Skip to content My house was being renovated, so I had to stay at my aunt’s place for a while. My mom was away on a work trip, so it was just me.
Staying with my aunt and cousin Hailey wasn’t as easy as you might think. Hailey was flirtatious and playful to the point of driving me mad, and her mom wasn’t much different, just more mature about it.
Hailey and I were both twenty-one, and her mom, Aunt Olivia, was forty-five. They were attractive in very different ways, but Hailey stood out to me the most. She had chestnut hair, porcelain skin, and light freckles across her cheeks. She loved to dress up and cosplay. On my first night there, she came out dressed as Samus. The latex suit fit her like a second skin, clinging to her curves and hugging her modest C-cup boobs. But it was her ass that really caught my attention.
It was big for her size, not overweight, just full and perfectly shaped. High, round, and soft-looking, the kind of ass that bounced slightly with each step. It surprised me, considering she didn’t go to the gym. She only rode horses sometimes, yet she had the body of a fitness model.
That same night, I forgot to close my laptop, and she used it as an excuse to snoop through my browser history. Naturally, she found my saved anal porn collection and just had to tease me about it.
“Geez, I didn’t know you were an ass lover,” she said, flashing me a grin.
“Shut up, Hailey.”
But of course, she didn’t stop there.
A couple of days later, I offered to help clean the house as a thank-you to Aunt Olivia. That’s when Hailey decided to wear a tiny mini skirt with nothing underneath. While I was dusting, she bent over to pick something up behind the couch and called out, “Ryan, can you come here for a sec?”
She was bent at the waist, going commando, and had stuffed a diamond-studded butt plug in her ass. The jewel winked at me from between her cheeks as she wiggled her ass and giggled. “Do you see?”
I rolled my eyes. “What do you want?”
She gave me a sly smile. “Don’t you mean, what do you want? You’re the one with an ass addiction.”
I grabbed a stuffed animal off the couch and threw it at her. “Where the hell did you even get that butt plug?”
“Mom,” she said with a casual shrug. “Feels nice having it inside me. But I bet a cock would feel better. Don’t you think?”
I didn’t answer. We’d always been close growing up, and neither of us had ever been shy when it came to talking about sex. Still, aside from that one time we ended up masturbating together during a family trip, we’d never crossed any serious lines.
For the rest of the cleaning session, Hailey kept finding excuses to bend over in front of me, the jeweled plug glinting every time. By the time we finished, I needed some fresh air.
I grabbed a cold drink from the fridge and headed to the backyard patio. I tried to clear my head, but just as I was starting to relax, my phone buzzed with a notification.
It was a DM from Hailey. I opened it and nearly dropped my phone. She’d sent a video from the upstairs bathroom. The camera panned down her wet body to show a thick dildo buried deep in her ass. She was moaning, pushing it in and out.
“Fuck,” I whispered, feeling myself getting hard instantly. Another message followed, Come see the real thing.
I sat there for a moment, my cock straining against my jeans. How long was she going to keep this up? This game of hers was driving me crazy, but I couldn’t deny I wanted to see more.
When I reached the upstairs bathroom, the door was wide open, of course. Hailey was on all fours in the bathtub, surrounded by mounds of soapy foam, her ass high in the air with the dildo still firmly in place. She looked over her shoulder when she heard me.
“Rate my ass, Ryan,” she giggled, giving it a little shake that made the base of the dildo wobble.
I leaned against the doorframe, trying to pretend I didn’t like her ass despite the obvious bulge in my pants. “Ten out of ten, obviously. But seriously, how long are you going to keep teasing me like this?”
She reached back and slowly slid the dildo out with a gasp. Her butthole gaped open, revealing a pink interior before closing. Then, she turned to face me. The foam covered her breasts, little bubbles clinging to her skin.
“I have a proposition,” she said, her eyes glinting mischievously. “Let’s have a bet. We’ll play Smash Bros downstairs. If I win, you have to give me a full body massage for an hour. My shoulders are killing me after all that cleaning.”
“And if I win?” I asked, though I had a feeling I knew what she was about to say.
“If you win…” She bit her lip. “You get to fuck my ass and come inside me. No condom.”
My cock twitched visibly in my pants, and Hailey’s eyes dropped to my crotch, a smile spreading across her face.
“Game on,” I said. “I’ll meet you downstairs when you’re done.”
“You’ll lose so hard,” she called after me as I turned to leave. “I’ve been practicing!”
I blew her a raspberry and closed the door.
Downstairs, I set up the Switch and tried to steady my nerves. This was crossing a major line, but I couldn’t bring myself to care anymore. I was horny, and there was nothing I wanted more than her ass, especially after she’d been teasing me nonstop since I came here. A few minutes later, Hailey bounced into the living room wearing nothing but a mini skirt that barely covered her ass. She was going commando, and I couldn’t see a bra beneath her top either, typical Hailey behavior.
We selected our characters. I went with Ganondorf while she chose Zero Suit Samus. As we played, she kept trying to distract me, flashing her tits whenever I was about to land a combo or reaching over to rub my erection through my jeans.
“That’s cheating,” I grunted, trying to focus.
“All’s fair in love and Smash,” she laughed.
Despite her dirty tactics, I managed to win the final stock with a well-timed smash attack. Hailey’s mouth dropped open in shock.
“Let’s go to your bedroom,” I said, standing up and adjusting my painfully hard cock.
“Fine,” she sighed dramatically, but I could see the excitement in her eyes as she led me upstairs.
In her room, Hailey pulled a bottle of anal lube from her nightstand drawer.
“Where did you get that?” I asked.
She rolled her eyes. “Mom, duh, she’s just as naughty as me, you know. Reads porn stories all night long while she masturbates. The walls are thin.”
“Now I know where you got your dirty genes from.”
She stuck her tongue out and blew me a raspberry. “You carry the same genes, don’t forget that.”
Rolling my eyes, I quickly undressed, my cock springing free. Hailey’s eyes widened appreciatively as she slid her skirt down her legs.
Her ass was even more perfect up close: plump, smooth, and pale except for a few light freckles. She got on all fours on the bed, looking back at me with an innocent expression.
I poured the lube generously over my fingers and began to circle her tight ring, watching as she shivered at my touch. Finally, I got my hands on her rear, and it was just as soft and bouncy as I’d imagined it to be. I coated my cock thoroughly, knowing we’d need plenty of lubrication.
“You’ve done this before?” I asked, pressing my thumb gently against her entrance, seeing it disappear inside her backdoor.
“Only with dildos,” she admitted. “But nothing as big as you.”
I positioned myself behind her, the head of my cock nudging against her well-lubed rosebud. “Tell me if it hurts,” I said, slowly pushing the head forward against her opening.
Hailey gasped as the head slipped past her tight ring. “Oh god,” she moaned, gripping the sheets. “Go slow.”
I eased in inch by inch, amazed at the tightness. When I was halfway in, I paused to let her adjust. Her breathing was heavy, and she kept clutching the sheets.
“More,” she whispered after a moment. “I want all of it.”
I pushed deeper until I was fully seated inside her, raw, my hips pressed against her soft cheeks. I twitched inside her butthole, and the sensation lived up to my expectations.
“Fuck, Ryan,” she said. “You feel so big inside me.”
I began to move carefully, pulling back and pushing in with shallow strokes. Her body gradually relaxed around me, allowing me to fuck her ass a bit harder and quicker.
“Hmmm.” She kept moving and even started pushing back against my cock.
I gripped both her cheeks, sinking my fingers into them while I continuously thrust into her. I was mesmerized by the way I kept disappearing inside her tight little butthole. The same hole I had been lusting after since the day I arrived. “God, Hailey, I love this.”
“I’m glad. I do too,” she said, arching her back like a sexy cat.
I ran my hands over her glowing cheeks, then grabbed her hips and pulled her onto me as my hips snapped forward. The sound of flesh hitting flesh filled her bedroom. She bit her lip when I pushed deeper, and I found myself doing the same. I pulled out until the tight ring of her ass squeezed the crown of my cock, then pushed all the way back inside. The sensation was almost unreal.
I gave her ass a firm spank and watched my handprint rise on her skin. She gasped, looked over her shoulder, and grinned at me.
“That’s for all the teasing,” I told her.
She giggled softly and kept taking every inch I gave her.
I picked up the pace, my fingers digging into the soft flesh of her hips. The wet sounds of our bodies meeting filled the room, along with our increasingly labored breathing.
“You’re so fucking tight,” I grunted, feeling my control slipping away.
Hailey’s moans grew louder. “Keep fucking me just like that.”
I felt her body tense beneath me, her ass clenching around my cock as she shuddered through what I believed to be an anal orgasm. The added pressure was almost too much to bear.
“I’m coming,” I told her, my thrusts becoming erratic.
She pushed back against me. “I want to feel you come in my ass.”
With one final thrust, I buried myself to the hilt and exploded, pumping stream after stream of hot cum deep inside her backdoor. The intensity of my orgasm left me seeing stars, my entire body trembling. I’d dreamed about this for so long, and I finally got to experience raw anal sex.
When it felt like there was no more cum left, I kept lightly pulling in and out, wanting the sweet friction to last longer. But I became so sensitive that I had to pull out. Her ass gaped open, showing off an interior filled with lube and cum. It trickled over the globes of her red cheeks, red from all the fucking, and then spilled over her the sheets.
“Geeze, what kind of load is that?” she asked.
“Everything you built up with all that teasing,” I told her and lightly spanked her ass again. “But you made up for it now.”
“I’m glad,” she said, and I helped clean her ass with a towel and gave her ass a kiss. “Mom will be home soon … let’s go downstairs and play some Smash … for fun.”
“Sure,” I said, feeling a lot more relaxed now that I had finally climaxed.
To be continued.
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Or if you want to read part 2, click here: Anal Sex With My Aunt