[Non-Fiction] Finding Our Friendship

[SAMaster]

Good posts, cannot wait to see what happens next.....

[Pineappled]

I only had to endure this torment for 5 minutes. I kept telling myself, “He couldn’t do anything too terrible, after all, I was stuck in this wedgie. Also Stan is my best friend, he wouldn’t do anything to hurt our friendship.” However, I was lying to myself, and I knew it.

For the first thirty seconds or so, Stan would grab, squeeze, and just play with my ass. Tapping on it, lifting and letting the cheeks drop. This wasn’t to bad.

Then he started to play with the underwear that was wedged up my back. Making it tighter, I winced in pain, but didn’t make a sound. I could tell Stan wasn’t looking at my face.

He then moved to my front. Without any hesitation or second thoughts he immediately cupped my balls through my underwear. The moment he touched me, a shiver ran up my spine. I started to swing slightly in my wedgie.

He looked at me in the eye, and I looked away. I didn’t want to see, or know what he was going to do with the remainder of his time.

I felt his hand let go of my balls, then I felt his hands prying at my underwear. I looked down to see him trying to manuver the flaps.After some squriming on both of our parts, his work paid off and he pulled my penis out. I wasn’t very hard, but Stan was going to change that. He slowly started to stroke my penis, up and down. Each movement sent a wave of pleasure directly to my brain. “Dude! What are you doing?” I asked, half frightened.

“I still got 2 minutes to do whatever I want.” He firmly grabbed my now erect dick, “I want to do this.”

He was no longer being gentle; he was squeezing my testicles through my underwear, it hurt alot, but at the same time it felt good. He was also pulling and squeezing on my erection. I felt like I was going to burst. The pain from the wedgie, my balls, and now him playing with my erection, it was all too much.

*DING DING DING*

The alarm went off. As soon as it did, he released my privates, and started to walk up stairs. He released the leash and my feet finally touched back to the ground. I put my boner back into my underwear, an obvious tent now in its stead.

“Well, that was fun!” He said. “Now, its time for your level 2.” As he completed his sentence his mouth formed his trademark grin, and he pulled out a sharpie.

I didn’t say a word. I just wanted to get this over with. Stan walked over to me and wrote in big letters on my stomach, “ASK ME TO DO ANYTHING” all in caps.

“Cmon, lets have some more fun!” He said as we walked into his room. I sat down at his computer chair. “Here are the rules.” He started to explain, “the dare you wrote says: you must do anything for 5 people until they leave. So that means that if they leave before they tell you to do anything, that doesn’t count. Also you can’t leave if someone asks you to do more than one thing, they have to leave first.”

“Dude, cmon we could be here forever!” I protested. “What if someone is daring me for hours straight? I don’t want to be here for hours. What if all 5 people do that?”

“Okay okay, I see your point.” Stan started to think. “Fine, how about you have to do anything that the people say, for five people, but for a maximum of 5 minutes, then we leave.”

I wasn’t happy about this, but it was better. “Fine.”

Stan nodded, “Good. Now take off your underwear and we will begin.”

[Pineappled]

Sitting naked in Stan’s chair, his webcam facing me, I was more scared of this than anything. I made sure that his webcam focused on my crotch, I know that sounds weird for me saying this, but if people are going to see me naked, I didn’t want them to see my face. Stan was okay with this.

“Just five people. I’m going to stand over here so they don’t see me.” Stan seemed nervous also, why I don’t know.

“Do I have to talk or can I type?” I asked.

“I’m gonna do the typing for you.”

I wasn’t sure how to feel about this.

“Alright, here we go.” Stan said as he logged on to chatroulette.

Within seconds the first person was connected. She was about 25 or so, the second she saw me she laughed, “Wow.” she quickly disconnected.

Immediately after the website started to connect me to another person. I didn’t get a good look at them, but they disconnect nearly immediately also.

The same thing happened two more times.

I realized what was happening. I reached for the mouse and logged off the website.

“What are you doing dude?” Stan asked me.

“Look, people are just going to keep disconnecting the second they see a penis. I hate to say this, but write ‘ask me to do anything’ bigger.”

Stan agreed with me and grabbed the sharpie. He bolded the anything, and we made the camera focus on that instead of my crotch. You could still clearly tell I was naked though, but it wasn’t the first thing you saw.

We tried the website again. First connection we get is with a group of girls, There were 3 of them, and they were no older than 15. They sat there giggling for a second and whispering to each other. I sat there motionless, too frightened to do anything. “We can ask you to do anything?” One of the girls asked.

Stan typed the response, “Yes.”

The girls were obviously delighted, and one of them went to the back of the room. I heard a door shut, I can only assume she didn’t want anyone walking in.

“Are you naked?” the girls asked.

Stan moved the camera to show my privates. The girls leaned in and were giggling. “How old are you?”

“14.” He told the truth, I was kind of hoping he wouldn’t.

“Wow, so thats what boys our age look like! So different from the videos.”

I was so embarrassed. Stan took advantage of that, “What do you mean different?”

The girl who I assumed was the oldest responded, “Well we’ve only seen naked men from porn. You look a lot smaller than that, but you’re real!”

Stan was trying his best not to crack up. “Oh, yeah I guess it isn’t that big. So, what do you want me to do?”

I was bracing for the worst. The girls were talking amongst themselves for a few seconds. “Show us your butt!”

Stan looked at me as if to say, “you heard them.”

I stood up from the chair and turned around. The girls whistled.

“Bend over!!!” They nearly yelled.

I did as I was commanded.

The girls went silent, a moments later one of them timidly said, “Spread your cheeks.”

Reluctantly I did. There was nothing but silence for the next few seconds. I peaked my head around to see what was going on, the girls were taking photos of their monitor. I didn’t say anything, but I felt like I was going to die. I looked over at Stan and he flashed 3 fingers at me. Great, 3 more minutes.

“Hey, turn around now.” they demanded.

I did, and there was an audible gasp. My penis was now fully erect. “Oh, wow. That is different! You like us?” A girl asked.

Stan typed my response. “Yeah, but I only got 3 more minutes. What do you want?”

A short pause,“Show us your face.”

I looked to Stan, and he nodded and aimed the camera at my face.

“Oh wow, you’re actually kind of cute.”

That made me blush. The girls called me out on it.

“Jack off.” That was all a girl said, I didn’t catch who said it, but all the girls were now smiling and staring at the screen.

I sat down at the chair, Stan moved the camera to show my face and my crotch in the same shot.

I started to masturbate slowly, hoping to run out the timer before I would cum.

“Go faster!” One of the girls said.

I started to pump a little faster. I had never had this strong of an erection. I was enjoying this almost too much.

A few seconds later I heard a knock, and then the girls disconnected. I assume their parents came in and they didn’t want to be caught. The thrill of showing myself to girls my age was immense, I could feel my heartbeat in my chest.

Stan noticed the girls disconnect and said, “Ah what a shame, they liked you! Oh well, time for the next one.” He repositioned the camera to just show the dare, “ASK ME TO DO ANYTHING”

[wedgielover3]

This is really good! Please keep going.

[Pineappled]

My heart was racing. After what just happened being both humiliated and complimented, it was a new experience to say the least. The next person connected. It was a black screen. Nothing happened for a few seconds, then a message popped up. “Anything huh?”

Stan typed my response. “Yeah.”

There was silence, neither of us had any idea what was going on. Then we heard the clicking of a keyboard. “Why?”

I was confused. But at the same time glad. I looked over to Stan, he shrugged and started replying. “I lost a bet. Have to let people on chatroulette dare me to do whatever.”

“lol how old are you?”

“14.”

To my relief he disconnected.

“That counts!” I said. “Only 3 more to go.”

Stan wasn’t happy. “Whatever.”

The next person connected. It was a dude in his room. He looked alone, and in his mid to late teens. “What do you mean?”

Stan was annoyed at always answering this. He later told me, “What’s so hard to understand about ‘ASK ME TO DO ANYTHING’?”

He typed the same response as the last time. “Lost a bet, you have five minutes to tell me to do anything.”

The duded started cracking up. “Anything? Are you naked?” He asked.

Stan shifted the camera to show my flaccid penis.

The guy reacted instinctually and looked away. “Thats fucking gross. Put some pants on.”

This is actually working out for me. Stan was obviously fuming. I came back a moment later wearing my pants.

I went on to have a conversation with the dude for the rest of the 5 minutes. It was all about how I lost the bet, what I had done so far; basic stuff like that.

Stan told me time is up. He clicked the button to disconnect and find a new person. “Take off your pants.” He instructed.

Two more people. I can do this.

For the next few people it was the same “What do you mean anything?” Then showing them my nakedness and then them promptly disconnecting.

The next person went pretty much the same as the guy who told me to put pants on. I enjoyed these conversations but it made me think, these guys are just lonely, and wanted to have a conversation. It was somewhat of a downer, but made me feel good because atleast I didn’t have to do anything embarrassing.

For the last person, it was another group of people. It was a girl and a guy. Both of whom seemed to be in their early twenties. They asked me how old I was. Stan responded. Then they told me to show them my penis. Stan was delighted. The guy started to whisper in his girls ear. And she responded, “Yeah, but you’re not 14.”

They disconnected shortly after.

“That’s 5!” I said to Stan.

“Yeah, but you still got the level 3’s. You ready, because we are doing mine first!”

He just had to go and ruin my good mood.

[Nick]

Can't wait to see the level 3 dares!

[Dffd]

very nice ill be waiting for more

[Pineappled]

The next thing that happens, is not anything I was expecting when we first started to play truth or dare. Stan was getting stuff ready for my dare, he was grabbing a whole assortment of objects. “Don’t worry,” he said, “I’m not using all of these, but I gotta keep you guessing.”

“How long is this gonna be?” I asked timidly, nearly scared out of my mind.

“Only 2 minutes. But its gonna be a fun two minutes.”

I sat there in a chair watching as he gathered different things. On his bed he assembled a banana, peanut butter, cooking oil, a pen, an egg, a toilet plunger, water, a blindfold, the list goes on.


There was no way he was going to use all of these. And there is absolutely no way any of that was going to fit. And if it would, I couldn’t imagine the pain.

“Alright man, I’m gonna be nice. Here.” He holds out a blindfold for me. “This way you don’t have to see whats happening.”

I reluctantly grabbed and put on the blindfold. Maybe it would be better.

“Stand up.”

I did as I was told.

He put one hand on my back. It caught me by surprise. He told me to let him lead me. I walked a few feet over, I realized I was now standing on a towel he laid out. “Sit on your knees.” I complied. Next thing I felt was a hand on my back, “Bend over and stick your butt up.”

I could hear the anticipation in his voice. And that anticipation turned into pure fear for me.

I sat there, in a doggie style, waiting.

I heard Stan leave the room right after saying, “I forgot one thing, give me a second.”

A few moments later he came back. “Alright, I’m gonna start the two minutes. You ready?”

I nodded weakly.

As soon as he had my confirmation I felt something press against my butt cheeks. It felt slimy, and soft.

“You’re going to have to loosen up, relax, it won’t hurt as much.” He said to me.

I tried my best, as I did I felt something smush into my rectum. I could only imagine it was the banana lubed with the cooking oil. It felt weird, soft but hard at the same time. Its thickness still being retained even though it clearly fell apart.

After what seemed like the entire two minutes he pulled that out. At that moment, I felt my hole. I had never really felt it the way I did now, it wasn’t a good feeling, but it wasn’t entirely bad either.

Just then I felt something press hard into my butt. I could clearly identify it was Stans finger, he must have had some cooking oil on it, but it was definitely his finger. He was fingering me, and I didn’t know how to feel. I felt both invaded, but at the same time I could feel him press on my prostate, and I had no idea that it felt that way.

What must have been a moment, seemed like a day. When he finally pulled that finger out, I could tell I had a full hard on. I was so embarrassed, I was hoping that he couldn’t see it because he was behind me. But those hopes didn’t really matter.

After I thought he was rummaging for more I felt his hands grab my sides, I had no idea what to expect next. Just then I feel something very hard penetrate me. I felt as if a rod was being placed into my ass. It hurt, and I let out a little cry.

“45 seconds left.” Stan muttered. I could barely take it anymore. I felt the rod go in and out of me, Stans hands on my sides. It was disgusting. My entire body was being hit with wave after wave every time Stan pressed it into me, each time going farther and farther. I felt as if I was bleeding, or that he was ripping me. Thank god for the oil, or this might have literally torn me.

It seemed to go on for days, but eventually I heard Stan’s phone go off. His hands left me and the rod pulled out. I collapsed on my side, my kness and my butt killing me. I sat there for a moment, Stan then said, “alright man, one dare left.”

I took off my blindfold and looked around the room. I saw on the towel a small pool of the cooking oil, I immedately felt my ass and my hand was drenched in it. Stan really used a lot. Next to it I saw the banana along with a plunger.

I attributed the plunger to being that rod, which wasn’t as bad as I thought it would be, but then I turned around. Stan was completely naked, he had a full erection, and was still wearing a condom.

[Officelover]

This is actually an excellent story. I normally do not enjoy Truth or Dare stories, but this one is well written and somehow compelling. You say it is true?

[Pineappled]

Yeah, the entire thing happened. Of course I condensed it for my own sake, but I'm (obviously) keeping the good stuff in. My take on it is, it's in the past, literally nothing I can do about it. People want to read about it? Then sure I'll post it. I've read what I think are worse stories on here, and according to you guys, my story is pretty good. Plus writing gives real perspective on things.

Also, the feedback has kept me posting.

[slaveandslaveonly]

Please continue, I am dying to know the next part!!!

[kojiko]

Its amazing! Thank you for sharing, but seriously...cant wait.

[Pineappled]

With the longest single two minutes of my life over, I had felt time speed back up to reality. I had blocked out nearly all the information of what had just happened. Not addressing my nearly torn asshole. Nor the condom on Stan’s erection. Everything had happened, and there was nothing that I could do about it.

I was sitting there, as I imagined my brain a computer, dumping all the memory of the past few minutes.

“Ready?”

I had just become aware that Stan had been talking to me.

“Sorry, what?” I asked.

“Your last dare. You’re my slave now.”

God dammit.

“C’mon, lets get started. I have the entire time planned out!”

He threw me the dog leash that was used in my wedgie a while ago. Along with it he handed me a collar. It was at this moment that something had registered. Stan didn’t have a dog. He never did, that means he went out and bought these especially for me. The thought made me cringe.

I put the collar around my neck, once the clasp was on Stan connected it to the leash. “Alright slave, time starts now.” He showed me the alarm on his phone, it was set for 2 hours from now. “First things first.” His grin growing. “I have something on that is irritating me. Please take it off.”

Stan was naked, it took me a second to realize what he meant. I didn’t believe him to be serious, but the look in his eyes, and the growth of his member proved otherwise.

I reached out for it when I felt a yank on the leash. “With your mouth, slave.”

“Dude, seriously?!” This was starting to get out of hand.

“What? It’s not the worst thing. Okay, fine you can use your hands. But there’s gonna be a punishment for this.”

I reached out for the condom again and took it off.

“Good, now get on all fours.”

I did as he said. He walked behind me.

“Spread your legs.”

I complied, I was prepared for the worst.

Much to my surprise he just sat on my back, straddling me backwards. “Comfortable?” He asked.

No. “Yeah, I guess.”

“Good, don’t move, and don’t you dare make a sound.” I could hear his grin, and feel his erection tensing.

Just then I felt his weight shift, I feel one hand on my balls and one on my ass. I was fighting every urge not to say anything.

His hand left my ass cheek and I could feel one finger delicately move towards the center.

I was thinking to myself, “There was no way he was going to...”

But as his finger slid across my ass, I tensed up. There was nothing delicate about what he was going to do.

[Pineappled]

As Stan was using his finger to invade me, my entire body was going through a myriad of senses. The fact that I was on my hands and knees having to support Stan, and myself while he was doing this was no small feat. While Stan's finger was smaller than the other things he had used earlier, he was moving this around much more, my body had never experienced anything like this before. And lastly, he was squeezing and rubbing my balls at the same time. I was doing my best not to moan or cry.

Luckily Stan’s fun had come to an end, and without word or warning he stood up and released me.

“Stay like that.”

I stayed where I was. Stan stood behind me, I felt like I was having flash backs. “Not again.” I kept thinking to myself.

What happened next wasn’t something I was expecting. Stan sat down behind me. I bent my head down trying to see what he was going to. I could see Stan was sitting on his knees, at the perfect angle for something that I was having flashbacks to. Then I saw a hand reach out and grab ahold of my erect dick.

“I could see you enjoyed that. Not too often you get this huh?” He asked, clearly enjoying himself.

He started to slowly jack me off. “Well?” He asked. “Answer me slave.”

I didn’t want to disagree with him. “Yes.” I managed to get out.

“Oh, good! Well if you enjoyed it.” He proceeded to insert his finger back into my rectum. As he entered a moan was forced out of me.

I was not used to this. Being both Jacked off and penetrated, it didn’t feel great, but it certainly wasn’t bad. Not long after I started to feel that urge. “Stan I-”

“Master!” He pushed in deeper.

“Master I am going to cum!”

His pace quickened. And with it I had one of the strongest orgasms to date.

Stan stopped, “Stand up.”

I did. “See this mess. Clean it up, I’ll be back in a moment.”

I started to clean up the cum off the floor. It wasn’t an easy task because he had carpet, I used toilet paper and some 409 to get as much of it as possible.

Stan came back and remarked, “Oh, it looks like you got all of it.”

Thank god.

He pulled out his phone. “Looks like I still got an hour and 40 minutes left.”

I couldn’t believe what I was hearing. That entire event was only 20 minutes?! What had I gotten myself into??

Stan was still on his phone. “Slave grab my clothes. I need you to dress me.”

I was honestly confused. Why? What is he planning?

I grabbed his clothes off the floor and started to dress him. The entire process was humiliating.

When I was putting his shirt on him I heard his phone vibrate. He was texting someone. What about? Was he sending them photos? OH GOD, is that why he blindfolded me? I had to ask, “Master, who are you texting?”

He smiled. “Oh, a mutual friend.”

I dared to press further. “You didn’t send them a photo or video of me, did you?”

His smile faded. “No. Don’t worry.” He proceeded to text again.

He grabbed a hold of the leash and we proceeded to leave his room. “What about my clothes?”

He yanked the leash a little. “You have to be naked for the 2 hours, remember?”

I had no idea why I wrote the dare the way I did. There's no way that I would have made Stan do things this bad.

We proceeded to sit on his couch downstairs watching TV. This caused me to be nervous. Why? Why just watch TV? 10 minutes later I had my answer.

“Get the door, slave.”

[Dffd]

cliff hangers.... >: (
thats all im going to say