Femboy Vacation Sex

I lay face-down on the beach towel in my bikini, taking a moment to adjust my boyhood. I lay there for a while, tanning my round, girly booty. I hear people walk by. I hear a pair of guys older than me stop walking behind me.

"Damn, girl!" one says. "That is the finest ass I ever seen!" Keeping my face down, I poke the bottle of lotion with my foot. The guy gets the message and says something like "hell yeah!" and grabs it. He and his quiet friend sit in the sand next to me. I hear him squeezing some lotion out onto his hand. He begins spreading it on my back and rubbing it in.

"Dude," he says, "this girl is so fuckin' soft, I swear."
"Bruh," says his quiet friend who I now can tell is black, "look at this bitch's body. God damn, I would tap this shit all night." He gets some of the lotion and rubs my back while the white guy rubs my legs. The black guy has such strong hands. I have had this raging boner for like ten minutes.

The white guy tending to my "soft as hell" (his words!) legs starts creeping higher and higher, testing the waters. I wiggle my ass seductively, inviting him to please please touch it.
"It must be my birthday, look at this shit, she wants it," he says.
"Make sure I get a turn," says the black guy. They both laugh. Suddenly one of them gives my ass a smack, and it goes POP. I think it was the black guy. I want them both to fuck me so bad, but I can tell they're straight.

The white guy gets some fresh lotion and lowers his hands onto my soft, round ass. He rubs in circles at first and then just starts squeezing and playing with it. I cannot accurately describe how fucking turned on I am. He keeps going "Damn...damn..." I am in ass-heaven. He ran out of lotion a while ago but keeps rubbing and squeezing.

Eventually, they decide it's the black guy's turn. He smacks it again, harder. "Dayum!" he says. "You see her ass vibrate? I ain't never seen a white girl with a booty like that..."
He starts rubbing my ass ferociously, slapping it occasionally. At one point he leans down and kisses my asscheek, followed by a lick.

When he's done, they sit down next to my head. The white guy feels my neck and shoulders. "Ya know, I like girls with this haircut. Where it's all short, like this?" He rubs my head and the black guy agrees.
"Come on girl, what's yo name?" the black guy asks. I make up a name.

"Heather," I squeak out. They introduce themselves, so I must have a convincingly high voice. I stifle a giggle. Never thought that would work.
So anyway, the white guy is named Preston and the black one is named Damon. Finally, I gain enough confidence to sit up and look at them. I'm wearing sunglasses so they see as little of my face as possible. I'm also wearing some red lipstick. Other than that, I have soft, feminine features in general so hopefully they buy it. I sit with my knees pulled up to my chest so they won't notice my lack of boobs.

They continue talking so I guess they don't notice anything unusual about me. I halfway listen and enjoy the wind lightly blowing my hair. I loooove my hair lately, I've got this Anne Hathaway thing going on, it's so sexy.
"But like I said earlier," Preston says, "I've been here for a month and I never seen a girl as cute as you." I smile at him and he turns away, grinning bashfully. Now that I look at him, I'd say he's about 19. Handsome.
Damon starts talking again so I get a better look at him. He's probably about as old as Preston, except Damon is fucking sexy. I want him to ruin my--

"Do you wanna?" Damon interrupts my thoughts. Do I wanna what? I can't pay attention well when I'm horny. I nod and smile at him, which prompts both of them to stand up. Preston offers a hand to help me up. I take it. "Such a gentleman," I say with a sexy little smile.

I pick up my things, which consists of a towel, a bottle of lotion, a change of clothes, and some white booty shorts. I briefly consider putting the shorts on to hide my cock, but they'll be looking at my ass anyway. I hold my stuff so that the towel falls down my front, hiding my flat chest and my cock. I step into my flip flops and follow them away from the beach and into the street. Me and some sexy boys, walking along the sidewalk. I don't usually wear girly things in public, but I like the looks I'm getting. "So Heather, you from around here or what?" asks Preston. I realize I need a story of some kind.

"No, actually, I'm just here on vacation. Staying with a friend of mine," I say. Which isn't a total lie.
"So, do you always let random guys on the beach feel your ass?" Preston asks. I giggle, which makes him smile.
"No, I guess I was feeling..."
"Spontaneous?"

"Horny." He looks at me and I give him a very sexy look. Damon laughs.
"I love me some white girls," Damon says. They lead me to their hotel, which is nice. But going inside means I have to take off the sunglasses and hope they don't notice anything. Luckily, my eyelashes are done up, so hopefully that'll be enough.
"Nice place," I say.

"Yeah, and it's pretty close to that nude beach," Preston says. Damon puts his arm around me and I feel very warm.

"Maybe we should go there," Damon says. I nod, but that would be a bad idea for obvious reasons. We get to their hotel room, and they throw their stuff down on the floor. I go to the bathroom almost immediately. I hear them saying something about how they're going to get laid tonight, but I just start getting into my clothes that I brought in. I put on the bra and slide in the little gel inserts that make it look like I have boobs. I pull on the white tank top over it and step into the booty shorts. I look at myself in the mirror. Damn, I look sexy. I step outside and give the boys a smile.

They can't keep their eyes off of me! I sit down on the bed in a girly little way and pretend to be preoccupied with my phone so they can get a good look at my smooth legs and whatever else without fear that I'll catch them. We chat for a bit until Damon announces that he has to go to work. Had I been paying attention earlier, I would have known that he was down here working for his uncle and Preston was a friend of his who tagged along. So now me and Preston are alone in this hotel room, sitting kind of close together on the edge of the bed.

"You have beautiful eyes," he says suddenly. I look up, a little surprised. "I didn't wanna say that in front of Damon, but they're gorgeous. So big. Like you can see right through me."
"Well, that doesn't sound like something you'd say," I reply, blushing a bit.
"You barely know me."
"I've known you long enough that you've touched my butt."
"And? I act differently around Damon, I really want you to know that. I come off as a douche sometimes."
"True." He laughs at this.

"But I think I really like you, Heather. You're different from other girls." Very true.
"Thanks..."
"You're not just pretty. You're funny, and charismatic, and--"
"And I have a great ass." He laughs again.

"That's what I mean." I look at him, like I really look at him, and I can tell he's being sincere. A second ago I honestly thought he was just trying to get into my pants, but now I really wanna kiss him.
"I really wanna kiss you," I say bluntly. He looks into my eyes and at my lips and he does! I feel so warm and I swear there's fireworks going off in my head and I put my hands on his face and his lips are so soft but then we come up for air, laughing breathy laughs and smiling, just smiling. I kiss him again and he puts his hand on my thigh.

So basically we make out for like ten minutes.

Somehow we've ended up lying on the bed on our sides, staring into each other's eyes and occasionally continuing the kiss. It gets frisky again, but this time he fondles my boobs through my shirt and bra, which gives me another erection. The boob insert things must feel real to him if he can just play with them. I pull away just to be safe. We stare at each other again. I bite my bottom lip, which I'm told is really cute when I'm wearing lipstick. It seems to work on him, because he just grins and kisses me again. We lay there for a while before I get up to take a piss.

"Your ass looks amazing in those shorts, babe," he says. I do a little dance for him and close the bathroom door. I sit down to piss just in case. When I'm done, I admire my ass in the mirror for a moment before opening the door.

And when I do, Preston is on his bed, naked.

"Oh," I say, blushing, "hello there." He grins. My lord, his cock looks delicious. I'm not sure how long, but... above average, for sure. Jesus.
"Why don't you come over here, baby?" he says. And goddammit, I really want to. But what happens if he finds out I'm a boy? If it were Damon, I might get my ass beat (in the bad way) but Preston seems different now. Like I can trust him. But then, what if he feels like he was lied to? What if I hurt him? He senses my hesitation and sits up, looking ashamed.

"I'm sorry, I just thought maybe... I don't want to make you uncomfortable, that is the absolute last thing I--" I shut him up by shoving his cock in my mouth. What am I doing? "Damn..." he says, "you're fucking good at..." He just lets the sentence die. I'm pretty good at sucking cock, in my opinion. And clearly Preston's. I gaze up into his eyes and I can tell it's having the desired effect. That's what's great about wearing this red lipstick, when I suck cock it looks so sexy. I'm doing pretty well, and he's responding wonderfully. He likes it when I suck on his balls and jack him off simultaneously. He plays with my hair.

After a surprising amount of time, he announces that he's gonna cum, but I don't stop. I use my tongue to massage his length until I can tell somehow that he's coming close. I take him out of my mouth and open wide, aiming his cock at my face. His warm seed goes into my mouth at first, but most of it ends up on my face and in my hair. I scoop some from my cheek into my mouth and swallow it. Obviously the taste isn't great, but I'm so horny I couldn't care less.

"You're quite a sight right now," he says through a grin. "That was seriously the best blowjob I've ever gotten."
"I take pride in what I do," I say coyly. He laughs and I realize that he probably can't fuck me now that I made him cum so much. Disaster averted, I guess. He starts to put his clothes on while I look at myself in the mirror. I love having cum on my face, it just makes me look like such a little cumslut. Suddenly we both hear the door being unlocked. I start getting panicked. Clearly it's Damon, but what is he going to say when I have Preston's jizz all over me?

As the door opens, Preston finishes pulling his shirt on and I have my back to the door, scooping cum into my mouth.
"Hey guys, job got cancelled on account of rain," announces Damon. I turn around and Preston gives me a look, as if to say, "what are you doing? Hide your messy face!" When he sees my lack of his fluids on me, he looks relieved. When Damon goes into the bathroom, I flash Preston a smile. He almost laughs, because his pearly white spunk is all over my teeth. When Damon walks out, I swallow it.

"So what did you guys do?" Damon asks. I look at Preston.
"Oh, you know," I say, "debauchery." Preston gives me another grin. Damon stares at me. "What?" I say. "Something in my teeth?" Preston covers his mouth, giggles almost escaping.
"Actually, it's your hair," Damon says. Oh shit. He gets a closer look. "Is that..." he starts to say. He laughs and shakes his head at me. "You a wild one, little white girl." He turns the TV on and starts watching. That was a close one.

The rest of that day was fun. The rain got a lot worse (I later heard it was a tropical storm) so we stayed inside and goofed off. Damon showed us how to get free stuff from the hotel vending machines. Preston convinced me to "nose" everyone in the indoor pool (touch them with your nose without them noticing) and we almost got kicked out because Damon kept singing songs about my butt. At one point, we ran into some folks in the hallway who Damon asked, "What do you think, sir? Is this a fine booty?" I showed them my booty. We all agreed, it was a wonderful booty. We hung out in the hotel room and played the board games that were in the drawers. I won at Scrabble. Preston and Damon threw the Monopoly money all about the room and we rolled around in it.

Damon conducted a "scientific experiment" to find out if my butt made an efficient pillow. It did. At around midnight, the boys played video games while I watched from under the covers. I normally enjoy video games, but I was shitty at the ones they brought and I was tired anyway. When everyone got tired, we decided to push the beds together so that I could sleep in the middle.

"Just a warning, I own a rape whistle," I say while I climb under the covers. We laugh at my joke, but I seriously don't want to be touched while I'm asleep. They don't seem bent on doing anything, so I try not to worry about it. I get to sleep, but then I wake up at four in the morning for no reason and decide to go to the bathroom. After I'm finished, I look at myself in the mirror and fix my hair a little. I still look pretty good. When I walk out of the bathroom, I notice a small thump! next to me, the sound of something small hitting the floor. It's Damon's phone. He must have had it while he was... why would he have his phone with him if he's sleeping?

Being the nosy little thing I am, I pick the iPhone up and take it back into the bathroom for privacy. He has several apps for taking different kinds of pictures, so it occurs to me to check his gallery. And just as suspected, the thumbnails appear to be of me. I open each picture. One is of me, sleeping on my stomach, my butt in the air. Some are of my face up close but it's clear that he didn't touch me at least... Most of them are of my butt. Damon is weird about my butt. Wait, no he isn't... of course he'd be attracted to me, I've teased him all this time... I feel guilty.

I open his camera app and point the camera at the mirror. I slide my pants and underwear off and take a picture of my naked ass, careful to hide my penis. When I'm done, I title the picture "Now let me sleep" and save it. I put the phone back where I found it and start crawling into bed. I suddenly notice that Preston is gone.

I climb back into bed, figuring he’d gone to get some food or something. I take advantage of his absence to adopt his side of the bed as my own. I stretch out, adjust my boobs, and try to get some sleep. I’m pretty comfortable, but I’m a bit horny from my earlier escapades in the bathroom. I try not to think about the huge black cock lying next to me. My throbbing boyhood gets the better of me, so I decide to sneak into the bathroom for a quick session of “me time.” I climb over Damon instead of going around (for fun), but as I’m over him, he grabs my ass and stops me.

“Come here, baby,” he says. I don’t object, so he pulls be to him. He shoves his tongue in my mouth and fondles my ass roughly. Getting a tad uncomfortable, but it’s driving my cock wild. I moan into his mouth, and I feel his cock begin to get harder on my thigh. I can already tell that it’s huge.

“Fuck me, please,” I say, my hormones taking over. This won’t end well.

“Don’t have no condoms, baby,” he says, fondling harder. “You on the pill?”

“No...”

“Damn. I want it too, girl, but I can’t get you pregnant. I just want a quick fuck.”

“Want to fuck my ass?” There’s a poignant pause, and I bite my lip in anticipation. He seems to like this idea, because his finger goes in my asshole. I shiver. He reaches down beside the bed and gets some lotion from his bag. It’s probably lotion for the beach, but I don’t question it.

The next bit is a blur.

We’re rolling around and prodding fingers and clothes come off and I feel his (huge) cock and he’s feeling my ass and we roll around until he’s on top, and about to enter me doggy style.

“Your ass is so fucking big,” he says as I try to hide my penis. I tuck it so that it’s flat against me, pointing toward my head, restrained by my top. I am wearing no panties.

He’s poking his cock at my hole, and I’m suddenly wondering if he’s too big for me. It’s definitely not my first time, but my ass is still pretty tight. He plays with my butt cheeks some more as he spreads my hole and begins to enter me. I don’t feel much at first, but once he gets a few inches in, I begin to notice how wide it is. My breath comes in short gasps. He bends over me and grabs my fake tits, massaging them as he forces more and more of his big black cock into my tight white booty. It starts to ache, but I’m so damn horny that I couldn’t care less.

Finally, I feel his thighs pressed up against my soft, pillowy butt. I took his entire cock in my ass. I can barely believe it. He begins to pull out, then back in, out, in, and it starts to burn a bit. I work with his thrusts and try to make it pleasurable for him, but I’m mostly just trying to keep my legs from failing beneath me. Damon gets taken over by whatever demon my ass uses to possess its victims and fucks me hard and fast, his thighs popping against my juicy booty. My cock falls free of the little bind and swings about wildly, hard as a rock. I feel a familiar rippling sensation going across my ass cheeks and legs. I moan like an animal as he ravages my asshole.

“Oh shit, Damon, I’m gonna cum,” I shout over the pleasure.

“Do it, cum for me, baby,” he moans in response. That’s all it takes, and I’m spraying cum on the bed, not caring if he notices. I suddenly feel him thrust into me more slowly as a warmth fills my insides. He came in my ass.

“Oh fuck, that was amazing,” I say, hiding my cock under a blanket. Damon is already back under the covers, ready to sleep. I climb next to him. He spoons me as we fall asleep.

To be continued?