A Boy for Hire
Copyright© 2025 by A Vulgar Man
Chapter 1
Erotica Sex Story: Chapter 1 - This is the story of young Jack, his first meeting with an older woman, Sadie and how she changed his life in a very unexpected way.
Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa Consensual Heterosexual Fiction
The call-in order came in a few minutes before midnight, just as we were about to close. The manager took the order and showed me the slip, his raised eyebrow asking me if I would deliver it on my way home. I grimaced and shook my head no. It had been very slow for a Friday night, mostly because nobody wants a hot meal on a swelteringly hot night like this one was.
I had been sweating my balls off all night long; the air conditioning couldn’t keep the kitchen cool in the face of the ninety degree night and the three big pizza ovens. All I wanted to do was get into the ancient car Mom shared with me and go home to the house where I lived with her. I couldn’t wait to take a cold shower and camp out in front of the air conditioner in the living room.
The manager covered the mouthpiece of the phone with his hand and said, “She knows that we’re about to close and the delivery guy is gone. She’s promising at least a ten dollar tip.”
That got my attention. The tips had been lousy all night what with business being so slow and like everyone else in this economy, Mom and I were struggling to keep our heads above water. I couldn’t afford to ignore a ten dollar tip.
I nodded yes and the manager handed me the slip. I quickly got the dinner ready, packaged it up and paid for it before I left. Paying for it now meant that the manager could cash out his drawer and I wouldn’t have to go through the bullshit of turning in the slip and paying for it when I came to work on Monday night.
I read the slip of paper taped to the bag and then looked at the address numbers on the mailboxes as I slowly passed them in the car. And there it was, one-thirty-one Dorset Street, five acres of well manicured grass fronting a very swanky McMansion. My heart sank as I saw that there were no lights on in the house.
I pulled into the driveway, killed the engine, grabbed the spaghetti dinner and climbed out of the car into the hot summer night. My radar was working overtime as I walked to the front door. This could be a setup for a robbery and although I only had about ten bucks on me, a potential robber couldn’t know that. They liked to call in to fast food joints and then rob the driver when he showed up.
I pressed the doorbell and stood with my back to the door, my ears cocked for the sound of feet on the gravel driveway or the rustle of bushes as a body brushed by them.
Nothing. No sounds from the night and no light or sound from the house. Great. I rang the bell again, really leaning on it this time in order to rouse anyone that may have fallen asleep waiting for me. Still nothing. I was pissed off now. Somebody had just cost me the price of a dinner and the gas and time it took to get it out here. I leaned on the doorbell one more time, then opened the screen door and hammered on the front door with my fist.
“You’re gonna break it down if you keep that up,” said a low, warm soprano voice from my left.
I looked towards the voice and saw the figure of a woman standing by the corner of the house, silhouetted against the glow of lights that had not been on a moment before. I stepped back and let the screen door hiss shut.
“Marco’s Pizza,” I said, struggling to keep my anger out of my voice. “Did you call in an order?”
“I did,” she replied. “Come on around to the backyard. Sorry I didn’t hear the doorbell, I was setting up at the pool.”
She vanished around the side of the house and I followed her. I turned the corner into the backyard and saw her waiting for me at the door of an enormous screen house that covered the swimming pool and the brick apron that surrounded it. The pool lights were on and there were several lit Tiki torches flanking it as well.
“Go through the door fast when I open it,” she said. “I don’t want to let in any more bugs than I have to.”
I nodded and she opened the screen door, slipped through it and I followed right on her heels, closing the door firmly behind myself. She led me over to a patio table and picked up a thin wad of money. I set the bag down on the table and she offered me the money.
“Here you go,” she said. “Keep the change.”
I fanned the bills and saw that it was fifty dollars. I looked up at the woman, now dimly lit by the lights as she said, “Think of it as an apology for forgetting to turn on a light.” She pushed the bag aside, picked up a glass pitcher beaded with condensation and asked, “Would you like something cold to drink? You look awfully hot.”
I wasn’t the only one that was hot; I could see that her upper lip and forehead were misted with tiny beads of sweat. I stuffed the money in my pocket and replied, “No thank you, ma’am. I’m heading home for a nice cold shower. Thank you for the offer and the great tip though.”
“Don’t be ridiculous,” she said. “Sweat is running off you in rivers. You can spare the time to sit down and cool off for a few minutes.”
“I guess you’re right,” I admitted. “I am pretty thirsty. I’ll have some water, if you’ve got it handy.”
“Coming right up,” she said. She set down the pitcher, rummaged around in an ice chest, took out a bottle of water and dumped it into a tall glass. She added a handful of ice from the cooler, the ice clinking against the sides of the glass as she picked it up and handed it to me. She filled her glass from the pitcher as I sat down and took a sip. It was ice cold and delicious.
I took a good sized swig, closing my eyes and moaning as the cold liquid flowed down my throat. I heard the snick of a lighter as she lit a pair of candles that were sitting on the table. I opened my eyes, seeing my hostess in good light for the first time. She smiled at me as she dropped the lighter and picked up her glass.
She was a short, white haired woman around five and a half feet tall. Her brief beach coat revealed a slim yet hearty figure. She had deep, round breasts over a slim waist, womanly hips and long, shapely and very lovely legs. Her hair was thick, short and shone in the dim light, covering her head in a cap of tight snow white curls. She had regular, even features, a small, upturned button nose and Cupid’s bow lips which widened into a grin that revealed her even white teeth when she smiled.
Judging by the lines around the base of her neck and the crows feet that framed her cobalt blue eyes, I figured her to be around thirty-five or forty years old. Nevertheless, her apparent age didn’t stop my dirty little mind from fantasizing about her. It had been a long twelve months since my first and only girlfriend had broken up with me, my hostess was hotter than hell and in a pretty damned skimpy outfit, and I was almost terminally horny.
She sank into a chair and frankly checked me out as she took a sip from her glass. What she saw was a six foot two inch, slim yet well muscled young man of sixteen with pale blue eyes, sun-bleached brown hair and skin tanned to a coffee and cream brown from a summer of sun at the beach.
“I’m Dana,” she said. “What’s your name?”
“Jack,” I replied. “Pleased to meet you.”
I drank the rest of the water and Dana asked, “Would you like more water or maybe some iced tea this time?”
“I don’t want to impose...”
“You’re not,” she said with a smile. “If you were, I wouldn’t offer. Here, try the iced tea. It’s quite good.”
She filled my glass from the pitcher just as a weak breeze sprang up. I didn’t even think before I leaned forward and stripped off my sweat soaked muscle tee, sighing in pleasure as the cool breeze caressed my chest. “Oh God,” I moaned, “Please don’t stop blowing on me!”
Dana laughed and I blushed scarlet as I realized what I had just done. “What a great little prayer!” she chuckled. “We can help Him out a little, if you’d like. Come with me.”
She stood up and walked over to a small bench that was next to the corner of the house. I picked up my glass and followed her, my eyes riveted to the flex and roll of her ass as she walked. She had, I decided, a world class ass. She turned and sank down on the bench, a small smile growing on her face as she caught me checking her out.
The breeze doubled in velocity as I passed the corner of the house. I stopped dead in my tracks and raised my arms, sighing, “Oh God, that feels good!”
“The whole back of the house catches the south wind and funnels it here,” Dana said with a smile. “Combined with the view, that makes this the best place to cool off on the whole property.”
“I would think that the swimming pool would be number one,” I said as I sat down.
“Well yeah, if you want to get wet,” she replied.
“If I had a swimming pool, I’d live in it in the summer.”
“They’re nice but they’re not that nice,” she laughed. “A small swimming pool like this one, the water gets too hot to enjoy it.”
“How hot is too hot?” I asked. The idea that a swimming pool could get too hot to enjoy was a concept that I hadn’t considered before. It made sense though; if the summer sun could warm Lake Champlain up to the mid seventies, a small pool like hers probably did get uncomfortably warm.
“The water was close to ninety this morning,” she replied. “It’s around seventy-two now. I had a half a ton of ice delivered this morning just to cool it off.”
“Wow!” I was impressed; cooling off a swimming pool with ice is something that I would never have thought of. I looked longingly at the pool. The breeze was nice but it was still hot. I began to rethink the cold shower idea, maybe a swim at Bare Ass beach was the way to go.
I drained my glass and stood up. “Thank you very much for the water and iced tea,” I said to her. “But I gotta get going. My air conditioner is calling me.” I walked back to the table and put my glass on it, then bent over and picked up my tee shirt.
I heard her glass clink against the table as she set it down and she said, “I was about to take a swim when you got here. Why don’t you join me?”
I gave her a quick look and opened my mouth to beg off when she said, “Please? I hate to swim alone.” There was a pleading look on her face, a look that I don’t think she knew was there. I hesitated for a long moment and her face became expressionless. “Well,” she said dully, “Suit yourself.”
She walked to the edge of the pool, untying the sash of her beach coat as she moved. She shrugged her shoulders and the terrycloth coat slid down her arms and pooled at her feet, leaving her as naked as the day she was born.
She dove into the water with hardly a ripple and glided underwater to the other end of the pool. She did a very nice racing turn and backstroked back to where I was standing, my jaw flapping in the breeze as I stared at her. She started treading water and looked up at me.
“If you’re not coming in, then you’d better go,” she said softly. “I don’t need an audience.” She kicked off the wall and swam to the other end of the pool again, her fabulous tits rolling from side to side as she backstroked across the pool. I gulped and fumbled with my belt, frantically trying to skin out of my shorts and underwear before she got back.
My cock was as hard as a rock by the time I dropped my shorts, kicked my sneakers off and plunged into the pool, diving in over her as she reached the wall and began to tread water. I dove deep and turned, opening my eyes underwater and staring at her lush body as she hung onto the side of the pool. I stayed down for as long as I could, imprinting the jutting mounds of her ripe tits and the gentle curves of her neatly trimmed mound and softly rounded belly on my brain.
I began to run out of air and kicked off the bottom of the pool, and that’s when it happened. The muscles in the calf of my left leg suddenly knotted as a powerful cramp hit me. The pain was excruciating, forcing me to double over in the water, futilely trying to work the knotted muscles into relaxation. I broke the surface and bellowed in agony, inhaling a mouthful of water as I thrashed around in the water.
Then I was in real trouble, gasping and choking, drowning just two or three strokes from the side of the pool. I felt a fist in my hair and I was suddenly being towed into shallow water. Dana towed me all the way over to the steps and made me sit down.
She grabbed my leg and lifted it, saying, “Point your toes like a ballerina and stretch that leg! Stretch it as much as you can!” Then her hands were on the knotted calf, pushing my leg even higher and firmly massaging the cramping muscle, her thumbs digging into it and helping it relax.
“Christ, that hurts!” I said between my clenched teeth.
She made me hold my leg as high as I could while she worked on the muscle. Gradually, it started to relax and the pain faded away, leaving an odd, tight feeling in my calf. Long before then however, I had begun to notice her big swaying breasts and now I had more than one muscle that had that tight feeling. I was regrowing my hard on right in front of her as she massaged my leg and there was absolutely no way that she was going to miss it after she finished working on me.
“How’s that feel?” she asked. “Is the cramp gone?”
“Yes ma’am, it seems to be,” I said. I could feel my face turning a flaming red as the moment I was dreading drew closer.
“No more swimming,” she ordered. “Get up and walk around on it, try to get it a little looser. I’ll get you something to drink. I think you cramped up because you’re dehydrated and short on electrolytes.” She let go of my leg and waded past me and up the stairs, hurrying to the house. “Start walking!” she said before she went inside. “Or it may come back.”
I got to my feet and hobbled up the stairs and out of the pool, grimacing as some minor pain flared in my calf again. I started walking around the pool, trying to think ugly and disgusting thoughts in an effort to get my cock to go down. But no matter how hard I tried, pictures of Dana’s lush, ripe body kept superimposing themselves on my brain.
I was on my second lap around the pool, heading away from the house when the rumble of the sliding glass patio door told me that she was back. I bit my tongue until tears came to my eyes, gamely trying to lose my erection but it was no good. I turned the corner around the far side of the pool and headed for the house and Dana, waiting for a scathing remark about my moral fiber or lack thereof.
She didn’t say a word. She looked but it was no more than a quick glance and then she handed me a big jug of Gatorade. “Drink all of it,” she told me. “It’ll help replenish the minerals and electrolytes that you sweated away today.”
I took a huge swig from the bottle and lowered it. “Keep walking until that leg feels normal,” she ordered. She sat down as I started on another lap of the pool. I was nonplussed by her attitude, to say the least, and more than a little relieved by it too. No awkward questions or comments meant no awkward answers from me.
I rounded the far end of the pool and there she was, still sitting at the table and still gloriously naked. I tried not to look at her but it was very hard to do.
“How’s it feel?” she asked as I approached the table.
“Good,” I replied.
“Does it feel normal?”
“Yeah, I think so.”
“C’mere,” she said, motioning me closer. She turned in her chair and patted her leg. “Put your foot here and let me see that calf.”
I mentally gritted my teeth and did as she asked, resting my foot on her firm thigh while she gently prodded my calf with her fingers. “The muscle feels relaxed,” she said. “I’d say it was ok. You can take your foot back now.”
I put my foot back on the ground and almost jumped out of my skin as she wrapped her hand around my cock. “It looks like you have another muscle that needs relaxing,” she smiled. “Why don’t I take care of that for you?” And then she leaned forward and sucked my cock deep into her mouth as her hands gently fondled my balls.
It felt like time stopped as Dana sucked my cock. She went after it like a starving woman, taking about half of me in her mouth, her cheeks hollowing as she sucked and her tongue doing wickedly pleasurable things to the head of my shaft. I did not last long at all. Just a few seconds after she starting to suck my cock, I stiffened and orgasmed, grunting as my semen pulsed into her hungrily sucking mouth.
She nursed on my rod until I finished cumming, her soft, cool fingers toying with my nuts as she made sure that she had every drop of my ball juice. She pulled back slowly, my cock coming out of her mouth with a small pop, smiling up at me as she delicately scooped up a wayward drop of my cum from the corner of her mouth with a finger and sucked it clean.
I sagged back against the table, my mouth hanging open in astonishment as she looked at my still hard cock, her smile widening. “I just love teenaged boys!” she laughed. She stood up and pressed herself against me, her body hot against mine as she pulled me down into a dizzying kiss, her tongue sliding into my mouth and finding mine as her hand caressed my cock and balls.
Our kiss broke and she got even closer to me, rubbing the plump mound of her sex on my thigh as she smiled up into my dazed eyes. “Would you like to fuck me now, Jack?” she asked, her hand still busy on my cock.
I nodded dumbly and she chuckled. “Are you a virgin, Jack?”
“N ... no!” I gasped.
“How many girls have you had this big, beautiful cock in?” she asked, wrapping her fingers around it and stroking it firmly.
“Just ... Just one,” I stammered.
She kissed my chest and turned away, heading for the door into the house and bringing me along with a firm grip on my still erect cock. The door rumbled open and we went into the chilled air of the house. Goose-bumps popped up on my skin as she led me through a couple of dimly lit rooms and into the master bedroom.
She touched a dimmer switch and a pair of lights flanking the biggest bed I’d ever seen came on. She let go of my cock and bounded onto the bed, laying back on a pile of pillows and smiling at me. She held out her hand and said seductively, “Come to me, Jack. I’m going to make every wet dream you’ve ever had come true.”
I moved towards the bed like a broken robot, still thunderstruck by the fact that this lovely mature woman had sucked me off and now wanted me to fuck her. I climbed onto the bed and sat on my heels, staring at her, my eyes drinking in the sight of her lush, ripe body as she lay in front of me.
“How many times have you fucked your little girlfriend, Jack?” she asked in a quiet voice.
“I ... I don’t know,” I whispered. “Fifteen or twenty, maybe. We broke up a couple of months ago.”
“How old was she when you first stuck that great big cock in her, Jack?” Dana asked in that same low voice, one hand drifting to her jutting breast and toying with the stiff nipple.
“Um, sixteen, I think,” I replied, watching in fascination as she caressed her own breast.
“How old were you?” she asked, her voice getting rougher. Her other hand was moving now, sliding down over her firm belly towards her widening thighs.
“I had just turned sixteen.”
“Did you get her cherry, Jack? Was she a virgin before you fucked your big cock into her?” Her voice was a hoarse whisper as she questioned me and I was almost speechless as I watched her cup her cunt in her hand, her middle finger sinking into her pussy through the thick labia that guarded it.
“Yeah,” I gasped. “Yeah, she was a virgin.” I had my cock in my hand now, slowly stroking it as I watched her masturbate.
“What else did you do to her, Jack?” she moaned. “Did she suck your cock for you? Hmm? Did you cum in her mouth like you came in mine? Did she drink your cum?” Her hips were moving now and I could hear the wet sound of her finger going in and out of her cunt.
“Yeah,” I groaned. “She loved suckin’ cock. She’d go down on me anytime I’d let her.”
Dana clenched her teeth and shivered, adding a second finger to her cunt as she jilled herself in front of me. “What else, Jack?” she gasped hotly. “What else did you do to your little virgin girlfriend? Did you cum on her little tits? Did you let that big cock of yours spew on her face?”
“She used to make me cum on her tits. She thought that would make ‘em bigger.” I was as aroused as I had ever been by that point. Dana was driving me crazy by getting off on hearing what Cindy and I had done together. I let go of my cock and practically jumped on her, getting between her wide-spread legs and groaning loudly as she grabbed my rod and positioned it at her cunt.
“Do it!” she cried, and I rammed my cock into her, burying it in her hot pussy right up to my balls as she wrapped her arms and legs around me. I went after her then, fucking her wildly as she bucked and thrashed under me, her big tits smashed flat against my chest as I lay on her and hammered my cock into her wet cunt.
She orgasmed almost as soon as I got my cock into her, her lush body stiffening under me and her eyes rolling back in her head as she climaxed fiercely on my rod. I braced myself up over her, grunting in pain as she dug her fingernails into my back while her cunt spasmed madly on me. She sobbed as her orgasm rolled through her and her juices flowed from her hyper-excited cunt as I rammed my cock into her spasming belly. Her orgasm went on and on and she frantically fucked me back, bucking against me as I buried my cock in her belly, again and again.
I grunted and clenched my teeth, desperately trying to hold back my cum and failed. My orgasm hit me like a bomb and I bellowed my completion as I rammed my cock as far into her as I could get it and held it there. Dana let out a thin, whistling scream as I flooded her belly with my hot jism, convulsed mightily under me and fainted, her hot, buttery cunt still working on my cock as I came.
I groaned and rolled off the motionless woman, resting for a moment in order to catch my breath and let my galloping heart slow down. I looked over at Dana and saw that she was still breathing, her big tits heaving as her unconscious body recovered from what had looked like a truly monstrous orgasm.
I debated with myself, trying to decide if I wanted to hang around for another shot at fucking this strange woman. At times she was almost scary, but she was one hell of a good fuck too, way more responsive and passionate than Cindy had been. The debate ended almost as fast as it had started. There was no way that I was going to leave as long as I had a chance of getting my cock into her hot pussy again.
I sat up on the bed and swayed as a wave of dizziness swept over me. I was thirstier than I could ever remember being and I knew that I was probably still dehydrated. I covered Dana up and left the bedroom, looking for the kitchen where I hoped that I would find another bottle of Gatorade.
I was leaning against the counter, looking around at the dimly lit kitchen in between gulps from a bottle of Gatorade. It was my second one in less than two minutes; I had guzzled the first one without stopping. I was thinking about going back outside and fetching the dinner that I had brought and putting it away when the kitchen lights came on, flooding the room in bright white light.
I looked over at the doorway, expecting to see Dana and froze as a woman I had never seen before came into the room. She was taller than Dana, around five feet, ten inches of extremely lovely woman. She had thick, honey blond hair that was shot through with white and was cut as short as Dana’s was. Her body looked hard and fit and she had a very nice rack on her; lush breasts that quivered freely under her blouse, capped with long, thick nipples that dimpled the material of her blouse. Her waist was tiny and her hips were delightfully slim, which helped to emphasize her firm, heart shaped little ass and the strong and shapely legs revealed by her mini-skirt. If I had to guess, I would have said that she was about twenty-five to thirty years old.
She was beautiful and only the horribly awkward situation that I suddenly found myself in kept my cock from rising up to salute her.
She stopped as she saw me and a look of resignation appeared on her face. “Oh shit!” she said, looking me up and down as I blushed fiercely under her gaze. Her eyes zeroed in on my wet and sticky cock and she asked, “Did you enjoy fucking my mother?” I stared at her in mortification and she snapped, “Well? Did you?”
I gulped and nodded as she grimaced. “How the fuck old are you anyway?” she asked.
“Sixteen, ma’am,” I replied in a weak voice. “I’ll be seventeen next month.”
“Oh son of a bitch!” she sighed, closing her eyes and shaking her head. She looked at me again and said, “I assume that’s your heap parked in my driveway?”
“Yes ma’am,” I nodded.
She sighed again and said, “Come with me.” I followed her out of the kitchen and down a hallway into a different wing of the house. She stopped in front of a door and gestured me through it, following me into the dark room and closing the door.
The lights came on and I found myself in another bedroom. I turned to look at her and she gave me a crooked smile. “How’d you like to make a hundred bucks?” she asked.
I blinked in surprise and looked at her in confusion. “What? How?”
“All you have to do is keep your mouth shut about what you did here tonight,” she replied, looking at me narrowly. “Can you do that?”
I nodded and laughed nervously. “Nobody would believe me anyway,” I said.
She dug into her purse and hauled out a roll of bills, peeled off five twenties and gave me a speculative look as I stared at her. Then she peeled off another five twenties and held the two hundred bucks up in front of my eyes.
“You wanna earn another hundred?” she asked quietly.
“What for?”
She didn’t answer as she dropped her bankroll back into her purse, set it down on the dresser and gave me another look. “Get on the bed,” she said, still holding the money up in front of my eyes. That was when the light went on in my head.
She was going to pay me to fuck her.
I gaped at her for a moment, stunned into immobility by the ridiculous situation. A beautiful woman with one of the best bodies that I had ever seen outside of a Playboy magazine centerfold was going to pay me to do something that I would have given my eyeteeth to do anyway.
“Well, go on!” she said.
I came out of my daze and hurried across the room, clambering onto the bed and laying back, watching her as she put the money down next to her purse and walked over to the foot of the bed.
“You ever say a word about this to anybody and I’ll find you and cut off your balls.” She delivered the threat casually while she unbuttoned her blouse and took it off.
“Who’d believe me?” I asked, my cock hardening as I watched her strip. Her skirt came off next and she gave me a proud smile when I gasped, “Jesus!”
She was a wet dream come true. Her belly was flat, firm and well muscled, as were her arms and legs. If nothing else, this woman was as fit as any woman could be. She wore a G-string slung low on her hips, the little triangular patch of material just barely covering the mound of her sex. Her breasts were cradled in a half cup bra and they were gorgeous, big firm melons that sat high on her chest, her thick nipples out for all the world to see.
She took the bra off and her tits swung free, dropping very little considering the size of them. Her fat nipples spiked in the cool air of the room. Her G-string came next, uncovering a patch of golden pubic hair, neatly trimmed into a heart shape around the tight lips of her pussy. She kicked off her high heels, climbed onto the bed and crawled towards me on her hands and knees, her lush tits swaying gently as she moved.
I spread my legs and she crawled in between them, her eyes fixed on my erect cock. “Jesus, Mary and Joseph!” she whispered in awe, “That’s the biggest fuckin’ cock I ever saw!” She wrapped her cool fingers around it and ducked her head, looking up at me as she licked a drop of precum off the head of my cock. “Mmm, yum!” she groaned.
She let go of my cock and moved up my body, straddling my hips, her wet pussy pressing against my rearing cock. She leaned over and dropped a rigid nipple into my mouth, hissing, “Suck it!” I cupped her tit in my hands and latched onto her nipple, sucking voraciously on it as my hands kneaded the firm meat of her tit. After a moment, I switched to her other tit, lashing that nipple with my tongue as I found and pinched the nipple I had just abandoned.
She lifted her ass and held my cock head against her labia, her ass bobbing and weaving as she began to work it into her tight cunt. “Oh fuck!” she groaned, sitting up and pulling her tits away from my face. “Where did a skinny little dork like you get such a big, beautiful cock?”
That was the wrong thing to say. I’d been taking shit for being slim for my whole life and it did nothing but get worse when I went into high school, where even the fucking girls were saying shit like that to me.