Jake's New Mommy Ch. 01

I walked for hours before coming to an empty playground, shivering from the cold night air.

It was stupid to run away from home without so much as a jacket, but here I was. You would think that I'd have learned my lesson, considering how often I fought with my parents. Once again I'd left the house with nothing more than a t-shirt, shorts, and sneakers. I hadn't even remembered to charge my cell phone.

I sat at the steps of the rusted jungle gym, hugging myself to keep warm. The neighborhood was nothing like the bright green lawns and two-storied houses I was used to. The buildings here were high-rises, tall and rectangular, and lacking all personality. Somewhere in the distance, I heard a train roaring down its tracks, making everything feel hollow and lonely. This was a working-class neighborhood, I realized, a world of difference compared to the gated communities grew up in.

When I felt the drizzle of rain tickling my arms, I almost broke down and cried.

What am I doing here?

Empty of anger, I wanted nothing more than to get up and walk home. But it was the farthest I'd ever run away. I was lost and exhausted, and scared. My phone was dead, and I couldn't remember seeing any coffee shops or fast-food restaurants for miles along the way. Not that I had remembered to bring my charger.

"Fuck!" I said, wishing I had the energy to punch something.

"Hey, you lost or something?"

I wiped my tears, surprised. There was an ugly middle-aged man on the opposite side of the playground fence. He wore cheap dirty clothes and carried a lit cigarette. My heart raced at the sight of him. Was he planning on robbing me, or worse? I was a already senior in high school but remembered all too well my mother's warnings about talking to strangers.

"No, I'm totally fine," I called back, trying my best to sound chipper. "Just having a rough night."

The man shrugged and walked off. "Suit yourself."

The relief I felt by the stranger's departure did not last long. The drizzle grew into a light rain, and I came to regret my decision to send him away. I should have asked for directions at least. My feet hurt badly, and my t-shirt was getting soaked. Suddenly it hit me, how bad of a situation I was in.

I was cold. I was hungry. I had nowhere to sleep.

I wondered if my family even cared I was gone. I doubted it.

Thunder pealed, and rain began to pour. My body broke into shivers. I buried my face in my hands, wanting to disappear. I was fucked. I was good and truly fucked.

I flinched at the sound of an umbrella opening. The pitter-patter of raindrops on thin polyester. Had that ugly man come back to help me?

"You're fixing to catch a cold, sitting in the rain like that," a soft voice said. A woman's voice.

I tried to wipe my face, but my arms were dripping. It was embarrassing to be seen crying, especially by a girl. The guys at school always teased me for being smaller than them, so I tried my hardest to come off as tough and mean. A lot of good that did me now. At least the rain would hide my tears.

Holding the umbrella was a startlingly tall and sophisticated-looking woman. She wore a belted beige overcoat like a character from one of those old crime films my dad loved so much. The belt accentuated her thin waist, huge breasts, and flared hips. To call her voluptuous would have been an understatement. Bright red lipstick colored her smile, but it was difficult to make out her face in the dark.

"Thanks," I said, staring at her red high heels. From her shoes alone I could tell she was beautiful.

"Come on, let's get you somewhere dry," she said sweetly.

The situation was so unexpected that I didn't know how to react. "I can't. I mean, I shouldn't--"

The woman rested a gloved hand on my shoulder. "I'm not going to leave you sitting here in the rain. Now move your butt, silly boy."

Maybe it was the shit situation I found myself in, but her simple touch felt wonderful. "Okay."

The woman's height was startling. She had to have been at least six inches taller than me. She wrapped an arm around my waist as we walked through the playground. I leaned against her, feeling her warmth through her raincoat, all six feet of her pressing against my quivering body. Despite the cold wet wind, I could smell her sweet floral perfume. I had no idea what her face looked like, but there was no doubt in my mind she was gorgeous.

Arms at my sides, I followed her obediently until we came to an expensive luxury car parked nearby. The engine was running. She opened the passenger side door, holding the umbrella to keep me dry. She squeezed my upper arm as I slipped into the car, as if to steady me.

I blushed. The gesture was a little emasculating, but there was something comforting about how much care she took with me. "Thanks."

Red lips smiling, the woman tucked into the driver's side seat, wiggling her large ass to get comfortable. My heart raced when I saw her face. A few slight wrinkles suggested she was in her late thirties, but she was stunning nevertheless. A real classic beauty. Deep green eyes and expensive auburn hair. A narrow nose and plush lips. She looked surprisingly pleased with the situation, too.

Slipping off her glove, she squeezed my hand. "Let's get you home, sweetie. What's your name?"

"Jake," I introduced myself.

She gave me a funny look. "You don't look like a Jake."

I chuckled politely. Okay, maybe she was a little crazy. But being in the warm car of a crazy beautiful woman was better than being stranded in the rain.

"Where are you from, young man?"

I hesitated to answer, and felt stupid for it. How was she supposed to drive me home if I didn't tell her where I lived? "Galewood Heights, near uptown."

"The suburbs?" The woman gave my hand another squeeze as she put the car into drive, starting down the road. "What are you doing out here? You're so far from home!"

"I went out for a walk. I guess I got a little lost." She began idly stroking my hand. making it difficult to keep my thoughts straight. "Um, do you have a charging cable for my phone?"

"Sorry sweetie, I don't have one."

I glanced at the USB ports in her car's dashboard, feeling uneasy. "Can I use your phone to make a call? I just wanted to let my mom know I'm on the way home."

The woman smirked. "Aren't you a little old to be a mama's boy?"

The casual remark put nerves in my stomach. Mostly because she was right.

"It's not a big deal if I call her or not," I said, trying to sound nonchalant.

"I'm afraid you don't have a choice, hon. My phone's dead too."

I noticed the car's GPS was off. Did she know how to get to Galewood Heights all on her own?

We drove for a while in silence. All of my attention was on the woman's hand, her soft fingers fondling my knuckles, my wrist, my palm. It was like she was getting to know me by touch alone. Then her fingers slipped from my hand onto my thigh. I kept myself perfectly still, aside from my heavy breathing. Her nails were painted a seductive crimson red. It amazed me that only a layer of wet cotton and a few short inches separated those sexy fingers from my crotch.

Despite my wet clothes, I felt my cock stiffen.

Shame colored my cheeks. I wasn't the sort of guy who met up with strange women for sexual encounters. I was still a virgin, and, if I'm being completely honest, not exactly the most popular guy at my school. Most of my friends had got laid by now, and they sure let me know about it, turning my life into a carousel of jealousy and frustration.

Now I had a gorgeous older woman coming onto me. And she was far hotter than any of the girls at school!

So I sat there, saying nothing, not moving a goddamn inch, cherishing the fact that her hand was close to my cock. The last thing I wanted was to ruin the moment. My cock was making a tent of my wet shorts, and I wasn't sure if I wanted her to notice or not.

"You're shivering," she said, pouting. "We need to get these wet clothes off of you right away."

"It's no big deal," I stammered, heart racing. "I'll be fine once I get home."

"Nonsense. It's a long drive ahead of us and I won't have you getting sick. Or ruining the upholstery. There's a blanket in the bag behind the seat. Come on, move that bum. No woman likes an idle boy."

"You want me to change right now?"

The woman squeezed my thigh. A jolt of pleasure ran through me, and my legs parted slightly. Holy shit. The farthest I had gone with the girls at school was a little heavy petting, and my body had never reacted so... intensely.

"There's no need to be shy. Trust me, I've seen it all. Here's an idea. If it makes it easier for you, just think of me as your new mommy!"

My expectations shattered like broken glass. The disappointment was enough to make my cock soften. I must have been losing my mind to think the random M.I.L.F. was coming onto me, hand on my thigh or not.

"You don't need Mommy to pull over and change your clothes for you, do you?" teased the woman. Somehow, she managed to sound both condescending and sweet at the same time.

"I can take off my own clothes."

"That's a good boy."

My cock throbbed at her words. Why did it feel so good to be called that?

I reached behind the seat, hating myself for being so skinny and short. I didn't want her to think of me as a good boy. I wanted her to see me as a man. A confident, powerful man who was worthy of a good fuck. I toyed with the idea of telling her we should go to her place instead, but I couldn't find the guts to voice what I really wanted.

"I'm going to change now," I said nervously.

"Go on." She gave me a quick wink. "Mommy won't peek."

I peeled my t-shirt off first, shucking it into my lap. My skin was cold and tender, and my nipples were hard. I thought I caught a flash of the woman's emerald eyes, but chalked it up to my imagination. Then my shorts went to my ankles, and I kicked them off with my shoes. The warmth of the heater touched my skin, and I shivered from the gooseflesh spreading across my body.

I felt the car come to a stop. We were at a red light in a neighborhood I didn't recognize. The buildings were small and far apart and crummy looking. Where in the hell was she taking me?

"Oh, you're absolutely soaked! Here, let mommy clean you up. Arms at your sides, little man."

The woman leaned over with a handkerchief and began to wipe my neck, my shoulders, my arms. I inhaled her flowery scent as she rubbed the silky fabric over my back and chest. When her fingernails glided across my nipple, a gasp escaped my lips, and I felt my crotch tingle. If the woman noticed my arousal, she didn't show it. She worked the handkerchief down my stomach and sides, then dabbed the moisture from my thighs.

She tugged the waistband of my boxers. "Come on, these need to come off too."

My hands reflexively moved to my crotch. It was pathetic, covering myself like an embarrassed loser in front of a beautiful older woman. Something about her attitude destroyed all the confidence I'd spent so long trying to build. In front of the strange woman, I could barely think of myself as a man.

"You want me to get naked?"

"Was I not clear the first time? We can't have you getting sick." Sighing, fished into the bag and retrieved the blanket, throwing it across my lap. "If you're going to behave like a brat, I'll treat you like one. Now will you remove those undergarments, or do you need me to do it for you?"

"I'll do it," I choked out. Her tone was getting harsher, making me feel small and pathetic. In fact, she didn't sound that much different from my real mom. As much I wanted to fuck this woman, I wanted to run away from her too. The conflicting emotions muddled my thoughts. What if she had liked me at first, but changed her mind once she realized the kind of guy I was? The thought of spoiling my chances with such a woman filled me with deep regret. A regret I'd carry for the rest of my life.

Trying to come off as confident, I pulled down my boxers swiftly. Then I was totally nude, save for the blanket covering my lap.

"You might want to cover up, hon," said the woman, smiling. "Unless you want the police to pull us over and see your little friend down there."

Little friend. Little fucking friend.

I draped the blanket over my nude body, wishing I could cover my face too.

"You never told me what your name was," I said, trying to bring some sense of normalcy back to our conversation.

"You can just call me Mommy." She gave a throaty laugh, and her laugher was deep and sexy. "Wouldn't that be precious?"

I forced myself to laugh with her. Then I remembered a video my friend, Pedro, who also struggled with girls, had shared with me. What the woman was doing was commonly referred to as a 'shit test.' The dating expert in the video explained that a man has to pass these shit tests by maintaining his composure and not allowing himself to get flustered.

I quietly replied, "How about I call you sexy instead?"

'Mommy' slammed the brakes, nearly sending into the glove compartment. She pulled the car to the side of the road with a screeching halt. Panting heavily, I realized we were beside a wooded area. I had been so distracted by all my lust that I hadn't noticed us leaving the city.

"Get out of the car," she said.

"What?"

Lowering the window, she reached for my clothes between my legs and tossed them outside. I reached out the window after them, watching my meager possessions disappear into the dark.

"What the hell did you do that for!"

The woman reached over and pinched my ear. "I have no tolerance for misogynistic boys. If you're going to use that sort of language, you can use it away from me. Now go."

The car's headlights illuminated the rain-slick road, beyond the light was pitch black nothingness. Checking the rear-view mirror, the other direction didn't look much brighter. It was so dark out that I could see the stars.

"You can't kick me out here!" I whined, wincing from the pain in my earlobe.

"You're a legal adult, aren't you Jake? A fully grown man?"

"Of course," I said.

"Then get out of my car and prove it to me." She let go of my ear. "A real man should be able to find his way home without the help of a woman, shouldn't he?"

I felt my temper rising. Being beautiful gave this giant bitch no right to speak to me this way! And she certainly had no right to lay a hand on me. I found myself gripping the car door handle. I was wearing nothing but a blanket and I had no idea where I was, but part of me was ready to prove myself to this woman, and the world, that I was a real man after all.

All I had to do was open the car door and step outside.

"It's time to make a decision, naughty boy. You can't sit there glaring at me all night. Either get out the car, get dressed, and start walking. Or you can apologize for your foul language and maybe, just maybe, you and your mommy can make up."

I almost threw open the door. I almost stepped out of the car to dig around for my wet clothes in the pitch-black darkness. I had run off a hundred times before, storming out of the house when my mom pissed me off, while the useless sack that I called father did nothing to help me. It would be a difficult journey home, but I was sure I could make it if I tried.

Yet something about this woman's domineering stare kept my ass in the car seat. Maybe it was those piercing green eyes. Those big red lips that I would have given anything to taste. I found myself staring directly at her. Her coat was open, revealing a tight navy dress with a deep neckline. Her cleavage was exposed. Her tits were large and buoyant and freckled.

Stepping out of the car would mean the end of my time with her. It would mean never seeing her again. That was far more terrifying than being trapped in the middle of nowhere. This woman, this experience... it wasn't something I was finished with yet.

I wanted to see where this went.

I wanted to prove to her I could be a man. Her man.

"I'm sorry," I said, forfeiting my pride.

"Are you going to be a good boy?"

"Yes."

"Yes, what?" She brought her face within inches of mine. I felt her breathing on my lips. "Go on."

"Yes... Mommy."

The woman made a delightful sound and threw her arms around my shoulders. The blanket slipped away. She pulled me close and I felt her tits against my bare chest. They were huge and soft and warm. Her nipples were thick and hard, and when they bumped into mine by accident I groaned into her neck, feeling my cock rise to full mast.

She pulled back a little, and then her lips were close to mine. I wanted to kiss her, to taste her. But Mommy was in control. She began pecking my cheeks with me soft, wet kisses, the sort a mother gives to her son. A few times they caught the corner of my mouth, and I felt the sticky coolness of her lips.

"I knew you'd make the right choice! I'm going to be the perfect mommy for you."

Almost bouncing with excitement, she set the car in drive and pulled back onto the road.

I sat there, stunned, just staring at the buxom beauty who sat a few feet away. Her breasts jiggled slightly with the bounce of the car. Her cleavage had a slight sheen, even after the car's courtesy lights went out. I was so mesmerized by the woman that it took me a while to remember she had thrown my stuff out the car window.

"Um, Mommy?" I said, a little scared to speak.

"Yes, precious?" Eyes on the road, she reached over to stroke my chin.

"We forgot..." I trailed off, distracted by her touch.

"Hmm?"

"We forgot to get my clothes. I think we've got to--I mean, can we go back and get them?"

"Oh no! I'm so sorry my little love! Your mommy made a big mistake. Don't you worry. I'm sure I have something at home you can wear. Thought it might not be the sort of clothes you're used to."

"But my phone was in my pocket," I said. "We have to go back and get it. We just have to."

"Silly boy," Mommy said, massaging my neck. "Do you honestly expect us to turn around and find the exact spot we pulled over, just so you can search around in the dark for your clothes?"

I leaned into her touch, feeling dizzy from the gentle squeezing she gave my neck. It almost felt possessive. "I guess you're right, Mommy."

"I'm always right." She slipped a hand under the blanket to squeeze my thigh. This time it was agonizingly close to my cock. I could even feel her fingernails tickling the hair of my balls. "At your age, boys have all sorts of hormones flowing through their silly little brains. It makes it hard for them to think straight. That's why you should appreciate how lucky you are to have a big strong mommy to do all the thinking for you."

As if to drive her point home, she moved her hand to my cock. I gasped as her warm, lotioned fingers encircled my stiff shaft.

"We still have to make up. Would you like that, Jake?" Her thumb fondled the head of my cock as she awaited my response.

My eyes went wide. So I wasn't delusional after all! This woman wanted me. She wanted my cock. Maybe I had just lucked out. Maybe I was her type or something. I wasn't sure what she saw in me. At that point, I didn't care. All I wanted was to slip my cock between those thick soft legs. I was going to lose my virginity, at long fucking last. Sure, I had to play along with her weird fantasies, but who could blame me? They weren't all that bad anyway.

Of course, I answered, "Yes, I want to make up with you, Mommy."

"My handsome little guy is a quick learner." Relaxing her grip, she started stroking me up and down, her fingers barely touching my cock. "Did you think I didn't know how to handle troubled boys like you?"

"I guess not," I said, rocking my hips a little. "You're so smart, Mommy."

To reward me, she made a tight fist at the bottom of my shaft, running her fingernails over my balls. Then she glided upward with a slow, loose stroke. By the time she got to the top, her fingertips barely traced the rim of my mushroom tip.