Disclaimer: this story contains cuckolding and homosexuality. All characters are 18+ years old.
***
My best friend Jeff and I were halfway through our senior year of high school. We'd both just celebrated our 18th birthdays, and we were starting to feel a little lame that we were still both virgins. We were obsessed with girls - talking about which girls at school were the hottest, who had worn the sluttiest outfits that day, all that kind of thing.
Naturally enough, we had discovered porn together, starting out by sharing our favorite clips with each other. Then I started to come over to his house sometimes and we'd watch it together in his bedroom. It had been a little awkward at first, but we were both so horny that we would jerk off together, commenting on the girls in the videos. Jeff would say stuff like, "Fuck yeah, I'd love to cum all over those big tits," all while vigorously stroking his very impressive, very thick, 8-inch cock. Not having anything to be embarrassed about, he would take his shirt off and just whip his cock out in the open as he stroked. But mine was only 4 inches, so I would usually just reach into my underwear and stroke it like that, not wanting Jeff to see. Of course, he could still tell I wasn't packing much - one time, I noticed him glance over at me as I came, a stain growing in my briefs, and he scoffed at me a little bit as he slid his hand up and down his long, thick cock. Then he returned his attention to the porn and shot his load all over his bare, muscular chest.
Jeff had an athletic build developed from his time on the water polo team. He should have been able to get a girl by this time, but he spent a lot of time studying. He was going to be the valedictorian of our class, and had been determined to get into a good college, so he just hadn't focused much on girls until now. But now he'd been accepted into a good school and he could focus his attention on finally losing his virginity.
I, meanwhile, spent my time in the drama club. Girls seemed to like me and even flirt with me, but I was pretty shy when I wasn't performing on stage, and it had just not worked out with any of them yet.
One day, Jeff and I walked back to his house from school, knowing his parents were both at work and we'd have time for one of our jerk-off sessions. That day, a girl named Jenny had been wearing a spaghetti-strap top that showed a little bit of her flat stomach, and a pair of tight denim shorts. She had big tits that were barely contained by her top. Our teacher had almost made her go to the office and call her parents to bring in a new outfit, it was so distracting.
"Whatever, he probably liked the show just as much as we did," Jeff joked.
I laughed. "Totally," I said. "Did you see how he had to keep sitting behind his desk to hide his boner?" It was true - I had noticed our teacher's large bulge grow in his pants once he saw what Jenny was wearing.
Jeff laughed. "Dude, me too. I had to hold my books in front of me every time I stood up."
When we got to Jeff's bedroom, he pulled up Jenny's Facebook page to check out some of her photos. They weren't super-revealing or anything, but you could see her figure, and she had a really sexy face.
"Goddamn, she's so fucking hot," Jeff said, rubbing his erection through his jeans.
"Yeah, dude," I said, unbuttoning my shorts and sliding my hand into my briefs.
Jeff slid his shirt off, revealing his toned chest and abs, then unbuttoned and unzipped his jeans and pulled his big dick out. Every time he did this, I couldn't help but glance over in awe at his powerful tool. "Those pretty little lips would look so good wrapped around this, wouldn't they?" he asked, staring at his computer screen.
My eyes stayed on Jeff's cock. I pictured Jenny on her knees in front of him and groaned. "Mmm, fuck yeah, they would," I said.
Jeff looked over at me staring and smirked a little. "Think she could take this whole thing down her throat?" he asked, stroking his cock up and down slowly.
I smiled shyly, a little embarrassed at being caught staring at his dick. "I dunno, dude, it's pretty fucking big," I said.
He laughed a little, then released his cock and let out a frustrated sigh. "Fuck, dude, I'm so tired of feeling my own hand all the time!"
I laughed too. "I know. You should ask Jenny out, I bet she would say yes."
"Yeah, maybe I will," he said thoughtfully. Then he looked over at me and caught me looking at his erection bouncing up and down on his abs.
I looked away and laughed a little. "Sorry, dude, I'm not gay or anything, I'm just picturing Jenny sucking you off," I said.
Jeff laughed. "It's okay, bro, I get it," he said. "You think she would need two hands to get all the way around this thing?" He held his dick lightly at the base so that it was sticking straight up in the air.
It was true, I thought - his cock was very thick. I stroked myself inside my underwear. "Fuck, she probably would, that's so hot."
A sheepish little grin developed on Jeff's face as he seemed to get an idea. "Um, dude, not be weird or anything, but, like..." He hesitated.
I smiled, curious what he was thinking. "What?" I asked.
He shook his head. "Nah, nevermind, it's too weird."
I laughed, now very intrigued. "Come on, what is it?" I pressed.
He laughed and said, "Nothing, I was just thinking, like, you're probably about the same size as Jenny."
I stared at him, processing this thought - it was true, I guess, both Jenny and I were pretty short. After a second, we both burst out laughing. "Sooo, what does that mean?" I asked, still laughing.
"Nothing, just, if you...ya know...touched it, it would probably feel about the same as if it was her," Jeff said.
"Oh my god, dude," I said. "You're fucking gay."
"No, it's not gay," Jeff protested. "I'd be picturing her."
"Whatever," I said dismissively.
Our laughter died down, and a certain kind of tension formed between us. Jeff clicked through some more photos of Jenny, finding one of her sticking her tongue out and wearing a tanktop that showed off some cleavage. Jeff gave his cock a light stroke up and down, glancing over at me. "Seriously, though, dude...I'm so tired of feeling my own hand..."
I looked over at him. "Are you...serious?" I asked quietly.
"Yeah, dude," he said, a little nervously. He leaned back in his chair, his cock bouncing in the air. "Just...touch it a little..."
I don't know what came over me, but there was a certain energy in the room, and I felt my hand reaching over to lightly grasp Jeff's dick. Sure enough, my small hand didn't quite reach all the way around it.
"Damn, I was right," Jeff said. "Looks like you need both hands."
I looked at him. "You better not tell anybody I did this," I said firmly.
"Dude, I won't," Jeff said. "Go ahead, just stroke it a little."
Slowly, I reached over with my other hand and held Jeff's erection in my hands. It had been lubed up by Jeff's spit, and I began sliding my hands up and down.
Jeff let out a groan. "Fuck yeah, that feels good, keep going," he said, staring at the picture of Jenny.
I moved my hands down to the base of his dick, then slid all the way up and back down. I couldn't help but be impressed by the feeling of his huge cock in my hands - it felt...powerful. I felt a pang of jealousy that this is what Jeff got to feel in his hand all the time.
As I kept stroking him, I suddenly felt something press against the back of my head, and looked up to see Jeff had reached around and was pushing my head downward. "What the fuck, dude?" I objected.
"Come on, please," Jeff said in an insistent whisper. "I'm just gonna be looking at Jenny's picture the whole time. I swear I won't tell anybody. Just do me a favor."
I felt his hand pushing the back of my head again, and, weirdly, I found myself unable to resist. Before I even realized what I was doing, I felt the tip of his dick press against my lips, then started taking him into my mouth.
"Fuuuuuck yesssss, wrap those pretty little lips around my fat fucking cock, you little slut," Jeff groaned. I looked up at him, stunned, and saw him staring intensely at Jenny's picture.
Something about the pleasure I was giving him triggered something in me, and I felt my own cock oozing precum into my briefs. I pushed my head as far down Jeff's cock as I could, then pulled my head back up and started licking his shaft up and down eagerly.
"Oh fuck, that feels so fucking good," Jeff said, clearly feeling a level of pleasure I'd never seen him experience before.
I felt Jeff's hand grasp the back of my head firmly and I started bobbing my head up and down on his cock. I didn't really know what I was doing, but I could hear his moans escalating, so I guessed I was doing okay. Intensely turned on, I reached down and started stroking my own cock as I kept sucking.
"Fuuuck, Jenny, don't fucking stop, I'm gonna cum down your throat," Jeff groaned. He was still looking at her picture.
As Jeff's moans reached their peak, I felt my own orgasm building. Suddenly, I felt his cock pulsating in my mouth, and his load hit the back of my throat. He held my head firmly on his cock for a few seconds as he kept shooting his load, then released me. As I felt the last few drops of his cum hit my tongue, I let out a moan and came into my briefs.
After it was over, I looked up at Jeff. We were both clearly embarrassed at what had just happened. I stood up and tried to quickly pull up my shorts, but he clearly saw the large wet spot on my briefs from my orgasm.
"Looks like you enjoyed yourself," he said, smirking a little.
"Whatever," I said, feeling myself turning red.
"Um...thanks, dude," he said.
"Uh...yeah, no problem," I replied. "...I guess I'm gonna head home now..."
