Dresses and stuffies (Tommy and Wilbur)

7.1K 155 65
                                    

Request by tilleybelle1020

Little: Tommy (3-4) CG:Wilbur

Warnings! Panicking

Plot: Tommy just got a new dress, he regresses and wants to tell Wilbur about his dress. But, when he joins the call, he doesn't know that Wilbur is streaming.

This is the type of dress that Tommy is wearing in this story

Oops! This image does not follow our content guidelines. To continue publishing, please remove it or upload a different image.

This is the type of dress that Tommy is wearing in this story.

-No ones POV-
"So in today's stream, we're gonna start a new building on the SMP" Wilbur said to his chat as he started the stream. He streamed for a bit just like normal, until Tommy called him. "Guys, Tommy's calling me" Wilbur said and he picked up the call. "Tommyyy! What's up big man!" Wilbur greeted his friend.

   "Wilby! I got a new dwess!" Tommy shrieked excitedly. He didn't know that Wilbur what streaming and was so excited to tell Wilbur about his new dress. Tommy loved wearing dresses, especially when he was little. "That's awesome Tommy, but..." Wilbur said, trying to let Tommy know that he was streaming.

But Tommy interrupted him almost immediately. "It's dis- dis- gween dwess with dawk gween pocodots and- and it has lace!" Tommy was so exited that he stuttered over his words. Wilbur's face melted into a soft smile, hearing his little so exited made him so happy. But he still needed to tell Tommy that he was streaming.

"Tommy, that sounds like such a pretty dress but I have to tell you something..." Wilbur tried again but Tommy started talking again. "And I got this new stuffie, it's a puppy! His name is Poppy and it's so cute!" Tommy told his caregiver. "Le's fasetime! Pwease Wilby, can we FaceTime? I want to show Poppy to you and my dwess!" Tommy said excitedly and Wilbur heard Tommy clap his hands.

Chat was blowing up, asking questions about Tommy's behavior and why was he wearing a dress. Wilbur was quiet, he didn't know what to say to Tommy. He didn't want to ruin the little boy's joy. "Wilby? FaceTime?" Tommy asked again, sounding worried that he said something bad. "Tommy, please listen. I'm streaming" Wilbur said quietly and Tommy immediately went completely silent.

"Stweaming? Wh-why didn't Da say anything?" Tommy asked quietly, sounding sad and scared. "I tried big guy, but you were so exited and didn't let me finish" Wilbur said, trying to smile. Then it was quiet again for a bit. "Tommy?" Wilbur asked when the boy didn't say anything. Then Tommy left the call and Wilbur stayed quiet.

"Guys, Tommy will probably tell you about this on his own at some point. I'm sorry I will have to end this stream so short, but I promise the next one will be extra long for you guys! See ya!" Wilbur said before ending his stream. Wilbur knew he had to go and visit Tommy. He started collecting his stuff together, keys and stuff.

Wilbur pulled on his shoes and grabbed his jacket, he tried calling Tommy, but got no answered. Then he walked over to his car and started it. Wilbur felt so bad for Tommy, he just tried to tell his caregiver about the new stuff he had gotten and there were over 10k people watching and listening.

Wilbur let out a sigh, he decided to get something fun for Tommy to make him feel better. He pulled over at a store and got in. He walked over to the baby section and grabbed a pack of new pacifiers for Tommy. He knew that they should be adult sized that you get from the internet, but this was the best he could do.

Then he also grabbed a new blankie for him, Wilbur knew how much Tommy loved blankies. He payed the items and got back to his car. Then Wilbur started his ride towards Tommy's house. It didn't take that long, when he arrived, he knocked on the door. Tommy's dad came to open the door.

"Wilbur, hi! Did you plan a meeting with Tommy?" He asked while standing on the doorway. "Actually... I did not but Tommy really needs me now" Wilbur sighed. "Needs you? What do you mean, is something going on with Tommy?" His dad asked, sounding worried. "No no, nothing to worry about, just some stuff to do with streams and stuff" I brushed it off.

Wilbur knew that Tommy's parents didn't know about his regression and he didn't want them to know. "Oh of course, come in" he smiled and invited Wilbur in. We chatted for a bit as I took my shoes off and Tommy's dad showed me where Tommy's room was. "Call me if you guys need anything" the older man smiled as he left to the kitchen.

Wilbur knocked on the door, waiting for an answer before going in. "Tommy, it's me" he called out quietly. "Wilby?" He heard a quiet voice. Wilbur opened the door and saw Tommy bundled under all of his blankets on his bed. "Oh little one, are you ok?" Wilbur asked quietly as he sat on the edge of the bed.

"No, evewyone saw" he whispered quietly and peeked from under the blankets. Wilbur patted the blanket bundle. "It's ok Toms, no one will judge you. Come out now and show me your new dress" Wilbur encouraged the little. Tommy thought about it for a bit until he crawled out from under the blankets.

He sat on the bed, still in his new dress. "It's very pretty Tommy" Wilbur smiled and Tommy grabbed his new stuffie from the end of the bed. "Thankies" Tommy murmured and smiled a little. "And, I got a gift for you!" Wilbur said and gave the bag for Tommy. Tommy's eyes lid up as he started digging though the bag.

He got out the new pacifiers and blankie. "Open pwease!" Tommy said excitedly and gave the pacifier packet to his caregiver. Wilbur opened the package and Tommy immediately grabbed one, putting it in his mouth. He giggled and it made Wilbur smile. "Thank you so much!" Tommy laughed and hugged Wilbur.

"Of course little one, anything for you" Wilbur smiled. Tommy wrapped his new dog stuffie into the new blankie. Then he crawled onto Wilbur's lap, ready for a nap. "Should you change out of your dress before napping?" Wilbur asked quietly. He waited for an answer, but then he noticed that the little had already fallen asleep.

That made Wilbur giggle. "Well, maybe later.

Hope you like this one!

Dream SMP age regression one shotsWhere stories live. Discover now