Hope's Life Pt. 01

I looked around the room. My toys were neatly stashed under my bed. Everything looked fine. Ellie knew what she was doing. I looked my phone. It was 2:16 PM. I called Ellie a few times but she didn't answer. She is ignoring me. Looks like I have no choice but to go. I stepped into my bathroom and took a quick shower. I shaved my whole body, a habit I picked up soon after I recorded my first video. I gave myself an enema and cleaned my insides. I was thinking, what the heck, I have time. A little buttfucking won't hurt.

I exited the bathroom and took my favorite dildo. It's a 24 cm long black veiny shaft with big swollen balls. I call it the Mandingo. I lubed my asshole and attached the dildo on the wall. I lined myself with it, crawling on all fours, taking it from behind like a bitch in heat. The head plopped inside and I smiled with glee. I was still very loose so the rest went in smoothly. I began rocking myself back and forth in it. It took me, maybe, ten minutes before my dick started dripping cum. I did not have enough though. I still had time but I was craving more. I slipped the Mandingo out and grabbed another dildo from my collection. This one was shorter but thicker. I call it the chubby guy. I attached this one on the floor and took the Mandingo and put it right next to it and attempted to stuff both of them in my ass. Now, keep in mind, this was my first try of double penetration. I had no idea how it would go, nor how much I had to stretch myself. I hovered myself over the dildos and the big boy went in without resistance. I was still very loose. While going down the fat one came into contact with my ass and I guided it towards my hole. To this day I still don't remember what came over me but stretching myself with these dildos was the right call. Sure made things easier later. Anyway after a few failed attempts I figured they won't both fit. I felt like quitting and as I was getting up, my feet slipped on the dripping lube and, I kid you not, I sat on the dildos with my full weight. The chubby guy went in and stretched my ass so violently it made tears come down my face. Now this was a situation I did not foresee. I was hoping it would go smoother with less pain. The pain and the shock combined and I sat there unable to move for like half an hour straight. I'm not joking here. There were two dildos in my ass, 24 cm inside and stretching my hole about 10 cm both. In that moment my only thoughts were "This was so avoidable. What was I thinking? I am never doing this again. My poor asshole, it hurts so much." Even though the pain faded, I didn't play like I intended to and got up as soon as I felt I can stand again. I rushed to the mirror to get a better look at the damage. Yes, my ass had a small crack and it was bleeding. Nothing serious, but I disinfected it and slapped a bandage on it.

"Good God. This was the worst thing that happened to me so far." I thought to myself. So far is correct, if I knew what was coming, I'd be fearing for my life.

Now I was ready to leave. It was about time too. Only an hour left. Out of pure habit I plugged my ass with a medium sized rubber buttplug and started dressing up for the "double date". I figured I don't need anything official but nothing too casual either. I put on a plain black t-shirt and short jeans over my boxers. Normally I am used by now to put panties or a thong but I didn't want to accidently show anything and be made fun of. I grabbed my phone, keys and wallet, strapped my sandals and rushed out.

First thing I did was sneak next to Ellie's house and peek inside. I was kinda interested what she would be wearing. Since there was no movement or really any noise coming from inside I figured she wasn't there. I left and headed out for Tony's pizza. It wasn't far but still half an hour walk. When I was closing in I saw Donnie. You remember Donnie, the bully from high school. He was just standing in front of the pizza place. No way am I going there now. I stopped near a store close to the pizza place. Who knows what might happen and I don't wanna start a fight. Then I saw from the opposite side Ellie and Candy walking together. If Donnie gives me any trouble I guess I have to defend myself. I mean, I don't want to look weak in front of the girls. Not that it matters, they've seen me how weak I actually am. They reached the pizza place and Candy introduced herself to Donnie. I was watching and I did not believe my eyes. I had some theories and I was hoping, against hope, that he is not, I repeat, not Candy's date. Ellie saw me and waved at me. I guess I have to go now. As I got closer, Donnie turned around to look at me and just said:

"Son of a bitch."

Yeah, that's what I would have said in this situation too. Candy pointed at us:

"Do you two know each other?"

Naturally I answered:

"Yeah, we know each other."

Donnie was silent now. Guess he didn't want to look rude to his date.

"Aww you're friends? Just like me and Ellie."

"No, no. We just know each other. No friends." I quickly corrected her.

Donnie just shook his head. Candy motioned to enter the pizza place and we slowly entered. It was empty. Aside from Tony who was working there, nobody else was in. I won't bore you with the awkward conversations we had so to sum it up, we ate pizzas, we talked about what we do, what we liked to do and that's about it. I didn't have any expectations from this double date and I am proud to say that it didn't go as bad as I imagined. Until...

"You guys wanna come to my place for some drinks?" Candy broke the awkwardness.

Almost immediately Donnie nearly shouted:

"YES!"

Poor fool. He doesn't know what he's getting into. I myself was hesitant as I had bad experiences with Candy in the past, but Ellie looked at me and discretely grabbed and dangled the little key on her necklace. Almost immediately I figured that, that was the key to the chastity cage I was wearing. I felt trapped, I felt like it was a set-up. I was left without a choice.

"Sounds good, let's go!" What else could I have said?

Half an hour later at her place we were already drinking. The "girls" were getting hotter and looser. I and Donnie were getting hotter as well, but we were not showing it. Ellie and Candy began touching each other and lightly kissing. I was getting hard and I could tell Donnie was too. They looked at us and asked if we wanted them to do some more kissing. Donnie was so into it. So they did, it was a full blown make out session of what you might think two bisexual girls would do. After like three minutes of passionate kissing, Ellie turned and pointed at us.

"Now, you two."

"Alright!" Donnie exclaimed and stood up.

Candy pushed him back down.

"No, you two kiss each other."

They were giggling and I don't know if Donnie knew but I definitely knew they weren't joking.

"Uhm, what?"

"If you two kiss, we'll play with our tits for you."

Donnie looked at me. I gave him "the look". You know the one, "no way in hell, never gonna happen" one.

"Hey man, just one kiss. It won't hurt you."

This is the part most men brake down and the party is over for them. But we were drunk, maybe if we kept drinking, we wouldn't remember it tomorrow. But with Donnie? Him of all people. I never would have imagined it. I gathered my courage and stood up.

"Screw it, let's just do it!"

He stood up next to me. We are about the same height, he came close to me and our lips touched. I thought that's as far as he would go but he actually started kissing me. It was like he was into it. Me? Not so much. I wasn't resisting but I wasn't contributing as much as him either. I was a participant, he was the MVP. The girls were licking their lips while watching us.

"Hot stuff, boys! Have you done this before?"

Donnie stopped and pulled back. He looked at Candy expecting his prize. The girls look at each other and took off their tops and bras. This was my first time seeing Ellie's tits. They were small B cups but they sure looked good on her.

Ellie grabbed Candy's massive tits and started sucking on her nipples. Ok, I have to agree this is pretty hot. In turn Candy pinched Ellie's nipples and pulled on them. Donnie was getting excited.

"You boys wanna get to the next level?"

"Hell yes!" Donnie exclaimed.

I was already having none of that. I was pretty sure where this is going. I've seen American Pie 2.

"Ok, guys, we will start playing with our pussies, if..."

Ah, yes, the pussy proposal. It might work on the average virgin but I am above that. Next came what I believe to be the most absurd thing I've ever heard. I didn't know it at first but it was getting increasingly obvious that this was planned for tonight.

"...you do something for us."

"We'll do it, just name it!"

I turned to Donnie and he was already sweating with excitement. The girls shared a look and said in unison while giggling:

"We want you to try playing with our toys!"

Donnie was all aboard the hype train and I think he believed that we'll play with some masturbators or some other shit but I was skeptical. Candy walked towards us and grabbed the cover of something that was sitting on the floor behind us. When she uncovered it, I don't know, it didn't seem like anything at first glance. I looked at it then looked back at them.

"If you manage to last longer than the other, we will do a threesome with the winner. How's that?"

That was a pretty good prize, if you think you are fighting for a threesome with two girls. Knowing that, I was probably going to let Donnie win just to see the look on his face when he realize exactly what he's won. But on the other hand, I kinda wanted to win that for myself. Getting sandwiched between two shemales was something I was actively excited about. But then it got me thinking. If I win and they keep Donnie to look at us while they fuck me... man, I'll never hear the end of it. Besides that, I didn't really want to compete against him. I was thinking, how about I just say no and get Ellie to give me the key on her neck so I can go home. I looked at her. She was dangling the key and it looked like she was saying "Do it! Or else!". Can I wrestle the key from her and run away? What if that is not the real key? I go home and try to unlock it but it doesn't work. Next thing I know she texts me to never call her again and I will permanently be stuck with a chastity cage for the rest of my life. Clearly I was trapped and had to play to their every whim until I got out. And still getting blackmailed and told what to do was kinda turning me on. What a mess am I, right?

"Alright, ladies, you got yourself a deal. Let's do this Donnie!"

Now he was looking unsure. And with good reason too. The contraption, if we can call it that, was pretty simple. A large metal board laying on the floor, two pillories standing on both ends of it and one smaller contraption in between them with smaller pillories on the bottom. Besides being trapped in it, I couldn't imagine what was in store for us.

"How do we do this?" Donnie asked and scratched his head.

Candy showed us how it works by pointing at every single element.

"First, we will strap you on each pillory back to back. Then we will secure your feet so you don't move as much. Then the fun begins. We will sit in front of you and try to make you give up by tickling and humiliating you. If you say that you can't take anymore, we will release and go have fun with the winner. The loser will have to stay on the pillory and listen to the sex we have until we are done. Sounds fun, right?"

I have to say, I was expecting a lot worse. But this did not sound bad at all. I kneeled in front of the pillory and waited for Donnie to join in. He assumed his place on the other side. Ellie unlocked my pillory and I put my hands and neck on it. She closed and locked it over me. I heard Candy do the same to Donnie. Next they positioned our feet in the lower pillories and locked them under us. So far, so good. Then they went into Candy's bedroom and took out a big chest. They opened it and took out some toys. First thing I saw was feathers. Piece of cake, right? But I underestimated them, I had no idea how ticklish I was. Lucky for me, so was Donnie. It was torture. For the next 5 minutes they had their way with us, tickling our most sensitive parts. But we endured. The girls decided to step it up a notch. They took out some whips and crops and my eyes widened. They pulled down our pants and exposed our bare asses.

"If tickling doesn't work, let's see if pain does."

I imagined the worst but it actually started pretty mellow. Light smacks on the cheeks and thighs, nothing too hard. It felt nice and exciting. Combined with the talking dirty and calling us all sorts of names, I assumed it would be pretty nice to go all night like this. I would soon regret this however when Candy pulled a monstrous double ended dildo and showed it to us individually. Donnie was starting to panic.

"Since we can't make you submit, we think it's best to leave your fate in your asses. Let's see if you can handle it."

Neither I, nor Donnie was making a sound. We don't want to look weak. Ellie showed up with a bottle of lube and started lubing our asses and the dildo. To put it into perspective, the dildo was 5 cm thick and maybe, maybe, at least 40 cm long. I liked the color scheme though. It was rainbow colored, I should order one for myself when we're done here.

"Ok, this is the last one. If we can't get you to give up in like, let's say 30 minutes, we'll just make you play rock-paper-scissors for it. Good luck I guess." Candy was getting bored.

I knew I could take my share of the dildo, but I didn't want to sound like I was enjoying it so I made some noises while they were inserting it.

"Ouch, easy, don't stuff the whole thing in!" I was really enjoying it though.

Donnie was copying every word I said. When the whole length was in, I heard Candy playing with it behind us.

"There, now it's not going anywhere. If you want you can push it out in your opponent's asshole. I don't know, just to make them uncomfortable and speed things up."

"Candy, sweety, I have some bad news. We ran out of drinks."

"Oh, no. Don't worry I'll go down to the store to buy some."

Candy left but a few minutes later came back.

"Ellie, can you come with me? It's dark and scary outside. I don't wanna go alone."

"Sure thing, babe. We'll leave you alone for a bit, boys. Don't go anywhere. Be right back."

Oh, but they were not right back. They were not right back at all. We spent the whole night trapped in the pillories with a monster dildo in our asses. Personally I didn't hate that part, I hated the pillory, it was not comfortable. The whole night Donnie was trying to push it into my ass and I didn't resist much. The whole night I think I had like 3/4th of the dildo inside me. Donnie didn't talk much which made the night more bearable. The girls did eventually come back in the morning. Well, they were brought back. Two large black men were dragging them while they were laughing and barely standing. They were so drunk they completely forgot about us. When they came in the apartment, one of the men laughed at us, commenting that we had quite the party here. They unloaded the drunken bitches in Candy's bedroom, took some pictures of us and left.

It took another 8 to 12 hours for them to wake up and come to us. First was Ellie who showed up at the door frame. When she saw us she gasped and covered her mouth.

"Oh... my... gosh..."

Now, I don't know about Donnie but I was preparing my "I am so pissed, I can't even look at you" face all night. Ellie was looking so sorry and apologetic but it didn't work on me.

"Oh my god, guys, I'm so sorry. We went to the store last night and we ran into these guys and they took us to this night club and we totally forgot about you. Oh my god, we're so sorry."

I cut her off.

"Save it! Just get me out. My neck and knees are killing me. Oh, and my ass too."

She came to me and unlocked everything, then unlocked Donnie. Candy showed up later, still a little sleepy. She came to us inspecting the situation.

"So who won? Who got the most dildo in their ass?"

She didn't look all that sorry. Ellie was having a hard time with the dildo. Apparently the lube had dried up and currently acted as glue. They couldn't get the dildo out. Ellie got more lube and poured it on the dildo and on our asses. At that time our cheeks were almost touching. Donnie was the first to poop out his part of the dildo. From what I could tell, he only had 6-7 cm worth of dildo in his ass at the moment before taking it out. When Candy saw that, she smiled.

"Well, the winner is clear. Hope, you get to have a threesome with us, congratulations."

My ass and my back were sore. I couldn't care less about the fucking threesome. Donnie was looking in disbelief at how much dildo I had in my ass. He didn't say anything. Ellie was slowly pulling it out of me.

"What a champ. I'm sorry we left you like this but, hey, it happens. Blame alcohol, not us."

Donnie pulled up his pants and Candy escorted him to the front door and pushed him out.

"So this was fun, we should do it again some other time." And she slammed the door in his face.

"Are you ok, Hope?" Ellie was concerned about me so much. "Let's get you cleaned up."

I didn't resist and let them drag me to the bathroom. My legs were numb and I couldn't walk on my own. They took off my clothes and gently placed me in the bathtub. Candy motioned to the cage I was wearing and Ellie took the key off her necklace and unlocked my cock. For the first time in two days I felt free. Then they began filling the bathtub with warm water and I drifted away. When I woke up later, I was lying in a bed. On my right side was Ellie sleeping. On my left side was Candy, also sleeping. I was feeling fresh and relaxed and attempted to get up. Apparently they were not sleeping because they each put one hand on my chest and kept me down.

"So... are we gonna talk about yesterday or what?" I finally spoke.

"Let's not." Candy said. "Instead we can have fun just the three of us all day. We'll do whatever you want. Think of it as an apology."

"Whatever I want, huh?"

"Whatever you want. No matter how crazy it seems. We'll do it."

Ellie and Candy were staring at me from both sides. I had so much power in my hands right now.

"Well, how about you play with your pussies like you promised?"

They both flipped the sheets and uncovered that we were all naked.

"You already know we don't have pussies." said Candy.

"Can you be more specific?" asked Ellie.

The ball was in my hands once again. I knew exactly what I want.

"Get the dildo you forced upon me and Donnie and fuck each other the same way we fucked ourselves!"

The girls shared a look and giggled.

"Is that it?" Candy asked.

"No, but let's start from here."

Ellie got up and took the dildo that was conveniently lying on the floor next to her. Candy crawled on all fours and faced her ass towards Ellie who in turn faced her ass towards Candy. It was all coming together.

"Let me hold that for you!" I took the dildo and held it between their asses.

"What a gentleman!" Candy smiled at me.

I pushed each end in each asshole and the dildo began to disappear. It took, maybe 10 seconds for the whole thing be absorbed by the ass sisters. Candy and Ellie looked at me as if waiting for orders. I had an idea. I grabbed their asses and split them up, revealing the dildo. I took it out and instructed them to face each other.

"Let's find out how your pussies taste!"

They immediately understood me and proceeded to deepthroat each end. Their throats began to swell by the intrusion of the thick dildo. Soon the dildo disappeared once again and they were locked in a passionate kiss. I was mesmerized. They didn't show any signs if they were choking or had any breathing problems whatsoever. Now I was concerned. They are doing this for me. What if something happens because of me? Were they feeling that guilty? Great, now I am feeling guilty.