u/Apart-Alps8474

So, bit of context. My sis and I shared a room most of our lives bc our grandmother lived with us. Essentially, she occupied the bedroom that would have been one of ours (we lived in a three bedroom house). As we got older, my sister and I were use to just changing in front of each other. We would just overt our eyes, but obviously, we’d catch a glimpse of each other. No lie, I often checked out my sis’ butt when she’d bend over to pull up her underwear. She had a nice, hairy pussy. I often jacked off thinking of her tight body and C cup tits! I also became well-endowed, over time, and always wondered if my sister noticed?

So, fast forward and we’re having a sleep over. My best friend and her best friend are there. My buddy and I are actually younger than my sister and her friend. We decide to play “truth or dare” and things get spicy fast. My sister’s friend chooses me, and I chose dare. She keeps giggling uncontrollably, trying to form a complete sentence. Finally, she musters up the ability to say “I heard from your sister that you have a big dick! I wanna see!” My sister, overtaken with shock, slaps her shoulder and yells “JESSICA!?” To which her friend says “Well! Its true! You said it was big and ugly! I wanna see!”.

Jessica was super cute. I mean “Jennifer Love Hewitt” cute. So I figured why not? I stood up and pull out my fully erect dick. “Oh MY GAWD!!?? WHAT THE HELL!!??” Jessica exclaims, bursting into laughter. “Your little brother’s got a big dick!!” “SHUT UP JESSICA!” They continued to giggle like girls.

Now that the nudity threshold was crossed, we didn’t mind crossing that line. Next, my friend was asked to show his dick, which wasn’t as long as mine, but he had a nice thick mushroom head. Of course, the girls giggled about it and commented on its shape and how fat it was. My sister’s friend had pretty big tits, so we eventually dared her to show us her tits. They were a nice shape with big pink nipples and a wide areola area. Well, things got crazy when Jessica (my sister’s friend) dared my sister to touch MY dick. After some back and forth protests, my sister agreed to. It was odd bc she slowly approached it with her hand, like my dick was made of glass. She gently started petting it, like it was a dog. “That’s NOT how you touch a cock!” Her friend said, to which my sister answered something that I never knew: “Well, I’ve never touched one before! It’s my first time!”

As the game progressed, the dares included more nudity and sexual acts. I got to suck Jessica’s nipples, my friend sucked my sister’s, etc. But things reached another level when Jessica double dared me and my friend to show how we masturbate. We stood up, and started showing them. Both of us standing over them, beating our meat, fully turned on by the dare. My sister had a look of wonder, as her eyes were mainly fixed on my dick, as I stroked it to her. I have that image burned in my head. Her sitting on her knees in front of me, her face a few inches away from my dick, as I stroked my dick secretly thinking of fucking her in my mind. I could only imagine what she was thinking, as my older sister, watching her little brother (who now had a man’s dick) stroke it to her. I want to believe that she thought that her little brother’s dick would break her. I want to believe that, at that moment, she was intimidated by the size of my dick and knew that, if sex ever happened between us, her little brother would take the dominant “older sister” role from her.

“Wow! You guys must masturbate a lot! Yall are pretty good! Hehe!” Jessica said, taking my sister and I out of the moment we had. I ceased the opportunity, and said that my buddy and I were owed a “double dare” now. Jessica asked what we wanted, and I took the opportunity to say “I want you both to stroke our dicks, please.” Jessica laughed and didn’t care. She was always boy and sex crazy anyway. My sister looked reserved, but curious. My friend practically shoved his dick in Jessica’s face which, thankfully, left my sister for me (I wanted her anyway). I showed her how to place her hand on my dick, and showed her the motion to stroke me. Jessica had no problem stroking my friend (she obviously had experience). My sister looked over to Jessica, to watch her technique. “It’s kinda heavy!” I recall her telling me, as she continued stroking it. Jessica kept stroking my friend, bc she was in it for the “win”. So my sister, mirroring her, continued. My sister asked when do we stop. Jessica answered “when they ejaculate, of course!”. My buddy and I couldn’t last long, in those days. He came before me, to Jessica’s delight. My sister struggled with the technique, but was eager. Jessica and my buddy came over to watch, which turned me on more, helping me to finally ejaculate. My cum landed mainly on her hands and chest, but a bit landed on her cheek. She was startled by it.

It was a great experience, which opened the door for a few other sexual experiences with my sister.. 😭

​​im 21, and my mom is basically the final boss of charity work. her bff linda is 50 and she’s the sweetest, most humble human i’ve ever met. she’s just soft, kind, and genuinely pure. no clout chasing, just irl lo-fi woman. she has this way of making everyone feel seen, and her aura is just incredibly peaceful.

​lately we’ve been locked in on the grind for our ngo doing the most for the community. we’ve been running a judgment-free "free store" for families, prepping hundreds of warm meals for the shelter during the cold snap, and we even organized a massive back-to-school drive so every kid had a fresh start. we also spent a whole weekend planting a community garden and set up a pop-up pantry for seniors who can't get out to shop. it’s real-deal social service and it honestly feels amazing.

​last week we were at the warehouse till late sorting donations. it was just us two yapping while i did the heavy lifting. the "feel good" energy was peak. i’ve done a lot of work, but doing it with her hits different because she’s so genuine about it.

​at one point she looked at me and said, "you have such a good heart." it wasn't even weird, just a moment of real connection. she’s 50 and im 21, but we’re both just good humans trying to make the world suck less. she’s got this calm energy that makes me want to be a better person, no cap.

​i drove home feeling like i was on a cloud. it’s rare to find someone that real in a world that’s usually so fake.

i’m 21, and honestly, i was trying so hard to stay on that pure grind. i went about two weeks without touching myself.. just gym, social work, and trying to stay disciplined. but being 21 with a naturally high drive is a literal torture chamber sometimes. the pressure in my head was building up so much that i felt like i was actually going to explode.

​finally, i cracked. i sat down at 2 a.m., opened my laptop, and went straight to my favorite site. i didn't even look at the recommended stuff; i knew exactly what i was looking for. i typed in: bdsm

​i fapped that night, and it felt like a massive relief in the moment, but then i did it again the next day. and the next. now i’m stuck in this loop, just trying to drain the physical tension, but it feels like i can't get rid of it. no matter what i watch on the screen, my head is somewhere else entirely. the drive is just too high to handle right now.

then, it happened. i was scrolling through some random video, and this woman appeared who had the exact same vibe as linda. she had those same kind, humble eyes and that tall, frame. my brain literally glitched. i wasn't even watching the video anymore; i was back at the ngo office, watching linda reach for a stack of donation clipboards. the thought of her, this soft, good lady who spends her life helping people, being absolutely wrecked by a guy my age made me go feral. i gripped the edge of my desk, my breath coming in jagged gasps, and i let go. it was a literal lorry load of cum, just ropes of it, while i shook and whispered her name into the dark.

​after that, it wasn't just a crush. it was a total, 100% obsession. i couldn't even function around her normally. every time i saw her at the warehouse, i was scanning her like a milfyyyy. i’ve spent hundreds of hours yapping with her, but now every word was a test. ​linda is tall, and she’s got these long, thick built legs that look like they could hold a man down forever. and the 44dd boobies? they’re actual weapons.

she tries to hide them under those flowy charity shirts, but when she leans over to label a box of school supplies, i see the sheer weight of them, heavy, soft, and natural. i started obsessing over every inch of her. i noticed the way her shirt would sometimes pull up when she reached for a high shelf, revealing her midriff. she has this perfect, deep round navel that looks so soft against her tanned skin. and her ass? it’s a thick built dream, shaped like a heart and so soft i could practically feel it in my hands just by looking. ​we’d be standing there sorting through clothes for the homeless, and we’d have these feel good conversations that were killing me.

i was yapping non stop just to hear her voice:

me: "linda, you’ve been on your feet for six hours. sit down, i’ll finish the inventory."

linda: "you’re always so thoughtful, gfc. i don't know what i'd do without you."

me: "i just like making sure you’re taken care of."

linda: "your mom really raised a gentleman. you have such a servant's heart."

me: "maybe i just have a heart for you, linda."

linda: "oh stop it, you're going to make an old lady blush."

me: "you're not old, linda. you're just getting better."

linda: "is that a compliment? i'll take it."

me: "you should. you're the most beautiful woman in this building."

linda: "well, i'm the only woman in this building right now!"

me: "exactly. and i'm not complaining."

linda: "should we finish these food kits? the shelter needs them by five."

me: "don't worry about the time. i'm fast."

linda: "i've noticed. you have so much energy."

me: "it's easy to work hard when i'm working with you."

linda: "you always know exactly what to say, don't you?"

me: "i'm just being real with you."

linda: "it's refreshing. most boys your age are so... different."

me: "i'm not most boys, linda. i think you're starting to see that."

linda: "i think i am. you're very mature."

me: "mature enough to know what i want."

linda: "and what is it that you want?"

me: "just to see you happy. and maybe some coffee."

linda: "i can definitely help with the coffee."

me: "black, no sugar. like my soul, right?"

linda: "your soul isn't black. it's gold."

me: "if you say so. you see the best in everyone."

linda: "it's a gift. and a curse."

me: "i'll try not to let it be a curse for you."

linda: "i appreciate that. can you lift this crate?"

me: "for you? i'd lift the whole building."

linda: "my hero."

me: "don't call me that, i might start believing it."

linda: "you should. you're doing amazing work."

me: "we're a good team, linda."

linda: "the best. your mother is going to be so impressed."

me: "let's keep this our little secret for now. the progress we made."

linda: "our secret? i like the sound of that." me: "it has a nice ring to it."

linda: "it does. you're very charming today."

me: "it's the humidity. makes me honest."

linda: "honest is good. i like honest."

me: "good to know. because i've got a lot of honesty left."

linda: "i'm sure you do. let's get back to the school supplies."

me: "you lead the way. i'm right behind you."

linda: "i know you are. i can feel you watching me."

me: "just making sure you don't trip."

linda: "is that all?"

me: "for now."

​she’d laugh it off, thinking i was just being a sweet kid, but i was looking at the way her 44dds swayed when she laughed. i was planning. i was mapping out her body. i knew she wasn't that type, but the more she acted like a saint, the more i wanted to see her lose her mind. i wanted to take that humble, soft lady and turn her into a screaming mess. the obsession was practical now, i was just waiting for the one moment where the good human vibes would finally snap. ​i will fuck you bitch in mind..

am using all my intelligence for preparing a perfect plan to bang my l. there was no "map." there was just the fact that every time linda walked past me, i’d hold my breath. extremely horny and the drive is constant. it’s like a background noise that never stops. i’d be at the gym, doing whatever, and i’d catch myself thinking about her jackfruit sized boobies. she’s exactly my height. i’d imagine just turning her around and seeing if her hips actually fit in my hands.

​my "planning" was just me being a creep in my own head. i’d tell myself: "tomorrow, just don't act like her friend’s kid. don't smile when she makes a joke. just look at her." i knew the janitor left early on fridays. i knew the annex warehouse door had that heavy latch. i knew if we stayed late, we’d eventually be alone. i wasn't counting tiles; i was counting the minutes until everyone else left so i could see if i actually had the balls to do something. i was obsessing over the table in the back because it was the only place to sit..i tried something and failed it all.

i failed many times cause my balls were small for situations..

​failure 1:

we were looking for extra tape. the closet is tiny. i was right behind her. her hair smelled like that cuticura soap she uses. i reached out to put my hand on her side, but my heart was beating so fast i thought i was going to have a heart attack. i literally started sweating. i moved my hand back and pretended to be looking for a box on the floor. she didn't even notice. i felt like a total idiot.

​failure 2:

we were at the loading dock. i had this whole speech ready about how i couldn't stop thinking about her. i turned to her, and she had this really kind, tired look on her face. she said, "i'm so glad your mom suggested you volunteer here, gfc." it was like a slap. i couldn't say it. i couldn't be the guy who tries to hit on his mom’s best friend while she’s talking about how "good" i am. i just looked at the rain and felt pathetic.

​failure 3:

i sat on the edge of her desk while we were looking at the inventory. i was trying to look "mature" and "intense." i let my leg touch hers. i left it there for like thirty seconds, waiting for her to look at me. she just reached over me to grab a pen and said, "oops, sorry, i'm in your way." she didn't even feel it. she literally thought of me as a piece of furniture. i felt invisible and and left the chat..

​failure 4:

i actually walked to the annex door to lock it while she was in the back. i was going to make it this big moment. i touched the metal handle, and then i heard her laughing at something on her phone. she sounded so normal. so... not like a woman in a video. i realized if i locked that door and she wasn't into it, i was a coward. i let go of the handle like it was hot. i went to the bathroom and splashed water on my face, wondering why i was even doing this. ​i went home and lay on my bed for three hours, just staring at the wall.. i couldn't even make a move on a woman who was three feet away from me... 😭

next day: i decided that this is my last successful chance.. i don't fail here.. the warehouse was dead quiet except for the hum of the old refrigerator in the corner. we were standing by the big metal table where we usually sort the clothes for the shelter. the air was thick. it felt like it was hard to breathe.

linda: (pulling a long piece of clear tape across a box) that is the last of the school kits. my back is absolutely killing me tonight.

me: (leaning against the forklift, just watching her) you always overwork yourself.

linda: (she stops and wipes her forehead with the back of her hand) someone has to. these kids need their supplies by monday.

me: i know. but you have been here since eight am.

linda: (she looks at me and gives that tired sweet smile) you are still here too. you are a good man gfc. really.

me: (i don't smile back) stop saying that linda.

linda: (she looks confused and sets the tape gun down) stop saying what. that you are a good person.

me: yeah. just stop it.

linda: (she walks around the table and stands a few feet away) okay. you are being very strange tonight. did i do something to upset you.

me: no. you didn't do anything.

linda: then what is it. you have been staring at me like you are angry for the last hour.

me: i am not angry.

linda: then what is that look.

me: it is the look of someone who is tired of lying to himself.

linda: (she tilts her head and her hair falls over her shoulder) lying about what.

me: about why i am really here every night.

linda: you are here to help the community. you are here because you care.

me: (i take a step toward her) no. i am here because i can't stand being away from you.

linda: (she laughs a little nervous laugh) oh gfc. you are just sweet. you have a little crush on your moms friend. it is cute.

me: (i step closer until i am right in her space) it is not a crush linda. and it is definitely not cute.

linda: (the laugh dies out and she takes a half step back) okay. you are making me a little uncomfortable now.

me: i have been uncomfortable for a month. i have been in a literal torture chamber watching you move around this warehouse.

linda: (she looks at the door) i think we should go home. it is late

me: (i move and block her path to the door) i am not going anywhere until i say what i need to say.

linda: (her voice is shaking a little) gfc move out of the way.

me: no.

linda: (she looks me in the eyes and i see her pupils dilate) what do you want from me.

me: i want to bang you linda. i want to feel every inch of you.

linda: (she gasps and her hand goes to her throat) oh my god. you... you cannot speak to me like that.

me: i just did. i have spent two weeks without touching myself just thinking about this moment.

linda: (she is breathing fast now) i am your mothers best friend. i have known you since you were a child.

me: i am not a child anymore. look at me. i am twenty one. i am a man.

linda: (she looks down at my chest and then back up) you are being disrespectful.

me: i am being real. i have been mapping out your body in my head. i know exactly how those 44dds would look out of that shirt.

linda: (she lets out a shaky breath) stop it. please stop it.

me: why. because you don't like it. or because you do.

linda: (she shakes her head but she doesn't move) i am fifty years old. i am an old woman compared to you.

me: you are a woman. and you are the only thing i want. i want to see you lose that saint act.

linda: (she looks at the warehouse door and then back at me) someone is going to come in.

me: the door is locked linda. the janitor is gone. it is just us.

linda: (she moves her hand and touches the edge of the packing table to steady herself) my heart is beating so fast.

me: (i reach out and put my hand over her heart) i can feel it. it is slamming against your ribs.

linda: (she doesn't pull away) this is going to ruin everything.

me: i don't care about everything. i only care about this.

linda: (she looks up at me and her eyes are wet) i have been so lonely. nobody has looked at me like a woman in ten years.

me: i have been looking at you like a woman since the first day i walked in here.

linda: (she whispers) you really want me.

me: i want to bang you linda. i want to see you forget your own name.

linda: (she lets out a low moan and her head falls back) oh god.

me: (i grab her waist and pull her flush against me) say it. tell me you want it.

linda: (she looks over my shoulder at the long dark aisle of the warehouse, her hands still clutching my hoodie) gfc wait... is this... is this really a good place for this. we’re right in the open.

​me: it’s the best place. nobody is coming in here.

​linda: (she shifts on the metal table, the steel making a cold scraping sound under her) but the janitor... she’s usually here until late on wednesdays. i saw her cart earlier near the breakroom.

​me: she went home, linda. i saw her clock out and lock the side gate twenty minutes ago. we’re the only ones left.

​linda: (she bites her lip, looking toward the front of the building) but the door... i didn't hear it click. someone will see us from the street if they walk by. the door is open, isn't it.

​me: the door is shut. i locked the heavy latch and the deadbolt right after the last donation truck pulled out. i’ve been waiting for this all night..

me: (i stepped between her knees, spreading them wider until her thighs hit my hips. the heat coming off her was insane.) stop trying to cover yourself. put your hands down.

linda: (her hands were hovering over her chest, trying to hide the weight of her 44dds. she was shaking so hard her teeth were almost chattering.) i can’t. gfc, i feel so exposed. the light is too bright. look at me... i’m sagging, i’m old...

me: (i grabbed her wrists and pinned them to the metal table on either side of her hips. i leaned in until my nose brushed her neck.) you aren't old. you’re ripe. you’re heavy. i’ve been staring at these through your shirt for a year. let me see them move.

linda: (she let out a broken sob and arched her back, thrusting her chest forward. her nipples were dark and hard, reacting to the cold air.) then look. god, just look. i feel like i’m going to have a heart attack. my heart is beating so fast it hurts.

me: (i looked down. her stomach was soft, rising and falling with jagged breaths. her jeans were still around her ankles, trapping her legs. i reached down and gripped the waistband of her panties.) lift your hips.

linda: (she fumbled, trying to lift her heavy bottom off the steel, but her jeans were tangled.) i’m trying... i’m stuck... god, this is so messy. i’m so clumsy.

me: (i didn't wait. i yanked the fabric down. it snapped against her skin. i pulled them off one foot, then the other, throwing them into the dark.) i don't want neat. i want messy. open your legs wider.

linda: (she spread them as wide as the jeans would let her. the sight of her pussy hit me like a punch. it was mature, dark hair, glistening with wetness. she was soaking.) oh god... don't look at it like that.

me: (i reached out and touched her. just one finger sliding through the wetness. it was hot, slick, and slimy.) look at this. you’re dripping, linda. the saint is dripping all over the sorting table.

linda: (she squeezed her eyes shut and threw her head back, hitting the cardboard boxes behind her.) shut up! don't say that! i can’t help it... my body is just... reacting. i haven't been touched in so long.

me: (i rubbed my thumb over her clit. it was swollen. she bucked her hips, her heels banging against the metal table legs.) tell me how long.

linda: (she gasped, a sharp, whistling sound.) years... ten years... gfc, please... stop teasing... i need... i need it inside.

me: (i unbuckled my belt. the metal clinked loudly in the quiet warehouse. i shoved my jeans down just enough to free myself. i was rock hard, throbbing, leaking precum.) open your eyes. look at what you’re begging for.

linda: (she opened her eyes. they were glazed, wet, wild. she looked down at my cock and her breath hitched.) jesus... you’re so big. you’re so swollen. gfc, you’re going to hurt me. i haven't stretched in...

me: (i grabbed her hips, my fingers digging into the soft flesh of her waist.) you’ll stretch. you’re made for this.

linda: (she reached out, her hands trembling, and wrapped her fingers around my cock. her skin was cool, mine was burning.) it’s so heavy. it’s pulsing. i can feel your heartbeat in it.

me: (i batted her hands away.) don't touch. just take it. (i lined the tip up with her entrance. she was so wet it practically slid in the first inch on its own.)

linda: (she let out a low, guttural moan and bit her lip until it turned white.) oh... oh wow. just the tip is... it feels like fire.

me: (i didn't wait. i gripped her waist and drove forward. not slow. hard. i sank into her to the hilt in one motion.)

linda: (she screamed. it wasn't a word. it was a high, sharp cry that echoed off the corrugated metal roof. her body went rigid, her inner muscles clamping down on my cock like a vice.) fuck!

me: (i held still, buried deep inside her. the tightness was unbelievable. hot, wet velvet squeezing me from every side.) breathe. breathe, linda.

linda: (she was panting, short, panic-filled breaths. tears were streaming down her face.) it’s too much... it’s too big... i can feel you in my stomach... oh god, gfc... you’re filling every corner of me.

me: (i started to withdraw, pulling almost all the way out. the friction sound was loud—a wet schlick.) i’m not leaving. i’m just getting started.

linda: (she whimpered as i left her empty for a split second.) don't go... don't...

me: (i slammed back in. thwack. the sound of my hips hitting her heavy thighs was loud. the metal table screeched across the floor.)

linda: (her head snapped back. her 44dds bounced violently, hitting my chest with a heavy, soft thud.) yes! oh god, yes! do it again! wreck me!

me: (i found the rhythm. pull out. slam in. pull out. slam in. slap. squelch. screech. thud.) you like that? you like the 21-year-old drive?

linda: (she wrapped her thick legs around my waist, locking her ankles behind my back, pulling me deeper. she was clawing at my shoulders.) i love it! i love it! i’m a slut for it! make me feel it!

me: (i grabbed her tits. my hands sank into the soft, heavy flesh. i squeezed hard, twisting her nipples.) say it again. say what you are.

linda: (she was sobbing now, a messy, wrecked sound.) i’m a slut... i’m your mom’s slutty friend... oh god, gfc, you’re hitting the spot... right there... deeper!

me: (i picked up the pace. i was feral. the smell of sex and sweat was choking me. i was grunting, low animal sounds coming from my chest. i felt her pussy spasming, milking me.) i’m going to ruin you for anyone else. you know that!!

linda: (her eyes rolled back. she was drooling a little, her mouth hanging open.) ruin me... please ruin me... break me open... i don't want anyone else... just this... just this...

me: (i shifted my angle, grinding my pubic bone against her clit with every thrust. she screamed again, her body arching off the table.)

linda: i’m close! i’m close! don't stop! whatever you do, don't stop!

me: (i felt the pressure building in my balls. the "lorry load" was ready. i grabbed her throat—not hard enough to choke, just enough to hold her still.) cum for me. cum on my cock.

linda: (her pussy clamped down hard, fluttering wildly. she shook, her heels drumming on my back.) i’m cumming! gfc! oh god.

me: (i drove it in deep, bottoming out, and held it there. i exploded. hot, thick ropes of sperm shooting into her, filling her up, coating her insides. i roared, burying my face in her sweaty neck.)

linda: (she wailed, a long, dying sound, as she felt me pulsing inside her. she went limp, collapsing back onto the cold steel, her chest heaving, her legs twitching around my waist.)

me: (panting, sweat dripping off my nose onto her chest.) look at you. look at what i did to you.

linda: ahhh...you filled me... i can feel it... you filled me up.

me: (i stop her as she turns toward the loading dock door) wait. come here.

​linda: (she turns around, looking totally wrecked, her hair still messy and her shirt half-buttoned) gfc, i have to go. if i stay another second i’m going to collapse right here on the concrete.

​me: (i ignore her and step into her space. i reach inside her open shirt and grab both of her heavy 44dds. i don't cup them. i press them hard. i mean really hard. my fingers dig deep into the pale, soft skin, squeezing them together with actual force until she makes a sharp, wounded sound.)

​linda: (she winces, her breath hitching, but she pushes her chest into my hands instead of pulling away) ah... god... that’s so tight... you're bruising me...

​me: (i hold the pressure, staring her right in the eyes while i grind my thumbs into her flesh) feel that? that’s my mark. every time you hit a bump on the drive home, i want you to feel exactly how sore you are right there. i want you to feel my hands on you all night.

​linda: (she nods frantically, her eyes wet and wide) i will... i swear i will... i can feel it pulsing.. 😩

to be continued..