Senior year was a total blast. We got treated like royalty at school and basically ditched a lot of classes and went into Westwood for two hour lunches and all that. I was really going to miss all my buddies, especially Jake. He stuck it through with me since the sixth grade when I was a total outcast because I was short and had braces. Ok, so now I was 6'2" with perfect teeth, a pretty good body, your basic blond haired, blue eyed all American. No one could laugh at me now. But the important part was that Jake never did. He was there every step of the way like a true buddy. I even met my girlfriend, Catelyn, through his girlfriend, Elise. Because they were basically the hottest girls in school, we got props for that too. I guess we were pretty popular.
Anyway, all senior year the four of us partied together and went on, what the girls called, "double dates." Elise would sneak out bottles of wine from her dad's cellar. Jake brought the weed. He had a connection with a skateboard kid from Echo Park. Elise provided the wheels. She had a huge van because her brother used to be a musician. When he went off and got married he gave her the awesome set of wheels. I always joked with Jake that it was a hotel room on wheels. Well, that was the idea.
We had two weeks left until graduation. After that we would all officially split up. I would stay in California and go to UCLA. Jake would go to Boston University. Elise was heading to Berkley. And Catelyn was doing an overseas program in Scotland.
So, the big talk in our little group was about losing it. Well, Jake and me talked about it lots. And I know the girls talked about it because every once in a while one of them would slip and tell us what the other had said. Kind of strange in this day and age that all four of us were virgins, but hey, at least we were still under eighteen (just about).
So, with two weeks left together the virginity discussion was starting to get more heated. "Elise says that Catelyn's starting to come around. She says if Elise and me do it, she'll think about giving it up to you," Jake informed me.
"Awesome. So do you think Elise is going to do it with you?"
Jake's smile was golden. "Dude, she just bought a box of condoms." We high-fived each other.
It was really about time. I was sick of sneaking out to the bathroom to whack off every time Catelyn and I went out. And there was no way I was going to college a virgin. If Catelyn backed out now I would just have to hire a 'ho or something. I was reaching the end of the line.
Jake convinced me there was no need to worry. He was meeting with Elise later that afternoon to discuss "plans." This may sound weird to anyone but us four, but that's the way we did things, like a little community, a group. We did everything together. "I think the idea is to aim at next weekend. Elise and Catelyn's parents are working on some fundraiser together. They're going to be real busy, too busy to notice missing booze and the girls staying out past one."
"Cool."
"We're talking about going over to The Peak." The Peak was this legendary place where everyone had a "first time." Some people took acid up there. Other just had sex. Jake was saying we could take sleeping bags out there and switch off between outside and the van.
Two days later it looked like the plan was in order. Jake was waiting for me by my locker. He looked real good today so something must have been going well. He had color in his cheeks and his deep blue eyes glittered with excitement. "Four days, man. We're going to be getting some in four days. It's all set. Friday night, we all go up to The Peak. I'm bringing some vodka from my dad's liquor cabinet. Catelyn says she's going to need to be tanked up or she'll be too nervous."
"That's fine, that's fine. I don't give a shit if she's falling all over the floor."
When Friday night came I was so nervous and excited that I almost threw up. I had to keep going over a checklist that Jake had made for us: alcohol, cigarettes, weed, condoms... Oh, and part of my own check list was that I had bought a pair of those Calvin Klein boxer briefs that all the girlies love so much. Catelyn was going to be so excited when she undressed me. When I heard the van roll around at nine I bolted out the door so fast it wasn't even funny.
Catelyn looked really cute. She bought a sexy new black dress for the night. She couldn't keep her hands off me in the car. Our lips were practically glued together. I couldn't wait to give it to her. Elise was being pretty affectionate with Jake too. She kissed him at every stoplight. "You know kissing send me over the edge," I heard Jake whisper to her. She kept rubbing his leg too while she was driving. I could see that this really turned him on because he popped a boner. Well, I don't know if he knew that I knew that but I saw it out of the corner of my eye. Then I popped a boner. I guess just the idea that my buddy was getting excited made me more excited. It was all that team spirit sinking in.
When we got to The Peak, Elise parked the van in a pretty far away spot, away from the line of Dead heads who were regulars. The girls got out of the car first and went to go set up the sleeping bags.
"I'm so horny, I can't wait for this to happen, Jake."
Jake opened a beer and took a swig. "I know dude, I didn't even jerk off today. I wanted to be able to come a few times." He handed me a beer. "We got to get them started with the alcohol or they're going to be nervous all night."
"They don't look too nervous." We looked over and saw the girls joking and laughing.
"Oh, they're nervous alright. Elise told me when I got in the car."
"I left the van open, by the way, in case one of us wants to slide in there, if you know what I mean."
"Hey man, I got first dibs on the van, ok?"
I reluctantly agreed since he was the mastermind behind this whole plan.
With that we brought the two grocery bags full of alcohol over to the girls and just started drinking like crazy. The two girls polished off a bottle of wine each and were taking big swigs out of the vodka bottle. We were pretty drunk too but, you know girls, they have a really tough time handling their alcohol. I looked over at Jake and winked. He knew what I meant and helped Elise up and the two of them walked over into the van.
I couldn't believe it. My best buddy was going to do it, now! I quickly got to work on Catelyn. We made out for what seemed like forever. My dick was so hard I thought I was going to spunk all over my underwear any second. Speaking of which, I couldn't wait for her to check out my new Calvins. I undid her top. She was stripped down to her bra. I moved my hands all over her tits. She moaned. Then I moved her hand down to my crotch. This was it, the moment. Or was it? Catelyn's hand froze.
"Ryan, I don't feel so good."
"What's wrong?" I asked.
She was swaying from side to side. "I think I'm going to yack or something." She made a run for the bushes and I heard the sound of her throwing up.
When I walked over to check on her she was passed out, face down. I slapped her cheek lightly but she just grumbled.
"Hey, Catelyn, wake up, this is our big night."
"Let me sleep or I'll kill you," she mumbled.
I couldn't believe this was happening to me. I still had a semi-woody and nothing to do with it. I too hadn't whacked off all day and was about to have the worst case of blue balls in history. I was going to go jerk myself behind a bush when; I'm ashamed to say my curiosity got the best of me. As I got close to the van, I kept expecting to hear moaning sounds or to see the van start to rock. I thought, at least if I wasn't getting any, I could here a sample of what I was missing. But, instead, all I heard was, "Fuck, shit..." Jake was saying that. When I looked inside the van I saw him in his underwear with Elise passed out in his lap.
"You too, man?" I stepped into the van. "Catelyn just yacked and passed out in the bushes."
I sat down next to Jake. He lifted Elise off of him. "Help me get her in the front seat." We both moved her and she didn't even wake up. Pretty soon we were just kicking back drinking our beers in the back of the van.
"I can't believe this cunt," Jake said, as if she wasn't even there. He didn't even try to hide the fact that he was in his underwear. I guess he was really pissed off.
"Shhhh, she'll hear you."
"No way man, you don't know Elise. When she passes out, that's it for the night. Stone cold, out. She doesn't hear a thing. It's like she's dead or something."
"Were you guys really close to getting it on?"
"She was about to give me head when she passed out. It was pretty hot. She was so drunk she was talking dirty and stuff, telling me she wanted to deep throat my stiff cock."
"Wow, that sounds really hot. I was getting wood just feeling Catelyn up. She had her tongue rammed down my throat for so long I thought I was gonna shoot right then and there." Just then I noticed something weird happening. This sex talk was getting me horny again. I had a full-blown stiffy.
Jake looked down at my pants. "Looks like you didn't get very far either."
I looked down at Jake's crotch, which I noticed was starting to swell. "So are you. In fact, I was about to go jerk off in those bushes. This is pretty bad. We've get to get rid of these hard-ons."
"Shit, you're right." He moved his hand over his crotch and made a face like he was in pain.
"You're not gonna get too far with that."
"No shit." He started massaging it. He wasn't looking at me, probably on purpose because he was embarrassed. He kept touching himself. I was getting harder too.
I unzipped my pants and stuck my hand down them feeling my pulsating dick. "Ahhh," I sighed in relief. Just then Jake looked over at me. "Yeah, it feels good to finally have it be touched."
"Sure does." I couldn't keep my eyes off his dick. I don't know why but it really fascinated me. Maybe it was the alcohol or just the weird circumstances. He was trying to hide it with his hand but I could still see its full girth. I guess he felt me staring at him because he turned his head finally and looked at me. It was an intense moment; two best friends hard and ready for action but with no ready girls to be found. I closed my eyes and stroked my dick, pretending it was Catelyn's hand. But suddenly in the middle of the fantasy I started to imagine Jake's hand moving up and down on my throbber. It freaked me out so I quickly opened my eyes. Jake was starting straight at me and tried to pretend he wasn't by quickly looking away.
"I was just pretending it was Catelyn's hand," I told him.
"Yeah," he said rubbing his dick, "I'm pretending it's Elise."
"Is it working?"
"Kind of, but it never feels the same when it's your own hand."
I wondered if he was trying to get at something with that comment. "Sure, I know what you mean. It would feel good if it weren't my hand."
"We could just..." Jake looked uncomfortable. "Nah, forget it."
"What?"
"You're going to think it's weird."
"Dude, we've been best friends since sixth grade. Just say it."
"Well," he looked like he was about to choke, "If we just close our eyes we can, uh, you know, help each other out. Then we could think of our girlfriends but it would feel good."
It seemed pretty logical at the time. But I was basically thinking with my dick, which at this point was still hard as a rock, and even felt like it was growing. "Hey, it sounds cool. Let me just get these off." I pulled my pants off so I was also in my underwear. "Cool underwear," he said, just under his breath.
All the sudden I felt my buddy's hand was nervously sliding up my leg and over my dick. I was kind of nervous too. I slowly reached over to feel his hard boy meat in my hand. I can't even explain how good it felt to have another guy's cock in my hand. It was weird but just so, I don't know, taboo, I guess. I felt really bad. I liked feeling bad. I looked over at Elise passed out in the front seat and got even more into it, moving my hand up and down his rod, as he did the same on mine. I had to stop his hand a couple of times because I knew I would come. At one point we both moved around so we were almost facing each other as we jacked each other off.
We were both breathing really heavy when all of the sudden Jake started leaning forward. "Dude, don't get freaked out, I just need to be kissing to get off, ok?"
I nodded, in awe of him. Then I felt his lips on mine. We opened our mouths. As soon as our tongues touched I was in heaven. I guess I had secretly wondered what it would be like to fool around with him. His tongue was hot and sweet as it flicked over mine. It teased mine until I finally started sucking it. Pretty soon Jake was on top of me grinding his cock against mine. I was so drunk and horny that I just let myself do whatever came naturally. I slid my hands over his round, muscular ass and massaged it. What an amazing ass. I could fuck that, I thought to myself. What was I thinking? Fucking a guy in the ass, my best friend. My dick had taken over.
I grabbed at his ass hard and ground him into my crotch. He started moaning now. He was obviously really into it too. Still kissing him, I started to slide his underwear off. He moved his lips away from mine and then took them off completely. His cock was so wide and beautiful and hard. Without even thinking I just leaning in and starting sucking at the head.
Jake's hands grabbed the back of my head. "Oh yeah, buddy, that's it. Your mouth feels so good. Suck that cock."
I got brave enough to put a little more down my throat. Pretty soon the head was tickling the back of my throat. I gagged a little. When I did, Jake spasmed.
"Take it all in, Ryan."
He thrust his teen rod into my mouth in perfect rhythm. His hands grabbed at my hair. His moaning became louder and louder. "Oh, dude, if you don't stop that, I'm gonna...." Then I felt it. That warm salty flavor of spunk dripping down my throat. Believe it or not, it tasted fine. I swallowed the whole load. I was hornier than fuck now, with the residue of cum taste in my mouth. I got up and stared at him.
"Man, that was the rockin-est head anyone's ever given me," he said.
"Thanks."
"I'm sorry I came in your mouth."
"It's ok. You taste pretty good, actually." I leaned in and forcefully French kissed him letting him taste his own spunk. Then I gently ran my hand over his ass almost smoothing my fingers into the crack. I also let my tongue run up and down his neck, gliding it over his Adam's apple.
"Don't think I'm a fag or something, but your ass is really fine." I squeezed it a little more.
"Thanks," he said blushing. "It's cool, we're men. We can say that kind of stuff to each other. We're brothers, you know."
I smoothed my hand over it. I saw that he was getting hard again from all this attention I was paying to his hot little boy butt. He kind of turned around, like he wanted me to see it. I turned him around completely. I gently spread his ass cheeks and lightly moved my finger over his hole. He gasped. I'd never looked at another guy's asshole before. Even in the dark I could see that it was tight and sexy. He got on his hands and knees, like he was giving me access or something. This was like the greatest temptation. I really wasn't being myself because I suddenly just leaned in and started licking and nibbling on his ass cheeks. He moaned. He had the fucking hottest ass I'd ever seen. I just wanted to devour it. All the sudden, before I knew it, my face was between those perfect ass cheeks and I was flicking my tongue over his cherry hole. He moaned uncontrollably. "Oh, dude, I've never felt this good before. Oh, it's so hot." Licking his pucker was better than I could have ever imagined. It was so sensitive and I found out, so tight as I stuck the tip of my tongue inside it. "Yeah, man, stick your tongue up there. God, that's fucking amazing." His ass was really relaxing so I alternated with my finger. He moaned even more. Then another finger. Now he had no choice in the matter. Whether he liked it or not, he was going to be fucked.
"How'd you like to feel something else up there?" I asked, rubbing my hard cock against his butt cheeks.
"I'm scared, man." He sounded like a child.
"I'm not going to hurt you. I'll do it slow."
"I don't know."
I leaned in and rimmed his hole again. He moaned. Then I rammed my tongue in it deeper than before.
"Fuck man, that's so hot," he said.
I got up. "Yeah, well, just imagine my cock filling it up entirely." My finger trailed down to his ass crack again.
"Slowly," he said.
I grabbed him by the waist and inched him over to my crotch. I was about to pop my best friend's ass cherry. I was about to lose my own virginity inside his butt. "Jake, dude, you're my best friend. I'm gonna be the first to fuck your tight hole."
"Yeah, oh yeah," he said, backing up, practically begging for my cock to fill him.
I spread his ass cheeks and rubbed the head of my cock over the tight opening. "Oh, yeah, do it, don't wait any longer," he whimpered. I'd never seen him act this way--so submissive. I just wanted to fuck his little pucker raw. As I slid my cock in I heard him say, "oww." "Should I stop, man?"
"No, just do it really slowly." I did as he said and slowly slid my 7 inches into his ass hole. With every inch he begged for more. He was so tight, I thought I would shoot at that moment. My cock was just surrounded by his tight, wet, warm asshole. It was pure ecstasy. "Your hole is so tight, bro. I'm gonna try to fill it." I thrust in. Pretty soon I was thumping and pumping into his ass, feeling it surround my cock. On his hands and knees begging for more, my best buddy was at my mercy. "You little pussy boy, you feel so good," I smacked his ass.
"Oh yeah, you're filling me up Ryan, so good." We were gaining momentum and the feeling of his soft ass cheeks against my crotch was sending me over the edge. "Dude, this is it. I'm gonna shoot my load inside your tight ass."
He ground back forcing my dick to go deep inside him. "Oh yeah, I want to feel you cum inside me, baby."
"I'm doing it, bro, oh," I said unable to control myself. It must have hurt him because I thrust so deep inside that boy that I couldn't possibly have gone any further. The next thing I knew I was filling his butt with my huge load of spunk. "Fuck man, I'm cumming in your hot ass."
It was like the most intense orgasm I'd ever had. I leaned back for a second, wiping the cum off on my T-shirt. I was finally just lying down with my head propped up against my rolled up pants, against the door. Neither or us said anything for a couple of minutes. Those were deadly moments. I don't think either of us really thought about all this and it had suddenly happened. But, Jake was still hard. That had to be the only thought in his mind as he started crawling towards me with his swelling cock. I just sat there, amazed at how big and beautiful it was. Before I knew it my buddy had his knees on my shoulders and was straddling my head. His teen pole just kind of slid into my mouth. I just couldn't help but start sucking on it. Pretty soon he was pumping it in and out of my mouth. Jake was fucking my mouth. It was incredible. He breathed heavily and moaned and just gyrated his hips like a total pro. "Oh Ryan, your mouth feels so good. Take my cock. Suck me."
I just wrapped my lips around his member, almost afraid to let go; I didn't want this ecstasy to end. But then I felt that amazing warm trickle, oozing down my throat. A little even dribbled out the side of my mouth. My boy had unloaded his second round of spunk down my throat. Before we could even high-five each other we heard what sounded like Elise rustling in the front seat. We managed to act fast enough to get our underwear on. I actually got my pants on too. "Fuck," Elise whined.
Just then, in total crazy timing, Catelyn poked her head in the van. They both stared at us with confused looks on their faces. God, I didn't know how I was going to explain this one. I looked over at Jake but he was equally confused.
Catelyn looked me up and down. "Oh my God, Ryan, did we finally do it?"
Elise's eyes widened. "Jake? Was I so wasted that I actually missed my first time?"
Jake looked at me knowingly and then back at the girls. "What can I say. It was better than I ever imagined."