Robert’s Second Time by The Great Tash

This story involves non-consensual sex between teenagers. I write this as therapy for some of my own tragic experiences. Please note the genre and themes and move along if this is not in your taste rather than down-voting me and imposing your self-righteous values on my form of therapy.

“Robert, wait up!” I heard Chase yell at me. We had been at his family’s farm this past weekend and had a wild time.

“I heard you got to see Katy nude, boy!” He said grinning at me.

“Yeah, had to. She had to be cleaned up you know? I said grinning and shrugging slightly.

“Bro, you did me wrong. You know I wanted to see those fine ass titties. You should’ve come and got me.” He said putting a hand on my shoulder.

“Man, I’m sorry. It all kind of happened so fast. I’ll have to find a way to make it up to you.” I said to him seriously.

“Alright, man. I believe you will. You’re that kind of friend.” He said.

Truth is, I am. Chase and I had been through everything together. We had been friends since meeting in Kindergarten. Every sexual experience we’d ever had was somehow together. When we were kids we’d learned to jack off together and looked at our first porn together in my Dad’s workshop. We’d fooled around together and sucked each other and even hot dogged each other. We didn’t think of ourselves as gay, maybe we were bi, but we just enjoyed sex and each other’s company and it never got weird. Now, I felt bad because I had done something Chase hadn’t quite yet. Partially that was because Chase was blackout drunk by the time things happened at his party. Partially though, I felt I’d let him down. I’d brought those Freshmen girls to get him laid and it hadn’t worked out.

I may be a country boy, but I’m no dummy. So, I noticed in my AP World class a Freshman boy that was short and fairly attractive. His name was Cary. When he had been sick early in the year, I’d shared my notes with him when he got back and we struck up a friendship. He was a little scared of me, me being both a redneck and a jock, but over time I broached some subjects and got to know the kid. I thought about it and realized that this may be the solution to fix my guilt at not telling Chase about Katy and not getting him his first pussy. I’d get him his first ass.

I decided to invite Cary over on Friday and, although he made a few excuses, I didn’t take no for an answer. I planned everything out and I let Chase know when to come over and hang out in my Dad’s workshop in the back. It would be perfect. My Mom would be asleep in the house. My Dad was out of town doing a job in Kentucky and wouldn’t be home for another three weeks. No one would be there to throw a wrench in my plan.

Cary showed up around 6:30. I went and ordered our pizza and we played call of duty until it showed up. At this point, my plan when into effect.

“Hey Cary, you want something to drink?” I asked.

“Uh sure, Robert, what you got?” He said.

“Crown, Jack Daniels, some kind of vodka. Pick your poison.” I smirked as I said it.

“Uh, I don’t know about that. My parents would kill me if they found out I was drinking…” he said hesitantly.

“Come on, man, you some kind of pussy?” I asked him with a gleam in my eye.

Cary smirked a bit, “I guess not, but you seem to be a bit of an ass…” We laughed together and Cary grabbed the bottle of Jack.

“Got any coke?” I nodded, grabbed his glass and the jack and moved over to the bar to mix him a drink.

We started eating our pizza and drinking. The conversation was wide-ranging. I kept Cary’s glass full and kept him talking. By 9:30 it was time He was nice and drunk.

“Let’s go out in the workshop in the back. I need to check everything is locked down for we turn in for the night anyway.” I said.

As we walked I turned the conversation to sex. I let us in the workshop and we were still talking. Once I was done doing my checks, we went to the little office area where my Dad had his computer and a futon and a couple of chairs. After a bit, Cary got as drunk serious as he could and looked me in the eye.

“Robert, I have a secret.” Cary said. I didn’t say anything. I just held his gaze.

“Robert, I HAVE…a secret.” He said it again.

“I know you’re secret, Cary… and I have one, too” I said to him and I leaned in and kissed him full on the lips.

After a few moments I pulled away. Cary looked at me like a deer in the headlights.

“What… what…” Cary stuttered and was clearly flustered.

“I’m not gay, Cary, but I may be Bi. I like a little of this and that and you’re a super-cute guy.” Cary just kept looking around and at me.

After a while he said, “Robert… I’m not gay or anything. I… um… that was my first kiss and I’m super-uncomfortable now…I’ve got to get going.”

I grabbed him by the arm and kissed him again. Cary kissed me back, I guess not knowing what else to do. My hands explored his chest and moved down towards his hip. I pressed my tongue to his lips and he opened his lips and let my tongue in. We kept kissing and petting coming up for air every now and then. It was hot. Cary thought so, too, I could feel his cock spike up against my stomach and leg as we kept kissing.

I took my shirt off and tugged at Cary’s. He got the point and let me pull his shirt off. I kept kissing him and feeling him up. I let my hand reach down to fondle his package. He wasn’t that big I could tell, but he was a freshman and that was what I had hoped for. A smallish prong with little to no hair. Bon appetite!

I backed off and looked at Cary keeping a hand behind his head. I could see he was a mix of emotions. I decided to go for it.

“Can I see it, Cary” I said softly.

“I’m scared, Robert. No one has ever seen me besides Mom… and what if you tell? being tagged as gay in this town is a life sentence.”

Cary wasn’t wrong. The one kid brave enough to be full out gay was treated like shit by pretty much everyone, but that was my trump card.

“Cary, you know me and the boys ain’t never treated Billy wrong. He eats with us at lunch and comes to our parties. Even if you’re gay, we’d love you. And, I’m about to get naked with you. If you’re gay I’m as gay as you are.”

Cary considered. “Okay, but let’s take it slow. I don’t think I’m ready for anal, but at this point I ave got to cum!

I yanked down Cary’s blue jeans. As I had suspected, not a bad package. A few wisps of hair to be seen, creamy white skin smooth down to a respectable boner for a freshman and wrinkled balls swaying slightly. I took hold of Cary and stoked his cut dick slowly.

“I’m going to suck you, Cary. Will you suck me if I do you? I looked at him expectantly.

“Ah… I’ll try man, but I’ve never done any of this.” He said nervously.

“I’m going to do you. You’ll just do what I do and watch your teeth. Here it goes.”

I am just a bumpkin and not well versed in the art of fellatio as I’ve seen it called on the webs, but I’ve been sucking cock since I was a hairless boy and I’ve never left another man or boy dissatisfied. With Cary, I put in maximum effort. I was swirling my tongue around his shaft, rolling it around the head, and bobbing my head. The boy had little to no experience for sure because it wasn’t long before …

“Rob, pull off!” I, of course, didn’t.

“Rob! I’m gonna…” Cary’s watery, yet large load hit the back of my throat. I held him and didn’t move knowing he’d be super sensitive. After a bit, I sucked a little more to get any of the little bit left. Cary laid back gasping for air. I stood up and unbuckled my belt. Then I shimmied out of my wranglers. I was standing naked in the workshop not for the first time. Cary shucked his jeans as well and set up.

“Let me know if I’m doing it wrong.” He said.

I don’t have one of those comically large dicks everyone tries to describe when they tell these stories. I am maybe six inches full staff. I trim my hair. My balls swing full. Cary opened his mouth and started suctioning.

“Oww!” I said, “let air in, don’t full suction and, OWW, watch your teeth!”

Cary took my advice and kept going. It wasn’t the best blow job, but it was hot knowing I was getting Cary’s mouth cherry and knowing what was about to happen. I was getting close when Chase started walking over. I was so close that I motioned him to stay back and not interrupt as was our plan. I was about to crescendo. I pulled Cary’s head off my dick.

“I’m about to cum, you don’t have to swallow.”

He looked me in the eye, “I want to.”

I held his gaze. “Ok”

Cary got back to work even bobbing his head like I had. It didn’t take long.

“I’m cumming” I said as I released a torrent of jizz into Cary’s mouth. Cary did good with spurt one and two, but spurt 3 ended up on his face and spurt for and five all over his body. It was at this point Chase decided to make his presence known as per our plan…

“What a couple of faggots!” Chase exclaimed.

I stared at him trying to stifle my smile. Cary wiped the cum from his eyes and looked at Chase holding up his iPhone recording with absolute horror.

“This is going to be a hit with the guys at school.” Chase said maniacally smiling. “Y’all might as well kill any plans you had the rest of high school!”

Cary was blubbering and bawling trying to stay quiet. His worst nightmare was being realized. Keeping to the ***********, I played along.

“Chase, what are you doing here. You’re trespassing! We are supposedly friends!” I said doing my best acting.

“You know your Dad is letting me keep my goat here for FFA. And I ain’t friends with no faggot! We ain’t friends if you’re fucking this freshman boy you piece of shit!” Chase could lay it on when he needed to.

“Ok, ok, come on Chase. Is there anything we can do. Hell, I’ll give you the suburban.” I said.

This caught Cary’s attention. Everyone knew I had a spiritual attachment to my suburban. He stopped blubbering and started paying attention to the negotiation.

“You think I want that piece of shit!?!” Chase said. If he has been serious that would have ended our friendship, but he was acting. “I can’t think of anything you can offer that I’d want.”

Cary stood up. “I’ll give you a blowjob. I’ll give you a blowjob and you delete the video.”

Chase just stared and smiled. “I don’t know if a blowjob is enough, but it is a start. Get on your knees, you little bitch.”

Cary hit his knees. Chase dropped his pants and pulled out his cock. Like me, he isn’t huge. He may he slightly longer than me, but I am bigger around. He and I started trimming at the same time, so he was similar that way.

To Cary’s credit, he realized what was on the line and started sucking like someone with a lot more experience. Chase was moaning as he filmed the action. After a bit, Chase reached around and started fondling Cary’s ass. Cary tried to move to avoid it, but Chase got a finger in there. After a few minutes, Chase pushed Cary off…

“Ok, I know what I want that will keep me from spilling. I want your ass, Cary. Turn around on the futon. Robert do you got any lube?”

Cary’s face went white. He started blubbering again. He stood up crying. He turned to me and hugged me, our naked bodies pressing together.

“Oh my god. Robert.” He said. Crying broke the words as he spoke.

I caught his chin, looked in his eyes. “I’ve done anal. It isn’t that bad. He will be done quick and we will be out of this.” I lied as convincingly as I could. “He will ruin us both if we don’t do what he says.”

“Do. Do ya. Do you have any condoms. Dad said I shouldn’t have sex without a condom.” Cary said unevenly, his fear palpable.

“Fuck no, bitch, I ride bareback.” Chase said.

Cary nodded. He was still crying quietly, but he got on all fours on the futon. I opened Dad’s desk drawer and for the KY I hid earlier.

“Prepare him for me, Robert” Chase said.

I took the KY and put it on Cary’s pucker. I pushed a finger in applying as much as I could. I wanted to fuck the boy, not cause him undue pain. I got two fingers in.

I moved and Chase for behind Cary and lined himself up.

“This is probably going to hurt, faggot.” Cary said violently.

Chase, despite the tone in his voice, very slowly and gently put pressure on Cary’s anus. Here we were, the one thing we had been nervous to try together we were going to do with Cary.

“Ah!” Cary exclaimed as Chase’s head gained entry. Chase held up allowing him to adjust a bit. Slowly, painstakingly, Chase’s shaft gained entry to Cary. Cary moaned and grunted in pain, but he took it all.

“Ok, I’m all in. I’m going to stroke a bit. I’ll be cumming in guts in just a couple minutes. This is hot as fuck and you’re getting my virginity, Cary.”

Cary nodded. Chase pulled out slowly and sunk back in slow. He did this motion about 20 or so times. The last time he went to the hilt and grunted as he came hard in Cary’s ass.

He stood up, Cary slunk down off his knees laying flat on the futon. Chase looked at his dick. He looked at Cary’s ass. He smiled.

“Ok, Robert, you’re turn. Get in there and fuck him .”

Cary started to get up to protest. Chase put a hand on his back. “You want that video all over school? You’re going to do what I say!”

Resignedly, Cary laid back down. I mounted him whispering, “I’ll take it easy.” Cary nodded.

There is not a world of difference between a boy’s asshole and a girl’s pussy. If fucking Katy was filet mignon, then fucking Cary was a ribeye. They’re both good, it just depends on what I’m hungry for. I took longer than Chase, and got a little more animated. I kept whispering in Cary’s ear that he was hot and how much I loved his ass. Cary was moaning like a whore. I hadn’t expected him to like it. I came for the second time that night deep inside of Cary. Cary rose up once I got off him and kissed me deep. I was starting to think the kid was in love.

Chase’s laughter broke up our revelry. “Y’all really are some fags.” He slapped his knee. “Here is my phone. Delete the videos and I’ll leave you bitches alone.” I took the phone, forwarded the videos to myself, deleted them off of Chase’s phone, and showed Cary they were deleted.

“Bye.” Chase said as he walked out. Cary and I just sat there naked on the futon. After a bit I looked over and Cary was slowly stroking what must have been a painfully cock. My curiosity was getting the better of me, so I asked him.

“Hey, I know all of this has probably been rough, but you look horny still. You want to try my ass?”

Cary nodded. “I’ve just been raped but yeah, I want to fuck you. You’ve been so sweet to me.”

I laid on my back and held up my legs. He got the KY. Cary slid in easy. It felt pretty good. I guess because he was small and the lube I didn’t get any pain. He hit one spot and I thought I was going to cum again. Cary grunted and shot his load in me. I decided to finish myself off while he was still in me. He saw me stroking and moved my hand away. He stroked me until I finished for the third time.

We got dressed. Went back in the house and went to bed cuddling each other.

The next day, Chase came over.

“That was awesome dude!” He said.

“That it was. And I want more of Cary, but we ain’t fags. We are going to have to get him some pussy so we don’t sissify him”

The next plan was hatched.

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