Cocktales

by The Cocky Collective

  I tell Sam I'll think about it, then give him the blow job of his life to soften the blow. Pun intended.

  Sam is perfect. He's rich, virile, smart, and beautiful. He's a doctor. Well, a dentist, but it still counts. He's thirty-five with the stamina of a twenty-five-year-old, and he's an all-around gold medalist in fucking. My ass, my mouth, my pussy—hell, he even makes sure I come while fucking my tits.

  And he's in love with me.

  The problem is, Greg's in love with me too. Greg is twenty-four and a bartender at a family friendly chain restaurant. You're judging me, aren't you? But Greg is hung. Like, urban legend hung. I honestly didn't think it was possible for a white guy to pass the eight-inch mark. It is. He does.

  That fucker hurts—in the best possible way. I get wet just thinking about it…the way the first few thrusts hurt every time—and did I mention his girth? Yum.

  I took pictures once, with his cock buried inside me. I made him lean back so I could snap a picture of my pussy stretched around him. I shudder a bit when I look at it…my skin pulled so taut, it looks like it should tear. Then I masturbate with an average sized dildo. I love Greg's penis, and they make Greg sized dildos, but who’s capable of impaling themselves on that? A cock that big needs to be forced into me while I pant and sweat and scream a little. No way I could inflict it on myself.

  I know what you're thinking. Do I have a picture of Greg's erect cock next to a soda can for reference and can you see it?

  Of course I do. I'd share, but I'm a bitch. Plus, I don't have your email, and you know I can't post that shit on Facebook. Fucking Zuckerberg. "Someone reported your photo for displaying nudity." It's like a breeding ground for tattletales.

  I bet Eduardo would have voted to let us post penis pictures. Too bad Zuck kicked him out. That reminds me, I need to call my best friend and thank her for lending me her stylist for the wedding last weekend.

  The wedding. I'd suspected Sam was growing a vagina while witnessing his friends commit to a lifetime of monogamy. I'd suspected, but I'd buried those suspicions under a few gin & tonics and focused on planting the idea of a threesome in Sam's head. With Greg to be clear. What the possible fuck would be in it for me if Sam and I had a threesome with another woman? Splitting one penis between two vaginas? I don't think so.

  So, I'd gotten Sam a bit drunk at the reception and asked him if he'd ever experimented in college. He'd looked at me strangely, said no, and then fucked me missionary.

  My work was cut out for me.

  Three

  I pull up to The Ivy and hand my car off to the valet. I'm meeting my bestie Darlene for a two-hour lunch on a weekday.

  Do you hate me yet?

  I'm rich too, you might as well know. I've done nothing to earn it either. My father is an aging gay pop star. You know the one. Did you feel sorry for me when I was born? Did you read the spread in People magazine, a picture of my fifty-year-old father cradling me on the cover, and wonder what kind of life I'd have? Did you go to one of his concerts and nudge your date and mutter, "He'll be sixty-eight by the time his daughter graduates from high school!"

  Or were you more concerned I was being raised by a gay man? Did you post something bitchy on Facebook about a little girl needing a mother? You weren't alone. Lots of people passed judgement and made nasty comments.

  Guess what? If you have enough money, the court of public opinion doesn't matter.

  Thanks to money, a fifty-year-old gay man can give the middle finger to the world, buy an egg, hire a surrogate, and nine months later, be blessed with the miracle of me.

  My childhood was fan-fucking-tastic, in case you're wondering.

  I was, and still am, the apple of Daddy's eye. Imagine being raised by someone who thought every silly finger painting you did was artistic genius worthy of museum-quality framing. Someone who showed up to watch every dance class and sat front row during your recitals, then greeted you after with a bouquet more appropriate of a Broadway performance.

  You know those machines indulgent California parents rent so their privileged offspring can experience snow? I never got one. When I mentioned wanting to see snow as Daddy tucked me in with a bedtime story, he'd have the private jet fueled, and an hour later, we’d be Vail bound. I'd slept on the plane and woke to a winter wonderland.

  Any maternal needs I had were covered by my nanny, Martha. I had the same one my entire life, and she was always there for me when I needed a female shoulder to cry on or help with girl stuff. She's retired now, since I don't need a nanny at my age, obviously, but she's still on payroll, just in case, and she's at every holiday, just like family.

  So, my childhood might not have been what society thought it should be, but it was perfect.

  As an adult, I live on a healthy trust allowance, but I'm not a total deadbeat. I do work, designing purses. By designing, I mean I draw an occasional sketch and select materials while a team of people run the company with my name on the door. People may think I have it easy, but it's a lot of work building a brand. A lot. It doesn't happen overnight. In fact, I've been working hard at this for eighteen months. Eighteen! Then, just last week, the child of a washed-up actress launched her own line of handbags. Puh-lease. Everyone knows I'm the celebrity child handbag designer, and she's riding my coattails. She can try, but she won't succeed. People buy the handbags because of me—because they want to be me. I asked my lawyer to send her a cease and desist. She can design a line of sneakers if she wants. The handbag market is mine.

  In addition to working four to eight hours a week, I maintain a vigorous beauty and exercise routine. You've got to be red carpet ready in Los Angeles at all times. Just last month, I escorted Daddy to the Grammy's where he was honored with a lifetime achievement award.

  I'm blessed.

  I'm a bit of golden girl on the celebrity child circuit. Twenty-five years old, and I haven’t had a single arrest or stint in rehab. Plus, the handbag thing. Maybe I'm not doing the grunt work there, but I tell everyone I am, and life is all about perception.

  I'm practically perfect in every way.

  I stride into The Ivy, and the hostess leads me to a table where my best friend is already waiting. Darlene is the daughter of a supermodel and an Oscar-winning Hollywood director.

  She lost her virginity at fifteen to the twenty-nine-year-old leading man of her father’s latest film.

  I cried for a week. It was the first time she'd gotten something before me, and it was offensive to my soul. It had taken me a week to work out a solution. After I dried my tears, I fucked her father. Oh, don't look at me like that. Her parents had long since been divorced, and I never told her how I lost my hymen. I'm not a monster.

  "Hey, doll," I greet as I settle into the chair being held for me by the Maître d’. "Sorry I'm late.

  "No worries, Jenny," she replies. She means it too. She really is that sweet.

  "Tragic news," I sigh after we place drink orders and put our menus aside.

  "What's wrong? Is your Dad okay?" Darlene's perfect brow wrinkles in concern.

  "Dad's as fit as ever. It's Sam. He wants us to be exclusive."

  "That's wonderful!" Darlene beams. She just got engaged to an entertainment lawyer. I'm sure visions of sugar plums and joint wedding planning excursions are dancing in her head.

  "I'm not ready to give up Greg."

  "There is no future in Greg. Sam is a catch."

  I shrug. "I like them both."

  Darlene groans. "You can't have everything, Jenny."

  The waitress places our drinks on the table as I ponder Darlene's words. Why can't I have it all? I deserve it all.

  "Why can't I have them both? I want them both."

  "Both?" Darlene raises her eyebrows in disbelief.

  "Yes." I'm firm. "Sam is the smartest, most successful man I've ever dated. He's the perfect date for public events.”

  "And Greg?" she prods.

  "Greg's just…" I sigh. "Greg makes me feel like I'm the smartest, most successfu
l person he's ever dated."

  "Because you are the smartest, most successful person he's ever dated," Darlene points out with a shake of her head. "So, you're proposing you continue to date them both indefinitely?"

  "Together."

  "Together?"

  "Yes, together."

  "You want a relationship with the three of you?" She looks dubious. I'm surprised. She's normally very supportive of my goals.

  "Sure. Why not?" I ask.

  "Sam and Greg aren't gay, for starters."

  "No, no," I interrupt. "I don't want them to fuck each other. I want them both fucking me."

  "Oh," Darlene responds, finally getting it. "At the same time?"

  I nod.

  She looks skeptical again.

  "Well, good luck with that," she says, then raises her glass to toast.

  I laugh and clink my glass against hers.

  Four

  The following week, Greg arrives at my door with a six-pack of beer and a hard on. We take the beers outside and open a couple while watching the sunset.

  Greg tells me about his lunch shift at wherever the fuck he works, and I tell him about my day of approving designs for the launch of my spring line.

  He rubs my feet while we talk, and his touch makes me tingle all over. I can't give him up. I scoot over on the outdoor chaise we're snuggled on and throw one leg over his so I'm straddling his lap. I unbuckle his pants and pull his cock out with one hand while wrapping my other behind his neck.

  "I missed you," I tell him, then suck his earlobe between my teeth.

  "You just saw me," he replies as he wraps his hand over mine on his cock.

  He's right. I did. And we normally only see each other a few times a month, but Sam asking for exclusivity has made me realize how much I'd miss Greg if I had to give him up.

  "Are you seeing anyone else right now?" I ask.

  "No one serious," he replies. "Are you still with Sam?" He looks curious.

  "I am," I say, keeping a firm grip on his cock. I rotate my wrist a little as I slide it up and down, his hand still lightly covering mine.

  "Why are you asking?" Greg brushes his thumb along my bottom lip, and I suck it into my mouth before responding.

  "I was thinking we could try something new."

  He smiles, a dimple appearing on his cheek. "You want to try anal?"

  "No. Not with you, big guy." I give his cock an extra firm tug and laugh. "I was thinking the three of us could experiment." I hold my breath, awaiting his response.

  "You let Sam fuck your ass?"

  That's the detail he wants to focus on?

  Greg's hands slip under the hem of my dress and grip my lace-covered ass while I choose my response.

  "Baby, you're too big for anal." I decide on flattery as I sit up far enough to slip my panties off.

  "What exactly are you asking for, Jennifer? You want to invite Sam over to watch us fuck?"

  Greg slides his palms across my ass cheeks and spreads them roughly, then shoves a fingertip inside me.

  I love a finger in my ass, but I never encourage backdoor activity with Greg. It's a slippery slope back there, ladies. Admitting you enjoy their finger in your ass quickly escalates to their cocks prodding for entry.

  Which, I enjoy, to be clear. As long as the penis isn't super-sized.

  But Greg's words excite me, so I slide deeper on his finger as I replay what he said. The idea of fucking them individually while the other watches is downright enticing.

  This threesome idea has even more possibilities than I'd even imagined.

  "I want to take you both at the same time," I tell him, moving up and down on his finger. I rest my forehead against his and grip his jaw with my hand. "But the idea of Sam watching us fuck sounds fun too."

  Greg fists himself and slaps my pussy with his cock. "So, I'd get your pussy and Sam would get your ass?"

  I nod. Fuck, I think I'm going to come just from talking about this.

  "It would be an awfully tight fit, don't you think?"

  "Yes."

  "You think you could fit two men inside you, baby? You think you can take us both without tearing you in half?"

  "I could try," I manage to respond. I'm having trouble focusing. The pressure between my legs is volcanic.

  Greg taps my thigh, indicating I should raise up and allow him access. He guides the head of his cock to my slick opening, and I bob up and down on the tip, teasing us both.

  "I love fucking you from this angle. I can see my cock splitting you open."

  I whimper, loving his filthy mouth. I place my hands on his shoulders, balancing myself as he uses his thumbs to spread my lips open so he can watch himself slide into me. It's a little humiliating to be treated like his fuck toy, but it makes me wet all the same.

  "Fuck, Jennifer. Just talking about fucking two men at once is making you a soaking wet little slut."

  I whimper and bite my lip as Greg wraps his hands around my waist and thrusts into me. I mewl as he buries himself to the hilt.

  He's deep. Too deep. I need to move, to alleviate the pain of his cock shoved against my cervix, but he's holding me tight. My thighs burn from trying to lift myself while he holds me down.

  "Greg, let me move."

  "Not yet."

  He slides his hands lower, circling my asshole with his fingertip.

  I can’t do anything but squirm as sweat trickles from my neck, running between my breasts.

  He pushes his finger roughly into my ass.

  "You want this, baby? You want both holes filled?"

  I nod.

  He eases his hold on me, and I grin while sliding myself up and down his cock.

  Our tongues battle while his hands are everywhere: pinching my nipples, gripping my ass, wrapping around my neck until I'm lightheaded.

  He slams me down on his cock and pinches my ass so hard, I know I'll bruise, but that small bite of pain pushes me over the edge. I come, and Greg follows, muttering a stream of obscenities as he floods me with his cum.

  "That was great." I'm lying on his chest, nuzzling his neck and basking in postcoital bliss.

  Greg grunts non-committedly and sits forward, lowering my back to the chaise.

  His feet hit the concrete floor of the patio as soon as his dick slides out of me. I feel his cum on its way south as he drops to his elbows and covers me with his mouth.

  Holy yes. He's never done this before. It's been on my fantasy list for some time, but I've never found the words to ask him to clean up his own mess.

  "Fuck, baby. That feels good."

  I weave my hands in his hair, encouraging him to continue.

  His tongue sweeps inside me, and my toes curl from the pressure of his mouth. He slides over me, our chests pressed together, still clothed.

  I sigh, and he covers my mouth with his own, depositing our combined cum into my mouth.

  I was not expecting that.

  Greg places a finger under my jaw, and a soft kiss on my lips.

  "Swallow."

  I do. I don't have a choice.

  Greg grins as the muscles in my throat constrict.

  I smile back and lick my lips. Might as well be a good sport.

  Greg stands and tucks his dick into his pants as he zips up.

  "Set it up with Sam. I'll do it."

  One down, one to go.

  Five

  Later that week, I pull into the driveway of my father's Bel Air estate still triumphant over my success in convincing Greg to join me in bed with Sam. I still have to convince Sam, but life usually goes my way, so I'm not too worried.

  I find my father by the pool sipping iced tea with a man about my age.

  "Jennifer, sweetheart, you remember Philip?" Daddy asks, waving his hand at the young man. He looks familiar as I glance at him a moment before realization hits.

  "Philip?" I ask, unnecessarily. Philip is a friend of mine from high school. I haven't seen him since the summer after graduation. Wow. I can't believe he tr
acked me down through my dad. I always knew he had a thing for me in high school. Everyone did.

  "Jennifer!" Philip is out of his chair and hugging me before I can process it. "So nice to see you again."

  "You too! How sweet of you to come out to Daddy's estate just to see me."

  Philip smiles and averts his eyes, and my father coughs.

  "Actually, princess, Philip lives here."

  Oh. My. God. How embarrassing. Philip is on Daddy's staff? I could have sworn he went to an Ivy League. How in the hell did he end up on my dad's household staff? Sad. I plaster a smile on my face and take a seat. Rosa places a cold glass of iced tea on the table in front of me.

  "That's great, Philip." I take a sip as Daddy smiles reassuringly at Philip. So sweet, my daddy. "What do you do here?"

  "Do?" Philip looks confused as he glances between us. Daddy reaches over and places a hand over Philip’s as he turns to me.

  "Philip doesn't work for me, princess. He's my lover."

  Holy. Fuck.

  I manage to plaster a smile on my face before speaking, but what the hell? There's a fifty-year age difference between Philip and Daddy.

  "Daddy, Philip is my age."

  "So? We make each other happy. If it's okay for Hugh Hefner, it's okay for the gays, darling."

  I open and close my mouth, unsure of how to respond to that.

  "Listen, Jenny. I called you over for lunch to let you know we're going to miss your birthday this year."

  What?

  They're a "we" now? And Daddy is missing my birthday? He's never missed my birthday. Ever.

  "I'm taking Philip to Italy. He's never been. Can you believe it?"

  "Tragic," I say, though I could not care less. How dare Daddy miss my birthday? This is unheard of treachery. I make a mental note to ask my lawyer if we should request a mental competency check before this gets even more out of hand.

  Six

  Sam hands me a glass of wine as I drop onto his couch and toe off my heels. He sinks into the spot beside me and rubs the back of my neck as I let out a groan.