Vacation Suitcase Mixup

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Kelly's suitcase is missing and he has to wear girl clothes.
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jackie_em
jackie_em
1,565 Followers

Note - This story includes incest as well as cross-dressing and some non-con/reluctance.

Note - if you want a story where a guy is sissified and sexually used by men - this isn't your kind of story.

This is for the Summer Lovin contest. If you like it, please vote.

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I'm Kelly an 18 year old guy just graduated from high school. My parents said as a graduation present, they were sending me on a nice summer vacation. I love the mountains and hiking and swimming and really looked forward to this. I was supposed to go with my 21 year old cousin Brad, but at the last minute something came up and he couldn't go.

I was perfectly happy going by myself, but the family didn't want to waste the money they'd laid out for the trip, so everyone except me, agreed I'd go with my 19 year old female cousin Nikki. Okay, Nikki is cute, but she's my cousin and a girl. From my point of view that really stunk, but none of the rest of the family cared.

They managed to get the airline ticket transferred from Brad to Nikki so it was decided that was how it would be. We got to the airport and Nikki had two black rolling bags, and I had one identical bag. They told Nikki she couldn't take both of her bags without paying an outrageous fee. Nikki fussed with the bags and sent one home with her parents and we checked two bags.

I know, I could do a lot worse than spending two weeks in the mountains with a cute girl, but she was my cousin, for crying out loud. The flight went smoothly, though Nikki wanted to talk to me the whole time. I politely listened though I zoned out half way through it. We landed and got our two checked bags and went out to where the bus was to take up to the cabins.

It had been raining hard and though the rain had stopped, everything was a real mess. On the way to the bus, Nikki stopped abruptly and I tripped over her and fell, right into a muddy patch of ground. I was a mess and now needed to change clothes. Beyond that, there was now a huge rip in the seat of my jeans. The bus had a restroom and I took my bag and went there to change.

I pulled off my ruined clothes and cleaned and dried myself as best I could with paper towels, then opened the suitcase to get something else. What I saw when I opened it was Nikki's clothes. She was seated near the restroom so I cracked the door and tried to get her attention. It took a minute or so, but she heard me and came over.

"What's the matter, Kelly?"

"I have your bag and you have mine."

"Okay, we can switch. Hold on."

She went back and got the other bag. In the meantime, I closed that bag and kept the restroom door shut, to keep anyone else out. Very quickly she came back and gave me the other bag and I gave her the one I had. It was a little tough since the restroom was small and I didn't want the rest of the bus to see me in my all together. I opened the other bag and it had girl's clothes too.

"Nikki, where the hell are my clothes?"

"Aren't those yours?"

"No, both bags have your stuff in them."

"It must have gotten screwed up at the airport, when we had to send a bag back."

"What the hell am I supposed to do?"

"You can't go naked, and you can't wear those jeans."

"What else do I have to wear?"

"Wear some of my clothes. We're about the same size."

"Fuck, no."

"You got any better ideas?"

We were about the same size, and apart from being wet and muddy, the way my jeans were ripped, I couldn't wear them. The bus was already on the road, so even if that small airport had jeans in my size, it was behind us. There was no way the bus would stop on the way just for me to get clothes, and I wasn't sure what I could wear into a store anyhow.

I was stuck, and could either wear Nikki's clothes or go naked or nearly so. I began to go through the suitcase looking for a pair of jeans. Sure they would be women's jeans but unless someone looked at how they zipped, no one would know. All I saw was skirts and tops, along with bras and panties. How the hell was I supposed to wear that shit?

"Nikki, do you have any jeans in the other bag?"

"No, just skirts and tops, underwear, and a couple of bikinis."

"I can't wear a fucking skirt."

"You can't go naked."

"I am so fucked."

"You should be so lucky."

"Fine. I'll find a skirt and top."

"Don't forget panties, and you really should wear a bra too."

"I'm not wearing a bra."

"In a skirt and top, and with the length of your hair, you're going to look exactly like a girl, and I girl has to wear a bra."

"But I'm not a girl."

"Only you and I will know that. Anyone else who sees you will figure you are."

"Shit, shit, shit."

"Just shut up and put some clothes on, girl."

"I'll girl you."

"Promise?"

I was screwed. Until or unless I could get something better, I'd be wearing Nikki's skirts and such. I looked for the most bland panties and bra I could find. Of course, Nikki being a very girly girl had all frilly undergarments. The best I could do was a pair of lacy light blue panties and matching bra. Her skirts went from short to borderline obscene, so I got the longest I could find, and a subdued top.

The jeans were no good now, so I just put them in the trash. I wanted to wash out my boxers and tee, but had no place for them to dry. I grabbed some socks to fill out the bra, though I wasn't quite sure why. I closed the suitcase and went to sit with Nikki. She immediately began to brush my hair, which was longish. Then she opened her purse and began to put makeup on my face.

"Do you have to do that?"

"A girl has to look her best."

"But I'm not -- "

Nikki put a finger to my lips as a guy walked back to the restroom.. He stopped by us and smiled, and of course Nikki smiled back. I sat frozen in my seat, half afraid he'd realize I was really a boy and half afraid he'd think I was truly a girl. I wasn't sure which was worse. I looked at the floor kind of hoping he'd go away, but of course he had to talk.

"Nice to see a couple of cute girls on this trip."

"I'm Nikki and this is my cousin Kelly."

"Nice to meet you both. I'm Tom and I'm traveling with my friend Rob."

"I'm pleased to meet you, Tom."

"Maybe Rob and I can get together with you two girls for some fun when we get there."

"I'd love that, but Kelly here is in a bad mood."

"Rob and I will do our best to cheer her up."

"See you later then."

"You can bet on it."

Tom went back to the restroom and I sat there, utterly appalled at it all. Nikki resumed doing my makeup as I sat there stunned and trying to figure out some way -- any way -- out of this mess. Very shortly Tom came out of the bathroom and smiled at us again as he passed and returned to his seat. I could see him talking to his friend and the two of them looking back at us.

"I'm not going to go do something with some guy who thinks I'm a girl."

"It's not like you have to fuck him. You can if you want though."

"No, I don't want."

"Tom seemed particularly taken with you, but Rob looks cute too."

"I don't want either of them."

"You've got to let loose and have some fun."

"That's not the kind of fun I want."

"Party pooper."

"It's bad enough I have to dress like this. Now you're putting makeup on me and trying to set up a double date for us with two guys."

"When we get there, we need to shave your legs and underarms."

"Fuck, no."

"Fuck yeah. If you're going to look like a girl, you need to be properly groomed."

"I'm not dressing this way because I want to."

"You're still dressing this way."

"Only until I can find better clothes."

"I checked. There's no shops there. I'm not sure where you're going to find something better."

"I have to spend two fucking weeks dressed as a girl."

"Yep, but the fucking is optional."

"There's no chance of that."

"You might like it."

"You can fuck them both -- just leave me out of it."

"We're in this together, Kelly."

Nikki was sitting by the window, while I was on the aisle. I asked her to switch seats with me and she agreed. I was very glad of that a little later when Tom and Rob decided to move to the two empty seats across from us so they could 'chat up the two cute girls they met'. Nikki flirted with them while I largely stared out the window and avoided looking at or talking to them.

"Your cousin doesn't seem very friendly."

"I think she's still upset because her boyfriend dumped her."

My face turned almost purple, or at least that is how it felt. I took a couple of seconds to get back under control before I turned to them and spoke sweetly. "You're so silly. You know it was my lesbian lover who dumped me."

That silenced everyone briefly and I turned back to the window, ignoring them again. That brought down the intensity of the conversation. After a little while Tom and Rob returned to their original seats. Nikki sat quietly by me for a while before getting up and going to the restroom. She came back and sat near Tom and Rob to chat for a while before coming back to sit by me again.

"Kelly, you are such a bitch."

"I'm a bitch? You're the one who was getting such great fun out of dressing me up like this."

"It wouldn't have killed you to play along."

"They weren't playing. They were hoping to get laid."

"Not every guy who wants to get laid gets that."

"So you can sleep with either one or both."

"We have two weeks at this place. Are you going to spend the whole damn time hiding in our cabin?"

"Better than having a couple of guys trying to play grab ass with me."

"You're such a shit."

After that, Nikki sort of pouted and I tried to ignore her. She went up to talk with Tom and Rob a couple of times. I suppose I could have gone back to the restroom and washed off the makeup, but honestly, it never even occurred to me. I began to wonder how in hell both of Nikki's suitcases came, while mine got left behind, then I remembered she'd been messing with the suitcases at check-in. Did Nikki do this to me deliberately? I knew she had a weird sense of humor, but that would be pushing the boundary.

.................................................................................

We finally arrived at our destination, which was a rustic resort with log cabins. Nikki and I went to check in and I got another shock. Brad and I had booked a two bedroom cabin, but somehow things got switched and Nikki and I were now in a one bedroom place, mercifully with two beds. Nikki seemed happy with that, but I wasn't.

"We booked a cabin with two bedrooms."

"Sorry, but that got assigned to someone else."

"Well assign it back."

"We can't do that, miss."

'Miss', shit so now these people think I'm a girl too. What can I expect, the way I'm dressed? And since I didn't get around to washing it off, I was still in the makeup that Nikki put on me. Unless I could score some jeans, I was pretty much stuck this way.

"You have other cabins, get us another two bedroom place."

"All of our two bedroom cabins are occupied."

"This is unacceptable."

"Miss Kelly, we're sorry, but to apologize, we've comped your food for your stay here."

"So my cousin and I have to share a bedroom."

"You're two girls. What's the problem?"

Shit, I'm standing there in a skirt, top, bra, panties, and makeup. I'm supposed to tell them I'm really a boy? This is just so fucked, but what can I do? They have a mess hall where they provide food to many of the people, but no stores. Particularly no clothing shops. I'd really been hoping that I could get out of Nikki's clothes, but no dice. After arguing to no avail, I went to the cabin I was to share with Nikki.

"So I guess my second suitcase is now your suitcase."

"Just what I wanted." Of course I was being sarcastic, since it was not at all what I wanted.

"But we can swap clothes too."

"Like that makes it better."

"We can have so much fun dressing you up."

"You mean you'll have fun. I just want boy clothes and some privacy."

"Two girls can share a bedroom, but we can't have a boy and girl share one."

"But I am a boy."

"Nobody else thinks so."

"Just totally fucked."

"Since you say you're a boy, don't you want to see a girl in skimpy clothes?"

"You're not a girl, you're my cousin."

"I may be your cousin, but believe me I am a girl."

"Doesn't do me any good."

"A nerdy little virgin like you wouldn't know what to do with a girl anyhow."

"What makes you think I'm a virgin?"

"If you weren't, when I said that, you would have told me who you fucked."

She had me there, and the sad thing was that she was right. I was a virgin, mostly because girls didn't seem interested in s scrawny nerd, and because I was a bit shy. Still, there's nothing like having it thrown in your face. I had kind of hoped that coming here with Brad, that he might help me get laid. Now, sharing a place with Nikki, there was no chance of that.

I took a shower, since I was still a touch messy from the mud puddle earlier, plus I wanted to wash off the makeup. With my clothes off, or rather with Nikki's clothes off, I felt like a boy again. Okay, I might be nerdy and not in any way muscular, but still I could see and touch my boy parts. After my shower, Nikki insisted that I shave my underarms and my legs.

"I don't need to do that. I'm not really a girl."

"You're dressed like it, so you need to look decent."

"I'd rather be indecent."

"Tom could help you with that later."

"Hell, no."

"And as long as you're dressed this way, you're going to wear makeup."

So my legs and underarms were shaved. I had shaved my face, though the few scraggly hairs there were hardly visible. Nikki got me an outfit, rather sexier than before and insisted that I wear it. As though to add insult to injury, Nikki painted my toenails and fingernails. Once I was done to her satisfaction, she said we could both go out.

It was dinner time and Nikki and I went to the mess hall. Of course before that, she had to touch up my makeup and such. It was basically cafeteria style, so we went through the line and got some food and sat down. Of course we were quickly joined by Tom and Rob. Rob was clearly interested in Nikki and she seemed similarly interested in him.

Tom kept trying to flirt and chat with me, though I wanted no part of that. There was an announcement that there would be music and dancing in the social hall after dinner. I wanted no part of dancing, though Nikki, Rob, and Tom all were interested, and wanted me to join them. I just wanted to hide in the cabin for as much of the two weeks as possible, but somehow got dragged to the social hall.

I didn't want to dance -- I certainly didn't want to dance with a guy. In spite of my protests, I found myself on the dance floor with Tom. I suppose for fast dances, it wasn't too bad. I could largely ignore who I was dancing with and how I was dressed. Of course that couldn't last and a slow number came on, and before I could escape Tom had his arms wrapped around me.

He held me close and he started with running his hand up and down my back. Before long, he had his hand all over my ass. I tried squirming away, but he held me far too tight for that. I could feel his hard cock pressed against me as he nibbled on my earlobe and felt up my ass. When the song was over he gave me a kiss, which I refused to respond to. Finally, I managed to get free of his grasp.

"I really want to spend time with you and get to know you better, Kelly."

"I'm not into guys. I like girls."

"Why don't you give me a chance to change your mind?"

"I don't want my mind changed. I know what I like."

"I know how to make you feel good."

"You have no idea what makes me feel good."

"Maybe you could show me, and maybe make me feel good too."

I managed to get away from him and went back to my cabin and threw myself on the bed, shaking from fear, disgust, and I'm not sure what else. I wanted a fun, carefree, relaxing vacation, but instead I was in drag and had a guy pawing me and wanting probably to fuck me, though if he knew what I had between my legs, he might have changed his mind. What scared me was the thought that he might not care.

Once I felt back under control, I washed the makeup off again. I wished I could take off the nail polish but I wasn't sure how to. I took off the top, bra, and skirt, and found a long tee to wear as a nightshirt. I kept the panties on. I needed something over those parts, particularly since I was sharing a room with Nikki. I tried keeping the shirt covering the panties, just to give me some modesty.

It was some time later when Nikki returned to the cabin. She was giddy and seemed to be intoxicated. She took off her skirt and top right in front of me. It shocked me, since I am a guy, even if she has me dressed like a girl. She was in her bra and panties as she came over and got on hands and knees on my bed facing me.

"You should have hung around. Rob smuggled some vodka in and shared it with me."

"I don't need to get drunk, and neither do you."

"Don't be such a snot."

"What else did Rob do, once he got you drunk?"

"We had some real fun then, and you missed all the fun."

"Fun? Right. Tom would have tried to get me drunk and get me to suck his dick, if nothing else."

"I did that for Rob. You should do that. Every girl needs to be able to suck her guy's dick."

"No fucking way."

Nikki crawled up and got right in my face. "If you weren't such a prude, you'd love it."

I was angry as shit. "You know what I'd love? I'll show you what I'd love."

I don't know if I caught her by surprise or if it was what she really wanted, but I flipped her on her back on my bed. I ripped her panties off her, spread her legs, pulled down my panties and stuck my cock in her pussy. She was wet down there and my dick slid in very easily. I couldn't believe how wonderful it felt having my prick in Nikki.

Nikki laid there with her eyes open just staring at me. I began to move my hips back and forth. Sure it was my cousin, but I was fucking a girl, even if it wasn't what she wanted. I know I don't have the biggest cock in the world. It's maybe six inches when it's hard and it's downright tiny when it's soft. Right now, each of those six inches was reveling in Nikki's cunt.

I fucked her slowly. I was afraid that if I did it too fast that I'd cum too soon and I wanted this to last as long as it could. I could feel myself nearing orgasm and just stopped with my dick in her and leaned forward and kissed her as my prick calmed down a bit. I was surprised to find Nikki kissing me back, though there was a funny taste in her mouth -- Rob's cum, as I later realized.

When I felt more under control, I began to pound her again. Nikki closed her eyes and moaned as I plumbed the depths of her being. I stopped a couple more times, to stretch it out, until I felt her cunt grab my dick. Nikki was moaning and seemed to be in another world, as I fucked her until I came in her pussy. I kind of zoned out as I came.

As I returned to consciousness I began to frantically kiss Nikki and even played with her boobs through her bra. We kissed until my wang slipped out of her, at which point I rolled off her to lie beside her on the bed. All the humiliations of spending much of the day looking like a girl were washed away by the pleasure of actually having sex with a girl.

"You shouldn't have done that."

"I couldn't help myself, and besides, you seemed to enjoy it."

"I mean you shouldn't have cum inside me."

"Why?"

"I can't use the pill, it messes up my hormones and throws everything off."

"So you're not on anything?"

"No, so I could get pregnant. That's why I didn't let Rob fuck me."

"I'm sorry, but that felt so damned good."

"It felt good to me too. I'm just concerned."

"You mean you don't want your girl cousin to get you knocked up?"

jackie_em
jackie_em
1,565 Followers