Training Their Virgin Assistant: A BBW Billionaire Menage Romance

by Harper West

  There’s no doubt about it – going forward, Jay and I are going to have to make Jilly a priority if we want to keep her in our lives.

  In the morning, my head is killing me. I wake up when it’s still dark and groan, reaching over to the nightstand and fumbling for a bottle of water. My hand collides with the plastic, sending it crashing to the floor, and I curse loudly.

  Why the fuck did I drink so much the night before?

  And god, I’m seriously getting older. Back in my twenties, I used to drink all night long and nothing bad would come of it. I’d wake up the next morning and practically bounce of bed.

  Getting older fucking blows.

  I crawl out of bed and get into the shower, praying that the hot water will do something to alleviate the massive hangover beast that’s got me clenched in its jaws. I brace myself with both hands against the glass wall, head down under the waterfall spray, until I feel almost normal again.

  But it doesn’t last. The water goes cold and I’m left feeling almost worse than I did before. I get dressed in a Valentino suit, armor myself with sunglasses, and leave for SMX.

  As the CEO, I don’t have to be there every day. In fact, I don’t have to do nearly as much of the shit that I do. But knowing that Jilly will be in the office, bustling around in some tight skirt with that ass of hers on display, tells me that there’s no way in hell I could stay home.

  Other men could be gawking at my girl all day.

  I couldn’t fucking have that, now could I?

  Outside, it’s miserably hot and it’s not even eight-thirty. The heat is rising up from the pavement like steam from a griddle, and I’m sweating into my Valentino before I can even step into the back of my car. My driver has the cold air blasting and that, combined with my wet hair and sweaty skin, makes me feel like I’m about to puke.

  “Rough night?”

  I respond by rolling up the partition that divides us and closing my eyes.

  The lobby of SMX is bustling and filled with people waiting and darting around with coffee and bags and briefcases. The early morning smells – perfume and cologne, makeup, hot tea – aren’t contributing to my nausea, and I half-consider leaving and going home to take a nap when I see her.

  Jilly’s standing, waiting for the elevator, sucking on the end of a pen like it’s my dick in her mouth. She sees me and blushes, making her eyes big and giving me a saucy look. Even in my pathetic, hungover state, the sight of her is enough to make my cock hard.

  If she could blow me in the elevator, that would be so great right now, I think as I stride over, smirking at her, hangover already forgotten.

  “Hi,” Jilly says shyly.

  Jay comes up behind her and he and I share a look over Jilly’s head.

  “You guys are quiet this morning,” Jilly says. She giggles, still gnawing ferociously at the pen.

  “It was a long night,” I say.

  I may have gotten way too fucking drunk last night, but standing here with Jilly and Jay, I know everything Jay and I discussed at the bar is true.

  Jilly’s ours – she’s our girl.

  And it’s time to let her know.

  Chapter 15

  Mason

  Days turn into weeks, and weeks turn into months. The summer passes, hot and unrelenting.

  Jilly and Jay and I spend it together, lounging in my California king-sized bed, with her in the middle and the air-conditioning on full blast.

  Jay and I don’t talk about it again. We’re allies, having forged this path together, and it grows sweeter every day.

  I learn about Jilly. I learn her favorite foods (pasta with cream sauce, and those little German hazelnut candies for dessert) and eat them off her body one afternoon, savoring the salt of her skin as it mingles with the pasta. I learn about her childhood – full of loving parents, with no siblings, although her best friend Penny is more like a sister than a friend.

  Everything about her is so spectacularly wholesome, so normal that when I see her on her knees, riding Jay’s dick and sucking mine, it’s more of a turn-on than ever before. When I take her up the ass, I think of how she probably never even considered doing anal before she met me.

  It fills me with a glowing, possessive sense of pride that the only two cocks she’ll ever know are mine and Jay’s, and that we both fit so perfectly in her holes.

  There’s no doubt about it: I’m completely falling for her. This sweet, ditzy, curvy girl is mine, and I want her to be mine for the rest of my life.

  One day, I walk into Jilly’s boss’s office. Jilly’s sitting at his desk, typing up some notes, and she barely looks up until I clear my throat.

  “Oh my gosh, Mason, you startled me!” Jilly squeaks. She blushes – even after six months, she hasn’t gotten used to me sneaking up on her, and my balls ache with lust for her and her sweet, round body. She’s gotten even curvier over the months, and I fucking love it. Jilly hates it – she complains about not being able to fit into her clothes – but I’ve never seen her as sexy as she is now. Her tits are practically spilling out of a button-up shirt, and I have to stop myself from leaning in to kiss her and grope her gorgeous body.

  “My apologies,” I say, with just a touch of sarcasm. “I was hoping you’d join Jay and myself for dinner this evening.”

  “Of course,” Jilly says. She smiles happily at me.

  “It’s formal,” I tell her. “Very formal. Le Creuse.”

  Jilly blinks at me. “Wow,” she says slowly, taking in the sound of New York’s most expensive, most exclusive French restaurant. “Special occasion? It’s not your birthday, is it? Or Jay’s? Oh my gosh, I’m the worst girlfriend in the world, I’m—”

  I hold up my hand to silence her. My lips curl into a smirk.

  Girlfriend. That’s right. She’s our girlfriend, I tell myself, and my smirk turns into a grin. Girlfriend.

  “We don’t celebrate birthdays,” I tell her. “But it is a special occasion.”

  Jilly looks at me and cocks her head to the side “What is it?”

  “It’s been six months since you and Jay and I ... well, since we began our arrangement,” I say.

  “Six months?” Jilly blinks. “Wow.”

  “I know,” I tell her. “It’s gone quickly, hasn’t it?”

  She nods. “I’d love to,” she says. “Does Jay know?”

  “It was his idea,” I say. “So, you’ll have to thank him.”

  Jilly grins. “I think I know how to do that,” she says, making my cock throb with lust for her.

  “I believe you do,” I say, raising an eyebrow and grinning. “I believe you do.”

  That night, I feel like I’ve died and gone to heaven. I’m sitting at the most exclusive table at Le Creuse with Jilly at my side. She’s poured into a dress – a red, sparkly thing that Jay found at Saks and thought would be perfect for her. Her tits are nearly spilling over the edge and I have to keep my hand in my lap, or else it would go to her chest and pinch her nipple through that loud fabric.

  Jay’s in high spirits. He’s ordering bottle after bottle of Dom Perignon, making a show of pouring for Jilly and myself, pretending to be the waiter.

  “I can’t believe this,” Jilly says. She giggles and I see that she’s flushed from the champagne and the excitement. “I’ve never had escargot before, but they’re really good. I always thought eating snails was really weird, like, you know how rich people always do this gross shit and then laugh when other people copy them?”

  I snicker.

  “They’re delicious,” Jay says. His eyes are lingering on Jilly, clinging to her curvy form. “Just like you.”

  “You taste far more exquisite than escargot,” I tell her. I reach for her hand, stroking her palm with my thumb. I can see that her other hand is in Jay’s lap, under the table.

  Jilly bites her luscious, pink lip. “Thanks,” she says, still giggling. “I can’t believe I’m thanking you for saying I taste better than snails!” She reaches for her champagne flute and pick
s it up, wetting her lips with the tip of her tongue before taking a sip. “I’m so tipsy,” she moans, rolling her eyes back in her head and arching her neck. “I hope I’m not acting like a total idiot.”

  Watching her, my entire body is on fire with lust. I don’t care about this fucking restaurant anymore – I want Jay and I to carry her out of here over our shoulders, fuck her in the back of my limo, make her take both of our cocks at once.

  Make her love every single second of the debauchery.

  “You’re not,” Jay assures her. He smirks at me and shifts to the side. I can’t see it, but I can tell that he’s putting his hand on Jilly’s leg under the table, inching his fingers up her thigh.

  Her reaction is delectable. She moans and quivers, spreading her legs until I feel one of her round thighs shaking against my own. The rosy flush on her face grows dark and she bites her lower lip ferociously, closing her eyes and rolling her hips.

  “Jay,” I growl. “We don’t want to be thrown out, do we?”

  Jay finally tears his gaze from me and turns to Jilly. Leaning in, he gives her a deep, wet kiss. The sight of it makes me hunger for the touch of her petal-soft lips against my own.

  Thankfully, I don’t have to wait long. Jilly turns to me, her lips wet and glistening with saliva and champagne and lust. She breathes Dom Perignon in my face, then moans softly into my mouth before pressing her lips to mine.

  She tastes heavenly, and I practically cream my pants she turns to me, pressing her luscious tits to my body and shaking. Her tight red dress is hiked up nearly to her waist, and I glance quickly down to see Jay’s wrist moving between her thighs.

  “Let’s get out of here,” I growl into Jilly’s mouth.

  She pulls away and swallows. Her big brown eyes are wild with lust and she smiles happily at me.

  “But what about dinner?” Jilly asks, pouting coyly at me. I nearly groan with desire. She’s clearly testing me; she knows I want her.

  She just wants me to say it.

  “We’ll go to a hotel,” Jay offers. “I know a nice place around here.”

  “But dinner,” Jilly says, in almost a whine. “I’m hungry.”

  “You’re hungry for my cock,” I say, too quiet for anyone but my sweet girl to her.

  “And then we can get room service,” Jay says. He gives her a wicked grin.

  “Come on, baby,” I tell Jilly. “Let’s go.”

  Taking a few hundred dollars from my pocket to cover the champagne and the canapes, I take Jilly by the hand and lead her out of the booth. She walks in front of Jay and myself and I can’t tear my eyes away from her magnificent ass, as it swings from side to side.

  Jay’s eyes meet mine, and there’s a clear message there.

  Tonight is gonna be the night of our lives, I think.

  And we’ll make sure it’s a night that Jilly won’t ever forget, either.

  Chapter 16

  Jilly

  I can’t believe it’s been over six months since Mason, Jay, and I ... well, to be honest, I’m still not sure what exactly it is that we’re all doing together. I’ve completely fallen for them – both of them – and I can’t picture my life without them.

  It’s been like living in a dream. A sweet, sexy, dream that’s filled with orgasms and rich foods. I’ve gained even more weight, which I can’t stand, but Mason and Jay seem to love it.

  They seem to love me.

  I just wish I had the courage to have the conversation I’m dying to have with them both. To tell them that I love them, that I want to do this for the rest of my life, or for however long they’ll have me.

  I’m scared, though. They think I’m this perfect little girl, and it’s so hard to see myself that way. It’s impossible to think about being worthy enough for one man, let alone two gorgeous billionaires who can’t keep their hands away from me.

  What’s going to happen when they get tired of me?

  “Jilly, I’m sorry to rush you, but I really need the bathroom,” Penny calls from the other side of the door.

  “I’ll be out in just a second,” I say weakly. “Just a second,” I repeat, louder this time.

  I’ve been hunched over the toilet for over twenty minutes, and I still can’t stop gagging. It’s crazy – how the heck can I be throwing up so much when I skipped dinner last night? I haven’t eaten in almost twenty-four hours, and the bile just keeps coming.

  “Jilly, come on,” Penny yells. She raps on the door. “What’s going on in there? I really have to pee!”

  I get to my feet and flush the toilet, rinse out my mouth in the sink, and open the door. Penny’s standing there with her hands on her hips, looking pissed. But when she sees how wan and pale I look, her frown fades.

  “Honey, you look awful,” Penny says. “What’s going on?”

  “I think I’m so anxious that I made myself sick,” I confess.

  “What’s going on? Here, come in with me,” Penny says. She grabs my hand and yanks me back in the bathroom. I look away as she slides her jeans down her hips and sits on the toilet, moaning with relief as she pees.

  “I’m really sorry that I was rushing you,” Penny says. She groans. “I felt like my bladder was going to explode. I drank like, six bottles of water last night.”

  Even the mention of something as mild as water is enough to make my stomach start rolling again, and I take a deep breath and swallow hard so I won’t puke. My whole body hurts just from throwing up, and my face is puffy and glistening when sweat.

  “So, what happened? Did you guys get in a fight?” Penny asks sympathetically.

  I shake my head. “No,” I tell her. “I’ve just been so worried. Things are going so well, and they can’t go on like this forever, and ...” I trail off anxiously. “I’m just really scared that they’re going to get sick of me.”

  “Is that it?” Penny asks. She narrows her eyes at me. “Hon, you gotta pull yourself together. You all have been together for, what? Six months?”

  I nod.

  “Well, the honeymoon period might not last forever,” Penny says delicately. She gets to her feet and yanks up her pants before washing her hands in the sink and shaking them dry. “I mean, it usually never does.”

  “I’m not worried about that,” I say. “I can’t explain it – I feel like such an idiot, but every time my mind starts wandering all over the place, I start to feel sick.”

  “Just in the mornings?” Penny asks.

  I shake my head. “No,” I tell her. “At night, too. Well, all the time, actually.”

  Penny’s expression changes. “How long have you been feeling like this, sweetie?”

  “A couple of weeks?” I frown and try to calculate backwards. “Maybe like a month,” I admit. “I know I need to talk to them, but I can’t ever seem to find the right time to bring it up when we’re all together, you know?”

  Penny opens her mouth to speak, then closes her lips. “Hey,” she says suddenly. “Are you doing anything tonight?”

  I shake my head. “Not as far as I know, why? It’s a Monday – Mason usually works late and Jay has squash with his brother.”

  Penny smiles faintly. “Let’s have a girls’ night, okay?”

  I nod. “That sounds good,” I tell her. “I’m sorry that I haven’t been around much. I feel like I’ve been a really bad friend.”

  “Don’t worry about it,” Penny says. “I’ve been busy, too. Anyway, I’ll grab snacks and drinks and stuff. We can watch some movies.”

  I get the sense that she’s hiding something from me, and I brace myself for an awkward comment about Mason or Jay, but Penny doesn’t say anything.

  “I should get going,” I say. “I’m already going to be late.”

  At work, I find that I can’t focus on anything. My mind is running all over the place – from Mason to Jay and back again. Why do I have to be such a big baby, I think to myself. I just need to find my lady-balls, or whatever, and talk to them. Tell them how I feel!

  Thinking tha
t makes my stomach hurt and before I know it, I’m running to the bathroom again. I barely make it to the toilet before vomit spews out of my mouth and fills the bowl. Some of it goes up my nose and I gag and cough as the acrid bile burns.

  God, this is awful, I think as I lean back and wipe my mouth on the back of my hand. I have to do something, I can’t keep puking every day out of fear that they’ll dump me.

  Back at my desk, I keep my eye on the clock for the rest of the day. The hours seem to drag by. I don’t see Mason or Jay all day – not unusual for Mondays, but it makes me feel even worse.

  What if they’ve already gotten sick of me?

  What if they don’t even feel like telling me, and they’ve already moved on?

  I know that the thoughts are stupid and irrational, but I can’t stop them.

  By the time I get home, I’m a wreck. True to her word, Penny loaded up on all of my favorite snacks: Chex mix and pretzels filled with peanut butter and pizza chips. She even has a tray of wings baking in the oven. The smell is heavenly, and for once I don’t feel nauseous.

  When she comes out of her room and smiles at me, I smile back in relief.

  “How are you feeling?” Penny asks.

  “Better,” I tell her. “Like, maybe this is what I’ve been needing. Just some time with my best friend.”

  “I hope so,” Penny says. She settles down comfortably on the couch, crossing her long legs under her torso.

  “Thanks for getting all of this,” I say as I reach forward and take the bowl of snack mix from the table. It smells heavenly – even better than the Wagyu beef and lobster thermidor that I’ve been eating with Mason and Jay – and I grab a huge handful. I’m suddenly starving, like I haven’t eaten in days, and the crunchy, salty, tangy blend of pretzels and crackers and peanuts is heavenly.

  “You seem like you’re feeling better,” Penny says. She raises an eyebrow at me.