Secluded Cabin Sissy

[bobbie99]

I love this story.  It shows a lot of imagination and it is fresh.  Having a single dad next door with two kids was unexpected. 
How tall is Jack?  If he is a bit shorter than his sister then he could be as much as three inches shorter.  If his sister is average then Jack would be at the lower end of the height scale for a boy his age
I believe Michal believes that Jack has a pants wetting problem and is going out of his was way helping Jack with his problem.  This is to impress Diane which is his love interest.  Diane may have mentioned Jack’s wetting problems when they met the day before.  So I would expect Jack will be having more accidents.

[Andlat]

Bobbie99 - Thanks for commenting! I get the feeling you just "binged" it all at once, so welcome, even if that's not the case! I've gotten a few questions already about the heights because I don't really have an editor reading this for me, I've had my share of continuity problems. Suffice to say, Jack's a little under average for a boy his age, Jessie's an inch taller than him and Kyle is "at least" three inches taller than Jack. I'm a big proponent of readers' images of characters, so if you imagine them differently, all the better. I have a set image of them all in my head, but I sometimes have trouble translating mental images into words. I'm certainly still learning as a writer.

I enjoy hearing readers' theories about the motivations of the various people in the story. I try to sprinkle foreshadowing throughout the story, so when theories line up with what will be revealed in the future, it makes me smile. It also makes me smile when the theories aren't what I have planned because it means readers are engaging with the story, so keep them coming! Tell me about how Denise is actually an alien who's using mind control to manipulate the whole summer. Go crazy! :)

[moms.cross.dresser]

now maybe after swimming back into diaper and onesie

[babycakes]

Andlat, another excellent segment and further glimpses into the characters.  I have decided to do some speculating and character interpretation based on the encouragement you gave Bobbie99

Diane, in my opinion, is starting to show her true colors as a cold harted b....h. First she allows the neighbors to believe Jack is younger than his age and encourages his feminization through play with the much younger Caitlyn.  Then, when Jack rightly objects to wearing the water wings since he is fully capable of swimming as evidenced by his prior day swim with Jessie, she spanks him and dresses him in an  exaggerated girl's suit with tutu and bow in his hair.  I don't trust Diane at all at this point and neither should Jack.  He should just walk away at the earliest opportunity.  I expect her character to get nastier as the story unfolds.  Perhaps she's taking out her anger at her former husband for leaving her (don't know whether they divorced or he died).

Jack, for all his apparent whiny compliance with everyone else's wishes has finally shown some gumption with his response to Jessie's challenge to jump farthest into the water.  I pray that this character continues to demonstrate, even if passively, that no one is going to beat him, even mommy dearest.  I also wish he had told Jessie to leave the bow in but stripped off the tutu to improve his jump.

Jessie seems to be a prototypical sibling with a bit of a mean edge of passive-aggressiveness as demonstrated by her jumping challenge to Jack so she could see what he was wearing and enjoy his embarrassment.  Classic that Diane virtually never corrects or punishes Jessie.

Michael is actually starting to become very interesting.  He never seems to defend Jack against Diane.  Not that he should generally interfere with a parent's interrogative but Michael seems to reinforce Diane's regression and feminization of Jack with the little boy swim trunks, the nap, the cut up PBJ sandwich consistent with Caitlyn, and his lack of response when Jack objects to the water wings, to name a few.  With not a lot to go on but an overall picture of this character I will hazard a guess that Michael is Denise's "daughter" who was regressed and sissified at the cabin where Jack and family are staying.  His apparent subservience to Diane seems to support this hypothesis.  The fact that the cabin is "secluded" but has a neighbor within walking distance might mean Denise owns both properties and she has and continues to use them to sissify boys and men.  Michael may be afraid that Diane will regress and feminize him if he doesn't support her and Denise can always visit to assist Diane.

Kyle has been described as aloof but I think it is fear that has him staying distant from Jack.  I believe he has been subjected to the same treatment  as Jack and is afraid of it being imposed again.  If I am correct about Denise being Michael's mother or at least a relative, it's highly likely that Kyle has been regressed and feminized.  Caitlyn's comfort with Jack as a baby girl also supports this position.

Caitly seems more of a catalyst in Jack's feminization and regression.  At her age I can't see anything deeper in this character. 

I realize that my comments may be longer than parts of your story and so I apologize if you find them offensive; however, you did seem to encourage such discourse in your prior comments.  Thanks for your excellent work.

[Andlat]

Jessie splashed into the water not far from Jack, but he knew that he had won. He grinned and started swimming back toward the shore to celebrate his victory. Caitlyn was jumping up and down excitedly and even his mom and Michael looked impressed. Jack could not even say how much his success had meant to him. Even stepping out of the lake in his sissy swimsuit could not dampen his spirits.

“Must be late for ballet class.” Jessie called after him as he emerged from the lake. He grabbed his towel, ignoring her and wrapping it around his waist. Jessie shrugged and called for Kyle to join her in the lake. He complied as Caitlyn came over to Jack.

“You jumped so far!” She said, eyes wide and shining with admiration. “Oh, Jessie gave me your bow to hold on to. Let’s go ask your mommy to put it back in your hair.” She grabbed Jack’s hand and tugged. He sighed, knowing that his mom would expect it of him. “I’m glad you’re dressed like a girl again.” She said as they walked over to Diane, who Jack knew could hear Caitlyn’s continuous monologue. “Boy clothes looked weird on you.” She smiled up at Diane. “Here’s Jack’s bow, Miss Diane!”

“Thank you very much, Caitlyn.” Diane said, taking it from her and quickly reattaching it to Jack’s short hair. He was not even sure how she did it.

“Is Jack going to wear diapers again?”

“Not yet. He’ll be staying in his swimsuit for a while. I didn’t bring a change of clothes for him.” Jack looked at his mom inquisitively, but remained silent. “Do you like his swimsuit?”

“It’s okay. I think Jack likes pink more than I do though.”

“Huh?” Jack looked down at her in confusion.

“I heard you tell Jessie that pink’s your color.”

“You did say that, Jack.” Diane said with a laugh. Michael came over.

“Grill’s lit for our early dinner.” He said. “Caitlyn, if you’re done swimming, why don’t you run inside and get changed?”

“Can Jack come with?”

“He’s still wet, sweetie. You go get changed and then you and Jack can play again while you wait for dinner, okay?” Caitlyn nodded and hurried inside, waving back at Jack. “She’s an energetic one.” Michael said with a chuckle. “And she certainly seems to like you, Jack.”

“Yeah.” Jack said. “It’s tough keeping up with her sometimes.”

“That it is.” Michael grinned. “That it is. Every year, we hope one of the neighboring cabins will have a girl around her age to keep her occupied. Kyle tries to play with her, but he’s not always the most willing.” He looked out at the lake where Kyle and Jessie were playing an informal game of Marco Polo. “I’m sure this’ll embarrass you, Jack, but you’re honestly the closest thing to a girl her own age we’ve ever had at the cabins. You must have played a lot of girl games growing up with Jessie?”

“Definitely.” Diane interjected with a fond smile. “I eventually had to sign Jack up for Little League just to get him some time with other boys.” Jack looked at her. Standing there in a pink swimsuit that his mom had put him in to make him be a good little ‘girl’, he wondered why she was talking like this.

“Kyle and Caitlyn are far apart enough in age that they just kind of stay in their own spheres. Kyle tends to disappear whenever Caitlyn has friends over, but Caitlyn always wants to play with his friends. That’s why she’s so excited about you, Jack. You’re an older boy who plays her games.” Jack nodded, pulling the towel tighter around him. He felt almost like a grown-up in this conversation and he did not want his swimsuit to remind his mom and MIchael that he was steadily becoming more and more of a little girl in their eyes. “Anyway, I better get the meat from inside.

Jack sat on the nearby bench, holding the faded Spider-man towel around himself, trying to cover up his swimsuit as much as possible. Diane sat down next to him, slightly adjusting the bow that he had forgotten was still atop his head.

“It’s a shame your hair isn’t longer. You’d look so cute in pigtails or braids like Caitlyn’s.”

“Mom!” She gave him a look. “I mean, mommy!”

“Well, you’re being a little girl right now, remember?” She gave him a hug. “You look so much like Jessie that it’s not hard to imagine you with longer hair. But, it would take a while to grow it out.” He could not even say how grateful he was that that was the case.

“Can I go back to my clothes when we get back to the cabin?” He asked, knowing that there was little chance it would happen any sooner.

“I’m not sure, Jack.” His mom replied. “You’re a lot better behaved as a girl than as a boy.” She smiled at his face. “But, but.” She added to mollify him. “I’m not too keen on changing your diapers this whole vacation.”

“That’s a relief.” He muttered.

“You should be glad I don’t put it up for a vote. Jessie and Caitlyn would team up and probably get rid of all your boy clothes before you even knew what happened!” She chuckled at the thought.

“I still think it’s weird that you’re making me do this.”

“I know, Jack, I know.” She said gently. He sighed.

“Can I go change?”

“Into what?” She asked. “I’ve packed up your clothes. You won’t be wearing them again for a while.”

“But” Jack could feel tears welling up in his eyes. “I’m trying really hard to behave, mom, but it’s just so embarrassing being treated the same as Caitlyn!”

“I know, Jack, I know. I can’t say why, but you really do behave better dressed like this than you did in your regular clothes.”

“So, I’m stuck like this?”

“For now. Like I said earlier, we won’t do diapers, at least during the day.” She hugged him. “You’ll wear the dresses in the nursery again, but what we’ll do for underwear, I’m not sure. Probably just let you wear your regular undies under them.” She smiled. “It’ll be strange, but I think that’ll just have to work.”

“I promise I’ll behave.”

“I know, but you seem to forget your promises pretty quickly, don’t you?” A few tears of frustration slid down Jack’s cheek. She hugged him again.

“You're really going to keep me in dresses?” Jack asked.

“Yes, but you’ll get to pick them yourself. I know you can’t imagine yourself picking out a dress, but it’s what’ll happen.” She replied. “But remember, you’ll wear your own underwear under them, so it’s not all bad.”

“Not at night.” Jack muttered.

“Right. You’re still going to wear diapers at night. Your little dash to the bathroom this morning made me and Jessie nervous.”

“What about swimming?”

“Well, I suspect Jessie will have you go swimming everyday once she realizes you’ll be wearing your new pink swimsuit.” She smiled, moving his towel slightly out of the way as if he did not remember that he had it on. “But, if you cooperate with this, you might just find yourself earning your boy clothes back. If you don’t cooperate though, I won’t hesitate to take you into town to buy some panties. Maybe even get your ears pierced and your nails done.” The look of horror on his face almost made Diane regret mentioning it. “That’s just if the dresses don’t seem to be working.”

“There must be some way to keep Jessie from teasing me constantly.”

“You know your sister, Jack. She’ll tease you until you stop letting it bother you. You’re obviously getting to that point, so just keep it up.” Jack nodded, but he wished his mom would intervene more. “Oh, remind me to take a photo of you and Jessie in your swimsuits.”

“Mom!”

“Oh, come on! I didn’t take any pictures of baby Jackie, let me at least get a couple of you in your pretty pink swimsuit.” She hugged him again, but he did not know if she was joking or not.

Caitlyn emerged from the cabin in a denim skirt and a yellow t-shirt, carrying both Petite Belle and Sterling Sparkles in her arms. She skipped over to Jack.

“Here’s your pony, Jack. Let’s pretend they’re flying again.”

“What’s your pony’s name, Jack?” Diane asked.

“Sterling Sparkles.” Jack replied softly. She smiled and eased the towel off of his shoulders.

“Go play with Caitlyn, Jack.”

“Can’t I wear the towel?” He asked.

“I think it would be tough to run around if you’re worried about the towel, but if you want to try, you can.” He knew that she was right, but he was too stubborn to admit it. Draping it over his shoulders like a cape, he tried to tie it around his neck, with little success. Diane watched, patiently smiling.

“C’mon, Jack!” Caitlyn whined. “Petite Belle and Sterling Sparkles need to get to the Frost Queen’s castle before it’s too late!” Jack sighed and tossed the towel on the picnic table.

Encouraged by the presence of an audience, Caitlyn insisted they do more than simply run around. Jack followed her as they skipped, pranced, and did a variety of other activities always in the sight of either his mom or Caitlyn’s dad. Throughout it all, Jack felt terribly exposed, dressed as he was in nothing but the pink swimsuit. He could hear the snickers once Jessie emerged from the lake to see him playing with Caitlyn, but there was nothing he could do with his towel over by his mom.

“Girls! Dinnertime!” Michael called. Jack could not be sure that he had actually said ‘girls’, but that was what it had sounded like. He hurried over to the picnic table with Caitlyn, glad that it appeared as though everyone would be eating this meal together. “Who wants a burger and who wants a hot dog?” Michael asked. “Got plenty of both!”

* * *

Once dinner was done, Michael wiped Caitlyn’s face and Jack had his wiped by his mom before he could even protest. Kyle sagely scrubbed his own to make sure he did not get the same treatment.

“I suppose we’d better get back to our cabin.” Diane said.

“Yeah, it’ll be bedtime for a certain little girl soon.” Michael patted Caitlyn’s shoulder.

“Yeah, Jack.” Jessie whispered to him. Jack tried to kick her under the table, but missed.

“Say your goodbyes, kids.” Michael said.

“Can’t Jack spend the night?”

“Not tonight.” Michael said. “But maybe we can play a sleepover sometime soon?” Jack looked less than enthused.

“Ok. Bye, Jack! I hope I get to see you again tomorrow.” She hugged him and Jack shyly returned the hug. Kyle quietly said good-bye to Jessie and disappeared inside before Jack could even blink, it seemed.

“Let’s go, kids.” Diane said, standing up. “Thank you very much for a lovely day, Michael. We’ll have to get the families together again soon.” Michael smiled and nodded.

“I think they’ll all like that.”

[Plateguy]

Hi Andlat, thanks for the new chapter.  Poor Jack is right back to where he was no matter how much he tries to satisfy the monster that is his mother.  Will he ever ask her why she hates him so much?  I imagine the pics she is taking will be used at home to force him to do exactly what Diane and Jessie both make him do.

[bobbie99]

This is a great story presented in a way that the reader feels and identifies with the humiliation James is experiencing.  Very good writing.  Use of the sibling rivalry and a mom that can see no wrong in her daughter is classic.
James should only realize how lucky he is.  I sure hope that this is at least a two-week vacation.  Please keep this story going in the current direction.  We readers are loving it.