“You want me to do what?” Maddie asked.
“I want you to peg me,” I replied. “You know, put on a strap on and fuck me in the ass We’ve been talking about it for years now, but we’ve never actually done it.”
“When you won this bet, I thought I was the one who was going to be taking it in the ass,” Maddie said. “It’s been a while since I let you fuck me there.”
“I know, but this is what I want,” I said. “We have everything we need, dildo, harness, lube. Hell, we even have a book about it.”
“Okay. When are we doing this?”
“Right now,” I said. “if you’re up for it. I have everything laid out in the bedroom already.”
“Okay. Let’s go,” she said. “I’ll fuck your ass.”
Maddie led the way to the bedroom, giving her hips an extra bit of swing with each step.
“Are you sure you don’t want my ass?” she teased.
“Oh, I definitely do want your ass,” I replied. “But, first things first.”
“Okay, you butt slut.”
“What can I say?” I said with a shrug. “I like what I like.”
We got to the bedroom, where I had laid out a swirly purple medium-sized dildo, a black leather harness, and a bottle of lube.
“You’re always thinking ahead,” she said.
“I am,” I replied. “You love that about me.”
“Yes, I do. Now get those clothes off and get your ass up in the air!”
I smirked and took off my clothes, tossing them into the hamper. Maddie did the same.
She placed the dildo through the opening in the harness and stepped into it.
“If you want to get fucked, come here and help me get this adjusted,” she said.
I moved to her and helped her tighten the buckles on the harness and get the dildo positioned comfortably.
“How’s that?” I asked.
“Good,” she said. “Now, suck it.”
“Suck my cock,” Maddie ordered. “You get yours sucked before you fuck me. Why shouldn’t I get the same?”
“I guess you have a good point.”
I moved to my knees and licked the head of the dildo, then ran my tongue along its length before taking it into my mouth. I worked it in and out of my mouth a few times trying to take it deeper, just like she does with my cock. She grabbed my hair and pushed the dildo further into my mouth until I gagged on it.
“Fair’s fair,” she said.
She pulled the fake cock from my mouth and said, “Get on the bed. Lie down on your side.That’s supposed to be more comfortable, especially the first time.”
I laid down on my side and pulled one leg up toward my chest.
“Good boy”, she said. “Let’s get you ready.”
I could hear the click of the cap as she opened the bottle of lube. A moment later, I felt the cool lube dripping onto my ass. Another moment and I felt her fingers rubbing around my asshole.
“Just breathe and relax,” she said. “We’ll take this slow.”
Her fingers caressed the ring of my asshole, and I sighed as I relaxed into the feeling. One of her fingertips teased my opening gently.
“You like that, do you?” Maddie asked.
“Yeah, I do. Keep going.”
Her finger slowly slid into me and she began to move it in and out slowly.
“Yes. More, please”.
She dribbled a little more lube and slipped another finger inside my ass. I groaned this time, as I adjust to the added size. She started fingering my ass a bit faster.
“Can you take one more?” She asked. “Then you’ll be ready to get fucked.”
“Yes,” I said. “Do it.”
She had three fingers inside me now, more than I’ve taken in a while, but I was loving every moment of it.
“Mmmmmm, yes. Fuck me, please”
“You wnat me to fuck your ass?” Maddie asked.
“Yes, please. Please fuck my ass.”
Maddie slid her fingers out of me, but soon I felt the head of the dildo pressing against my bud and she steadied herself with one hand on my ass, while the other guided the dildo into my ass.
She pushed slowly, allowing my ass to adjust to the size, giving me slow short thrusts that steadily grew deeper. I could feel the dildo deep inside me now, and I felt her hips against my thighs.
“Wow! You took that whole cock,” she said.
“Unnnngggg,” I groaned.
“Is it too much?” she asked.
“No, fuck me.”
“Beg for it slut,” she said.
“Please fuck my ass with your cock,” I begged.
“Well, since you asked so nicely.”
She gripped my hips and started thrusting into me, slowly, steadily, and deeply.
“Yes, yes, yes,” I panted.
“You like that, slut?”
“I love it!” I said. “Keep fucking me.”
She moved faster inside me.
“Are you going to cum from this?” Maddie asked.
“I have no idea, but it feels amazing. Don’t stop!”
“I kind of like this,” she says as she keeps fucking me.
“So do I,” I replied. “We should do it more often.”
“I’m getting a little tired, though. Fucking is hard work,” she says with a chuckle.
“I’ve told you! You’ll get used to it, but your thighs are going to be sore tomorrow.” I said. “We can pause for now.”.
Slowly and gently, Maddie eases herself out of my ass.
“Did you cum?” She asks.
“No, but my cock is leaking like crazy.” I replied. “I’m all sticky.”
I rolled over and showed her my cock, covered in pre-cum and stiff.
“You weren’t kidding,” she said. “You really loved that.”
“I did. I want some more,” I said. “Right now.”
Maddie smirked and replied, “Greedy little slut.”