“Fuck, that feels so fucking good,” Madison moaned.
“It looks so hot,” Jordan said. “Do you want me to fuck you with it now?”
“Yes please,” Madison whimpered.
Jordan slowly slid the toy back out of Madison’s ass, stopping with just the head remaining inside her. Madison moaned as Jordan slid the dildo back inside her all the way. I watched as Jordan began to fuck Madison’s ass with long, smooth strokes.
“Holy FUCK,” Madison groaned. “That’s so good. Fuck yes, Jordan, that feels so good. Fuck my ass, holy fuck!”
I took the second, slightly larger dildo from Madison and handed it to Jordan.
“Fuck her pussy with that one,” I said.
Jordan took the toy from me and nodded. Without slowing down the fucking of her ass with the first toy, Jordan slid the other dildo inside Madison’s pussy.
“Oh my GOD,” Madison cried out. She stuffed her head into the bed and moaned loudly as Jordan began to fuck her pussy with the second dildo.
I walked on my knees around to the side of Madison partly so that I could get a better look at my girlfriend’s little sister being DP’d by Ashley’s sex toys. Madison’s pussy lips gripped the larger dildo so tightly, and watching her take that fake cock made my desire to fuck her even worse.
Madison reached back and began rubbing her clit as Jordan slid the toy’s in and out of her ass and pussy. He had a good rhythm going. As he slid the larger dildo into Madison’s pussy, he was pulling the smaller one out of her ass. Likewise, as he slid the smaller dildo back inside Madison’s ass, he slid the larger toy out of her pussy. And she was clearly loving every second of it. I knee-walked back in front of Madison and she immediately took my cock into her mouth. She sucked it gently. I think she just wanted to have all three holes filled.
Madison moaned loudly as she held my cock in her mouth. Her breathing was quickly becoming more rapid.
“Don’t stop,” I told Jordan. “I think she’s gonna come.”
Jordan maintained his rhythm, loving the sight of Madison’s pussy lips and asshole gripping the sex toys as they were thrust in and out of her body. I watched as Madison clutched the sheets hard with her free hand. She cried out as loudly as she probably could have given my cock was in her mouth.
“She’s coming,” I said. Jordan kept fucking her two holes with the toys as Madison’s entire body began to shake. She moaned loudly, still holding my cock in her mouth, apparently determined to orgasm with all three holes filled. Jordan and I just watched as she spasmed and convulsed in front of us. Jagged moans escaped her lips in between gaps for air. Jordan never let up on the toys; he continued to fuck her pussy and her asshole with them hard and fast through Madison’s orgasm.
When Madison’s climax finished, I hopped up and grabbed a towel from Ashley’s closet.
I handed it to Jordan. “For the toys,” I said. Jordan nodded. He slowly slid the larger dildo out of Madison’s pussy and placed it on the towel. Next, he slid the smaller toy out of her ass and placed that on the towel too. He wrapped them up slightly and placed the towel on the floor next to the bed.
Madison collapsed, basically panting. I rubbed her back. Jordan squeezed her ass.
“You ever have an orgasm with all three holes filled before?” I asked, grinning.
“Nope,” she breathed.
“How was it?” Jordan asked.
“Fucking amazing,” she said, breathing hard. “I’ve had plenty of orgasms with something in my butt or something in my pussy, but not both at the same time, and definitely not with a cock in my mouth too.” She took another second to catch her breath before saying, “but I think it’s y’all’s turn to cum again.”
“What do you have in mind?” I asked, a little hesitantly.
“Well,” Madison grinned. “My ass is all warmed up and ready. I think it’s about time I took a real cock up there.”
“Holy shit,” I said. Jordan’s jaw dropped a little. “Are you sure? We can just stick to blowjobs or something. We don’t care.”
“No, I want your cock inside my ass, Brian,” she said, looking me in the eye. Then she turned and looked at Jordan. “And yours too.”
I didn’t say anything for a second. I was trying to contemplate her proposal, but I was admittedly a little too drunk to think clearly. And the horniness was getting to me a bit too, obviously.
“My pussy is still off-limits,” Madison said. “But there’s no reason both of you can’t enjoy my ass.”
“Okay,” I said. “If you’re sure.”
“I am,” she said, biting her lip. “I want to feel you both shoot a load inside my asshole.”
“Holy shit,” I breathed. “Fuck yeah, let’s do it.”
Jordan looked at me and grinned. “You got it first, man,” he said, stepping aside.
Madison rolled over so that she was on her back. “Gimmie Ashley’s pillow,” she gestured at me.
I gave her the pillow. She lifted her butt up in the air and positioned the pillow underneath her so that her ass was elevated a bit.
“Oh, that’s a lot better,” I said. She was in a much better position to take my cock in her ass like this. I took a moment to appreciate the sight before me: my girlfriend’s little sister, completely naked, legs spread wide open. Her cute little nipples stood completely erect, and her pussy glistened with juices from her last orgasm. Below that was her tight little butthole, my target.
Jordan tossed me the bottle of lube. My cock was already soaked with Madison’s spit, but I squirted a healthy glob of lube onto my shaft and rubbed it in a bit, just to be safe. I wiped my hand off on one of the towels, and then shifted forward.
“Are you ready?” I asked her.
She nodded, pleading at me with her eyes to get my cock inside her already.
I shifted forward and aligned my cock with her ass so the head was pressed right up against her hole. Madison whimpered softly. I pressed forward some more, and her ass immediately gave a little, allowing the head of my cock to enter her.
“Oh my God,” I moaned as I watched my cockhead disappear inside Madison’s ass for the first time.
“Fuuuuck,” Madison moaned. “Oh my God, Brian. You’re finally inside me. Fuck.”
Madison reached down and began to play with her clit as I slid more of my erection inside her. Her asshole gave some resistance, but the work Jordan put in earlier helped warm Madison up, and I was halfway inside her without too much effort.
“How is this?” I asked her. “Are you okay?”
“Yes, this feels fucking amazing,” she purred. “We should’ve done this a long time ago. It feels so good to finally have your cock inside me.”
I held still for another moment, relishing the sight of my cock halfway buried in her ass. Jordan was shameless stroking his cock to the sight of me sodomizing my girlfriend’s little sister.
“I can take all of you, you know,” she said softly. “That was always the goal, wasn’t it?”
I chuckled and nodded. I grabbed onto the sides of her stomach and thrust the remainder of my cock inside her. The two of us moaned loudly as I bottomed out inside her. My balls were resting against her ass cheeks, and I enjoyed the feeling of her tight ring gripping the base of my cock. Madison’s fingers were already speeding up as she worked herself towards another orgasm.