AFF Fiction Portal

Winnie, Boy Princess

By: herbcat1
folder Original - Misc › General
Rating: Adult ++
Chapters: 15
Views: 18,974
Reviews: 1
Recommended: 0
Currently Reading: 1
Disclaimer: This is a work of fiction about oral & anal sex between men and an 8-year old boy. The characters, locations & incidents are fictional. Any resemblance to actual events or locales, or persons, living or dead, is entirely coincident
arrow_back Previous Next arrow_forward

Chapter 11

 

©2011 Herb Cat. Do not reproduce or distribute this story without the author's permission.

As an author, I welcome feedback from readers. Please send any comments about this story, positive or negative, to Herb_Cat@mailcity.com. Thank you.

.oOo.

Chapter 11

UPDATE

An awful lot has happened in Winnie's life since I posted her story online. She will soon turn 13. I am purposely using the female pronoun and her girl name; you will soon learn why.

Winnie turned twelve in June. At 4'10, she weighed only 74 pounds soaking wet. Her prepubescent dick was still only an inch when hard, didn't cum and had no pubic hair.

On the last Friday of August, when Jerry picked his nephew up for the weekend, as usual he had an outfit in the car for Winnie to change into as they drove. This time it was a light denim jumper. Underneath, she didn't wear a blouse because the weather was still hot, but only her bra and panties. On her feet she had white ankle sox and pink sneakers.

When they got to the co-op, a boy was shooting hoops in the driveway. He followed them into the garage. When they got out of the car, he said, "Hi, Jerry."

"Hi, Otis. This is my niece, Winnie." The two youngsters shook hands. "Otis lives in that big house on the corner. He moved here from Michigan about a month ago, so he hasn't made many friends yet." The blue-eyed lad was a good foot taller than Wayne and probably twice as heavy, all the extra weight in his muscles.

"I'll be your friend, Otis," said the amiable Winnie.

"Cool! Say, Winnie, would you like to go to the mall tomorrow and hang out?"

Winnie looked at Uncle Jerry. He saw nothing wrong with two kids going to the mall. He thought it would give Winnie a welcome break from all the adults who occupied her every weekend, so he nodded.

"All right, I'd like that."

"Super! I'll pick you up after lunch. My mom'll drive." Otis took his ball and went back to shooting hoops, a big smile on his face.

That evening, Rusty came over to spend the night. As they were eating supper, he said, "You're awfully quiet, Winnie."

"I'm thinking bout tomorrow." Winnie told Rusty about the upcoming date with Otis.

"Wow. That's wonderful, Winnie. I bet you're excited."

"More like nervous, Rusty."

"Why is that?"

"Otis thinks I'm a girl."

"You've been out in public lots of times as a girl, Wayne."

"Yeah, but this is different. I always had Uncle and you guys with me. What if Otis finds out the truth? He'll think I'm a weirdo. He'll hate me."

"There's no reason he needs to find out, Winnie." Later, in bed, Rusty and Jerry did all they could to comfort the lad and assure him he was a very convincing female. To prove it, they took turns plugging his boi cunt.

On Saturday morning, Rusty took Winnie to the gym to practice with the other girls on the Rhythmic Gymnastics team. As usual, he treated everyone to pizza for lunch, then drove Winnie back to the co-op. "You see, Winnie, everyone on the team thinks you're a girl, just like them. If you can fool girls your own age, you can certainly fool a boy whose got stars in his eyes." Winnie thanked Rusty. She felt better.

She took off his singlet from Gym and chose a pair of lavender capri pants for her date. She decided on a fluffy blouse with an offcenter neckline which fairly hid her flat chest. She wondered if Otis was a boobs man. After trying different headbands, she settled on a lavender ribbon that complemented her outfit.

Jerry also put some clothes on and waited. The bell rang and Wayne opened the door. Otis stood there with his mother. He was wearing blue jeans and a black t with the sleeves torn off to show off his biceps. The two kids grinned at each other speechless. Jerry offered to pick the kids up and bring them back home. "Winnie, you have your cell phone in your purse? Just give me a call when you're ready to come home." He kissed his "niece" on the top of her head and smiled as she left on her date, the first-ever as either gender!

Otis's mother let them out by the main entrance and as soon as they got inside, Otis took Winnie's hand. She thought this was really nice. She thought he was really nice. They walked around, looked at clothes, looked at posters, looked at toys. They visited the arcade and played a few video games. But mostly they talked. Winnie learned Otis didn't smoke or do drugs. He seemed to be uncorrupted. He even said he went to church with his family. Otis was going into eighth grade; on April 1st, he would turn 14. Wayne was about to go into seventh, but of course they weren't in the same school district. They found they both liked some of the same subjects, social studies and science. But athletic Otis loved phys ed. He enjoyed both basketball and soccer and was planning to try out for the teams. When he learned Winnie was on a gymnastics team, he promised to attend her next meet. Winnie promised to watch him play soccer. He bought her a Lionel Messi poster for her bedroom. They ended up in the food court and shared another pizza. They talked about popular music; they both like Justin Bieber. They laughed heartily at each other's jokes. Not once did they talk about sex!

Otis admitted he had seen Winnie the first weekend he moved in. Then he noticed she came every weekend. He made a point of befriending her Uncle Jerry, and it was no accident he "happened" to be playing outside when they arrived on Friday. Now Winnie really felt special. They traded cell phone numbers so they could text each other as well as e-mail. However Winnie didn't give him her home address and lied that her last name was Wayne. Otis asked if she was related to John Wayne and they laughed again. 

Winnie called her uncle to come and pick them up. The two lovebirds sat in the back seat holding hands, whispering and giggling. Before they got out of the car, Otis pecked her on the cheek.

"Otis," invited Jerry, "why don't you join us for supper?"

"Thanks a lot, Jerry. Maybe some other time. I think I better get home to Mom. See you, Winnie."

"You know what, Uncle Jerry?"

"What, Sweetheart?"

"I think I pulled it off." Jerry smiled and they went up to 3F.

That night, Harrison came by and heard all about Otis. He slept over and was delighted to find Wayne seemed to feel even more girly than usual. He really didn't mind that the kid was in another world all the while she was sucking him and getting her ass fucked.

On Sunday morning, between breakfast and fucking and shitting and fucking and bathing and fucking, Wayne traded text messages with Winnie's new boy friend: 

"u textn me in church?"

"ys"

"lol"

After lunch, Winnie got dressed for the ride back, packed her backpack with her boy clothes to change into when they got near home, and followed Uncle Jerry down to the garage. Sure enough, there was Otis shooting hoops again. He was wearing cutoffs and a wifebeater and was thoroughly drenched in sweat. Winnie smiled at the sexy lad and he grinned and blew her a kiss. That night, Wayne would look up at the wall at his new poster and think about the dreamboat who made him feel like such a special little girl. He already knew how a girl feels when silky clothes rub on her skin. He already knew the pleasure a girl gets when someone admires her beauty. He already knew the intense orgasm a girl feels when her cunt is getting plowed. But now for the first time, he knew how a girl's heart throbs when she is in love.

.oOo.

As an author, I welcome feedback on my writing. If you have any comments about this story, positive or negative, or would like a list of all my stories, please write to Herbcat@mailcity.com. Thank you.

arrow_back Previous Next arrow_forward