My Cuckold Story Ch. 03

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Steve takes my wife's anal virginity.
2.2k words
4.02
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33

Part 3 of the 3 part series

Updated 06/08/2023
Created 01/27/2018
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This is another chapter in "My Cuckold Story", it will make the most sense if you read the other two chapters first. This is about cuckolding, if that isn't your thing, don't read any further. I hope you enjoy!

The next week went by like everything went back to normal. My wife and I went back to having normal vanilla sex, and we didn't talk to Steve at all. It was like nothing had ever happened, until I received a call from the doctor's office telling me my STD tests can back all clear and told me they send me a digital copy of my clean report. I knew that as soon as I told my wife Steve would be fucking her bareback. As a drove home, I debated not telling my wife, but part of me wanted her to keep doing it. Little did I know, I wouldn't have much of a choice.

As I got home, Steve and my Wife were both waiting for me in the living room, sitting down on the couch. Steve spoke first, "You get you tests results back?" I nodded my head in the affirmative. "Perfect." He gestured towards the table. "Put that on and I will tell you what will happen next." On the table, was a new chastity device, smaller and higher quality than the one I currently had. I quickly obeyed and while I was putting it on Steve continued to speak, "This one is smaller, its not like a cuck like yourself with have much use for that clit in-between your legs. It also has an anti-pull out piece that way we don't repeat what happened last week." As he finished speaking, I fixed the anti-pull out in place and turned the key in the lock and handed it to Steve.

"Don't hand it to me. Your wife will hold on to it for me, and she will follow my instructions of when to release you." I handed the key to my wife. Steve continued on, "Now, if you thought last week's punishment for masturbating without permission was just you not being able to fuck your wife, you were wrong. We are going to play a game. I am going to fuck your wife bareback. You will never be allowed in the room when she is pleasing me. For every orgasm she has, you will get a coin flip. Get three heads in a row, and your wife has instructions to let you out and to let you use her in any way you want. If you flip and get tails, your count gets reset to 0. You will have to check her body for my signature to see how many flips you get. You can only search her body once I left your house, or once she comes back from mine. It's that simple." With that, he grabbed Maggie's hand and headed upstairs. Over his shoulder he said, "Stay down here cuck, we are about to find out how many coin flips you get you get today."

Very quickly, I heard the bed moving and Maggie's moans. I tested Steve's claim that I couldn't pull out this cock cage, and very quickly learned how painful it was to try. I realized that I was stuck in this thing until he made my wife cum three times... at least. Within 10 minutes, the bed stopped moving and my wife was quiet, and I heard steps descend the stairs and the person left through the front door. I rushed upstairs and found Maggie splayed out on the bed and I scanned her over. She was running her hands through her messy hair. Her stomach was rapidly rising and falling to catch her breath, but my eyes stopped at her pussy. White gooey liquid was leaking out. In between her breaths she said,

"Oh my god Tom, he was amazing, it was nothing like last week. Last week he was a gentleman and had sex. This week, he took me. Used me as a set of holes, and his thick dick just kept slamming me. It was amazing. While she was describing he sex, her hand had moved towards her clit, and quickly retracted it and giggled, "Oops, I forgot the only person that's allow to touch me is him now." Quickly adding on, "Of course until you get your three heads in a row. Now, look for his signature, so I can jump into the shower." She reached out her hand which had a quarter in it.

I started to look her over for Steve's signature, and I found one on her inner right thigh, and on her neck. I quickly checked the quarter to make sure it had a heads side. I flipped the coin in the air, letting it bounce on the ground. Heads. Yes! Only two more to go. I flipped it again. Tails. I heard Maggie giggle,

"Looks like you are back to zero. I hope that cage is comfortable."

That is how my next two weeks went. Maggie and Steve would fuck daily, if not twice. He would either come over unannounced and have sex with Maggie in whatever room he found her in, while I was forced to leave, or he would text her and she would go next door and fuck him at his place. Every time after they were done, I would search her body for his signature and usually found two, sometimes only one. In those two weeks, I never got three heads in a row. I had two in a row multiple times but could never get the third. I was getting desperately horny, wanting any sort of relief, even just masturbating would have been heavenly. It didn't help that Maggie would sing the praises of Steve's sexual prowess in bed, or how she started dressing sluttier and sluttier under the guise. Why wear more clothes? Steve is just going to come over here and make me take them off anyway.

It was under these conditions, of teasing and lack of release in two weeks, that when Steve walked into our house early on a Saturday morning to fuck Maggie that I begged him to let me cum.

"Steve, please let Maggie unlock me. I need to cum so badly. You must've fucked her 20 times over this last two weeks. That's has to at least earn me one orgasm!" Steve looked at me blankly for a few seconds, and then smiled.

"I'll tell you what cuck. Ill make you a deal. I will allow you to masturbate but while you are doing so I will be fucking your wife of four years in the ass in the same room. If you cum first, I'll stop fucking her and you can have your wife for a week, but if I cum first there will be several repercussions. One, you will stop masturbating and once you get soft enough, go back in your cage without a release. Two, you will wear a butt plug and a pair of your wife's soiled panties for the rest of the day. Third, now you already do it, but I want it re-enforced, you will do everything I say for the rest of the day as well. Do we have a deal?

I looked desperately at my wife. Using my eyes, to ask a question that I couldn't say out loud. Honey, will you please let this guy take your anal virginity, so I can get off. She nodded her in agreement. So, I quickly replied, "Yes, we have a deal." I thought to myself. I don't care how tight Maggie's ass is, I haven't cum in two weeks, there is no way he cums before I do, especially with how much he has gotten off in the last two weeks.

Steve gave another big smile, "Great, lets head over to my place." We all walked over and headed upstairs to his bedroom. Steve got out a chair and set in front of the bed and gestured for me to sit. I took off all my clothes and sat down. My cock cage twitching in anticipation of finally having a release. Steve got out zip ties and locked my ankles and left hand in place. During that time, Maggie had completely undressed and was on all fours on the bed, with her head facing towards me. Steve got out special lube and undressed himself and started to lube up his cock and Maggie's brown hole. I couldn't take my eyes of his member. I now understand why my wife always referred to it as thick. It was larger than average probably about 8 inches at most, but it was THICK. I had never seen girthy cock, and I began to worry how it was going to fit into my wife. Steve must've seen my expression, because he said, "Don't worry, I'll be using plenty of lube. He got in position behind my wife and was about to work himself into her ass when I blurted,

"Steve, you have to unlock me and give some lube!"

"Oh yeah, that's right." He took the key off my wife's neck, went to a drawer and grabbed a plain clear bottle out of it. He walked off handed me the bottle and the key. He then reassumed the position behind Maggie and started to enter her. I could see the expression of pain on her face, but I quickly forgot about that, and went to work removing the cage and using the lube to start stoking myself. It felt amazing to be hard and be able to touch myself. I stroked myself quickly up and down, hoping to quickly end this experience for my wife. It wasn't long before I realized something wasn't right. The sensation started to fade away, I stroked faster and faster. Steve started to laugh,

"Yeah, that lube is numbing cream. Your only suppose to use a drop and rub it on the head, so with the amount you used, I doubt you'll feel anything soon."

I looked up in dismay, Steve was now fully in Maggie's ass and I couldn't even feel my dick. Now that Steve was fully in, he started to rock his hips back and forth taking Maggie's anal virginity. Her expression was slowly turning from pain to pleasure. One of her hands was rubbing her clit and she watched me stroke my cock. She began to moan,

"Oh that's feels so good. Take me like no man has ever taken me before. Oh god, Yes!" Her words died off and just became moans. Then, suddenly Steve stopped fucking her. "No, no, no, no, don't stop, that feels so good." In horror, I watched as Maggie began to buck her hips forwards and backwards fucking herself on his cock. Pushing him in and out of her, all the mean time moaning. Steve just laughed,

"Look at that. Your wife is an anal slut. Looks like she is really enjoying yourself. Aren't you, my little slut."

Maggie's moans increased, "Yes, I'm your slut. I'm your anal slut. Use me any way you want." With that, she cummed loudly. She continued moaning, still rubbing her clit. "Oh my god, I came from him fucking me in ass." I kept stroking myself, trying to cum to put an end to this. I knew if he came before I did, that I'd be wearing a butt plug and soiled panties for the rest of the day. Then, Steve grunts stopped as he pulled out of Maggie,

"I'm close, finish me in your mouth slut, and when I finish, don't swallow." Without any hesitation, Maggie turned around and engulfed him, sucking his all the way down to his balls. Within seconds, Steve released one loud grunt, and I could see his balls twitching. I thought I would never be more humiliated than what happened over the last few weeks, but watching my wife taste another man's seed after it had been in her ass all while I was watching was much more humiliating. After Steve was done cumming, he quickly barked an order to me,

"Stop touching your cuck, we had a deal." I whimpered but follow his orders. Still unable to feel my dick, any more stroking was useless. Steve then turned towards Maggie. "Would you be a dear, and please spit my cum in the panties you wore over here." My wife obeyed, getting her panties off the floor and spit his cum right in the middle. "Good, now toss them over to your husband. He will be wearing those for the rest of the day.

It took an hour for my cock to get soft enough to get back in the cage. I yelled out to Steve and Maggie who went down stairs while they waited for me to get soft. They came up stairs, and Steve got out a butt plug out his drawer, tossing it to Maggie,

"Be a dear and put this in your husband's ass." She covered it in lube and gestured for me to bend over the bed. Her lubricated fingers entered me, and the cool gel sent shivers up my spine. Without any warning, she shoved the entire thing in. Then Steve dropped the panties that my wife spit his cum into early next to my head.

"Go ahead and put those on with the rest of your clothes and get use to that plug. We will be going out later tonight. Be ready by eight."

To be continued.

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18 Comments
26thNC26thNCabout 5 years ago
Appalling

This is what makes a cuckolding relationship so appalling to the vast.majority of men and women. The extremely mentally ill might try it, but only the very sickest pursue it.

AnonymousAnonymousabout 5 years ago
Garbage

Way too short to be a chapter. More like a brief memo. Unfinished garbage. A man that is totally lacking in both pride and self respect. Do they even exist? Just the worry about diseases would be enough for him to divorce her. And Steve? He'd be lucky if Hubby didn't put a bullet in his pea brain. Awful story.

Cnj4funtimesCnj4funtimesover 5 years ago
Excellent - Please Continue

Love your story. It touches so many angles of what makes a cuckold relationship so appealing for so many men out there and woman for that matter. Thanks and please continue. And please pay no heed to those criticizing...as they just don’t get it....but so many of us do!

AnonymousAnonymousabout 6 years ago
Annette

You are one sick whore. How your husband could get near your nasty twat is something I could never understand. He must be the only person alive sicker than you.

NaughtyPoodle55NaughtyPoodle55about 6 years ago
Awesome

The story is awesome, please, keep on writing !

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