A Better Life through Chastity

"Go to bed babe," he said, smacking her playfully on the ass. She blew him a kiss and left the room. I sat on the edge of the bed looking down at the cage, when I heard the rattling of a key and glanced up to see Michael attach it around his neck in a necklace. "If you want to earn release, you'll have to please me instead."

I looked down and his cock was twitching. There was no way I was going to do it, I'd rather die than pleasure him to get my key back. That's what I thought, but I felt a twitching inside me and as his cock bobbed up and down in my view, my mouth opened involuntarily. I didn't know what was happening, I didn't want to do it, but maybe I should? He walked towards me and in the dim light of the room I could see all the veins on Michael's cock as they bulged.

"You know we ditched that dildo, so my cock is the only way you're getting off now, but that's okay, because I know you want it." I couldn't take my eyes off it, he kept walking towards me, sitting down on the bed next to me I got up and watched as he lay down on the bed. I stood above him, his hard dick standing to attention proudly. I turned him on.

"It's no good trying to fight it, I know you want this, if you want to cum, you'll have to ride me." I didn't want this, I knew I didn't want this, my hand started rubbing my cage uselessly. This was wrong, I didn't want this, but I did want to cum. God I wanted to cum. He grabbed his shaft and waved it around, signalling me. I wasn't going to do it, I couldn't, this was so fucked up. I lifted one leg onto the bed and got on my knees over him. He smiled up at me.

"The sooner you learn to accept this, the better." I moved over him, his dick traced along my cage right to my waiting hole. This was awful, I didn't want this. I grabbed his shaft and pushed it to my hole, he moaned as I slowly eased myself down onto his wet, waiting dick. His hands gripped my legs and held me in place as I slipped down onto him, impaled on his cock, my cage slapped against his stomach.

"Good sissy," he uttered through a grin. In my head a voice of reason was fading as the feeling of Michael's big hard dick fucked my ass. I started to grind hard on him as my ass slapped against his crotch, my cage flapping about, I was being fucked like a little bitch and it was amazing. Michael squeezed my thighs and I looked down as his neck as the key bounced on his chest... if I could just grab it off him.

I leaned forwards, placing my hands either side of his shoulders as he angled his cock to penetrate deeper inside me. I was so close, if I could just grab it, it would come off and the key would be mine. I edged closer with my hands as I felt Michael suddenly hit the pleasure spot inside me, I moaned involuntarily and fell onto his chest, my face inches from the key. But my plan was ruined when his arms came down and held me in place, I watched helplessly as the key bounced around on his chest and the pleasure built inside me, I let out a whimper as I came, cum trickling out the cage onto Michael's chest. At the same time I felt him convulsing and... oh no. My sexual frustration subsided and clarity returned as I felt Michael's cock fill me up with his seed. I stared at the key as his body relaxed. He started to laugh and said he knew what I wanted. He pushed me off him coldly and I lay there on the bed with cum dripping out of me.

"Wearing it as a necklace is a stupid idea, I think we better keep this hidden from you, can't have you getting ideas sissy boy." I watched as he got up, removed the necklace and shut the door behind him as he left the room. I felt used, but relieved. A part of me had died, but was it hope or self respect?

I awoke the next day, feeling all the life drained out of me. It was a work day, I didn't know what was going to await me at work but I knew staying at home wasn't something I was into either. Plus, listening to Michael and Sophie fuck all day, humiliate me and make me serve them food was, in my mind, pretty close to torture. I didn't want to go, I didn't have the energy, but if I was going to break free of this I'd need to keep my job at least. I glanced towards the wardrobe and saw a sticky note placed on it, bright pink to grab my attention. I sighed, of course it's pink.

I picked it off the front of the wardrobe and read it, "Your new wardrobe." I knew this was going to be bad. I pulled open the doors and saw a few dresses, blouses and skirts, a maids outfit and several slutty outfits that were totally obscene. I wasn't surprised to not find a single male piece of clothing in the wardrobe at all. Searching the wardrobe for the least feminine of the female clothes, I eventually settled on a t-shirt with a generic girly logo, which I figured would be better than a floral dress. For the lower body the best I could find were jeans which accentuated my ass way more than I'd like. I looked like a boyish teenage girl in this outfit but it wasn't too bad, at least I looked sort of boyish. The more I stared into the mirror the more I felt foreboding swelling inside me. What is Sarah going to make of this?

As if reading my mind, my phone vibrated on the bedside table. It was yet another message from her. She was looking forward to today and sent a picture of herself smiling a mischievous smile. I had to admit, she was cute when she wanted to be, but she was definitely up to no good, and it would probably be bad news for me.

I looked around the house before leaving for work trying to find a jacket or something to wear over the t-shirt, but couldn't find anything. I even thought about stopping on the way to work to buy a more reasonable wardrobe, but I'd not be able to bring it home without it being confiscated by either Michael or Sophie. I sneaked past the master bedroom and saw the two in an embrace on the bed, I felt sad. How did I become a servant in my own house? I kept going and made my way into work trying to keep as low-key as possible.

Sarah was already waiting in the conference room. I opened the door to a wolf whistle from her, I ignored it and dragged myself to a set and sat there. She looked a little dismayed that I wasn't responding the way she hoped. She walked over and sat on the desk in front of me.

"What's up buttercup?" she said in a sing song voice, drawing my attention up to her seductive eyes. I tried not to respond, but Sarah was too disarming at the moment for me to ignore her. I had so many anxieties, everything was terrifying and my emotions were out of control, despite how badly I tried to bury them. They all came bursting out.

On the verge of tears I explained everything, from the very beginning. Sarah sat and listened as I retold all of the humiliating scenario's I'd been in and why I was trapped in my own home. When I finished I just sat in silence, feeling defeated.

"Well that's pretty hot," she said looking down to me and winking. I knew telling her would be a waste of time, what was she going to do? She got up, moved the desk back and straddled me in the chair; it was awkward.

"So, you're telling me you don't want to be their sissy slave?" I shook my head. "Aww, that's cute. So, how about I set you free?" My gaze darted up right into her eyes. What? How? She was projecting a radiant smile, full of confidence and certainty. I was still confused. She lifted herself off me and crouched next to me.

"Would you rather be my sissy instead?" My heart sank, I didn't want to be a sissy at all!

She put her hand on my thigh and said to me that there was no denying what I'd become, she told me a stronger person would have rejected all of the things I'd done up until now and that I was in denial. I thought back to the website and looked down at my girly t-shirt. Was this who I was now? I looked into Sarah's eyes again and it felt like I was being hypnotised. No, she was wrong. The chastity cage made me do all this, I didn't want to do any of it, I told her. She calmly explained it was part of who I was now, Michael and Sophie would never remove it from me and even if they did, I couldn't use my little dick any more.

Sarah put her hand on my cheek and said "It's staying on, you have to accept that."

I didn't want to hear this, sexual frustration for the rest of my life? The more I thought about it the more I knew it was true though, I couldn't get the key and I wasn't able to get hard either, I just didn't want to hear it.

Sarah stood up, towering above me and explained.

"You have this one chance, you can stay with Michael & Sophie and be treated like shit by those two. Or, you can be free with me."

I didn't want to be serving meals and sucking Michael's dick until they grew tired of me, what would happen then? Would they kick me out? This thought plagued my mind as Sarah patiently waited. I looked up and asked her what life would be like as her sissy. She smiled.

"I'd treat you like the little princess you are, of course." I could tell she wasn't going to elaborate more than that. I didn't know if I liked the sound of it though, it was ominous, but I'd rather be a princess than a slave.

I said I'd go with her. She giggled with excitement and dragged me out of the chair and gave me a huge hug, grabbing my ass and whispered in my ear. "We are going to have so much fun cutie." Part of me liked this positive reinforcement, but I was pretty concerned as to what this fun was going to be.

The next twenty minutes was an absolute trip. Sarah revealed things to me that I would never have suspected. She pushed the button down on the intercom in the conference room and called my boss in. A few minutes later, he strode into the office and stood next to Sarah, my boss was an imposing man, the picture of refinement, I felt intimidated sitting there in a girly t-shirt in front of him. She smirked and said "Show him." she said firmly.

My jaw dropped, the man before me dropped the trousers of his business suit to reveal some silky pink underwear, he removed them and there was a black chastity cage. I was astounded. Sarah produced a key from her purse and dangled it between her fingers, I watched as my boss started to beg Sarah for the key, she held him back and pushed him to his knees.

I watched as my employer pathetically grabbed her thighs, kissing them and repeating his plea for the key to his chastity cage over and over. I almost smiled. Sarah told him he was a pathetic loser, to which he agreed, then she asked him if he wanted her dick and he nodded and continued his shameful act of kissing her thighs. "Maybe later." she said with a wink. This alone was enough to get him excited and thanking her. Her tone changed, she explained that I wasn't going to be in work for a few days and that if Sophie called about my whereabouts then he was to answer that I'd quit my job. He nodded, planting more kisses down her legs to her feet. Sarah uttered "Good boy." as she turned to me and smiled widely.

Whilst it was entertaining to see who really ran the show at my workplace, I was shocked to discover that Sarah was the one who organised my meetings with her to begin with. From the second she found I'd been accessing the sissy porn website at work, she had told my boss to assign me to her for training. She admitted this to me in full, confessing that it would wrong not to tell me. She didn't know what had been going on at home for me though, but judging by her face during the talk we had about what I'd been going through, she didn't think it was very healthy.

Sarah had a few more hushed words with my boss before making him dress himself again and leave, she perked up and turned to me and told me it was time for me to relocate. I was confused, but followed her lead to the car park and into her compact, I sat in the passenger seat and the car smelt of perfume. It was intoxicating. During the car ride, she explained to me how unhealthy and damaging the relationship I'd had with Sophie was, Sarah spoke like an authority on the subject and it was reassuring to know that they were in the wrong and I hadn't brought this whole thing on myself.

I thought back to my time with Sophie, as Sarah drove me to this mystery location, I thought of the good times but recent events tinged everything with betray and sadness.

We pulled up to an apartment building, Sarah got out and I followed as we went up in the lift to the 3rd floor. She walked up to a black door at the end of the corridor, reaching into her purse she presented a key and opened it.

Sarah's flat was... unique. The dark purple walls were decorated in bizarre art pieces and racking for various harnesses. Dark wooden cabinets were topped with an arrangement of various sized dildo's in an variety of colours and unidentifiable sex toys were spread out among them. Some restraints were hanging from the ceiling on the west wall, like something you'd see in a dungeon. In the centre of the room a big TV was planted on the floor in front of a ragged sofa that had various underwear and unwashed plates coating it. It was obvious what Sarah prioritised.

She lead me to her bedroom and more discarded underwear awaited, the room reeked of sex and her unmade bed was framed by dresser's with more adult toys and bottles of lubricant on them. Posters for bands I didn't know were covering the walls and a fluffy black rug was just visible under various clothes. I'd never seen such an untidy place, but it was surprising she lived in this, it looked more like a sex dungeon someone had recently moved into.

"You'll be sleeping with me," she said bluntly. I looked her up and down again, I was fine with this. She lead me back into the living room and told me to stand underneath the restraints, I was instantly on edge, I trusted her more than I thought to go into her home, but I was not okay with this. She looked me deep into my eyes and said she wouldn't hurt me, as she gently lifted my arms into the air and handcuffing me into place. I was nervous. She got down onto her knee's and removed my jeans, I really didn't like where this was going. I felt the cold air from the window brush my smooth thighs as she removed my polka dot panties. She chuckled with delight as she saw the new smaller cage.

"It looks really good on you princess, I swear, it's so cute. Fits you really nicely as well." I liked this positive reinforcement but I still wasn't happy about wearing the cage. I felt her handle it but couldn't see what she was doing down there, her blonde hair blocking my view. I saw her place a tube of glue on the table next to me and it suddenly dawned on me she just glued my cage shut.

I started freaking out and kicking around when she suddenly smacked my ass hard and told me to stay still. I stopped moving but was still distressed. She got up and moved her face close to mine and said "It's for your own good, they can't blackmail you with a key if it doesn't work,"

This made no sense to me, this felt like she was making an excuse to do what she wanted. She leaned in and kissed me, I relaxed completely, involuntarily. She ran her hands over me and I couldn't help but start to get turned on by it, her hands caressed my ass as she pushed her tongue into my mouth, I just let her do it. I felt one hand let go of me and heard her pull something on the wall. Suddenly the restraints I was being suspended by were lowered and I was dropped onto my knee's where I could see her dick was causing her skirt to lift up. God, I wanted it, today had been so weird but here I was, chained up in this girls living room, staring at her hard dick. This was the most comfortable I'd been all day.

I watched with anticipation as she freed it from her cute underwear, it sprang free inches from my lips and I leaned forward to try and lick it but she moved away before I could connect.

"Beg." she said, looking down on me. I couldn't help it, I begged. I wanted it.

"Please Sarah." her face turned back into a smile as she took a step forward and I licked her dick from the underside of her shaft up to the tip. Her hand came down and stroked my hair as I licked her dick. This didn't feel wrong any more. It felt okay, maybe because Sarah was kind to me, maybe because of everything that had happened or maybe because I'd changed. I was overwhelmingly horny but felt at peace. I enjoyed myself. She undid the restraints and as soon as my hands were free, I gripped her thighs and sucked her dick with passion and she noticed, letting out long moans of elation. I looked up and over her breasts so I could see her eyes, closed and looking up with a smile. She loved it, so I kept going.

I pulled her cock out of my mouth to lick it all over, but before I could put it back into my mouth she took my hand and leaned down and kissed me, for only a few seconds, but it felt like an eternity that ended too soon. "You're an adorable little sissy boy." the words fell out of her mouth like honey, and I ate it all up.

That evening we sat on the sofa and she cooked me what I guess was meant to be mac and cheese, it was... unique. I'd had it with croutons before but it seemed she chopped up bits of toast and added them to it. Sarah was a lot of things, but she wasn't a chef. I cuddled up to her and ate it from the pink bowl she gave me, she placed her arm around me and stroked my shoulder absent-mindedly. I lapped up all the contact and attention I could get. We were watching some typical rubbish television, a movie with an incomprehensible plot, but I was too busy staring at Sarah to try and figure out what was going on. Her eyes were so absorbing, she looked down at me and our eyes met.

"Enjoying your fine cuisine?" she said jokingly, I smiled and nodded, it wasn't bad.

"This movie is garbage." she complained, her smile had turned to minor annoyance and somehow, so did mine.

That night I felt kind of awkward climbing into bed with her, I was starting to realise the magnitude of my crush on this girl. I was infatuated with her, she was incredibly sexy but was very warm and fuzzy, for all the times I'd had with Sophie, she'd always been sort of cold, despite smiling a lot. I stood awkwardly next to the bed, sex toys surrounding me and I didn't know whether to get undressed or not. I was still wearing the same clothes I'd found in the wardrobe at home. Sarah was getting ready for bed in the bathroom and I shuffled around looking at things, waiting for her to return to tell me how this would work.

Then my phone vibrated, I withdrew it from my pocket and saw I'd missed 3 messages from Sophie. This wasn't good. I didn't want to read them, but opened the first one. It was a reminder that I needed to be home to serve them dinner. I was annoyed they still expected me to be making them dinner, I wasn't a housemaid. The next one was more of a threat that I'd be in for spanking when I got home. Ooh, scary. Then the last one was a picture of her holding the key to my cage over the toilet. The cage was glued shut now, the key was useless. These were all empty threats at this point, who cares? A broad smile stretched across my face as I deleted the messages and blocked her number. Never have to deal with that again I thought. I sighed in relief and looked around at Sarah's bedroom when she emerged from the doorway.

She was wearing a black see through night-dress, she looked fantastic, her curves were fully visible as well as her semi erect dick.

"Why are you still clothed? Do you want a night dress too?" I shook my head immediately and felt kind of embarrassed, but she only had to question me to send me into spirals of uncertainty. Maybe I did? She reached into her wardrobe and pulled out another night-dress very similar to the one she was wearing.

"Come here cutie, you're wearing this tonight." My mind was a mix of lust from the chastity cage, delight from the fact that she thought I was cute and the apprehension of wearing yet more embarrassing girls clothes. I was pretty sure I'd look horrible in it, but after changing she pushed me over to the mirror and I had to admit I looked much better than I imagined. My body wasn't anywhere near as shapely as hers was, but I didn't look too out of place in it.