Winnie, Boy Princess
folder
Original - Misc › General
Rating:
Adult ++
Chapters:
15
Views:
18,970
Reviews:
1
Recommended:
0
Currently Reading:
1
Category:
Original - Misc › General
Rating:
Adult ++
Chapters:
15
Views:
18,970
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
Chapter 9
©2010 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 9
"Hey, Jerry, it's Leon. Can I come up?"
As usual, once inside the foyer, Leon got out of his clothes, then followed Jerry to join the others. "Wayne, is that fuckin you?"
"Hehe. Hi, Mister Leon. Mister Keith give me a dress. You like it?" He jumped up and turned, not too fast this time, for Leon's inspection.
"I think my fuckin eyes are playing tricks on me." Leon rubbed them with his fists. "I would never have believed it, Wayne. Wayne? Wayne? I can't call you 'Wayne' when you look like that. Let's see. I know, 'Winnie!' I'll call you Winnie. Come here and sit on Leon's lap, Winnie." The boy giggled and got on the black man's lap. Leon felt underneath the skirt and discovered Keith's jizz dripping out. "Well, now, Winnie, Girl, I see you aren't a virgin any more, are you?"
"Hehe, no. Uncle fucked me last night, and again this morning and then Mister Keith he fucked me. Are you going to fuck me too, Mister Leon? I think my hole is still open, hehe."
"I can't wait, Winnie."
"Can I ask you a favor, Mister Leon?"
"Anything you say, my little princess."
"Please let me leave my dress on when you fuck me. You won't ruin it. It's already wrinkled and dirty."
For Leon, the dress brought back wonderful memories of his niece. He used to have such fun with her. He now felt Winnie was his new little niece and the tears in his eyes were tears of happiness.
Keith and Jerry watched the boy lead their buddy down to the bedroom. Leon's bouncy black ass glowing like bronze and the outlines of Wayne's bubble butt clearly visible through the seat of his fitted skirt. When the two fuckmates disappeared, Jerry turned to Keith. "I still can't believe how Wayne looks in that dress. He's fuckin gorgeous!"
"You mean 'Winnie' and 'She' is fuckin gorgeous."
"Yeah, you were right all along, she's a lovely little girl."
.oOo.
Before he went back home, Wayne asked Jerry to please wash his dress so he could show it to the other men when they came. The following Friday, Wayne/Winnie modeled it for Harrison and was rewarded with a long fuck. On Saturday, Rusty took him to the gym for a couple hours and when they came back, Wayne transformed into Winnie. By then the dress again needed washing. But when Keith came by, he had a second dress with him, a pretty cotton gingham creation. Leon brought a package of three pink girly nylon panties. "We must be ladylike, Winnie. You can't go commando when you wear a dress.
In a few weeks, Winnie had a small wardrobe of outfits, both play clothes and party clothes, as well as a short nightie. In a drawer, she kept several pairs of panties and a couple training bras. For her feet, she had pink trimmed socks, saddle shoes, patent leathers and feminine sneakers. Rusty took her back to the gym and got her a girl's singlet. Wayne's tiny dick didn't make a bulge, so Rusty had him join a class of seven-year old girls. It was fun for Wayne to join them as they waited their turns and giggle at their silly jokes.
The men took Winnie out to the park to play, and to the stores to shop, and no one suspected that this was any other than a little girl. Wayne loved the charade. "Now remember, Winnie," Uncle would whisper to her when they went to a restaurant, "you have to use the little girls' room and when you do, you have to sit down when you pee." To reinforce the habit, Winnie practiced sitting to pee at Uncle's house.
Joel and Ginnie noticed how happy their son was. When he told them he was going to be in a gymnastics meet, he didn't explain which team he'd be on. They promised to come watch, but he knew they wouldn't. Joel and Ginnie were never interested in his activities. At the meet, Winnie didn't do too well. The other little girls, who practiced every day at home, had an advantage over one who was only a girl two days a week.
School was drawing to a close and Wayne's ninth birthday arrived. It was on a Friday, so Jerry came by early and had a party with Joel, Ginnie, Wayne and some of the boys in his school. He gave Wayne a cell phone, preprogrammed with his uncle's number. After the food and cake and games and presents, they headed for Port Washington for a second party. In the car, Jerry gave Wayne a new blouse and skirt, which he changed into as they rode. Thoughtfully, Jerry had also brought along a bra, panties, footwear, and two kitty cat barrettes. Wayne didn't know Jerry had given Leon his spare key, so Winnie was very surprised to find the other men were all waiting for him in the co-op. They ate more food, gave the girl more presents and played games that his young friends never even dreamed of. Rusty and Harrison fucked her on the couch, pushing her panty crotch to one side to gain access. Then she changed into the new nightie that Harrison gave her. Like all her nighties, it barely covered her hips. He fucked her and at last Uncle gave her her final birthday fuck. Harrison, Jerry and Winnie slept in the bed, Leon on the couch, and Rusty on the recliner. Saturday morning, the fucks resumed.
"What are we going to do today, Uncle? Go to the store? the park? I gotta know so I know what clothes to wear." This was the lad who used to wear a T shirt and jeans regardless of the occasion.
"Well, as you know, Winnie. We can do whatever the hell we want. But the weatherman said it's going to be a scorcher today, so..." He reached behind the couch and pulled out a bag with a gift Wayne had not seen. "...so, I bought you this and we can try it out today if you want?" The other men all winked at each other.
Winnie tore open the wrapping and pulled out a bathing suit. A one-piece girls' bathing suit with a mermaid appliquéd on the front. "You mean we can go to the beach?" Jerry nodded. "Yippee!" Winnie pulled off her nightie and took up the bathing suit. "Hey, you perverts! Stop looking at me. Hehehe." They covered their eyes but peeked through their fingers, as Winnie pulled her new bathing suit on. Even in lycra, her tiny cock was invisible. "But what the fuck will you guys wear?" Of course all the men knew what was coming and had brought along their trunks (Leon wore a speedo) and plenty of lotion. They had a great day at Jones Beach playing in the sand and splashing in the surf. That night, back in the co-op they discovered they all had tan lines, even Leon. Only one problem: Wayne's tan line was not that of a little boy. He decided he better not let his parents see him without a shirt on.
.oOo.
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.
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 9
"Hey, Jerry, it's Leon. Can I come up?"
As usual, once inside the foyer, Leon got out of his clothes, then followed Jerry to join the others. "Wayne, is that fuckin you?"
"Hehe. Hi, Mister Leon. Mister Keith give me a dress. You like it?" He jumped up and turned, not too fast this time, for Leon's inspection.
"I think my fuckin eyes are playing tricks on me." Leon rubbed them with his fists. "I would never have believed it, Wayne. Wayne? Wayne? I can't call you 'Wayne' when you look like that. Let's see. I know, 'Winnie!' I'll call you Winnie. Come here and sit on Leon's lap, Winnie." The boy giggled and got on the black man's lap. Leon felt underneath the skirt and discovered Keith's jizz dripping out. "Well, now, Winnie, Girl, I see you aren't a virgin any more, are you?"
"Hehe, no. Uncle fucked me last night, and again this morning and then Mister Keith he fucked me. Are you going to fuck me too, Mister Leon? I think my hole is still open, hehe."
"I can't wait, Winnie."
"Can I ask you a favor, Mister Leon?"
"Anything you say, my little princess."
"Please let me leave my dress on when you fuck me. You won't ruin it. It's already wrinkled and dirty."
For Leon, the dress brought back wonderful memories of his niece. He used to have such fun with her. He now felt Winnie was his new little niece and the tears in his eyes were tears of happiness.
Keith and Jerry watched the boy lead their buddy down to the bedroom. Leon's bouncy black ass glowing like bronze and the outlines of Wayne's bubble butt clearly visible through the seat of his fitted skirt. When the two fuckmates disappeared, Jerry turned to Keith. "I still can't believe how Wayne looks in that dress. He's fuckin gorgeous!"
"You mean 'Winnie' and 'She' is fuckin gorgeous."
"Yeah, you were right all along, she's a lovely little girl."
.oOo.
Before he went back home, Wayne asked Jerry to please wash his dress so he could show it to the other men when they came. The following Friday, Wayne/Winnie modeled it for Harrison and was rewarded with a long fuck. On Saturday, Rusty took him to the gym for a couple hours and when they came back, Wayne transformed into Winnie. By then the dress again needed washing. But when Keith came by, he had a second dress with him, a pretty cotton gingham creation. Leon brought a package of three pink girly nylon panties. "We must be ladylike, Winnie. You can't go commando when you wear a dress.
In a few weeks, Winnie had a small wardrobe of outfits, both play clothes and party clothes, as well as a short nightie. In a drawer, she kept several pairs of panties and a couple training bras. For her feet, she had pink trimmed socks, saddle shoes, patent leathers and feminine sneakers. Rusty took her back to the gym and got her a girl's singlet. Wayne's tiny dick didn't make a bulge, so Rusty had him join a class of seven-year old girls. It was fun for Wayne to join them as they waited their turns and giggle at their silly jokes.
The men took Winnie out to the park to play, and to the stores to shop, and no one suspected that this was any other than a little girl. Wayne loved the charade. "Now remember, Winnie," Uncle would whisper to her when they went to a restaurant, "you have to use the little girls' room and when you do, you have to sit down when you pee." To reinforce the habit, Winnie practiced sitting to pee at Uncle's house.
Joel and Ginnie noticed how happy their son was. When he told them he was going to be in a gymnastics meet, he didn't explain which team he'd be on. They promised to come watch, but he knew they wouldn't. Joel and Ginnie were never interested in his activities. At the meet, Winnie didn't do too well. The other little girls, who practiced every day at home, had an advantage over one who was only a girl two days a week.
School was drawing to a close and Wayne's ninth birthday arrived. It was on a Friday, so Jerry came by early and had a party with Joel, Ginnie, Wayne and some of the boys in his school. He gave Wayne a cell phone, preprogrammed with his uncle's number. After the food and cake and games and presents, they headed for Port Washington for a second party. In the car, Jerry gave Wayne a new blouse and skirt, which he changed into as they rode. Thoughtfully, Jerry had also brought along a bra, panties, footwear, and two kitty cat barrettes. Wayne didn't know Jerry had given Leon his spare key, so Winnie was very surprised to find the other men were all waiting for him in the co-op. They ate more food, gave the girl more presents and played games that his young friends never even dreamed of. Rusty and Harrison fucked her on the couch, pushing her panty crotch to one side to gain access. Then she changed into the new nightie that Harrison gave her. Like all her nighties, it barely covered her hips. He fucked her and at last Uncle gave her her final birthday fuck. Harrison, Jerry and Winnie slept in the bed, Leon on the couch, and Rusty on the recliner. Saturday morning, the fucks resumed.
"What are we going to do today, Uncle? Go to the store? the park? I gotta know so I know what clothes to wear." This was the lad who used to wear a T shirt and jeans regardless of the occasion.
"Well, as you know, Winnie. We can do whatever the hell we want. But the weatherman said it's going to be a scorcher today, so..." He reached behind the couch and pulled out a bag with a gift Wayne had not seen. "...so, I bought you this and we can try it out today if you want?" The other men all winked at each other.
Winnie tore open the wrapping and pulled out a bathing suit. A one-piece girls' bathing suit with a mermaid appliquéd on the front. "You mean we can go to the beach?" Jerry nodded. "Yippee!" Winnie pulled off her nightie and took up the bathing suit. "Hey, you perverts! Stop looking at me. Hehehe." They covered their eyes but peeked through their fingers, as Winnie pulled her new bathing suit on. Even in lycra, her tiny cock was invisible. "But what the fuck will you guys wear?" Of course all the men knew what was coming and had brought along their trunks (Leon wore a speedo) and plenty of lotion. They had a great day at Jones Beach playing in the sand and splashing in the surf. That night, back in the co-op they discovered they all had tan lines, even Leon. Only one problem: Wayne's tan line was not that of a little boy. He decided he better not let his parents see him without a shirt on.
.oOo.
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.