Backseat With The Billionaire

by Lilah May

  “Are you OK, Mrs. Howard?” Still with this Mrs. Howard thing. How long is he going to keep this up for?

  “It’s actually quite cozy. Reminds me of my bed. And don’t forget about the Ms.”

  “Sorry, I don’t think I’ll ever get used to that.” He has to be playing around with me.

  “Don’t worry about it. I’m sure you’ll learn soon enough.”

  “All right! After a long hiatus, let’s welcome back the annual Carter-Howard camping trip!” And with that Rob blasts the sultry sweet yet smooth soulful voice of Dean Martin.

  As he takes the necessary lefts and rights to escape the suburbs and get onto the highway, I slide this way and that across Bobby’s lap.

  I can feel each of his abs massaging my back, his hard pecs on my shoulders, the bulges of his quads under my butt. Every muscle is so defined, the taut unyielding strength of his amazing body leaks straight through my dress.

  What the hell have I gotten myself into? Being so close to Bobby is like being sucked into a vortex of sexuality I can’t pull myself out of. The thought of his young hungry cock inches away from my deprived pussy has me shivering in anticipation of what I tell myself again can never happen.

  “Oh! I love this song! Like a flower bending in the breeze. Bend with me, sway with ease. When we dance you have a way with me. Stay with me, sway with me.” Leaning left and right as I sing along, my butt wedges tighter and tighter between his stout thighs.

  And from the depths of his groin, I finally feel the base of his thick cock, the rest of its length I imagine hanging right below my ass. I can’t help but think if he gets hard, the thick shaft will lodge right between my cheeks.

  “I can see why you like it. It’s very sensual.” He places his hands on my thighs, the rough calluses scraping the soft vulnerable flesh. My legs tingle, craving more, for him to move his hands up, all the way up to that hidden spot beneath my dress.

  I look at his face and his eyes are glued to my chest. I realize through all my shifting and sliding, my dress neckline had been pulled down to expose much more than the original design intended.

  The top of my milky white breasts are completely visible all the way to the lace edge of the bra, which reveals a subtle hint of the darkness of my areolas.

  He’s practically drooling over my tits and I feel the heat of his gaze on me, my nipples stiffening at the attention. Thank god for the bra. I pull the dress back up even though he’s already seen and touched much more.

  But that’s when I feel it, his rigid cock pushing against my butt. I jump, reacting, raising myself off of him.

  “What’s wrong, Ms. Howard?” He acts nonchalant as if he just didn’t pop a boner under my ass. I knew it. This is his plan all along. But I’m not going to let it faze me, no matter what he tries to pull.

  “Um. Nothing, just readjusting.” I settle back down gingerly, in hopes of calming his raging cock. But instead it gets bigger and bigger by the second, inching it’s hardness between my cheeks.

  This is going exactly where I don’t want it to.

  Maybe I can distract him with some small talk.

  “You know you kinda look like Dino?”

  “Do I?”

  “Yea, with your dark hair and easy smile. Ohh, he made my knees weak.”

  “Mmm sounds naughty. Tell me more.”

  “You’re so silly.” I playfully slap his knee.

  “You know who made my knees weak when I was a teen?”

  “You mean last year?”

  “Very funny. But yea, since I was a wee little boy till even now.”

  “Really? I need to know, who was little Bobby’s celebrity crush? Britney Spears? Miley Cyrus?”

  “You really want to know?”

  “Stop teasing and tell me.”

  “It’s you, Ms. Howard.” All of a sudden, I’m intensely aware of the warmth of his breath playing on my ear, his hard muscles rippling beneath me, every part of me that touches his body starts to tingle.

  Every time he proclaims his love, every time he calls me sexy, he has the same disorienting effect on me and I feel the heat rising to my cheeks like a little schoolgirl. And the heat filling my needy pussy.

  “Stop playing with an old woman’s feelings.” I giggle in an attempt to cover up my nervousness but the weird high pitch betrays me. Does he notice how tense my body is? He has to.

  “I’m not playing with anything. I’m not the same boy you knew before. And you’re not an old woman. You’re still ravishing. I’ve been fantasizing about you since I was young and you’ve only grown sexier since then.”

  “Fantasizing?” I’m on my heels here. He was fantasizing about me? He could get any woman he wanted with the snap of his fingers and he had been watching me this whole time? He’s wanted me all this time?

  “You know I used to come over and play with Ava just to see you, to be near you? Whenever you would go for a swim in your pool or tan on your porch, I would peep and stare at you the entire time.” I’m glad the windows are wide open, the wind rushing through the car and Dean Martin blasting from the speakers keeps anyone else from hearing these dirty secrets he’s suddenly springing on me.

  “I knew that. I kinda liked it. It made me feel … nice.” I had been at my lowest point, especially because Donald was never intimate with me after Ava had been born.

  Completely consumed by insecurity and with the accompanying weight gain, I thought I was hideous. Until that one day I saw Bobby rush out of his house right around the time I would sit by the pool.

  Suspicious, I kept watch through my sunglasses and sure enough, his little head poked over the fence, looking right at me. And I let him. I know it was wrong, I should’ve stopped it. But I liked it.

  I kept doing it, wearing skimpier and skimpier bathing suits, finally proud and confident from a little boy’s attention. How sad was I?

  It was messed up to let that happen, much less to encourage it. But it felt good, to be wanted, to be desired. Especially when I believed nobody would find me attractive again for the rest of my life.

  Unbeknownst to Bobby, he had been saving me from myself.

  “Did you know that I was masturbating behind the fence?”

  “What? Bobby! What if someone else saw?” This is a surprise. I didn’t think anyone did that in real life.

  “No one could see me from that spot. Although I hoped you would catch me.”

  “Why?”

  “Well, in my fantasy you wouldn’t get mad. Instead you would help me out and from then on whenever I wanted to get some relief, you would use your hand.” Being used for his satisfaction, for his pleasure feels so dirty. I feel my skin start to prickle as heat spread through my body. But I can’t let him notice. I told him we couldn’t do this anymore.

  “You’re lucky I didn’t catch you. I would’ve told your mom right away.”

  “Then why aren’t you telling her, right now?” He flexes his shaft up as the hard ridge presses further between my legs. He’s so bold. How does he know I won’t out him right now?

  “I don’t want to get you in trouble,” I reply weakly. He knows it’s just an excuse. He’s always had control over my body since the first day in the grocery store. But I thought I would be strong enough mentally to deny him.

  “My favorite part of the day is when you would come out of the shower in that pink sheer robe. I could see everything through that robe, the hint of your nipples, the shadow of your pussy. I would have to go into the bathroom to jerk off. I would imagine you wore that on purpose, just for me and the thought of you teasing me would make me finish in less than a minute.”

  “But you were just a boy! I didn’t know I had that effect or I would never have wore that in front of you.” I’m equal parts horrified and delighted. I had no idea I had been fueling little Bobby’s fantasies this whole time.

  It was so wrong and taboo but for some reason it made my stomach flutter. Plus, that boy was now grown and still held that same desire, the same hot de
sire that was pressing against my own wanting pussy.

  “What’s wrong with that? Every boy has fantasies.”

  “It’s OK, I understand. You were just a horny teenager and I was the closest woman. It’s only natural. But now that you’ve been to college and you’ve had plenty of girlfriends, aren’t I just some raggedy old Playboy magazine buried in the back of the closet?”

  “Don’t ever say that.” That serious tone of his replaces his playful flirty one. “You’re sexier than any of the girls in my college. Some things are just classic and they’ll stay that way, perfect forever.”

  What is he saying? I’m not just some passing fancy? Even if I’m not tight and fit like all those skinny little college chicks that paraded their firm little bodies in front of his face, enticing him with those young effortless figures?

  “Too bad you’re too young for me and I’m too old for you. I told you already, we’re no good together.”

  “I don’t think so at all. I think we’re perfect for each other.” His soft lips lightly brush my neck as his strong hands wrap around my waist, sliding slowly over my stomach. The sensation makes me jolt upright as his rough fingers trace the curve of my hips.

  His touch feels so good, so right, especially when I’ve been craving it since that night. I want him to go lower, to touch me where he shouldn’t. I want to part my legs so he can slip his hand in between and feel how wet I am, how much I want him.

  No! I can’t let this happen. I’m the adult. I take each of his hands in mine and place them to the side, holding them down on the seat. My hands look so small on top of his and if he didn’t let me, I’m sure I would never have been able to stop him.

  “No, Bobby. My body is off limits. We talked about this. I can’t do this to you. You have to find someone else. Someone your age.”

  “Why?”

  “You’re 21 and you have your whole life ahead of you. I’m basically done with mine. I mean, you’re the same age as my daughter for Christ’s’ sake. If you want someone like me, marry my daughter. She loves you.”

  “I don’t want your daughter or anyone else. I want you. I love you.”

  He’s lying to himself. I made a mistake going so far with him that night or any of the other nights. I didn’t mean to play around with his feelings, his heart.

  Yet even while I’m saying that, my body is melting into his.

  It has to be just puppy love. But the way he touches me was the furthest thing from puppy love.

  “Please. You don’t love me. It’s just an obsession.” I know that was the wrong thing to say as soon as I say it. His eyes turn black, narrowing.

  “Don’t tell me how I feel. You can keep doing whatever the hell it is you’re doing. Playing make believe like a little girl, trying to act like everything is back to normal. Denying yourself happiness when it’s staring you right in the face. Pretending as if your feelings don’t fucking exist. But don’t ever deny mine. Don’t fucking dismiss my love as if it’s some little boy’s crush.”

  “I’m sorry, Bobby.” The pain in his face stabs me directly in the heart and I can’t stand it for one more second.

  So I do what I told myself I wouldn’t, I reach up and kiss him, gently. Just lips, no tongue and nothing as sexual as that night. Just a mother kissing her boy. But I still have to push away with my hands to force my lips to let go of his. No matter how I want to think of him in my head, the way my body wants him is definitely not familial.

  “What’s wrong?” he asks, his face clear of the threatening storm.

  “I still — I don’t think we should — I just mean what we’re doing is a mistake.” He’ll be fine, he’s still young. I have to make him see that it’s better if he loved someone else.

  “And what is it that we’re doing?” He rips his hands away from underneath mine and forces my legs apart, his hands sliding up my thighs until he reaches that crook right next to my drenched panties covering my pulsing slit. “You know you want it just as much as I do.”

  I don’t resist. I can’t. He’s right. I do want this. He cups my overheated mound firmly before growling “And it looks like you still have a lot of life left down here.” I almost cum instantly, his voice tickling my ear, his palm pressing down on my engorged clit.

  Instinctively, I buck my hips, pushing my wet pussy hard against his hand, feeling the weight, the pressure on every single sensitive inch. I want him to pull aside my panties and jam his fingers deep inside my ready and willing slit. I want him to spread my lips wide and tease my clit with the soft head of his hard cock that’s throbbing between my ass.

  But he shouldn’t do this. He can’t. And I can’t let him. I watched him grow up, ever since he was five. He’s my son, and I don’t want to lose him if this doesn’t work out. If he can’t stop himself, I have to stop this for him. This is all for him. I’m not good enough for him.

  “STOP!” Somehow, with whatever willpower is left, I wrench his hand away from my burning pussy.

  “What is it Lisa?” Rob calls from the front. “Is it too uncomfortable back there?”

  “No, no. We’re fine. I just need a bathroom break.”

  “It’s only been 30 minutes! Geez mom, you must be getting old.” Ava pokes her head over the top of the box. Good thing all hands are off.

  But can she smell my lust hanging in the air, though? Can the Carters?

  “I remember not too long ago, you were the one who needed to stop first.”

  “Mommm!!” she cries. Looks like I’m safe. But what I know what I was doing is incredibly stupid and I’m lucky Ava didn’t peek right just a minute before.

  “It’s OK. I need some coffee anyways. There’s a 7-11 up ahead,” Rob informs us.

  CHAPTER 29

  BOBBY

  I fucked up. I feel like knocking all these shelves over, breaking every glass display case in the store, and punching the cashier.

  I fucked up so bad. I can’t believe what I just did. I basically raped her. How could I do that to the woman I loved? Does she hate me now? Maybe I still am the little boy she thinks I am, the boy who can’t control himself, who forces himself on vulnerable women.

  What the fuck is wrong with me?

  I had a plan and now it’s ruined. Forget making her mine. Would she even forgive me? But it was undeniable that I felt the dampness of her arousal through her panties. I bring my hand to my nose and smell it, the intense muskiness invades my nose, making my head dizzy with lust.

  Goddamn. Why is she so fucking sexy? That irresistible curvaceous body is why I couldn’t hold myself back. That plump ass felt so juicy on my lap, spilling over my legs. And those fucking tits. Just popping out of her dress, barely held back by her bra. I want to bury my still steel hard cock between those mountains.

  Ah, shit. I have to do something about this. Jeans barely kept the monster in check when it was down, and gym shorts do absolutely nothing when it was hard, the massive tent obvious to anyone who even looks in my direction. Good thing everyone else is busy.

  I dash into the men’s bathroom and lock the door. The front of my boxers is stained dark from Lisa’s ass grinding against it, the head of my cock sticky with precum she squeezed out of me.

  I try to recall the feeling of her squirming on my lap, the heat of her body, of her searing pussy on my hand. I start to slowly stroke my cock. Suddenly, I hear a moan. That wasn’t me. Then I hear another.

  It’s coming through the vents and I recognize the voice. It’s Lisa!

  She must be in the women’s bathroom next door and she’s definitely masturbating!

  The thought of her, legs splayed, pussy spread open, one hand on her clit, another on her titty, sends my cock into a frenzy. The head is purple and swollen, the veins popping, straining against the skin.

  Normally, it would be impossible to bust in a place like this alone. But imagining Lisa next door, her moaning encouraging my cum to rise and build, I’m ready to explode any second.

  “Oh, Bobby. When did you ge
t so big?” I hear her gasp. With her sweet words, I can’t hold myself back as I furiously pump my hand up and down the entire 12-inch length of my throbbing cock. My eyes close as I hear Ms. Howard moaning my name over and over.

  “Bobby, I need your cum. Cum in me, now. Cum inside me, Bobby. Please!” I slam my hand to the base of my twitching cock as thick white cum splashes all over the stall, covering the wall in dripping globs. I can still hear her purring as the last of her orgasm leaves her body and I squeeze the last of my cum from the tip of my cock.

  Maybe she isn’t as mad as I thought. Maybe I still have a chance to salvage this. To make her mine.

  CHAPTER 30

  LISA

  I stumble out of the car as soon as we pull up and rush to the bathroom. My head is still spinning from Bobby’s hand on my pussy, how he felt my wetness through the scant nylon panties.

  Just thinking of it makes my knees weak and I collapse gratefully onto the toilet. Immediately, I pull my panties down to find it drenched and my pussy spilling more of my lust by the second. One finger on my engorged clit sends waves of pleasure coursing through my body. I can’t last two and a half more hours like this. I have to deal with it.

  I start to gently rub the outer lips, the hood that can’t hide my swollen clit. It’s so sensitive I don’t dare touch it directly. Bobby’s spectacular body pops into my head and I can’t seem to get it out. I know I shouldn’t keep fantasizing about it, but this is an emergency.

  I think of his hand on me like in the car but this time massaging my wet pussy, preparing it to accept the size of his pulsing cock, manipulating my clit so the juices continue to trickle out. Then he slowly guides his thick shaft into me, the swollen head squeezing in between the open lips, splitting my tight, ripe pussy, untouched for years.

  Oh, if only he knew how much I want him. No matter what I do, I can’t stop his very direct assault. If he keeps coming on this strong, I know I have no chance. He’s going to take me whether I want it or not.