A Weeend Away

John's younger sister was Madi. She was 19 and blonde. The kind of girl who would wear a thong to an EDM concert and post it on Instagram. She was here with a guy, Jackson, who was a nice enough guy. He was short and stocky.

We had all smoked a joint, and still had one in rotation. In the smoky half light, Madi and Jackson were tangled up with each other. I sat across the room, watching Madi's small little hand rub up on Jackson's leg. Jackson was a little, nervous guy, and as Madi stroked him over his pants, his little cock stood straight up. She was still dressed up in her blouse and skirt with tights from dinner; she had unbuttoned her top to let her tits dangle free. As she bent over Jackson, he was too focused on her tits to notice anything else.

But even as Madi was stroking Jackson's cock and letting him kiss her neck, she was looking at me. My friends younger sister looked directly at my crotch, where my cock had been growing beneath my sweatpants. I flexed my cock hard to show her how long I was. I've always been well-endowed, and I knew she was looking. I watched her face as I made my piece jump for her and I saw her mouth open a little bit as she licked her lips.

From Jackson's perspective, Madi was still stroking his cock and he hadn't noticed anything different. But I could. I watched Madi's eyes measuring the cylinder running along my thigh, and then turning back to the tic tac she was running her hands over attached to Jackson. She opened up her legs as she went down to cup Jackson's balls and gave me a wide open view up her skirt to where her stockings ended and where her underwear should have been. But where I was expecting to see underwear, I saw instead Madi's plump pussy lips, shaven and pinched together. I wondered if she knew how exposed she was to me.

When she broke the kiss with Jackson and rolled over onto her back and opened her skirt fell up onto her stomach as her knees spread, there was no way she didn't know what she was doing. She sat up, with her pussy still exposed to me, looked up at my eyes and put her finger in her mouth. She took her hand off Jackson's cock and stood up, walking towards me.

Jackson looked on as Madi walked across the room. She came to a stop in front of me and took her top off. Her tits bounced when they flopped out of her bra. They were firm, full. I admired them as my cock stiffened in my pants.

Jackson said, "Madi, what the fuck are you doing?"

Madi said, "I want to see something. I want to see if he's bigger than you."

Jackson got silent. Madi got a grin on her face as she took a quick glance at the bulge in my pants. "I think we should play a game, Jackson. I know you cheated on me last month. But I don't want to cheat on you, at least not without giving you a chance."

"What do you mean, a chance?" said Jackson.

"You and your friend here," she said, looking down at me, "one of you two is going to fuck me tonight. If you are man enough, you will be able to claim me again."

"I'm not worried, " Jackson said, looking worried.

"To make things fair, I'm going to bring in Allison to judge, so she won't be biased," Madi said.

As Madi left the room to go get our friend, I could see Jackson nervously stroking his cock trying to achieve the hardest erection he could. I remained seated. Allison came back and she was clearly delighted with the task given her. Allison was a lesbian, and was the kind of lesbian who had no use for men at all. She would be quit to point out any male inadequacies, and I sensed she would mock the loser.

Allison instructed both of us to remove our pants. Her eyes followed my hands down to my waistband and then watched as I pulled my cock out. She didn't break her gaze as she examined my full length. Her eyes then turned to Jackson. She sniggered. "I can't believe you think you're the biggest guy Madi has ever been with," Allison said, barely able to contain her laughter.

Jackson turned red and covered his cock with his hands. I put my hands on my hips and pushed forward, making my cock look even larger. Allison grabbed us each by the cock and pulled us close to her. She got down on her knees and took us each in her hands. My piece reached down past her wrist. Jackson's cock barely passed her fingers. Allison grabbed me by the balls and said "this one's bigger."

Madi stood up and approached me. She sat down next to me and casually cupped her hand around the base of my cock and balls. She used her thumb to rub my shaft, though she could not reach all the way to my tip.

Jackson was not done protesting. With his pants still at his ankles and his penis shriveling up with the shame of watching his girl stroke the cock of a larger, better man, Jackson said, "This is bullshit."

At this point, I had enough. I stood up and turned to Jackson. "Go back into your corner, cuck. Madi gave you a fair chance and you lost. You can stay and watch if you want, or you can leave. But don't fucking open your mouth again."

I turned back to Madi sitting with her legs splayed out on the couch, wearing only a skirt with tights. I put one foot up on the couch and thrust my cock into Madi's open mouth. I think I caught her by surprise because she gagged a little bit as I pushed all the way in. I grabbed the back of her head and pushed my cock deeper down her throat. She gagged and tried to push me away from her. I held her down like this while I flexed my cock. Tears welled up in Madi's face as I held her head down on my cock. When I finally released her, Madi inhaled sharply.

"What the fuck dude, you can't do that to my girl, Madi are you alright?" Jackson said as he strode across the room.

I turned to square up with Jackson as he approached me. I punched down towards him, striking him in the bridge of his nose. He stumbled backwards, bleeding. Knowing that Jackson was subdued for a time, I turned to Madi. "Is this what you want? Do you want me? If you say no, I will leave."

"I don't want you to leave," Madi said. She looked at Jackson lying on the ground, bleeding from the nose, and flaccid. "I want you, not him."

Jackson stood mute for a moment, but then Allison snuck up behind him and put her arm around his throat from the back. From this position, she lead Jackson to the wooden rocking chair in the room. She forced him roughly into the chair and bound his hands and feet. He was still naked, and trapped on the chair right in front of Madi and me. For good measure, Allison stuck a ball gag into Jackson's mouth.

"And why is that?" I asked Madi.

"Are you really gonna make me say it?" Madi asked. I nodded, indicating that I would like her to say it. "Fine," Madi said, raising her volume so Jackson could hear, "I want you because I've never seen a cock so big as yours in my life. It's as thick as my wrist, and hangs halfway down your leg. I want you to get in my fucking guts. Jackson, no offense because you're a nice guy, but you just can't hit the deep spots."

After that, Madi started sucking my cock on her terms. She ran her hands up and down my thighs and she dribbled and spat on the head of my cock. She took her thumb and placed it on my frenulum and held tight. She could feel my cock pulsing with each heartbeat. A big smile emerged on her face as she looked down to appreciate my glistening, hard cock. She took it in her mouth again and used her tongue to lick the base of my balls as the tip of my cock reached the back of her throat.

As she sucked my cock, she had her back to Jackson. Now, she stood up and moved aside to reveal my full, glistening wet length to Jackson. Allison leaned into Jackson's ear and whispered: "I'm getting kind of jealous of Madi right now. I bet she's never sucked your cock with that kind of enthusiasm. Only a well endowed man gets to experience that kind of respect."

Jackson struggled against the binds and made a muffled angry response from behind the gag. But, the ropes held firm and we paid him no mind.

In the meantime, I had bent Madi over the arm of the couch. I pulled her luscious ass cheeks apart, to give everyone a view of Madi's pristine undercarriage. Her face reddened from the embarrassment of having her ass and pussy spread open for everyone. The impact of what she had just done: leaving her boyfriend to fuck a well-hung stranger in front of her best friend and now ex- boyfriend. It was all becoming too much.

Right as Madi was about to stand up and call the whole event to a halt, Allison strode over and roughly pushed MAdi's head down. Allison dove head first into eating Madi's pussy and Madi clearly enjoyed it. Her embarrassment of moments ago was entirely forgotten, as Madi arched her back and pushed her pussy up and towards Allison, giving in to her mouth.

Allison's tongue greedily lapped up and down Madi's entire bottom side. She drooled all over Madi's clit and used her tongue to part Madi's lips. And I'm not talking about her face. Allison aggressively drooled and spit all over the younger girl's pussy.

As she did this, she reached down beside the couch, hidden from view from everyone and began to stroke my cock lightly. She winked at me as her tongue went up and down on Madi's pussy. When I was as hard as I could possibly be, Allison stopped and stood.

Madi lay straddling the couch arm with her ass up in the air and her pussy dripping wet from her own juices and her friend's saliva. It was one of the most beautiful sites I've ever seen, knowing that she was this ready for me. Even Jackson started getting hard.

I stood up and mounted Madi from behind. She grunted as I pushed my throbbing tip through her labia and entered her for the first time. I watched her tight pussy squeeze open for me, but she was too wet to keep me out. I pushed myself halfway into her and paused. Madi took a breath and looked back at me. "There's so much left of you," she said with trepidation. "This is as deep as Jackson can reach."

I pushed into uncharted territory deep inside Madi's warm, tight hole. "Holy shit, holy shit" she said, squirming. I took hold of both of her arms and pressed her hard down against the sofa. I felt the tip of my cock pressing up against Madi's cervix deep inside of her. I continued pushing in deeper. Madi cried out, but when I paused, she demanded that I continue.

Finally, with a grunt, I thrusted the entirety of my length into her. I was up to the hilt of my cock in my friend's little sister and she was writhing around in a combination of pleasure and pain as her boyfriend watched. I felt my cock pressing up against her insides and I knew from her reaction that she had never had a cock reach this deep before. I held my hips in place for a few moments, to let Madi adjust to my size.

"I've never had someone so big before," Madi breathed, glancing over at Jackson who was still bound and gagged. For all his complaining, Jackson still had a hard on as he watched the scene in front of him.

I began to thrust in and out, slow at first, and then gaining speed. Madi bit her lower lip in a grimace and bunched up her fists each time I went balls deep into her, but she did not tell me to slow down or to take it easy on her. She began to breathe in rhythm with my thrusts, with her breath quickening as my strokes increased in pace and intensity.

As Madi grew closer to climax, her muscles tensed and I could feel her squeezing me even tighter than she had before. Her chest and cheeks were becoming flushed. Finally, she let out a gutteral roar and she her legs began shaking and her pussy began to convulse around my cock. I could feel her squeezing me and I couldn't hold back any longer. I rammed my cock as deep into her as she could take me, and I began shooting ropes of cum into her depths.

The muscle spasms from her orgasm caused her cervix to open slightly and I knew that I was shooting my cum directly into her womb. I shot six full, thick ropes into her before I was finally spent.

Instinctually, Madi arched her back up to let my seed slide deeper into her. She stayed like that, with my spent cock still buried in her, for what felt like a very long time. Finally, I pulled out. My cock was soaked from our cum and her wetness. Madi stood up and faced Jackson, as a dribble of my cum rolled down her leg.

Jackson looked defeated.

"Untie him," she said to me. "I need a ride home." Madi got dressed as I untied Jackson. He put his clothes on silently and didn't look me in the eye. My cock was no longer hard but it still drooped low and long.

Madi wrote her number down on a piece of paper on my desk and told me to call her sometime. "I'm free any night this week," she said.