Jimmy’s New Fetish 18 Sex Stories Cool – Y2 Stories

Jimmy found out that his friend Max is Trans and they have fun together. Then Max’s Uncle Chris joins in…

Max was still straddling Jimmy, Jimmy’s cock buried in his ass when Chris made his presence known. Max’s load of cum was splattered across Jimmy’s stomach and chest. The boys watched as Chris sauntered into the room. Jimmy was mesmerized by his huge, erect cock. It must have been 9 to 9.5 inches! And thick. And uncut. He had only seen 2 adult cocks and neither one was as big or scary as this one!

Chris strolled to the bed. He was a decent looking guy, Jimmy thought. Kinda nerdy, his sandy blonde hair thinning on top. He has a thick set body, broad shouldered, but not athletic. Maybe when he was younger, but now he had a bit of a paunch around his middle. But that cock! Holy shit! Jimmy both wanted it and was afraid of it at the same time.

Chris took Max’s face in his hands, kissed her, and said, “There’s my naughty girl! Are you being slutty and letting this cute boy fuck you?”

“Yes, Uncle Chris. I’ve been bad. I sucked Jimmy’s cock and let him fuck me. He sucked my girl cock too. I hope you’re not mad that I let someone else do naughty stuff to me,” Max said in a soft, feminine voice, sounding timid. Jimmy was surprised at this interaction, almost as surprised as he was when Max appeared before him, dressed as a girl. A very pretty girl.

“Oh, look what you did, Max,” Chris said in mock surprise, “your girl cock made a mess all over Jimmy. Here, I’ll clean it up. Without asking, he leaned over and licked Max’s cum off Jimmy’s chest and stomach. He suddenly popped his head up and looked at Jimmy.

“I’m sorry, Jimmy. I should’ve asked first. Do you mind?”

“No. Uh… ummm…”

“You can just call me Uncle Chris like Max does. At least while we’re all in here, naked and playing together. You don’t mind if I play too, do you, Jimmy?”

“No. Not at all,” replied Jimmy as he reached out to touch the man’s cock. He found that the beastly member was so thick that he couldn’t get his hand all the way around it. Chris moaned and smiled at the boy’s touch, putting his own hand over Jimmy’s and moving it on his cock.

“Good boy, Jimmy! Now I have a girl and boy to play with!” He turned his head to Max and said with an enigmatic smile, “Just like I do when I fuck both your parents. Right, Maxy girl?”

“Right, Uncle Chris. They both love your big cock.”

Another surprise for Jimmy. Max’s whole family was addicted to the big cock in Jimmy’s hand. He could see why. He wanted to wrap his lips around it himself, but he was wary of taking it up his ass. But then he thought about Lizzy and Sadie, and how they had both taken his cock in their tiny assholes. He was willing to give it a try.

Max looked at Jimmy and said in his nervous, feminine voice, “Mom and Dad don’t know that Uncle Chris and I play together. They don’t know that I know about them all playing together either. And they definitely don’t know about Girl Max. Or Maxy, as Uncle Chris calls me.”

“They won’t hear it from me, Max. Maxy.”

“Thanks, Jimmy.”

Uncle Chris then said, “Maybe it’s time they did know. Maybe they should know what a naughty, slutty girl they have. Hmmm?”

“Maybe they should, Uncle Chris. Maybe Mommy would let me play with her titties and pussy. I’d like that. I’d like to play with Daddy’s cock too.”

“I’m not surprised you want to play with your daddy’s cock, you little slut, but your mommy’s titties and pussy too? Girls playing with girls is so very naughty. Shame, Maxy!”

Jimmy’s cock had started to go soft after he came in Max’s ass; now all this talk of incest and group sex had him back to full hardness. He started to gyrate his hips and slowly thrust into Max. Max responded by gyrating her own hips. Jimmy started stroking Chris’s dick harder and faster.

“Seems like you two kids are getting turned on again. Jimmy, would you like to suck my cock?”

Jimmy responded wordlessly, just looking into the man’s eyes and nodding. Chris moved onto the bed, closer to Jimmy’s hungry mouth. Jimmy turned partly sideways and took the monster sized meat into his mouth, as much as he could, anyway. He stroked what he couldn’t take down his throat. It was a struggle getting his mouth open far enough to take any of it in.

“Good boy, Jimmy! You’ve done this before, haven’t you? And not just Maxy’s girl cock.”

Jimmy again just nodded, not wanting to take his mouth off that wondrous piece of man meat. Both his dad and Sean were cut so sucking this uncut one was a whole new sensation. He liked it. A lot! Chris was moving his hands around Jimmy’s body, tweaking his nipples with one hand, running the other through the boy’s hair. He cooed to his new lover.

“That’s good, Jimmy. You’re a good boy. A good cocksucker. Do you think you can take this big dick in your ass?”

Jimmy stopped sucking Chris’s cock but kept stroking it as he answered in a hoarse whisper, “Yes. I want to try it. I want to do it!”

Max was still gyrating and grinding on Jimmy’s dick when he said excitedly, “Do it, Jimmy! I love Uncle Chris’s big cock in my ass! He’s been fucking me for 2 years now!”

Jimmy was shocked that this horse cock could fit in an 11 year old ass, girl or boy. Chris instructed the pair to keep fucking as he helped them switch positions, putting Max on her back, Jimmy fucking her missionary style. The man moved around behind Jimmy. Jimmy felt the cheeks of his ass spread and Chris’s tongue start to probe his tight back hole. After a few moments, the tongue was replaced with a lubed finger. Jimmy wasn’t sure where the lube had come from, but he was glad that it was there.

Chris got up behind Jimmy and pressed the head of his huge cock against the boy’s sphincter. He rubbed the boy’s back and spoke soothingly to him. Jimmy paused his fucking of Max’s ass.

“Are you ready, Jimmy? You’ll be fine. The asshole can stretch much more than you think. I’ll start slowly, then you set the pace. Tell me how you want me to fuck you.”

Jimmy felt some trepidation but answered back, looking over his shoulder behind him, “I… I’ve done this before… just not with one so big.”

“Like I said, the asshole stretches more than you think. Now, let’s do this. Bear down like you’re pooping. That’ll make it easier.”

“Okay. Go ahead.”

Jimmy leaned forward more, giving better access to anus to Chris. This pressed him more against Max. Max wrapped her arms around her friend and whispered into his ear, ” You’re going to love this, Jimmy! I do! I love when Uncle Chris fucks my pussy!”

Jimmy felt the head of Chris’s cock pushing past the resistance of his sphincter. The resistance was overcome in few somewhat painful seconds. Jimmy seethed at the flashing moment of pain. The pain quickly dissipated once the head and a few more inches were in.

“You doin’ okay, Jimmy boy? You want me to stop?”

Jimmy said through gritted teeth, ” No! Dammit! No! I want you to fuck me! Fuck my asshole!”

Chris continued to push in slowly until Jimmy yelped. He got all but about an inch of his cock into the boy’s shit hole. He started slowly pumping in and out of it slowly, keeping in mind the boy’s limits. He continued this slow pace until Jimmy told him to go faster. He had told the boy that he would set the pace.

Jimmy was getting used to the invasion of this horse cock in his tight boy hole. He wondered if this was how Lizzy and Sadie had felt when he fucked their asses. They both said that they had enjoyed it. He was enjoying this too. He couldn’t believe that he was able to take the monstrous meat and enjoy it so much.

“Yes! Harder! Do it, Uncle Chris! Fuck my ass!”

Chris started thrusting harder, pulling back almost all the way out, then ramming back in. His thrusting caused Jimmy to again start his own thrusting in Max’s ass. All three members of this union were moaning, groaning, grunting, yelping, and just plain yelling out their pleasure! Jimmy got the point of over-stimulation and soon he was emptying his balls in Max’s ass again. He slumped onto Max’s chest and his friend held him there, kissing his face and neck.

Chris continued jackhammering Jimmy’s asshole as the boy laid on his friend, nearly unconscious. Finally after several minutes of this anal assault, Chris shot a huge load up Jimmy’s shit chute. He held in place for a few minutes as he trembled and quivered through the remnants of his climax. Satisfied, he withdrew his now semi-flaccid cock from Jimmy’s tender ass. He helped pull Jimmy off Max and lay him on his back. He pulled the boy’s legs back to his chest, exposing his still gaping hole. He instructed Max to clean up the deluge of cum emanating from it.

Max went to work with her talented tongue, cleaning up every drop. Uncle Chris told her that she didn’t have to share it with him, she could swallow it. She gladly swallowed it all, like it was a reward. Chris saw that her cock was still hard.

“Didn’t you cum this time, sweet girl?”

Max shook her head, saying, “No, Uncle Chris. I didn’t cum this time.”

Chris had her lie back and took her sweet girl cock in his mouth and sucked her until she came. He swallowed the creamy load. He got off the bed and told Max to get in the shower with him. He took the pigtails out of Max’s hair before they got in, then after they got in, washed off all the makeup, making Girl Max back into Boy Max. The two washed each other off. Afterwards, Chris dressed and went back home. Jimmy slept through all of it.

In the morning, Jimmy woke up before Max. He saw that the makeup was gone and Max was presenting as a boy again. He got up and stared down at his nude friend for a moment, admiring what he saw, wondering at what was going on with him/her. He had definitely enjoyed what they had done together and wanted to do it again, but he wondered if he would have to treat Max as a girl now. He knew things were instantly different when they became lovers, just like everyone else in his life that he was now having sex with, but he had no clue what to to do with a transgender lover. He would just have to talk to Max about it later. He would let his friend decide how they proceeded.

Jimmy headed down the hall to get in the shower. As he started walking, he noticed that his asshole was sore. He wasn’t surprised, given the pounding it had taken from Chris’s horse cock. He got under the hot water and cleaned all the dried semen off of him, including from his tender back hole. When he got out of the shower, he inspected his wrecked rectum in the bathroom mirror. It was red and swollen. He was reminded of those red-assed monkeys at the zoo. He then headed back to Max’s room. He found his friend and lover stirring awake.

“Good morning, Jimmy,” Max said sleepily. “Did you sleep well? I know I did. You wore me out!”

Jimmy laughed and said, “I think Uncle Chris had a lot to do with that! Where is he?”

“He went home last night. He has to work today. Let’s grab some breakfast.”

The pair strolled to the kitchen, still nude, and had some cereal and juice. Max looked nervous again so Jimmy asked what was wrong.

“Well, you found something out about me, and I’m sure you’re wondering where we go from here. I don’t want things between us to be… weird. I’m sure you have a lot of questions. I know I have some for you.”

“First I have to ask… how do I put this… do you want to be a girl? I mean all the time? A transgender person? Do you only want to have sex with boys and men?”

“I like dressing up as a girl and playing that part, yes, but I don’t think I want to do it all the time. I like being a boy in the rest of my life, but playing a girl for Uncle Chris is hot. I love doing it. Before last night with you, he was the only person I’ve ever had sex with. I do want to have sex with girls. I’m not kidding when I talk about how hot your sister is. I’d fuck her in a heartbeat!”

Jimmy chuckled inwardly at that last remark, thinking that he could probably make it happen. He didn’t say it though, just asking, “So how did it start between you and Uncle Chris?”

“Well, I was staying with him while my parents were on a cruise a couple years ago. One night I wet the bed. I don’t know why. I hadn’t wet myself since I was in diapers. I woke up Uncle Chris and told him. He didn’t get mad but he wasn’t happy either. He stripped the bed and cleaned up best he could for the night. Then he put me in the shower. He got in with me, which surprised me. I couldn’t believe how big his dick was, even soft.”

“No kidding!”

They both laughed and Max continued, “He paid a lot of attention to my dick, saying that we had to make sure to get all the pee cleaned off of it. I got hard. I was embarrassed but he told me not to be. He kept cleaning it, just using his bare hands and some soap. After a what seemed like an hour, I had this funny feeling like I was going to pee. I told him that. He said it was fine and kept going. Then it happened. I had my first cum. Nothing came out then but that’s what it was. You know what I’m talking about.”

“Yep.”

“His dick was hard then. He told me to dry off and get in bed. He stayed in the bathroom a while longer. He was jacking off. I didn’t know what that was at the time but he told me about it later on. The next night he had me come in his room before bed. He pulled out something he had bought earlier in the day. It was a package of diapers. He had me put one on. I didn’t want to but I couldn’t tell him no. It was big enough to fit me. As I stood there wearing it, he told me I looked like a little girl with my long hair and diaper.”

“The next night he gave me a bath and washed my dick until I came again. He sent me to bed and stayed in the bathroom again. He came in the bedroom and told me to sit up while he tried something. First he put another diaper on me and then put my hair in pigtails. He said yep, just like a little girl. The next day he went to the store and brought home a bag full of stuff.”

“He didn’t give me a bath that night, but he pulled the stuff out of the bag and told me that I would be wearing it. It was a girl’s nightie and matching panties. He said that I showed that I didn’t need the diaper anymore. I put the stuff on and he did my hair again. I looked in the mirror and actually liked it. He rubbed me all over and rubbed my dick too. He said it was time for his little girl to learn how to make him feel good. We got in bed after he took his shirt and pants off. Then he took his underwear off. There was that monster cock again. He laid back and showed me how to stroke it until he shot his load. I was pretty surprised at that, surprised and fascinated. He had me taste it. I loved it!”

“Then he really shocked me and sucked my little dick. This went on until my parents came home. After that, whenever he watched me would play like that. He bought me dresses and makeup and girls’ underwear. Bra and panty sets. Jewelry. We keep all the stuff at his place so my folks don’t find it. That’s what the bag I brought home was for.”

“So I went from jacking him off to sucking that monster. I lost myself completely in this… role-playing. I loved playing the girl. He showed me all kinds of porn. I saw people getting fucked in the ass and asked him when he was going to do that to me. He bought me anal toys to get me ready. Eventually he did it. I fucking loved it!”

“I told him that I wanted to fuck one of my friends. He asked which and I immediately said you. Honestly though, I’d fuck Georgie or Ollie or Brayden too.”

“I get that. I’ve been wanting to hook up with any of you guys too. Maybe we can get the others to do something with us eventually.”

“That would be awesome! Anyway, he encouraged me to try it with you and asked if he could join. Sorry I didn’t warn you about him first.”

“It’s all good. I obviously enjoyed myself.”

“Yeah, you did.”

“You and Uncle Chris both said something about fucking your parents. What’s up with that?”

“Uncle Chris confessed to me one day that he and my dad had been fucking since they were in college, before my parents even met. They eventually started having threesomes after Mom found out about them. Turns out she’s bi too. Uncle Chris wants us all to start fucking. I want it to happen too. Now it’s your turn to spill it. Who have you been fucking? You said you’ve been with males and females. Like that. Not boys and girls. Have you been fucking adult men and women or what?”

“Dude, I’ve been fucking people in a big age range, from 7 to 40?”

“Huh?”

Then Jimmy laid all his cards on the table. He figured that Max had opened up his biggest secrets to him so fair was fair. He started with seeing Lizzy peeing, her sucking him, his sister taking his virginity, his mother, Sandi, Sadie, April, Sean, his dad. Every card in his hand.

“Damn, dude! That’s a lot of fucking! So 6 pussies and 2 cocks and all the ass that goes with them. And you get to fuck Brit! Damn you!”

“Yep. I could probably get her to fuck you too. She’s pretty freaky. She might like it if you did it as Girl Max too.”

“Don’t get my hopes up, fucker! Don’t play with me!”

“Dude, I am not kidding! She’s a freak! She took her own brother’s virginity!”

“Fuck! I would die happy! Hell, I’d die happy just seeing her naked!”

Jimmy laughed at that. Max then said, “So, let me get this straight. You have an 8 year old girlfriend, you fuck her and almost everyone in her family, you fuck everyone in your family, you fuck your sister’s big titted best friend, and they all pee on you!”

“Well, I’ve only fucked April once so far, and she hasn’t peed on me… yet. And I can add my crossdressing friend and his uncle to my list.”

“Man, you’ve had one hell of a summer!”

“Don’t I know it!”

“I have to pee. You wanna…”

“Maybe next time. I need to get going. Work to do.”

Next chapter, Jimmy can add another pussy to his list…