exploded between his legs. He said it was the most painful thing he had ever experienced and at the same time was the best feeling he had every felt. It looks like I had create a monster, a little hyper masochistic pervert monster.
But it seems my little pervert protegee no longer needs my assistance. now his daily routine is as follows. He waits for his mom to go to work. He opens his bedroom door wide open. Yells out a few confessions at the top of his lungs, lowers himself onto the ball beating machine, screams for a moment or two then goes silent collapsing to the floor in a fetal position. This happens half a dozen or so times a day now. I have warned him that if he doesn't cut back on smashing his balls he's going to end up destroying them and lose all sexual desire and essentially he would become a eunuch. He told me that would make it easier for him to turn into a girl. He expressed a desire for me to kick or stomp on his balls to destroy them and I told him that if he wanted them destroyed he has to do it himself.
I have to admit though, it is awfully fun listing to his screams from his room while I lay in bed in my room jerking off to those delightful sounds imaging just how much fun it would be to take a hammer to his balls fulfilling the little sissy fagot's ultimate wish.


