Milked by My Landlady

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Sometimes a guy just needs a helping hand.
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hewrite
hewrite
113 Followers

*Fuck.*

I hobble across the crowded Thai street, wincing as I go, moving like an old man as I clumsily maneuver between passing motorbikes and tutktuks. My thighs are beat to shit -- tonight was 'conditioning' class at my kickboxing gym, which means everyone gets to take turns kicking the fuck out of your legs. Going out for a few drinks afterwards may not have been the best idea, either, and now I'm tipsy and just trying to keep moving before I stiffen up and topple over.

I let out a loud sigh of relief upon reaching my apartment building, but it's cut short as I realize I'm still not quite in the clear; I live in an older place near one of the markets, and the only way up is a steep, narrow staircase.

*Goddammit*. Gritting my teeth, I get to it. Every step is agony, the way up a painstaking process. I'm forced to take a break only partway there, and I'm still leaning against the wall when a woman's voice filters up the stairwell behind me.

"Roger?? What are you doing??"

I turn to see my landlady, May, standing at the bottom of the steps. She's a pretty Thai woman of middle years, perhaps around 40, her wavy dark hair cut short and framing her finely-featured face.

"Oh, hey May," I manage a pained smile as she starts to ascend. I realize I'm in for it as soon as I see her expression -- she's not quite old enough to be my mother, but you wouldn't know it from the way she fusses.

"What are you doing, huh?" she asks again as she draws closer, eyeing me suspiciously. This isn't the first time she's found me a bit worse for wear after practice, and honestly it's kind of hard to keep shit from her. She seems able to see through my BS pretty easily; maybe that's the danger with older women.

"I'm just resting here a sec," I smile nonchalantly.

"Well let's go, huh? I can't get past you! Move!"

There's no helping it -- it's either go on up or get an earful. Grimacing, I try to lift a foot but goddamn is it difficult; my muscles are dead, it takes way too long to get myself moving.

May, meanwhile, is onto me right away.

"You're hurt again, aren't you?? Ugh! Stupid! Why you always doing this??"

She sets her groceries down and tugs my arm around her slim shoulders as I blurt out a series of half-hearted protests, but I know it's no use; once she's got her mind set on something she's gonna get her way, and that's all there is to it.

"I told you, you need a girlfriend so she can take care of you! Now you make me do everything!" she complains as she starts to help me up the stairs.

"You say it like it's so easy," I grunt in pain.

"It *is* easy! You are handsome, you have a nice job; you say hello and you buy some presents and then you have a girlfriend! Easy!"

I roll my eyes but don't say anything; I've yet to win an argument with her, and right now I'm just grateful for the assistance.

It's a tough trip but we manage to make it up to the second-floor after half a minute of huffing and puffing. As soon as we arrive on the landing, May takes a step back to look me up and down, ticking her tongue in annoyance.

"Ugh, look at you! Dirty! Why do you make me touch you for?"

I glance down and realize she's right; I haven't cleaned up since the gym and I'm caked with semi-dried sweat, my shorts and shirt crumpled and moist.

"Go take a shower!" she orders, stabbing a finger towards my apartment door down the hall.

"Err...yeah, okay. Sorry May. Thanks for the help," I say sheepishly. She's scarier than most of the guys in my gym; honestly, I'd rather go a couple hard rounds with my coach than piss her off.

I hobble away, using the wall for support and feeling a bit embarrassed, but I don't get more than a few steps before she's there again, pulling at my arm and placing it around herself.

"Come onn, you can barely walk," she sniffs, glaring up at me out of the corner of her eye. "Stupid. You shower and I get you dinner. Ok?"

I smile in surprise and she just shakes her head, muttering to herself in Thai.

It's been a year since I moved in, and in that time I've almost gotten used to her badgering and bullying. She's intimidating, for sure, but I'm a long way from home; it's nice to know someone's looking out for me, at least.

Even if she can be a bit much.

"You can shower? Or I have to do that for you, too?" she huffs as we stumble through my apartment door. She steps back to face me, quirking an eyebrow. If I didn't know better, I'd think she was flirting.

"No I'm...I can do that May, thanks," I laugh to cover my awkwardness. "And you don't have to get me any food, really...it's okay, I can manage."

She looks at me like I'm an imbecile.

"Roger. I know you can't cook. So what are you going to do? Go down and buy street food? Then I have to help you up again?"

She shakes her head and I can't help but chuckle -- she sees right through me alright.

"Okay, okay," I smile, holding my hands up in surrender. "You win. We'll do it your way. I...really do appreciate the help. Thanks, May."

"Yeah yeah," she says with the tiniest hint of a grin, shooing me off towards the bathroom. "I'll be back soon, okay? Go shower."

*

It's quite the clumsy ordeal getting myself cleaned up, but in the end it is so worth it. The hot water is a godsend; I'd gotten myself good and beat up, and I hadn't realized just how much I needed to rinse and relax.

I can't linger, though -- I've got to get some ice on my legs soon, or they're gonna be so swollen tomorrow.

I stumble awkwardly out of the shower, still toweling off as I exit the bathroom. I'm just wondering what to wear when a sudden motion catches my eye -- there's a woman standing at the stove in my kitchenette.

I curse and cover myself as she yelps and spins to stare at the burners, her pale neck burning a bright shade of scarlet.

"Oh sh...shit! Sorry May! I-I didn't know you'd be back so soon," I stammer, fervently wishing for some clothes within arm's reach. My place is just a small studio and I'm not used to company -- usually I get dressed at my closet on the opposite wall, but obviously tonight that's going to be an issue.

"It's...it's okay!" she exclaims, her gaze fixed on the food she's heating up, her cheeks a rosy pink.

"I'll just uhh, grab something real quick," I say, hurrying across the room, forgetting the state of my legs. I take one big step, try for another and end up tripping myself, tangled in the towel.

Before I know it I'm falling, landing loudly on the vinyl floor with a big bang.

"Roger!!" May shrieks, rushing over, her voice fraught with worry as she kneels beside me, tentatively touching my side. "What are you doing?! Are you okay, are you hurt?? Are you okay?? Ugh, why do you scare me!"

"I'm fine, I'm fine I'm fine," I grimace, pushing myself to a seated position. Thoroughly embarrassed, my first instinct is to brush her help aside -- but after trying and failing to get my legs working, I swallow what's left of my pride and take her hand. It's only with her assistance that I'm able to stand, the attempt made all the more awkward by having to hold the towel in place.

"You are sure you're ok?" she asks, brow furrowed in concern as she checks for injuries, one of her hands resting lightly on my stomach.

"Yeah I'm okay, I just...slipped."

She's still inspecting me when suddenly she freezes, her face turning even more red than before. I'm fit from fighting and nearly naked save for the towel, and it seems she suddenly becomes cognizant of that fact, as her hand makes an unconscious grasping motion across my abdomen. Her eyes go unfocused, her lower lip pulled between her teeth. It's slight and it's subtle and it only lasts a second, but in that moment she looks at me in a way I've never seen.

"Umm May I'm...fine..."

She comes to her senses and quickly takes a step back, jerking her hand away as her eyes widen at what she's shown. She recovers well though, the best way she knows how -- by going on the offensive.

"Sit!" she shouts, all fire and brimstone once more as she gestures violently towards the couch. "Go! Sit! Before you give me a heart attack!"

"But...but May, I'm--"

"Go! I bring you!"

There's no sense arguing with her so I hobble over to the couch, flustered; May seems to be in a similar state as she awkwardly tosses me the first clothes she sees, my sleeping shorts and tank top from off the bed. I don't have anything to wear underneath, but that's the last thing I want to tell her right now.

"Stay there, I bring you!" she growls, returning to the stove and furiously stirring something in the pot. "It's almost ready...don't move anymore!"

I do as I'm told, switching on the TV and getting dressed while her back's turned. I really hadn't expected her to be back so soon -- I thought she'd meant to cook something at her place and bring it over, rather than getting street food and heating it up here.

My mistake, I guess.

After a minute or two she comes over with a couple steaming bowls of soup and noodles. She doesn't let me help with anything -- bowls, spoons, chopsticks, napkins, beers -- she brings it all, and all I can do is watch helplessly.

"Thanks May," I say with real gratitude once she's settled on the couch beside me, slurping away at her food. "You didn't have to do any of this, I...thanks a lot. Really."

She glances at me and gives a small, tight smile.

"I don't like when you are hurt, Roger. You need to be careful."

There's something in her look I hadn't really noticed before -- a sincerity, a worry. Suddenly I'm struck by how pretty my pushy petite landlady is.

"Roger...Thai people, they learn fighting, they do kickboxing, Muay Thai...but for many people that's the only way to make money. To live. I know for you it's just a hobby, but...you need to be careful. So you don't get hurt anymore. Okay?"

She's watching me earnestly, her slender hands wrapped around her steaming bowl. She'd been married before, I know that much -- she moved to the States for a bit before getting divorced and coming back here, which is why her English is so good, her style more Western. Right now she's wearing a loose, sleeveless black shirt and tight-fitting jeans that show off her figure, her makeup subtle and refined. I gotta admit she looks damn good.

I'm not sure why her expressing concern gets me going and noticing things, but it definitely does.

"I...I will May. Really. You don't have to worry about me."

She rolls her eyes theatrically and grabs the remote, switching the channel to a singing show.

"Yes I do," she smiles. "But I can't take care of you every time. You still need a girlfriend, remember!"

I chuckle and we sit just like that, eating and watching together. She gets up from time to time to get us more beer, and each time I offer to help she swats my arm.

Even with the drinking I'm really starting to tighten up, though. I desperately need to ice; I don't really like asking for help, but it's better than getting snapped at again.

The next time she goes for a drink I say something.

"May could you...grab the ice pack please? It's in the freezer tray. I would go and get it, but..."

She gives me a level look as I start to explain myself, staring me down until I stop. Then she smirks and turns to grab it, bringing it back along with a fresh pair of Tigers.

"It hurts?" she asks as she sits, eyeing my reddened, bruising thighs as I hiss out an intake of breath at how cold the pack is.

"Uhh...yeah, a bit," I say through clenched teeth.

"Poor Roger," she pouts, saying it sweetly, placing her hand just above my knee.

That does something. It's not so much what she says but the way she says it, speaking to me in a soothing coo as if I were a child, or a small animal.

Suddenly my hair is up on end, my pulse pumping. What the hell?

"You're so strong," she continues, her voice sounding like silk. "But I try and tell you and you just don't listen. You still need someone to take care of you..."

Her delicate fingers pry mine off the ice pack as she adjusts it for me, moving it further up my leg.

"I...haha, yeah I, I am looking, I guess..."

It's an effort to swallow -- my mouth's gone suddenly dry, and I'm quickly realizing it might be an issue that I never got any boxers to wear beneath.

I set my bowl down in my lap before anything can get too out of the ordinary.

"Do you just ice it, or...do you massage, too?"

She asks it innocently enough, her thumb and forefinger subtly kneading the skin at my knee...but something's going on here and I'm not sure what, and even with the ice and the cold beer the room is getting way, way too warm.

"I...umm, I guess I massage it after I ice, but it's nothing too special...I don't really know what I'm doing, I just..."

I trail off. She's smiling at me and it's different. I can't really say how, but it's different.

"Maybe I can...help you," she says thoughtfully.

I open my mouth to respond but all that comes out is a surprised cough as she shifts, pulling her legs up underneath herself and leaning in closer, her scent of jasmine and citrus washing over me as she moves the pack again.

"Is this okay?"

I have no idea what to say so I just nod, not trusting my voice; her soothing touch has started to travel up my leg, squeezing at my sore muscles in the ice's wake. It hurts and feels so good at the same time, and I can't help but groan ever so slightly.

"Hmm...you like that?" she asks, giggling like a schoolgirl.

I still don't know how to respond, I'm so thrown off; her sweet demeanor is the exact opposite of everything she's ever shown. My mind reels at the dissonance, and all I can do is nod again.

"Good. You know, Roger...men always think they are so indestructible. That they can't be hurt...especially a young man, like you. But that's not true, is it? You still need help, just like anyone...don't you?"

There's a playful sparkle to her eye that I'm having trouble understanding, and suddenly I can't help but feel like I'm in way over my head.

What the hell is going on?

"Uhh, yeah I...guess you're right," I smile nervously, not sure where she's going with this. "Thanks...thanks again for helping me, May..."

"It's my pleasure," she says with a slow pretty smile, showing her perfect teeth. I tense as the ice pack travels further, pushing up my shorts, her massaging fingers following closely behind. She works my sore muscles well, and I'm slowly becoming more and more aware that that's not the only part of me that's aching.

I shift the soup bowl some more, suddenly noticing the delicate, feminine curve of her clavicle, the slenderness of her wrists, the way her wavy dark hair almost obscures one of her eyes, watching me so intently.

"May...I...uhh..."

"Hmm?" she hums, tilting her head curiously as she leans across me, moving the ice pack to my opposite leg, her expression still so unbelievably innocent.

"You what, Roger?"

She's so close, she's inches away as her black lacy bra shows beneath her loose top, her same-colored panties peeking over the tops of her jeans. I've got nothing to say; my mind's gone blank. I mean I've been with women before, more than a few -- but May is fourteen years older than me, and before tonight I'd just seen her as a helpful but bossy auntie. I can't even be sure what she intends, but for sure this is the first time I've ever felt so--

"Let's move this, huh? It's getting in the way."

Without realizing what I'm doing I release my grip on the bowl, and it's not until it's out of my hands and set aside that I realize my mistake. What's left in its place is more than obvious -- there's a fat fucking shape in my shorts, a huge lump pulsing to its own beat, a stain of wetness along one end where its leaked against the fabric.

Our eyes fall to it at the same time; she's so close I can hear her breath catch.

"Roger..."

I'm tingling all over; she says it so breathily, as if she's not in complete control either.

"I want to...take care of you tonight. Ok?"

I nod, dumbfounded.

"So I need you to tell me...where it hurts. So I can make it better. Can you do that?"

I nod again.

"Good."

She runs her fingers up my thigh and shows that pout again, her voice sweet as honey.

"Poor man...poor poor Roger. This is where it hurts, hmm?"

I swallow hard as she coos, shivering as her soft-peach nails tickle my leg through the fabric.

"Y...yes..."

"And how about...anywhere else?"

She pauses and gives me an expectant look, a certain simmering heat flickering in her eyes.

"I...umm..."

A single finger traces down the center of that outline in my shorts.

"How about...here?"

Her smile is warm and sly and full of hidden hunger, and my whole erection twitches at her slightest touch.

"It's...yeah. It...it is starting to hurt there, actually..."

"Mmm. I thought it might."

She leans in, her lips hovering so close to my neck, her soft voice speaking barely above a whisper.

"Relax, Roger..."

Then her hands are in my shorts, her petite fingers striving to encircle my base, squeezing and making me gasp.

"Oh shit...oh shit, May..."

Her grip pulses, as she places a line of kisses along my jaw.

"Relax..."

She pulls it out, thick and throbbing and veiny, looking absolutely enormous in her lithe little hand. I'm drooling from the head; I'm so damn worked up I'm bigger than I've ever been, bigger than I've any right to be.

On sight of it her eyes glaze over, a small sound escaping her throat as her gaze locks onto mine.

"Oh Roger...oh, Roger..."

She lays on her stomach, draped across me, squeezing and keeping that pressure around my hilt, making the rest of me so damn sensitive, making that fat tip turn purple. She looks up at me again and that's when she starts to drizzle saliva across it, spitting slowly, taking it in both hands and stroking.

"Oh shit...oh shit, May...what the hell..."

"Mmm...you're such a good boy," she purrs, drooling and dribbling down onto my head, making my cock shiny and wet as she passes it between her palms. "Such a strong man..."

It feels fucking incredible -- her slow languid care is the most erotic thing I've ever experienced, her sugary sweet words the sexiest thing I've ever heard.

"Even a strong man needs help to heal...and I'm gonna help you..."

I let out a shuddering breath as she tugs my shaftskin tight and starts to swirl her tongue around my head, licking it luxuriously, humming happily to herself.

My toes curl, every part of me flexed.

"Oh my god May, that feels..."

"Mmm? You like it...?"

"Yes I...god, that's so good."

She smirks and takes the tip in her mouth, sucking and slobbering freely as her soft hands twist and tug, all of me coated sloppy in her spit. She's a fucking expert, she's a goddamn pro and I've never felt anything like it, not even close.

Then she takes a deep breath and throats me as far as she can.

"Haaaa!" is the sound I make as air escapes my lungs, my reaction completely involuntary. I can't breathe at all until she comes up, spluttering, her eyes bloodshot, an eager grin grown wide across her face.

"Oh May what the fuck...holy hell, I--"

I'm cut off as she does it again, gagging herself on my fat shaft, punching it down her throat over and over, seemingly unsatisfied until I'm completely caked in her throatslime.

I can't even make a sound as it's happening -- my whole body's tingling, unresponsive. She's found my off switch, and all I can do is watch and listen as she impales her face with a soft gluck, gluck, gluck, wishing it would never end.

She gives it to me for a good little bit then gasps and sits back on her haunches, laughing as she starts to jerk me off some more. Her hands are so quick, my cock so slick and sloppy. She turns my whole world to pleasure -- space and time are gone, and I lose track of everything else but the beautiful older woman before me, that and the overwhelming urge to ejaculate.

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