Crushing on Cassy

I woke up on Cassy’s couch again. It’s been happening all too often since my mom started dating her new boyfriend. Not that I minded too much. She was the one constant in my life. That, and the fact that I’ve had a crush on Cassy for as long as I can remember. They’ve been friends since Mom moved to California to be a star. She ended up a waitress like all the other aspiring actresses. Cassandra did make it, though, sort of. She does voice-over work and stand-up on the side.

Her impressions are hilarious. Whenever we knock, she does her Mrs. Wolowitz. “Who’s there? Are you a sex criminal?” She has a whole repertoire. Holly Hunter as Mrs. Incredible, Mya Rudolph as Aunt Cass. Her Jennifer Coolidge is spot on, which is why my mom calls her Aunt Fanny. I call her Aunt Cass because she looks kind of like the character from the cartoon. She has a nice figure, with a big rack and a nice jiggly ass.

Cass would stay up every night in a loose-fitting sleep shirt and watch the late-night shows with me, and every morning I’d wake up with the typical teenage morning wood. I quietly stroked my seventeen-year-old cock on the couch until she woke up and I could go finish jacking off in her bathroom.

This morning I was stroking my meat when I noticed her reflection in one of her awards. It was a mirrored plaque on the coffee table, positioned so I could see it from the kitchen. I realized that Cass had been watching me beat my meat. I tucked my cock into my grey sweatpants and went into the kitchen to say good morning.

Cass sat up straight and knocked a spoon onto the floor. It had fallen under the table. Her nightshirt hiked up when she went to retrieve it, exposing her luscious backside. I saw everything. I mean, I saw from her starfish all the way down to her glistening, pink pussy lips. It was apparent that she’d been diddling herself while she watched me. The thought of it sent shockwaves through my johnson.

“I’m, uh. I’m gonna take a shower,” I stammered, trying to hide my growing erection.

“Don’t be jacking it in there, either. I know what you’ve been doing.”

Cass had a bath mitt that felt heavenly when I lathered up to stroke my cock. Today didn’t take me long to blow my wad, but fueled by the image of her wet pussy, I was hard again by the time I dried off. I started to open the door so Cass could shower but decided to rub another one out into the toilet before I left the bathroom.

I was really going after it when Cass walked in. She was so startled that she dropped the towel that she had wrapped around her, revealing her naked body.

“That makes me want a hot dog real bad.”

That was all I needed to push me over the edge.

“Don’t waste it, Tommy!” Cass barked when I groaned. She pulled her hair back and dropped to her knees, mouth agape. “Cum in my mouth. Come on. You know you want to. I know you do.”

I shoved my cock in her mouth. “Oh, God, Aunt Cass,” I moaned as I held her head and started to fuck her mouth.

Cass pushed my hands away so she could catch her breath. Her hand kept pumping on my shaft until she was ready to take me back into her mouth. When she did, she took my cock all the way up to my balls. I don’t know how she did it, but she took all seven inches right down her throat. I only lasted another dozen strokes before pumping my load into her kisser.

“Uh, um. I should go,” I stuttered as I walked out of the room without my clothes. Uncertain what to do, I sat stunned on the couch naked while Cass showered.

Cass appeared a few minutes later, wrapped in a bath towel. “Can we talk about what just happened? It’s normal for boys... men your age to mast… It’s normal. Can I ask? Are you thinking about me when you... you know?” Her words were gentle.

“Yes. But today was differ… Today I saw your ass and your wet pussy, and I couldn’t get the picture out of my head. I was going to whack off a second time when you walked in.”

“Seeing my fat ass caused all that?” she asked sweetly.

“You’re not fat. You’re perfect. I’d eat your pussy all day, including your ass. Kneel on the couch, and I’ll show you.”

I got on the floor, licking her pussy from behind. I slid my tongue through her puffy pussy lips before sticking it in her sphincter and back to her pussy. “Oh, Tommy. You naughty boy,” she purred. “Lick it, Tommy. Eat my cunt.”

I turned and sat in front of the couch, head back so she could sit on my face. Cass ground her cunt into my mouth while I thrust my tongue into her hole. Every now and again, she’d arch her back so I could run my tongue across her butt pucker, sending shivers down her spine.

I shoved my thumb into her pussy, coating it in her juices so I could slip it into her bum. “Oh, fuck, Tommy. You’re gonna make me cum. Oh, God, Tommy. Oh, God.”

Cass bucked her hips, driving her cunt forward, grinding it into my mouth. “I’m cumming, Tommy. You naughty boy. You’re making your Aunty Cass cum,” she moaned into the back cushion.

She noticed that I was stroking my cock the whole while she rode my face. “Don’t waste it, Tommy. Don’t waste it.”

I half expected her to climb down and suck me off again, but she straddled my lap instead. Cass reached between us and inserted the tip of my cock into her dripping pussy. She held her ample titties in my face as she impaled herself on my shaft. I sucked back and forth between her nipples as she rode my cock.

I’d had sex before, but nothing compared to this. I don’t know if it was the things she was doing with her snatch or the fact that I was bareback, but her pussy felt exquisite. And from the sounds of it, she liked riding my cock too. She lifted my chin and kissed me full on the lips. Her tongue darted into my mouth, twisting with mine. “I’ve dreamt of this, Tommy. I dreamt that we’d end up in each other’s arms, fucking our brains out.”

“Me too, Cass. I sneak peeks at you all night long, just waiting for you to go to bed so that I can jack off. I dream about doing it with you every night. I’m so hard every morning that I have to do it all over again, and now we’re fucking for real.”

Cass rode me so hard that she started to get rug burns. “We’re going to have to change positions before I wear holes in my knees,” she said as she shifted back to the couch, kneeling backward on the sofa. “You can do me doggy?” she asked, pointing to her rear with her thumb.

“No, but I’m eager to try.” I grabbed her by the hips and slid my cock back into her pussy, fucking her from behind.

I could feel Cassy rubbing her clit as I fucked her. I grabbed her by the hips and hammered my cock into her so hard that my testicles slapped off of her pussy like a speedbag. The tip of my cock slammed against her cervix with each stroke. Her ass pucker winked at me as I stared down to watch my cock piston in and out of her vagina.

I rubbed my thumb in circles around her sphincter. “Put it in, naughty boy,” she moaned. She bucked like a bronco when I began to move my thumb in and out, and I felt a flush of warmth as she came on my cock. “You’re making me cum, Tommy!” Her pussy bathed my cock with its juices.

I pulled out my dick and pinched it off at the base, trying to prolong my orgasm as much as possible. In my young, lust-filled mind, I thought if I did her good enough, she’d let us do it again the next time I stayed over. I kept my thumb inside her butt while I buried my face in her backside, licking her pussy until my urge to cum subsided.

“Have you ever done anal, Tommy?” she asked, looking back at me.

“Can I?” I asked, thrusting my thumb up her bum.

“God, yes,” she groaned as another wave of ecstasy washed over her.

I placed the tip of my cock against her anus and pressed with steady pressure as she backed against it until the head slipped in. Once it did, she pushed back until her ass cheeks rested against my pelvis, burying my cock deep inside her ass. Cassy’s pucker gripped my cock so tightly that I almost came as it slipped in.

I grabbed her hips again and started to long, deep strokes as she dug her fingers into her pussy. She screamed into the back cushion of the couch as she came again and again. Her head flung back as she groaned. “I’m cumming, Tommy. I’m cumming.” Her sphincter clenched around my cock, spasming while she came, sending jolts of exquisite sensations through my cock and balls. “Please put it back in my cunt, Tommy.”

“I’ll cum if I do that.”

“Then go ahead and cum.”

“I don’t know if you’ll ever let me do this again, so I don’t want this to be over too quickly.”

‘You promise to keep your mouth shut about this, and I’ll let you fuck me every time you spend the night.”

I gave her anus a few parting strokes before slamming my cock back into her pussy. I pounded her pussy with all my might. Cassy bit the sofa cushion as she screamed at the top of her lungs. “Fuck me, Tommy. Fuck your Aunty, Cass.”

“I’m gonna cum, Cassy.”

“Do it! Cum for me. Fill my pussy, Tommy.”

I buried my cock balls deep, pumping a big load of cum into her cunt. “Oh, fuck, yes, Tommy. Fuck it.” I continued to slam my cock up her until my erection withered away.

“I wish we could do this every night,” I said right when her phone buzzed.

“Looks like you’re gonna get your wish. That was your mother. They’re on their way to Vegas. Looks like we get to fuck all weekend.”