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 ankara otele gelen escort 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…”
“Yeah, sure, see you tomorrow.”
I fled his house in a hurry, trying to process what I öveçler escort had just done.
***
The next morning, a Saturday, I slept in late and woke up to a text from Jeff reading, “OMFG dude I got a date with jenny!!”
Groggily, I texted back:
Me: wait what?
Jeff: yeah dude! / after you…ya know…I decided to message her and ask her out tonight and SHE SAID YES!!
Me: wow…congrats dude
Jeff: so pumped / thx again for yesterday btw
Me: um yeah sure don’t mention it
Jeff: now I’m about to get the real thing lol!!
Me: lol…u think she will?
Jeff: fuck I hope so / I mean if I got you to do it I should be able to get her to do it lol
Me: um yeah I guess / but…could you maybe not bring that up anymore?
Jeff: lol don’t be embarrassed bro / u should be proud, u almost took the whole thing
Me: srsly dude stfu
Jeff: aww ok ok sorry dude
I rolled my eyes at his teasing and put my phone down, only to realize I had a raging hard-on. I sighed and figured it was just morning wood, and reached down to start jerking off. As I did, images of Jeff’s cock started flashing into my mind. It didn’t take me long to cum.
***
I didn’t hear from Jeff for the rest of the day. But the next morning he texted me again:
Jeff: dude u won’t believe it
Me: how did it go?
Jeff: amazing
Me: oh? u get any?
Jeff: well I’m not one to kiss and tell…
Me: lol come on dude
Jeff: ok ok…I FUCKED HER
Me: WHAT??
Jeff: swear to god
Me: holy shit / what happened
Jeff: I went out with her and then drove her back to my place after I knew my parents would be asleep / and she was saying she wasn’t sure she wanted to come in blah blah / but we made out in the car for a while / and I felt her up / and she started rubbing my crotch
Me: damn
Jeff: and when she felt my dick she said “oh my god” and her eyes got all big and she immediately agreed to come inside
Me: r u serious
Jeff: completely…she’s a total slut
Me: wow…so then what happened
Jeff: …u stroking?
Me: …maybe
Jeff: lol I knew it
Me: whatever keep going
Jeff: ok ok so we sneak into my room and she’s immediately on her knees whipping my dick out, and she can’t get over how big and thick it is, she literally said “I’ve never seen one this big” lol
Me: shit she is a slut
Jeff: for sure b/c she definitely knew how to suck a dick…I mean, u were good, she was great
Me: ok yeah whatever
Jeff: lol…so after a while, I told her to get on all fours on the bed and…well…not sure I should show you this but…
Me: show me what?
Jeff: …
Me: did you fucking record it???
Jeff: lol…it’s possible I set my phone down and accidentally hit record…
Me: omg
Jeff: u wanna see?
Me: lol do I wanna see one of the hottest girls in school getting fucked? hell yes bro
Jeff: lol ok here ya go…have fun…
Jeff then sent a clip of Jenny, her slim body on all fours getting pounded from behind by Jeff’s big dick. They were both glistening with sweat, and she was moaning like crazy, begging for him to keep going, saying she’d never felt anything like this before. Eventually he flipped her over and slid between her legs, making out with her and sucking on her tits as they fucked. I couldn’t believe this was Jeff’s first time, he looked like a porn star. I had to keep myself from cumming several times, but when I saw her body start to shudder and tremble and Jeff held a hand over her mouth as she orgasmed, I couldn’t hold back and shot my load.
***
That Monday, talk was all over the school that Jeff and Jenny were together now. I saw girls huddling around her in the hallway giggling, and guys high-fiving Jeff. I also noticed a lot of girls started looking at Jeff differently, always glancing down at his crotch and biting their lower lips in desire. He would just smirk and wink back at them – it was clear Jenny had told all her friends about his amazing performance, and that he could now have any girl in the school he wanted. But he was sticking with Jenny – he walked down the hall with her, his arm around her waist.
I was happy for my best friend, of course, but I also couldn’t help but feel intensely jealous of him. I had spent Sunday alone watching the video he’d sent me on repeat, jerking off so many times my dick started to feel raw. All the while I knew he was probably out with her, maybe fingering her in his car or making her deepthroat his big dick.
Jeff started spending more time with Jenny and less time with me, but he still kept me in the loop. He would text me details on what he did with her, how desperate she was for his cock, how good it felt to be inside her. Every now and then he’d send me a short clip that he managed to record. I would jerk off like crazy to all of it.
The three of us started also hanging out together, getting food or going pendik escort shopping before Jeff and Jenny would disappear together. They were so blatant with their affection in front of me – it was kind of annoying, but also a big turn-on. Jenny had begun wearing more and more revealing clothing, and Jeff naturally couldn’t keep his hands off of her. One time I was driving the three of us to the mall and they sat in the back seat so they could just make out the whole way, and I could tell from her blatant moaning that he was fingering her.
“Sorry about that, Lucas,” Jenny told me once we got to the mall. “I hope that wasn’t too awkward for you.”
“Oh, um, it’s okay, don’t worry about it,” I said shyly to her.
She smiled at me and touched my arm lightly, causing a jolt of electricity to go through me. “You’re such a sweet best friend to him,” she said.
“Um, yeah, thanks,” I said.
***
Now that Jeff had a girlfriend, he tried to encourage me to find one as well, telling me how great sex was and how I needed to get laid. But a lot of the girls I was interested in already had boyfriends, or I was too shy to approach them. Then one day, Jeff told me that Jenny’s best friend, Emily, had broken up with her boyfriend and was newly single. Emily was gorgeous – light brown hair, perky tits, a round little butt. Jeff said he and Jenny were going to be hanging out with her that afternoon and he would try to put in a good word for me.
I was so excited – this might finally be my chance to lose my virginity! I spent the afternoon daydreaming about the prospect of Jeff and I dating two of the hottest girls in the school. But then I got a text from Jeff:
Jeff: bad news bro / she’s not interested
Me: what??? why??
Jeff: ummm I mean it’s not really important / but it’s a definite no
Me: fuck
Jeff: it’s ok bro we’ll find you somebody else who’s a better match
Me: what did she say? please tell me the truth, I need to know
Jeff: well…she said she thinks ur gay
Me: WHAT?!
Jeff: she just gets that vibe from u
Me: I’m not fucking gay! Tell her!
Jeff: I mean…u did seem to enjoy…ya know…
Me: omg you didn’t tell her about that did you??
Jeff: no of course not dude I’m not a complete asshole
Me: ok thx…can you please tell her I’m not gay? you know I’m not! we talk about girls all the time, we used to watch porn together…
Jeff: I tried to tell her all that / she said she can tell by the way you look at me
Me: what???
Jeff: I mean, it’s totally okay if you are, bro, none of us would care
Me: I’M NOT!!
Jeff: ok ok
Me: are u still with her?
Jeff: yeah
Me: u have to convince her
Jeff: um…she and jenny are both a little busy right now if u know what I mean lol
Me: …r u serious?
Jeff: fuck yeah dude
Me: dude that’s so fucked up, she was supposed to be my girl!
Jeff: I swear I didn’t make a move bro / I really tried my best to get her to go out with you / but after she said no u really expect me to turn this down?
Jeff sent a picture of Jenny and Emily, topless and on their knees, both of them grinning and licking Jeff’s cock. I texted back:
Me: fuck…I guess not
Jeff: lol Emily just said u prob want to be down on ur knees with them
Me: what the fuck?? no I wouldn’t that’s so fucked up
Jeff: lol like I said it wouldn’t be a big deal if you did…could even make it happen…
Me: jesus christ jeff NO I’m not gay / that was one time
Jeff: ok well plenty of fish in the sea, we’ll find one for ya / ttyl gotta paint these sluts’ faces
I looked back at the picture of Emily and Jenny on their knees and started stroking myself, imagining them hungrily licking at and sucking on Jeff’s cock, then getting sprayed with his big load. I came in my briefs in no time.
***
That Saturday, my parents were out for a date night while I lazed around playing video games. Just then, there was a knock on my front door. When I opened it, there was Jenny, wearing a denim jacket, a button-up blouse, and a pair of white shorts. She looked furious.
“Jenny!” I said, surprised. “What’s the matter? Are you okay?”
“Hey, Lucas. Can I come in?” she asked.
“Uh…sure,” I said.
She stepped inside. “Are your parents home?” she asked. I told them they were out. “Good,” she said. We sat down on the couch in my living room, and she turned to me. “Your best friend is a fucking asshole,” she said angrily.
“What?” I said. “What did he do?”
“He fucked Emily behind my back. Cheating bastard.”
“Oh my god, uh…” I didn’t what to say. “But, uh…I thought…all three of you…”
“Yeah, yeah, I know he sent you that pic of us when we gave him a blowjob together,” she said. “But that does NOT mean I gave him permission to fuck her when I wasn’t around.”
“I…uh…how do you know that he did?”
“Um, maybe because I fucking walked in on her straddling him in his bedroom!” she said angrily. “That little fucking slut.”
“Oh…wow…” I said. “I’m…I’m so sorry…”
“I’m so fucking pissed!” she exclaimed. Then she let out a sigh. “Could you get me a glass of water?”
“Uh, sure, no problem,” I said. “One sec.” I hurried to the kitchen to pour her a glass of water.