Hope's Life Pt. 05

I slowly jumped out of bed and as I was standing my cock was just dangling there. I raised an eyebrow. This is not bad, I thought to myself. Kat passed me my washed clothes. I put them on quickly, then proceeded with taking my keys, phone and wallet.

"I think... I'll go for a walk. I'll stop by for a burger or two. Wanna come with?"

Kat just waved her hand.

"You go! I have work to do."

I went downstairs to check on my moms and by that I mean I wanted to avoid them for now. They were not home. Lucky me. Hungry as I was, I did not really feel like this is what I wanted right now. Right now I wanted to get wasted. So I went to the local bar.

Don't judge me! You have no idea what I've been through. To summarize... My moms are both my biological parents, I have an older sister who I didn't know existed, I impregnated and asked to marry said sister, I was the center of a gangbang with incest tags... And all I got out of it was this lousy massive dick.

Ok, I may be bragging about that last part, but hear me out. I did not have the luxury of having a penis I could be proud of before. I do now and I'm not gonna waste the opportunity to abuse it. Now that I think about it, I had some classmates who I was interested before. If I can track them down I might score some. Or you know, get called a freak and arrested. Can score in jail that way, but nah...

Probably gonna be put with some dudes and I don't swing that way. Big dick could in theory intimidate them into respecting me. I could become... Wait, no, what the fuck am I even thinking about? It's exactly this amount of overthinking that got me in the mess I am now. Although to be fair, this would have happened one way or the other. As I was overthinking again I didn't realize that I reached and even passed the bar.

I looked around just to check if nobody was looking and turned around walking to the bar. Getting lost in my thoughts was probably the reason why I couldn't remember how I got to the places I was going. Autopilot I guess. I walked in the bar, been here a few times, so the bartender knows me. I nodded to the guy and he nodded back.

"What will it be?"

"Let's start with... a light beer. And a sandwich, lots of mayo, hold the onions."

I sat down and with my peripheral saw a familiar face.

"Good lord, if it isn't the hairiest of ballsacks!"

The guy in question took a long puff of his cigarette and without turning towards me just exhaled.

"Wasn't funny in first grade, Hope. It's not funny now."

I moved closer to him.

"Oh, come on! Don't be like that! With a name like yours everything is a joke. Your dad knew exactly what he was doing."

He took another puff and a sip of his drink.

"I'm not in the mood for jokes, man."

"Alright, alright! By the way, I remember you said something along the lines of "I'm gonna quit smoking and drinking and get myself a girlfriend." So what gives?"

He took another sip.

"My mom died last week."

Way to bring the mood down, asshole. It was a bit weird.

"I see. Sorry, man. It's... uhm... you hated her though. After all she did to you..."

"She's still my mom. Fucking bitch! But, she's been battling that cancer for a while."

"Well, no wonder you fell off the wagon."

He took another puff.

"I'm smoking for her alright. I'm drinking cause my dad is remarrying. Thing happened in a flash, like... He knew that woman while mom was still alive."

"Well... at least you gonna have a hot step mom. She is hot, right?"

"Gorgeous! And a cute daughter as well."

"Nice! You gonna live the dream. I think. Like those, uhh, remember those old step mom pornos we saw at Smilka's. That was so hot."

He finally looked at me.

"Hope..."

"Wassup, Harry? You thinking about it?"

"Just so there is no confusion her name is Anita. Anita, Hope! She will take our family name. Dad insisted."

"Ok, so what's the prob... Oh, God, I just..."

"Yeah, the cogs are turning now, eh? Anita Bolzac. I sure am glad I finished school."

"And her daughter?"

"Candice. Think she will get bullied?"

"Oh, fuck. Well, you know, kids are assholes. Just look at us, we're prime examples. Sorry for calling you hairy ballsack all this time."

"It's alright, bro. I know you don't mean any harm. Like you said, we are assholes. By the way, did you hear? Andy is walking again."

"Who the fuck is Andy?"

"Oh, you know Andy. The one from our class who was in a wheelchair his whole life."

"Can't seem to remember..."

"The German boy with the weird haircut."

"I still..."

"Goddamn you, Hope! You ARE going to hell. The one you kept calling Andolf Crippler..."

"Ah, yes, the Crippler! How could I forget!"

"You can't call him that anymore. He is walking and he got married."

"So, he managed to take a few steps just to get on one knee! Wait, I thought his condition wasn't curable."

"Well, I don't have all the details, but what I understood was that some guy contacted him and told him there is a new medicine that might help. And I guess it worked and he fell in love with him and then they got married."

"The Crippler was gay?"

"I don't think so. I do remember times when we snuck porno mags in school and he genuinely enjoyed them."

"Well, you wouldn't believe who IS gay. My best... wait... the... what was it... uhm... yes, tomato."

"Huh?"

"Tomato, man, tomato. Andy is a tomato."

Harry looked confused as fuck and generally didn't know what to say.

"I don't follow. Why is he a tomato?"

"You know how tomato used to be a vegetable and they changed it and now it's a fruit. Same thing with Andy. He was a vegetable, now he's a fruit."

Harry got up and attempted to leave.

"Your silence speaks volumes, bro. But it was funny, right?"

Before he reached the door he turned around and pointed at me.

"You are too early with the dad jokes. Wait until your kid is born. Which will be soon I was told. Sisterfucker... heh heh..."

I got chills down my spine and turned towards him. He was exiting the building. I jumped from my chair and followed him.

"Yo, boss, cancel my order! I have to go."

"Fuck you, Hope! Your order will be waiting for you when you get back."

"Thank you!"

I exited the door and Harry was just there standing.

"What do you mean by that?"

He seemed unfazed.

"Oh, you know. Nothing I guess." He looked away. "So you had an older sister this whole time."

"I don't know what you're talking about. I don't have a sister."

He started walking away slowly and I followed him.

"I ran into your moms the other day. Boy, we had a laugh or two..."

"I would not trust a thing those witches say. And neither should you. Mothers are evil. They lie and manipulate you your whole life. Your mother is a great example. Remember what she did to you?"

"That's all in the past, Hope. I've moved on. What are you gonna call the little rascal?"

"There is nothing of the sort. You shut up! If this gets out I will deny it until my death."

"So it's true then?"

"I'm not confirming any of your crackpot theories. All I am saying is... I don't know. People lie. You just can't trust them."

"I don't get what you're getting so worked up over. It's a good thing. Some might say..."

He stopped in front of a nice car and took out his keys. The car beeped and the door opened. He climbed inside.

"Is that a Bugatti? How can you afford that?"

The door closed but he lowered the window.

"The thing you have to remember... Just when you... I don't know, man. Be grateful for what you have! Don't take things for granted! You never know when you might lose them. Peace!"

He turned on the car and drove off. I was left speechless.

"What an asshole! Where does he gets off telling me what I should..." I didn't realize I was speaking out loud. A little girl was standing right next to me and looking at me. "What? I didn't... the... he... ah, forget it!"

I went back to the bar and I didn't notice it but that girl was following me. I sat on my chair and the bartender handed me the beer and sandwich I ordered previously.

"4,50!" I gave him the money but he was not even looking at me. "Hey, squirt, we don't serve minors here. Beat it!"

I didn't turn around to look at the kid. I was hungry and the sandwich looked good. I did notice a hand reaching over the bar holding an ID card. The bartender looked it over several times, then the kid.

"Jesus, if you say so. What can I get you?"

"Just water please, thank you."

The bartender just rolled his eyes and poured a glass. She sat next to me and looked at me. I was pretending I didn't notice her.

"Hello, good sir! May I have your name, please!"

I was still eating so I didn't even look or respond to her.

"My name is Missy."

"Didn't ask." I said and took another bite.

"I have a mission to take home a handsome young man who will take care of me."

"Don't care."

She did not even look bothered and continued.

"I have instructions from my teachers to go out and find the one I will devote myself to."

I didn't say anything this time so she put some more effort into it. She reached down and pet my soft but still long dick in my pants. I took notice of that and stopped eating. She had a big smile on her face.

"Look lady, I don't know who you are but I'm not interested. I'm not saying you're ugly or anything, it's just... I had a tough night. Let me at least finish my breakfast."

She leaned over and whispered something in my ear which I'm not fucked up enough to repeat. Nevertheless it got my attention. She asked me to follow her, so I left my meal and quickly walked after her. She pointed at a car and we got in.

Next thing I knew we were at a mansion outside town. I was so nervous. Because of what she said to me, not because I was in a rich girl's house. We were greeted by a butler and several maids. As we were walking further I saw an older man in front gesturing to enter a certain room. He sat on a sofa and invited us to sit across him.

"My... daughter seems to have some interest in you. I've waited a while for someone to pawn... I mean give her hand in marriage. What's your name, young man?"

This seemed suspicious as fuck. Why was he pausing and correcting himself? Instead of playing along, I decided to confront him. You know, before situation gets out of hand... like it usually does.

"What is going on here? We met like... I don't know, 20 minutes ago. This whole thing... what is it?"

He laughed.

"Straight to the point, I like you. My daughter seems to have a good eye for potential suitors. Here's the deal. For a graduation gift, I have decided to let her marry whoever she choses. As for you... you get to inherit this whole mansion. Seems pretty good, no?"

"Ok... why? Is this some kind of scam?"

"It does seem rushed. But I assure you it is all legit. Officially you will get the mansion and the girl. Unofficially, however, we all turn a blind eye to whatever you decide to do with her. Permanent damage is allowed, within limits of course. She is okay with anything, as she was trained that way."

"Trained?"

"Have you heard of the Sissy Academy? Very nice place... one of it's kind. She graduated with flying colors. I am so proud of her."

"Sissy Academy? That's just in name, right?"

"A school for sissies. A training ground for any boy who really won't grow to be a man."

"That kind of place is allowed?"

"It's encouraged. She wouldn't have made a name for herself as a man, that much was obvious. But as a sissy... her future is full of joy."

"She's a... a he?"

"Is this your first time seeing a..."

"No, I've seen some things here and there. But she looks so real. I wouldn't believe she is a sissy."

"Flip up your skirt, sweetie! Show him your fufu clip!"

She did as instructed. She was not wearing any panties underneath. So she was sitting bare-assed on those dirty bar chairs. I know I wouldn't eat her ass until I see her wash it thoroughly. Also my first time seeing a fufu clip. Those were popular back then.

"You seem like a manly man. For the outside world you will be the man of the house. She will be your lovely wife. But inside... if you want a kid you can take another woman, it's totally up to you. I'll hook you up with a high paying job so you can enjoy life."

"Actually I recently got a small fortune, so I'm good on that front. How old is she?"

"25! You think the academy deals with minors? As soon as you finish high school... or even if you don't. At least 18, that's their policy."

25? Older than me.

"How exactly do we do this? I'm not really interested in marriage. Not like this..."

"The wedding ceremony will be held a week from now. We'll prepare everything. Don't worry about anything, you just need to show up. We will give you a nice suit and some... heh heh... accessories. Also if it's not too much of a bother, would you please refrain from... uhm... pleasuring yourself during that time. Gotta have them balls full for the wedding night."

I thought about it and agreed. I didn't tell them I had no intention of showing up. Like I said, this was very suspicious. I wouldn't be shocked to find out my organs are missing after I fall asleep in this weird house. Anyway I went home, my home, not my moms'.

Later that evening as I was preparing to beat my meat to some questionable content, the craziest thing happened. I thought to myself that it might be real and I should marry this cute sissy and become a rich douchebag living in a nice mansion. It's all upside... if it was in fact real. I wondered why me though. Could've been any other guy on the street.

A week later I was in the mansion getting dressed. Yeah, I know. But it seemed legit. I did not touch my cock for a full week. Right after I got a growth spurt. Such a waste. But I was faithful. A maid knocked on the door asking if I was ready. I rushed outside and slapped the maid's ass and gave her a wink as I walked past her. She blushed a deep red and attempted to cover her smile.

I went to the chapel which was inside the mansion for some reason and headed to the altar. Only a few people were there, mostly maids. After that more people started coming in and sat on the chairs. Finally the bride walked in. I've been to a few wedding myself and I got to tell you the bride is always the most stunning person in the room. But this was not the case here. Yes, she was very stunning but for the wrong reason.

See, her dress, if you can even call it like that, it wasn't really screaming "Bride". It was mostly saying "Sissy slave... bride". I don't know how they managed it, but they sure made a mockery out of this fine lady. Still, she didn't look distressed. I found that very charming. The more I looked at her, the more lovely she appeared. Was I falling in love?

I mean, it did happen before, but that was my sister... who I didn't know even existed. Falling in love with siblings is normal... so I've heard. Nothing unusual about finding them attractive. That is until you cross THAT line. Which we did of course, but in my defense, she knew about it before me and I guess in our family this is considered normal. But I'm getting sidetracked.

My soon to be wife approached me and I got the chills. The guy next to us was talking and I wasn't listening, but I did catch "sissy slave", "obedient pet", "devoted fuckdoll" and some other words that really stuck in my head. Finally someone said "Oh, yes, the rings!" I snapped out of my daze and took her ring. Or at least what I thought was a ring. It was of course a ring, it's just... was a part of a very peculiar device. It was in fact a chastity cage, but it didn't look like one.

"You may lock the sissy clitty."

She lifted her frilly dress and exposed her very tiny and very feminine penis. I carefully took her ballsack and penis and put them through the ring. I was passed a leather strap that was placed around her waist and locked in place. Now the ring was not going anywhere. The last piece of the puzzle however was the "cage". It looked more like a... well I don't really know what it looked like. It was the first time I saw something like that. Missy realized I was having trouble and helped me out.

"This tube that sticks out... Put it inside me peehole."

Now I remembered what was in my dick when I was with that asshole. It didn't look quite like this though. Also inserting it inside anyone's peehole, ugh, it hurts me just by looking. She didn't look hurt, but it did seem to put some pressure on it. Next part was the... what is it? How do I even put this on?

"Push my clitty inside my body with the shaft! Keep going until you lock it and make sure it's tight."

I locked it and boy was this a journey. This was my first time with an inverted chastity cage. Missy was still expecting more. I was then given a tube of super-glue.

"Coat the key with it and put it inside the lock again! Then, break off the key! It should stay inside now."

I was shocked. This was well past being just a kink. This is something permanent. Even though I knew there was no going back if I follow through, the idea excited me to no end. I still did it and Missy shivered and let out a moan.

"Now the bride will put the ring on the groom."

Missy dropped on her knees and unbuckled my belt in a flash. She dropped my pants leaving only my boxers on. I immediately covered myself. I wasn't on board to have something like that on me. Then I saw the ring. I realized it was a cock ring as it was much bigger and had the words "Sissy slave owner" engraved on it. I let Missy pull my boxers down and put the ring around my dick.

"Uhh... huh? What do I do? This... was this always like this?"

Nobody could have predicted this. I certainly did not expect it. My massive cock which I had for a little over a week... had shrunk to a size smaller than Missy's little dicklette. Chaos ensued. The crowd started screaming.

"What is this?"

"What is going on?"

"I don't think this will work. Should we continue?"

"I came here to see a sissy wedding and as God is my witness, there will be a sissy wedding."

"We can't have our sissy marry some guy with whatever that is between his legs."

"Is he a sissy too?"

"Was he just pretending to be a real man."

"Was Missy tricked?"

Missy then shouted.

"Be quiet! Let him explain himself!"

I was wearing the most real poker face there ever was.

"Honestly, my guess is as good as yours. When you saw my dick a week ago, I genuinely had a big dick in my pants. I did not masturbate for a whole week just like you wanted. I'd say I wanted you to experience the surprise with me. But this? I have no idea... well, it actually happened before, but not like this... Maybe... Maybe a little stimulation will help it grow."

Missy looked skeptical but she also attempted to give me a blowjob. It was hard to look at. It was sexy but seeing it done to me made me feel uncomfortable. She was also struggling. With that size all she could do was lick it. It was not getting bigger nor was it getting harder.

"It feels as I'm licking the clit of the headmistress."

That was a fair comparison. To me it felt like I had my clit licked. At least I assumed women feel it that way. The crowd was getting restless. I was afraid they would be violent. I had to come up with something. Think, Hope! Why did you dick shrink before? And why did it grow to such size? The first time it shrank, I honestly believed it was the flat chastity cage that bastard put on me. When it grew... it was after my moms and sister fucked me senseless.

But what does that have to do with anything? Why did it shrink again? I wasn't wearing any restrains this time. Was it the fact that I wasn't masturbating for a whole week? It seems stupid now, but at the time this was the most logical answer. Solution? Masturbate like crazy every day. I excused myself to my changing room, saying I have something that may improve the situation. An obvious lie, but they seemed to buy it. I went to my room with a couple of maids who were left standing outside. Immediately I looked at the window.

I opened it as quietly as possible and checked my surroundings. Nobody was outside. Obviously as everyone was inside the chapel. This was my way out. I mean, it's not like they would beat me up for deceiving them. I had a genuine shock on my face when the reveal happened, but would that matter? The plan is simple. Get out of there, avoid contact at all time, stay low and generally... don't leave the house? Man, this seems tough.

I mean they don't know me. They know my face, but not my name or anything else about me. And surely I can manage to work from home. I'd think about it when I get home. Now... the window was at the third floor. There were no railings or bushes or even a tree. It was a 6 to 7 meters of free falling between me and the ground. I don't expect you to believe me and I have no way to prove it to you now, but I swear it happened exactly like that. I jumped out the window, landed on my feet, did not broke or even bruise anything and just hauled ass home.

About 4 days later when my food supplies were getting low, I decided.

"Man, fuck this! I gotta get in shape. Gotta do something about my living situation."

Can't go outside and risk someone seeing me. Can't call my moms or Kat about this because I don't want their charity. And then I remembered. A long time ago... actually not that long, I used to stream sissy videos of myself for money. This was still an option. But this time I had to get creative. I had to change my face only for the camera. And boy oh boy, there was a lot of options. I made the most sissy persona I could ever imagine and just ran with it. Another good thing about it was that I didn't need to apply any make-up. So... a typical day looked like this.

I wake up around noon. I eat breakfast. I take a shower and clean my bowels. I spend 2 hours doing exercise to maintain a good flexible figure. Then I set up my gear and stream the rest of the day and night, taking short breaks to eat snacks. Another thing that streamers did at that time was "goals". They set up a certain sum of money and when the viewers hit that goal, the streamer gives them a rewards. Boy that was a mistake. At least the way I did it. I set up an individual goal of "I'll be your personal sissy slave for 20 thousand". Bro, that shit was completed in 2 minutes.

Damn.