Hope's Life Pt. 01

"So are we doing this or what?"

As good as she looked, she was towering over me with the black 15 cm high boots she was wearing. Her belly was exposed and I almost went for it but she stopped me.

"Not here. Upstairs. Your bedroom."

"Awww, yeaaahhh."

We went to my bedroom and just as I was opening the door, I remembered. I didn't put away all the sex toys I was playing with earlier. I closed the door fast and looked at Ellie.

"Look, why don't we go to your place? My room is a mess right now."

Ellie opened the door and pushed me inside.

"This is happening. You asked for it. Now, man up!"

As soon as she walked in, she saw everything. She looked at me. I was speechless. I mean what do you say?

"Told you it was a mess."

Apparently not that.

"Are these yours?"

"What? No. No. Yes. But let me explain."

"Shush. Go to your kitchen and pick some food. We'll have dinner here."

I quietly exited the room and went downstairs. I opened my refrigerator. It was empty. All I saw was a cucumber, chocolate cream and a bottle of milk. I can't make dinner out of that. It's better than nothing. I took them all out and returned upstairs. When I walked in, I was in shock. All my sex toys were organized by size on the table. Ellie was sitting on my bed and dangling the keys of my chastity cage I was wearing. How did I forget to take it off? She smiled at me.

"I couldn't find what these unlock. I thought for sure you had a diary. Why don't you take off your pants and show me what you're hiding there?"

It was all lost now. She had the keys to my chastity. The ball was in her field now. She pulled all the strings.

"Hurry up, darling. Show me your pathetic boy clit you thought you had a need to lock away."

That was the trigger. My dick started to get hard in its cage and I bent over trying to keep it soft. Ellie stood up and walked over to me.

"What are we having? A cucumber, chocolate and milk? Not bad. It will do. Now show it to me."

"Wait, let me explain."

"If you show it to me, I'll show you mine."

Now I was curious. I haven't seen her dick even once. I wondered what it looked like.

"Okay, here we go."

"Together."

I slid my pants down revealing the pink chastity cage. Ellie lifted her mini skirt and slid down her panties. Her cock popped out, tucked between her legs. I was staring and marveling at the wonder of nature. Ellie was smiling when she saw my expression. She went to unlock it and took the cage off. My dick was hardening fast and in a few short seconds it was fully erect. Ellie began to laugh hysterically.

"Is that it? When you wanted to have sex with me, did you mean you wanted to be fucked?"

At 8 cm, my fully erect cock didn't seem as impressive as I thought it would be. Ellie grabbed her dick and slapped mine with it. It was both exciting and humiliating.

"Ah, this is so cool. We are gonna have so much fun tonight. Undress! Now!"

I didn't take Ellie as the "in-charge" type. She seemed more like a beta at best. This new side of her... it was nice, I guess. It fits her. I took off all the clothes I was wearing and waited for further instruction. I was her bitch now. Ellie took a step back and looked me over.

"Are you a virgin?"

"Well, sort of."

"What do you mean "sort of"? Either you are or you aren't."

"Well, how do you define a virgin?"

"Have you inserted your... whatever that is... in a vagina or an asshole?"

"Uhm, no."

"Has a real dick penetrated your ass?"

"Does a finger count?"

"No."

"A sex toy, perhaps?"

"Am I going to be your first?"

"Well... that's... you know... Yeah."

"Hmm. I'll have a lot to teach you then."

This honestly made me laugh on the inside.

"You? Teach me? Good one."

"Between the two of us, I'm the one who has any actual sexual experience. Although... you have quite the collection here. What made you buy all these toys?"

"Well, after that time with Candy..."

"Got it."

"What?"

"Yeah, you're not the first one she tried to... What's the word I'm looking for? Convert."

"Convert me? Into what?"

"Shemales are definitely not lacking in numbers, but sissies are something everyone wants. You look kinda cute."

"Who would want to be a sissy?"

"You get a lot or perks for being a sissy to someone."

"Yeah right... Like what?"

"Men want sissies for sex. Women want sissies for domination. Shemales want sissies for both. And that's not all. Older couples sometimes get a sissy for baby play. You never are quite the same after that. Some people want a sissy as a pet or a servant, a maid, a slave... a prostitute."

Where did Ellie knew all this from? Was she a sissy for Vince?

"Alright, enough of that. Get on the bed, ass up, face down!"

I did as instructed. Ellie got behind me and slapped my ass.

"Let's see how much you can take."

How much I can take? Take what? Suddenly I felt something breaching my sphincter. I looked around. Adrian was stuffing the cucumber inside me.

"What...?"

"It's dinner time, baby. You'll love this."

She was slowly advancing the vegetable inside my ass and it felt good. Every 2 cm she pushed in, she pulled back 1 cm. At some point she stopped pushing in. Instead she started fucking me with it.

"How do you feel?"

"Oh, yes, it feels so much better when someone does it for me."

"Does it now? It looks like we have a lazy slut here."

"I don't care what you call me, just please don't stop."

As soon as she heard that she stopped and pulled it out. I looked at her with pleading eyes.

"We did you. Now you do me."

She handed me the greasy cucumber and assumed the same position I did.

"Push it in slowly, baby. Don't worry, I can take it."

I did what I was told and pushed it inside her. It went in without any resistance. Her ass was trained well.

"Start fucking me with it, baby!"

I immediately went to work. The cucumber was sticking out and I shoved it down and pulled out. It felt like I was stroking my own cock. Ellie was moaning every time I plunged it in.

"HARDER! FASTER! DEEPER!"

My hand was getting tired. This was going for a few minutes already. When would be my turn again? Ellie's butt began to tighten and she shivered. I knew what was going to happen so I pulled the cucumber out. Ellie looked at me in confusion.

"What are you doing?"

"Uhm, you see..."

"I was about to cum."

"I know. That's why..."

"You never take it out when someone is about to cum."

"Oh, but when you do it..."

"Listen here you little shit. I call the shots around here. What I say, goes. You better remember that."

Who was that? Was this Ellie? I don't think so. It's like her evil twin sister. I was not comfortable with that.

"Why are you being so mean to me?"

"Me? Mean? You have not seen mean my friend. I am being very gentle here. What did you expect was gonna happen tonight? Did you think I'd let you fuck me or something? You get to serve me. You get pleasure from me getting pleasure."

"But... but... that's not fair..."

"Don't talk to me about fair. You know nothing. You want sex, huh? You'll get it, homo."

"What..."

Ellie grabbed me and turned me around, pushing my face down. My ass was exposed and she violently stuffed the cucumber inside and began to fuck me relentlessly with it.

"You like that you little bitch? Huh? You like it?"

I was experiencing both pain and pleasure, but mostly pain. Ellie was merciless. She fucked my ass for about 10 minutes before she flipped me over and sat on my face. Her legs were keeping my arms immobile, I was totally helpless. She grabbed my dick and pulled hard, making me raise my hips altogether. My legs flew towards her and she grabbed them, securing them under his armpits. Now I was totally unable to move.

"Do what I do!"

She pulled on my body and her tongue entered my gaping asshole. Since she was sitting on me and her own asshole was directly on top of my mouth, I darted my tongue inside her. She was good, I have to admit, the way she explored my asshole with just a tongue reminded me how experienced she really was. I tried to keep up, I didn't want to make her think that I was slacking off.

"Oh, look at that. Our dicks are kissing each other. Let's not leave them alone!"

Ellie lifted her ass from my face, giving me time to take a breath, then she guided her semi-erect cock into my mouth. It wasn't bad. But then...

"I love your gaping ass. You have trained it well, sissy. But have you tried this...?"

My asshole became very wet and cold at the same time. So much that it went from gapping to closing in milliseconds. Ellie slapped my cheeks and inserted the cucumber again. She fucked me with it for a bit while I was slurping on her still soft cock. Every now and then she would remove the cucumber and put the same stuff again. I figured it was the milk. I really wasn't sure why this was happening, but I just went with it. As soon as my ass was filled up, Ellie put the cucumber again. I was relatively relaxed at the time so I didn't even notice that she was using the cucumber to push the milk deep inside my guts. This process continued for a while until Ellie said:

"All done. How do you feel?"

She waited for a response before remembering her dick was in my mouth. She let go of me and my body fell hard on the bed. My god, it fell so hard... the cucumber that was still inside me broke in half and I somehow sucked one half in my ass. Ellie was close to laughing but she gave me a smile instead. She climbed off of me and stood up stretching herself.

"That was fun. It's getting late though so... we better finish up here."

I sat on my bed and my guts were rumbling. I look over to my little table and saw the empty bottle of milk. A 2 liter bottle of milk... that was unopened I might add. I was feeling the milk going down to my ass again and realized I had to go to the bathroom and evacuate my bowels. Ellie was having none of that. As soon as I stood up she grabbed me and spun me around.

"No, no, no. You stay here. We aren't finished yet. We didn't have dinner yet. Before we continue, I have a few questions. Have you had an enema before?"

"Uhm, yes."

"And today, specifically before I came did you have one?"

"I did."

"Good. You know how to care for your body then. And keep it clean. Ok this is how we'll do it then. Get on the bed and lie down! Your ass hanging from the bed. I'll go down on you."

I did as I was instructed. I didn't get it but I did it anyway.

"Ok, do you know what felching is? Don't worry, you'll love it."

"You say that but then it becomes something really..."

"I said you'll love it. Now I'm going to suck the milk out of your pussy so feel free to push it out. When I give you a tap I want you to stop and clench your ass, ok?"

I nodded. Ellie placed her lips on my hole, her tongue went inside me and she gave me a thumbs-up. I concentrated on pushing the milk out, but that damn cucumber was blocking the entrance.

"It's not coming out. The cucumber..."

"I think I got it, thanks. Just relax, don't push for now."

She inserted a finger inside me and then two. She was trying to loosen me up again. Poking around inside me she located the cucumber and managed to guide it out.

"Push, slowly."

I understood what she meant and tried to push the cucumber out without spilling any milk on the floor. I don't want to make a mess. And I am a little scared that Ellie will make me lick any mess I make on the floor. The cucumber plops out and falls in Ellie's hand.

"I'm sorry to say this, madam, but your baby is a vegetable."

She put her lips on my ass again and I pushed the milk out. She quickly gave me a tap and I clenched. She stood and pushed her face into mine. Her cheeks were like a squirrel's. She planted her lips on mine and I thought she was giving me a kiss at first. Soon she was pushing the milk in my mouth. There was nowhere to put it so I started drinking it. It wasn't bad at all. My ass was clean, so it just tasted like milk. Ellie lifted herself from me and gave me a wink.

"We'll do this until everything is out of your system, ok?"

"God... this will take forever..."

Ellie grabbed my hand and lifted me of the bed. Then she reached down and scooped me like princess. I didn't know she had it in her. I also didn't expect for this to happen. I was never carried like a princess before so that was a new sensation for me.

"Right you are, slut. Where is your kitchen?"

"It's... it's... downstairs. Could you please..."

"No time!"

She rushed me through the door and slowly carried me down the stairs. I motioned to her where the kitchen is and she walked in. She let me down on my feet and I covered my face trying not to show how embarrassed I was. She didn't care. She looked around and took a pitcher. She left it on the floor and pointed at it.

"Here."

"Here?"

"Yes, here. Don't worry I won't look."

This was the least of my worries. I squatted over the pitcher while Ellie averted her eyes. This was so humiliating but I just wanted this to end. I pushed and the milk started flowing out. It took, maybe, like 5 minutes before everything was out. I got up and touched my asshole. It was a little prolapsed but nothing serious.

"All done."

Ellie looked at me, looked at the pitcher and then she motioned for me to pick it up. I rolled my eyes and did as instructed. She was looking at me with expectation.

"You want me to..."

She nodded.

"All of it?"

She nodded again. I didn't think I could drink the whole thing but I was wrong. It wasn't easy, I had to take short breaks but in the end I drank it all. I gotta tell ya, for a liquid that was inside my poophole, it was surprisingly tasty. I gave a loud burp and put the pitcher down. Ellie gave me applauds and smiled. She gestured to come to her and I did. She picked me up like a princess and carried me over to my room.

"You did well, sissy. That was a nice warm up."

That was warm up? My belly was full and I was about to tell her to go home so I can go to sleep.

"You called me over for sex and that is exactly what we are about to have. Don't be shy. I know you want it too."

She carefully placed me on my bed and took the bottle of lube next to her. She poured some on her fingers and slowly inserted them in my pussy. I mean asshole. Let's not do this again. She fingerfucked me for 5 minutes before she lubed up her cock and plunged it into my hungry pussy. I did it again. Maybe I should just call it a pussy from now on. It is more fitting now anyway.

"You're being gentler now. What happened?"

She didn't answer me. Instead she went and kissed me while slowly moving her hips in and out of my lustful pussy. I didn't care. It was hot. I didn't even care how gay it was. We may fool ourselves but come on... it was pretty gay. We were just a couple of faggots banging. Of course at this moment I was feeling more like a woman and she was looking more like a man. This was messing with my mind. Was I turning into a cock crazed slut? Her pace quickened. I started to pant and moan but she was still kissing me. She grabbed my hands and pinned them above my head. I was feeling so helpless and vulnerable. It was getting even hotter. At that moment I knew, this is what I was born to be. I probably would have regret it later but tonight I was a happy cock loving whore.

"Have you ever had an anal orgasm before?" Ellie asked.

I was so far in the zone I didn't even feel embarrassed anymore. I could tell her anything she wanted.

"Yes, yes, yes. I have it all the time. It is the best feeling ever."

"Good. If you are gonna be fucked like a woman, it is only reasonable to cum like a woman."

My head was spinning. I was ready to sell my soul and freedom just so this night can last forever. I was entering a dangerous territory. After fucking me missionary for a good 20 minutes, she flipped me over and pounded me doggy-style. I was feeling so good that I didn't even realized when I started to fuck myself against her. Ellie took the opportunity to reward me with a few slaps. As soon as I felt them I clenched and started fucking myself even faster and harder. She was chuckling and kept smacking my ass.

"Are you close to cumming, little sissy?"

"Not yet, keep going!"

And she did. She pushed my face down and climbed over me. Now her cock was sliding down my ass and she was increasing the tempo. I moaned and she enjoyed that. Every now and then she would slap my cheeks again. It took over 15 minutes of doggy humping but she finally tensed and jizzed inside me. I was a little disappointed as she told me I will have an anal orgasm. But instead of pulling out, Ellie just kept going. She made a quick turn while her cock was still inside me and started drilling me in this weird new position. I have to say I didn't hate it as her cock was rubbing my prostate and it felt amazing. So much so that I began dribbling cum from my clitty.

"I'm cumming. I'm cumming."

She stopped for a moment and flipped me around again. This time she pushed my legs over my head. She thrust her cock in my gaping hole and mercilessly kept scraping my prostate. It was working. This time it was strong and consistent and in a few thrusts my cocklette was spurting cummies all over my chest and face. Ellie smiled and kept going. At this point I was starting to fade away. The experience so far was exhausting me. "But, Hope, Ellie is doing all the work while you just lie there taking it..." Yes, but I was fucking myself earlier when she interrupted me. Add this to the equation.

"Yo, babe, are you feeling ok?"

"Yes... just... gotta... take... a quick... breath... ha... ha..."

"No can do sweet cheeks. I still haven't had enough. After this I have more planned for tonight. Just you wait... and then we will... until morning... can't wait to see..."

These were the last words I remember before losing consciousness. I won't lie to you. It was intense. I just wanted to go to sleep. Next morning though...

My phone woke me up. I had 3 missed calls. All from work. It was 2 o'clock in the afternoon. I sure slept like a baby. Felt refreshed and all and ready to start my day. I missed work but I didn't care. I started getting up. My room was clean. Seems like Ellie cleaned after me last night. I should thank her. Of course when you think about it, it seems like the cleaning was a thank you from her for the wonderful fuck I was last night. At least I hope so.

Right off the bat I noticed the rubbery object in my mouth. I spat it out and I kid you not. It was a pacifier. That was weird. I don't know where it came from or why it was in my mouth... I didn't know anything. I flipped my blanket. What had happened last night? What did Ellie do to me? The questions kept coming one after another while I was staring at my diaper. Yes, you read that right. A diaper. On my crotch. I began taking it off. No way am I just gonna stay like this. As soon as I flipped the front of the diaper, I saw my cock locked in a chastity cage. Here is where it gets weird. It wasn't mine. It was different, slightly smaller and covered in jewels. Now what? I stood up and stretched a bit and then I saw the note on my desk. I picked it up.

"Hey, Hope. I had lots of fun last night and I hope you did too. I cleaned your room as a thank you but my services come with a price. By now you should have noticed the diaper I put on you. Just a precaution in case you poop yourself while you sleep. I made you quite loose last night. Anyway, I made you breakfast, just have to reheat it. See ya tonight.

P.S. I put my favorite chastity cage on you just for good measure. I don't want you to chicken out on me. You better come tonight or I won't unlock you.

P.P.S. I ate your breakfast. Don't get mad.

P.P.P.S. I took your laptop. I kinda became your fan as well. Awesome porn bro, keep it up."