Timmy’s Wild Fantasies

Timmy’s Wild Fantasies Timmy’s Wild Fantasies

Status: In Progress

Genre: Humor


Status: In Progress

Genre: Humor


A boy named Timmy has these wild fantasies of wanting to write stories of people in embarrassing and humiliating situations. But soon, eventually he’ll be in those situations as well, just as the ones he writes in his stories. But will he submit to his feelings and like it?


A boy named Timmy has these wild fantasies of wanting to write stories of people in embarrassing and humiliating situations. But soon, eventually he’ll be in those situations as well, just as the ones he writes in his stories. But will he submit to his feelings and like it?

Chapter5 (v.1) - Fun at the park

Chapter Content - ver.1

Submitted: January 09, 2021

Reads: 85

A A A | A A A

Chapter Content - ver.1

Submitted: January 09, 2021



I start to wake up. It was Sunday morning. I got out of bed, a little groggy and tired. 

Timmy: *yawn* What a day yesterday...I have a feeling that Carly will call me today for more fun. 

I said as I scratched my little butt, but I wasn't aware that I was still naked from last night. I then walked to the bathroom close by to my room, and went inside to brush my teeth. As I was brushing my teeth, my Mom came in the bathroom. 

Mom: Huh? Uh heehee. Hi there, Timmy. 

Timmy: Good morning, Mom. 

Mom: So uh, you just woke up? 

Timmy: Yeah. Just doing my usual morning routine. Why? 

Mom: Heehee. Well I didn't know you had a streaking morning routine. 

Timmy: Huh? What do you mea-? EEP! 


I looked down and immediately blushed and covered my little wee wee with my hands. Wait.....Why did I call it a "wee wee"? Well, I decided not to focus on that. I was naked in front of my mom. 

Timmy: *blushed* Uh mom, I can explain! It was uh hot last night, and I was trying to be comfortable so I can sleep. 

Mom: It's ok. I understand. 

I was surprised to hear that. My mom didn't seemed to mind it at all. 

Timmy: Wait.....Really? 

Mom: Yeah. Me and your father don't mind seeing you naked. Back when you were 5, you used to run around the house butt naked all the time. And even at our family parties and vacations too. 

Timmy: Wait! Really? You never told me that. 

My mom just giggled at my reaction. 

Mom: Well I thought you'd already knew. But then again, you were just a little kid, so you probably wouldn't have remembered it. 

I was just lost for words. Did I really acted like a little naked jaybird back when I was 5. I then start to get images of those silly childhood memories. That must be why I had that enjoyable feeling when I was at the school last night with Carly, taking my first baby steps of being an exhibitionist. A little smile begins to form on my face. 

Mom: Ooh~! You're smiling! You do remember! 

I then noticed that my mom was looking at me smiling, so I used one hand to cover my smile, while keeping my other hand on my crotch. My mom just giggles at me more. 

Mom: It's ok, Timmy. No need to be shy about it. You're always gonna be my sweet little boy~. 

Timmy: Uh thanks, Mommy. I-I mean Mom. I'm uh, gonna get dressed. 

Mom: Ok. Honestly, I don't mind seeing you and your cute little bum bum like this. If you ever want to go back to your nakie jaybird ways, I'm absolutely fine with it. 

My mom said as she playfully patted my nude little tushie as I walked out of the bathroom, which made me blush, but smile a little. Was I really starting to like this again? 

It was now 2:30 pm. I was in my room, wearing a red t-shirt and blue shorts and sneakers with short socks. I was writing another story idea in my diary. 

Timmy's naked morning routine at home 


Another story about me. I still don't know why I wrote that, but this time, I was starting to be fine with it more and more. After I finished writing that story, I got a phone call. It was Carly. 

Carly: Hi, little cutie Timmy! 

Timmy: Hi, Carly. 

Carly: You ready for more fun today~? 

Timmy: Uhh yeah. 

Carly: Hmmm, you seem more relaxed when you said that. Getting used to the feeling already? 

Timmy: *Blushed* Well I-I...Uhh I mean..... 


Carly: Heehee. Doesn't matter. Sooner or later, you'll be loving the feeling just like me. Now, come to the park. 

I said ok to Carly and hanged up. I then went downstairs and headed out. But before I did, my Mom sees me. 

Mom: Uh Timmy? Where are you going? 

Timmy: Uhh, just going to the park, Mom. 

Mom: By yourself? 

Timmy: Well uhh..... 


I tried thinking of a good excuse, but I couldn't think of anything. And the longer I stay quiet, the more my Mom will get suspicious. So I just decided to tell her the truth. Well, sort of. 

Timmy: I'm uhh, meeting up with a friend. 

Mom: Ooh! You've made a friend? That's great, Timmy! 

Timmy: Yeah, uhh she's really nice. 

Mom: Ooh~! "She"? Does my sweet little boy got himself a girlfriend~? 

Timmy: *blushed* Mom! 

Mom: Heehee! It's ok, Timmy. You can go see your girlfriend. You two have fun. I hope I get to meet her soon. 

Timmy: *blushed* Thanks, Mom. And uhh, her name is Carly. 

Mom: Carly, huh? Ok. Have fun. 

I then head out and went to the park. 10 minutes later, I was at the park. There was no one here. I looked around for Carly. 

Timmy: Carly? Uhhh, you here? 

I then felt someone cover my eyes with two hands. 

Carly: Heehee! Guess who~? 

Timmy: Uh hehe. Is it Carly? 

Carly: Yay! Congratulations. You win. 

Carly said as she uncovered my eyes and kissed my cheek. 

Carly: Ready for your next step to be an exhibitionist~? 

Carly said as she playfully patted my butt, which made me blushed. 

Timmy: Uhh yeah. What is it? 

Carly: Having fun naked at the park till the sun sets~. 

Hearing this made me blush like a tomato, because unlike the school, we were outside. 

Timmy: *blushed* W-What?! But we're outside! What if someone sees me?! 

Carly: Don't worry. It's just us two here. If we were here earlier, then there would be kids here. Besides, we'll get to that step soon. 

Timmy: Uhh...I don't know if I can do this. It was fine at the school during night time, but- 


Carly teasingly shush me with her finger. 

Carly: Shhh.....Don't worry, my little boy~. You're not going to be alone in this~. 

Timmy: W...What? Y-You mean.....? 

Carly: Yup! 

Before I could say more, Carly strips off her clothes and undies, and stood naked before me. Her body looked so cute, and her boobs were A cups. I'm guessing she's a late bloomer. 

Carly: Heehee~! Just like last night, only this time, you get to see all of me~! 

Carly said as she turned around and playfully wiggles her bare little bum bum at me. I can see those cute little nerdy dimples on her butt. 

Timmy: So cute~.....

Carly: Ooh~! You think I'm cute naked~? 

I immediately blushed at what I said. I don't know why I said that. My mouth just moved on its own. 

Timmy: I uhhh..... 


Carly: Come on~...Take off your clothes and get naked with me...boyfriend~. 

Did she just called me her boyfriend? 

Timmy: B-B-Boyfriend~?! 

Carly giggles at my response. I think for a few seconds, then decided to do it. 

Timmy: Ok. 

I then proceeded to take off my red shirt, shoes, socks, blue shorts and tighty whities. I was now completely naked like Carly. 

Carly: Heehee! Good boy~. I bet you feel much better. 

I had to admit, it did feel pretty good. Maybe this wasn't so bad after all. 

Timmy: Well uhh. Yeah. It actually kinda does. 

Carly: Good. Now let's go play in the park! 

Carly said as she runs off to the park. I followed her. We had lots of fun. Playing on the swings, climbing on the monkey bars, sliding down the slide, which felt cold on my bare butt in kind of a good way, and then playing hide and seek. When she seeks, she playfully pokes my butt when she finds me. As we were playing, I didn't covered my little pee pee at all. Probably because I was having too much fun to pay attention to it. Carly must've noticed it a few times. Later, it was night time. We both got our clothes back on. 

Carly: Heehee! That was fun! 

Timmy: Hehe! Yeah! I had to admit, it was not bad. 

Carly: Heehee! Really~? Do you think you might be ready to take the next step to your exhibitionist~? 

Timmy: Hehe. Maybe~? 

Carly giggles hearing some teasing in my voice there. It felt so good. Maybe I will be an exhibitionist. I'm still a little bit nervous about it, but...maybe I'll be fine. 

Carly: Heehee. Well I'll see you tomorrow at school. 

Before Carly left, I stopped her. I felt like I had to do one more thing today. 

Timmy: Carly, wait! 

Carly: Hm? What? 

Timmy: Uhh Heehee, before you go~..... 


I then turned around, bent down and playfully pulled down my shorts and undies to my ankles, revealing my bare little bum to Carly once again. This made Carly laugh. 

Carly: Heehee! Oh my! 

Timmy: You wanna give my little bum bum a touch too~? Go on. You know you want to~. 

I was basically copying what she did last night at the school. Carly then smiled. 

Carly: Heehee! Oh I'll do better than that~! 

Carly then bent down and playfully gave my bare little tushie a nice little kiss. 



This made me blush and giggle, because the kiss tickled my butt. 

Carly: Heehee. Ooh~. Your little bum bum is smooth like mine. 

Carly said as she playfully rubs my butt. She has nice soft hands. I was about to pull my shorts and undies back up, but Carly stops me. 

Carly: Here. Allow me~. 

Carly said as she pulls my shorts and undies back up. She playfully positioned it so that my buttcrack was always peeking out. 

Carly: Heehee. Perfect! 

Timmy: Hehe. Thanks. See ya later! 

I said as I walked back home. Later on, I was back at my house. I went inside and see my mom. 

Timmy: Hi, Mommy. 

Mom: Hi, Timmy. How was your day with Carly? 

Timmy: Oh it was a lot of fun actually. Maybe we can invite her here sometime. 

Mom: Sounds like a good idea. I would love to meet her. How about tomorrow after school? 

Timmy: Sounds great! Ok, I'm going to bed. Good night! 

As I walked upstairs, my mom could see my little buttcrack peeking out of my pants. 

Mom: Heehee. Good night, my sweet little boy~! 

Later on, I was in my room in just my tighty whities. I've just finished writing in my diary about what happened today. I also wrote another fun story. 

Timmy and Carly's nakie fun at the park 


I liked this story. This broke my uncomfortable feeling about writing stories about me. It felt good. I wanted more. I smiled as I went to sleep. Tomorrow I'll be back at school. 

To be continued..... 

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