Madison’s free hand snaked down between her thighs and she began playing with herself while she blew me and jerked Jordan off. Man, the sight of my girlfriend’s little sister sucking me off would never get old. I watched as her lips slid down my cock, stopping to hold all of me in her throat before sliding back up so that her tongue could tease the head. I moaned softly. Jordan was right — Madison was really good at giving blowjobs.
I reached down and gripped Madison’s hair, holding it tightly right at the base. She immediately stopped moving her lips up and down my cock and instead held her mouth open; she knew what I was doing. I began to slowly thrust my cock in and out of her mouth, savoring the feeling of her lips tightly wrapped around my shaft. I groaned softly.
“Let’s go to Ashley’s room,” I said, removing my cock from Madison’s mouth. She nodded in agreement.
I turned and opened the bathroom door slowly, peering cautiously into the hallway. The coast was clear. We darted across the hall into Ashley’s room. Jordan was the last to enter; he closed and locked the door behind us. Jordan and I removed our remaining clothes; Madison was already naked. She hopped up on the bed and positioned herself on her hands and knees, arching her back so that her ass was up in the air. Jordan and I got a perfect view of her dripping-wet pussy and her tight little asshole. If only we could take turns pumping that gorgeous, pink pussy of hers full of cum…
“Jesus Christ,” Jordan breathed. I don’t think he ever expected to see Ashley’s little sister in a position like this. Certainly not when she was drunk, horny, and completely naked.
I hopped up on the bed and knelt in front of Madison, who immediately took my cock into her mouth and resumed my blowjob. Jordan climbed up onto the bed behind her. He grabbed her hips and admired the view. Madison’s gorgeous pink pussy and tight little asshole were on full display for him to enjoy. He gripped Madison’s cheeks, squeezing each with his hands before spanking her. He delivered a solid smack to the left cheek, eliciting a soft moan from Madison, before smacking her right cheek even harder. Madison whimpered softly. I know Jordan was just dying to sink his cock into Madison’s warm, wet pussy. How good it would feel to fuck her right now — just pound that tight pussy of hers until we were ready to unload inside her.
Jordan scooted back and knelt down, still holding onto Madison’s hips. Starting at her clit, Jordan slowly traced his tongue up Madison’s pussy.
“Oh fuck, holy shit,” Madison moaned, taking my cock out of her mouth. “Oh my, God.”
Jordan ran his tongue up and down her pussy again, eliciting another moan out of Madison. Jordan gave her ass another smack before running his tongue up to her vagina. He ran his tongue around the outside of her vagina before sliding his tongue inside her. Madison immediately cried out in pleasure.
She looked back up at me for a second before taking my cock back in her mouth. She did her best to blow me, but she was a bit distracted by Jordan’s tongue.
“Y’know, Jordan,” I said after a moment. “Madison is a bit of a slut for having her ass played with.”
Jordan gave me a look that communicated that he understood, or at least that’s how I interpreted the look. And he appeared to get it. Immediately, he moved up from her pussy and began eating Madison’s ass.
“Oh FUCK,” Madison cried out. She was breathing hard now — short, jagged breaths. Jordan ran his tongue around the outside of Madison’s asshole, moving it closer and closer to the center, teasing her.
“Oh my God,” Madison whimpered. “That feels so fucking good.”
Jordan continued to circle Madison’s asshole, allowing his tongue to run closer and closer to her hole itself.
“Please,” Madison whimpered.
Jordan pointed his tongue and licked Madison’s asshole directly for the first time. I watched her eyes roll into the back of her head as she moaned loudly. Jordan darted his tongue back and forth across her asshole now.
Being perhaps a little bold, Jordan pressed his tongue against her asshole, working it inside her a bit. Madison groaned loudly.
“Fuck yes, Jordan!” she cried out as she felt Jordan’s tongue slide inside her asshole. “Lick my ass. Oh my God, fuck yes!” I could see her toes curling back as Jordan wiggled his tongue around inside Madison’s ass.
“Jordan,” I said. “Look in the top-right drawer of our dresser there.”
Jordan got up and went over to the dresser while Madison stayed in position, whimpering, and clearly a bit sad that Jordan’s tongue was no longer in her ass.
Jordan opened the drawer. “Panties?”
“Yeah, rummage around in there. You should be able to find a couple of dildos.”
Madison immediately looked at me and grinned, her prior disappointment vanished.
Jordan looked around for a second. “Oh, I see them, they’re in the back,” he said.
Jordan pulled out two dildos — one a bit larger than the other. He brought them over to the bed and handed them to me.
I immediately handed the small one to Madison, who took it into her mouth and began to suck it enthusiastically.
“Holy shit,” Jordan grinned. “Aren’t these Ashley’s dildos?”
“Yep,” I nodded.
“Holy shit,” he said again, chuckling and shaking his head, likely in disbelief.
Once the first dildo was coated with Madison’s saliva, she handed it back to Jordan.
“Fuck her pussy with it,” I said.
Jordan grinned and lined up the toy with Madison’s vagina. Once the head was aligned with her pussy, Jordan slid the toy inside her.
“Fuck,” Madison breathed, her toes curling immediately. “Oh, shit.”
“Does that feel good?” I asked her.
She looked up at me and nodded. Jordan began sliding the toy in and out of her pussy now, using long, slow strokes at first. Madison moaned softly, enjoying the feeling of her sister’s dildo fucking her pussy.
I handed the larger dildo to Madison. She looked up at me as she took it into her mouth, sucking it in rhythm with Jordan’s fucking of her pussy with the first dildo.
Once again, I had to take a second to take in the sight before me. My girlfriend’s little sister was naked on her hands and knees on Ashley’s bed. She was sucking one of her sister’s dildos while one of my best friends fucked her pussy with another. And we weren’t done yet.
“Alright,” I said. “Try fucking her ass with the one you have there,” I gestured towards the dildo Jordan was fucking Madison with.
Jordan grinned. Madison bit her lip. Jordan pulled the toy out of Madison’s pussy. He aligned the head of the fake cock with Madison’s asshole.
“Ready?” he asked.
“Yeah,” Madison breathed. She bit her lip again as Jordan pressed the toy against her asshole. It only took a second for the head to slide inside her. Madison gasped.
“How we doin’?” Jordan asked.
“Good,” Madison moaned. “I can take more; Brian’s right. I love having my ass played with. I can handle this.”
Jordan grinned and shook his head. I think he was having a bit of a “holy shit” moment too. He slowly slid the rest of the dildo into Madison’s ass until it bottomed out inside her.