Tales of Dick Ch. 03: Come Undone

***Everyone in this story is fiction and is at least 18 years old or older***

Before you read this, I am deeply sorry for the delay on chapter 3. I had issues writing this chapter. I'm hoping people enjoy the finished product.

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Chapter 3: Come Undone

Panic! Was the best word to describe what Jason was feeling right now. He was walking back and forth in my room, like a distressed chicken. It was kind of cute. I had offered him a cup of coffee, but he turned it down. He said he wasn't a coffee drinker. I sat on the bed, with my back against the headboard, enjoying my cup of coffee. I've never seen anyone this worried before, I felt bad.

I should feel bad.

I'm the reason why this kid is in trouble. I figured maybe I could help solve the problem. I sipped my coffee while thinking of a solution, it then hit me.

"Hey, How about I call your mom?" I asked, breaking his pacing.

Jason turned to me placing his hands on his hips, waiting for my plan.

"I'll call her, tell her that my younger brother is part of the team and after practice, I took the two of you out for pizza and a movie. Then since it got late, you both stayed over."

"That would work if I didn't tell her that I was at my friend Terry's house," Jason said.

That was true. I paused and then spoke once more.

"What if, you and my brother were at your friend Terry's house. I went to pick him up but you needed help with your homework, so you stayed over here."

Jason thought about it. After a few seconds he said, "Yeah, that might work."

It would be a small little lie but it would get the job done. With that, I told him to call his mom. When she picked up Jason handed me the phone. I spoke with her in the most respectful and professional way. I had plenty of experience from talking to customers and parents of customers. After a few minutes of talking she was convinced and would pick him up in 30 minutes. I handed him back the phone and gave him a thumbs up. Indicating that it went according to plan.

I clapped my hands. "Now, let's go get me a brother," I said.

"Wait, you don't have a brother?"

"I do, but he's 21 and in the Marines."

"But why you need to get a brother?"

"Wouldn't it be better for you to be walked out by my brother?"

"Yeah, true that."

Now that that was dealt with, I needed to borrow someone. Lucky for me one of my customers lives down the street. His name was Vince, he was 16 and was a pretty cool kid. I would call upon for some favors at the shop. Not sexual ones, of course, simple tasks like heading to another shop for me or getting me food. I told Jason to stay in the house while I jogged to Vince's house, which was only two blocks away. When I arrive at Vince's house, I knock on the door, after a few minutes Vince opens the door. He had a slim body similar to Jason's. He wore a long t-shirt and some baggy shorts.

"Sup Vince," I say to him.

"Hey Richard, what's up?" Vince says to me with a drink in his hand.

"Want to do me a big favor?"

Vince leaned his shoulder against the frame of the door and raised a brow, "Continue"

"I need you to pretend you're my younger brother."

"For what?"

"It's best we don't get into details, I'll pay you."

"50 bucks" Vince demanded.

"25" I replied.

"45"

"30"

"40 or nothing."

I couldn't believe what this little shit was doing. When I would send him on

errands I would pay him a few bucks, the most I had ever given him was $20. But I needed him, so I folded. Plus I didn't want to go throughout my neighborhood looking for a kid to play my little brother.

"Fine, $40," I said.

The kid smiled, "Alright, when do we start?"

"Now."

Vince and I walked back to my apartment, I told him the plan and what had happened. I left out that Jason and I had sex. He knew I was bisexual but he never gave me flack for it. I gave him $20 and told him he would be paid the rest after the job was done. When the time came, it paid off very well. The two of us walked Jason to his mom's car, we both said hi. She thanked me for taking care of him, but before she left she asked me a question.

"Do I know you from somewhere? You look familiar."

"Maybe from the skate shop down the street," I replied.

She laughed, "Oh that's probably it. Well you have a nice day and thank you once again"

Jason and his mom drove off.

I handed Vince the remaining $20, "Here, now fuck off kid"

"Asshole!" Vince yelled as he ran to his house. I felt like chasing after him, but I decided against it.

3 weeks had passed. I had given Jason a part-time job at the skate shop after one of my employees quit. He didn't leave on a bad note, he was simply leaving because he was starting college soon. Which I respected that decision. I didn't go to college, it wasn't my thing.

During those 3 weeks, Jason and I would have more sexual encounters. It was mostly the same thing, I would blow him and pleasure him with my finger or fingers, and he would shoot his yummy load into my mouth. It wasn't an everyday thing though, it was more like ever 3 or 4 days. It would usually happen on the weekends. Aside from the good sex, we had become very good friends. We would watch movies and shows together, played video games. It was an odd feeling, he felt like a younger brother but with sex.

One day though, Jason felt like trying something new. Something I would never have thought I would be doing with him.

I had just gotten out of the shower when I heard my doorbell ring. I was wearing black shorts with a gray tank top. I wasn't expecting any guest and it was raining hard outside. I walk to the door and open it, there stood Jason, dripping wet and out of breath.

"Can I come in?" he blurted out.

I moved out of the way and he came stumbling in.

"Are you okay?" I asked him.

He didn't say anything at first, "I got into an argument with my parents and ran out. I didn't know where else to go."

"It's alright," I said closing the door. He was soaking wet, I needed to throw those close in the dryer. "Let me put those clothes in the dryer, don't want you getting sick," I told him. He removed his wet jacket and sweats. When he took them off, he was wearing a gray t-shirt and black boxer briefs, both of which were also soaking wet. I gestured to him to remove everything. He removed the rest of his clothes, handed them to me and stood there naked. It hit me that this was the first time I really saw him completely naked. His slim toned body was appetizing, he had little hair on his body. He clearly had the body of a twink.

I threw him a towel so he could dry himself off as I put the wet clothes in the dryer. When I came back I saw the towel wrapped around his waist. He was sitting on the futon.

"You might want to take a shower," I told him.

"Yeah, you're right. I don't have extra clothes though."

I put my hand up, "we're both the same size. I'll lend you some."

"Alright, thanks, man."

Jason got up, walked to the restroom and opened the door, entering the bathroom. Before closing it, he turned to me with a smile and removed the towel. Giving me a brief shot of his bare ass before closing the door. He was teasing me and I loved every moment of it.

After a few minutes, he came out with the towel wrapped around his waist. I handed him the clean clothes I retrieved from my room earlier.

"Thanks," he said.

Instead of going back into the bathroom to change. He simply dropped the towel before me and began putting the clothes on. He slipped on my low-rise briefs with a gold waist band. He looked up at me, "They're snug. I like them."

"Thanks, I'll grab you a new pair next time I'm at the store."

He nodded and continued dressing. He threw the band t-shirt on and slipped on blue shorts I gave him. After he was dressed, I warmed up some food and we ate. I asked him what happened and he told me that his parents were upset over the fact that he didn't want to go to college. We continued talking a bit more before we made our way to the living room. I sat down on the futon first, then Jason followed suit. I couldn't resist looking at his young slim body. For some reason, I was aroused by him wearing my clothes. The t-shirt was loose on him but the shorts were snug on him. I would look down and see his bulge.

"Damn Jason, you look good in those clothes, " I said to him

Jason smiled, "thank, bro."

I moved closer to him, "I just want to take them off piece by piece and suck that dick of yours."

"I wouldn't stop if you did." he implied.

After doing this so many times, the guilt had faded away. I began to feel less and less guilty about doing it every time. He would come over and I would pleasure him and at the end of the day, we would remain good friends.

I ran to the room to grab the tube of lube. Jason had grown to love the fingering and oral combo. When I returned, Jason was standing before the futon. I moved passed him and closed the curtains behind the tv and then got on my knees. I could see his growing member under the shorts and began kissing it through them. My hands moved behind him and caressed his bubble butt. I used my teeth to pull down his shorts to his knees, revealing the baby blue briefs I lent him. He looked so good in them. I was definitely going to buy him more of these. His boner was pointing to the left, the underwear could barely hold it. I continued licking through the underwear until I pulled out his 6-inch dick.

I put my hands back on his ass and took his dick in my mouth. I bobbed my head passionately, so much that saliva was dripping down my jaw from so much sucking. Jason began to moan even more. After a few minutes, I put his balls in my mouth and sucked on them. While I was doing that I put lube on my index finger. When I was ready I went back to sucking his dick. My right index finger slipped into his rectum and I began pleasuring him from both sides. It was a two pronged attack of pleasure. This was my prefered method of getting a blowjob, I loved it when guys would do this to me. While all this was happening I was looking up at him, his facial reactions were golden. I loved giving him pleasure, and he loved giving me his yummy load. When I would hit the right spot he would place his hand on my head and tilt his head back. We continued this for a few more minutes. After picking up speed, I felt Jason jerk. He placed his hands on my head and moaned loudly. I felt his warm load shoot the back of my throat.

He slipped out of my mouth, out of breath. I looked up at him, making eye contact with him and then proceeded to swallow his load.

Looking down on me Jason asked with a curious look, "How can you enjoy that?"

I grabbed his erection and lightly squeezed out some cum on my finger, like squeezing out the last bit of toothpaste. I held it up to him. "Try it"

Jason hesitated, staring at my finger, "Come on Jason, just once." I insisted.

Jason caved and bent down. He slipped my finger into his mouth and licked the cum right off my finger. He tasted it and then spoke, "It's not as bad as I thought it would be. A bit sweet."

"Yeah, it tastes better with an entire load in there."

I stood up before him and grabbed a towel to clean off the excess lube. I turn to Jason and saw him standing there. Still in underwear with the shorts at his knees. He was looking down in my direction, I did the same and saw I still had an erection. Jason stared at me, then spoke. "It was a shit day until I came here. Thank you for making me feel better." He paused waiting for a reply. When I didn't say anything he continued. "I don't know why I want to do this, but can I suck your dick?"

I turned in a bit of a shock. Jason was straight and we had a good relationship. I would suck his dick and finger him and nothing more. I was already surprised that he tasted cum, but now he wanted to suck my dick? He was clearly being emotional after a rough day, but I was curious. I knew he wouldn't be good at sucking, but he could learn. I mean I was a noob once.

"Why though?" I asked.

Jason shrugged, "Honestly, I don't know exactly why. I feel bad sometimes like I'm taking advantage of you. I know you take joy in sucking my dick, but I feel I ain't giving you anything in return."

"You dick is enough for me dude. You don't have to do anything you don't want to do." I said placing my hands on his shoulders.

"I know but I am also curious about what it's like to suck a dick. I mean you only live once right?"

I laughed.

My dick was hard during the entire conversation, my dick wanted to say yes but I wanted to say no. But I thought about it, Jason and I have had several sexual events, it wouldn't hurt him to try something new. Like he said "You only live once"

"Alright," I said,

With confirmation, Jason removed his shorts entirely and got on his knees. His erection was gone by now. Looking down, I slid my shorts to the ground. I was wearing white low rise briefs, similar to Jason's.

He gazed at my erection hidden beneath my underwear. He didn't kiss or lick my dick through my underwear like I had done to him several times in the past. Instead, he pulled down my briefs just below my balls, enough for my uncut dick to spring out. I was a big guy, 7 inches long and was some nice girth. Wasn't really ideal for a noob but I wouldn't force it all in.

Jason paused for a moment to take a good look at my dick. "You start with the tip and work your way down. You can take it slow." I told him.

Jason grabbed my member with his hand and I felt his warm mouth around the head. He started slow, with each suck taking it deeper into his mouth. He gagged when it was halfway in.

"We can stop, " I said.

Jason coughed. He ignored me and took my dick back into his mouth. This time he was sucking a bit faster, still only making it halfway. As he sucked, I started to moan lightly, but to be honest, at this rate I wouldn't cum. So I decided to take over. "Let me take over," I told him.

I placed my hands on his head and began slowly thrusting my pelvis into his mouth. I started slowly for he could take it. I could see saliva dripping from his mouth and decided to go a little faster until I felt I was about to cum. I immediately stopped and pulled out.

"What happened," Jason asked clearing his mouth.

"I was about to cum."

Out of breath, Jason said. "Cum in my mouth."

"Are you sure"

Jason gulped, "Yeah, fuck it."

I slipped it back into his mouth, "Hold on to my ass." I told him. After he clamped my underwear covered ass, I began thrusting, I started slowly for a few seconds. Feeling his warm mouth around my member. When I felt like finishing I picked up the speed. A few moments later, I felt my legs buckled as my load shot into Jason's mouth. He grips tightened on my ass, while my grip did the same on his head. I let out a load moan as I shot everything I could into his mouth.

After I finished cumming in his mouth, I pulled out. My penis was still dripping with cum. He looked up at me with his mouth open with my pool of cum in his mouth. "Spit or swallow kid."

Jason gulped down my load, "Ugh, does it always go down like that?" he said.

"Yeah, you get used to it."

Jason got off the floor and stood before me, "That was actually fun. I'm not entirely sure if I will do that again." He looked down to his underwear, "But that got me really hard again."

I smiled, "I can take care of that."

As I was about to knee before him to suck him once more. Jason asked me a question, "Um, does anal hurt?"

I took the question simply as curiosity

I shrugged, "Yes and No, it's a bit more aggressive than finger banging. It will hurt at first when it's going in. But once it's in, it's pleasure town."

"I wanna try it."

"No," I blurted out. First, he wanted to suck my dick and now he wanted to get fucked? This kid's curiosity was booming today. To be honest, I had always thought about parting those cheeks and slipping my dick in. I had never brought it up to him because he was straight and I didn't want to mess up what he had going.

"Why not? You already finger bang me and it's amazing," he argued.

"I thought we agreed on just the blowjob and that's it." I protested.

"The blowjob and fingering are great, but after seeing your dick. I kinda want to try it."

I couldn't believe it. Without hesitation, I said yes.

I guided him to my room, where it was a bit more private. I removed my shorts completely. We were both in our underwear and shirt. I opened the top drawer next to my bed and pulled out a condom. I still had the tube of lube in my hand, I would be needing it. Jason stood next to the bed, his erection was gone now. Mine had begun to deflate from no sexual action, I was still semi hard of the thought of what was about to happen.

I stood before him, "Are you sure about this?" I asked him one last time. I wanted to make sure he was okay with his decision.

Jason thought about it one last time, "Yes, let's do this." and sat on the bed, "So what position is the best?"

I had thought of this scenario many times. Never thinking it would happen. "Honestly, on your knees."

"Alright," he said, "But let's get you hard again." He was right my dick had gone soft. He pulled out my dick once more and began sucking it. While he was getting me hard, I tore open the condom wrapper and let him suck me for a few more minutes. When I was fully erect, I slipped on the condom. He then got on the bed and kneeled down in the position I told him, the doggy position. I got on the bed and got behind him and grabbed the lube. I then pulled down his briefs to just below his asscheeks. I began lubing his asshole up, when that was done I then lubed my erection.

"Alright, take a deep breath. Also, tell me when you want to stop." I told him trying to assure him.

It had been a while since I fucked a virgin, but I would take it as slow as I can. I grabbed him by the hips and slowly moved my dick into his ass. He grunted when my tip began entering his tight ass, but I continued. "Ouch," Jason said in pain when my dick was halfway inside, "Continue," he said.

I continued and when I was fully inside, I began to thrust slowly. My penis brushing against his prostate. After a few good thrusts, I began to go a little faster. I could see Jason was beginning to enjoy it. So I went faster, my balls began slapping against his asscheeks. It felt so good fucking his tight hole, but I think I may have enjoyed it a bit too much. A few seconds later, I came, but I couldn't stop thrusting. I moaned as I shot my load, each thrust being one blast of ecstasy. When I finished cumming, I finished thrusting and pulled out slowly. Letting him feel every inch of my dick leaving his body. Jason fell to his side on the bed, then shifted to his back. I removed the condom and tossed it in the trash. I then lied beside him, we were both out of breath.

"How was it?" I asked him.

Jason caught his breath, "it was great."

We both laughed.