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My First Gay Weekend Part 4

"Day two of the craziest weekend ever"

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The craziest weekend of my life continued into that Saturday, when Casey decided to spend the night again. I didn’t know what was coming next, though I knew what I wanted to happen. I had a feeling he did, too. I was glad he stayed.

The Friday night before, we’d watched porn naked together. That led to a 69, and then to him fucking me from behind. When it was all over, we each had cum twice. It was the first time I’d ever been with a man, and I definitely didn’t want it to be the last. But I hadn’t begun to think about what any of it meant, in terms of emotionally. Casey was my best friend, and I didn’t want that to change.

But when it came to feeling anything else for him? It just wasn’t there. While I didn’t know what caused any of our fun from the night before, I was pretty sure it had nothing to do with some sort of unspoken crush. At least not for me.

It was sex. That was all. It wasn’t planned, and we never talked about it, but it was just sex. Okay, it was great sex. That was the only thing I knew for sure.

Casey had a few errands to run early in the day, so I tagged along. We grabbed a quick bite before riding to his mom’s house, where he had to pick up his mail. He’d moved out a few weeks earlier, and was living with a roommate downtown.

The driveway was empty when we pulled in, and I suddenly wondered if that meant something could happen between us again. But I didn't think so. After all, I didn’t know how long we would be alone. I was sure getting caught wasn’t something Casey wanted, and that was definitely true for me.

We went in and I stood in the living room as he sorted through the mail.

“Where is everyone,” I asked.

“Dad and my stepmom are at some craft show uptown, and Dani’s at work, probably.”

Dani was Casey’s eighteen-year-old stepsister. His very hot, big-breasted, eighteen-year-old stepsister. I’d thought about asking her out before, but I was always afraid of Casey objecting to it. Plus, other guys had only made friends with him in hopes of getting close to her.

“Haven’t seen her in a while,” I said.

“She’s the same as ever. Annoying and slutty.”

“Seriously?”

Casey nodded. “Seriously. I mean, it’s none of my business, but my stepmom caught her in bed with different guys a couple of times.”

My cock unexpectedly moved a little at the thought of that. “So what did she do?”

“What could she do? Dani’s eighteen. I mean, I don’t think they’re going to kick her out, or anything.”

I wandered down the hall, and found Dani’s room on the right. It was a mess, with clothes on the floor, an unmade bed, and an empty pizza box on the dresser. She was more of a slob than I was, and I was never known for being a neat freak.

“She’s a bum,” he said over my shoulder.

I stepped in and he followed behind me. “No shit,” I answered. I noticed the black lace thong, among other panties, on her bed. Next to them was a half-empty bottle of lube. “Is she in porn or what?”

Casey laughed, his face turning red as he did. I realized what I’d said, and laughed with him. “My bad.”

We both got quiet for a moment. Without thinking, I moved closer to the bed and asked “So how long is she working?”

Casey didn’t answer. But out of the corner of my eye, I could see him running his hand over the front of his jeans. I didn’t move at first. I wasn’t even sure I could.

The night before was in the dark, and we couldn’t see each other. In some way, it made it not so real. Of course, the soreness in my ass from his cock was real. So was my desire to have him fuck me again.

I decided I couldn’t wait. So I unbuttoned my pants, pushing them down to my knees. I heard him unzip behind me as I stepped out of my shoes and pants. I took my shirt off, slipped off my underwear, and sat on the bed. Casey had already stripped down by the time he stood in front of me.

For the third time in less than twelve hours, Casey’s cock was in my mouth. It tasted so good, and my heart raced as I did it. The thought of getting caught was a turn-on, for sure.

So was the thought of fucking on Dani’s bed.

Casey moaned as I worked on him. Being able to open my eyes and look at his hard cock did make it real and it was so much better than I thought. I loved sucking him.

I started deep-throating him and he propped his left foot up onto the bed. I licked under his cock to his balls and to his ass.

“Mmm fuuck,” he said as I tongued his hole. I didn’t stay long, because I needed his cock inside me again. I was going to turn around for him, but before I could, he went to his knees on the floor and pulled my legs toward him. I laid back on the bed, and lifted my legs up, giving him room to go in. He slid his hands under my ass, and lifted me up even more. He shoved his tongue inside me and my hard cock jerked as he did.

“Oooh goddamn,” I moaned. He kept eating me, his spit and drool undoubtedly making a mess on the sheets. Then he grabbed my cock and started sucking it, sliding a finger inside me as he did. I put my hand on the back of his head and gripped the bed with the other. He held still as I started pushing up, fucking his mouth and moaning louder than before.

He went back to my ass, spreading my cheeks with his hands, and dove in with his tongue again. As my hands touched the sheets under me, I found the lace thong I’d seen earlier. Without thinking, I put them to my nose, inhaling deeply. The smell of Dani’s pussy was overwhelming, and not in a bad way. I suddenly imagined her in the bed with us, riding my mouth, her big tits bouncing, as Casey tongue fucked my ass.

I laid the thong back down and grabbed the bottle of lube. I handed it down to him, and he immediately took it, nearly jumping to his feet. He poured a generous amount onto his cock and then saturated my hole with his hand. I made no move to turn around, but instead, just lifted my legs up, moving in the bed to give him room. Casey took the hint and climbed in, getting between my legs, and resting my legs on his arms.

It was going to be much different than the night before. We would be staring face to face as he fucked me, and we’d be able to see each other the entire time. But at that moment, there was nothing I wanted more.

Unlike the first time he entered me, his hard cock slid in easily, and quicker than I’d anticipated. He instantly reacted, throwing his head back and moaning, “Oh fucking hell.” I lost my breath and gasped, causing him to stop.

“You okay?” Casey whispered.

I nodded. He was already deep inside me, and while it was more than I could take in that moment, I didn’t say so. He must’ve sensed it though, because he remained still for a few moments. He gently stroked my cock, and slowly began moving his own cock back and forth. I wanted him to go faster, but I was glad he took his time. I looked down to watch it all happening.

The sight of his hand on my cock, as he inched back and forth inside me, was maybe the hottest thing I’d ever seen in my life. I was rock hard, harder than before, and I knew he felt the change in his hand.

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“Oh fuck yes,” he whispered.

I ran my hands up and down the sides of his legs as he moved. I closed my eyes and thought about how amazing he felt, and how even on the second time, I was already becoming very accustomed to the sensation of his cock in my ass. At that point, my body had relaxed and my ass was fully accepting him. Without thinking, I clenched my hole around his shaft, causing him to moan in response.

“Jesus,” he said. He pushed forward, lifting my legs up onto his shoulders, and keeping his weight on his knees. He started to go deeper, and I dug my nails into his ass cheeks as he fucked me.

“So good,” I gasped, “ so fucking good.”

He began pushing harder, until he was balls deep inside me. I thought of Dani again, this time wearing a strapon, and shoving her tits, one at a time, into my mouth as she fucked me. Casey was lying on top of me at that point, and breathing into my ear. I ran a hand up and down his back, and grabbed the back of his head with my other hand. He sucked my earlobe, and stuck his tongue in my ear, before coming nose to nose with me.

“I’m gonna cum,” he whispered.

“Fuck yeah,” I said, “do it. Cum inside me.”

Casey pushed harder than before, and after a half dozen loud and painfully satisfying thrusts, emptied his cock inside me. He arched his back as he came, his mouth hanging open and his face contorting as he did it. “Oh fuck, oh yeah, goddamn!”

He kept thrusting, pushing every drop of his hot cum into me. My ass was so sore, but it felt so good, and I wrapped my legs around him as his cock kept spasming inside me. After what seemed like forever, his pace slowed until he finally stopped. He moved back up to his knees and looked down at me. “Fucking hell,” he said between breaths.

Casey slowly slid out, making a near-quiet “pop,” and laid his cock next to mine. I wanted to cum so badly, and started stroking myself. He put his hand onto mine, helping me as I did it. Suddenly he grabbed Dani’s thong from the bed, and wrapped it around his cock.

“Oh fuck,” I laughed. I felt myself get harder, and he stared at me as it happened.

“Is that hot,” he asked.

I nodded, a little unsure of how he would respond. “I guess it’s weird,” I said.

Casey shook his head. “Nah, it’s not. Not for me.” He stopped for a moment before continuing. “I mean, she’s a slut, but she’s not ugly.”

“No,” I agreed. “Plus, her body.”

He stared at me. “I mean, yeah. Her tits.”

My cock jerked at that remark, and I let go so he could stroke it. He started moving faster, and must’ve realized how much I was getting into it. “She’s always liked you,” he said.

“Yeah?”

“Yeah.” His strokes were long, and I could feel his own cock getting hard again. “She wanted to get your number from me, but didn’t want me to freak out. I think she wants to fuck you.”

I didn’t know what to say to that, so instead I just closed my eyes and began to moan as he jerked my cock.

“I’ve seen her pussy,” he said in a half-whisper. “She came home drunk one night and I had to help her into bed. Before I know it, she’s trying to kiss me, and she’s shoving her hand down my jeans.”

I opened my eyes, and waited for the punchline. But his expression was serious as he spoke.

“I pushed her off me, and she pulled up her skirt, yanked her panties to the side, and told me to fuck her.”

“What did you do,” I asked, as his hand moved faster.

“I took my cock out and started jerking off. I didn’t think about what I was doing, I just did it.”

At that point, his cock was rock hard again, and he’d wrapped her thong around it as he jerked us both.

“Did you cum,” I asked.

“Shot it all over her thighs,” he answered, and then he shoved my cock into his mouth. I lost my breath as he did it, and grabbed the back of his head with my hands.

“Oooh fuck yeah, fuck yeah, suck it,” I moaned.

He stopped long enough to look up at me and say “I want you to fuck her, I want you to cum in her pussy.”

“Fuck yeah,” I said, “I want your cock in my ass while I fuck her.”

Casey instantly reacted, and got back into position between my legs. “Goddamn fucking yes,” he said, and he rammed his hard cock back up inside of me. He started pounding my ass, harder and deeper than he ever had. My eyes watered as I took it, and I was moaning so loud I was sure his neighbors would hear me.

He jerked my cock, matching the movement with his thrusts. “Shoot that cum,” he growled, “I need that goddamn cum.”

I couldn’t hold it anymore, and my cock exploded, firing straight up into the air. Casey pulled out, and shoved my cock into his mouth. I mouth fucked him, pumping my cum, causing him to gag as I did it.

“Ohhh fuck, oh yeah, oh god,” I screamed.

“Mmm mmm,” Casey answered as I flooded his mouth. He moved his mouth up and down, swallowing all of it until I had nothing left. He moved up in the bed and turned around into a 69, with his asshole in my face. I greedily ate his hole as he sucked my half-hard cock, and we kept it going for as long as we could, before he finally fell onto the bed beside me.

We lay there for a long while before I finally spoke. “So what happened?”

“With Dani?”

“Yeah.”

“She woke up the next day and didn’t say a thing.”

I was surprised by that. “She had no idea?”

“No. I cleaned her up after she passed out and she never mentioned it. I honestly don’t think she remembers any of it.” He stopped, as if hesitating before continuing.

“It’s fucked up,” he finally said. “What I did, I mean. We’ve never been close, and she’s only been around for three years. So I’ve never actually thought of her as family. But, she is the daughter of my dad’s wife, and that is fucked up. Right?”

I couldn’t exactly disagree with him. But I also didn’t want to just leave him on the hook. “I don’t know if I’m in any position to talk about something being fucked up.”

I wasn’t sure if what I said was too much, or maybe not enough. I also wasn’t sure if the thought of Casey jerking off on his stepsister was crazy hot, or something else altogether. But then again, I’d just told him I wanted him to fuck me, as I was fucking her.

That may have been said in the heat of the moment, but I meant every word of it.

“So,” I said, “nothing like that ever happened with you two before?”

“No,” he answered. He hesitated again. “Well. I mean, we’ve flirted here and there, but I don’t know if she ever wanted anything more than that, or if it could even become anything more than that. The truth is, I—”

The sound of a car outside interrupted Casey, and we both jumped out of bed. We fumbled for our clothes, and my heart was racing. “Shit shit shit,” he cursed as he zipped up his jeans. “Someone’s home.”

I put on my shirt and socks, grabbed the rest of my clothes, and ran to the bathroom. An almost-fully dressed Casey hurried down the hall to the living room as I shut the door, and I finally took a breath as I looked in the mirror. I needed a shower, but it wasn’t happening at Casey’s house. After all, how would I explain it?

I cleaned up as best I could, and once I was finished, I slowly opened the bathroom door. I wasn’t sure who was home, and I didn’t know what would happen next.

Stay tuned for Part 5, coming soon!

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Written by jaycarraway
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