A Better Life through Chastity

My mind was a mess, I shouldn't be wearing this thing at all, but in the reflection I saw how hard Sarah had become just looking at me. My lust was taking over, I was horny and I wanted her to help me relieve some pressure. I turned around smiling, to meet her smirking face. She pushed me onto the bed. I crawled onto all fours, lifting up my nightie to reveal my bare behind. My exposed ass on display for her, she wolf whistled again and I felt a brief flash of pride for giving her that reaction. In the back of my mind a voice was asking me what the hell I was doing, but I wiggled my ass as Sarah picked up something from a cabinet behind me. I felt a lubricated finger probe my ass and I couldn't stop myself from moaning, I heard Sarah giggling from behind me as I felt her hand impact my ass hard. Ouch! I felt her climb onto the bed behind me, her hands caressed my hips as she smacked my ass again. I felt her pressing her dick against my lubed up hole and before I knew it, she was in me.

I let her invade me, I wanted this, and I relaxed completely. I was so horny for her dick, I instinctively lowered my head to the bed and let out some deep moans into the mattress.

"Oh what a good sissy!" she said, picking up speed inside me. She wasn't as big as Michael, but it still felt incredible.

"Tell me you love it." she commanded, gripping my hips tight as her dick fucked me.

"I-I love it." I replied, through heavy breaths and pleasured moans.

SMACK. Ouch!

"Louder, tell me you love my girl dick." she yelled, aggressively.

I moaned again, involuntarily.

SMACK. Oof!

"Well? Come on!" she demanded, pounding me hard.

"I love your girl dick!" I proclaimed loudly.

She withdrew out of me and I turned around, I wasn't done, I wanted more! She grabbed her shaft and waved it around in my face.

"If you want it, you'll have to beg me for it."

I crawled towards her and overcome with arousal, licked her dick that had just been inside me.

"Please Sarah, please." I begged, even realising how pathetic I sounded, I ignored it all just so I could have her girl dick back in me.

She smiled broadly, "Pathetic, totally pathetic, but adorable as fuck," she said, smirking. I planted more kisses on her dick, I was still so horny. She pushed me onto my front, climbed over me and mounted me, her body on top of mine, pinning me down as she re-entered me, I gripped the bed sheets and moaned as she fucked me again.

Her arms gripped around my neck as I felt her breasts on my back, her legs on mine and most importantly, her cock deep inside me. I was in heaven, but before I climaxed she pulled out again, I wasn't so horny this time and rolled over to see Sarah kneeling over me, stroking her cock. She let out noises of pure ecstasy as her cum shot out over me, painting me in it. I hadn't cum, but pre-cum had leaked out of me and I somehow felt relaxed.

She winked at me and said "you're a mess cutie."

After cleaning me up, I got under the covers. I didn't know what to do and sort of faced away from her on my side for a few minutes, before I felt her embrace me from behind and cuddle me. It was so calming, I felt at peace as her arms held me close to her. Before I could enjoy the feeling any more I fell asleep.

As I slept, I had an odd dream about Sophie. I was at work and she was talking to me through my computer screen, warning me about something. Then I was outside and Sarah was there, dressed up in a cute pair of shorts and an explorer's hat. It didn't seem to mean anything, I tried to communicate with both during the dream but it didn't' seem to work. Seeing Sophie in a dream brought back feelings of sadness that I couldn't quell. Sarah's appearance was kind of funny to me, seeing her punk rock style in cute little blue shorts and an explorers hat.

I woke up and Sarah was still asleep next to me, I felt something digging into my butt cheek and realised she must have morning wood. I smirked and gave it a little rub with my hand.

"Don't start what you can't finish, cutie." she said. I jumped, I thought she was asleep! She chuckled and got out of bed, stretching her arms in the air and standing in front of the window. Her night dress glimmered in the sunlight and her beautiful body was a dark silhouette inside it. I gazed at her, she was perfect.

She cooked breakfast and which was further evidence that she was in fact, not a chef. The TV was rambling as she absentmindedly whisked scrambled eggs, then something that could be called toast popped out of the toaster. She sighed and pouted. I was still wearing my night dress and didn't know what else to wear so I sat down at the table in it, patiently waiting. After a few minutes of scraping off burnt bits she served up my first breakfast. Despite it's looks, it tasted okay. I said to her I liked it and she looked at me like I was insane, but as she realised I was sincere it turned into a half smile.

"Flattery won't get you anywhere with me cutie."

"Damn." I said; her full cheeky smile revealed itself. I finished the whole thing and sat there at the table, feeling exposed in her nightie.

"We are going clothes shopping for you today, none of that boy stuff for you any more, some nice cute outfits I think." she said, taking another bite of her creation.

I didn't like the sound of this much.

"But that's what Sophie and Michael wanted me to wear too," I argued.

I didn't want to go around in girls clothes, I know I didn't really have a circle of friends since I got that job, Sophie didn't like the few I had outside work and I didn't talk to them any more. I realised I was alone in the world and had nobody, besides Sarah. But I wasn't about to start dressing female full time, I didn't mind what I had to wear at home, but outside was different. She firmly told me that I was doing it, for her. I looked up from my empty plate and into her eyes. She was radiant, like a sunbeam in a sultry body. I didn't want to say no to her, but I didn't want to wear any more female clothes.

When we reached the store I was in the vaguely female clothes I'd been wearing the day before. Sarah was leading me by the hand into the ladies section. I was surrounded by sundresses, blouses and skirts. By the time we'd arrived at the store my mind was leaning towards sex again, and as much as they were embarrassing to imagine myself in earlier, now the dresses Sarah suggested to me started to look more appealing. Her seductive tone and suggestive phrasing soon had me in the changing room trying on various dresses and lingerie. I especially liked the lingerie, so did Sarah, picking me out a yellow set that complimented my skin tone. I saw my reflection in the mirror again and just like yesterday it looked strange, but as Sarah grabbed me from behind and whispered in my ear.

"You look fantastic."

My hang ups on appearance just faded away. She paid for the lot, basically a whole new wardrobe, from dresses to panties and skirts to stockings. I was deeply aroused by the clothing by the time I got home, it was tantalising; I wanted to try it all on.

Sarah placed the bags on the floor and told me to put on what I liked. I didn't know what I wanted. I liked it all. She mentioned her favourite colour was purple, so I chose a purple dress and some black lingerie. I went and got dressed in front in the mirror, but as I caught a glimpse of myself as I did up the garter belt my mind transported me back to the time I saw Sophie wearing something similar. I was suddenly overcome with sadness, what was I doing? Standing here wearing women's underwear so this girl I met can fuck me. I'm pathetic, is this really what I want? Sarah entered the room behind me. I looked deep into my own eyes, entranced, was this who I was? Who am I?

"Well hello there cutie." A voice said behind me, I turned around and Sarah wrapped her arms around me. "I'm proud of you for going shopping with me today." she said in a comforting tone. Tears spread down my cheeks, I hugged her back, tightly. She seemed confused to begin with but returned the hug.

I finished getting dressed and Sarah admired the purple outfit.

"You look like a cute boy now." she said, doing a little gesture in my direction. I smiled, and then it hit me. She still considered me a boy, but maybe not a man. I took her dick and wore girls clothes at her request, but I was still kind of a man to her. There was a lot on my mind about who I was and with everything I'd been through recently this was hardly surprising, but somehow this realisation made me feel a little better.

She ran through some work stuff we'd have to deal with when I went back, talks about department changes and a better paying job with her. It was all stuff I was partly dreading, but she had a unique way of making even the more painful tasks seem bearable, maybe it was her phrasing or her demeanour, but I just, trusted her. Then we chatted about random stuff, but before long, stuff inevitably went back to Sophie and Michael.

I was mad at them, I spoke some harsh words and Sarah encouraged my feelings. I was justified in being mad at them, they were going to use me as a slave! Thinking I was spineless enough to just go to work and come home so they could use my pay check to buy each other gifts as I cooked meals for them? They could fuck off. Sarah smiled as I vented my frustrations and sadness at how Sophie had betrayed me, how much I disliked Michael and what he'd made me do. I wanted to get them back but what could I do? Sarah consoled me for a while as we ate snacks since she didn't feel like cooking that afternoon.

"Want to go out tonight?" The words were blurted out in my direction.

"Uh, I'm not sure," I said looking down at my dress. I didn't want to go anywhere where I was going to be seen like this. Sarah grabbed me by the hand and took me up to her bedroom and sat me down in front of her dresser.

What happened next could only be described as a miracle transformation, with make-up and some stuff she had in a box, I was transformed from a boy in a dress into a convincing looking girl. I think part of me changed upon seeing my reflection. Whoever this was looking back at me, they were cute.

I pulled a lot of faces, expecting my mirror counterpart to start laughing, but no, it was me. I turned to Sarah, lost for words and she grinned back at me. There was an attractive woman in the mirror. I adjusted my black wig, my eyeliner was making my eyes so big and pretty and the shoulder length hair made me feel like I was ready to appear on the front cover of a girls fashion mag.

"What a cute sissy you are," she said.

I wasn't like her, she was a girl, I was a boy, a sissy. It did feel like I was lying to myself being like this, but it did feel good.

"Want to go out?" that familiar voice asked again, I was still nervous. "You're going out." The choice was made.

It was late evening and the stars were out, I watched as the street lights passed by intermittently from the passenger seat in Sarah's car, the radio was playing some pop hit from when I was a kid, the warm air from the air conditioning blew over me. I could see my reflection in the window; I was entranced by myself. Before I realised where I was, the car pulled up at some sort of bar and Sarah linked arms with me as we walked in.

The doorman nodded to Sarah and opened the door for us, she tugged my arm and I was guided into this glitzy club. The main room was filled with girls dancing and a few guys were spread out among them, lights flashed various colours and the music was candy flavoured pop music, in the distance I could see girls pole-dancing and a well stocked bar.

Sarah pulled me past all that and towards a curtain in the back, we went through and waiting for me on the other side was a small lounge filled with more girls sitting around on a sofa that stretched around the edge of the room. They all waved hello to Sarah, some of them got up and gushed over her, telling her how pretty she was and how they loved her clothes, Sarah replied with some modest thank you's smiled politely, turning to me to tell me she would be right back. I felt like my lifeline had just been cut as Sarah disappeared behind the curtain. The girls turned their attention to me.

"You must be Sarah's new sissy! We've been expecting a new one." I was horrified, they knew?! I thought I was so convincing, but these girls saw right through me instantly.

"We are so jealous, it must be wonderful being a sub boy for Miss Sarah, I'd love to be her sub boy!" Said the tallest one in excitement. Sub boy? Wait.

"Sub boy?" I asked. The tallest one lifted her skirt to reveal a chastity cage. Then the brunette next to her did too, so did the small red head. I was surrounded by sissies. I couldn't even tell.

"We're all sissies sweetie, different owners, but we all come here to hang out and chat on a regular basis." I felt relieved, but still aroused realising we were all in chastity devices, but also a little nervous, is this their full time appearance?

We chatted for a bit, they all asked questions about Sarah and every one of them was laced with suggestion about sex, they were obviously as horny as I was. This was reinforced as one of the sissies in the back of the room started making out with another as I conversed to the three chattiest ones. The tall sissy was called Sandy, the brunette was called Andrea and the short redhead was called Heidi, they all explained their backgrounds and went way too far into detail about fetishes, I wasn't prepared for what Andrea was into. I didn't have a girly name and whilst part of me was glad I wasn't like them, part of me felt left out, they all seemed so happy.

A few minutes and the curtain revealed a large man, he was backing into the room with a glass in his hand, but he looked familiar. He turned around, it was Michael.

I turned away immediately, trying not to make eye contact. Heidi and Sandy got up and rushed over to him and made a big fuss over him as he sat down on the sofa, the surrounded him and one of them started rubbing his crotch as the other one told him how handsome he was. I hated this, he had them eating out of his hand without even doing anything. He lit up a cigarette and I glanced at the no smoking sign, no matter where he went this guy just acted like he owned the place. I wanted to punch him in the face but I'd probably get snapped in two.

"Hey there sluts, my girlfriend is out for the night, so I figured I'd come and pay you all a visit," he said unabashedly, so he was cheating on Sophie too, I can't say I was surprised.

Andrea looked at me and said "Watch this," She got up and walked over to Michael, dropped to her knees in front of him and pulled his cock out of his shorts as the other sissies cheered her on. I watched in dismay as Andrea sucked his dick in front of everyone.

"Mhmm, good as ever Andrea." he moaned as he took another sip of his drink. Heidi was visibly jealous but Sandy looked like she was observing Andrea's cock sucking technique. The rest of the sissies in the room were suddenly over by Michael either giggling over Andrea or complimenting his dick or saying how they wanted second go.

"Who's the new one?" Michael asked in my direction. Oh no.

"Cute new sub boy, very eager to please obviously!" said Heidi, encouraging me to come over. I didn't want to but I turned around and forced a smile.

"He's cute, have you sucked cock before sweetie? I bet you're good at it!" I waved my hand dismissively.

"I haven't had any training yet..." I explained.

Andrea removed her lips from Michaels huge dick and said "Come on babe, don't be shy, Michael always has enough for everyone." she said, catching her breath. His dick, glistening with Andrea's saliva was presented before me. I didn't want to do this, but now everyone was waiting for me to do it. I couldn't deny I was horny, but I didn't want to sink to sucking Michael's dick ever again.

Sandy grabbed my arm and said "Go on cutie, you won't regret sucking Michael's dick." enthusiastically. I was lead over and pushed to my knees in front of him. I opened my mouth and let out a pleasured sigh as I could smell his dick, feel the warmth of it as I knelt inches from it, just as I was about to stick my tongue out and lick it, the curtain revealed someone else.

Sarah walked into the room and saw me on my knee's and giggled, "I leave you for five minutes and you've already got your eyes on a dick!" I got up, ashamed and went over to Sarah, I whispered in her ear that I wanted to leave and told her that this was the Michael I was venting my frustration's about earlier. Sarah looked at Michael, who was enjoying a blowjob from a different sissy and her usual smile turned into a stern face of disapproval for a moment, before a grin spread across her face.

She turned to me and whispered "I've got a plan, we're going home with him."

What?! I did NOT want to go back to their house and get forced to do any more humiliating things with those two. I shook my head in disagreement but Sarah grabbed me by the shoulders and said "Trust me cutie, I know what I'm doing." confidently.

She disarmed me in an instant, I paused and then nodded. Fine. Okay. But I didn't like this at all.

Sarah stood in front of Michael and with a single hand gesture, parted all of the sissies surrounding him and sat down next to him and signalled me to sit on the other side. The sissies dispersed and looked on longingly as the muttered among themselves. Sarah whispered in Michael's ear something I couldn't hear and he turned to me and grinned. Even up close he didn't recognise me apparently and I was relieved.

After a minute or so of trying to look sexy Michael turned to me and said "So you need breaking in do you?" and even though I could not think of a single thing I wanted less than his huge cock in me again, I nodded. I was putting a lot of faith in Sarah, but I knew I had to trust her.

We arrived back at my old house... it was daunting to say the least. I'd only been a way from it a day or so, but it felt like an eternity, Sarah's flat felt so warm and comforting, but my old home felt spartan, empty. Michael was visibly hard as Sarah and I entered the bedroom, he dropped his short and pulled off his tank top and grinned disgustingly as he removed his boxer shorts, revealing his hard cock in all it's glory. He grabbed it by the shaft and waved it in front of me. Sarah walked up to him and kissed him.

"Where are the drinks at?" Michael gave her brief directions to the kitchen and she disappeared and left me alone, he turned his gaze to me and smirked. "I love sissy ass, so tight and eager." he declared. I was not eager.

He walked up to me and effortlessly pulled me onto the bed. "Cute dress," he said as he caressed my legs, I was aroused and I didn't like it. He lifted the bottom of my dress to find my lingerie, he pinged the straps of my garter belt and pulled down my underwear. As much as I told myself I didn't want this, flashbacks to the time he fucked me and how good it felt were present in my mind. I felt him pouring lubricant on my hole as his finger eased into me.

"Mmmm, that's a nice tight sissy." he moaned as I felt his finger hit that special spot inside me. I moaned involuntarily, then covered my mouth. Where was Sarah?! What was she doing?

I felt Michael withdraw the finger and something larger was pushing against my hole. There was no guessing what it was. Sarah appeared at the door with a glass in her hand, she carefully placed it whilst stripping down to her lacy underwear, before picking the glass back up and climbing onto my back, so she was face to face with Michael and I was on all fours, supporting her. Michael began to fuck me and ugh, I hated it but it was amazing, his cock was just the right size and shape to make me cum effortlessly, I felt like I was trying to fight it to buy Sarah time to do whatever it was she was doing. Sarah kissed Michael hard and put the glass to his lips and he drank it all down as he picked up speed.