A Better Life through Chastity

I wrapped my arms around Sophie and squeezed her tight as I shot my load inside her. She was perfect; large breasts a peachy rear all in a pale curvy frame, her long brown hair framed her big welcoming eyes gleamed up at me. I didn't deserve her. I sighed heavily and sank into her as she smiled and gently stroked my hair.

I had failed her again, I knew it, but she never said anything she just smiled and said, "I love you."

She never moaned when we made love and just seemed to tolerate the experience, but maybe that's just how she was. I was trying my hardest but she just never seemed like she enjoyed it. Sure she kissed me and embraced me in a way that said, "You tried." I loved her with all my heart but it was painful to feel so useless to pleasure her, rolling off her and onto the bed beside her, I gazed into her big brown eyes. Her addicting smile entranced me and I couldn't help but return it.

"Did you enjoy that?" I asked. Sophie silently nodded like she always did, maybe I was paranoid, everyone is different, maybe this is what sex is like for her? Her comforting behaviour made me forget all about it as I gave her a hug and went off to sleep.

The next morning was nothing out of the ordinary, it was Sunday and she had the following week off.

"So, it's a whole week off! What do you have planned?" I asked enthusiastically.

"Hmm, I dunno! I'll have to make it up as I go along," She replied with a giggle.

"Well, don't over-do it, all that sitting around and you'll never want to go back to work!" I teased.

She rolled her eyes, which gave me an opportunity to go in for a kiss.

I had to lean up to kiss her, she was quite a few inches taller than me which I always found a little intimidating and sometimes others would make jokes, but she never made any comments about it herself, so it was easy to just ignore them.

After a dreamy drive into work on a crisp Sunday morning, I found myself thinking about the previous night as I sat at my desk. Sundays were incredibly lax, so I spent the afternoon daydreaming thoughts of ways to make Sophie moan. Maybe she would like kinkier stuff? But it wasn't something she'd ever mentioned, and I didn't know anything about kinky stuff, so... maybe not. I wanted to please her. No guy wants his girlfriend to be dissatisfied with him. I didn't take long before my lewd thoughts caused a stirring down below. Thinking about it, I didn't have the biggest cock in the world, it suited my size though, it looked natural to me. Maybe it's considered small, but Sophie would always put on a big smile when she saw it, so I always figured she at least was impressed. Eventually the stirring I felt eased as work dragged on. I didn't have any time to relieve myself and instead I went home to my beautiful girlfriend and the house she owned.

I opened the front door and shouted to her, but there wasn't a reply for a few seconds. I walked into the bedroom and found her buttoning up her shirt, the room smelt of cigarettes and I reeled at the smell.

"The neighbours been at it again?" I asked. Sophie sighed and nodded, the smell must have come in through the window. Our neighbours would just smoke outside and the smells wafted in. I gave her a hug and it was difficult not to let my face get pressed into her breasts from her embrace, though she was guaranteed to make her giggle. The moment was soured by the smell of the smoke, it was off-putting, and despite her cleavage being as bountiful as it was, they were hard to enjoy at the moment.

We sat down to dinner in front of the TV, some random show we threw on whilst I ate was playing as background noise. She seemed calm and contented and I was hesitant to ask her how she felt about sex with me, but it was driving me nuts to be honest. Then she looked up and saw my furrowed brow and decided to ask me what was wrong. I couldn't hide anything from her, she knew I melted when I was in her presence. I had to ask.

"...Are you... Satisfied with me? Like, in the bedroom? Do I do okay?" Sophie's face perked up and her big smile returned.

"I love you how you are, what are you worried about?" she queried.

"I just get the feeling that I'm not doing it for you, like, is there something I'm doing wrong?" I shamefully asked.

Sophie was the best thing in my life, without her I'd not be living in this house, she made the majority of the income, being a major player in pharmacist groups, heading up her own company, she was so successful and me? I felt like a leech on her sometimes. The least I could offer her was some sexual satisfaction. Her face smirked a little, she was feeling frisky, I could tell.

"I've been waiting to hear that from you."

I was stunned. I HAD been disappointing her? She wanted me to admit it to her? I felt anxious.

"It's okay sweetie, I've got some ideas, I've been online looking up solutions since last time you were inside me and now I'm certain you're ready to try them," she explained with delight.

I was filled with a little bit of hope, but a staggering amount of shame was looming over me, I really wasn't prepared for her to practically admit that I'd been under-performing. I know I asked for it, but I was hoping she'd let me down gently at least. I mean, she was always pretty blunt but this was a sensitive subject for me.

She put her bowl down and got up, signalling for me to come into the bedroom. I nervously got up and followed. I found her rummaging through the cupboard where she produced a box. It was a sex toy, it had to be. Was she really resorting to sex toys to make our sex life better? I wouldn't call myself proud but using sex toys just to make her orgasm felt like I was cheating. Pictures of cock rings and other weird contraptions filled my mind, I didn't know much about sex toys to be honest I was pretty plain I guess. She revealed a palm-sized black velvet bag that was neatly tied up with a little red string. She untied it and removed the bag to reveal a clear, hollow, penis shaped device. It looked fairly small in her hands, it wasn't immediately apparent to me how this would help.

"This is a chastity device," she said, still smiling, holding it out in one hand, "you're going to wear this for me and we're going to work on your other skills." I didn't understand, how was that going to help? It looked like some form of punishment.

"What? I've got to wear that?! It's tiny!" I blurted out. Sophie walked towards me and knelt in front of me, I almost started backing up but her enchanting eyes just kept me in place as she unzipped me, and put the chastity device next to my exposed cock.

"See, it's not that tiny once you compare it to your little guy here." she said seductively.

"Little guy?" I thought, oof, that hurt, maybe she did think I had a small dick. I didn't like where this was going.

"If you wear this for me, I'll go down on you once a week."

I'm sure for other couples this didn't seem like a great deal but Sophie never performed oral on me so this deal was starting to sound sweeter.

"And you can work on going down on me," she said in a sultry tone, one of her hands reaching down to trace her groin through her jeans. I was powerless to resist, she was getting me going and the deal wasn't too bad from my perspective, more blowjobs? How could I say no?

"...Well okay I guess," Sophie beamed at me and put the chastity device down on the floor and took my cock in her mouth. My god, it was incredible, the first blowjob she ever gave me nearly floored me. This was definitely something she had done before, keeping her hidden skills locked away for a special occasion, I felt honoured to be receiving it. Her juicy lips worked my cock to the point where I nearly had to beg her to stop, and pretty soon after starting, I came. I felt a little ashamed but she was so damn good. I hugged her head.

"Holy shit Soph, that was incredible," I said struggling to get the words out. As I recovered, she smiled up at and me and picked the chastity device back up.

"So are you ready for your part of the deal?" she asked, tilting her head to one side and revealing the wicked grin she only unveiled when she was horny.

I was hesitant, but if I got to experience another blowjob like that, then I was certain the device could at least be tolerated. Upon my agreement, she smirked briefly before expertly disassembling the device, like an army vet dismantling a gun, and had it in pieces ready for my encasement. After rubbing some oils into my groin area, she assembled the device around me and gave me a quick glance as she clicked the lock shut. My cock totally sealed within in the device and I watched as she took both the keys for the lock and slipped them into her purse. It was then that it dawned on me that I wouldn't be doing any playing until she took it off me in a week's time. I tapped the cage but felt nothing but faint vibrations, it was odd.

"There's more," she said, standing up in front of me.

I looked puzzled, but figured out where it was going when she pushed me to my knees and giggled. I was staring into her groin as she unzipped her jeans and dropped them, her velvety yellow underwear and thick pale thighs were inches away from my face, I could smell her scent and it was irresistible. She peeled off her underwear and pulled my head straight into her groin, the intoxicating smell was sending waves through me as I opened my mouth to lick her pussy. I was starting to get hard in my little clear prison, and I wanted to play again already, but all I could do was rock the cage back and forth with one hand.

She looked down at me and continued her loving smile as I tried to eat her out, this wasn't something I was good at and we both knew it. She parted her legs so I could push my tongue into her deeper, it was pretty hot to be doing this to her as she stood up, her height always secretly aroused me. I tried to catch her face and see if I was making an impact, but her breasts obscured her expression. She was oddly quiet and I was starting to feel like this wasn't giving her the desired effect either. Through frustration I tried harder, licking faster and running my hands up and down her thighs and squeezing her soft, peachy behind. But after a few minutes, she pulled my head out from between her legs and I watched her pussy disappear behind the yellow barricade of her underwear. I felt defeated. She smiled down at me and got down onto her knees with me and gave me a hug.

"Well, that was a good try sweetie, but we'll have to improve your skills." Again, a faint flicker of hope that I could do better with practise was in my mind, but still, I felt guilty that once again I had failed to give her what she wanted.

I was hoping that Sophie would let me out the device when I went to bed but she quickly stated that it would be easier if I just stayed in it overnight. I wasn't pleased about this, but I wasn't about to jeopardise any future blowjobs I may receive, so I kept it on.

The next day I awoke to pain in my groin as morning wood was causing serious interference with the chastity device. I nudged Sophie awake and asked if I could take it off for a bit.

"Oh I hope you aren't planning on backing out of this just after we started," She said, laying the guilt was on thick. She didn't need to say no, it was a given.

After that crushing defeat, I tried to think calming thoughts to ease the situation. But as if to tease me Sophie climbed out of bed in front of me, freeing herself from her nightwear and her glorious naked body was bending and positioning itself in irresistible ways. The strain my dick was causing in the device was unreal, I wanted to be inside her so bad, she gave me a wink and walked out the door to the shower, she knew what she was doing.

Thanks to Sophie's display, focusing at work was somewhat difficult. The chastity device did nothing but remind me of it's presence, which caused me to get hard, which made it impossible to forget I was wearing the chastity device. It was a vicious circle. I barely got anything done and the thought of the blowjob I received just made things worse. I rushed out of work and drove home, turning the car radio up as if it would somehow drown out my own thoughts, when Sophie greeted me in a low cut top her breasts were practically trying to escape from. She eagerly asked me how I was finding the chastity cage and I was at a loss for words, I knew she was trying to help me with it and I owed her a lot, but the cage was making it difficult to focus. So I just smiled and said I was getting used to it. She smiled back gleefully and said she "knew I would like it" which felt ominous.

I wasn't sure how much more of this I could take, but to not even make it past the first week would make me seem like I wasn't trying. On the way past the bedroom the smell of smoke drew my attention to the bed, which was unmade. I guess Sophie really had been trying not to work too hard, glad she was at least enjoying herself. I made the bed and closed the window, and after a while the smell faded.

To pass time, I ended up surfing the internet, looking up things on eBay and generally trying to keep my mind off of my dilemma. I'd gotten into collecting movies, usually old action films and the occasional sci-fi thriller, those were my jam. Sophie's income covered pretty much all our expenses, so I was free to spend mine on whatever I wanted. Though even when I was doing something interesting, the constant feeling of the device kept on interfering with my thoughts, and whether I liked it or not, my mind was unwillingly dragged back to thinking about the chastity cage, Sophie's pussy and how badly I wanted one but not the other. I decided to do a little homework and ran a search on "chastity". I found a lot of guys wearing chastity devices and some... girls? I was surprised to see people wearing dresses, pink lace, black lingerie and seductive clothes all with the familiar chastity device poking out amongst all the frills and satin.

What? I clicked on a link and the page was awash with pink-clad girls with dicks, wearing make-up with chastity devices locked onto them. The word "SISSY" mentioned again and again. These weren't girls, these were boys who had become sissies! The page was hypnotic; black and white swirls filled the corners of the web page with "Suck Cock" messages flashing up every few seconds. My cock strained in its cage and I gave the device a longing rub. Then I snapped out of it, what the hell was I doing? I closed the page and turned off the PC.

We sat down to dinner again but this time Sophie laid her leg right across my lap.

"I think it's so hot you're wearing it for me, you're such a great guy," I couldn't help but feel a little proud of that, like, maybe other guys wouldn't make an effort like this? I'm trying to make an active change in my life, she's unsatisfied and I'm going to change that. She put down her bowl again and spread her legs, sliding up the skirt she was wearing, this time a black lacy pair of underwear greeted me, like the ones I'd seen online earlier.

"Want to try again?" she said seductively.

I put my bowl down and got on my knees, sliding my head between her thighs to breath in her gorgeous aroma, sending out my tongue to greet her tender pussy with a lick. She was already wet, clearly wearing this cage for her was turning her on endlessly, maybe it wasn't all bad then. I slid my tongue up her slit and dug it into her, licking what I thought was her clit and doing everything I could think of to make this enjoyable for her. Five minutes of furious licking passed, my jaw was aching and I saw her sort of drift off and look at the TV screen, I was disheartened. Was I really not making any impact on her again? I was trying so hard! She gently pulled my head away, slid up her lacy underwear and closed her legs.

"You've still got a lot to learn honey," she said, her look of disappointment changed into encouragement.

No matter what she said, I was really upset by this.

"I think you need more practise, I don't want to tell you how to do it, I know you're trying but you need to figure this out for yourself," she said.

I was so sure I had it this time, I have to be doing something wrong, how hard could it be? I'd seen people in porno's do it loads of times.

We went to bed, and the next day I awoke to the same pain from the chastity device.

"Still giving you trouble huh?" she asked, looking down at my straining dick.

"Yeah, this is pretty painful, is this ever going to stop?" I questioned, this was her idea after all, blowjob or not, I wasn't eager on tolerating pain every single morning.

"I'll put a call in to the guys at the company and see if we can get you something to ease the problem," we both stared at my cock pressed against the clear plastic innards of the cage, trying to break free. Sophie leaned down and kissed the cage and winked.

"You're in this for the long run, got to make it comfortable at least," she added.

Long run? She must be joking.

Another day of sexual frustration at work awaited me, I daydreamed more about how to please Sophie whilst that web page kept cropping up in my mind. I found myself searching for that same page on my phone during break, and stared at the flashing images some more. It was oddly captivating, seeing the girls all dolled up with their cute chastity devices on display... uh... I better close the browser app and stop looking it up... it can't be doing me any good.

When I got home the smell of smoke permeated the bedroom again; it was getting tiring. I closed the window again and sprayed some air freshener around the place. I pulled out the computer chair and made myself comfortable to do some more browsing, when Sophie crept up behind me and grabbed my ribs gently, scaring me. She giggled her frankly adorable giggle, and thanks to a tight tank top, her breasts jiggled as she laughed at my reaction. She told me she had a gift for me. I was hoping it wasn't anything like the last gift that encased my cock, but I got up and followed her to the hallway where she presented me with another sex toy, this time it was something more standard; a pretty decently sized black dildo.

I didn't think I'd ever be standing in front of my girlfriend waving a dildo, but here I was. She couldn't contain her laughter and said it wasn't a dildo, it was a "sexual aid device", but I wasn't finding it so funny. I felt like I'd just been replaced by a hunk of silicone. It was bigger than I was for sure.

She smiled and said she would need to use it until I learnt how to satisfy her with my tongue. I felt kind of humiliated, but also confused, how was this a gift for me. She read my puzzled face.

"If you find Mr. Cage a little too frustrating, Mr. Cock here can take care of that for you," she explained slowly. There was no way! She was joking, surely?! She couldn't keep a straight face and started laughing.

I tried to laugh, but it just wasn't that funny to me. She gave me a comforting hug, apologising to me, saying it was only a joke. Good.

Her true kinky self was revealing itself to me and I felt like I was falling behind in all this stuff, chastity cages and dildos? What the fuck? She never told me she was into any of this stuff. Maybe I was too plain for her as well, all these feelings of inadequacy started to surface, but the hug made it all go away. She melted my worries away, but soon caused other problems as her breasts once again were pushed up near my face. I tried to stay calm, but the combination of her perfume and her large tits were too much for me, I smiled during the hug, but the straining in my cage made the moment hard to enjoy.

That night we cuddled up together whilst we ate, she was very sweet to me the whole time, and as soft as it sounds, these moments of respite were island paradises in the sea of sexual frustration that was everything else that happened today. My worries boiled away.