Being Jenny’s Summer Boyfriend Ch. 03


Disclaimer: this story involves cuckolding, humiliation, cross-dressing, and gay incest.


I have to admit, it was difficult to contain my excitement as Jenny invited my dad and brother over to show them what a little sissy slut I’d become.

To prepare, Jenny let me try on the outfit she’d had on when we’d come over to Andrew’s house: a pink, tight-fitting, girl’s t-shirt that stopped above my belly-button, and a pair of white shorts that I could barely squeeze into. I looked like a cheap boyslut selling himself on the street.

Once I had changed into the appropriate sissy-boy outfit, Jenny, Andrew, Kevin, Steve, and myself relaxed while we waited for my brother and dad to arrive, watching TV. Jenny – wearing nothing but her panties (since I was wearing most of her other clothes) – snuggled up between Kevin and Steve. Andrew, shirtless in just a pair of boxers, let me cuddle up against him. His strong arm groped my ass as I rested my head against his muscular chest.

This is what my dad and brother walked in on: my girlfriend snuggling up against two shirtless jocks, and me, dressed in her skimpy clothes, cuddled against another shirtless jock whose hand was squeezing my tight ass.

“What…the fuck,” was all my dad could say. I was a little nervous – my dad had never been the most open-minded guy, always being super-masculine.

“Um…hi, daddy,” I said softly, biting my lower lip. I knew this was going to end up either with my dad kicking my ass or fucking it, so I tried to be as sexy as possible. I rubbed up and down Andrew’s toned body with my hand and pushed my ass out a little.

My dad looked me up and down. I could see my brother already rubbing his crotch – I knew he would be into this based on how he made me suck his cock earlier. “So let me get this straight,” my dad said firmly. “My son is not only a pathetic cuck, he’s a little sissy faggot.”

I didn’t know what to say, but fortunately Andrew chimed in: “A sissy faggot with the tightest pussy I’ve ever fucked.”

My brother let out a little groan. “Damn,” he said. “You popped his cherry?”

“Sure did,” Andrew said, squeezing my ass. “He’s full of my load right now. Hope you don’t mind sloppy seconds.”

My brother laughed. “Nah, bro, thanks for lubing him up for me. As long as that pussy’s still tight, I don’t care,” he said. He looked over at my dad, who hadn’t taken his eyes off me. “What do you say, Dad?”

“Stand up,” my dad ordered me gruffly.

I did as he said, stepping in front of him. My dad towered over my slim, short frame. I noticed his bulge growing in his jeans. Encouraged, I looked up at him and smiled seductively. “Wanna see what I learned today, Daddy?” I asked.

My dad scoffed at me with a mixture of disgust and arousal. “You look like a fucking whore,” he said, sounding angry but at the same time putting a hand on my bare waist and turning me around to check out my ass.

I turned around completely for him, arched my back, and wiggled my butt. Looking back at him, I said, “Then I guess you should treat me like a fucking whore.”

“Fuck,” said my brother. He quickly pulled his shirt over his head and started unbuttoning his jeans. “I don’t know about you, Dad, but I’m giving this slut what he needs. Get on your knees faggot.”

I quickly dropped to my knees in front of my brother as he took his hard cock out. Staring at my dad, I took the tip of my brother’s dick in my mouth and started licking and sucking at it like a pro.

As my brother moaned and pushed the back of my head further down his cock, my dad still looked uncertain. That’s when Jenny got off the couch and walked over to him, in only her panties. She rubbed her hands up and down his chest, then started unbuttoning his shirt to illegal bahis reveal his bare, hairy, muscular chest. “Mmmmm, I’ve been missing you,” she told him. He smiled down at her, wrapping his hands around her waist, then grabbing her ass firmly. She pulled his shirt off of him, then unbuttoned his pants. He stood before her in just his boxers now, which were tented from the largest cock of any of the guys in the room. She dropped to her knees and pulled his boxers down, cock popping into her face, oozing with precum.

Now my girlfriend and I were both sucking cocks, as the other guys watched and lightly fondled themselves. I looked up at my brother, sliding my hands up his smooth, toned body as I kept sucking. Then I looked over at my dad’s hairy, muscular physique. I wanted nothing more than to feel his monster cock slamming into my tight hole. I was so thankful to Jenny for getting him ready for me.

“How’s that little boyslut doing over there?” my dad asked Jeff.

“Fuck, he’s a natural,” Jeff said. “Watch this.” He gripped my hair firmly with one hand, holding my head in place, then started fucking my face rapidly, his balls slapping my chin. I felt myself gagging on his cock but he kept going anyway. “That’s it, fucking bitch, take that fucking cock,” he groaned.

Finally, he released me and I fell back, coughing and catching my breath. I just looked up at him, smiled, and said, “Thank you for fucking my face like a real man, big brother.”

“Goddamn,” my dad said as Jenny continued sucking him off.

She pulled her mouth off his dick and looked up at him. “Wanna see what he can do for yourself?” she asked.

He could only nod. My brother looked at him and smiled. “All yours, Dad,” he said, then he looked down at me. “I’m gonna fuck your girlfriend while you suck off Dad, okay, Beta?”

“Yes, sir,” I said obediently.

My dad sat down in a chair next to him, then motioned with one finger for me to come to him. Eagerly, I crawled between his legs, reached up, and took his massive dick in my small hand. “Wait,” he said firmly. I looked up at him. “Sniff my balls,” he ordered.

“Yes, Daddy,” I said. I brought my nose to his hairy balls and inhaled his sweaty, masculine scent. I felt my hard cock oozing precum at this humiliation.

Meanwhile, Jeff had stripped off Jenny’s panties and bra and gotten her on all fours on the floor. He slid his cock, wet from my spit, into her pussy from behind. They both let out a moan as he began fucking her.

“I need one of your dicks in my mouth,” Jenny told the other guys. They all looked at each other and grinned, then Kevin got up and started feeding her his cock.

Jenny’s panties had landed on the floor next to me. As I kept sniffing my dad’s crotch, he said to me, “Get those sluttly clothes off and put your girlfriend’s panties on.”

He clearly enjoyed demeaning and humiliating me, and I loved it. I stood in front of him, slid my shirt off, and wiggled out of my shorts. I picked up Jenny’s pink, lacy panties and slid them on, my hard cock poking out of them.

“You like being a good girl for me?” my dad asked.

“Yes, Daddy,” I said.

“I always wanted a sexy daughter I could fuck,” he said gruffly.

“Here I am,” I said, turning around and shaking my ass at him. He reached up and spanked me, and I let out a sexy moan.

“Get on your hands and knees and start sucking,” he ordered. I immediately complied, savoring the taste of his precum before I started bobbing my head up and down, trying to deepthroat him but only getting my head about halfway down his cock. He looked over at Andrew and Steve. “I don’t think this slut’s pussy is ready to handle my cock yet, why don’t one of you loosen him up?”

Andrew grinned at Steve. “I already illegal bahis siteleri dropped my load in him, it’s your turn.”

Steve happily complied, walking over and kneeling behind me. He spat on his hand, but he didn’t need much, as my ass was already lubed up with Andrew’s cum. He was not gentle, quickly slamming his cock all the way into me after pulling my panties to the side.

“Fuck!” I cried out in pain after releasing my dad’s cock from my mouth.

“Shut the fuck up and let him use you, slut,” my dad ordered, grabbing the back of my head and pushing me back onto his cock. He forced my head all the way down. I felt his cock sliding down my throat until my nose was pressed against his pubes. I couldn’t breathe and my eyes were tearing up, but I was proud that I was able to deepthroat him. My hole was crying out in pain, but Steve kept pounding away until I had adjusted. He was doing me a favor anyway, I thought, since I was going to need to be able to take my dad’s cock soon enough.

“That’s it, deepthroat your dad, fucking faggot,” Steve said, slapping my ass.

I could only moan, as my dad was still pressing my head down. He finally released me and I brought my head up to catch my breath. Moaning, I quickly started sucking again, loving the feeling of his rock-hard dick in my mouth.

“Pound him good,” my dad told Steve. “Show him how whores like him deserve to get used.”

“Oh fuck,” Steve groaned. He gripped my ass firmly, so hard that I knew it was going to bruise, then slammed in and out of me as fast as he could. “Fuck fuck fuck, I’m gonna paint your slut son’s fucking insides, fuuuuuuck!” He slammed into me one more time and I felt his cock pulsing.

I heard Jeff laughing. “Goddamn, Steve, you barely lasted five minutes.”

Steve laughed, slapping my ass as he pulled out. “What can I say, this slut is fucking tight.”

“Fuck, I gotta give it a go,” Jeff said, pulling out of Jenny. “Take over for me, bro,” he said to Kevin, who quickly picked Jenny up and tossed her on the couch next to Andrew, spreading her legs and sliding his cock in as she moaned.

“Ready to get fucked by your big bro?” Jeff asked me, pressing the head of his cock against my hole as Steve’s cum leaked out of it.

I pulled my dad’s cock out of my mouth and moaned, “Ohhhh, fuck yes, sir, add your load and get that tight hole ready for Dad’s dick.”

“Nnnghh, you got it, Beta,” Jeff groaned, and slid his cock right into me.

I tongued the head of my dad’s cock and looked up at him. “You like seeing your sons fucking, Daddy?” I asked.

My dad let out a little groan. “He seems to be enjoying your boypussy.”

“Fuck, it feels so good, Dad,” Jeff said, thrusting in and out of me.

“Fuck him good, son,” my dad said. “Show your little brother what a real man feels like.”

“Aw, fuck yeah, Dad, I’m gonna pound this little beta slut like the fucking bitch he is,” Jeff said, slapping my ass.

“You like getting deep dicked by all these real men, don’t you?” my dad asked me.

“Fuck yes, Daddy,” I moaned. “I love getting passed around and used.”

As I tongued the head of his cock, he looked over at Jenny, who was still getting fucked by Kevin while Andrew stroked himself and squeezed her tits. He looked back to my brother. “Bring this slut to the couch, I wanna fuck his girlfriend while you fuck him.”

“Fuck, good idea, Dad,” Jeff said. He pulled out of me and I whimpered at how empty my hole felt.

My dad stood up and walked next to Kevin. “Drop your load in this slut and step aside,” he told Kevin.

Kevin laughed and said, “You got it.” He had Jenny on her back on the couch with her legs spread. He gripped her ankles and started pounding away.

“Ohhhhh, canlı bahis siteleri fuck yes, Kevin, fuck meeeeee, give me your load!” Jenny moaned. Andrew, sitting next her, leaned over and sucked on her tits as she was fucked.

“Nnnnnnngggghhhh!” Kevin groaned. I stared at his cock pulsing into her pussy, remembering how I had pathetically driven Kevin and Jenny home while he fingered her pussy in the backseat.

After he finished, he stepped aside for my dad. Meanwhile, Andrew moved down on the couch to make room for me. He sat at the end and watched as Jenny and I got on our knees on the couch and presented our asses to my brother and dad. My brother quickly shoved his cock back in me while my dad began fucking Jenny’s pussy. They looked so strong and powerful with two sluts bending over in front of them.

I looked over at Jenny. She was moaning like crazy. “Oh my god, don’t stop, don’t stop, you’re so big,” she cried.

“Mmm, yeah, you like that big dick?” my dad asked, squeezing her ass.

“Ohhh, fuck yesss,” Jenny moaned. “I don’t know if your son’s gonna be able to handle it!”

My dad laughed. “I don’t give a fuck,” he said. “If he’s gonna dress up like a little girl slut, he’s gonna take my cock whether he likes it or not.”

I felt a pang of nervousness, but let out a moan. I felt Jeff give my ass a squeeze as his thrusts intensified. “Fuuuuck, you ready for another load, Beta?” he groaned.

“Fuck yes, big bro, fill me up good,” I moaned.

He slammed into me and I felt the familiar pulsing of a cock dropping its load.

After he pulled out, I kept my ass in the air and wiggled it seductively for my dad. He continued fucking Jenny, looking over at me and saying, “I’m gonna make your little girlfriend cum before I get to you.”

He bent down, engulfing Jenny’s small frame, wrapping his arms around her to squeeze her tits, and pounded her pussy intensely. Her moans became screams of pleasure like I’d never heard from her. “Oh god oh god oh god yes yes yesyesyesyesssssssssssssss!” Her body shivered under his weight and she collapsed into the couch from the intensity of her orgasm.

My dad pulled out of her, slapped her ass, and said, “Fuck yeah.” Then he quickly moved over and pressed his massive cockhead against my hole.

“Ohhh, be gentle, Daddy,” I begged him, a little scared.

“Fuck that,” he said and slammed himself into me all at once.

“FUUUUCK!” I cried, my ass screaming out in pain. “Stop, stop, it hurts!”

My dad just shoved my face into the couch, pulled out the full length of his cock, and slammed it back in. I could only groan in pain into the couch. “This is what little pussy boys deserve,” he groaned, holding the back of my head and beginning to fuck me roughly.

I felt my hole stretching from his thick cock, and eventually the pain subsided and I started to moan in pleasure. He released my head and I moaned, “Ohhhhh, yessssss, fuuuuuck you feel good, Daddy, thank you for making me your bitch, fuck me harderrrrrr!”

My dad laughed and slapped my ass. The other guys hooted and clapped at my dad’s performance. “You better like it, because this is how you’re getting used the rest of the summer, fucking whore.”

“Yessssss, Daddy, fuck me whenever you want!” I cried. I felt my cock rubbing against my panties. “Keep going, I’m gonna cum, I’m gonna cummmmmmm!!”

I shot my load into my panties and onto the couch. “That’s it, shoot your load from that worthless cock,” my dad taunted. “Here comes Daddy’s load in your ass.” And with that he gripped my butt firmly and pumped the biggest load of the day into me. We all collapsed and lay down, exhausted.

The rest of the summer went about how you would expect. Jenny and I were routinely passed around among my brother and dad and her friends. My dad also started inviting his work buddies over to fuck me and her as well. I learned how to be an obedient cockslut, which served me well when I went to college and got used by all the frats and the football team.

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