“I didn’t bring anything to swim in.” Jack said as he returned from the bathroom. It had only been about an hour since he and Caitlyn had been put to bed for their nap, but he had needed to go badly. “I could run back to my cabin.”
“Don’t worry about it. I think we have an old swimsuit of Kyle’s around here that should fit you.” Michael said. “Why don’t you come with me and we’ll go ask him?” Jack could not see the harm in that, so he agreed. “Caitlyn, get changed into your swimsuit while Jack and I go find him something.”
Jack followed Michael upstairs to Kyle’s room, remaining silent as Michael asked Kyle if he had a swimsuit that Jack could borrow. The glimpse he got of Kyle’s room filled him with jealousy. It looked so much like his room back home that he could not help but feel cheated that he had spent the entire day so far in Caitlyn’s little girl room.
“Caitlyn didn’t have one he could borrow?” Jessie teased. Jack glared at her.
“He’s a bit too big for Caitlyn’s swimsuits, Jessie.” Michael said with a smile. Jack’s ears burned. That was not the only reason for him to not wear one of hers! “Plus, they’re not really your style, right?” Jack bashfully nodded, causing Michael to chuckle.
“Here, he can wear these.” Kyle said, handing Michael a pair of Spider-Man swim trunks.
“Thanks, Kyle.” Jack said immediately, eager to break the ice. He knew that Kyle was his age, but he was having trouble remembering that. There was just something about Kyle that made him seem older, more mature.
“Why do you still have these?” Michael asked, holding them up. “They can’t possibly fit you anymore!”
“I left them here a couple years ago.” Kyle replied with a shrug. “If they’re too small for Jack, he can borrow my other pair.”
“Or I can run back to my cabin.” Jack said, trying to sound as helpful as he could.
“We’ll try these first, Jack.” Michael said gently. “But it’s very nice of you to offer.” He closed Kyle’s door and pointed across the hall. “Why don’t you pop in there and put them on?” Taking the Spider-Man swim trunks, Jack disappeared into the bathroom and quickly pulled them on.
He glanced at himself in the mirror and sighed. He had always looked younger than he was, but seeing Kyle reminded him a bit too much of just how young he looked for his age. The juvenile swim trunks definitely did not help.
In a word, they were small. They barely covered more skin than his underwear and they were nearly as tight. It must have been more like four years or so since they had fit Kyle. Maybe he could lie and tell Michael that they did not fit? Then he could run back to his cabin and get his. They were hanging on the railing of the porch from the night before, after all. It would not be a big deal at all.
“Everything okay in here?” Michael asked as he opened the door. “Oh, those should work perfectly.”
“Um”
“I know, they’re a little snug, but it’ll just remind you to bring your own trunks next time.” Michael said with a chuckle. “Besides, you’ve worn worse the last couple days, huh?” He saw Jack’s ears go red and figured that that was reply enough.
Caitlyn was wearing a yellow and blue one piece swimsuit, bouncing up and down eagerly. She seemed a bit disappointed to see Jack in boy’s swim trunks, but she still ran over to hug him.
“Are you excited to swim?” She asked.
“Yeah.”
“Let’s grab you two some towels first.” Michael said. “I think I might even have a Spider-Man beach towel somewhere.” At first, Jack was embarrassed, but then he realized that it could be worse, so he feigned a smile. “You’ve taken swim lessons, Jack?”
“No, but I know how to swim.”
“Ah.” Michael said as he handed him the promised beach towel. “Caitlyn isn’t a certified swimmer yet either, so I’ll need both of you to stay pretty shallow.” Jack nodded grimly. He should have known that there would be something that would keep him from really enjoying this. He tugged on the leg of his swim trunks, wishing that they would go longer than they did. “Alright, I think we’re all set!”
“I’m back!” Diane called, stepping into the cabin. She saw Jack and Caitlyn’s attire. “Going swimming?”
“We are!” Caitlyn bounced again.
“And did you have a nice nap?” Diane looked at Jack expectantly.
“Yeah.” Jack muttered.
“We’re going down to the lake if you want to join us. Might be easier to have two sets of eyes on these two.” Michael said with a chuckle. Diane set her bag down by the dining room table and nodded. She gave Jack a look that said he would need to be on his absolute best behavior.
“Race you to the lake!” Caitlyn said, charging toward it the second they crossed the threshold to the porch. Jack quickly gave chase, the tightness of his trunks on his thighs hindering him to a certain degree. “Last one there’s a rotten egg!” Caitlyn yelled, looking over her shoulder.
“It’s a tie!” Diane called as they reached the shore of the lake. Caitlyn and Jack looked at each other with a smile on their faces. Neither of them had paid enough attention to really see who had won, so they accepted the result amiably.
“Can we go swimming now, Daddy?”
“Sunscreen and water wings first, princess.”
“You too, Jack.” Diane said. “Sunscreen and water wings for both of you.” She saw Jack’s eyes widen. “What do you think, Michael? Can Jack go without water wings?”
“He told me he’s never had swimming lessons, so it might be a good idea. I have two pairs, so it wouldn’t be an inconvenience.”
“Come here, Jack, and let me get sunscreen on you.” Diane said, rubbing it all over her son’s back and chest.
“Mom, please.” Jack whispered, eyeing the bright pink water wings with clear dismay. Caitlyn had gotten the yellow and blue pair, leaving him with these.
“Jack, it’s not that big of a deal. Just wear them for me. It’s for safety’s sake.”
“No!”
“Jack, I don’t like that tone.” She said. “A good little boy would wear them.” She could almost feel the anger rising off of him.
“But”
“Look, Caitlyn’s already in the water. Don’t you want to join her? You’ve had such fun with her today.” Jack had had enough.
“No, mom, listen! I had to play with Caitlyn all day and deal with everyone treating me like a little kid!”
“Jacob Anthony! You are embarrassing me!” Diane said through gritted teeth.
“But mom!”
“You are coming with me into the house right this second.” Michael watched Caitlyn play in the water, pretending not to notice Diane dragging Jack by the wrist into the cabin.
“Mom!”
“I have had it up to here with your attitude, mister.” She said, sitting down on the chair in the dining room she had placed her bag next to. “You’ll be receiving a spanking and then” her voice trailed off. “Well, we’ll start with the spanking.”
“Right here?”
“Yeah. As long as you don’t scream and yell, I doubt we’ll attract much attention.” Jack sighed and took his place across her lap. “It’s just a short one.” She lowered his swim trunks down to his ankles and gave his bottom an almost affectionate pat. “Only a few spanks.”
“To remind me to be a good little boy?” He asked softly.
“Well, since you’re clearly incapable of that” before she finished her thought, she quickly doled out six strikes across his slightly raised buttocks. He bit his lip trying to keep from crying out. In the silence following the spanking, he listened for the sound of Kyle’s door opening upstairs. Hearing nothing, he breathed a sigh of relief.
“Thank you for spanking me, Mommy.” He mumbled, eager to try and get back on her good side.
“Remarkable how quickly your behavior changes.” She casually pulled his swim trunks off the rest of the way. “Stand up for mommy.” He complied, feeling so strange standing completely naked in the neighbors’ kitchen. “Now, which is it? Do you not want to be a good little boy or are you incapable of it?” He remained silent, not meeting her gaze. “Michael says you’ve been mostly behaved today, only arguing about as much as Caitlyn has, but this outburst down by the lake is too much, Jack. You cannot keep behaving like this. It is embarrassing for me and I’m not sure why it doesn’t seem to bother you in the slightest.”
“Sorry.” He mumbled. “Mommy.” He added.
“Saying a few nice words isn’t going to cut it, Jack.” She looked at him. He was so capable of at least looking like he was sincerely remorseful for what he had done. “I need to make sure that you mean it.” She reached down into her bag and pulled out a pink garment. Jack’s eyes widened. It was a bright pink girls’ swimsuit with a little white bow on the chest and, most distressingly of all, a pink tutu around the waist. “I’ve given you more than enough of a chance to behave. Since you refuse to be a good little boy, you’ll be mommy’s good little girl for the rest of our visit to Michael’s cabin.”
“But” he stopped talking, knowing that he stood a good chance of just digging himself deeper.
“Or would you prefer to be Mommy’s little princess?” She asked. “No, I think Mommy’s good little girl is enough, hmm?” Jack did not answer, so she leaned forward and held out the swimsuit for him to step into. He bashfully did so. “I have to say, this fits you much better than those too-small trunks did.” Diane said. Jack remained silent. His mom reached into the bag and pulled out one last item.
“A bow?” He quickly retreated back into silence after the outburst, hoping it would not earn him further punishment.
“Caitlyn has her hair in braids, so I figured you need an accessory too.” Jack stood as still as possible, seething as she put the big pink bow on top of his head. “There, that shouldn’t fall off as long as you’re careful.” She hugged him close. “Let’s get you back outside. You’re going to put on those water wings and play with Caitlyn, do I make myself clear?”
“Yes, mommy.” Jack intoned. She patted him on the shoulder and they walked back out to the lakeshore. Jack tried without any luck to stop the tutu from bouncing with every step. It seemed to draw even more attention to the sissy boy with the grim expression.
Caitlyn, of course, was effervescent about Jack’s new attire, laughing with delight as he stoically allowed his mom to put the pink water wings on his arms. He knew that he looked ridiculous based solely on the smile his mom wore.
“Alright, all set.” She said. Jack shuffled down to the water and stepped in, a bit hesitant due to the coolness, but he also wanted to submerge at least the lower half of his humiliating swimsuit. What if Jessie and Kyle came out? He would never live this down.
“I love your new swimsuit, Jack.” Caitlyn said.
“Thanks.” He mumbled, his hands playing with the tutu. Caitlyn immediately splashed him and he had no choice but to splash back, beginning an all-out splash war.
Once their energy had faded, Caitlyn and Jack sat down in the water and simply enjoyed the day. After a bit, they were shepherded out of the water by their parents and wrapped in towels before being vigorously dried off. Jack grabbed the towel from his mom as quickly as he could, desperate to regain some semblance of agency.
Hearing the screen door of the cabin open, he quickly wrapped the towel around himself to try and conceal his feminine swimsuit from Jessie and Kyle as they emerged from the cabin, clad in their swimsuits. She wore the same black and white bikini that she had worn the evening before when she and Jack had gone swimming at their cabin. She had begged Diane for it for a whole week before she finally relented. Kyle wore a pair of brown swimming trunks with a white stripe on the side, far more appropriate for a boy his age than the pink swimsuit Jack had on under his towel. He instinctively pulled the towel tighter around him, grateful for just how enormous it was.
“Did we miss swim time?” Jessie called as they approached.
“Jack, are you done swimming?” Diane asked. He nodded.
“C’mon, Jack.” Jessie said, grinning. “We’re going to jump off the end of the dock. You love doing that!”
“She’s right, Jack.” Diane said. “Just do it once.”
“But mommy” he hissed.
“You don’t have to if you don’t want to.” Diane said.
“C’mon Jack! Just do it once! Please!” Jessie pleaded. Jack eyed her suspiciously. She must know something. With a gulp, he realized that, even though he had his swimsuit hidden, there was a giant pink bow on top of his head. Jessie had to know he had something embarrassing on! A mischievous glimmer appeared in her eye. “Bet I can jump farther out than you can.” Jack felt his competitive spirit rise, but then he reminded himself of the swimsuit he wore.
“Nuh-uh! Jack can jump a lot farther!” Caitlyn interjected. “I know he can!” With Caitlyn firmly supporting him, Jack had no choice but to drop the towel.
Desperate to own the moment, Jack did a turn so that Jessie and Kyle could see every angle of his new swimwear, water wings and all.
“Take it all in.” He said with a bit more of an edge to his voice.
“Didn’t like the Spider-Man trunks?” Jessie asked, but her voice was a bit softer. Jack had succeeded, it seemed, in seizing the upper hand. He could not help but stand a bit taller, nearly level with Jessie.
“Pink’s more my color.” Jack managed to reply even as a wave of revulsion hit him. He wondered what Kyle thought, but the other boy seemed as aloof and uninterested in Jack as ever. “So, are we going to see who can jump farther or not?” He could feel his nerve about to leave him and he had to resist the urge to pick the towel up again to hide his outfit. Resummoning his nerve, he turned and hurried to the dock. “Run the whole length and jump off?” He asked. Jessie nodded, taking her place next to her brother.
“Be safe, kids!” Michael called. Caitlyn stood next to him, nervously watching her friend and his sister.
“Kyle, can you be the judge?” Kyle simply nodded and stood far enough away from the dock so that he could easily see the distance each of them jumped.
“Who goes first?” Jack asked.
“You” Jessie said at once, stepping slightly aside so that he was alone on the dock. He readied himself, determined to beat Jessie, no matter what it took. “Wait!” Jessie yelled, breaking his focus. “Do you want me to keep your bow safe for you?” He stared at her for a moment until he remembered the prissy bow on his head.
“Yeah.” He muttered through gritted teeth. She smirked and helped him get it out of his hair. He knew that it would return to its place far too soon for his liking.
Returning to focusing himself, he broke into a run, pounding down the dock, tutu bouncing with every step. Refusing to allow that to bother him, he launched himself off of the end of the dock. He plunged into the lake before bursting back up with a grin. He knew without a doubt that he had won, even before Jessie took her turn. She charged down the dock and he held his breath without even realizing it as she took flight.
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 77073 times)
