Editor's Note: This was posted by doublingdowns, a Reddit user, to a sub that I created and used to maintain before I got kicked off the site for the 150th time. I liked the story so much that I asked him for permission to repost it here, which he graciously granted. Give him some good feedback and maybe he'll become a regular author here! - dig420

While I’ve got the fire going in me from the last post I’m going to give two of my most memorable times that my girlfriend Jenny at the time cucked me.

The first time corresponds after her finding my trove of degenerate porn on my computer, about a day or two later after the initial events my chastity device showed up and Jen seemed too excited to be putting it on me.

She was always super sexual and twisted in her ways so she first had me lay down on the bed and began to spit on my cock and start stroking it, she began saying how much fun it was going to be for her to be in complete control of my orgasms and how hot she was going to feel owning the key to 'me' in her hand or around her neck. Obviously by this point I’m rock hard after not having cum for three of the most intensely hot twisted days of my life. I had a massive foot fetish in with my other kinks and in the past days since she had found what really made me tick through finding my porn she began to really home in on what got me off but helped her maintain dominance.

Foot worship had become a huge thing. Every time she’d leave the room and came back she’d make me clean her feet and jam them in my mouth making me gag. Jen had lovely tanned skin like I mentioned previously which ran all the way over the top of her feet leaving a perfect pale pink sole comparison half way down her foot. She always painted her toe nails and in the past few months I had given her plenty of lotion foot rubs so they were always pristine looking and soft.

So right there and then with my cock pulsating in her hand she asks if I’ll do anything to and for her and her feet no matter what and I answer yes to which she puts a foot to my face and I begin to suck on her toes.

She then asks if I give myself to her to own, with what I can only call an animalistic look of lust in her eyes, the air was thick with a humidity of lust and craving, I couldn’t help but nearly explode as I said “Yes!!!”

With that she simply says “Good little boy, don’t forget you’re not allowed to come ever again until I say so!”

At this point I’m doing everything including biting my lip hard to stop my self from busting and she knows this, right there and then she was trying her best to get me to cum to punish me in some way I couldn’t even begin to imagine.

She abruptly stops and tells me that as I’ve been so good that she was gonna let me in on a little secret in her seductive sly voice, again at this point my heart tied itself up in a knot and my stomach awoke with dread but that had all become part of my degenerate ways with Jenny now and the feelings all stirred into a fiery hot flash of intense lust, passion and a yearning for more of this depraved sexual path.

She got up on the bed and put her leg over me and ever so slightly brought my cock up to her molten hot wet cunt and started sliding it against her wet throbbing clit and drenched pussy. The mix of my pre cum and her juices felt like a live connection being formed. Every single millimetre she would slide against the swollen head of my cock felt like nirvana, bliss... in that moment it’s hard to describe. I’ve never wanted to live a feeling for the rest of my life like I did in that moment of unbeknownst perversion.

She started to slow down her rhythm and made direct eye contact with me. She pulled up her top to show her pretty perky tits and raised my hand up on to one, with this my cock twitched uncontrollably to which she stopped and told me “If you cum, I will make you regret it! Especially before my big secret reveal and you’re going to want to hear it.“

She slowly lowered her body on top of me while maintaining the contact between my cock and her clit and begins to tell me how her and Mark would watch tv together quite a bit and how they’d always snuggle up together in bed, she said she never really found mark that attractive but she knew he wanted her.

When me and Jenny had started dating I noticed mark seemed off with me but I knew as a guy thing he was probably jealous/ a bit gutted he’d lost a girl he was in to. To my astonishment though Jenny began to tell me how Mark had started making extra effort and attempts at trying to get her to do something with him and how he didn’t like me at all and thought I didn’t deserve a girl like her even going as far to say that if I hurt her at all he’d physically assault me for it.

Jenny continued to tell me details with a huge sexy smile on her face, she could feel my cock basically vibrating against her clit with every humiliating detail she told me. “When we’ve been watching stuff together he’s been coming down with no underwear and really loose shorts, I didn’t expect it but he’s got a huge cock! I accidentally brushed against it once or twice with my perfect feet you love so much, speaking of which I don’t think you’re the only one with a thing for my feet, maybe they’re not all yours after all!”

My world was spinning in ecstasy, it was like I’d asked for a shot of perversity and ended up with a barrel of depravity. “Tonight he’s going to be down in my room with me watching our programs, and I might end up getting sore feet and asking him for a massage. How would you like that for me? Your girl getting another man’s hands rubbed all over her sexy body?”

I’d never wanted to tell someone I’d loved them so much as I did right there but I was so lost in the lust I continued leading my beautiful girl down a path of depraved debauchery.

“What does he get to rub?“ I asked.

“Anything he wants!“ she said getting close to cumming.

“What if he wants to do something more?“ I asked with a stirring feeling in my stomach, letting me know I was hoping the answer was going to be as twisted as I secretly wanted.

“Ohhhh I don’t know, his dicks so much bigger than yours I might have to thank him in some way for massaging me, don’t you think?“

All I could muster was “Oh baby you don’t need my permission to do what you want.“

This sentence pushed Jenny over the edge and she found her self in one of the most powerful orgasms I’d ever seen her have. I had to do everything within my power to stop my dick rubbing against her pussy and spraying my load everywhere.

With Jenny laying beside me we talked for a while and shared excitement for the wild ride ahead, mainly starting from the night ahead of us. After a while we got up and she said she’d be going for a shower if I wanted to join, which I liked the sound of until she said that first we had to put my cage on. I remember feeling a realisation of how real this all was, but with me being at a all time horny high and it not looking like I was getting release soon I waved any resistance to her putting me in a cage but I knew it would be frustrating adjustment.

As she locked the cage up and added the key to her charm bracelet she had a look of lust again immediately and began to suck the solid plastic casing that know encased my cock. Through the slits I could feel small leeway’s of her tongue run across my cock but with a hard wall pressing against my dick from all angles pleasure and discomfort were all mixed into one again hitting me with a wave of humiliation stirring a feeling of sexual ecstasy.

With that Jen stood up and bent over the bed and asked me to attempt to put my caged cock into her. She was so wet that it gave little to no resistance and slid in, she began to mock me saying that it was the hardest my dick has ever felt and how it’s the best it’s felt because the cage gave it some girth, all the while she was saying this she never ever kept very quiet and there were times that the extra humiliation from that would make me feel like I was about to explode from the torrents of abuse.

After pushing me off and giving me a sly wink she grabbed my by caged cock and dragged me to the shower which wasn’t far from my room but far enough that people could have seen me and we showered together. Thankfully on this occasion nobody seen me as Jen made me walk back to my room naked with my caged cock.

When we got back to my room Jen popped down stairs to grab some clothes to bring back to my room, when she came back in she put out three outfits and said that I’d have to choose which one she wore while down stairs with Mark that night. I ended up choosing the third outfit which consisted of a low cut t shirt which had been cut so the whole stomach was showing with some under boob on display and a pair of loose fitting lounge shorts. This wasn’t the sluttiest outfit of the three but it was inviting enough without it being painfully obvious, after asking Jen to try on the outfit I asked her to lay down on the bed, imagining what position she may be laying in later that night when Mark and her are watching stuff and surely enough the loose fitting shorts did nothing to cover her perfect pussy when she was laying down.

If she was going to ask Mark for a massage tonight then there was no way he was leaving without doing something hot and sexual with my girlfriend and at the very minimum he’s going to see her wet pussy and tight little asshole.

After this Jen went and put on a little bit of make up and came back sat next to me and looked me again in the eye and said “Tonight’s going to be so hot, you’re gonna wait here for me like a good boy while I’m downstairs doing whatever I want, I’ll text you if I feel like it. Keep the door unlocked and maybe I’ll see you later.”

With that Jenny headed off downstairs leaving me in a world of pure sexual imagination. No matter what I did I could not focus on for the life of me, knowing that my girlfriend was dressed in practically nothing down stairs in a bed with a guy I now knew didn’t like me and wanted to fuck my girl.

It had been about three hours since she had left when I got a text on my phone. It was from Jen and my heart felt like it hit the floor and back up I was so excited/anxious. It said “Come get your power bank from my room. Say you need it.” I was a bit confused but I could only wonder what was going on so I chucked some clothes on and tried my best to hide the fact I was now wearing a chastity device on my cock.

As I got to Jens door I did something I hadn’t done since I’d moved in, I knocked the door to my girlfriends room. This alone sent a hot flash of raging sexual fire through my body wondering what I’d walk into when I heard Jens moaned “Come in”.

As I opened the door it felt like an eternity for the handle to go all the way down and for the door to open, as my eyes scoured left towards my girlfriends bed though I felt a euphoric feeling of sexual pleasure as I feasted my eyes on the sight of mark sitting at the back of Jen running his hands up and down her shiny oiled up legs from the tips of her toes to the bottoms of her ass cheeks.

I felt like I was a deer caught in headlights as it took every fibre in my body to continue my reason for coming in there. I tremblingly muttered out “Suh-sorry I needed my power bank.“

Jen quickly retorted with “You really needed to come down for that now? When we’re watching our shows? You’re just being paranoid and checking on us aren’t you!?"

I could see Mark laughing at my humiliation but he didn’t divert his eyes away from the sight of my Jenny’s perfect feet legs and most of all her guaranteed soaking wet pussy on full display.

In that moment I could clearly see that Mark was indeed wearing a loose pair of shorts like Jen had told me and with his groin so close to Jen’s feet I could only imagine what I’d missed or was going to miss but it made me feel like I could have fainted in ecstasy there and then.

I was quickly brought back to earth by Jen snapping “Is there another useless thing you need or can you leave now?“ as I looked at her I could see a devilish smile creeping along her face and a dominant look in her eye, her setting me up to humiliate me was one of her favourite kinks and she did it so well.

“Sorry I didn’t mean to disturb your show.“ I said losing any chance of feeling like a man, as I proceeded to leave I kept my eyes sharply at a angle where I was looking at Jen’s perfect legs and on my last steps out there it was! Jen was no liar. Mark did have a much bigger cock and there it was cradled in between my beautiful girlfriends perfect feet, it must have rung the length of her feet easily. Something which not so long ago I’d claimed to be mine and only mine but now there was my girlfriend letting another guy fuck her feet while he rubbed his hands all over her legs and ass.

Before I’d even left a room Jen began to talk about me as if I weren’t there exclaiming “He’s such a fucking weirdo sometimes, it make me wonder why I’m with him!” With that Mark ran his hands up Jen’s legs and started moving his hands to the insides of her thighs in which she let out a slow moan and that was all I seen while making my way out of the room as slowly as possible.

Getting back up stairs to my room I wanted nothing more than to beat my cock senseless, looking at this cage on my cock made me want to find a way to get it off there and then but again the intensity of knowing A. What Jen would do if she found I tampered with it B. The intensity of how hot and sexual I found it to be treated this way by someone I cared about, made it not worth it.

The only thing I could do was sit and wait for my Jen to come back up when she was done doing whatever she wanted to do, it felt like I waited for a eternity. I tumbled between a million and one graphic depraved thoughts of what they could be doing, half the time I didn’t know if I was imagining what I wanted her to do or what I simply by this point expected her to have done.

It was 12:13 when I heard the sound of high heels walking towards my door which I found strange. As the door opened and in stepped Jen I looked her from foot to head and immediately noticed wet lines running all over her feet and down her legs, she’s looking back at me with the most sexy smile and heads over and lies down on my bed.

At this point I’m in awe just looking at Jen laying on my bed with what I can only imagine is cum from another guy on her as it spills down her soft legs and thighs onto my bed sheets and she softly begins to tell me how much fun her and Mark had after I’d come into the room to be humiliated by her.

I’m enticed by her every word so I’m sitting attentively awaiting more and she begins to tell me how after I left Mark started a acting like she was his, how his hands started to get more adventurous and how other than just leaving his dick sit on her feet he started to fuck them. Jen started saying “We started belittling you and talking shit about you. I told Mark to tell me what he’d to do you if I wanted him to beat you up. He started saying how he’d beat the life out of you and piss on you and leave you on the street in shit. The darker he got, the more I liked it. You were just a piece of shit to us down there and it got me so horny, Mark slipped his fingers into me and I begged him to keep talking about you and it got me off ! Hearing how pathetic others think you are got me off! Then without warning mark just came everywhere all over my pussy and It felt amazing feeling his hot cum run down my pussy knowing you my little wimp was sitting up stairs waiting for me.“

As Jenny continued with each sentence her voice got darker and more dominant “Just as I thought we were done Mark asked me to let him cum again, but this time he wanted me in those sexy black fuck me heels you bought me, the ones you’ve yet to fuck me in as we were saving it for a special night out, we’ll I thought what was more special than this. He begged to put it in my pussy but I made him fuck my thighs and rub his cock along my cunt and cum over my feet and my high heels instead.“

As I looked my sexy girlfriend up and down I started noticing every single drop of cum that plastered the lower half of her body, I pulled aside her shorts to see her juices and Marks thick ropes of cum mixed together. Seeing how it had run down her legs and pooled into her heels along with his second load sent me into overdrive.

Jenny knew by my silence and the sight of my eyes trailing down her legs that I wanted to clean her, by now she was learning that there wasn’t much I wouldn’t do for her. She said in a stern voice “ I’ll let you clean every part of me that’s covered in cum if you’ll do this every time I fuck someone from now on!”

I barely said “ yes ” before she commanded that I start addressing her as mistress to which I corrected my self to “yes mistress.“ adding to the never ending lust/humiliation and degradation that I was growing to need and want from my girlfriend.

With that I cleaned her legs first making sure I cherished every moment I ran my tongue over her whether it being covered in another man’s cum or not as things were ramping up so quickly I didn’t know how often I’d be allowed to actually touch this beautiful girl. Cleaning up her feet was difficult at first as there was so much cum covering her feet, she made me clean all of her heels first before making me remove each shoe and clean it with the inside using my tongue for every nook and cranny, I learned quickly on her first high heel to do a good job as she slapped me and spat on me for doing what she considered as a bad job.

Cleaning her feet felt like another moment I’ll never forget, the rich taste of her feet that had mixed with cum and sweat made this first experience a sensory overload. Licking between each toe felt like I could have burst through my chastity cage every time and Jenny seemed to like watching me lick another man’s cum off her feet, she’d been rubbing Marks cum into her pushy the whole time making a huge mess and causing me to worry about her getting pregnant at the back of my head.
In between every couple of licks cleaning her pussy she’d pull me up and stick her tongue in my mouth searching for Marks cum mixed between my saliva and her juices. I was all to willing every time.

After making sure she was absolutely clean of Marks cum running my tongue all over her crotch and thoroughly in her pussy and on her asshole I made sure to lick her clit until she came and pulled me off and told me that I'd fulfilled my cuck job for the day, as we lay there with Jenny running her hand over my cage encased cock she asked how I liked my new position and my new fulfilments to my new mistress. With my heart still beating harder than a jackhammer digging up concrete I’ll never forget saying “I can’t believe how lucky I am!“ with that she gave me a big wet sloppy kiss which being as hot as it was still tasted like a mix of Jenny’s pussy and Marks cum.

After laying together for a bit Jenny fell asleep but it took me the longest time thinking about the things that had happened that day, my cock was swollen and hurting but the reality of being cuckolded in such a dirty depraved way for the first time was amazingly hotter than I’d ever imagined. I could only imagine that it would get more interesting with time.

The next experience I post will be what I consider the hottest time with Jenny and then everything after that will be hot sessions or things she did during our relationship and really short depraved snippets I’ll never forget.
  • Like
  • Love
Reactions: Doorstopper, whitewife696969, robbiewillskucku and 1 other person