Backseat With The Billionaire

by Lilah May

  But he doesn’t. Instead, he just teases me, his fingers swirling around the entrance, building me up but not letting me go. I can’t stand it anymore. I’m going crazy from his touch.

  “Please.” One word. That’s all I say, but without warning, he slams his fingers deep into me, his thick digits spreading me wide, just how I wanted it, just how I imagined it.

  My pussy clamps down immediately and this time, a scream does rip through me as the wave of pleasure hits me wildly. His touch is too much and the sweet sensation overwhelms me. My head spins and right there in Bobby’s car, I cum.

  He bent me to his will so easily, taking me so fast I didn’t even have time to refuse, to tell him this wasn’t right. How can I when I feel so good under his control?

  Laying across his knee as he drives, not even looking at the begging slut in his clutches, I cum for what feels like the first time in my life.

  Writhing and thrashing on his lap, I buck my hips against his firm hand, my pussy never letting go of his fingers

  I clutch his hard steel cock for support, my face buried in his leg, muffling my screams as I bite down on his taut, unyielding muscles.

  My entire body tingles and vibrates as the energy and pleasure climaxes and wanes.

  When my head starts to clear and my body starts to relax, I crawl off of his lap, sheepishly pulling my panties up and rearranging my dress.

  “Is that what you wanted?” he asks. It was exactly what I wanted, what I fantasized about for that long month alone lying in my bed dreaming of Bobby’s mouth on my breast.

  But that was just a fantasy. I shouldn’t want it with Bobby. But that only made it even more delicious.

  God, what must he think of me now? I must look like the lascivious whore he made me into, just like the last time when we didn’t know each other, when he thought I was just another woman who was dragged helplessly into that whirlwind of his primal lust.

  Did he even see me as the woman who talked him through his first breakup, who helped him through his parents marriage troubles? Did he respect me at all or did he think I was just like the rest of the girls he had probably taken so easily in college?

  He finally looks down at me but I can’t tell what he’s thinking behind those swirling mysterious dark eyes.

  “Is that what you wanted?” He repeats again. “When you walked into a shitty bar full of drunk perverts, dressed like the most beautiful woman in the world, and drinking more than a frat boy?”

  I don’t know what to say to put an end to this. But I can’t let this go on anymore. I can’t let him think of me as some sex toy he could play around with.

  I’m supposed to be his elder, his support, his mother figure. Will he ever see me the same again? I want to cry.

  What have I done? Have I done irreparable damage to that special relationship we had before this? We had been so close.

  His mother not one to hover, he had always come to me with his problems, with his worries. The tears start to well up inside me, threatening to spill out. I was angry at myself, for letting myself go like that just for some sex.

  “I asked you a question. Is that all you wanted? To cum? Or did you want the part where you were forced? Or was it the pain, the spanking?”

  “No, I — I didn’t want this.” My voice comes back to me, albeit shakily. “I shouldn’t have done this. Especially with you.”

  “Oh, so you’d rather have a group of old shitbags rape you than have me make you cum.” He’s vicious and he has every right to be.

  “No, that’s — that’s not what I meant.” Frustrated, the tears start to leak, rolling down my cheeks. Is there any way to make this right? “Bobby, that wasn’t — I don’t — we can’t do that.”

  I don’t know what to say to make things better. To get things back to normal.

  “What you did was fucking dangerous. You can’t just walk into a group of criminals and expect to come out unscathed. Do you realize what would’ve happened if I wasn’t there? Even if you don’t care about yourself, imagine how I would feel, how Ava would feel, if we found out.”

  “I know. I’m sorry.” When I say the words out loud, everything becomes real. What happened before, in the bar, it didn’t seem so much like an old western movie anymore.

  I realize I had almost been raped and suddenly, I can’t hold back my tears anymore. I cry, silently, cursing myself for being so selfish, for acting so childish.

  He was right. I had known he was right. I just didn’t want to admit it. Because I’m supposed to be the adult, the one in charge, having everything under control, but I didn’t. Everything was out of control, my life was in pieces, and the only person I could lean on right now is Bobby.

  “I’m sorry. I’m so sorry. I was so scared.” Not just of the men at the bar, but of my uncertain future. It seems like only chaos and confusion lay ahead.

  “Don’t worry. You don’t have to be scared anymore. I’m here, now. And I’m not letting you out of my sight.” I never knew words could be so comforting, so warm. “After everything that happened to you, you have every right to be acting a little crazy.”

  “But, Bobby. You know we can’t do that anymore. That thing in the grocery store, that had to be a one time thing.”

  “I guess it’s a two time thing now.” Bobby smiles, trying to ease my apprehension. “You’re right, though. I went a little too far. I was scared, too.” He was scared? What could Bobby be afraid of? He’s always so confident, so fearless. “I thought that if I didn’t teach you, if I didn’t show you how dangerous that was, you might end up doing the same thing. I was scared what stupid thing you might do next and what someone might do to you, if you didn’t learn.”

  “I’m sorry for worrying you like that, for scaring you. I was acting like a kid. Look, I know what I did was wrong. I knew it as soon as that guy touched me. I just didn’t want to look so … pitiful in front of you.”

  “I’ll never think that. You’re the strongest woman I know. Stronger than me, even.” What is he saying? Bobby has always been the one to never cry, never show any sign of weakness. Even when he was a kid, he used to fight off the bullies all by himself without one tear.

  “You’ve been through so much more than me and you’re still the kindest person I know. That’s what real strength is.”

  “Thanks, Bobby.” He’s just trying to make me feel better. “So can we just forget about what just happened? I swear I’ll never do something like that again.”

  He grins, and I don’t think he’s going to let it alone. I’m not sure if I want him to.

  “Please?”

  “OK. But ignoring what we just did or more appropriately what I did to you.” He winks one last time before his face turns serious. “What were you doing there? And don’t tell me that bullshit about you being a slut. I’ve watched you for 15 years and you’re not that person. Even that part of you that you’ve never shown anyone, that likes this kind of thing. It wouldn’t make you so reckless. Something set you off tonight. Something drove you off the deep end.” He’s right. How does he know me so well?

  “It’s nothing,” I mumble.

  “It’s not nothing. If it made you go this far, it must be something. You’re an intelligent mature woman and there’s a reason why you ended up here. Now tell me that reason.” His voice sounds demanding but calm, firm but trusting. Like a concerned dad, worried about his little girl. And just a few hours ago, I thought there was no one in this world who cared about me. My family all but gone. I thought I was alone.

  But he cares. He really does care. It isn’t an act. He cares about me, worried about me. Someone cared. That fact makes me warm inside. It feels safe. Like being rocked to sleep by your lover.

  And I break down all over again, crying like the little girl I acted like all night, all the pent up frustration, anger, and fear spilling over.

  His arm drapes around my shoulder, pulling me close, and I let him hold me tight, burying my head into his shoulder. He waits, patiently, wi
thout a word until I finish.

  Finally, my tears dry and my sobs are reduced to hiccups. It feels so right crying in front of him. No matter how silly whatever I was crying about seemed, he accepts it.

  Handing me a handkerchief, he takes a brief second to look at me, to make sure I’m alright, with his beautiful deep worry filled eyes. He’s grown into a real man. A strong, kind man.

  “So, what happened?”

  “It’s so stupid. I don’t even want to say.”

  “I like to listen to stupid things. So hit me with it.”

  I take a deep breath. “Last night, I got an invitation to an engagement party.”

  CHAPTER 12

  LISA

  Two hours earlier, I was staring at a card, adorned with printed flowers and elegant cursive: Congratulations Mr. and Mrs. Howard! We cordially invite you to celebrate the engagement of Donald and Ariana Howard.

  I couldn’t believe it. Engaged? Our divorce wasn’t even complete. Is that even legal? And Mrs. Howard? They’re not even married yet.

  I’m still Mrs. Howard.

  And he sent the invitation to this house, to our house. It might be addressed to Ava, but he knew I would see it. What 13 year old girl checks the mail? I pick up my phone and pull up his contact. My thumb hovers over the call button.

  No. This was what he wanted. This was why he did it. So he could make me upset, make me call him, and yell at him, give him the satisfaction of winning, in whatever sick game he was playing.

  This was just like him, the passive aggressive dick. Always with these little mind games. If he knew how depressed I had been this past year, he would be dancing a jig.

  How did he just leave like that? Without a second thought, abandoning the family that I endured so much for, bit my tongue for all these years. How could he do that?

  Maybe I was jealous. Maybe he was onto something. Did he find the key to happiness? Doing whatever he wanted, with no care as to who gets hurt. Live selfishly. But Donald would never be happy, wherever he was. Always obsessed with what others had and what he didn’t, constantly thinking the grass sure looked sweet on that other side.

  But that doesn’t mean I can’t be happy. But that leads to another question. I don’t know what makes me happy. The thought left me catatonic. This is why I barely left the house for the past months, why I shut myself in for so long.

  It scares me. The world scares me. Can I just go out there and find my happiness just like that? Or would I have no place in this new, unfamiliar world? Would it just chew me up and spit me back out. I didn’t think I would be able to handle that.

  So I sat and sat and sat. Until today. My husband and his mistress are getting married. No fucking way are they gonna win. Armed with my black dress, I drove fifty miles to a random town and walked into a random bar.

  ***

  “And that’s when I met you at The Soggy Dog.” He had stayed silent through my whole ranting narrative, listening as if my problems are his, as if they aren’t just the ramblings of a depressed divorcee.

  “Wow. Donald might’ve found someone new, but he’s still the same old dick, huh?” I laugh, loving that he takes my side no matter what. It feels good to have someone looking out for me.

  “Yea, I know.”

  “So? What were you hoping to find there?”

  “I don’t know. I had this idea that I would have a one night stand. To show myself that the world wouldn’t eat me up.” I had actually imagined myself quite vividly in some shady motel, staring at the ceiling, examining the peeling pink paint and the brown water stains while a sweaty drunk mess slobbered over me, grunting in a horrible rhythmic fashion directly into my ear. But I’m not going to tell him that. “I would realize that all of this wasn’t so bad.”

  I don’t mean the sex. The sex would be bad. But the experience. If the worst sex wasn’t so bad, this sweaty suffocating sex, then whatever I tried wouldn’t be so bad.

  “And after finding out the world wasn’t so bad, what then?” Bobby asked.

  “What then? I guess, I just wanted to find myself. Find out what I liked. What I wanted to do. Like when you’re in your 20s and you switch majors in college, you get hired, get fired, get hired again, then quit, to find who you are. Maybe not for you, Mr. CEO at 22. But for normal people. I missed out on that, getting married and having Ava so young. I want that.”

  “So basically, you want to try things out, have some fun.”

  “What? No. I want to find out more about myself, find passion, find love.”

  “Right. You’ve spent all your life living for other people. Now, you want to live for yourself. Now, you want to have your kind of fun.” How does he make it sound so simple? Here I am giving my deep and profound speech, and he boils it all down to fun. Is it that simple?

  “When you say it like that, I guess you’re right. I want to have fun. But it’s not so simple.”

  “Of course, not. It’s a highly complicated process to reach that realization like Buddhist monks going into a hermitage to obtain enlightenment. But you’ve already done the hard part, freeing yourself. Once you do, though, it’s very very simple to move forward from there.” I don’t know if he’s being sarcastic. What is he saying?

  “If it’s so simple, what do I do?”

  “You just go and have fun. Try everything you’ve never tried before.”

  “How?”

  “Just leave it up to me. Or actually, since I’m driving, you do it.” He tosses me his phone.

  “Wait, are you sure? Aren’t you scared I’m going to read your sexy texts with all of your college girlfriends?”

  “They’re called sexts and I don’t have a girlfriend.”

  “No girlfriend? You don’t have to lie. It’s not like I’m going to go rat on you or something.”

  “Just scroll down in the contacts to Vinny and text him ‘Set me up for tonight, plus one.’”

  “Sounds mysterious. What is there to do on a Tuesday?” I send the text to Vinny and he immediately texts back Go for gold, bro. You got this.

  “You’d be surprised. That’s the best part of living near The City. Whenever you want to have fun, you can have fun.”

  “But that’s like an hour away!”

  “I had a feeling you weren’t done for the night. We’re almost there. Look outside.” I look out the window and he’s right, we’re about to enter the tunnel heading into the city, the lights of the bustling metropolis twinkling over the turbulent river.

  CHAPTER 13

  BOBBY

  I know exactly what Vinny has planned. Or more like, what I had planned because I had built the app myself.

  You put in a dollar limit, a time schedule, number of people, their ages along with a few preferences, and it spits out an agenda for the night. If you like it, with one click it makes all the reservations, buys all the tickets, and even calculates the estimated amount of time it takes to travel between venues.

  But that part’s just for every other person who bought the app. Vinny ran the VIP division, a restricted department meant for deeper pockets who would receive customized itineraries along with access to exclusive restaurants, parties and clubs that were invite only.

  To be honest, I had planned this night since the day I learned Lisa was getting a divorce, barring the little hiccup with my fight tonight. So I didn’t even have to look at the schedule he sent me.

  “So where are we going? Or do you not know either? Is Vinny making the plans?”

  “No, he’s just making the necessary calls to get us in. The places we’re going have been personally picked by yours truly. First things first. We need to get some food in you.”

  “How do you know me so well?” I look over at her staring at the passing buildings and all I can see is the swell of her tits, her sweet ass presented towards me.

  It takes all my willpower to stop myself from pulling the car over and take her on the side of the road. Pushing her creamy tits up against the cold glass window so the passing cars c
ould see a glimpse of how beautiful she is.

  Maybe even drag her outside and lean her over the front of the car, her cheek pressed against the hot metal of the hood as I slam my own hot metal into her from behind.

  I would never have thought to find her at that bar, especially looking like that.

  I’m never surprised, never on the back foot, otherwise I would lose millions in a second in the boardroom. But she always seems to catch me off guard, something even the most powerful and richest executives can’t do.

  Nothing surprises me anymore. Except Lisa.

  Maybe that’s why I’m obsessed. I’ve never been scared before. But she makes me feel fear, fear of her getting hurt.

  I didn’t like taking advantage of her cause I know she‘s an emotional wreck. But I couldn’t stop myself. And knowing how much she wanted it didn’t help. And how much it scared me if she didn’t learn her lesson and went off doing risky things like that again.

  I had to teach her. Set her straight.

  But in the end, I shouldn’t have touched her. I lost control. She’s a special woman, the perfect woman, the woman I love and loved for my whole life.

  And she deserves that real love, the right way. Not this fast, carnal way. Our love should build slowly. She deserves every step, the wooing, the kissing, the longing, the climax.

  And I skipped straight to the end. The way she acted, defiant and petulant, made me into something primal, something possessive.

  And so in the car, I claimed her. I made her know that she was mine.

  She wasn’t to be had by anyone else. Only me. I can still smell her on my fingers and it makes my cock stir.

  I want to take her completely, but I need to wait. She deserves a date.

  I just hope I can hold myself back before the end.

  ***

  Glen Rock is an island and the biggest city in the state, not to mention third biggest in the country, with a population of 2.5 million people.

  The place I bring her to is in the middle of the business district on the west end of the city. The West End is full of skyscrapers and official looking people walking around even at this time of the night.