Sea Breeze by tfes8

Content Warning: Transphobic reaction

Chris was looking forward to this vacation for a long time. His family was set to board a cruise ship and this was the first time his parents brought him and his sister. Previously, his parents left the kids with a family member. But now Chris was 24 and his sister 21 so their parents decided they were adult enough to bring them along.

He didn’t know what to think of this vacation. Everything he knew about cruises told him this was a couples thing. Singles didn’t go on cruises. He was single. Hopelessly single.

He had a few girlfriends in college, but ultimately none lasted long after graduation.

Chris’s sister Amanda, on the other hand, had a long-time college boyfriend who wasn’t able to come with Amanda and her family on the cruise.

That meant Chris and Amanda had to share a room together. So much for being treated like adults. But the promise of fun and adventure was worth the sacrifice.

In the morning, Chris wore a brand new white linen shirt and a pair of cargo shorts. He tied his long hair up into a man bun. His mom hated his long hair, and had been pleading with him to cut it for over a year, but he thought it made him look cool and edgy.

Chris and his family boarded a plane to Florida, then they boarded the cruise ship. The long embarkation process had left them parched, so they stopped at the nearest bar for a drink before heading to their cabins.

Chris eyed the drink of the day special and ordered that. A Sea Breeze. A brightly-colored red vodka and cranberry cocktail.

Right off the bat disaster struck.

"Hey Chris, let me try your drink," his sister Amanda asked.

"Sure, Amy," he replied as he handed it to her.

"Ooh," she exclaimed, "too bitter for me."

Chris was distracted by the sight of a cute girl walking through the bar, and failed to grab the drink as Amanda passed it back to him. As a result, the drink spilled all down Chris's white shirt and landed in his lap. He jumped up and tried to get the spilled drink off, but it was too late - his clothes were stained bright red with cranberry juice and he smelled like a bar at closing time.

“What an awful start to our vacation,” Chris thought. “I need to go change my clothes,” Chris told the others.

His family was slightly annoyed cocktail time was cut short, but left the bar and each went towards their respective cabins. Chris and Amanda found their cabin on deck 8 near the back of the ship. Sitting between the beds was Amanda’s suitcase. But not Chris’s.

While Amanda started unpacking, Chris called the guest relations desk to ask about his bag, and they assured him it would be delivered - sometime.

He paced the room. He felt icky and sticky and disgusting. And he reeked of vodka. It was making him nauseous.

“Chris, stop pacing,” Amanda said, opening a drawer and placing clothes in it. “We’re on vacation.”

“You’re not the one that looks like a crime scene! I can’t even change out of this.”

“Would it make you feel better to wear one of my outfits?” she joked.

“What? No!” Chris fumed.

Amanda looked at her older brother and felt bad for him. She grabbed a T-shirt and shorts from her suitcase and handed them to him. “Here. Put these on. I won’t say a thing. Just so you can get out of those.”

Chris looked at the bundle of clothes in his sister’s hands then looked down at his cranberry stained shirt and shorts. “She’s not serious, is she?” he thought. He hesitantly took the clothes and walked to the bathroom.

Amanda held back a giggle as her brother unexpectedly took her suggestion.

He quickly stripped down to his boxers then realized those too were soaked. He took them off and stood there naked, examining what she had given him. A simple gray T-shirt and a pair of jean shorts.

Chris took a quick shower to get rid of the smell. After drying off, he put on the T-shirt. It was skintight but manageable. Then he realized he had no underwear. “Commando? Oh, well, it’s only temporary,” he thought. Next were the shorts. The combination of no underwear and the girl-length shorts meant his junk felt a lot cooler and unrestrained.

He then opened the door and stepped out in the room for his sister to see.

Amanda looked at him. The tight girl’s clothing gave him the appearance of curves and showed off his legs. Granted, her brother was skinny and had long hair tied into a man-bun, so that outfit looked a little feminine on him.

“These shorts are showing a lot of my thighs.”

“So, athletes show just as much skin,” she pointed out. “What’s it with guys and wanting to wear shorts that come down past their knees?”

“We have gross leg hair.” He then pulled out a laundry bag and deposited his dirty clothes in it.

“Don’t worry about it. It’s not noticeable. We were both blessed with blonde hair. I can actually go two weeks without shaving my legs.”

“That’s too much information,” he groused. He didn’t want to know about his sister’s grooming routine. He was glad he wasn’t a girl and didn’t have to shave his legs. 

Just when he sat down to relax, the shipwide alarm went off, taking him by such surprise that he jumped back up.

“All passengers please report to your muster stations,” the intercom politely instructed.

Chris and Amanda shared a glance. Mom and Dad had given them a heads up about this. They were to report to the muster drill where the ship's crew demonstrated safety instructions.

“I can’t leave the cabin like this,” he whined. “I’m dressed like a girl!”

“Yeah, so am I,” she laughed. 

“But you are a girl!”

“Come on, you have to go,” she continued. “You heard Mom and Dad. It’s mandatory.” She looked at her brother again standing there in her clothes. “What if you passed as a girl?”

“Huh?”

Amanda walked over to her suitcase and pulled out a sarong, then she tied it around his waist. The sarong came down to mid-calf. “There, now your legs are covered.”

She dug through her purse and pulled out a pair of sunglasses.”Take your man-bun out.”

He pulled the hair tie out of his hair and the hair fell across his back.

Amanda then gave him a pair of her sunglasses and shook his hair so some strands were in front of his shoulders. Finally, she removed her floppy sun hat and put it on his head. “There, now you look like a girl so nobody will notice.”

Chris was silent. He was deathly afraid to leave the room looking like this.

“Don’t worry, Mom and Dad are on another deck and likely at another muster station,” she pointed out. She opened the door to find other guests walking down the hall towards their assigned muster station.

Chris timidly walked out of the cabin and the two siblings followed the crowd.

When they reached the muster station, they both stood in line. On one side of Chris was Amanda. On his other side was a cute girl that looked to be around his age.

Chris felt embarrassed all over again wearing this outfit. He wished he could just crawl into one of the hanging lifeboats and hide.

“Is this your first cruise?” the girl turned to ask Chris.

Chris looked around to see if she was talking to him. She was looking straight at him. “Yeah.”

“It’s mine too,” she replied looking around.

Minutes went by and everyone was beginning to fidget and look bored.

“When are they going to do this so we can go enjoy the rest of the ship?” the girl wondered out loud.

“My parents cruise all the time,” Chris explained. “They say this is the worst part and once we’re done, our vacation officially starts.”

“Cool. I want my vacation to start now.”

“Me too,” he chuckled.

She giggled then looked at him again. “That’s a cute sarong.”

Chris wanted to reply, “It’s my sister’s,” but instead just said, “Thank you.” He was always taught to return compliments so he looked at the girl and remarked, “That’s a cute sundress.” 

Amanda heard the exchange and looked to see her brother chatting with a cute girl.

“Thank you,” the cute girl said with a smile. “Hey, by the way - my name is Sarah.”

“I’m Chris,” he replied.

“Who are you here with?”

“Just my family. My parents and sister.” He glanced over Amanda who was smiling at this exchange and suddenly turned away.

“I’m here with some college friends,” Sarah replied. “This is our graduation present to ourselves.”

“That’s awesome,” Chris smiled. He hadn’t gotten a chance to flirt with a girl since graduation. She was cute and talking to him.

“You look ready for the pool,” Sarah observed. “I didn’t get a chance to change into my bathing suit before this stupid drill. Want to join me and my friends at the pool after this?”

Chris was beaming with excitement that she wanted to hang out. “Well, this is all I have, they lost my luggage.”

“Oh my God, that sucks. If you need to borrow a swimsuit, let me know.”

Chris’s excitement just dropped off a cliff. It didn’t sound like she was teasing. It sounded like she was serious. “Oh, no, she must think I really am a girl,” Chris thought to himself. “Uh, sure,” Chris timidly squeaked out.

It was then that the crew started the safety drill and took attendance.

When the drill was over Sarah turned to Chris. “See you at the main pools in maybe 30 minutes?”

“Sure!” Chris said enthusiastically. Maybe things were looking up for him. He didn’t want to press his luck, so he quickly left the drill area.

Sarah again turned to ask Chris what cabin he was in, but he was gone. 

When they were away from the crowd, Amanda caught up to him. “Who was that?” she asked Chris, nudging her brother.

“Girl I just met,” he replied, a sudden swagger in his demeanor.

“It sounded like the two of you were flirting.”

He smiled, but then went pale as he realized the predicament he just put himself into. “Well, there might be a problem.”

“Which is?”

“I think she thinks I’m a girl.”

“Did you tell her the truth?”

“No.”

“Why not?”

“Because she was actually talking to me. If I had said I was a boy in girl’s clothes, she would’ve stopped and thought I was a perv.”

When they arrived back at their room, Chris was relieved to find his suitcase sitting by his bed. 

“Oh, thank God!” he exclaimed, tossing the hat and sunglasses on Amanda’s bed. He picked up the suitcase and plopped it on his bed. He opened it, pulled out his board shorts and ran into the bathroom. He took off Amanda’s clothes and put on his own. He then walked back out, tying his hair back into a man-bun and putting on his own sunglasses. “I’m going to meet Sarah at the pool.”

“Have fun,” Amanda said, folding the clothes he had borrowed. “Good luck!”

He got off the elevator at Deck 11, the pool deck, and walked towards the main pools. He could see her waiting for him. When he got closer, they briefly made eye contact. What Chris realized was that there was no sense of recognition in her expression.

He kept walking. With each step he felt more regret at not being honest with her.

* * *

Days went by as Chris either stayed to himself or hung out with his family. He would occasionally see Sarah walk by with her friends. He wished he could hang out with her.

With the cruise now halfway over, Chris was feeling upset and lonely. His fears about being the only single person on this ship were realized. Sure, there were people his age, but all were coupled up. Some even appeared to be on their honeymoon. That made Chris even more lonely. 

He saw Sarah again from a distance. Her smile was infectious, and he couldn’t help but smile back. 

“Are you having fun?” Dad asked from the pool chair next to him.

“Yeah,” Chris said. “I’m a little bored, though. I wish I had some friends to hang out with.”

“Then go make some,” Dad replied. “It’s a big ship. And we only have a few more days before we go home.”

Chris looked at Sarah and her friends splashing around in the pool. She didn’t even recognize him. He could always introduce himself as a boy, but he was too timid to do so.

He suddenly had a crazy idea.

What if he approached her as what she expected him to look like? That would mean crossdressing again. In front of more strangers. He did it once. He could do it again, right?

What if his parents saw him?

Dad was right, there were only a few more days of vacation. He was tired of feeling sorry for himself.

He silently got up from the pool chair and walked down the three decks to his cabin. Part of him thought that he should ask Amanda for help, but he was too embarrassed to do so. 

When he got into his cabin, he walked over to Amanda’s side of the dresser. He opened her drawers and looked for bathing suits. All Amanda had were two-piece bikinis. He couldn’t do that, could he? Maybe if he wore a T-shirt over it.

He found an orange bikini that Amanda hadn’t worn yet. He quickly tucked his penis and scrotum back and slid the bikini bottom into place. He hoped this would hide his package and it wouldn’t fall out. He’d have to remember to keep his legs closed.

Next was the bikini top. After fiddling with the straps, Chris was able to get it on. Apparently, the bikini was slightly padded and gave the illusion of modest breasts. He stared in the mirror and bunched up his flabby pec muscles into the bikini cups to help that illusion.

He then found the same clothes he borrowed the first day. The T-shirt, shorts, and sarong. He put those on over the bathing suit and looked in the mirror again. He pulled out the hair tie, parted his blonde hair down the center and fluffed it up to look more feminine. Then he found another pair of sunglasses on Amanda’s side of the dresser.

“Here goes nothing!” he thought.

He stepped out of the cabin and briskly walked to the elevator so as not to be seen. He pushed 11 and nervously twiddled his fingers as the elevator ascended to the pool deck.

He walked out of the elevator and towards the outside doors. He paused behind the towel stand and saw Sarah by herself at the pool bar.

“It’s now or never!” he said to build up his courage.

He walked up to the pool bar and sat next to Sarah. “Hi,” he timidly said.

She looked at him with a surprised expression. “Chris, hi! Where have you been?”

“Sorry. I got stuck with family time.” He didn’t want to dwell on his absence, so he followed up with, “What are you drinking?”

“It’s called a Sea Breeze,” she replied. “It’s really good. You should try one.”

Chris chuckled as he saw the bartender give Sarah the familiar red drink. “I had a bad experience with that drink,” he replied. He should’ve told the truth, that that particular drink was responsible for him dressing in his sister's clothes. But he withheld that part of the story.

The bartender then looked at Chris. With an accent Chris didn’t recognize, he asked, “What can I get you, Miss?”

He looked at the bartender in momentary shock. Bartenders were good at reading people. This was working. “Um,” he paused to scan the drink menu, “I’ll have a Blue Hawaiian, please.”

“So how has your cruise been so far?” Sarah inquired.

“It’s good. Relaxing. But I was getting kinda bored spending time with my parents.”

“Well, spend some time with us.”

“I’d love to,” he smiled.

The bartender gave Chris his frozen blue drink. 

“Thank you,” he said, signing the receipt.

“Come to the pool, I’ll introduce you,” Sarah offered.

He followed Sarah to the pool. 

“Hey everyone, this is Chris,” she announced to her friends. 

“Hi,” he said timidly to her friends in the pool. He then looked across the pool deck and saw his parents and Amanda get up from their lounge chairs. It appeared that they were looking for him.

Sarah sat at the edge of the pool dangling her legs, and Chris joined her quickly to get out of view of his family. 

Chris exchanged small talk with Sarah and her friends. Where they were from, what college did they all graduate from

When there was a lull in the conversation, Sarah slid into the pool, then turned around to face Chris. “The water’s great! Come on in.”

This part actually made Chris nervous. He’d have to start shedding some of his feminine costume. He looked around to make sure nobody was looking at him. Sarah was, but he was more worried about his parents. He knew the sarong was covering up his leg hair, so he just needed to get into the water quickly. He stood up and took off the sarong then quickly slid the short jean shorts off. He decided to keep the T-shirt on. “I forgot to apply lotion,” he said as he quickly stepped into the pool and made his way over to Sarah. Hopefully nobody noticed his leg hair.

When Chris looked down, the bright bikini top was perfectly visible underneath the wet T-shirt. Hopefully that meant nobody would mistake him for a boy under these girls' clothes.

Sarah swam to the other side of the pool, where she found a beach ball just floating there idly. “Hey, Chris!” she yelled as she spiked it towards him.

Chris was caught by surprise but managed to volley the ball up into the air where another of Sarah’s friends punched it back to Sarah.

Sarah hit it back to Chris, but the ball came down in front of him, splashing his face. She giggled as he wiped the water off of Amanda’s sunglasses.

He hit it back, just a little short in order to splash her.

Chris was finally having fun. He swam over to the edge of the pool to take a sip of his drink. He turned back around just in time to volley a ball away to one of Sarah’s friends.

He suddenly felt someone tug on his bikini strap through his shirt. He turned around to see Amanda grinning at him.

“Having fun, Christine?” she giggled.

He instantly turned red from embarrassment. “It’s not what it looks like,” he whispered.

“Well, it looks like you’re wearing my clothes again. And my new bikini.”

“I can explain-”

“It’s actually pretty obvious. You’re pretending to be a girl to impress this girl you met. Is she into girls?”

“I… I don’t know.”

“So what are you trying to get out of this?”

“I’m just having fun.”

“Great. Hey, anyway, Mom and Dad said to meet at the pub in an hour.”

“OK, I’ll get ready to leave.”

“OK. Well, be careful, Christine.” And with a wink, Amanda left.

Chris swam back to the center of the pool to join Sarah.

“Was that your sister?” she asked.

“Yes, it was.”

“That’s so cool you’re close with your family. I can’t imagine going on a trip like this with mine.”

“I need to get going,” he said. “Dinner time with the family.”

“Sure. What are you doing after dinner?”

“I have no plans,” he admitted.

“We were thinking of hitting up the night club,” she offered.

“Oh, cool. Maybe I’ll see you there.”

“Cool. See you around, Chris.”

* * *

Chris entered his cabin to find Amanda looking over the cruise schedule. “Hey.”

“Hey.” she responded without looking up. “Did you have fun in the pool?”

“Yes,” he said timidly.

“I’m glad. You looked miserable the past few days.”

“Thank you for letting me borrow all of this. Sarah invited me to the club with her friends after dinner.”

“Do you need my clothes again?”

Chris hadn’t thought that far. “I don’t know.”

“I’ve got a cute top and a skirt if you’re interested.”

“I’ll be fine,” he assured her, not really thinking about the logistics.

“Is she expecting a boy or a girl to show up?”

Chris was silent. He didn’t want to admit he had painted himself into this corner. “A girl, I guess.”

Amanda smiled. “Again, I’ll keep this between us. I’ll see what I have for you.” 

Chris sighed. He was still embarrassed he was even having this conversation with his sister. “Thank you.”

She walked over to the closet and pulled out a black crop top and a white skirt. “I wore this the other night, but I think you can wear it tonight. But, you’re going to need to shave your legs this time.”

“Wait, you told me my leg hair wasn’t visible.”

“That was when you were wearing my clothes for a few minutes. Now you’re going clubbing.”

“Amy!” Chris whined as he turned red with embarrassment.

“You can wear stockings, but I don’t want you putting runs in them. Go ahead and start your shower. I’ll find you a spare razor and my shave gel.”

Chris walked into the bathroom and slammed the door in frustration. He wondered how many people at the pool noticed his leg hair. 

He got out of his clothes and into the shower, and a few minutes later there was a knock at the door.

“It’s me, I’m closing my eyes,” she said. “I left the razor and shaving cream on the sink.” 

“OK,” Chris acknowledged.

When Amanda was out of the bathroom, Chris quickly opened the door and grabbed the razor and shaving cream. He had light hair to begin with, but he had no idea what he was doing. 

He lathered up his leg and slowly started shaving it like he’d do his face. It took a few passes, but before long he got the hang of it.

After the shower, he got dressed into his dinner clothes. Tonight was Hawaiian shirt night, so he wore slacks and a flowery red Hawaiian button down shirt.

His newly shaved legs felt very sensitive under the slacks. He couldn’t take his mind off them.

Amanda placed a stack of clothes on his side of the dresser. “For after dinner. Top, skirt and panties.”

“Panties? Do I have to wear your underwear too? Why can’t I go commando?”

“You are not going commando in my skirt!” she yelled.

“Fine. Wait Up. I can’t wear a skirt.”

“Like you can’t wear short shorts or a sarong or a bikini? Remember, you asked for this.”

“I thought you were gonna give me skinny jeans or something.”

“I wouldn’t have made you shave your legs if I was going to put you in jeans. You want to impress this girl, right?”

He sighed. “Fine.”

“So after dinner, let's both come back here. I’ll give you ten minutes to get dressed and I’ll do your makeup.”

“Makeup?”

“Chris, this is what girls do when they go out for an evening.”

“OK, fine.”

* * *

“Cheers,” Dad said, as their family toasted with their wine glasses.

“Chris, honey, where did you run off to this afternoon?” Mom asked.

“I met some people at the pool,” Chris said truthfully.

“Oh, we didn’t see you there.” Dad said.

“The other pool,” Chris replied, knowing this class of ship had three pools.

“I’m glad you met some people your own age, then.”

“Amy and I are heading to the casino after this. What’s everyone’s plans for this evening?” Mom asked.

“Cigar bar,” Dad said.

“The night club,” Chris timidly replied.

“You’re going to the club?” Mom asked skeptically.

“I was invited by the people I met at the pool.”

“That’s great. I hope you have fun.” 

* * *

Chris managed to get through dinner without talking more about his new friends or how they met. But he kept thinking about Sarah all through dinner.

Per Chris and Amanda’s plan, once dinner was over, Chris skipped coffee and dessert and excused himself to his room.

Chris excitedly walked into his cabin. Just thinking about Sarah made him giddy. There was also something tantalizing about putting on a costume and becoming someone else for an evening.

Thankfully, Amanda gave him a 10 minute head start. He was still so embarrassed that he didn’t want her around as he changed into her clothes.

He took off his dinner attire and stood in the middle of the cabin looking at the clothes Amanda left for him.

He slid the panties up his freshly smooth legs. He felt a tingling feeling in his penis. He ran his hands over his legs again feeling how smooth they were. It was kinda nice. Was this turning him on? He tucked his member back before it got any bigger. He didn’t have time to really enjoy this.

In addition to the top and skirt, Amanda had left him a black sports bra. Chris put it on and pulled the crop top over it. The sports bra provided just enough padding. He turned sideways for the mirror and admired his modest “breasts.”

He then pulled the skirt on. He noticed his legs felt a little cooler in a skirt. Looking in the mirror at himself made him feel a little weird. His smooth legs looked sexy in the skirt.

He then pulled out his man-bun and combed his fingers through his hair like he did earlier.

He looked in the mirror. For the most part, all he saw was a girl. But his face. He wasn’t able to hide behind sunglasses at night.

Chris started pacing his room. People would surely know he’s a guy. Sarah will think he’s a perv. How is he going to hide this? 

There was a knock on the door. 

“Chris, it’s me,” Amanda said. “Are you decent?”

“Yeah, “ Chris said, opening the door for her.

“That outfit looks cute on you.”

Chris cringed, unsure whether she was teasing or complimenting him.

“Sit on your bed,” she said.

Chris did as he was instructed as Amanda retrieved her makeup bag from the bathroom.

“Now hold still.” Amanda applied eye shadow, eye liner and blush to Chris’s face, then finished it off with lipstick. She handed him a tissue. “Blot like this,” she demonstrated.

He followed her instructions.

“All done. Go have a look.”

Chris looked in the mirror amazed. He looked like a girl. “This is all your fault, you know. You spilled that drink on me!”

“Sure, now go have fun.”

He put on his own flip-flops then walked out of the cabin.

* * *

Chris arrived at the nightclub. He didn't see Sarah and her friends yet, so he ordered a vodka tonic then took a seat at the bar and waited for them.

Ten minutes later they arrived. Sarah was sexy in a skin-tight dress that highlighted her curves. When she saw Chris, she smiled and waved. “Chris, I love that outfit. It’s so cute!”

Chris thanked Sarah for the compliment and joined her and her friends as they got a table on the outskirts of the dance floor.

A drink later, Sarah pulled Chris onto the dance floor. Chris was feeling good after those two drinks and just dancing with this cute girl was making him feel great. All Chris’s fears and shyness melted away as Sarah seemed to spend more time with him than her friends. “Surely she’s interested in me, right?” he thought. 

After an hour of dancing, Sarah whispered into Chris’s ear, “Wanna get some air?”

“Sure,” Chris replied.

“I know a nice quiet spot,” Sarah said with a wink.

They walked to the elevators and Sarah pushed 11. They got off at the pool deck. Everything was quiet, so they casually strolled to the port side of the ship and to the railing. 

It was dark out. The moon was high and casting a reflection on the ocean.

Neither said a word. Their hands touched. 

Chris slid his hand into hers and to his surprise she allowed it and squeezed his hand.

Slowly they inched closer.

Chris turned his head and saw Sarah looking at him. The moon reflected off of her eyes. He leaned in and they closed their eyes as their lips met.

Slowly their kisses got more passionate as they started to massage each other’s tongues. It was getting uncomfortable to be standing while leaning against the railing, so Chris shifted his weight to his other foot.

Sarah noticed this. “Do you want to sit?” she suggested, pointing to the deck chairs.

“Sure, “ Chris said, sitting down on one.

To his surprise, Sarah straddled him and he leaned back into the chair.

Chris was turned on. He could feel the swelling in the panties and was afraid his tuck would come undone.

Sarah started to suck on Chris’s neck as he moved his hand to her breasts. He was in ecstasy. This was a perfect ending to this day.

Sarah grabbed Chris’s chest as well, and Chris sucked on her neck for a bit.

He was too turned on and suddenly felt his dick spring free of the panties. “Shit” he thought. He needed to nonchalantly reach over and tuck it back in without Sarah knowing. As he hesitated, he felt it getting harder and harder. There was no way to tuck it back now. 

“Someone is excited,” Sarah whispered. She reached down and started stroking him through the skirt.

Chris had a surprised expression on his face. “She knows?” he thought.

“Don’t be shy, Chris,” she said as she grabbed his hand and removed it from her breast and placed it between her legs.

He felt his hand touch the material of her dress, but what he didn’t expect was to feel something hard underneath.

Her hand on top of his grasped something very familiar. The moment he realized when it was, he recoiled, his hand jerking away.

“What the hell?” he shouted, leaning away from her. “What is that?”

She looked at him with confusion. “What do you think it is? Wait- you… didn’t know?”

“Know what?” he asked, unable to comprehend what was happening.

“I’m transgender.”

“I can’t believe I just touched a dick!” he exclaimed, pushing her to the side as he pried himself off the chair.

“Way to ruin the moment, Chris,” she said, tearing up.

“I’m not gay.”

Sarah shook her head and stood up. “I’m sorry. I-I thought you were trans too. I guess I misjudged you." With that, she bolted for the elevators, tears running down her cheeks.

Chris stood there in shock, unable to process what happened.

* * *

Chris walked to the other side of the ship to use a different elevator and pressed deck 8. He was trying to avoid people so they couldn’t see him crying. Chris quickly walked into his cabin in tears.

Amanda was sitting up in bed reading a book. “Chris! What happened?”

“Sarah is a he. She’s a dude.”

“What?”

“Sarah said she’s transgender.”

“Then she’s a she, right?”

“What? I don’t know. I’m so confused.”

“Did she know you were a guy this entire time?”

“Yes. I think so. She said she thought I was trans too.”

Amanda was silent as she bit her lip. “I’m sorry, Chris. That sucks. You both looked like you were having so much fun at the nightclub.”

“You saw us?”

“I was checking up on my big brother.”

“I just can’t deal with this right now.” He grabbed his sleeping attire and walked into the bathroom. 

Minutes later he came out of the bathroom in a T-shirt and pajama bottoms, then crawled into his bed, silently turning away from his sister.

“Chris?” Amanda asked softly. “Do you want to talk about it?”

He said nothing. He was confused. He had such a great time with Sarah until it ended in disaster. The look of hurt on her face when she ran off also confused him. What did she see in Chris? Did she see a guy or a girl?

* * *

That night Chris tossed and turned. His embarrassment was fresh and raw. Eventually, he fell into a fitful sleep.

He dreamed he was on an excursion with his parents. They stopped into a clothing shop and Mom held up a dress. “Wouldn't you look good in this dress, Chris?”

“Mom, I'm a guy,” Chris whined. But as he said that, he looked down to see he was wearing a bikini and he had real breasts.

“Don’t be silly, Christine.” 

“Hey, Christine,” Amanda said. “Your girlfriend is outside.”

Chris left the shop and found himself outside where Sarah was there waiting for him. Except Sarah was a guy.

Sarah smiled at him which confused Chris. 

Weren't they mad at each other?

“How’s my girlfriend today?” Sarah asked.

Chris felt warm all over being called Sarah’s girlfriend. He forgot why he was mad in the first place.

But Sarah was a guy. Chris didn’t want a boyfriend. He wanted a girlfriend.

Sarah leaned in towards Chris and right before they kissed, Chris woke up.

“I’m not gay,” Chris thought to himself. He was confused by this whole transgender thing. Was Sarah a girl or a guy? Chris thought she was a girl. And he liked her. He thought she was attracted to him as well. Would it hurt to have spent more time with her?

He realized then that he had a hard-on.

He started replaying his intimate moments with Sarah in his mind. As he did he started stroking himself. When he was on the verge of climaxing he realized that he didn’t care what was under her skirt. He realized he fucked up. 

He needed to apologize to Sarah.

* * *

That morning, after breakfast, Chris went straight to the pool and volunteered to hold chairs for his family.

As more and more people came to reserve chairs, eventually he saw Sarah and her friends. He got up to apologize to Sarah, but before he could reach her, one of her guy friends cut Chris off.

“I need to talk to Sarah,” Chris said.

“She doesn’t want to talk to you.”

“Please, it’s important. I want to apologize.”

“You hurt her.”

“I know.”

The friend didn’t budge, and Chris gave up and walked back to his chairs.

For the next few hours, Chris sat there poolside, regretting how he reacted last night. He wished he could take it back. He wished he could roll back time or get a second chance.

He walked up to the bar to order himself a drink.

“Hey!” he heard a sweet voice say beside him.

He turned to see Sarah standing there.

“Hey,” he said, eyes looking down. He couldn’t look her in the eyes after his behavior the night before.

She sat down on a stool.

“I want to apologize,” Chris finally said. “My reaction was totally out of line. I regret some of the words I said.”

“I want to apologize too,” Sarah said. “I came on too strong. I shouldn't have assumed you were trans too.”

“How long did you know I wasn’t a girl?” Chris asked.

“You mean a cis girl?” Sarah corrected. “I clocked you walking to the muster drill with your sister. I stood next to you because I thought you were cute and were just starting your transition. I thought you could use a friend.”

Chris felt embarrassed that she knew the whole time. Time to come out with the truth. “I spilled a Sea Breeze all over my own clothes. My luggage really was missing. I had to borrow my sister’s clothes to go to the drill.”

Sarah giggled. “That was the bad Sea Breeze experience you mentioned?”

“Yeah... but it did get us to meet.”

“Well, that explains why you wore your sister’s clothes at the muster drill. What it doesn’t explain is why did you keep wearing her clothes?”

“I liked you and wanted to hang out with you again. But you didn’t recognize me dressed like a guy.”

“OK, I have a confession. I did recognize you.”

Chris looked at her confused and blinked. “But then why…”

“I was afraid I clocked you wrong. Clearly I did. But then you showed up dressed in girls clothes yesterday. I’m impressed you crossdressed for me. Most cis men wouldn’t be caught dead wearing girl clothes. And you even came out rocking a bikini.”

Chris chuckled. “I still can’t believe I did that. I really wanted to see you again.”

“But that was only because you thought I was a cis girl.” The disappointment was clear on her face.

Chris bit his lip. “I’m sorry I freaked out. The truth is, I’m still enjoying your company. I want to keep hanging out with you."

The bartender came over. He looked at Chris first, but Sarah spoke up.

“We’ll have two Sea Breezes,” she ordered.

Chris looked at her inquisitively.

“Sounds like we could both use a do-over.”

The drinks came back. Chris signed for them, wondering if it was OK to play the gentleman with her.

Sarah picked up her drink. “Hi. I’m Sarah.”

Chris picked up his. “Hi. I’m Chris.”

They clinked their plastic glasses then casually strolled away from the bar.

“What’s it like?” Chris asked.

“What? Being transgender?”

“Yeah.”

“Always wondering how people see you. Whether you’re going to get assaulted in the women’s bathroom. Worrying about if I can get a job after college. Wondering when your family will come around and talk to you again. Wondering if that cute girl you’re flirting with is transphobic.”

“I’m sorry, again.”

“How about you? What was it like crossdressing for a day?”

Chris smiled. “It was weird. But thrilling in a way.”

“That’s how I felt the first time I tried on women’s clothes.”

“I felt sexy last night.”

“You looked sexy last night.”

Chris blushed. “So did you.”

They looked at each other in silence for a long moment.

Finally, Sarah broke the silence. “Hey Chris, what dinner time do you have?”

“8”

“So do we. Hey - we have an open seat at our table. Would you like to join us?”

“I’m not sure if your friends will forgive me so fast.”

“They will. They are just protective of me. I’ll let them know we’re all good.”

“I’ll have to check with my family,” Chris replied. “My mom likes us all to get together at least once a day. But I’d love to have dinner with you.”

“Oh, I understand, Chris,” Sarah replied. 

“Hey, if I’m able to get away, do you want me to come as Chris… or Christine?”

Sarah was taken aback and raised her eyebrow. “Christine?”

“My sister was joking and calling me that.”

“Well, Chris or Christine,” she affirmed, “It’s your choice. I’ll accept whoever shows up.”

* * *

Chis was pacing around his cabin when Amanda walked in. He didn’t know why he even suggested crossdressing again. She told him he didn’t have to. So why did he want to do it anyway? Was it to impress her? Yes. That was it. He’d keep telling himself that.

“I need your help,” he said to his sister.

“With what?” she asked.

“Sarah invited me to dinner.”

“You both made up. That’s great. What can I do?”

Chris was silent. He was afraid to ask. Up until now, his crossdressing was forced upon him by the situation. This time it was his idea. “I need to borrow your clothes again.”

“Oh. I thought you were done pretending.”

“I am. I mean. I’m done lying to her.”

“Is this her idea or yours?”

“Mine.”

“I’ve got an extra dress you can wear.”

“I don’t need a dress.”

“It’s the formal attire night. Yes, you do.”

He sighed. She was right. But he couldn't wear a dress in front of their parents. “What am I going to tell Mom and Dad?”

“The truth. A girl asked you to join her for dinner. They’d be thrilled you made a friend.”

“But Mom is going to want to take formal pictures before dinner. I can’t take pictures in a… dress.”

“I can tell them you’re sick and can’t come down.”

“Thank you.”

“Oh, don't thank me yet. We still need to do your hair and makeup.”

“My hair too?”

“Chris, if you’re going to a formal dinner with this girl you had better look the part.” She handed him the dress on a hanger.

Chris took a shower and came back into the room wearing just shorts.

“I have your clothes picked out,” Amanda said. She tossed the bikini top back at him. “Put this back on. I don’t have a real bra that fits you.”

Chris put the bikini top back on then looked at his sister for the next set of directions.

“Hey, Chris,” she probed. “Is there anything you want to tell me that you don’t want to tell mom and dad?”

“This, obviously.”

“I meant in general.”

“No.”

“Don’t worry about it. Anyway, shoes. You really need heels with that dress. I highly doubt you’ll fit mine, but you should at least try them on.”

* * *

Chris stepped off the elevator to the promenade deck where Sarah said to meet. 

At the steps to the dining room stood Sarah, holding a clutch and smiling at him.

Chris smiled back, grabbed onto the handrail, and ascended the steps towards his date, making sure to take each step carefully in his borrowed two-size-too-small heels.

“Good evening, Christine,” Sarah greeted him with a light kiss to his cheek.

A warm feeling filled Chris up after Sarah greeted him with that name. “Good evening, Sarah,” Chris softly replied. “You look beautiful tonight. I love your dress.”

“Thank you,” she replied. “And you look absolutely stunning.”

“Thanks,” he confessed as he began to blush. “I had a lot of help from my sister.”

“We have twenty minutes to spare, do you want to sit down at the cocktail bar?”

“Sure,” he replied. “Just no Sea Breezes this time. My sister would kill me if I ruined her dress.”

“No problem,” Sarah giggled.

“Hey, where are your friends?” Chris asked, looking around.

“Oh, they said they’d meet us at dinner.”

Chris and Sarah ordered glasses of white wine.

“This is a beautiful ship.” Chris said, trying to make small talk.

“Have you heard they’re making a bigger one?”

“Really? Wow. I can barely find my way around this one.”

Just then, Chris saw his parents and Amanda standing beside them. He and Amanda made eye contact and she quickly tugged at Mom as Chris looked away.

“Wait, Mom. Why don’t we check out the casino?” Amanda suggested.

“I just want to get a drink,” Dad said, walking up beside Chris.

Chris scooted closer to Sarah and tried to keep his head down.

Dad turned to his family. “Want anything?”

“I’ll have a mojito,” Mom answered.

Amanda replied, “I’ll just wait until we get to dinner.”

Sarah turned to Chris. “Is everything OK?”

“Just a little seasickness,” Chris whispered.

“I’ve got some dramamine here in my clutch.”

“I’ll take two mojitos,” Dad said to the bartender.

Chris whispered to Sarah, “Let’s just go to dinner.”

“OK” she replied.

He grabbed both of their glasses and ducked away from his parents. When they got to the dining room, Sarah’s friends were waiting for them.

Chris followed Sarah to her table, which thankfully was on the other side of the dining room from his parents.

Sarah pulled out the chair for Chris. He smiled then sat down, remembering Amanda’s instructions to smooth out the dress. “Thank you.” He’d never been treated like that before and he kind of liked it.

During dinner, Chris and Sarah would make eye contact and they’d smile. A few times, Sarah would wink at Chris. During dessert, she slid her foot up Chris’s leg. It felt electric against the pantyhose Amanda insisted he wear. He returned the favor, and they both smiled at the thought of what the evening had in store for them.

* * *

Chris didn’t make it back to his cabin until early the next morning. He tried to be quiet and not wake his sister, but lost hold of the cabin door allowing it to slam shut.

“Chris, is that you?” Amanda called out groggily. “What time is it?”

“It’s, um, 5 a.m.” He tossed Amanda’s heels into the corner. “Sarah and I went to the late show, then went for a walk on deck.”

“Must’ve been a pretty long walk.”

“Well, we were a little drunk…” Chris said as he unzipped the dress and tossed it aside. He fell down on the bed wearing just the bikini top and panties.

Amanda giggled. “What happened then, Christine?”

“Sarah calls me Christine now too,” Chris admitted. 

“Does she now?”

“We cuddled up on a deck chair under some towels and fell asleep in each other’s arms.”

"Good thing you didn't get caught."

"Uh, actually we did," Chris confessed. "Fortunately, it was a deckhand and not security. He just woke us up and told us to go to our cabin."

Amy reached over and turned the light on. Both of them squinted from the change of brightness.

"Chris, there is makeup all over your face and neck! It seems like you two did more than just make up."

Chris smiled and reminisced on the evening’s activities. He left a lot of details out. Especially what they did after dinner. Those details were definitely NSFSE (Not Suitable for Sister’s Ears). “I’m going to just lay here and pass out.”

“Chris.”

“Yeah?”

“Those are NOT my panties you’re wearing.”

* * *

The rest of the cruise was a blur to Chris. The only thing he remembered from this cruise was that magical night with Sarah.

He and Sarah exchanged contact information and vowed to stay in touch. They lived several states away, but both were adults and could find a reason to travel that distance.

When Chris got home, he quickly unpacked. His roommates were curious how his family cruise went. He evasively told them just the mundane details.

One of his roommates cocked his head. “Chris, you dog, you got laid!”

Chris blushed and checked his phone. “Hey, I need to run upstairs, I need to make a phone call in a bit.”

He closed his bedroom door and locked it. He then pulled up a website to search for women’s clothes for his next meeting with Sarah.

He checked the time on his phone again.  It was time.  He dialed the number.

She picked up on the second ring.  “Hello?” She sounded excited as if she was expecting this call.

That made Chris smile. “Hi Sarah, it’s Christine.”

---

TF Emily (tfes8) writes gender transformation stories.  Her second novel, The Boy Who Would Be Prom Queen can be found on Amazon for both Kindle Unlimited and paperback. Her other novels and a growing collection of short stories can be found on TGStoryTime, FictionMania, and her website tfemily.com.