Side Hustle

When I turned onto my street on the way home from work, I saw a familiar car parked in front of the house. My cheeks started burning, and I turned before reaching the house.

I had always been nervous and embarrassed around my mom's friend Marissa, because she was hot as hell, with huge tits. I wasn't exactly drowning in pussy, so having her around all the time was pure torture. That was bad enough, but two weeks earlier I had stumbled across naked pictures of her while scrolling through some porn. Those tits were everything I'd ever fantasized about, and despite what I thought my preferences were, her trimmed pussy got me throbbing.

A search of the name Marcy May led me to a website with more of her pictures — though none of them showed her face. It was basically a big tease for her Only Fans page, and all the images were censored. So I headed back to the porn site where she was naked and playing with herself.

I went off like a rocket jerking it to those pictures.

The next time she was at the house when I was home, my face got so red and hot that I'm surprised I didn't burst into flames. I knew right then and there that I had to avoid her at all costs.

I headed back uptown, grabbed some tacos, and then carefully made another approach to the house a street down. When I didn't see her car, I breathed a sigh of relief and circled around so I would be coming in from the normal direction.

"There you are," Mom said as soon as I walked in the door. "You're a half an hour late."

"I stopped to get some tacos. Don't worry so much, Mom," I said as I headed toward my room.

"Now, hold on. I'm your mother, and I don't care if you're over eighteen. I'm allowed to worry as much as I want, no matter how old you get. That's not it, though. I need you to do me a favor."

"Oh, Okay."

"Marissa is having a problem with her computer, so I need you to help her get it sorted out."

That immediately piqued my interest and stopped me in my tracks. If she was taking naked pictures, there might be more on her computer that I could copy. "Did she bring it over?"

Mom shook her head. "It's a desktop, so I need you to go over there."

Shit. Not good, I thought in a panic. "I was going—"

Mom cut me off. "Going to head over there right now because my mother asked me to, and it's the nice thing to do?"

My brain locked up, and I couldn't think of a single excuse to get me out of it.

Mom smiled and said, "Thank you. I'll call her and let her know you're on your way." The words had barely left Mom's lips before she started dialing. She impatiently waved me toward the door while telling Marissa, "He'll be right over."

I was trapped. I turned and walked toward the door — thoroughly convinced that I'd never walk back through it because I was about to die of embarrassment. In my mind's eye, my car transformed into a hearse, and I thought I should be climbing in the back instead of the driver's seat.

It was only a few blocks to Marissa's place, but I was sweating and my heart was thundering in my chest by the time I got there. At the entrance to the gated community where she lived, I punched in the code she'd given my mom — knowing full well that it would announce I was there. Sure enough, the door to her apartment opened before I had time to shut the car off.

My mom's brunette friend was wearing a tight black dress with a plunging neckline — and a smile. I swallowed, took a deep breath, and climbed out of the car.

"Come on in," she said as I approached.

"Mom said you had a computer problem?" To my relief, my voice didn't crack.

"Mmm hmm," she responded as she closed the door. She then walked over to the couch — her heels clicking — and gestured. "Won't you sit down?"

That confused me enough to overcome my nerves momentarily. I walked over to the couch with a furrowed brow and sat down. The brief reprieve was over when she sat down right next to me. The smell of her perfume and all the cleavage on display mere inches away had me fighting an erection and my eyes trying to home in on her tits.

"So, where did you find my pictures?" she asked.

I didn't drop dead on the spot, which was an unwelcome surprise at the time. Instead, my eyes went wide and I sucked in a gasp as my face started burning.

Marissa reached out, cupped my cheek, and said. "It's okay. You're not in trouble. I'm not going to say anything to your Mom. Breathe."

The moment her hand touched me, the world seemed to vanish around me. All I could see was her smiling and looking at me. All I could hear was her deep, sultry voice. Her eyes had me in a trap.

"In and out. There you go." She chuckled. "I knew something had happened the other day when I was over. You were always shy around me, but you looked like you were about to come out of your skin the last time I saw you."

I still couldn't think. The feeling of her caressing my cheek was sending chills up and down my spine.

She said, "I suspected, but when I searched the logs on my website, there wasn't much doubt left. One hit from an IP in town, on a Samsung phone, at the right time of night..."

She twitched her eyebrows as her hand slid down from my cheek and she sat back. "It's my side hustle. I only make a little over three hundred a month, but it's fun. I've always liked showing off."

I couldn't believe my eyes when she pulled down on the front of her dress and lifted those big, gorgeous tits out one after the other. She squeezed them together, and jiggled them.

"See? I don't mind that you've seen them. Get a good look."

As if I needed that instruction. I couldn't take my eyes off them. She was right that I'd seen them before, but an image on a screen and real, live tits close enough to touch were two different things.

I didn't even notice her moving because I was drinking in every inch of those tits, committing them to memory like they were the last thing I would ever see. I snapped out of that real quick when she curled her fingers around my wrists and lifted my hands.

There was no holding back the groan when she put my hands on those soft, warm tits.

"Mmm... There you go," Marissa moaned. "A little more relaxed now?"

I nodded as I squeezed and ran my fingers over her breasts. I couldn't believe it was happening.

"Did you tell anyone else about my pictures?"

"No," I answered while shaking my head. My thumbs slid over her big nipples, and they felt hard.

"I'd like to keep it that way. Especially from your mother. Can you do that for me?"

"Sure." There was no way in hell I was going to tell my mom that I'd seen her friend naked.

"Can you show me where you found my pictures?"

"Okay," I answered while continuing to worship her breasts.

She let out a laugh. "They're not going anywhere. Show me."

With the greatest of reluctance, I let go of those incredible tits and reached into my back pocket for my phone. It only took a few seconds to bring up the browser and click the bookmark to her pictures.

"Make sure your phone locks every time you leave it unattended," she warned. "All it would take is for you to leave your phone unlocked where your mom could see it... It would be better if you didn't save the links." She then read the header on the page, "Perfect big boob Milf Marcy May fingers her hairy pussy. I like that, even if it is copyright infringement."

Marissa then turned and picked up her phone from an end table. "Read that address out for me?"

I rattled off the address while she typed it into her own phone. As soon as I'd said the last little bit, I locked my eyes back on her tits. It felt strange — and hot — to watch her doing something so mundane as typing on her phone with her boobs out.

She continued to tap away and explained, "One of my fans is a lawyer, and he sends out cease and desist mails for me whenever I find my pictures on some site. It doesn't always work, because a lot of them are in other countries, but..."

Her shrug caused her breasts to lift in the most fascinating way.

"There. One more down. Most of my fans are good about it, but one must have leaked some of the pictures behind the paywall. It was inevitable I guess. I never see anything new, so they must have signed up, downloaded everything, and then cancelled. I spend so much time trying to track them down."

"Have you ever done a reverse image search?" I asked.

"Hmm?" she asked.

"Like this," I said, and then tapped on one of her pictures on my phone. A few seconds later, I brought up search results with a list of about twenty other Milf sites where her pictures were.

She gasped. "Oh my god. I spend ages scrolling through those sites, and you found them all in a couple of seconds. Can you do that with any picture? Can you show me how?"

"Yeah. All you have to do is..." I trailed off when she stood up and offered a hand.

"Come show me on my computer."

I took her hand and stood. She kept hold of it as she led me into the apartment. Even though her tits were still out, my eyes were drawn to her ass swaying back and forth. She smiled when she caught me looking.

The room she led me to was a bedroom, but it wasn't. The computer was over in one corner, and the rest of the room was filled with cords, ring lights, cameras on chargers, and tripods — all surrounding the bed.

Marissa finally let go of my hand when she sat down at the computer. She looked over her shoulder, grabbed my wrist, and settled my hand on her left breast. My eyes lit up when she logged into her Only Fans, revealing more naked pictures that I'd never seen before. My eyes darted back and forth, taking it all in while I squeezed and fondled the real thing in my hand.

She navigated to a picture set and said, "Walk me through it."

"Right click on a picture," I said.

"It's this one, isn't it?" she asked while hovering the cursor over the menu selection.

"Yes, that's right."

"So I click, wait for it to load, and then click here and..."

The picture showed a list of around twenty Milf sites — most of which I recognized, and were repeats from the earlier search on my phone.

Marissa opened her email, and started copying the links. "I give my lawyer fan a custom picture whenever he sends out a C&D for me. I'm probably going to owe him a few after this. You're making the other one jealous, you know?" She glanced down at her tits.

I got the hint. I gave my uncomfortably hard dick a squeeze, and then filled my other hand with her right boob.

She finished copying the links, and then typed a message saying there would probably be a bunch more.

"You'll probably find a bunch of different sets on the same site. Maybe he should wait so he can send all of them at once."

"Good idea," she said, and amended her email. Once she hit send, she said, "I want to try something, and see if I have it right."

I bit my bottom lip as I considered something, and then decided to go for broke. I pinched her nipples, and she rewarded me with a moan.

"That's what I thought," she said after the search finished. "These are about two months old and it doesn't find them anywhere. I guess I need to watch out any time someone signs up and then unsubscribes really quickly."

"Uh huh," I muttered. I was only half listening because I was enjoying her tits in my hands and the picture of her with a butt plug in and a vibrator buried in her pussy.

An alert popped up on her computer, and her phone sounded off as well. Marissa ignored them at first, navigating to a different picture set of her outdoors somewhere. Once she started the search, she checked her phone.

"Hmmm..." she hummed as she put her phone down. "You really like my tits, don't you?"

"Love them."

"Let's see how much."

I reluctantly let go of her tits when she turned in the chair. It was well worth it when she reached between my legs and squeezed, though. Her eyebrows shot up and she gasped.

I could hardly believe my ears when she looked up at me and said, "My lawyer fan wants some pictures of me with cum on my face and tits. Care to help me with that?"

I stood over her with my mouth agape for what felt like an eternity. She waited with her eyebrows raised, and eventually I got over the shock enough to nod.

"Go sit down on the bed," she prompted while giving my prick another squeeze.

She stood with her hand still between my legs and gave me a nudge in the proper direction. I backed up toward the bed, navigated around the footboard, and sat down on the corner at her urging. Marissa turned around, plucked the charging cord out of a camera, and then placed it up by the pillows.

My mom's friend stepped in front of me wearing a sultry, crooked smile. Then she bent over — her big tits hanging — and tugged at the end of my belt.

"That's the first time you've touched real tits, isn't it?"

I nodded.

Marissa shuddered as she unhooked my belt. "God, this is so wrong, but that's what makes it so fucking delicious. I know my panties are soaked right now."

She made quick work of the button, yanked down my zipper, and then wrestled my jeans down. She let out an incredibly sexy growl when my hard-on popped free. I gasped and fell back on the bed when she wrapped a hand around it.

"God, that is a gorgeous cock," she said with a level of excitement that I thought had to be for my benefit.

The thought lasted about a nanosecond against the incredible sensation of her soft hand sliding up and down my dick.

It must have registered on my face, though. She said, "Don't believe me? You're only about average length, but that's not what matters. This is one thick dick. It's just made to stretch a girl's pussy out and make her scream. And this big head..." She rubbed a fingertip over it, making me throb. "Like I said. Gorgeous."

I found the strength to lift up on my elbows and watch her slowly jerking me with one hand while she tugged at my jeans with the other. She managed to free my balls, but then let go of my dick and stood up straight.

"You know what, we're going to take these all the way off," she said, and then knelt down next to the bed.

Marissa yanked at my shoelaces to untie them, and immediately pulled off my shoes. My socks followed, and then she stood back up.

"Scoot back and lift your butt."

I did, and she quickly dispensed with my jeans, which fell in a forgotten heap on the floor next to the bed.

"Take your shirt off," she said while kicking off her heels. She then reached behind her back.

I sat up and quickly yanked my shirt as I watched her unzip her dress. I didn't want to miss anything, so I pulled it over my head — just in time. My mom's friend started wriggling out of that little black dress. Once it passed her hips, I saw her panties, which were a lacy white. I could see a dark shadow behind the crotch, which was the first hint of her hairy pussy.

Her dress slithered down her legs and she stepped out of it. My heart started racing when she pushed down on her panties. They had slipped low enough to reveal the trimmed triangle of dark hair between her legs when she let out a chuckle.

Marissa stepped up right next to the bed while holding the front of her panties stretched away from her. She beckoned me with a wave and said, "See, I told you."

I looked and could see the darker spot in her panties as well as a strand of clear pussy juice stretching from the wet spot to her pussy lips. The tips of the hair around her pussy glistened as well.

She pushed her panties the rest of the way down, stepped out of them, and then leaned toward the head of the bed. She grabbed a pillow, dropped it on the floor, and then said, "Stand up."

My mom's friend laughed when I scrambled to stand in front of her as she knelt onto the pillow. She reached up, cupped my balls, and circled a finger around the head of my dick.

"It's your first time, so don't be embarrassed if you need to come. It's as good a time as any to practice holding your cum, but don't hurt yourself. When you can't hold back any more, let me know. You should always let a girl know before you explode in her mouth."

I nodded and muttered, "Okay."

"Ready for Mommy's friend to suck that hard young cock?"

"Yeah."

She moaned when I throbbed and leaked pre-cum. She smoothed it into the head of my dick, and then brought her fingers to her lips. I shuddered when she tasted me and let out an even louder moan.

Marissa smiled, locked eyes with me, and leaned in. I groaned loud and long from the touch of her tongue. She slid it slowly up my length, looking into my eyes the whole time, and then kissed the tip.

"Feel good?" she asked before nuzzling my dick with her lips.

"So good."

She curled her fingers around me and said, "God. You are as hard as a fucking rock. You like me naked and on my knees?"

"Yeah. It's hot."

"Fuck, I love the thought of being the first one to suck your cock. Put your hand on the back of my head."

I did, and my fingers fisted into her brown locks when she started slathering her tongue all over me. She was moaning as she licked me, and the hungry, excited sound only added to the experience. I grunted, gasped, and trembled with zero control. The feeling of her slippery tongue gliding over me was so far beyond my jerk-off fantasies that I felt light-headed.

Marissa dipped down and tongued my balls next. She rolled them around with her tongue and gave one a suck. I stiffened because it didn't really feel all that good with her sucking it, and I guess she picked up on that, because she went back to licking. Finally, she licked me from root to tip, caught my eye, and teased me with just the tip of her tongue for a second.

Her lips parted and my other hand slapped to the back of her head when she took me in. Her mouth was so fucking hot. I could feel her tongue wiggling against me too. I watched in amazed fascination as my dick slowly vanished between her lips, and then reappeared covered in saliva, only to vanish again.

The first few sucks were slow, and she looked up into my eyes at the top of each one. I had a fraction of a second's warning when her fingers wrapped around the root of my dick tightened.

A loud inarticulate sound burst from my lips when she started bobbing her head. Her hair bounced and I finally heard the glock glock sound that was such a meme for real. My fingers tightened into her hair, and it only seemed to spur her on. She squealed around my prick and kept sucking.

It didn't take much of that to push me toward the edge. I tried to hold it back like she asked me to, but it was a losing battle. Just as I was about to warn her I was going to come, she pulled back and gasped.

I was panting for breath and my dick was jumping rapidly. Marissa wiped her chin, and then licked her lips. "You were getting close, weren't you? I could feel that cock throbbing."

"Uh huh," I grunted through clenched teeth. The feeling had barely waned.

"Relax. Hold it," she said.

My head bobbed in a nod, but it was easier said than done.

Marissa let go of my dick and looked up at me. She hefted those big tits and started playing with them. I leaned back against the bed and thankfully felt the urge to come start to subside. My mom's friend squeezed her tits, pushed them together, and pinched the nipples.

"Don't worry. I'm not going to tease you much longer. The next time I suck that cock, I'm going to make it explode in my mouth, and then jerk it off all over me," she said, and then leaned in.

Marissa rubbed her tits against my dick and asked, "Too soon?"

"No, it's calmed down," I answered.

"Good," she said, and then proceeded to sandwich my dick between her boobs. She squeezed them together and rocked, holding me in the warm, soft nest between her tits. "I still can't get over how hard you are. I'm surprised you didn't bust your zipper."