A Better Life through Chastity

I sat down in the disused conference room, under the dim yellow florescent lights and Sarah told me she knew exactly what I'd done to be assigned to her. So, maybe this would be as bad as I thought after all. She stated with a mocking grin and a patronising tone, that watching sissy porn was unacceptable work time behaviour. She winked at me and said "no matter how enticing it is," great, this was going to be hell.

She ran through a very basic list of acceptable internet ventures that anyone could tell was safe for work use, but wrapped it up quickly and gave me a sheet of paper with a brief questionnaire. This was intensely boring. Half way through the test she came over and sat down on the table, covering the test with her ass, her short skirt just covering the tops of her thighs that she placed either side of me. I looked up, confused, at her and she grinned widely at me.

"So how long have you been wearing a chastity cage huh?" I was shocked, how the hell did she know? Seeing my expression she continued;

"Oh so you ARE wearing one, lets see it." I backed up out of the chair and straight up refused, there was no way I was showing her it. She hit me with another shocker by stating;

"If you don't do exactly what I say, when I say it, then I'll tell the boss you're an irredeemable pervert, he'll fire you and then tell your girlfriend you like sissy porn."

I froze in my tracks, this was blackmail! Her grin grew wider as she waited. I had no choice. I unzipped my trousers and pulled out my chastity cage, flashing it quickly before putting it away. She squealed with elation and said it looked cute on me, she then began asking me questions about how long I'd been wearing it, and if my girlfriend made me wear it. I begrudgingly answered all the questions and whilst I hate to admit it, I was getting aroused by the conversation. When her questions were over, she said the next few days would be a lot of fun for us. Which only made me dread them more.

She opened her legs wider and told me to sit in front of her. I hesitantly sat down, Sarah's legs directly either side of me, when she lifted her skirt and revealed her sheer white underwear... with a big bulge in the front. My jaw dropped. She winked again and said in a sultry tone;

"It's okay to touch it you know."

I was mesmerised, this was just like the website except it was here, in front of me. I was fighting hours of sissy porn that encouraged me to just bury my face in her groin, I moved the chair back.

"Aww, don't you like? I thought this is what you wanted, you know you can't leave without my permission, I think you better get back over here and show me that you appreciate all I'm doing for you."

I was so conflicted, I wanted to, but didn't want to, had to, but couldn't. I knew this was something I'd have to do, if my girlfriend found out about this she would kick me out in a second, locked cock and all.

I looked up at Sarah.

"No one can ever know about this."

She nodded and smiled disturbingly. I reached out and ran my hand across the front of her panties, the bulge inside reacted and I withdrew, she sighed and grabbed my hand and put it back on her crotch, making me do circular motions. I could see she was enjoying this and it made it even worse, the bulge started to grow inside and before long I could tell it was ready for more.

She got off the desk and stood in front of me, holding up her skirt with both hands and instructed me to pull down her briefs. I couldn't believe I was doing this, this was wrong on so many levels. I grabbed the edges and pulled them down slowly, as her decently sized dick sprung out. It was bigger than mine was but only by a little, just looking at it made me deeply aroused. I felt horny but there was no reaction from my dick in the cage, I guess the tablets I'd been taking saw to that. Her erect dick twitched right in front of me. I'd never seen another dick up close before, let alone inches from my face, I could smell the aroma of it and that alone was driving me crazy. I wasn't gay, I'd never thought of dick before in this way, but I was overwhelmed. She could see my inner struggle and decided to tip things in her favour.

"You know you want to taste it, don't you. You've always wondered what it tastes like."

The suggestion was laid on heavy, just like the sissy porn videos, this hypnotic female voice was encouraging me to suck cock. I moved my face closer and her cute dick twitched in anticipation. My mind went blank in a haze of sexual euphoria, my cares slipped away as her warm girl dick entered my mouth. It tasted incredible. I licked it up and down and totally lost myself in the moment, it was like I was looking through frosted glass at what was happening. Her pleasured moans flooded my ears as I heard her say the same haunting words I'd hear the night before.

"There's a good cock sucker."

The words brought me back to reality, I was slobbering over this girl's dick, but before I could withdraw, her arms embraced my head and she convulsed. I knew what was happening but couldn't stop it, warm cum shot into my mouth and she held my head in place so I could do nothing but swallow what she gave me. Her throbbing dick unloaded deep into my throat, travelling straight down. When she finished, her grip loosened and she sat back down on the desk, my saliva dripping off her dick onto the questionnaire I'd been filling out, staining it. The taste was in my mouth, that salty taste I'd never forget. What had I done? What had just happened to me? My sanity was breaking through my sexual euphoria.

"That's a good boy, I can tell we're going to have a lot of fun together," she said softly as she stroked my cheek.

I felt violated, but I'd never been more aroused. She leaned down and gave me a long kiss on the lips that I helplessly fell into, I was unable to stop this captivating woman from having her way with me. Sarah tucked her girl dick back into her underwear and stood up, picked up the questionnaire and dropped it in the bin. Was it all meaningless? Did she ever plan any actual training? She sat down and told me I could have the rest of the day off as she smiled at me, picking up a clipboard and jotting some things down.

"Well, it looks like you'll be getting full marks for this," she said with a cheeky smile, her breathing still a bit rushed from the orgasm, "maybe we can see about getting your a promotion too!" she giggled.

The last part stood out on the drive home, if I did what she wanted, then maybe I could prove to Sophie I wasn't useless, if I could get a promotion at work she'd think I was at least hard working. But what I'd done haunted me, there was no denying... I pleasured a cock today. The depressing realism was that Sarah was the first person I'd manage to coax an orgasm out of, besides myself. I sat in the car for a few minutes thinking of how this week had changed me so, I'd never experienced any of this before this week. I knew the chastity cage was to blame for this. Internally I argued with myself over how it had made me a lesser man for the things I'd experienced, but I after what I'd just been through it was tough to say that I hadn't learnt how to pleasure a woman, just not my girlfriend.

When I got home the house smelt of cigarette smoke again. Sophie must have left the windows open again, I walked through the hallway and peeked into the bedroom, she was still in bed, naked now though. What a sight to behold her naked body was, even under the sheets I could visualise the contours of her perfect body. Then it dawned on me that she had probably been having fun with Mr. Cock whilst I was at work sucking off Sarah. Sophie hadn't noticed my presence, and I didn't want to talk to her after the day I had. She may have had ridden a dildo to climax but I had sperm in my stomach. I started to feel ill at the thought and went into the bathroom to brush my teeth, not that it helped.

I heard footsteps pass me and the front door close as I was bent over the sink. I put my toothbrush back and checked the hallway but didn't see Sophie anywhere, I walked up the bedroom and she was still in bed, when I realised she was sleeping soundly. Panic filled me, who had just been in the house? I started to rush around and check all the valuables and doors, but everything seemed to still be in place. I rushed into the bedroom and shook Sophie awake, she smiled when she saw me and looked up at the clock.

"You're home early again, was it a good day?"

I interrupted her to tell her I thought I'd heard someone in the house. Sophie's face dropped.

"Are you sure? I didn't hear anything." she claimed in a dismissive tone.

I was certain I heard something. I checked the bedroom but everything was locked up tight, even the windows. Sophie got out of bed and dressed up and watched me as I continued searching for anything out of place. I didn't get how she didn't believe me, it was her house and I'm the one who cares about burglars?! After several minutes of checking I couldn't find anything and said she would have to be more careful about leaving the front door unlocked if she was sleeping. I felt deeply vulnerable knowing that someone could just walk into our house in the middle of the day and, somehow, not be seen.

That night, I locked all the doors and we both sat on the sofa and watched a film together, I couldn't help but check behind me every now and then. I was paranoid for sure, I wasn't exactly strong and I doubt I could protect Sophie if someone broke in and challenged me, but what if it happened whilst I was asleep? Sophie spent most of the film trying to calm me down enough to get me to watch it. I took another tablet and stared off into space recalling the events of the day, it was wild when I thought about it, but it was so easy to dismiss my time with Sarah now I had even bigger things to worry about.

I tried to sleep but my brain wouldn't let recent events go. I turned to see Sophie sleeping soundly, not a care in the world. What if the burglar had raped her or something? All the worst case scenario's flooded my mind, which only fuelled more paranoia. Then my mind turned to what I'd done with Sarah. I'd agreed to the chastity cage so I could learn to satisfy Sophie, but all I'd done was let her down. I'd only reinforced how much better the dildo was than me, I'd got myself in trouble at work, then I went and straight up cheated on her by sucking a co-worker's dick. And here she was, still allowing me to sleep in her bed, unaware of what I'd been doing.

But what choice did I have? I'd rather she didn't know the stuff I did to try and make her happy than was told I'd been staring at sissy porn. I tried to deny it but I knew deep down I liked it, another wave of arousal hit me. I tried to lay in bed and close my eyes, but all I could think of was Sarah's dick and how great it tasted. I kept on trying to think of other things but it just kept on creeping back into my mind until I eventually drifted off to sleep.

I woke the next morning frustrated, but still no sign of anything from my dick in the cage. I was getting concerned.

"I told you this to begin with, they're only temporary. I'm disappointed you were silly enough to agree to take tablets without understanding even them, even from me." she explained.

She had a point. I'd done a lot of things I didn't want to recently. Still as long as it was temporary I was fine. I got dressed in a hurry and went to work, I was actually eager to get to work because of my overwhelming sexual frustration, last nights fantasies drove me to crave what Sarah was offering. As ashamed as I was to admit it... I wanted her dick.

When I arrived I went straight to the old conference room and sat down waiting for her to show up. Eventually she entered the room wearing a short black dress, her long legs exposed fishnet stockings underneath, she didn't look very professional, but she did look tantalising. I caught her eye and she smiled.

"There's my favourite cock sucker, what can we train you to do today?" I stayed quiet. "Let's get started then." she flicked on a projector, I sat and watched as she ran through more work examples of appropriate workplace behaviour, if there was ever someone who couldn't tell me how to act appropriately in the workplace, it was her. My eyes scanned her body for every move she made, staring at her round behind and her small but pert breasts. Images flooded my mind of her pounding me with her girl dick, me writhing in ecstasy.

Every now and then she would add a comment like "No masturbating" or "No sucking off your co-workers," like she knew she had that power to tell me what to do and I'd have to do it. I had no idea why she kept up the illusion of educating me on workplace behaviour, she knew I wasn't paying attention. She knew she had me right where she wanted me.

After a while she walked over slowly and sat on the desk, letting her pale legs dangle off the edge of the desk, her eyes looked down on me with the superior gaze of someone who knew she was in control.

"How are we feeling today? Is your poor dick getting frustrated?" she asked.

I nodded, ashamed to say it out loud. She twirled her legs around and once again I was facing between her legs. She lifted her skirt again to reveal she was already hard in her ruffled black underwear. This is what I wanted, my mind was a confusing fog of flashbacks from yesterday and sissy porn, my mouth dropped open. She knew I wanted it. I moved my hands toward her hard dick when she suddenly closed her legs.

"You already know how to do that, so lets train you to do something else first." It was a tease.

I was dismayed, and a little uncertain, what was she going to make me do? Sarah stood up and told me to take off my trousers. I looked around the conference room, the door was shut and the blinds were pulled. Getting up, I pulled down my trousers and revealed the bulge of my chastity device in my underwear.

"Boy underwear is so boring, but it looks like you've got some nice hairless legs at least." What was she talking about boy underwear being boring?

She got up, walked over to me and knelt in front of me, I'd be so hard if I could've achieved an erection. She pulled down my boxers and toyed with my cage, the sexual frustration was driving me crazy, I felt a twitch inside me as pre-cum dripped out of the cage directly in front of her. She giggled and scooped some off the cage with her finger.

"Well, well! Someone needs to learn to contain themselves." she chuckled. She scooped some off my cage and rubbed the sticky substance between her fingers, before holding them out and instructing me to lick. I gingerly bent down and licked my pre-cum off of her fingers. What the fuck was I doing? Why did I have to do this?

"Good boy." she said.

I stood up straight and felt hopelessly weak before her. Sarah told me she had an assignment for me. I was dreading this, I knew it wouldn't be good, whatever perverted thing she would come up with would probably cost me even more dignity than I had to spare. But I also felt like I wanted to please her.

"I want you to buy yourself some nice girly underwear, something cute that really accentuates your ass." a cheesy grin stretched across her face.

I was mortified, she wanted what?! I didn't want to do this, especially not buying it in public. What if someone knew me and saw me buying girls underwear?! My mind raced with irrational conclusions. Sarah could see my inner turmoil and smiled. She pushed me to my knees amidst my confusion and her dick was thrust into my face once again.

"If you want this, and I know you do, then you'll do this for me." I looked up at her, she was grinning again. She had me, if I didn't do what she wanted she would expose me, but if I did what she wanted I'd get that sweet girl cock I craved. I couldn't deny it, my desires spoke for me. I agreed. She got her phone out of her purse and commanded me to give her my number. I again, did what I was told and she sent me a mocking text that just said "good cock sucker." The humiliating tone she used on me only fuelled my frustration more. She told me we were done for the day, I was deeply disappointed nothing became of my time with her, but picked up my things and left.

I got a text on the way home that just said "I want you in panties for me tomorrow." I was dreading this. I wish I didn't have to do this.

I went to the most secluded area in town I could think of, to minimise the chance of bumping into anyone I knew. Sneaking into the clothing section like a first time shoplifter, my eyes darted around the room looking for people to avoid. Doing my best to dodge everyone, I breached the ladies underwear section and was overwhelmed with bikini bottoms, boy-shorts, briefs, thongs and a whole number of things I wouldn't fit into or look good in thanks to my chastity device. I couldn't believe I was considering aesthetics whilst looking at female underwear. I used to think about how badly I wanted to peel them off of girls from school, but here I am trying to find a pair to wear for a girl. Sigh.

It hit me really fast that I didn't know my size, ladies underwear had numbers rather than names like large or medium. I was stuck. I couldn't go trying them on, so I looked around and started holding the pairs to my waist to see if they matched. Most of them were either too small or weren't designed to accommodate what wasn't meant to be there, some of them just weren't cute either, I didn't want to know the consequences of not pleasing Sarah's personal tastes.

A few minutes past and I found myself holding up a pink and white polka dotted set of panties that looked about the right size, when out of nowhere a deep voice said "what are you doing?".

A tall muscular man, was looking at me from across the section, he was holding a pair of trainers and looked like he was on his way to try them on when he saw me holding female underwear up to my waist for size comparison. Flustered, I kept the pair I had and fled the scene. Luckily the assistant behind the cash machine didn't care what I was doing whatsoever, which avoided yet another awkward conversation and I all but ran out of the store to my car. My heart was pounding. I put the underwear under my seat and gripped the steering wheel tightly.

Still breathing heavily, I sent Sarah a text saying I got a pair and she replied "Good boy." and sent me a picture of her hard dick, which set me off again. All I could think about on the drive home was the underwear I just bought and Sarah's delicious cock. I pulled up outside my home, stuffed the underwear into my bag and walked into the house. No smell of cigarettes today; guess she was as paranoid as I was.

My thoughts were torn away by the intruder yesterday. I'd forgotten. I thought about going to the police about the matter but what could I say? I heard a noise, they took nothing and no one saw them. There was nothing to go on, they'd charge me for wasting police time. Sophie was on the sofa drinking some cocoa, she turned to me and smiled after seeing me enter.

"There he is," she knew how to make me feel welcome, like I was something special after all, even after all the things I'd done to let her down, she still loved me.

I sat down next to her and gave her a long embrace, she was watching some crime drama on TV, so I sat with her. I was still a little horny but it wore off as we both joked about the drama she had on, I'd point to someone on the screen and insist they were the killer and Sophie would laugh and explain why it couldn't be them. She laughed a lot, but always took my jokes quite seriously, she thought I was silly. I loved her, but deep down I knew I'd failed her even more so than she thought. As we joked, my phone buzzed in my pocket and I withdrew it to see a message from Sarah, it read;