“Hey, Mom. Look!” shouted my son Joey.
I turned my gaze away from his bare bottom, looked into his big brown eyes and said, "I'm watching, baby."
Joey turned his head back, leaned forward, and whispered something in Tommy's ear. The next thing I remember, Joey pulled his stiff, three-inch, hairless cock out of Tommy's ass. He detached himself between Tommy's legs so he could sit up. Then Tommy rolled onto his stomach and got down on all fours.
While Tommy was on all fours with his legs spread as wide as a nine-year-old could manage, Joey quickly slid over to Tommy and pushed his thin, 10-centimeter-long penis back into Tommy's already oiled asshole. Tommy and Joey giggled as my son's glans slid in.
They both groaned as his shaft soon followed. Joey thrust a little further until his testicles were pressed firmly against Tommy's tight, extra-small, hairless scrotum. I, too, let out a sigh of excitement as I watched the two begin to mate.
I'd been watching them fuck for months, but this time it was by far the most exciting. I suppose it was because with a little movement I could see their two young asses and, if I was in the right spot, even watch my son's cock slide in and out of Tommy's ass.
I looked more closely and saw that Tommy must really be enjoying it this time, because his five-centimeter-long, hairless, somewhat thicker penis was now throbbing as it waited for its turn with my son.
Joey thrust his cock firmly into Tommy's ass and then back out again. The angled position made it easy for him to forcefully push his small penis in and out. It seemed Tommy was enjoying the extra-hard fuck this time just as much as Joey. They both started moaning as their breathing quickened and their moans grew louder.
"Mom! I'm about to have that really awesome feeling!", my son shouted.
"Good." "Kid. Enjoy it to the end," I shouted back.
Soon my son was giving faster, short thrusts, and then one final, powerful thrust. He collapsed onto Tommy's back, breathing so heavily that I was afraid he would hyperventilate. Eventually, he regained control of his breathing and sat up, but with his cock still inside Tommy's ass and his hands on Tommy's buttocks, Tommy couldn't move.
"Joey, it's time to let Tommy have his turn." "You have to pull out now," I said to my son in a motherly voice.
He did as I wanted, taking his hands off Tommy's sweet, soft ass and pulling his penis out of his ass. Joey lay down, and Tommy quickly moved between my son's legs. They were back in the missionary position, but my son was on the bottom.
Tommy lubricated my son's bottom and his own small but nicely thick shaft before bending over my son's sexy 10-year-old body. Apart from the hair on their heads, these two kids were as hairless as the day they were born, just the way I like it.
Tommy wasn't as good in bed as my son, but it was still fun to watch him, especially when he was fucking my son's tight asshole. Tommy was a bit more loving and compassionate, though, which made up for his lack of skill.
Tommy leaned forward and looked into my son's large brown eyes with his gentle blue eyes. Tommy smiled before his lips met Joey's. They began to kiss, and a moment later I watched their tongues dance in each other's mouths.
While their tongues played, Tommy lowered his body until his cock touched my son's asshole. Shortly after initial contact, Tommy pushed down, forcing his large glans into my son's wrinkled hole. With an uncomfortable groan from Joey and a lustful moan from Tommy, he was inside.
Once inside, he wouldn't get out until he was finished. Tommy began thrusting until his entire shaft was inside Joey's skin and his testicles were pressed against Joey's. Then, with one powerful thrust, he pushed in a little further before pulling out. He withdrew his shaft as far as it would go and then thrust it back in, sending an electric shock through my son's body.
Now that Joey had gotten used to the cock in his ass, Tommy started pulling it out and thrusting it back in while he fucked my son. He lowered his head and began licking and sucking my son's nipples while I pushed his small cock in and out of Joey's body.
I was already aroused from watching Tommy's ass move up and down, but now that Tommy's ass was so clearly visible and I saw his cock sliding in and out of my son, I was getting overheated. I was so close to orgasm that it actually hurt. From experience, I knew Tommy wouldn't be long before he had one of his dry, childlike orgasms. I watched him closely, waiting until he was on the verge of coming. When I saw Tommy thrusting harder than usual, I knew it was happening. I reached between my legs and pressed hard on my clit through my denim shorts. That was all it took. I exploded, flooding my panties and shorts with one of the biggest loads of cum I'd had in a long time. As my breathing returned to normal, so did Tommy's and my son's. Tommy pulled out and kissed my son on the lips before lying down next to him in bed. Joey wrapped his arms around Tommy and held him tight as they cuddled. As always, I tucked them in and let them sleep together while I worked in the house.
This had been the norm for a few months, and until then, it had simply been sexually arousing. Almost a year had passed since I had started babysitting Tommy. He was eight years old at the time, and since both his parents worked, they needed someone to look after him when they both had to work at the same time. Since Tommy and Joey were already friends, it was only natural that I would babysit him.
I was a single mother when my husband died due to medical negligence. I received a generous severance package, so I didn't have to work full-time anymore. I worked here and there for a little extra to buy special things, but mostly I helped out at homeless shelters whenever they needed me.
When the opportunity arose to babysit Tommy, I jumped at it. I thought he was really cute and knew his parents could use some help. They paid me, but not as much as a daycare, and I was available day and night if they needed someone to look after their child. I'd been babysitting him for about six months when the boys got stuck outside in the rain. When they finally got home, they were soaked and covered in mud from trying to run through the puddles to get to the house. I met them at the back door as they came running upstairs. "Stay calm, you two. You're not getting into this clean house looking like that," I ordered. They just looked at me as if they didn't know what to do or say. I told them to just stand still for a moment. They were sheltered from the rain on the porch, but not inside, so I knew they were safe when I went to get some towels. When I came back, I simply said, "Take your clothes off."
"Here?" they both chirped.
“Yes. Right here. Right now. Nobody will see it, and if they do, I’m sure they’ll like it,” I teased her.
They slowly began to undress completely. When they had only removed their underwear, they paused and asked if they should take off their underwear too. I told them that their underwear had to come off as well. Finally, they removed the last piece of clothing. Now I had two little naked boys right in front of me. I felt my pussy getting hot as I looked at their cute little limp cocks. After I had a good look at them both, I took some towels and dried them off, paying special attention to their genitals. I sent them to the bathroom, where I had them both take a warm bath at the same time. Meanwhile, I threw their clothes in the washing machine. When they were finished bathing, I dried them off and sent them to play in Joey's bedroom. I told them to stay naked until their clothes were washed and dried.
I went to check on them a little later and found them both examining each other's genitals. I stood in the doorway and watched as they began touching and stroking each other's penises and testicles. Joey went a step further and had Tommy lie down so he could get a better look at Tommy's anus. He spread it open but never inserted a finger. I noticed that the longer they touched and played with each other, the more intense they became. The harder they got, the more they played, until they both had stiff, small, bald penises.
Since my panties were getting wet quickly, I finally made my presence known. I entered the room and watched them until they realized what I was watching. Tommy noticed first.
“Miss Judy,” tweeted Tommy.
This caught Joey's attention. Joey sat up and pulled his fingers away from Tommy's small penis. Then he placed his hands over his genitals to cover his hard cock.
“Mom… we just…” Joey began.
"It's okay. I know what you did." I interrupted him. To defuse the situation, I asked, "Do you have any questions? Is there anything you'd like me to teach you?"
"What do you want me to teach you?" Joey asked.
“Well, whatever you can do to make it feel good. There are a lot of things you’ll need to know eventually, so you might as well learn them at a young age,” I replied.
“Okay,” they both said, finally relaxing and exposing their genitals.
The sight of these two little boys naked, with their semi-erect little penises, quickly brought back memories of how my fetish for little boys began. I was a young teenager when I accidentally caught my two younger brothers about to fuck each other in the ass.
I must have been about 14 years old at the time. Sam, my 10-year-old brother, was lying on the bed with his brother Ted between his legs. Ted was 11, almost 12, at the time. They were both completely naked and both hard as rocks. Ted's penis seemed about 11 cm long, but rather thin. Sam's small penis was about 9 cm long and almost as thick as his older brother's. Sam had no pubic hair at all, while Ted only had a few scattered hairs that were just starting to sprout. When I came in, they first told me to leave because they were busy, but when I didn't go, they gave up and told me to be quiet if I wanted to stay. I watched as Ted smeared something from a tube onto Sam's buttocks and then some onto his own hard penis. I knew enough about sex to know that to have sex, you had to take a penis and put it into a girl's vagina. I had no idea two men could do it together, so I was really interested in what they did and how they did it. Ted positioned his penis at Sam's asshole and started thrusting. Sam squirmed as he tried to get away, but he never yelled for me to make my brother stop. Ted, who was much bigger, held Sam until he could push the tip of his penis into Sam's ass. Once the tip was in, Sam calmed down and let his older brother push the rest in as well. Then Ted started pulling out and thrusting back in. I knew from sex education class that Ted was fucking Sam. I had never seen two people do it live before, so it was a very formative experience for me, being my first time.
As I watched Ted fuck his brother in the ass, my fingers began to caress my pussy through my tight shorts. The harder Ted fucked his brother, the harder I pushed into my own slit. Just before Ted came, a very strong, pleasurable sensation washed over me. It started between my legs and traveled up through my stomach, my chest, and finally my glans. Later, I realized I had just had an orgasm, one I didn't know I could have on my own since masturbation wasn't covered in class back then. When Ted was finished with Sam, he pulled out. I looked more closely at Ted's penis and saw something white at the tip. I thought that was the semen I was seeing, and Ted must have put some of it in his brother's asshole. They switched positions, and this time Sam put his penis in Ted's ass, but when Sam pulled his limp penis out, there was nothing left at the tip. I was confused, but I knew I couldn't ask anyone, so I just let it go. Later, I learned that Sam was too young to ejaculate. Even though he had an orgasm, nothing came out, which was called a dry orgasm. I stayed and watched until they got dressed. Ted told me that if I promised not to tell anyone, I could watch if they did. I didn't want to tell anyone anyway, but I promised so I could watch them have sex again. I got to watch my two brothers have sex many times over the next few years. As they both grew hairy and got older, I kind of lost interest. I still watched, but it just wasn't the same as when they were both hairless or almost hairless. Now that I have my own son and another little boy, both young and hairless between their legs, right in front of me, I've started to take an interest again. I knew Tommy would be back in a few days, and I also knew his father would be picking him up soon. So I told the boys that since Tommy was leaving soon, I was going to teach them a lesson the next time he was here. They were both disappointed, but they understood. I made sure they weren't to tell anyone about our arrangement or that we'd had anything to do with sex. They said they understood and wouldn't say a word. Their clothes were dry by then, so I let them get dressed before Tommy's father showed up.
A few days later, Tommy was back at our house, and I kept my promise. First, I had them undress, and we went over their anatomy. I explained what each body part did and how they would orgasm, but they wouldn't ejaculate for a while. I taught them how to suck cocks and how to fuck each other in the ass. Oral sex wasn't that important to them, but they both really enjoyed being fucked in the ass and fucking each other in the ass. Eventually, we got into a routine: When Tommy came over, they would play outside or in the house until after lunch. They would eat, and while I cleaned up, they would bathe together. After the bath, I would dry them off, and they would run naked into Joey's room, where they would fuck each other in the ass. Afterward, I would let them cuddle and take a nap. Then I would wake them up so they could get dressed and play until Tommy's father came to pick him up. They both enjoyed the whole thing, and I simply loved watching two little boys with hairless penises getting their asses fucked again.
Today was no exception. While they cuddled, I cleaned the house and prepared dinner. At the agreed time, Tommy's father came and picked him up. I finished eating, and soon Joey and I were sitting at the table eating.
"So, where did you learn the doggy style position?" I asked my son while we were eating.
He giggled sweetly before telling me the story. "You remember Fred, don't you?" he began.
“Yes, he’s the cute little eight-year-old next door. I babysat him a few times a while ago,” I replied.
"Well, he has an older brother named Frank. He's 13, almost 14. Anyway, I was playing with Fred in their house when Frank came in and asked if we wanted to see something exciting. We said yes, so he took us outside and showed us two dogs doing it in their garden. Frank told us they were doing it doggy style. It looked so funny that I watched closely so Tommy and I could try it," he told me.
"So, did you like it?" I asked.
“Um… Hmmm…”, he groaned.
As we continued eating, we talked about school and many other things. I noticed Joey's absent-minded look, and I knew he wanted to ask something. I knew from experience that he would ask as soon as he was ready, so I just waited. It wasn't long before Joey asked me a surprise question.
"Mom?" Joey asked quietly.
I knew it was time, so I replied, "Yes, baby?"
"Um, may I ask you something?" he continued.
"You know you can ask me anything," I said.
Joey took a deep breath and then asked, "How long does it take for Tommy to ejaculate?"
Well, I thought I was prepared for any question he might ask, but this one completely threw me off. I was not only wondering how to answer, but also why he was asking such a thing. Since I didn't know why, I just answered as best I could.
"Well, sweetie, it's going to take quite a while. Usually sometime between 11 and 13, but it could take longer. So at least another two years for him and at least a year or so for you," I explained.
“Oh,” he said, disappointed.
I don't know exactly why I continued telling him what I was thinking, even though he hadn't asked, but for some strange reason I added, "My younger brother Sam was 13 when he first ejaculated." No sooner had I said it than I knew I had made a mistake.
Joey's head shot up from his plate, he looked me straight in the eyes and asked, "How do you know when Uncle Sam first ejaculated?"
I'm sure I blushed, and without being able to think of anything else to say, I decided to tell the truth. I told my son the whole story about how I'd caught my brothers having anal sex and how they'd let me watch so I wouldn't tell on them. I explained how seeing my brothers having anal sex had made me very curious, especially about seeing little boys being anal fucked, particularly when they were young and hairless. Then I explained that I was in the room watching them when Sam pulled his penis out of his brother's ass, and it had semen on the tip, just like his brother had when he pulled it out.
We had finished eating and I was just cleaning up the kitchen when I finished the long story. Joey got up to go into the other room when I noticed his penis bulging out of his shorts. I knew my panties were wet with excitement as I told the story, but I had no idea it had aroused Joey too.
"Looks like you need to take care of your little problem," I suggested, glancing at his genitals.
“I guess… I wish Tommy was here so I could stick him up his ass. It’s more fun that way than doing it alone,” Joey explained.
"So, I'm finished here. Should I watch? Would that be helpful?" I asked, hoping he would watch me.
Joey grinned broadly and replied, "That would be funny."
"Do you want to do something different this time?" I asked again, hoping he would agree.
"Sure," he shouted.
"Okay. Go to your room, take off your clothes and come with me to my bedroom," I told him.
Without further questions or delay, he ran into his bedroom to undress. I went into my bedroom and spread a large bath towel on the bed. As he ran into my bedroom, I let him climb onto my bed and sit on the towel. I sat down directly in front of him on the bed, from where I could see him clearly.
“Mmmm… you look good,” I groaned as my juices began to flow.
"And now?" Joey asked quickly.
I smiled at my son as I gave him instructions for a little game. I told him I would tell him when he could stroke his penis, which hand to use, and how fast to do it. I told him he couldn't come until I said it was okay. He was very excited about the new game and ready to play.
"Slowly stroke... Faster... Faster... Now stop. Now use your left hand... Faster... Faster... Faster... Stop." I began giving him instructions.
Once he had calmed down a bit, I continued: “Get on your knees and start stroking with your right hand… Slower… Slower… Now faster… Faster… Do it as fast as you can… Stop.”
Again I let him calm down before continuing. I did this for almost half an hour, and when I thought he'd had enough of the game, I let him come. He had a really intense orgasm, but he was still dry.
Once that was cleared up, I asked him why he wanted to know when Tommy would start ejaculating. He explained that he wanted to feel his ass being filled with hot cum. He also told me he wanted to know how it felt.
tasted. Then, with some hesitation, he told me he wanted to feel a cock ejaculate into his mouth. I felt my panties get even wetter as he told me what he wanted and why.
"Do you think you can find someone who will squirt in my ass and in my mouth?" Joey asked.
"Let me think, and you try to think of someone too. Now go take a shower and get dressed for bed. When you're ready, come into the living room, and we'll watch a movie together," I said to him.
While he was doing that, I took a long shower and pampered my yearning pussy. I got out of the car and put on panties and a short nightgown. It had to be short enough so Joey could see my cute panties. I didn't know exactly why, but I just wanted to arouse him again. Seeing him masturbate in front of me was something really special that I truly enjoyed, and I wanted to return the favor.
After the movie he went to bed, but shortly after I closed the door, I heard him masturbating. That's when I knew I simply had to find a way to give Joey what he wanted.
Over the next week, I thought about it long and hard, and even talked to Joey about it several times. Then something suddenly occurred to me. What about Frank? One evening at dinner, I brought it up to see what he thought.
He smiled, but he had a few concerns. He's so much older that he was worried his penis might be too big. I told him we could work on that, but any guy who could ejaculate would be big. He also asked how we were going to get Frank to do it. And even more so, how we could get Frank to do it while I watched. That was a problem I didn't even know how to solve.
I told Joey he needed to talk to Fred, since they were friends and he was at Fred's house several times a week. I instructed him to ask Fred questions, like whether he'd seen his brother's penis, how big it was, and whether he knew if his brother had ejaculated or not. Joey told me he could do that because he'd talked to Fred about sex several times. I didn't ask, but I figured they'd talked about sex because he also wanted to fuck Fred in the ass.
A few days later, Joey told me that Fred had said his brother had ejaculated because he'd watched him do it several times. Fred even admitted that he'd sucked his brother off multiple times and eaten his semen. When I heard that, my panties were instantly soaked. Fred told Joey that Frank's penis was about 12 cm long and a bit thicker than Joey's.
Next, we needed to find a way to get Frank to fuck my son's ass without Fred being there, but also while I watched. That would require some more trickery.
After a moment's thought, Joey and I hatched a plan. Joey would get Frank to help me with some heavy lifting. I would wear something very sexy and make sure he got a good look at my panties. Once I saw he was hard, I would make sure he saw Joey naked. We figured it would work best if Joey was also hard and playing with himself when Frank caught him. The tricky part was timing it so I'd catch Frank looking at my son. I would tell him he could fuck him if he wanted, because Joey would like it.
For all of this to work, we had to make sure Joey's asshole was big enough for Frank's hard cock. I got a dildo of the specified size and some lube. Together with Joey, I stretched Joy's ass so it could accommodate this big cock. At first, the dildo wouldn't fit, but with time, we finally managed to get it in. After a week of me fucking my son's ass with the dildo, we thought it was time.
We got everything ready, and as planned, Frank came over alone. I'm not sure who was more nervous, me or Joey. I was wearing a short miniskirt, and every time I bent over, my panties were visible. I gave Frank several squirts of my panties, which resulted in a massive erection. It was quite obvious that Frank was hard and ready to fuck.
When the time was right, I sent him to my son's room to get something, but when he opened the door, he saw Joey standing completely naked next to his bed, pulling on his hard cock. To make sure Frank didn't escape, I made sure I got in the doorway before Frank could leave the room.
"Looks like you two have something in common," I said to Frank as he was getting ready to leave the room.
"Ma'am?" Frank asked.
"To put it bluntly: Judging by the look of your hard cock, I think you want to fuck someone. And when you see Joey naked, I think he'd be a good target. How does that sound?" I asked Frank.
"Sounds damn hot to me." "Will you stay and watch?" he then asked.
"Do you want that?" I asked hopefully.
"It's okay," he replied.
Joey grabbed the lube, and in no time Frank was naked. Joey turned around, looked at Frank's long cock, and gave me a questioning look. Frank's cock did indeed look bigger than I'd expected, and I, too, wondered if I'd stretched Joey's ass wide enough.
"That's alright," I mouthed to my son.
He looked at me and smiled sympathetically before handing Frank the lube. Frank began rubbing it on his stiff cock while Joey got into bed. Joey lay down and spread his legs, preparing to be filled with cum for the first time in his life. Frank took the lube and began pushing some of it into my son's hole. He slid a couple of fingers in as far as they would go to make sure Joey's ass was well lubricated. Then he took a pillow and slipped under Joey's buttocks to lift him higher and allow for better penetration.
I moved my chair closer to the action and sat down so I could get a good look at my son being fucked in the ass by a teenager's cock. I hiked up my skirt a little so Frank could see my panties, while trying not to make it too obvious that I wanted him to watch. Then I watched as Frank positioned his glans right at the entrance to my son's tight young ass.
Frank did his best to get his glans into Joy's hole, but for some reason, my son resisted. I'm not sure if he was afraid of the pain or if he simply changed his mind. After several attempts, Frank leaned forward and kissed my son on the lips before bringing his head to his ear. I couldn't hear what Frank said, but a few seconds later, Frank gently thrust again, and at the same moment, Joey relaxed and pushed Frank's glans into my son's ass for the first time. With a soft whimper from my son and a loud, lustful groan from Frank, Frank began to carefully slide his cock in and out of Joey's ass. A few minutes later, Frank's balls were resting on my son's buttocks.
Now that the painful part was over, the fun could begin. I watched as Frank started pulling his cock out of my son's asshole, only to shove it back in faster than before. It only took about a minute before Frank was ramming my son so hard I could hear his full balls slapping against his buttocks. The sound of balls slapping against ass was arousing, and knowing my son was enjoying it, I relaxed and let my pussy get hot. I watched as Frank's cock slid in and out faster and harder. My fingers slipped under my skirt, as little of it as was left, and began rubbing my panties-covered pussy. Frank turned his head and saw me rubbing. I don't know if he liked that better or just my panties. It probably didn't matter, because he soon got going as he went full throttle. The faster Frank got, the faster I got, until we were both trying to outdo each other. Since I couldn't hold back any longer, I took one hand and pulled my skirt all the way up and out of the way. I slipped my other hand under my panties and into my already wet pussy. I fingered myself as fast as I could while watching my own son being ass-fucked by Frank. Frank, on the other hand, watched me and my panties-covered pussy closely as it was fingered by the mother of the son he was ass-fucking. Joey didn't notice at all what Frank and I were seeing.
Soon Joey tilted his head back and closed his eyes, enjoying the fuck of his life. I knew he was enjoying it because his small, hairless cock was harder than ever, and every now and then he stroked it and played with his balls while his ass was being spanked by a pair of teenage balls and his hole was being fucked by the same boy. I couldn't take it any longer and started panting as I felt a massive orgasm wash over me. My eyes took one last, deep look at my son's ass being fucked before I, too, tilted my head back and closed my eyes. My hips lifted as my hand slid inside me. Then, with a final thrust, I let out a loud gasp as my orgasm shot a huge stream of cum into my panties. I had never come so much in my life. My panties were soaked, as were my fingers and the chair I was sitting on. Frank saw my incredible orgasm and couldn't hold back any longer either, shooting a huge load of sperm deep into my son's asshole. Frank collapsed on my son's chest, his breathing audible throughout the house. We all remained in the post-orgasmic position for a few minutes before moving. Joey, the only one who hadn't yet had an orgasm, asked first, "Frank, can I fuck you in the ass now?" he asked cautiously. Frank, who wanted to be fucked in the ass just as much as Joey, quickly turned around and took Joey. Joey was on top and Frank was on the bottom.
"Go on, boy. Fuck me as much as you want," Frank suggested.
Joey quickly lubricated his cock and Frank's ass, and with a swift movement, he thrust his penis into Frank's hot ass. Without any self-control, Joey went at it and kept going until he had an orgasm that rivaled any of ours. He was still dry, but you wouldn't have guessed that from Joey's moans.
Unlike Tommy and Joey during sex, Frank was soon up, clean, and dressed. I could see that Joey was disappointed not to be able to cuddle with Frank, but as I explained later, not everyone likes to cuddle after sex.
I stood up, smoothed down my skirt, and walked Frank to the door. I told him not to act like a stranger and thanked him for everything he had done. I think he was a little confused because he thought he was supposed to be the one thanking me.
Frank would come back from time to time to fuck Joey's asshole. Joey would continue fucking Tommy and eventually got to suck a load of cum from Frank's balls. A few months later, Tommy met Frank. I really enjoyed it when they had threesomes because I usually came at least twice. The following year, Fred joined the group, and for my birthday, they gave me a super nice present. I got to watch all four of them fuck each other after they'd sucked each other's cocks. I came so many times that day that I thought I'd never have to come again. Of course, I was wrong, and just a few days later, I was ready to masturbate again while watching the kids fuck. I'm going to be really disappointed when the kids grow out of this phase, but until then, I'll indulge my unusual fetish.
