A Better Life through Chastity

"Are you looking forward to being my panty boy?"

I glanced up to see Sophie engrossed in the show, gasping as the second foul murder was unveiled. I looked down at my phone and typed, "Yes Sarah" and hit send.

After my tablet, I lay in bed, gazing at the ceiling. I was a slave to a co-worker, my life was changing before my eyes, tomorrow I'd have to wear female underwear to work and god knows what Sarah would want to do with me then. It was Sunday tomorrow, I only had to endure it one more day and then I'd be out of chastity. I didn't have work either but I still had to attend the course with Sarah. I was filled with dread.

Sunday morning came, and I awoke before Sophie, which was my plan. I grabbed the underwear from my bag, rushed into the bathroom and locked the door. As I showered, I noticed something I'd not noticed recently, I wasn't filling up as much of the cage as I did before. I used to easily fit to the end of it, now my dick seemed to only take up about 2/3rds. Was my dick getting smaller? Then a breeze sent me shivering, nope it was just cold, the window was open. I was being stupid.

After showering and drying, I took out the pink and white cotton underwear and slid them up my shaved legs. The sensation of the delicate fabric of the underwear against my smooth legs felt far more sexual than I had expected. I checked myself in the mirror, from the front it looked silly seeing the bulky chastity cage taking up space in the front. From behind, wow, my ass looked great. I'd never really admired it for what it was, but these underwear made it look so good.

I was actually getting aroused looking at myself, as vain as it sounds. Horniness was overtaking me again and I picked up my phone and snapped a picture of my ass and sent it to Sarah. The second I hit the send button I immediately regretted it, what was I doing, Sophie was asleep in the next room and I'm in here sending pictures of myself in girls underwear to someone from work. I got a response, it was a picture of Sarah, hard.

A following text said "Those look great on you <3, can't wait to see you in them up close," It was... kind of comforting to hear her say that, even if she paired it with a dick pic. I got dressed up and drove to work, the place was abandoned on Sunday, I was one of 5 cars in the car park.

I climbed up the stairs and into the conference room. Sarah was waiting, wearing a band t-shirt for some band I'd never heard of, her long hair was down and she was wearing cut off's and some black and purple thigh high socks. She looked... cute. Like an overgrown high school girl. She walked right up to me.

"How do they feel? I looved the photo you sent me, how thoughtful of you!" she was smiling a cheeky smile, like she knew I'd done it in the heat of the moment.

"Good." I replied, sheepishly. She chuckled with joy.

"Good! You're keeping them on until my training is over in a few days." Her voice changed from enthusiastic to stern mid-sentence.

I was uneasy with this idea, how long could I possibly hide wearing these from Sophie? We live in the same house, she would figure out sooner or later. Sarah was in high spirits, she got on her knees and unzipped me and I just stood there, letting it happen. She dropped my trousers and got a good look at the panties I was wearing.

"These are adorable, not my style but they definitely suit you. Very feminine." was her critical anaylsis.

I was both pleased and dismayed to hear that. She then continued to pull down the panties and look at my cage again.

"I never get tired of looking at this. Looks like someone needs a smaller cage though, you're a bit lacking to fit in this one, can't have any wiggle room, you need a nice tight cage to..."

I stood back and looked down... this was a heated room and I was still not filling up the cage? What was happening? I panicked and pulled up my panties. Sarah gave me a hug and said;

"It's okay to have a small dick cutie, it suits you to be honest I won't think anything less of you."

Her words cut right through me, how was my dick shrinking?! I told her it wasn't like this a few days ago. She smirked and said "Of coooourse, you've been magically shrinking your dick to impress me, right?."

Horror hit me as I remembered the tablets. That was it, I pulled up my trousers and said I had to go, Sarah shouted for me to wait but I was gone, back to my car.

I drove back to my house and opened the door to hear sounds of sex coming from the bedroom. I slowed down, two voices moaned in unison in our bedroom. I crept down the hallway and looked through a gap in the door and saw my girlfriend getting penetrated by a man with a gigantic dick. The man was holding her down and pounded her hard, her voice was practically squealing with pleasure. I was glued in place, hypnotised.

I felt betrayed, but I was also unbelievably turned on. I couldn't tear my eyes away from the couple, Sophie's soft, welcoming curves convulsing as this guys huge cock brought her to a screaming orgasm. I leaned against the door frame and continued watching as he picked up speed again and Sophie braced herself for round two. I looked longingly at the scene, when I slipped and pushed the door open with a loud creak. The two froze, Sophie looked up to see me watching. I didn't know what to say, my mind went blank. Then the large guy turned around and his face placed me.

"I know you, you're the clothes store panty boy!" I suddenly recognised the man as the same one who saw me testing underwear the other day. This was the worst thing I could imagine, I felt like I was going to die of shame.

Sophie giggled, "Oh so you're a panty boy now too? I didn't make you do that, you came up with that one on your own."

How was she so relaxed about this? I walked in on her cheating and now I'm the guilty one?! The man pulled his dick out of Sophie and I couldn't take my eyes off of it, slick with Sophie's juices, it swung around with each step he took towards me.

"Something catch your eye?" Sophie chuckled from the bed.

I tore my gaze away, I was so ashamed, he was fucking my girlfriend and I couldn't take my eyes off his cock.

"Get up panty boy," his husky voice commanded. I got up off the floor and stood in front of him, only coming up to about his shoulders. "Let's see them then." I knew what he meant, I didn't want to have to reveal to Sophie it was true but there was no hiding it, this guy looked like he could end me.

I reached down and pulled up my pink and white underwear so they could see them. Sophie broke out into giggling and the muscle bound hulk of a man before me said "I hear your locked up too, Sophie loves telling me about how you love to suck strap ons and get fucked in the ass. You sound pathetic, what's a goddess like her doing with a panty boy like you?".

I didn't know how to respond; I made her happy didn't I? Maybe not in the bedroom any more, but I tried? Sophie sat on the side of the bed and said "Oh yeah he loves sucking the strap on," she was digging this hole deeper for me and I had no way of getting out of it.

This entire situation was absolutely awful, I hated every second of it, but it was deeply arousing and I couldn't keep my focus off his 8-inch dick for more than a few seconds.

"I see, you know what happens to panty boys?" he said as my eyes reached the floor.

"No..." I said ashamedly, not really wanted to know the answer to this mystery.

"They become sissies. I love sissies, horny, tight little asses and best of all; they love cock." That exact moment I leaked another drip of pre-cum into my pink and white underwear, it was deeply humiliating, but worst of all he noticed my involuntary reaction.

"Since you can't keep your eye's away from my dick, it looks like you already love cock," he said. I averted my eyes immediately, but it was already too late, my sexual frustration had betrayed me. "Looks like you want to seal the deal on becoming a sissy." he said, grabbing his shaft and waving it in my direction. Sophie got off the bed onto the floor and walked crawled towards me, sitting next to me.

"Don't you want Michael's dick? Look at it, it's delicious," she grabbed my head and forced me to look directly at his hard, wet cock. It was glistening with my girlfriend's juices and I could see him waiting expectantly for me to serve it.

Sophie gently stroked my hair and whispered "Do it for me."

There were no thoughts in my mind, I had gone and my brain had taken a step back and let my subconscious take over. I felt a warm load hit the back of my throat and just like with Sarah, my head as held in place as I was forced to swallow. I was staring at a thick bush of pubes and a long, thick cock was being pulled from my mouth, I turned and Sophie kissed me.

The next few hours were torture. I sat in an armchair opposite Sophie and Michael, and listened as they spoke about how things were going to go down. Michael was moving into the main bedroom with Sophie, I would get the guest room. Chastity was not going to be unlocked for the foreseeable future as it displeased Michael. Sophie would be buying me more girl's underwear, and my male ones would be thrown out. I'd be referred to as "Sissy", until they found something more suitable. I'd make myself useful about the house and do the cooking, I'd also service either of them whenever it was needed. They were looking into a maids outfit for me too which sent shivers down my spine. I'd continue to go to work but my pay check would be used for them to buy toys for each other, Sophie would pull some strings at work to make it all possible.

Part of me found some of this incredibly hot, but the rest of me was filled with a hopeless despair, what would my life become? I'd be a slave. I don't have enough money to move out, I'd go straight to being homeless without Sophie's support, it was her house and I didn't know anyone I could stay with, so either I accepted a life of servitude or I'd go live on the street.

I was waiting for them to admit they were both joking, that this was some kind of practical joke or something, but as Michael gave Sophie a deep, slow kiss, her hand strayed down to the obvious bulge in his shorts and gave it an endearing rub... I could tell this wasn't going to stop anytime soon. As the two kissed for an awkward amount of time my phone vibrated in my pocket, I pulled it out to see Sarah sent me a text.

"What's up little dick? Why did you run out on me today, you don't want to make me sad!" said the text, there was a broken heart emoji next to her statement. I did feel bad for ditching her, but it reminded me why I rushed home.

"D-do I have to keep taking the tablets?" I asked. Michael rolled his eyes and let out sigh as he had to break away from Sophie so she could answer.

"You take them to reduce the size of your penis, sissy. So, of course you have to keep taking them." he explained, tired of talking to me already.

They did what!?

"You've already taken enough to drop an inch or so, Michael wants it down to a nub." Sophie stated, also seemingly annoyed that I interrupted them. I couldn't believe these words were coming out of sweet Sophie's mouth, the illusion shattered before me, she was not the Sophie I thought she was. I didn't know what to do, I was trapped at work, I was trapped at home, I couldn't move out or go anywhere else, this was hopeless.

Michael saw my despair.

"Come here." he said.

I hesitated, then got up and walked over to him, he grabbed my trousers and pulled them down to reveal the panties I was wearing and the chastity cage underneath, he slid down my polka dotted underwear and saw how little of the cage I filled up.

"Do we need to reduce it any more? He already couldn't please any woman with this pathetic thing." he stated eyeing up my dick.

Sophie nodded, "It's permanent anyway." she said.

Tears started rolling down my cheeks as the words sank in, I was stuck with a small, limp dick no bigger than 3 inches. What had I done to deserve this? Could this ever be reversed, was this my life now? Did Michael organise this whole thing from the start? He turned me around forcefully and pulled apart my ass cheeks, I didn't have the strength to stop him, I felt a wet finger probe into my ass, as hard as I tried to resist it, it was going in whether I liked it or not. I wriggled against it for a while until it hit that magic spot, pre-cum leaked out of me and I let out an involuntary moan.

"What a fucking slut." he said, as my cheeks went red with shame.

Sophie appeared in front of me and I looked into her eyes as she pulled me forward into her breasts, this was the closest I'd been to them in ages, whilst I was mesmerised, I felt Michael pull his finger out of me. I sighed in relief as Sophie stroked my hair and cuddled my head in her breasts. Suddenly something much larger was pushing it's way into my rear end, I tried to wriggle and fight it but Sophie held my head in place and shushed me as I felt Michael grab my hips as his big cock penetrated me. I let out sounds of distress as Sophie continued to repeat the lines "It's for your own good."

Michael's dick quickly reached spots in me I'd never felt stimulated before, the initial pain of taking his girth gave way to sensations brimming with pleasure. I curled my toes and grabbed Sophie's thighs and squeezed them, which was the only thing I could do besides moan helplessly into her tits. Pre-cum leaked out of me over and over adding more sensations to the over-stimulation I was experiencing. This wasn't like the strap on, this felt better, no wonder Sophie liked it so much. I tried to resist, part of me knew this was wrong and I shouldn't let this happen but all I could do was moan as his dick expertly pushed me over into orgasm. A steady stream of cum dripped down my leg and onto the hard wood floor as Michael pulled out and sprayed his own load over my back. Sophie giggled again and said "You'll like living like this, be a good sissy and you'll get this more often, you don't need to fight it."

The orgasm brought back clarity, what had happened to me? I've just been fucked by another man, I felt disgusted with myself, I didn't even try and resist it! I actually enjoyed it! I was so deeply confused by what I was feeling. Michael slapped my ass and told me to turn around. I faced him, his masculine features and steely glare bore into me.

"Kiss my cock." I really, really didn't want to, "Don't give me that pathetic look, kiss it." I was standing my ground on this one, it felt kind of pathetic to draw the line here when I'd already sucked it and let it fuck me, but I didn't want to sink any further. A feminine hand reached between my legs and squeezed my balls tightly, pain rushed through my body as I fell onto my hands and within inches of Michael's cock. "Kiss it bitch."

I looked back and saw Sophie smirking, "Go on, master is waiting." I turned again to face his cock as Sophie squeezed a little harder, through clenched teeth I gently planted a kiss on his semi-hard member.

"Good sissy, that's what you do every time I take the time to pleasure you, don't forget that." Sophie's grip was released and I collapsed on the floor into the little puddle of cum I'd created. Shame overwhelmed me, I was limp, humiliated, caged, covered in cum and laying on the floor with panties around my ankles. My girlfriend took pleasure in humiliating me and riding her lovers massive dick and I was getting blackmailed and feminised in my work place. How did this all happen? Why did this have to happen to me?

I was left to clean up the mess I'd made, wiping my sperm off the floor. My two tormentors watched TV like I used to with Sophie, their legs and arms intertwined. Dinner came and I was forced to serve them a bowl of curry each, as I sat in the kitchen eating a sandwich I made out of leftovers I found in the fridge. Eventually they went off to bed and I stood there, wearing nothing but the panties Sarah made me buy, quietly crying in the kitchen until I couldn't anymore. When the sadness wore off, I crept off to bed in the guest room.

The bed in there was a single, it was a small cramped room with just a wardrobe and a dresser, Sophie had never bothered to decorate it. I pulled up the covers and and lay there, alone, until I drifted off to sleep.

My dreams were plagued with feelings of confusing eroticism and despair, I was aroused and afraid until a sudden bang on the wall brought me up form my dreams. Sophie's pleasured screams pierced the darkness and I could hear the bed banging against the wall. I looked down at the outline of the chastity cage in my polka dotted panties and felt sad, I pulled them down and fiddled with the cage, trying to pull myself out but all I managed to do was hurt myself. My dick had shrunk and I couldn't even touch it, I couldn't seem to get it's attention either, with sex all around me, my little cock wouldn't get hard. I got on all fours and swayed my cage around trying to get a reaction out of it, the motion caused my bed to bang against the wall and the sounds of pleasure next door ceased abruptly. I panicked, what had I done? Footsteps approached the room and the door opened to reveal Michael's imposing silhouette looming in the doorway.

"Awake are we sissy boy?" He walked towards me, stark naked and his huge dick wavering around in the air, hard and ready for more of Sophie's pussy.

"I-i'm sorry I didn't mean to interrupt..." I said, weakly. It was embarrassing to be this weak in front of him, Sophie was my girlfriend!

"If you want to join in you only have to ask..." Michael's eyes moved down to my exposed cage.

"Oh, does sissy boy want out of his cage?" I knew I shouldn't have, I knew it wasn't going to work, but I nodded. Michael shouted to Sophie and he backed out of the room, Sophie appeared at the doorway and the two whispered to each other, Sophie was wearing practically nothing but the thong I bought her for her birthday, seeing her wear it for another man broke my heart.

She shushed me like you would a child and straddled me, I was stunned, what was she doing? She leaned down and I thought she was going to kiss me but suddenly she held my arms in place and then shifted her weight forwards, placing her knees on my arm and her pussy down on my face. I was trapped.

"Lick." she instructed from above me, I tried to pull my arms out but it was hopeless and kicking my legs was futile.

"Lick, sissy boy," hearing those words coming out of Sophie's mouth was again heart breaking, did she really think this was what I was? As upset as I was, the sexual frustration still had the biggest hold on me and being inches from Sophie's wet pussy was driving me insane, I didn't want to, but I started licking. I buried my tongue into her, knowing that just minutes before this Michael had been pounding her. She moaned loudly and I felt spurred on to lick harder.

"You know I tried so hard to keep myself from moaning when you ate me out in the past, you're really good at it," she giggled. I... I was good at it all along? "Your dick is too small to satisfy me but your tongue is excellent." I didn't know what to feel but all I could do was lick her. A few minutes of Sophie moaning and grinding herself against my face and I felt a pair of knees being pushed down on mine, was Michael trying to hold my legs down?

I wriggled but it was more hopeless now than before. I felt my cage being unlocked and I frantically tried to break free, but before I knew it I felt something lock around me again and suddenly my legs were free. Sophie sighed and climbed off of me, I looked down to see a smaller bulge in my pink undies. I pulled them down to see my clear cage had been removed, and I was now sporting a smaller, pink cage. I couldn't see my dick at all now. I looked at Sophie and she laughed as her arms were wrapped around Michael's side.