The Annual Ski Trip (A story about gender discovery)

Hi, I may have posted parts of this story here in the past, I don’t recall. At any rate, I’m trying to get back into this story to at least give it a conclusion then perhaps move on to a sequel. I’ll post a chapter every other day for the next little while I have five complete I think. I’d would really like some feed back, open to suggestions etc. Anyway without further ado, here’s chapter one.


When their family was getting ready for their annual ski trip Chris’s mom had bought him a new pair of long underwear. When he tried them on he couldn’t help but notice how they clung to his legs. “Mom they make me look like I have chicken legs!” Chris had always had a small frame and had been teased for it in the past.

“It’s not as if anyone’s going to see your legs Chris. You’ll be wearing your ski pants. They’re just long johns.”

“But what about in the chalet?”

“Well I never expected you to wear them on their own, wear some sweatpants over them if you think you’ll need to take your ski pants off.”


“Go make sure your sister is packing”

On his way back to his room Chris knocked on his older sister’s door. “Yeah what?” His sister Kathryn opened the door and saw her brother. “Why are you wearing leggings?”

“They’re not leggings, they’re long johns for the trip. Anyway mom wanted me to make sure you were almost packed. Are you seriously bringing a suitcase that big?”

“Whatever you say, looks an awful lot like leggings to me and yeah I’m almost ready. I’ve gotta be ready for any eventuality there could be cute boys there I have to have lots of dresses and stuff for the evenings and dresses means shoes and lots of make up even a couple hair extensions in case I want to change things up, a couple swimsuits in case I get invited hot tubbing.”

As he went back to his room to finish packing Chris felt even more self-conscious. He finished packing making sure he had pants to wear skiing over his long underwear.

In a short time they had loaded the car and were off. They arrived in a few hours at the lodge they usually rented. The family all piled out of the car and into the lodge.

“You’ve got a few hours before the lifts close, why don’t you guys hit the slopes for while. Your mom and I will unpack the groceries.” Chris’ dad told the two kids.

Chris and Kate got ready. Chris making sure to put his track pants over his long johns before putting on his ski pants and boots.

Chris and Kate headed out to the slopes. For siblings they got along fairly well. Kate was 20 and went to college close to home. She was quite pretty and had been reasonably popular around school, a cheerleader and volleyball player. She knew her brother didn’t have a lot of friends so she was nice enough to him and even let him sit with her at lunch in school now and then when they had been in high school together. Chris was 18 and what a lot of people would call a nerd. He enjoyed Dungeons and Dragons with his few friends as well as being interested in Star Wars, Lord of the Rings and the like. He was part of the local swim team and was pretty good despite his small frame as his muscles were toned; he was actually shorter than his sister. (The swim team was in offseason now so his hair was longer than the brush cut he kept when he was swimming 6 days a week)

Their family had been taking this ski trip for as long as Chris could remember so they were both quite good. To warm up they went a few times down a couple of the easier runs. Eventually hitting a black diamond before heading into the chalet. They propped their skis up outside and headed inside pulling off the rest of their gear and hanging it up in lockers. They ordered hot chocolates before sitting down in the lounge. They had both worked up quite a sweat and were chugging water while they waited for their hot chocolate. “See anyone you know around?” Chris asked Kate.

“Can’t say I do, most of my friends are gone to the beach this year for spring break. Your track pants are all sweaty, you know you don’t have to be so worried about your long underwear, see all the guys around here are wearing Under Armor compression pants and stuff.”

Chris looked around and realized that the new trend seemed to be wearing these sorts of compression pants and almost everyone was wearing them. A lot of the girls were wearing spandex leggings and a lot of guys were too though some were wearing track pants like Chris. “Yeah I guess it’s not that big of a deal is it. It’s not that different from my swim team shorts, just longer.”

“Exactly, besides it looks like you sweat all the way through your track pants, maybe one layer too many don’t you think?”

“Yeah I guess.” They received their hot chocolates and drank them, chatting about the rest of the trip. There was a concert on the weekend featuring a band they both liked so they bought tickets before heading back to the lodge for dinner with their parents. They ate their supper, showered and headed to bed, as they were pretty tired from the road trip and first few hours of skiing.

Chapter 2

The next morning they all got up and ate a big breakfast. Chris went to get ready for a full day of skiing, “Mom, my long johns are still damp from last night they got all sweaty. I can’t wear them today.”

“Just wear your sweatpants.”

“They make me, well, they make me sweat too much. That’s why my long johns are still damp.”

“I don’t know what to tell you son,” His dad said as Chris looked to him, on his way up to his room to look for something to wear he stopped by Kate’s room.
“Don’t wait for me Kate I have to put my long johns in the dryer.”

“I don’t wanna ski with mom and dad, don’t you have something else to wear? Can’t you just keep your pyjama pants on”

“No, I only had the one pair of long johns, and anything extra will make me crazy sweaty again.” Kate opened the bedroom door she was wearing neon green spandex leggings and a black long sleeved top, her brown hair in a braid down her neck.

“Our legs are close to the same length you haven’t got the same uh… shape as me but leggings don’t have any shape either so give these a try.” Kate handed Chris a pair of purple spandex leggings.

“You don’t have any other colours that are less girly?” Kate held up neon pink and an even brighter purple as well as bright blue and a pair of yellow. Chris took the blue ones only to realize they had pink stars and hearts dotted all over them.

“Sorry bro I guess not really.” Chris finally took the yellow ones and went to get dressed. The yellow leggings made him feel like he had even more chicken like legs. He got his ski pants, boots, and coat on and headed with the rest of the family to the slopes.

He had to admit he could move and ski a lot easier without another layer on his legs. Like last night, he and Kate stuck together. They warmed their way up to the harder runs and were pretty hungry by the time they quit for lunch. They left their skis outside the lodge and headed indoors to get out of their gear. Chris went to the bathroom when they got inside. Kate was by a locker getting out of her coat when a tall handsome guy came up and started talking to her. He had long hair and a beard that was wet with snow. His name was Jordan and he was around Kate’s age. Kate asked him to ski with her after lunch but he had to decline her invitation because he couldn’t leave his brother by himself all afternoon. Jordan introduced his brother when he came to the locker, Jamie was 18 and tall, not unlike his brother, but a little skinnier, the other difference was Jamie was clean-shaven.

“You don’t have a girl friend or a sister perchance?” Jordan asked.

“No I’m just here with my brother.” Kate said.

“Well maybe if I can find someone Jamie can ski with, I’ll catch up with you.” Jordan and Jamie headed off to get something to eat.

Chris came out of the rest room and got out of his ski gear. He was happy to have gone with the leggings he didn’t feel out of place at all. He bent over to undo his boots and Kate couldn’t help but notice that Chris had more shape than she thought. They headed to the lounge and ordered lunch.

“So I met someone when you were in the bathroom.”

“Oh you mean like a guy?”

“Yeah, he’s super cute too. He’s right over there.” Kate pointed to Jordan across the lounge

“Feel free to ditch me, you were nice enough to stay with me this long.”

“Don’t worry he won’t ditch his brother for me, unless he’s got a to hang out with too.”

Chris brushed his hair off his forehead. “Oh, sorry about that then sis.” They ate their lunch and headed back to the slopes and skied again into evening. Kate caught occasional glimpses of Jordan and Jamie skiing and watched them longingly. Chris couldn’t help but notice that Kate seemed a little disinterested in skiing and was watching this guy, Jordan, she had talked about. The brother was a good skier too they were always racing, trading places with each other.

They headed back to their lodge and met their parents for dinner. While they were eating, their parents told them that there was urgent business back home with the real estate company that required their attention. There was no reason Kate and Chris couldn’t stay alone, the lodge was already paid for. They left a credit card with them for emergencies and left after supper.
Chris and Kate did the dishes and then washed up and got ready for bed. After showering Chris knocked on Kate’s door.

Chris was wearing his pyjama pants and an undershirt. Kate answered her door wearing an oversized t-shirt with her wet hair wrapped up in a towel. “So I was thinking.”

“Thinking about what?”

“Your little predicament with that guy you met and the brother”

“Yeah what about it?”

“Well is there anything I could do to help?”

“Unless you think you can appeal to a macho teenage guy I doubt it.” Then a light bulb went off in Kate’s head. “Say I have an idea, it’s a bit extreme but I think it could work.” Chris gave Kate a bit of a concerned look.

“I was thinking more along the lines of just hanging out with the guy.”

“Yeah well you’d be hanging out with him, but I have a feeling he’d prefer to have a companion of the fairer sex.”

“Well how am I supposed to help with that?”

“It wouldn’t take too much.”

“Too much what?”


“Work to do what?”

“To make you like a girl”

“Wait you want me to be a girl?”

“Sure, you’re small enough, we’re close to the same size. We just need to pick up a few things at the mall.”


“Well your ski gear isn’t exactly feminine. Plus we can just use mom and dad’s card.”

“I guess, I mean you’ve done a lot for me since I got to high school, I’d be in nerd hell without you.”

“Great we’ll start in the morning.” Chris was tired so even though he had a lot on his mind he fell to sleep quickly.