What My Mother’s Mature Friend Was Secretly Paying For

I never thought one of my mother’s boring get-togethers would stay etched in my memory forever. That Saturday, I had to go with her because she was walking around with her ankle bandaged after a bad step, and the gathering was at Roxana’s house, the wealthiest of her friends. Since it was far away, I played chauffeur and stayed there, enduring the heat while they drank wine and gossiped on the terrace.

Around four, the sun was unbearable. I saw that they were distracted and, unable to stand the sweltering heat, took off my T-shirt and jeans and got into the pool in my underwear. I swam for a while, loosening my muscles, and when I finished, I leaned against the stone edge with my back to the house, catching my breath.

I felt a presence behind me. I stood up sharply, and there she was—Roxana—watching me from the shade of the covered porch. I remained standing, dripping wet, and for the first time I felt that she was looking at me not as her friend’s son, but as a man. The wet fabric of my boxer briefs hid nothing: it clung to my cock, outlining all of it, and she made no effort to look away. On the contrary, she bit her lower lip as she followed every drop running down my abdomen until it disappeared into the soaked elastic.

Roxana looked imposing. She had the body of a woman nearing fifty that seemed deliberately sculpted: pronounced curves, firm legs, enormous tits spilling out of her neckline, and the air of an experienced lady who knew she commanded attention. She was wearing a silk dress that clung to her in a way that made my blood boil and my cock move by itself inside my wet boxer briefs.

“Well… it seems you’ve grown a lot more than I remembered,” she said in a deep, elegant voice, but one loaded with an intention that left me speechless. Her eyes were fixed shamelessly on the bulge between my legs. “And not just in height, from what I can see.”

Until that second, Roxana had been the woman who brought me sweets when I was a child. But seeing her there, running her gaze over my chest and looking down without the slightest embarrassment, sent respect straight to hell. I felt exposed, and at the same time I liked the way she devoured me with her eyes. My cock began swelling without permission, and the wet fabric betrayed it inch by inch.

“Hey,” she said, barely straightening her posture, though her eyes remained glued to my crotch a second longer than necessary. “Tomorrow my husband is leaving on a trip, and I have some trees in the back garden that need someone to work on them. Would you come help me at three? I’d pay you very well… better than you can imagine.”

“Of course, Mrs. Roxana… I’ll be there,” I replied, trying not to show how fast my heart was beating or how hard my cock was getting.

She gave me one last look—the kind that said the “work” in the garden was the least of her concerns—and turned back toward the terrace with a sway of her hips that made it clear tomorrow would be the beginning of something big.

***

The next day I arrived at exactly three. Roxana opened the door with a smile that said nothing and everything. She took me straight to the backyard, where the trees supposedly awaited me. The sun was beating down hard again.

“It’s far too hot for you to work dressed like that,” she said, leaning against the glass doorframe as she watched me. “Take off your shirt. I don’t want you ending up drenched in sweat.”

I didn’t make excuses. I pulled it off in one motion. I’ve always been thin, the kind of person whose muscles are well defined simply because he has so little body fat. Roxana made no attempt to hide her interest. She stayed there with a glass of iced tea in her hand, slowly looking me over as if she were taking my measurements. Her eyes traveled down my chest, paused on my abdomen, and inevitably ended at my waist, at the bulge already showing beneath the fabric.

I began moving some branches, feeling her gaze like fire on my back. Roxana didn’t leave. Instead, she came closer with a small towel and a bottle of cold water.

“Rest for a second. You’re going to get heatstroke,” she said, standing in front of me.

She was so close that I could smell her perfume mixed with the heat of her skin. She began drying the sweat from my chest with the towel, but she did it with a slowness that wasn’t normal. Her fingers brushed my skin “by accident,” and I felt my muscles tense beneath her touch. The towel moved slowly down my abdomen, and her knuckles grazed the waistband of my pants, right above my cock, already throbbing hard.

“You have very soft skin,” she murmured, lowering the towel to the edge of my pants. “You know… I like grateful people. And I think you and I could come to an arrangement that would make this ‘work’ much more enjoyable for both of us.”

She looked into my eyes with an intensity that left me dry-mouthed. This wasn’t a little girl’s invitation; it was the seduction of a woman who knew exactly what she was doing. She dropped the towel and placed her flat hand on my abdomen, then slid her fingers down until they brushed my bulge through the fabric. When she felt how hard I was, she drew a deep breath and smiled.

“Come inside,” she said in a commanding whisper, without taking her hand off my cock. “I have something for you in the living room. An advance for being such a good… worker.”

***

We went inside, and the air-conditioning struck my bare chest, giving me relief from the heat. Roxana walked with her usual elegance toward a glass table where a luxury box sat waiting. That nearly fifty-year-old body, with its perfectly rounded curves and the confidence of a woman with money, made me feel like a toy in her hands.

“Look what I have here,” she said, opening the box. “It’s for you. For coming to help this poor, lonely woman.”

Inside gleamed an expensive, heavy watch, the kind that made you look important. I looked at it and then at her, pretending not to understand where this was going.

“It’s incredible, Mrs. Roxana… but it’s too much,” I said, putting on my best innocent expression. “Pruning a few trees isn’t worth that much. I don’t know if I should accept it.”

She gave a little laugh and moved closer, enjoying my supposed confusion.

“Don’t be silly. I decide what things are worth,” she replied, circling me like a cat around its prey. “Besides, the work is only just beginning, don’t you think?”

She took out the watch and grabbed my wrist to put it on me. Her cool fingers lingered there for a moment. She ran her hands up my arms, tracing every muscle until she reached my shoulders.

“It fits you perfectly,” she whispered. “But I wonder whether such a well-behaved boy knows how to thank a lady when she’s being this generous.”

So much for playing innocent.

I grabbed her by the waist and pulled her against my body without warning. Roxana gasped in surprise, but she didn’t pull away. I looked straight into her eyes with a confidence that left her speechless, and kissed her. It was a kiss charged with all the lust that had built up since the pool, a deep, tongue-filled kiss, biting her lips and sucking her mouth until she was breathless. She responded immediately, tangling her hands in my hair and pressing her mature body against mine. I felt her enormous tits flatten against my bare chest and her belly rubbing shamelessly against my hard cock through the fabric.

We separated by barely an inch, both breathing hard.

“Tell me plainly, Roxana,” I said hoarsely, without releasing her. “Tell me what you want as thanks. No more talk about trees or watches.”

She laughed breathlessly, trying to recover the elegance I had just shattered.

“And where did the innocent boy from a moment ago go?” she asked with a mischievous spark in her eyes.

“He stayed outside with the trees,” I replied, squeezing her a little tighter. “I know exactly how to treat a mature woman like you. And I know you don’t settle for just anything.”

Roxana let out a genuine laugh, delighted. She felt victorious for having “corrupted” her friend’s son, but she was also turned on by my audacity. She lowered one hand and squeezed my cock through my pants, measuring it with her fingers, her mouth open.

“Well… the boy turned out smarter than I thought,” she said, running her tongue over her lips. “And much better endowed. I like that attitude. I like it a lot.”

Our lips met again in a deeper, wetter kiss. Roxana no longer walked elegantly; now she dragged me toward the stairs, eager to lock us in her bedroom, without letting go of my cock for even a second.

***

We entered the bedroom and she locked the door, but she no longer had her earlier composure. We stood facing each other beside an enormous bed that smelled of cleanliness and luxury.

“Take everything off,” she ordered, though she no longer sounded like a boss, but like a woman dying of desire. “I want to see every detail of the body that kept me awake all night.”

I took off my pants and remained in my boxer briefs, my cock outlined and hard, pushing the fabric outward. Roxana put one hand to her cleavage and drew a deep breath. She slipped her fingers beneath the waistband and slowly pulled my boxer briefs down, letting my cock spring out in front of her face. A moan escaped her when she saw it: thick, long, its swollen tip glistening from all the waiting.

“My God…” she murmured, touching her lips. “That thing is going to kill me.”

Because I was thin and defined, the muscles of my abdomen and thighs stood out like taut cords, and my cock looked even larger against my flat stomach. Roxana’s mouth hung open, hypnotized. She pulled down her dress and stood there in a black lace set that emphasized those curves of a woman in her prime: enormous tits spilling from her bra, a round, firm ass, and wide hips made for holding.

I no longer wanted her setting the pace. I grabbed her by the nape with one hand and by the waist with the other, kissed her nearly breathless, and with a firm movement let her fall onto the bed. Roxana landed on her back on the silk sheets, releasing a surprised moan that turned into pure pleasure when I threw myself on top of her.

I positioned myself between her legs and yanked off her bra. Her mature tits bounced free, heavy, their nipples already hard as stones. Without wasting a second, I buried myself in her chest, sucking one nipple hungrily while squeezing the other breast in my hand, kneading it without tenderness. I licked it in circles, tugged the nipple with my teeth, and left a trail of saliva across her cleavage. Roxana arched her back sharply, offering them to me even more.

“God, yes… suck them, suck them hard,” Roxana panted, completely forgetting her composure. “Don’t stop.”

She dug her nails into my shoulders, pulling me toward her, while her mature thighs squeezed my sides. Her hand desperately moved down to find me, and when she closed her fingers around my cock, she released a moan that trembled in her chest. She began jerking me slowly, measuring me, squeezing the tip, rubbing the fluid already dripping from me against the soaked lips of her pussy through her panties.

I ripped off her panties and slid two fingers between her thighs. She was so wet that she dripped into my palm. Her pussy was burning, tight, swollen. I rubbed her clitoris in circles with my thumb while pumping my fingers deep inside her, and Roxana writhed like a madwoman, mouth open, moaning soundlessly.

“You’re soaked, Roxana,” I said into her ear. “You’re completely wet for me, you filthy woman.”

“Yes… yes, because of you, because of that cock of yours,” she panted, biting her lips. “Put it in me now. Don’t make me wait any longer.”

But first I lowered my head. I spread her thighs wide and buried my tongue in her pussy, sucking up all her juices. I licked her labia slowly, nibbled them carefully, and then attacked her clitoris, sucking it like candy. Roxana cried out and grabbed my head with both hands, rubbing my face against her soaked pussy.

“Oh, oh, there… don’t stop, you bastard… right there,” she moaned uncontrollably, moving her hips against my mouth.

I pushed my tongue deep, pulled it out, and thrust it back in while squeezing her tits with my hands and pinching her nipples. I drove two fingers into her pussy while continuing to suck her clitoris, and felt her whole body tense. She came in my mouth screaming, squeezing my head between her thighs and soaking my face. I didn’t let her go; I kept sucking her clitoris until I left her trembling and panting, her legs spread and her pussy throbbing with pleasure.

***

Roxana couldn’t take it anymore. She pushed me slightly back, slid off the bed, and knelt on the carpet at waist level. She looked up at me with a devotion that made me feel like I owned the whole house.

“You have no idea how badly I’ve wanted this since I saw you getting out of the pool,” she murmured, gripping my cock with both hands.

When I was free in front of her face, her eyes lit up. She held me at the base with one hand, fondled my balls with the other, and stuck out her tongue to lick the tip slowly, savoring me and gathering the thin string of fluid dripping from me. Then she licked me from top to bottom, the entire shaft, as if I were an ice cream, coating my cock completely in saliva.

“What a delicious cock you have, you bastard…” she murmured, placing wet kisses on my glans. “It should be illegal for a guy your age to have one like that.”

She opened her mouth and took me in completely, sinking down halfway, using a technique that drew a growl from me that echoed through the room. She knew exactly where to press with her tongue and how to use her lips to make me tremble. She sucked me up and down, lips tight, as if her life depended on it. When she reached the base, I felt the tip touch her throat, and she didn’t even choke: she stayed there for a second, swallowing me, barely gagging, then rose again with a string of saliva hanging from her chin.

The thrill of having my mother’s best friend kneeling with my cock in her mouth, her enormous tits bouncing with every movement, made every muscle in my body tense. I put one hand on the back of her head and began setting the pace, pushing her face against my pelvis. She let me, moaning around my cock and looking up at me with tear-glazed eyes as her makeup began to run.

“That’s it, Roxana, suck it like that,” I growled. “Take it all the way down.”

She pulled my cock from her mouth, spit on it, jerked it quickly with both hands, and licked my balls one by one, taking them into her mouth and sucking them hungrily. Then she returned to my cock, swallowing it in one motion, and this time took me all the way to her throat, her nose pressed against my stomach.

“I knew you’d be worth it,” she said with glazed eyes and her mouth smeared with saliva before going back to work, faster now, determined to make this the best “thank-you” of her life.

She took one breast in her hand and rubbed it against the tip of my cock, wrapped it between both breasts, and began giving me a titfuck, squeezing them tightly and sucking the tip whenever it emerged. The sight of my cock sliding in and out between those two enormous mature breasts had me ready to explode.

I felt the pressure becoming too much for me to breathe. Roxana realized I was on the edge and, instead of slowing down, took me fully into her mouth again and sped up, cheeks hollowed, sucking me with all her strength while looking into my eyes from below. When there was no turning back, I let go. I shot the first burst down her throat and she didn’t move; the second filled her tongue; the third and fourth overflowed from the corners of her mouth. She didn’t pull away even an inch: she received every jet of cum while staring at me, swallowing and finishing what she had begun.

Even after there was nothing left, she kept sucking the tip for a while longer, savoring every last drop and milking me with her tongue. She stood slowly, wiped the corner of her mouth with one finger, and licked it while looking at me, my cum still shining on her lips and chin. She winked.

“Don’t worry about the watch; this was worth every penny,” she said, swallowing what remained in her mouth. “But I’m still hungry, and one round isn’t enough to satisfy me. That cock of yours will be hard again in a little while, right?”

***

She took off the last thing she was wearing and leaned against the edge of the bed with her back to me, offering me that mature woman’s ass with a clarity that left no room for doubt. She spread her cheeks with both hands, showing me her soaked pussy and tight asshole, moving her hips to tease me.

“Let’s see whether you’re still so cocky now that you’ve unloaded,” she challenged, looking over her shoulder. “Come fill me, bastard. I’m empty inside.”

My cock sprang hard again. I grabbed her by the hips, positioned her on her back in the middle of the bed, folded her legs against her chest, and plunged into her in one thrust, all the way to the hilt. Roxana let out a scream that must have vibrated throughout the house, closing her eyes and opening her mouth as I filled her completely. She was tight, with the heat of a mature woman that drove anyone crazy, and as soon as I felt the end, I began fucking her at a savage rhythm, thrusting all the way in and out while rubbing her clitoris with the base of my cock on every stroke.

“You’re so delicious, Roxana. What a delicious pussy you have,” I growled through my teeth as the bed creaked against the wall. “You’re soaking wet. I can hear you sloshing.”

“Yes, give it to me, give me all of it… don’t stop, bastard, don’t stop,” she moaned, her tits bouncing wildly with every thrust.

She wrapped her legs around my waist, hooking me to feel me deeper, releasing moans that no longer had anything of the elegant lady from the living room. She dug her nails into my back, sought my mouth to shove her tongue down my throat, and bit my neck. The thrill of fucking her in her own bed, on the sheets where her husband slept, with the watch she had just given me shining on my wrist as I grabbed and squeezed her tits, drove me to thrust harder and harder.

“Say it, Roxana,” I growled, driving all the way in and staying there while moving my hips in circles. “Tell me what a slut you are for coming with your friend’s son’s cock in your pussy.”

“I’m a slut, I’m a slut for you, bastard,” she moaned, red-hot with arousal. “Fuck me, fuck me like a slut. Give it to me all the way.”

I turned her over and put her on all fours at the edge of the mattress. That firm body of a woman nearing fifty waiting there for me, ass raised, pussy dripping, tits hanging down, was something else entirely. I grabbed her hair, wound it around my fist, pulled her head back, and thrust into her again with a hard stroke. The impact of my pelvis against her buttocks echoed through the room, and Roxana released a long moan as if it reached all the way to her soul.

“Harder, harder, don’t stop,” she moaned, burying her face in the pillows with her ass held high. “Break me open.”

I gave her everything I had, without mercy, watching her buttocks shake beneath my thrusts and the marks of my hands appear on her hips. I grabbed her waist and began slamming her against my cock, pulling out and driving in with all my strength, feeling her pussy tighten more and more. I slapped her hard on the ass, and Roxana moaned with pure pleasure.

“Again, again… hit me more,” she panted, arching her back.

I gave her two more slaps until her buttocks were red, without stopping fucking her. Then I lowered my thumb and rubbed her asshole with saliva and the juices dripping from her, pressing lightly while continuing to pound her pussy. Roxana howled and came again, trembling and squeezing my cock with spasms, soaking my balls with her fluid.

My “mother’s friend” no longer existed. There was only a mature woman kneeling there, surrendered and begging the thin young man to fuck her pussy until she burst. And I was giving it to her, without stopping, without mercy, listening to her moans grow louder and watching her juices spill down her thighs.

***

When I felt I couldn’t hold back any longer, I pulled out sharply. I forced her to kneel on the carpet in front of me, disheveled, makeup running, her tits bouncing from all the pounding, pussy dripping down her thighs, her gaze lost in pleasure.

“Enough games, Roxana,” I said, taking her by the chin and rubbing my wet cock across her lips. “Now open that slut mouth wide. Swallow the rest of the payment, so you can see that I took today’s work seriously.”

I placed the tip against her lips, and she didn’t hesitate: she opened her mouth, stuck out her tongue, and let me rest my cock on it. I began jerking off quickly in front of her face, gripping her hair with my other hand and forcing her to look at me. She licked her lips, eyes glassy, waiting.

“Here, here, give me all your milk,” she panted, sticking out her tongue farther and touching her tits. “Come in my mouth, bastard, on my tongue.”

I groaned and came in jets. The first spurts landed on her tongue and filled it completely; the next painted her lips, cheek, and nose, while a thick strand fell onto her mature breasts. She received it all with a wicked smile that branded itself into my memory, swallowing what she could and letting the rest drip from her chin. She wiped her face with her fingers and put them in her mouth one by one, sucking them clean while staring at me with complete shamelessness.

“You’re definitely the best ‘gardener’ I’ve ever hired,” she said, rising with the elegance she recovered in an instant, a trace of cum still shining between her breasts. “Get dressed and leave before my husband comes home. But keep the watch on… I want your mother to see it and die of envy without knowing who gave it to you.”

***

That same night, sprawled on my bed with my adrenaline still high, I left the watch on the nightstand. It gleamed beneath the lamp, and every time I looked at it I remembered her face kneeling on the floor, my cum dripping from her chin.

My phone vibrated. An unsaved number, but I knew perfectly well who it was.

“How’s that cock doing, gardener? You were very efficient today… but you left my bed a disaster, my pussy wrecked, and my perfume now smells like you and your cum. I can still feel you inside me. Start thinking of an excuse to give your mother so you can come back tomorrow, because you left me wanting to see what else you know how to do with that cock.”

Just as I was about to answer, I heard my mother walking down the hallway.

“Son, are you asleep yet? Roxana called to say you did an excellent job with her trees. She says you’re very thorough.”

I held back a laugh.

“Yes, boss… the sun was beating down, but she paid me well,” I replied while writing back: “Tomorrow at the same time, Roxana. And this time you won’t need to invite me inside. I’m going to fuck you against the first wall I find.”

***

Throughout the week, my phone never stopped vibrating. Roxana wasted no time: she sent me provocative photos taken from above—the tits squeezed into a lace bra, her pussy spread open with two fingers inside, her ass raised in the mirror—along with messages saying she couldn’t hold out until Thursday. I didn’t fall behind. I locked myself in my room and returned the favor in front of the mirror, my hard cock in my hand, showing off every muscle. It was a back-and-forth exchange of lust that sent the tension through the roof.

“You look delicious,” she would say in voice messages, with that husky voice that drove me wild. “You have no idea how much I miss that cock inside me. I’ve touched myself three times today thinking about how you fucked me. You’re going to leave me dry before you even arrive.”

By Thursday I couldn’t take it anymore. I had the key she’d given me “just in case,” and decided to show up an hour early, my lust at full throttle. I entered quietly, following the sounds coming from the master bedroom—muffled moans, the splashing of fingers in a wet pussy. When I slowly opened the door, I saw her sprawled across the bed, completely naked, legs spread wide, one hand between her tits squeezing her nipples, the other buried in her pussy with three fingers, moaning my name softly.

“You nearly scared me to death!” she shouted, jumping and covering herself with the sheet. “You said you were coming at four!”

I didn’t say a word. I pulled off my shirt, lowered my pants to my ankles, and threw myself onto her before she had time to react, my cock already hard as a rock. I ripped away the sheet and pinned her to the mattress with my body weight.

“I came to collect payment for every picture you sent me this week,” I whispered into her ear, biting her earlobe. “And every voice message. And all three times you said you touched yourself. You’re going to pay me for them one by one, slut.”

I buried myself in her chest, sucking one nipple while lowering a hand between her legs and finding her soaked, swollen, dripping. I thrust two fingers inside her, and she arched her back, giving me everything, forgetting her fright in an instant. I rubbed her clitoris with my thumb while continuing to suck her tits, and Roxana began trembling immediately.

“There, there… put it in me now. Don’t make me wait, bastard,” she moaned, digging her nails into my shoulders and grinding her pussy against my hand. “You had me desperate. You have no idea how much.”

I forced her legs apart, grabbed my cock, rubbed it over her soaked labia, coating the tip with her juices, and thrust back inside in one motion, so hard that the bed slammed against the wall. I began fucking her at a savage pace, deep thrusts making her whole body reverberate, her tits bouncing against my face. She was completely gone, babbling, punished for keeping me tempted all week.

“Oh God, oh God, yes, bastard, break me,” she moaned uncontrollably, mouth open, unable even to close her eyes.

I turned her over, put her on all fours, and pulled her arms back so her chest pressed against the mattress, her ass high in the air. She looked obscene like that, surrendered, her red pussy waiting for my cock. I thrust into her again and grabbed her wrists, riding her like a machine with all my strength.

“Take all of it, Roxana, all of it,” I said through my teeth, pulling her toward me to go even deeper. “This is for every picture, every voice message, every time you made me hard thinking about you.”

I released her wrists and grabbed her buttocks with both hands, spreading them apart and watching my cock slide in and out, shining and soaked in her juices. I ran my wet finger over her asshole and pressed slowly, and Roxana howled, began trembling, and came again, squeezing my cock in spasms that nearly made me explode.

“Don’t hold back, come inside me, come inside me, bastard,” she panted with her face pressed against the mattress. “Fill me completely.”

When I felt I couldn’t hold back any longer, I pulled out sharply. I knelt over her, grabbed my cock, and shot my entire load onto her back, long, thick streams painting her from the shoulder blades to her ass. Roxana collapsed face-first into the pillow, releasing one of those sighs that said I had left her floating in the clouds, cum dripping down her sides and staining the sheets.

“Damn you…” she whispered with a crooked smile, still trembling and rubbing my cum across her back with her hand. “You’re going to leave me too weak to have dinner with my husband.”

***

We lay there for a while, catching our breath as the smell of sex filled the room. Roxana looked at me like someone who had just discovered a treasure, her fingers idly playing with my cock, still hard and sticky.

“Listen carefully,” she said, stroking my abdomen. “This can’t be limited to a couple of days. My husband travels almost every Thursday. I want those days to be ours. Your mother will think you’re helping me with the garden or the accounts, and I’ll make sure you always leave with a little gift in your hand. Deal?”

“Deal, Roxana,” I replied, giving her a squeeze.

I got up to take a shower. I was beneath the cold water, relaxing my muscles, when I felt the curtain open. It was her, still naked, her skin shining beneath the droplets, her wet tits pointing at me. Without saying a word, she knelt beneath the spray and gripped my cock with both hands.

“One last thank-you before you go downstairs,” she murmured, and took me fully into her mouth.

She sucked me slowly beneath the water, squeezing my balls and licking the tip, pulling me out to lick the entire shaft before swallowing me again down to her throat. I looked down at her, hair plastered to her face, mouth full of my cock and eyes locked on mine, and felt my arousal rising again. I grabbed her head and began moving her face, slowly fucking her mouth and feeling the tip touch her throat again and again. When I couldn’t hold back, I came in her mouth for the second time that day, and she swallowed it all without losing a single drop, sucking me clean to the very last one.

As she polished me with the tip of her tongue, I thought Roxana’s Thursdays were going to be, by far, the best part of my week. And that my mother’s boring get-together had turned out to be the best business deal of my life.