Son for Hire Ch. 01-11

Chapter 1

I sit in the plush leather seat of a long black car with tinted windows that I'd never been in before, sitting among dangerous people I'd never met before, driving through a neighborhood I'd never visited before, and nobody but my call girl sister had a clue as to where I was. To say I was nervous would be an understatement. Making matters worse I had 'first day on the job' butterflies in my stomach as these shady and dangerous criminals were my employer for the day.

"You've got your ID and medical report?" The stern faced woman named Diane sitting beside me in the back seat holds out her hand.

"Y-yeah." I rummage in my pocket and pull them out to give to her.

She looks over my clean bill of health then inspects my drivers license to verify my age. "Good." She hands them back. "If this trial run works out we'll need these tests done every month. We've got a guy or you can use your own doctor."

"Okay." I pocket the items. "Um...so Kiki was a little vague about how I get paid. Do you need my banking information or..."

Diane laughs. "I'm a pimp, not a fucking corporation. You get paid cash after each job." Her laughter fades as she gets deadly serious. "Never, NEVER, speak to the client about money matters yourself. I take care of all of that. You got that?"

"Y-y-yeah." I stammer and shrink down into my seat.

"Take it easy kid." The burly guy driving says. "You're with friends here." He peers back over his shoulder at Diane. "You sure he's ready for this?"

"What choice do I have?" She sighs. "It was today or we lose the client and I've got nobody else and nothing to lose. Any cock will do at this point." She was about to say more but just then a phone call comes in. She swears the moment she sees who it is and answers with an angry. "What now!?"

I was what you might call a 'pinch hitter' here. My sister's pimp had recently lost a few of her boys at the exact same time as pent up demand was reaching an all time high. With pandemic restrictions easing people were eager to return to their old lives again. I was aghast at the suggestion at first but over the course of a week Kiki slowly talked me into it. A going rate of a hundred bucks an hour to have sex, which I didn't get nearly as often as I would like, certainly helped my decision too. I was promised no gay stuff or hardcore bondage or anything outside of my comfort zone. When I expressed concern about my qualifications as a stud for hire Kiki just laughed and told me not to worry about it. She said there was a need for men of all types. The original plan was for me to start next week but I was woken up this morning with a call from a frantic Diane demanding that I start today. I agreed and was whisked away less than an hour later.

Feeling the rich leather of the seat against my hand and watching the big beautiful stone houses go by made it all feel a bit surreal for a dirt poor son of a whore like me. This was all so much nicer than I'd imagined. Mom was a junkie and a street walker right up to the day she left us and couldn't have set foot in such a place without been chased off. Even pretty young Kiki, who worked the downtown clubs, never talked about coming out into this swank section of the city. I had so many questions and if I wasn't so nervous I might have actually asked a few of them. Instead I sit there with a dry mouth, sweaty palms, and my heart hammering in my ears.

Before I knew it we were pulling into the driveway of a huge two story colonial style house, white with gray shingles, black shutters, and red brick at the foundation. Separated from the neighboring homes with high hedge borders the property around and behind the house was bigger than the whole block of low end apartments where I was raised and still lived to this day. Around the impeccable front yard was the classic white picket fence. It was the American dream made manifest.

"Shit!" Diane barks. "We're here already!? Hold on." She takes the phone from her ear as the person on the other end continues to talk. "Listen Danny..."

"Donny."

"Whatever! Listen, I know this is fucked up but we gotta go. Just go in there and make this bitch's dream come true. Just...I don't know, roll with it and do your best. Fuck the old bitch best you can, or do whatever it is she wants to do. I've heard this one's a bit weird. Just make her happy. Alright?"

"Roll with it? Best I can? What?"

"Try not to fuck it up but you'll get paid regardless. We'll be back at 4 pm sharp to pick you up. You got that?"

"Um..."

"This isn't how we usually do things but I don't have time to handhold you. It's sink or swim time Danny."

"But..."

"If things go South call me, but ONLY if you need to."

"I...uh..."

"He's not ready Diane." The driver says.

"Shut the fuck up Lamar. We're about to lose this bitch anyway, nothin to lose at this point. And we need to get back downtown like fucking yesterday." At her shoulder the voice on the other end of the line is screaming for her attention. With her free hand she pushes me toward the door. "Get going Danny, give'er hell."

"Jesus Christ." Lamar mutters, looking at me pityingly. "Good luck kid."

With Diane shoving at my shoulder I hesitantly open the door and step outside.

"OH!" Diane exclaims. "Shit. I forgot. She's your mother and you are her adult son. Just walk in and say 'Mom, I'm home.' then take it from there."

"Mom? Wait, what!?"

"Oh, and don't steal anything. Now close the fucking door!" Without waiting she leans across and pulls the door closed herself with a loud slam.

Not quite believing all of this was happening I stand stunned and watch the big black Cadillac back out of the driveway and disappear down the street. The next thing I knew I was standing alone in the quiet upper class neighborhood listening to bird song and the distance hum of a lawn mower. The trees, the gorgeous homes, the gardeners puttering around the vast lawns and colorful gardens, it was all like something out of a movie. I look down myself. I had worn my very best jeans and a collared shirt but out here it just looked sad and shabby.

The instinct to flee was strong. I didn't belong here. I didn't belong in this neighborhood and I certainly didn't belong in this job. I needed to get out of here. Although, Kiki had gone to bat for me getting this gig and it would be her that would have to suffer the consequences of me quiting and losing this client. I needed to talk to her first. I go reach for my phone...only to remember that it was in my jacket which I'd taken off in the warm car! I had been harried out so swiftly I'd forgotten all about it. Damn it!

In my panic I consider just running. Just running full out for as long as I could. Perhaps I could still catch Diane's car or maybe I'd just hoof it all the way home. I still had my wallet at least, maybe I could get to a pay phone and...and...shit. I didn't even have enough to my name to hire a ride back. The memory of my negative bank balance really brought focus to why I was here right now. It was cash and horniness that had tempted me into this predicament in the first place and, while I was far too frazzled to be horny, the need for green still beckoned just as loudly. I take a big deep breath and try to settle my nerves. Just do this Donny. Diane said I'd get my money no matter what. It was nearly one o'clock now and they would be back at four, three short hours would net me three hundred bucks. Kiki said tips were common as well. What did I have to lose?

I smooth my clothes and hair. Turning toward the looming house I swallow hard as I summon my courage and start toward the door.

I am about to reach for the doorbell when I remember Diane's instruction. I was supposed to pretend to be this woman's son? How weird was that! But the customer is always right as they say. If she were into vanilla sex she probably wouldn't have to hire a man to satisfy her needs. I put it out of my mind and focus on the job at hand. I try the door and find it unlocked. My heart beating like a jack rabbit's I slowly step inside the opulent entryway and close the door behind me. This place was SO NICE! Dark rich wood on the banister of the stairs I could see, real warm smooth hard wood floors, a vase of fresh cut flowers just down the hall, actual painted art on the walls, this was easily the nicest house I'd ever been in. Not only did it look great, it smelled fantastic! The aroma of fresh baking filled the air.

"Um...Mom, I'm...home?" I say out, much more meekly than I intended to. I was about to repeat myself when a woman appears at the other end of the hall. And what a woman!

She looked to be twenty years my senior, around her mid-forties, but she wore those extra years incredibly well. She wore a classic blue house dress, like something out of the 1950's, with a frilly white apron worn over the front. While heavy of bosom, wide of hip, and generally full of figure she maintained a wonderful hourglass shape. She was a tall woman, a bit taller than me, but not at all lanky or gangly in her build. Long flowing red hair cascaded down her shoulders, not quite graying yet but with lovely streaks fading a lighter orange here and there. Big, bright hazel eyes, plump lips, and the face of an angel rounded out her natural good looks. Wow! To put it bluntly, I had I simply had to be in the wrong house. To put it crassly, I was expecting either a hideous hag or an extra plus sized gal not a sizzling hot milf who had aged like a fine wine. A woman like this did not have to pay for sex.

"Theodore! My darling boy!" She prances down the hallway with grace of a ballerina. "You're late."

"Oh! Um...Theodore...that's me? That's me." I stumble over my words. "Yeah...um...sorry about that...they were running late you see...and...um...um...Diane had a..."

At the mention of my employer the woman's face flinches with irritation. I had done something wrong. In a stern voice she says. "I think you mean to say that your train was running behind." She leans into her words. "Your train from college. Yes?"

"Oh...yes. My train...from college...I'm Theodore from...train college...no...just normal college...oh geez...I'm messing this all up."

Her expression hardens as she plants her fists on her hips and leans her weight to one side. "You're new."

"I'm sorry."

"I paid for a professional." She says in clipped tone. "This wasn't cheap."

"I know...you see...Diane...my sister Kiki...I...last minute...um...it's my first...needed the money....you're my first...I'm not cut out...um...I should go...I need to go now. Oh God I messed it all up. I'm sorry!"

"Shhh. Hold on now." She says. She studies me a moment and her features soften again with warmth growing in her smooth voice. "Hold on. You came all this way. Let's just...slow this down. Okay?"

I swallow. "I'm...not a professional Ma'am. I'm just a broke guy from the city who needed a job. I've...I've never done this before." I hang my head. "I'm sorry."

She take my chin between her thumb and index finger and lifts my head to look at her again. "Hey, everyone has to start somewhere. Right?"

"Yeah." I say. "I guess so.

"I'd be your first, huh? Cute." She takes a good look at me up and down and smiles brightly. It seemed she liked what she saw. "I am willing to keep going if you are."

"Are...are you sure? I'll probably be really bad at this."

"I'm sure." Her eyes narrow suspiciously a moment. "Is this innocent rookie thing an act? If so...you are very good."

"Ma'am?" I tilt my head, confused by the question.

"Never mind." She chuckles and shakes her head. "Shall we start again?"

"I-if that's okay." I nod. "So...I'm Theodore?"

"Mmm." She tilts her head. "No, you don't look like a Theodore. Do you have a name you would prefer?"

"My name is Donny."

"Donny. Okay. I can work with that."

"And...what's your name?"

"Mom, just Mom."

"Got it." I say, starting feel a bit of confidence coming back to me. "I can do it."

"Yes you can Donny." She looks me in the eyes and I see real warmth and kindness in her glimmering hazel eyes. "You ready?"

I nod. "Ready."

***

Chapter 2

In the blink of an eye she is back into character. "Donald! My darling boy! You're late." She pulls me into a big motherly embrace and smooches my cheeks. As I feel her soft voluptuous body press into mine any second thoughts I had fly out the window.

I giggle. "Sorry Mom, my train was late."

She steps back, hands on my shoulders, and looks me up and down just like I were her son come back from months away. "You're so skinny! Are you looking after yourself out there?"

"I'm doing my best."

"You must be starving." She says. "Come on you, let's get you fed." She puts an arm around my shoulders and leads me down the hallway.

As I walk I notice the a grouping of family photos near the flower vase. What I see are pictures of a family of three. Husband, wife, and son. They had an adult son. So that's who I was standing in for. Interesting, and pretty fucking perverted. Ah, who cares? It takes all types to make a world. So she had fantasies about her son, who the hell was I to judge? The photos are just what one would expect to see yet...there was a distance in them. A coldness in the eyes of the three perfectly postured figures staring into the camera lens. From the outside it was the perfect family but these people in the photos were not happy. I take special note of the husband, being sure to memorize his features on the chance I happened upon him somewhere out here. Kiki had warned me that most clients were married so it wasn't a surprise though it was scary now that I was here. That dude looked pretty damn serious and pretty damn big.

I am brought into the kitchen and sat down in one of the tall chairs that lined the marble topped island. The area was even nicer than the entryway and hall. Big windows bathed the space in bright midday light. At an open window there sat an steaming pie cooling on the sill. It wasn't just like a fantasy, it was one. The woman's retro attire, the apron, the pie, this was all a part of the show. After her giving me a second chance I felt I owed it to the woman to live up to my end of this dream world. I do my best to imagine life in the shoes of an middle aged empty nester and I throw myself into the role I thought she wanted.

"What kind of pie?" I ask her as she busies herself at the fridge.

"Apple." She says happily. "It's..."

"My favorite!" I say, finishing her sentence for her.

She gives me an approving glance. "Yes, that's right."

"Thanks Ma, you're the best."

This stops her for a second. I watch as she takes a breath in and slowly lets it out. She spins, her arms full of food item and a huge smile on her face. "Learning quick." She quips.

"What ever do you mean?" I quip right back, way too innocently.

She laughs. "BLT okay?"

"Sounds amazing." I say. She couldn't have known but the truth was that I was famished. I hadn't time to get breakfast this morning. "Need any help?"

"Nope." She says, laying out the ingredients. "Mom's gonna feed her boy. You just sit there and keep me company."

"Gosh Ma, you're the best." I ham it up.

This was...AWESOME! I never had this in my childhood. Growing up Kiki and I more times than not had to take care of own meals. When our mother did 'cook' it was invariable something canned or frozen. When she did leave us the pair of us barely missed a beat. Kiki started turning tricks to pay rent and I picked up whatever work I could, but our home life carried on with minimal disruption. The view of this woman's full round ass as she cooked for me was just the cherry on top. But what a cherry! Damn! Older or not, this curvaceous red head had it goin on.

We chat about inanities as bacon is fried, tomatoes sliced, lettuce washed, homemade bread sliced and toasted, and fancy mayo and mustard dolloped. Neither of us probe this fictional scenario we were playing out too deeply as we talk about the things any mother and adult son might. Mostly I tell her about my classes and grades and school mates, all of made up on the spot, and she laps up every word.

With a crinkling crunch she slices through the crispy sandwich and plates with a big pickle. She places it front of me. Hunger getting the better of me, and not being well trained on my table manners to begin with, I scoop half of it off of the plate and chow down. "Oh my God this is so good." I say, crumbs tumbling from my lips. I catch her looking at me and stop mid chew. "Umm, was I supposed to say grace or something?"

She is smiling at me, a funny smile. Sort of proud and amused at the exact same time. She just shakes her head. "No, you're fine. Do you like the food?"

"Like it!? Oh my God, it is delicious." I gobble down another big bite. "Nobody cooks like you Mom. Mmmm!"

She brings a hand to her mouth and I swear I catch of glimmer of a tear in her eye before she blinks it away. "That's my boy." She whispers. "You...you always had a good appetite."

"Mmm!" I grin. "Only with your cooking Ma. You're the best. NOM!" Another huge bite and one half is polished off.

I eat and she watches, both of us happy as we could be. After a rough start things were going just swimmingly now. I was so glad I hadn't run away.

I polish off the sandwich with a loud belch and quickly cover mouth mouth. "Oh! Excuse me!"

She just laughs and waves her hand to let me know it was okay. Was that a hint of a blush on her fine cheeks? "A drink." She says as I finish off the pickle and wipe my mouth with a fancy cloth napkin. "You want a soda or a beer or juice? What you want my boy?"

A drinker I was not. I had experienced first hand the damage alcohol could do. "Soda please. Cola if we've got any."

She smirks as she catches the 'we'. "We do."

All I had done is eat a sandwich so far but I was starting to feel like I might be a natural at this. Thus far prostitution was nothing like imagined it was going to be.

"I hope you saved room for dessert."

"You know I did!" I grin from ear to ear.

Keeping up our back and forth I drink my soda as Mom takes the pie and slices a big fat piece out for me. A hearty scoop of super fancy vanilla flecked ice cream is heaped alongside. This too I eat with aplomb. No word of a lie, it is the best fucking pie I'd ever tasted and I let her know it by my groans of gluttonous bliss.

Leaning back in the chair I rub my full belly. "There's no place like home." I say, feeling very much like Dorothy lost in a magical land of fantasy. The difference being that my Oz had no wicked witches. "Oh Ma! So good."

"I'm glad you liked it." She grins before glancing up at the clock. I follow her eyes to see that it was 2:30. I had been here for an hour and half already!? Where did the time go? Cognizant of narrowing time together she says as casually as she can. "You must be all tight and tired after such long bath. Do you want Mom to draw you a bath?"

I got the message loud and clear. Foreplay was over. With me fed it and this scene of domestic heaven played out it was now time to feed her twisted mommy kink, and that was just fine by me. I just hoped I could live up to her expectations.

"Yeah. That train ride is a long one." I roll my shoulders and tilt my neck. Without even being asked she hurries around to start to massage my tense muscles. I close my eyes as my tight shoulders melt under her skilled hands. "Ohhh, yessss." I sigh as she rubs, her fingers kneading deep yet somehow still gentle, and I feel her breasts, through dress and apron, press into my shoulder blades.

"A nice hot bath would fix you right up." She whispers into my ear. "Let you...relax."

"A bath would be real nice Mom."

"Anything for my good boy."

Good boy? She called me a good boy! Ohhhh! Oh that was nice. That was VERY nice.