I'm a freshman in college and since we've moved in, I've had the biggest crush ever on the girl across the hall, Gabby. We've become good friends, we get lots of meals together, watch movies, and even go out to bars together. There's just one problem ... she gets taken home by a different guy every time we go out. I'm practically in love with her but I can't say a word because I couldn't stand to ruin our friendship. And I know she's not interested because her type is big black guys, usually on the football team, and while I'm a decently buff guy I'm pale as can be and I'm the same height as Gabby: five foot six.
I've told all our mutual friends about my crush, usually when I get too drunk, and I think she's caught on because our hangouts have gotten more and more awkward recently. But, like I said, we still hang out all the time and have a great time together.
And then came the fateful day that Gabby told me she was planning a spring break vacation for us and she expects me to come. She's rich as can be and has her own place off campus, and she tells me her parents have paid for her to fly us out to some tropical island for a week. It was going to be just the two of us and she says the trip is her treat. I'm over the moon! Is this finally my chance to tell her how I feel? Could I have been totally wrong about her not liking me?
Gabby texts me all week about the trip. She sends me a packing list. It's oddly light. Just sunglasses and some other essentials but she's very clear that I shouldn't bring any clothes. I ask her why not but she assures me we will have everything we need at the resort and if need be she'll sponsor a shopping spree. It feels like forever but finally, the time comes to leave school for the airport. I pack a single carryon with just the stuff on the list and I'm ready to go. I carry my and Gabby's bags down to her car and she drives us to the airport. Oddly, she packed much more heavily than me but I guess girls tend to do that so I don't think anything of it.
On the plane, Gabby is a little flirty but also nervous. I'm worried she's getting cold feet about the trip. "Are you sure your parents are okay with this?" I ask her.
"They're paying for it, silly. I'm just a bit worried about what you'll think about where we're going," she answers.
"Well, we're friends. If you have a fun time, I'm sure I will too." She has been oddly secretive about our final destination, but I just want to make sure she's not going to change her mind. Gabby seems pleased with my answer.
Once we land, I'm awed by the scenery. Gabby had described this island as a remote paradise and she wasn't wrong. She leads me to a private jet which takes us to a tiny island off the coast. As the plane approaches, I see the most amazing resort.
When we land, I follow Gabby off the plane and she greets the man who meets us at the bottom of the steps. He's tall, black, and muscular. His arms look like he can lift the plane we just stepped off of. He's wearing a bright yellow speedo and I'm already jealous of him. He has a massive bulge in the front. He greets Gabby like an old friend and calls her "princess" which strikes me as odd but I figure it's some kind of pet name.
"Princess, is this the boy you told us about?"
"Yeah, this is Holden," Gabby answers, introducing me. I feel small next to this big man, he's got to be at least a foot taller than me. He reaches out and shakes my hand and I swear my arm feels like he's crushing it. I'm trying not to let on, though, and I put on a brave face.
"You must be the Holly, I'm glad you're joining us."
I don't know what he means but before I can respond, Gabby speaks up.
"Yep, this is Holly," she says. "Now, can you please show us to our room so we can change?"
"Yes, princess, right this way."
He leads us to a golf cart and takes us into the resort. It's absolutely gorgeous and the grounds are meticulously maintained. We pass dozens of muscular, mostly shirtless black men along the way. The women we pass are stunning. Some are tall and fit with massive breasts, others are short and petite with a curvy ass, and many are somewhere in between. Every single one of the women are wearing nothing but the same white thong bikini and black heels that must be six inches tall. I'd thought the black men were the resort staff but maybe it's these women?
The big man leading us drives past the main resort building and around to a path hidden by tall trees. This area is less populated and as we turn a corner, the most amazing bungalow appears before me. The outside walls are a white stucco and the roof is red clay. It looks like a little house you'd see on the Mediterranean coast.
"This is where you'll be staying, princess," the man says.
"Thank you, Marcus, we'll be fine from here."
Marcus turns the golf cart and leaves, driving back the way he came.
"Come on, Holden," Gabby says, leading me up to the front door of the bungalow. She unlocks the door and inside it's even more gorgeous than the exterior. There's a massive bed with a beautiful wooden headboard and white linen sheets. The rest of the room is open and airy and there are two doors leading out to a large balcony overlooking the ocean.
"Wow," I say, looking around the room. "Your parents really pulled out all the stops for this trip."
"Yep!" Gabby answers excitedly. "And now that we're here, we can get started. First things first, take off all your clothes."
"What?"
"Oh, come on. We're going to go to the pool and we can't have you wearing clothes." I got a little excited for a second but that makes more sense.
"Go on," she says, encouraging me.
I start stripping, taking off my shoes and socks first. I can feel her eyes on me as I remove my shirt and pants. When I'm down to my underwear, I look up and see her smiling.
"Everything," she says.
"Um ... okay," I say.
I hook my thumbs under the waistband of my boxer briefs and push them down, exposing myself to Gabby. My penis is semi hard and I'm hoping she doesn't notice.
"Ooh, I like your dick," Gabby says. "I'm not surprised you've been hiding it all this time."
"Thanks," I say awkwardly, I can feel my cheeks getting red.
"Now, we have a special surprise for you."
"A surprise?" I ask, a bit worried.
"Yep. Close your eyes and hold out your hands."
I comply and a few moments later I feel something soft being placed in my hands.
"Open your eyes!" Gabby commands.
I open my eyes and see the same string bikini the women on the staff were wearing, and at my feet, she's placed the black stilettos.
"What is this?" I ask.
"Put it on."
"What?" I'm confused and worried that she's pranking me.
"Trust me, it's part of the surprise."
"I'm not sure ..."
"Just put it on, Holden," she says, getting a bit frustrated.
I give in and put the top on, then the bottoms. My dick doesn't exactly fit but I kind of tuck it under. I put on the shoes. The heels are a struggle but I get them on and am amazed at how much taller I look. I have a nice view of Gabby from this height. I try to ignore the weird feeling of wearing the bikini.
"Wow," Gabby says, walking in a circle around me. "You're actually a pretty girl. Okay, close your eyes again."
"Um, okay," I say, closing my eyes.
I hear Gabby digging through her luggage and a moment later she puts something cool and metallic on my neck which I assume is a necklace. All of a sudden I get the weirdest stomach ache and double over for a second and cry out but before I know it the sensation is gone.
"Okay, you can look now."
I open my eyes and immediately notice I'm now shorter than Gabby, even with the heels on. I walk into the bathroom, also noticing my gait feels weird, oddly natural in the heels. Then I see my reflection. Standing before me is a beautiful woman. The necklace has some kind of medallion hanging from it and I lift it to see a heart-shaped pendant with the name "Holly" inscribed on it. My new body is probably eighty pounds and definitely under five feet tall. I'm as pale as I've always been and I now have platinum blonde hair too. I've filled out the cups of the bikini nicely, they barely hold my perky new breasts. Then I look down and see what I feared: my bulge is gone.
"Do you like it?" Gabby asks.
"I ... um ... how did this happen?" Oh! My voice is so high!
"This necklace has magic. You are of course free to take it off at any time, but I want you to wear it for the whole trip. Do you like your new name, Holly?"
"I'm not sure, actually," I say.
"Well, it's not up for debate," Gabby responds.
"Okay," I say.
"Good. Now, we're going to have a lot of fun, trust me. I've got a few surprises planned. Let's get out there! Oh, and there's one thing you should know, if a man's semen gets inside you this is permanent. Taking the necklace off after that won't change anything. Just try to keep yourself protected. Now, let's get going!"
I follow Gabby back outside. She locks the door to the bungalow and takes me to a nearby path.
"We're headed to the beach. The guys are all so happy to see the new girls," Gabby explains.
"So, what are the men doing here?"
"The resort is for them, silly. The girls you see in uniform are the staff here. The guys are guests. They all come here to unwind and let loose and the girls are here to keep them happy. I'm sure you'll like it, everyone has a great time."
"Okay," I say. "Wait does that mean I'm one of the girls on the staff? Are you too? Why aren't we wearing the same white uniform?"
"Well, I'm just a guest but you're gonna be a working girl. Don't worry, thanks to the necklace it should all come pretty naturally. I know I'm not a guest but Marcus is a good friend and he let me tag along."
"Why did you bring me here, Gabby? If I'm going to be a sex worker or whatever, why didn't you bring one of the other girls?"
"You're my best friend, Holly, and I thought you deserved a real spring break. Trust me, once we get to the beach, you're gonna have the time of your life. And by the way, call me Princess."
"Oh, okay. Thanks, I guess."
"Don't mention it," she says. "Oh, and if any of the guys tell you to do something, just do it. It's easier that way."
"Okay, sounds good."
We continue down the path and soon emerge on a beautiful, wide sandy beach. Dozens of muscular black men are sitting at the water's edge. There are a few women in white bikinis serving them drinks. As we walk by, the men all check us out. Most of them look a little surprised. I guess the bikini is a little tight. I find I kind of like the stares.
"Hi, boys," Gabby says. "Have fun."
Gabby heads toward the bar and the men are eyeing me like a piece of meat. One of them, a massive specimen of a man who must be six and a half feet tall, waves me over.
"Hey, you. Come sit with me."
"Go!" Gabby tells me.
I head over to him and take a seat next to him.
"Hi, sweetie," he says. "What's your name?"
"Um, I'm Holly."
"Nice to meet you, Holly. My name is Malik. Do you know why you're here?"
"Gabby, um, Princess told me that the resort is for the men and the women are the staff."
"That's right, baby. We come here to relax and we're treated to all kinds of hot women to keep us happy. And you're going to make me happy, right?"
"Of course," I say.
"Good. You're so cute and I just can't wait to get inside you."
"Inside me? What are you talking about?"
"Well, sweetie, this must be your first day of work! The uniform you're wearing means you're one of the resort's pleasure girls so you get to take care of my sexual needs. That's what the white-clad girls are here for: to satisfy the men."
"Oh, okay. Sure."
"Good, let's get started. You're gonna give me a blowjob. Get down there and take it out."
He's sitting on the sand and his massive black cock is clearly visible through his bright green swimsuit. It's gotta be ten inches and thicker than my wrist. I get down on my knees and move between his legs.
"Take it out, sweetie."
"Yes, sir," I say.
I pull the waistband of his swimsuit away and his huge black dick flops out. It's even bigger than it looked through the fabric.
"Now suck it, whore," he says, a little bit of a sneer in his voice.
"I've never done this before," I say.
"Just suck it," he says, putting his hands on the back of my head.
"Okay."
He pushes me down onto his cock and I wrap my lips around it. It's warm and the skin is smooth. I try to remember everything I've seen in porn or read in smut about sucking dick. I run my tongue over the tip and use my lips to apply pressure. I try to go deeper and take him in as far as I can.
"Damn, slut. You're good at this. Your mouth is so soft."
I try to deep-throat him and choke a bit. He doesn't let up though and keeps pushing me down onto him. I'm trying to breathe but I'm getting lightheaded. Nonetheless, he does fit shockingly easily down my throat. I suppose my new body is made for this purpose.
"Yeah, that's it, suck my dick."
I'm doing everything I can to make him happy. I find myself getting really horny as I keep blowing him. His hands are still on the back of my head and I can't pull off of him, but I don't think I want to. My tongue is pressed against his shaft and his tip is hitting the back of my throat. I'm running out of breath.
"Get ready, slut, you're gonna swallow every drop."
A few seconds later he thrusts his hips and his cock twitches in my throat. Hot semen starts to pump into my belly and his dick keeps twitching. I'm swallowing as quickly as I can. When he's done cumming he lets me off his cock and I'm gasping for air.
"Good job, whore. I can't wait for round two."
"Round two?" I ask.
"Oh, yes. We're gonna have a lot of fun today. Now, go help serve the others."
I get up and start walking back to the bar towards Gabby, not entirely sure what to do.
"Hey, Holly," one of the white-clad girls calls out. "Come here."
"Yeah?" I ask.
"Princess told me that you're new so I'll give you the rundown. First, always have condoms available. The guys here usually like to fuck raw but the owner requires us to use them when the guys ask. It's in the rules and I've gotten punished for failing to enforce that. Second, when a guy wants you, give him what he wants. The more satisfied they are, the happier we are. Finally, you're gonna wanna take care of a couple of the regulars. They tip big and if you do a good job with them they'll be sure to spread the word."
"Okay," I say, "thanks for the info."
"Don't mention it. Oh, and the condoms are in the bar, go help yourself."
I turn and go inside the bar, seeing Gabby on a stool chatting with a few of the other women.
"Hey, Holly, did you enjoy your first taste of black cock?" Gabby asks.
"Yeah," I say, blushing.
"It's fun, isn't it?"
"Yeah."
"Here, have a drink," one of the girls offers.
"Thank you."
"Of course," the girl says.
The woman behind the bar slides me a tall glass of iced tea with lemon.
"Wow, thanks," I say, "hopefully this gets rid of the cum taste in my mouth." I actually like it but I don't want Gabby to know.
"Wait, please tell me you didn't swallow his cum, Holly!" Gabby starts freaking out. "That's it. Take the necklace off. It's too late. You're Holly now. Forever."
"Shit, really? Fuck I thought you meant like it would be permanent if I got impregnated or whatever. What the fuck?!" I start to break down in tears.
"Yep. I'm sorry. You'll have to be a pleasure girl forever now."
"What? How is that fair? Why does semen have to have magical properties?"
"Because that's how it works."