Got a [handjob] from my mom’s friend [mF]

The plan was, I would go to my mom’s friend Cassandra Mills’ house Saturday morning. Just like every Saturday morning, her husband Tom would escort their three kids to all their usual meets and matches and sports leagues. While he was out, Mrs Mills and I would take advantage of her being home alone in order to prep their backyard for a surprise birthday party for Tom’s 40th.

Or at least, that had been the plan she’d told me about. I never expected it when she… but, well, I should start at the beginning.

A week back, I walked into my kitchen to grab a snack when I overheard a conversation.

My mom leaned against the kitchen island while her friend Cassandra Mills sat on a stool opposite. Mrs Mills was saying, “…how hard it is to find a good babysitter. You know how it is with young kids. Never a moment to yourself. That was Tom and my first quiet evening since… I don’t know how long.” She laughed.

My mother laughed along with her. “Well Belle’s always available if you need another night away.” Belle’s my sister, not that that matters. “She’s happy for the money, saving up for this summer camp she wants to do.”

I was eighteen and horny, so of course I was checking Mrs Mills out, the same way I checked out every single female, imagining what they’d look like naked, what they’d look like with a cock in their mouth. She was trim, but everything about her shouted ‘young mother.’ Her expression, cheerful but bland. Her brunette hair, short and practical, not even reaching her shoulders. Her outfit, a tame pastel workout jacket paired with functional yoga pants.

At that moment, nothing there caught my eye.

“That’s so responsible of her,” she was saying, “At her age I was just blowing all my babysitter’s cash on makeup and clothes.” Blowing all her babysitters, heh.

“These kids,” my mom said, “It’s a different generation. Even Ian there–” she nodded at me, “–He’s saving his cash too. Him and his girlfriend play the stock market, if you believe it.”

Mrs Mills looked over at me for the first time. Her gaze shone bright, innocent, betraying nothing. “Oh? And what work are you doing, Ian?”

My face was full of chips, so Mom answered for me. “Yard work, house work, whatever he can find, really.”

“Well, hey,” Mrs Mills said, “I’ve got an idea then…”

And that’s how I found myself in Cassandra Mills’ backyard, sweeping leaves, hosing off the patio, unfolding the canopies, setting out decorations and tablecloths, wheeling the drink coolers into position. It was nothing too strenuous, but there was a lot and I was laboring away in the morning heat. I’d pulled my shirt off, having soaked it through with sweat. So when I heard the sliding door crack open and saw Mrs Mills holding a tray with glasses and a pitcher of ice water, I felt nothing but grateful.

She approached, wearing the same cheerful, virtuous expression as always. Her hair hidden, tucked into one of those workout hats, with simple makeup. She glanced at my tan chest, but then away. She was just a young mother thanking her friend’s son for helping out around the house.

“Sit, sit,” she said, waving towards the wicker furniture I’d just set out, “You deserve a treat after working so hard!”

“Nice, thanks,” I said, reclining into the settee. She put the tray down on the glass-top coffee table in front of me, bending over to pour water into a cup. I got a face full of her yoga-pants clad ass. “I’m sure thirsty, Mrs Mills. A cold drink will hit the spot.”

I felt a touch bad about checking out her butt — her maneuver was chaste, I was taking advantage, turning everything into something sexual — but it was a nice, round ass, the woven texture in the fabric emphasizing the curves of her muscles.

“Oh gosh, Ian. No no no!” she said, sliding into the spot next to me. She pressed the cup into my hand, “You have to call me ‘Cassie,’ saying ‘Mrs Mills’ makes me sound so old.”

She had golden brown eyes, crinkled in the corners as she smiled at me, her tan features upbeat and peppy. I could see a touch of cleavage with her gym sweater unzipped a few inches, but I pretended to ignore that.

I returned her smile. “Sure thing, ‘Cassie.’” I took a sip. “Anything else left on the list? I’ve got nowhere else I need to be.”

Her grin widened and she rubbed my knee. It was a lighthearted gesture, the touch meant nothing. “Nope,” she said, “You did good work here, thank you! But what do you mean, nowhere to be? Shouldn’t you be with that girlfriend your mom mentioned?”

“Oh, Daphne?” I said, “Yeah, I guess. We just hang out whenever, though. We don’t really make plans or anything.”

“What? No!” Cassie pantomimed horror, “Letting a relationship grow complacent is the worst thing. You’ve got to keep things romantic, especially if you want the bedroom to stay, uh, interesting.”

I chuckled awkwardly and took a deep gulp from my cup. “Heh, yeah.”

She blushed. “Oh, I’m sorry! I just assumed you guys were… My apologies. I’m always so presumptuous. Are you waiting until marriage? ‘Saving yourself,’ something like that?”

I looked down, unable to meet her gaze. “Err, no, it’s…” I hesitated, “It’s not like that. We just, uh, haven’t gotten there, I guess.”

“Oh, I see,” Cassie said, leaning across me to refill my glass, her tits in my face. “It’s a newer relationship, then?”

“Well, no. We’re almost a year. We’re pretty serious, I think.”

“You ‘think’?”

“I mean, it’s our first, really. For both of us. So I think we’re serious, but… yeah. I guess I don’t know.”

“Well…” Cassie tilted her head, “Sex is a healthy part of a serious relationship. Maybe I can help. You do want sex, right?”

I thought I’d be more nervous, but it was oddly refreshing speaking openly about this, and I was able to hold eye contact as I said, “Right.”

“Wanting sex is good,” Cassie nodded, a thoughtful look on her face, “But the word ‘sex’ means a lot of things. So, when you say no sex yet, I’m guessing you’re including anal?”

“Err, yeah.”

“Oral?”

“Yea–yes.”

“’Yes,’ she’s blown you? Or ‘yes’ she hasn’t?”

“No, she hasn’t, um… nothing oral.”

“I see. What about with hands? Groping, fondling? Do you and Daphne do a little mutual masturbation?”

I felt the warmth returning to my cheeks. “Um, no. Haven’t, uh… like that.”

“But you masturbate yourself, right?”

I froze, eyes wide. But Cassie’s expression was wholesome, honest, helpful. She just wanted to know if something was wrong. “Um, yeah, sometimes.”

“And are you thinking about, oh, what’s her name?”

“Daphne.”

“Are you thinking about Daphne while you masturbate?”

“I… uh… I dunno…”

“You don’t know? Daphne doesn’t make your cock stiff? Or… do you watch pornography?”

My blush dominated me. I sipped from my glass, my gaze darting around nervously, anywhere but meeting Cassie’s eyes. A bead of condensation dripped down the side of the pitcher, pooling on the tray beneath it.

Cassie continued, “Cuz if pornography’s making you cum but your girlfriend isn’t, Ian, well… maybe you two just need a helping hand.”

My breath caught. Cassie’s fingertips slid under my shorts and traced the contours of my thigh muscles.

“Umm…” I said dumbly. I knew what she meant, I wasn’t a complete idiot, but I didn’t know what to say.

“I’ve put you to work all morning,” Cassie purred, “The least I can do is help you out in return.” Her hand slid up over my crotch, rubbing me on the way. Suddenly aware of how little clothing I was wearing, I pulled my arm across my belly, holding the cup of water firmly.

She took it from me, pouring its contents out on my chest. I gasped as the cold water dripped down. Cassie’s eyes followed the rivulets, her gaze admiring, applauding my brawn.

She unzipped her lycra jacket slowly, one notch at a time, showing bare skin beneath. It was my turn to stare. Her cleavage deepened, rounder and more full than her concealing clothes had ever let on. I sucked in a breath through clenched teeth.

She dropped the zipper lower and lower, my eyes glued to its every movement. But she stopped just short of revealing her nipples. I looked up, shooting her a desperate look.

She flashed me back an impish grin. “Take off your shorts, Ian.”

What was happening? The world spun. I watched myself through a haze, my body standing, my arms pushing shorts and briefs off, my leg kicking them away as my body sat back down. I wasn’t in charge of any of this, something else controlled my actions.

So I found myself sitting there, buck naked knees spread, this MILF against my side, one of her hands running fingertips up and down my sensitive inner thigh, the other gripping my penis.

“Is this how you masturbate?” Cassie said, “Slow and steady?”

I whimpered my answer, my dick growing stiff.

She spit into her palm, massaging it into my shaft, mixing it into the precum dribbling from its tip.

“This is one seriously thick cock you’ve got, Ian,” she said, cupping my balls in her other hand. “How does this feel?”

She slid her hand up, her tight grip squeezing the head.

“Good,” I said.

She brought her fist down until it was against my hips. “Just, ‘good’?”

I was panting, breathing hard. “Feels amazing,” I muttered. Her hand had slid back to the tip.

“That’s more like it.” Her grin grew pitiless, her hands retreating to her sides. “Now, I want you to practice.”

“Practice what?”

She slapped my cock. It bounced against my thigh before springing back up. “Tell me what you want!” she barked.

“What?”

She batted at my cock again. “Do you want me to make you cum?”

“Y-yes!”

“Then tell me what you want!”

“Fuck me,” I whimpered, “Get me off.”

“That’s better,” she grinned. She slapped my cock again. “You’re a bad boy, Ian, shoving your hard dick in my face.” She slapped again, and I groaned. “But I’m not going to fuck you.”

She grabbed my balls. “I’ll milk you dry,” she said, “But it takes more than yard work to get my pussy.” Her fingers made a ring around the base of my balls, tugging on them, pulling the skin taut.

She grinned, cinching harder and harder, until I groaned, “Fuck…” She gripped my balls like they were a treat, running a single fingertip lightly across my sensitive skin. My breaths came fast and shallow, and she delighted in the control she had.

“When’s the last time you came, Ian?” she said, “When’s the last time you sat there, all alone, jerking your sad little boy prick?”

“I dunno, a week.”

“Bullshit!” she said, squeezing my balls harder. “Tell me the truth!” My cock, neglected but stiff, sprung up lamely. It was eager, but she scowled at it, as if the idea of touching it disgusted her.

“Last night…” I whined, “It was last night.”

Cassie grinned. “And what makes you drain your balls, Ian?” The pressure on my sac made me whimper. “What makes your teenage sperm flow?”

She flicked her fingernails over the skin of my balls, and I shuddered. “What?”

“What were you thinking about when you came, Ian?”

“A– uh…” I said, panting, “A blowjob.”

Her grin widened. “A blowjob,” she repeated, “Your fantasy is to feel a girl drinking your cum?”

I whimpered. Fluid dripped down my shaft.

“How do you think it feels, Ian?” she said, “With cute little Daphne, her lips wrapped around your thick cock, slobbering and sucking?”

“I want it…”

“In you fantasy, does she spit your cum out?” Cassie’s hands gripped the base of my cock, wiggling my shaft side to side. “Or does she swallow your fat ropes like a desperate whore?”

I moaned, my spurned cock twitching.

“Do you defile her with your dick?” She ran a thumb up the vein bulging from the underside of my shaft, making my body convulse. “Do you shove her head down until your dick’s in her throat, pinch her nose to make her choke? Does she gag and sputter as you fuck her mouth?”

My eyes went wide as she pinched the head of my swollen cock between her thumb and index finger, massaging my glans with the tiniest motions.

“Do her eyes roll back in her head as you pump your sperm into her? Does she choke, cum dripping from her nose?” She teased my shaft, fingertips running up and down its glistening length. “When you degrade her with your seed, does she make you feel like a man?”

She pulled back and slapped my cock again. “Or are you just a little boy, too chickenshit to take what you want?”

“Please…” I said, “I need it.”

She batted at my dick, knocking it side to side. “Need what?”

“I need to cum,” I said.

“So then jerk yourself off,” she scoffed, “Masturbate your little boy cock. If that’s all you’re good for.”

“I need you…”

“Need my what?”

I gulped. “Show me your tits.”

She grinned. Her fingers slid up and over her chest, meeting in the middle. Slowly, deliberately, she unzipped her jacket down to her navel, two large, round breasts rolling out. She looked down, cupping them in her palms, fingers pinching her pert nipples. “I thought you’d never ask.”

My cock twitched.

She smiled, grabbing my shaft, rubbing it against her nipples. I grunted, “Oh fuck…”

“Mamma’s milk jugs are here for you,” she said, leaning forward, sliding my shaft between her tits, bright red against her smooth, tan skin. My dick stiffened the hardest its ever been, every vein sprung tense, pumping blood.

“Stroke me,” I said, half begging, half commanding, “Make me cum.”

Cassie grabbed my cock with two powerful fists, one above the other, and pumped with vigor. My dick pointed straight up, its head bouncing against the valley of her breasts. She rubbed and rubbed, rhythmically, methodically, forcefully. My dick swelled and swelled, at last getting the attention it craved.

My jaw slackened, eyes widened, swollen balls slapping against my thighs with each powerful tug.

Cassie’s grin spread ear to ear, mischievous, devilish. It echoed her earlier smile, the innocent, young mom one, but twisted into something wicked. I felt soft, like clay, like something molded, taken advantage of, used for her sick pleasure.

And I fucking loved it. “Yes, yes, yes…” I wailed.

With the unflinching rhythm of a steam engine, she pumped and pulled on my cock. Her arm muscles tensed, the action practiced, expert.

She tucked her chin and winked. “Cum for me, little boy.”

I groaned loudly, my cock twitching, my body bucking. I could feel it, coursing its way through my body before erupting, a fountain of cum blasting from my dick. Cassie looked pleased with herself as spurt after spurt launched onto her tits, dripping down into her cleavage, from her nipples. Cum sprayed on my belly, on the settee, on the ground.

She released me, my shaft dropping to my stomach, still hard, still oozing cum. I sat in a daze, sagging back into the seat. She smiled, squeezing my balls. “Anything left?”

Another spurt shot onto my belly. Cassie’s eyebrows shot up. “Oooh, I love these young cocks. So healthy and full.” She licked her fingers. “And so fucking tasty, too.”

## ## ##

That night, I was at Daphne’s house, in her bedroom, naked on her bed. I had her clothes off, her pony tail in my fist, driving her face onto my cock. She was a cute girl, but she was hesitant and mechanical as she sucked. She was eager, but she just didn’t know what she was doing. So I helped, guiding her lips up and down my shaft.

Even still, it wasn’t working, I was going to go limp if it kept up this way. I knew Cassie wouldn’t be so inept, wouldn’t be fumbling and unsure. I closed my eyes and dreamt it was Cassie’s experienced mouth sucking me off, her awesome udders swinging beneath her as she grinned, her golden eyes winking at me.

That thought did it. I was cumming, squirting into Cassie’s… I mean Daphne’s mouth. Daphne squirmed, pulling off before I was done, making a face. “Ugh, you’re supposed to warn me.”

I sighed. This was a problem.

I tapped open my phone, finding Cassie’s name.

Daphne pulled on her pajamas. “Who’re you texting? You bragging to your friends?”

“Nah,” I said, “Nothing like that. Just scheduling some work.”

I smiled as the phone glowed in my face. “I could use another job. Free again next Saturday?” my sent message said. Cassie’s response read, “Sure! Don’t forget to bring your tool. And by tool I mean dick.”

Source: reddit.com/r/sexystories/comments/pfem2k/got_a_handjob_from_my_moms_friend_mf