The Birthday Boys

There are always members of Mike, Paul and John's extended family I could think about. Mike has an insanely hot aunt somewhere, but to my knowledge she is married and even I think that I might be a hard sell. Mike does have an older sister, and his Mom is single, but I can't seem to locate either of them. So instead, I resign myself to having sex with one of the girls I already know are interested in fucking me.

"Tom, happy birthday! Please, sit right here," Rachel says as she pats the seat next to her, her and some of the other theatre kids are sitting on some couches on Mike's porch.

I sit down next to her and look around at all the other theatre kids; these are supposed to be my people. I am an actor and so are they of course but... these people are just annoying most of the time. Normally I wouldn't be caught dead consorting with them outside of rehearsals or class. Desperate times call for desperate measures however and I know these people love me because of my talent as an actor.

Rachel is beautiful, it's hard to deny, a small petite thing with olive colored skin, a cute set of duck lips, a strong nose and a pair of a protruding eyes. Any guy would be lucky to lose their virginity to her, you can just tell that she'll be wildfire in bed.

That doesn't change the fact that I had other ideas in mind for my virginity, and if I hadn't agreed to lose it tonight, I'd probably have found something else to do. Instead, I find myself just adding one or two words every now and then into a conversation I have no interest in, knowing that no matter what I do, Rachel, who is running her hand up and down my leg, will have sex with me no matter what.

"I'm going to get a couple of drinks," Rachel says to me with a big grin on her face. "What do you want?"

This pulls me out of deep thought, and when I finally realise what she said, I see this as my chance for a brief escape. "No please," I say as I stand up. "I'll go get the drinks, what do you want?" I ask, already making my way back into the house.

"Vodka Raspberry!" she shouts as I enter the house and beeline for the bar.

"What'll it be?" the bartender says to me as I lean against the bar.

"Honestly," I say as I look out at the party. "Make me whatever you want, just make sure it takes a long time to make," I say.

"Long night?" the girl asks me as she gets to work on a complicated drink.

I turn and look at her, taking her in. The first thing I notice is her eyes, which look similar to Rachel's, strikingly similar as a matter of fact, like they could be sisters. Unlike Rachel however, her skin is pale and her features are soft and less angular. She has a less pronounced nose, a softer chin and a smaller pair of lips. Not to mention the expression on her face reads bored and disinterested as opposed to Rachel's constant expression of excitement.

"You see that girl over there," I say as I point out Rachel, who is laughing along with her friends.

"You mean the girl who's too loud for her size?" she asks.

I nod. "I'm supposed to have sex with her tonight," I explain.

The bartender takes a longer look at Rachel. "So why do you look like you want to kill yourself? I mean, I know why I look like I want to kill myself, and that's because I moved to this town with dreams of stardom and now I'm wearing a pink bow-tie serving drinks to eighteen year old's."

"You're an actress?" I ask, shifting my body toward her completely.

"I'm an actor," she says, correcting me. "Trying to be anyway."

"Me too," I respond as she finishes making my drink and places it down in front of me.

"I can see that," she says as she looks me over. "Young, handsome, good body... are you talented?"

"I nabbed the lead in the school play three years running," I say as if that's supposed to mean something.

"Four years in a row for me," she says and then steps back, showing herself off as if to say 'and I ended up here'. But all I can think about is how the tight white shirt they're made to wear shows off the size of her tits really well, and not to mention those tight jeans...this woman has an incredible body.

"Yeah but, that was in the small town in the middle of nowhere you came from," I explain as I take the drink and sip it. "You sure make a mean cocktail, but who's to say you're really that good of an actor?"

She would be insulted if it wasn't so obvious I'm flirting with her; she's old enough to be working as a bartender and jaded about her career in the entertainment industry, so she is perfect for my fantasy virginity taker.

"You're funny," she says, looking me over. "But trust me, I'm good," she says.

I lean in a little closer still. "Then maybe you could give me some pointers?" I suggest quietly.

"Maybe I could, but I'm at work," she responds, clearly interested in what I'm putting out there.

"First of all, this is my party, so you work for me... second of all... do you really care about this job when I happen to know that there's an unattended hot tub upstairs?" I respond, putting it all out on the line.

The girl stares at me, clearly weighing her options before leaning back and smiling at me. "Lead the way," she says.

I do exactly that, and when everyone is distracted from the cake cutting, she abandons her job at the bar and quickly joins me at the foot of the stairs, where I lead her up and take her down the hall to the master bedroom. "In here," I say quietly as I open the door softly and let her inside, closing it behind us.

She looks around the room, it's giant, when Mike's Dad got divorced, he really went all out. "Wow," she says as she looks up at the ceiling which has mirrors on it.

I take her out to the balcony and turn the hot tub on. "It might take a little bit for the water to heat up," I say as I unbutton my shirt and slowly remove it. She watches me, clearly curious about what kind of body I have.

"Looks like I'm heating up already," she says, fanning herself as my toned chest and abs are revealed.

I remove my slacks and shoes next before climbing into the hot tub, wearing nothing but my underwear. "The water is perfect," I say as I watch her, wanting to see her strip too.

"If you say so," she says as she removed her bow tie and then unbuttons her white shirt, pulling it off and giving me a view of her white bra holding her sizable tits up. They're nothing huge but definitely a handful.

My cock is now rock hard in the water, threatening to poke a hole in my underwear as I continue to watch her strip. Her smooth legs are revealed when she removes her jeans and shoes. Her panties cover her ass which looks god damn incredible and her waist... she looks perfect.

"Mmm..." she says as she slides into the tub opposite me. The water is nice.

"Yeah," I say as I slide next to her and wrap my arm around her shoulder. "Especially now that you're in here with me," I say as I lean in for a kiss.

She brings a finger to my lips, stopping me from kissing her. "If it's all the same to you," she says as she places a hand on my underwear and yanks it down, letting my seven-inch, cut cock free from its confinement. "I'm not really the kissing type."

"Kiss me, don't kiss me, if you're gonna work my cock like that I don't care what you do," I respond as she strokes my dick underwater.

"I had a feeling you wouldn't mind," she says with a laugh as she jerks me off harder, looking into my eyes with a slight pout in her lips. "You got a nice dick, dude," she says.

"Yeah, well, you got some nice tits," I say as I grab her bra and pull it down, letting her nice tits pop out so that I can fondle them.

"My ass is better," she says as she uses two hands to jerk my cock.

"I'm more interested in that mouth," I say. "Do you suck?"

The girl laughs and dives underwater. "Holy fuck," I let out as I feel her lips around my cock, wondering how long she's gonna be able to hold her breath.

"I got a hot tub right out-" Phil says as he has his arm draped over a woman's shoulders, leading her out here, but he stops when he sees me in the hot tub, seemingly alone.

I look over at them, shocked at having been caught, but even more shocked at the woman that Phil was with. "Tom?" Phil asks.

The girl takes the length of my cock in her mouth in this moment, deep-throating me underwater, stopping me from responding to him with anything but a grunt. Her bra floats up to the surface and Phil notices it and realises what's going on.

"You didn't see us," Phil says as he gestures to himself and the woman he's with. "And we didn't see you," he continues.

I just nod as they both leave and not a moment too soon as the girl comes up for air. "Do I suck or what?" she asks, oblivious to the whole thing.

"Yeah, you fucking suck hard," I laugh as she sit myself up on the side of the tub so that my cock is now out of the water and aiming at her face.

She licks my cock from tip to base as I think about what I'd just seen. Mike's dad has just walked up here with Paul's mom, presumably to do a version of what I'm doing right now with this bartender. "Oh fuck," I let out as she licks my balls, kissing them as she grabs my cock and jerks it into her face. I can't let myself get distracted any longer, that would be a problem for another time.

The girl stands up and slides down her underwear, letting it float in the water along with her bra. "You got a pretty nice dick by the way," she says as she straddles me.

"You weren't wrong about this ass," I say as I grab her perfect ass and squeeze it as I push my cock into her soaking pussy.

"Mmm..." she lets out, moaning as I use my grip in her ass to push my cock into her.

"Oh god..." I let out, no longer a virgin, and with my fantasy fuck, too... an older woman.

"Yeah, you like this?" she asks as she wraps her arms around my back tight and bucks her hips, her tits pressing against me, and we're doing everything in our power not to kiss.

"Yeah, I fucking like this, your pussy feels good," I exclaim, trying not to reveal that this is my first time, but I'd be lying if I didn't say that I could already feel I'm close to cumming.

"I might lose my job if I don't get back down there," she says as she rides me harder, pushing me down so I'm on my back on the tiled floor of the balcony. "So, I'm gonna need to use your cock to make me cum quick, that'll be your first lesson."

"Yes mam," I say, my hands not leaving her ass, even as she takes complete control of the situation.

"I like it when you call me mam," she says as puts her hands on my chest.

"I'll call you whatever you want... how do I... stop from cumming... mam?" I ask her honestly, knowing I am incredibly close already.

"You'll get better the more you do it, just..." she scrunches up her face and moves her hips a little differently. "Yes, there it is... there it is..." she continues. "That's right... I'm close..."

"You're close?" I ask, shocked, feeling the pressure building within myself.

"Yes! Yes! Yes!" she exclaims, even though I feel a little like a human dildo I can't help but be excited at the fact that I'm making this woman cum this quick.

"Yes!" she exclaims as she cums on me, her hands digging into my chest. "You can cum," she says.

And not a second too soon because before she can even get those words out my cock is exploding, shooting a full load right into her pussy. "Oh my... fucking... yes..." I let out as I shoot a second pump and the two of us start to relax.

"Oh my... fucking god..." I let out as she grins and slides herself off me, sitting herself on the side.

"So how does it feel to not be a virgin?" she asks me as she fishes her underwear from the hot tub.

"You know?" I ask as I sit up and watch her.

"You think I'm an idiot?" She laughs, standing up grabbing a towel that's hanging over one of the deckchairs, drying herself off.

"It feels damn good," I say.

"I'm glad, you're my first virgin," she says as she drops the towel and starts putting her clothes back on.

"Can I see you again?" I ask, knowing I already sound a little desperate.

She laughs a little. "Maybe we'll see each other on set one day," she says, confirming that this would be a one-time thing.

"Right," I say as she finishes putting her clothes on and makes for the door. "Hey," I say. "What's your name? I'm Tom."

She looks back at me. "Casey."

*** PAUL ***

I have no idea why I agreed to this bet, after all I am the least likely person to be able to lose his virginity tonight. Why? I'm short, skinny, I wear glasses and I am the biggest nerd at the party. And Mike's nerd sister Alex is at this party so that's saying something, because she is a huge nerd! There is not a single person in this town that is as nerdy as me, I know that for a fact, so why in the world would I be able to lose my virginity tonight?

I am sure once I get to college things will get easier, I've already been talking to some of my future classmates, it's a school full of absolute nerds so I know I'm going to be very comfortable. But in this town, there are about exactly two girls who could be classified as being as nerdy as me. There's Mike's sister Alex, who is already a freshman in college about to go onto her sophomore year at the same college as me, so I'm sure we'll be seeing a lot of each other. Then there's Devi who is probably the most annoying woman I've ever had the displeasure of interacting with; luckily for me she managed to get into a slightly more prestigious school on the other side of the country, so after tonight I'll never have to interact with her again.

There is another quote unquote group of nerdy girls at this party, Sarika, Heather and Grace. But they are not true nerds, they're actually kind of popular, popular enough that I notice Mike is chatting up all three of them. Even though Mike isn't as cool as Tom and John by any means, his Dad's immense wealth and his laissez-faire attitude toward parenting score him a lot of points in social circles. Besides, I don't think you can consider yourself a nerd unless you've watched at least one anime and judging from the conversation I tried to start with Sarika a few months ago, she does not fit the criteria.

Despite the fact that I agreed to lose my virginity tonight, I had no idea what I was thinking or how I actually planned to achieve this as I am in no position to get such a thing done.

"Paul," John says, approaching me as I sip my drink by the pool.

He is shirtless of course and has just stepped out of it the water, walking toward me with purpose. John is ripped and has always been a show-off, in fact I've always found it very hard to believe the guy is a virgin like the rest of us, I happen to know that women throw themselves at him. "How's it going man?" he asks me.

"I have managed to go the whole night without having a single conversation with a girl," I respond, thinking about how I'd spent the evening wandering from spot to lean to spot to lean. "So, business as usual."

"I know what you mean," John says, he seems disappointed himself, but how?

"As if you're having trouble," I say to him.

"Um... what do you mean?" he asks, taking a sip from what looks like a glass of water.

"There's no way you're having trouble with girls, I mean, look at you!" I exclaim, and it's true, the guy is over a foot taller than me, staring dead ahead I would be talking to his chest, instead I have to crane my neck up.

"Paul, man," he says as he sips his water. "The entire time you've known me, you ever seen me talk to a girl?"

I open my mouth to speak but then I think about what he's saying, it's true, I have never seen him interact with a girl before aside from our teachers and parents before.

"The only girl at this party I've ever talked to that ain't one of our Moms is Mike's sister," he says as he gestures toward Alex who is over by the kitchen, talking to someone who I can't quite see.

"Shit," I say as I sip my drink. "I had no idea."

John laughs. "It's all good, but we really gotta get this job done," he says. "I have a feeling that Mike and Tom might already have done it, I can't find them anywhere."

I feel a strange sense of superiority over John in this moment, which is quickly followed by a strong sense of shame. "Why don't we just start with something familiar then, and build our confidence?" I suggest, gesturing toward Alex.

"Neither of us is fucking Mike's sister," John says sternly. "That's against the code."

"I'm thinking maybe we can tell her our issue, she's always been pretty cool, maybe she can get us into a group with some other girls and help us out," I say, my imagination running wild.

John shrugs. "Worth a shot."

The two of us approach Alex, not nearly as nervous as if we were approaching other girls at this party. "Hey," John says to her, tapping her on the shoulder. "How's it going?"

Alex turns and looks at us, a smile appearing on her face. "Hey guys," she says as she brings me into a hug, her huge tits pressed against my chest. "Enjoying your birthday?"

I am about to respond when I see Devi over Alex's shoulder. Devi is the most annoying girl in the world. "Oh," I say as I pull out of the hug. "It's you."

She glares at me, the feeling of distaste has always been mutual. "Paul," she says to me.

Alex laughs as she brings John into a hug. "You mean PB and J?" she says, referring to John and myself. "Oh yeah, you'd have been in the same class, right?"

"Right," I say, unable to hide my dislike of Devi.

"Alex," John says. "We were wondering... umm... actually can I talk to you about something?"

Alex nods and walks away with John, leaving me to make conversation with Devi.

"So, you got into Harvard," I say to her. "It's such a shame I won't have to deal with you up at Northern U."

"It's a shame that you'll have no one to show you up," she says with a smirk.

Despite the fact that I hate her, it's undeniable that she's attractive. In fact, as I look her up and down, she's actually incredibly hot, especially the way she's dressed right now. A floral printed, low-cut blouse is tucked into her ripped denim jeans. She even has her bra straps showing and her cleavage is insane. I never thought of her as having sex appeal, probably because I've never seen her out of class.

"You'll probably get to Harvard and realise you just got lucky all these years," I explain to her. "Though I guess they'll probably treat you nice if you're gonna dress like that."

"Oh?" she says. "You like the way I dress?"

I have been caught, I am too surprised to hide how hot I suddenly find her. Somehow, I never noticed how perfect her brown skin is, or how the shape of her lips look designed for a cock, and is that a nose ring in her perfect button nose? How had I never noticed any of this about her before. Her eyes have an innocent look and her hair is long, black, and full of volume.

"You two," Alex says before I can come up with a snappy come back. "We're heading down to the basement to play a game of truth or dare, you coming?"

I look at John who is standing next to Alex. "Just the four of us?" I ask.

Alex laughs. "Tessa's coming and-"

"Wait if Tessa's coming then that means-" I start.

"Well, well, well, hey dorks," my sister says as she, Tessa and two guys who are in the year above us approach.

"Dalia," I say. "I'm surprised you made it."

My sister Dalia, queen bitch, the one person on this planet I despise more than Devi. "Wouldn't miss it for the world bro," she says as she leads the charge, directing us all downstairs to the basement.

"Sorry," John whispers to me. "I had no idea that those were the girls she invited."

Before long, the eight of us are all seated down in the basement with Tessa, Dailia, and the two guys they brought, Nathan and Brad, all sharing the couch. Tessa and Dalia are sitting in the middle together while the two guys are sitting on either side of them. Alex is sitting on an old recliner while John is sitting on the other, newer recliner. Devi and I have been relegated to the floor, we're even at the bottom of the social hierarchy in this environment.