“Yes Brian,” she said. “That was incredible.”
“Mine was too.”
“I’m glad,” she smiled, still breathing hard. “You came a ton. I guess you really like having your balls played with, huh?”
“Duh.” I laughed. “And it seems you like playing with balls.”
“Duh,” she said, mimicking my tone. She grinned. “Let’s do this again sometime?”
“Yes please,” I said.
“I’m actually going to go to bed now,” she laughed. “Make sure you put those pictures to use sometime soon.”
“Oh, I honestly wouldn’t be surprised if I jacked off again today,” I said.
“Neither would I.” She got up slowly. “I think I’m gonna try putting a finger in my butt tomorrow morning. I know I’m going to wake up super horny after what we just did.”
“Sounds good to me,” I said. “Let me know how it goes, okay?”
“Of course,” she said. “After all, I gotta get my booty to the point where it could take something like that.” She gestured towards my cock.
“Yes, you do.” I agreed.
She walked over to me and hugged me. I’m almost ashamed to admit it, but feeling her naked tits against my chest made me hard again. It didn’t help that I could feel her wet panties against my leg either.
“Good God, does that thing ever quit?” She said, giving my dick a quick tap on the head with her finger. She gave my balls a very quick squeeze before breaking our embrace.
“Not when there’s a hot, naked girl in front of me.”
Madison blushed. “Well, I’m not naked. But fair enough.”
I stared unabashedly at her tits for one last moment before looking back up at her face. “Goodnight, Madison.” I sat down and and opened my phone, pulling up the photos I took of her. I began to stroke myself, figuring I could come one more time and then have enough time to recover so I could fuck Ashley when she got back.
Madison laughed, “Goodnight, Brian. Have fun!”
“Oh, I will,” I grinned. I watched Madison’s ass as she walked away.
If I remember correctly, I came to the photo of Madison on her elbows and knees. If only she wasn’t wearing any panties in that photo. I cleaned myself up and laid on the bed in Ashley’s room until she got home. Once she was home, she came in and said “hello” before hopping in the shower. She came back into her room with her hair in a towel and nothing else on.
“Hey, just so you’re aware, Madison and I masturbated together a couple of times today,” I said.
“That’s fine,” Ashley said, sitting down next to me. “Honestly, you don’t need to tell me every time you guys masturbate.”
“Okay,” I said. “We also did a little more than that, though.”
“Oh?”
“The second time we masturabted, she reached up and massaged my balls while I finished on her face.”
Ashley laughed. “Good God. You both must’ve loved that.”
“Are you upset?”
“No!” Ashley said. “I don’t care. Do whatever you want with Madison. Alyssa too. I don’t care if you play with them since you’ve already given me permission to do the same. Nobody else though, obviously.”
“Sweet,” I grinned. “Madison did say she was going to try playing with her butt tomorrow.”
“Oh yeah? Are you involved with that at all or…?”
“Well, not exactly. But she did say that she wanted to get her ass to the point where it could handle something like my dick.”
“Wow, she said that?”
“Essentially, yeah.”
Ashley looked amused. “She’s getting bolder.”
“No kidding.”
“And no, I wouldn’t care if you fucked her in the ass,” Ashley said, answering my next question before I even asked it. “Like I said, you can play with her as much as you want.”
I laughed. “Yeah, that was going to be my next question.”
“Obviously,” Ashley giggled. “Man, I bet you can’t wait for her to be ready for your cock.” She pushed me back and crawled on top of me. She reached back and took ahold of my dick, which was completely hard by this point, and aligned the head with her pussy. She sank down onto me, slowly taking me inside of her. We both moaned loudly.
“Well, you seem excited by the idea yourself,” I groaned as she began to ride me.
“The idea of my sister being fucked in the ass by my boyfriend? Yeah, that’s hot,” Ashley moaned.
“Would you want to watch?” I asked. Ashley braced herself on my chest and began to really bounce her ass up and down on my cock. I could tell she was already close to her first orgasm.
“Obviously,” she groaned. I reached up and grabbed her tits as she bounced on my cock. I ran my thumbs over her nipples, eliciting another moan out of her. “Ideally I’d like to participate.”
“Maybe she could eat your pussy while I fucked her ass,” I grunted. Ashley’s cunt was really milking my cock.
“I’d like that,” Ashley cooed as I bottomed out inside her pussy.
“And maybe you should help her,” I said. “I think she’s nervous about putting even a finger in her asshole.”
“Yeah, I’ll offer to help her,” Ashley moaned. I began fucking her harder, thrusting into her as she rode me. “I don’t know if she’d let me touch her asshole or anything, though.”
“Maybe not,” I said, “but it’s worth a shot.”
“Oh fuck,” Ashley cried out, “I’m coming, don’t stop fucking me Brian, oh my GOD!”
I felt Ashley’s pussy throbbing hard around my cock as she climaxed. She was already incredibly wet before coming, but now her pussy was soaked. It took everything I had not to come inside her.
Once she finished coming, she shifted forward, allowing my cock to slide out of her pussy. I immediately knew where this was going. Ashley smiled at me as she reached back and positioned my cock against her asshole. She sat back down onto me and her ass readily swallowed my cock.
“Oh fuck,” I grunted.
Ashley had a look of pure bliss on her face as she sank all the way down onto my cock. We both sighed as I bottomed out in her ass.
“Just let yourself come,” Ashley said, biting her lip. She braced herself against my chest and began to bounce her ass up and down.
I moaned loudly, “Holy fuck!”
I reached forward and held Ashley’s hips as she bounced her asscheeks on my cock. She moaned loudly, savoring the feeling of her ass being fucked.
“I’m gonna come, baby,” I groaned. “Fuck me, oh my God!”
“Fill my ass with your cum, daddy,” she cried, riding me fast and hard.
My cock exploded inside her, painting the inside of her rectum with my jizz. I gripped the bed sheets as her ass milked my cock, extracting every last drop of semen from my balls. Ashley groaned loudly.
I sighed as my orgasm finished. Ashley slowly rose up off of me. She quickly ran to the bathroom to clean herself up, returning with some tissues with which she cleaned my cock. We cuddled there for a moment before getting up to brush our teeth and go to sleep.
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