Cuckold Husbands Regret Ch. 01

Frank then got his bag and walked up to Wayne pulling out the first dildo and measuring it next to Wayne's cock and the first one was the smallest out of the 4 but still had a lot more girth and length than to that of Wayne's cock.

He then proceed to place it onto the end of the machine.

"Jennifer: That's to big."

"Frank: You're being trained so be quiet."

When the dildo was on the end of the machine, he lubed up the dildo and put it to the entrance of Jennifer's pussy. As the machine turned on and first penetrated Jennifer slowly, she gasped for air.

"Frank: Jennifer I suggest you take it because it's going to start speeding up and when you orgasm, I don't want you thinking it's going to stop."

True to his word, Frank turned up the speed.

"Jennifer: Take it out, take it out, it's hurting."

He stood up and started kissing Jennifer with passion and and rubbing her clit to get her wet.

"Frank: Don't worry baby, it won't hurt for much longer, I'll look after that pussy and make sure you go home satisfied."

"Jennifer: Don't call me baby, I'm married, I love my husband."

"Frank: Look at cuck, if you loved him, you wouldn't be here right now, so you will enjoy it."

He kept kissing her and she gave in and started kissing him back as she got more turned on by him rubbing her clit along with the thrusts of the dildo. When he turned up the speed, she screamed.

"Frank: That's it baby, take it, you like that don't you?"

By this time she didn't even care Wayne was watching.

"Jennifer: Yes, I do, I want it faster."

That's was all the confirmation Frank needed and only a Max of 10 seconds after making the machine go faster Jennifer went wild with her vocabulary.

"Jennifer: Oh my fucking God, fuck my fucking pussy with that fat fucking dildo, fuuuuuuuuuuck, don't fucking stop, I'm cummmmming fuuuuuuuuuuck."

After that, the squirming coming from Jennifer even to Frank seemed impossible, how could that come from one lady but he kept the machine going and Jennifer was being hit with orgasm after orgasm.

"Frank: Has cuck ever made you orgasm like this."

"Jennifer: Never, ohhhhh fuuuuck, in our entire marriage."

He then proceeded to slow the machine down and eventually stop it and take it out of Jennifer and placing his fingers in her pussy then making out her at the sametime.

"Frank: Mmmm do you like that baby."

"Jennifer: I truly do, thank you for giving me a break."

"Frank: Have you had enough of the machine?"

"Jennifer: Yes, for tonight I have."

"Frank: Ok, as it is your first night of training I'll let you off this time, you can get up now."

"Jennifer: Thank you, but I'm going to need help getting up please."

"Frank: That's fine, I'm going to carry you to my room, so I can have a word with cuck."

Just then Frank picked up Jennifer and carried her to his room and lay her on his bed then grabbed a pen and paper, wrote his number down placed it under her tit and told Jennifer.

"Frank: Keep my number and don't tell your husband you have it, well not just yet anyway am I clear?"

"Jennifer: Yes, but wouldn't that be cheating?"

"Frank: It's not about cheating, it's part of your training, it's about loyalty."

He then made his way back the the training room to take the panties out of Wayne's mouth to have a word with him.

"Frank: So Wayne, how was this experience for you, was there anything you felt uncomfortable with?"

"Wayne: At the beginning yes, I couldn't understand why she was sucking your cock but as it being my first experience, I understood things like this would happen and I actually started to enjoy myself.

"Frank: So you have no objections to anything that was said, as in, you're not allowed to cum over the duration of the month?"

"Wayne: No objections, it may be hard but we started this for a reason and I'm willing to stick it out."

"Frank: That's good to hear, well seeing as we're done for tonight, I'm going to untie you so you can get dressed and pick up Jennifer because she's going to need help getting up and to the car, but she is not allowed to take the 1 piece suit off until you and her get home, and our training will be every second night at 9pm."

Once Wayne was untied he quickly got dressed and went to Frank's room to get Jennifer and take her home. When he assisted her in the door he took her into the room and began to take her 1 piece suit off when he noticed something square by her tit.

"Wayne: What's that there?"

"Jennifer: It's nothing don't worry.

"Wayne: would you like me to wash you?"

"Jennifer: No don't worry I'll do it."

"Wayne: What about all of Frank's cum on you."

"Jennifer: What about it?"

"Wayne: Well don't you want to wash it off?"

"Jennifer: Not right now I'll get it when I can."

Wayne then proceeded to walk off to take a shower and all that was going through Jennifer's mind was, how powerful her orgasm was and how her pussy now felt. She was still getting over the fact she had another man's cock in her mouth and how ravaged her pussy felt after her first training session.

As these thoughts were going through her head she noticed her hand was making its way to her pussy. Once it got there she was surprised at how sensitive it still was and slowly began rubbing her clit and entire pussy, she then noticed at how stretched she felt just from one session but knew it would eventually make its way back to normal.

Jennifer kept masturbating ever so slowly when Wayne walked out of the shower and witnessed her fingers in her pussy.

"Wayne: What are you doing."

"Jennifer: Just rubbing my pussy, it feels like it took a pounding and now I'm just rubbing it to calm it down."

"Wayne: Would you like me to do that for you?"

"Jennifer: No, I can do it myself, you just go to sleep, I'll be done soon."

Minutes later both Jennifer and Wayne were asleep.

When Jennifer woke up the feeling in her legs had come back but she was still in the 1 piece suit with dried up cum on her. As she looked to her side Wayne wasn't there and had already left for work and when she looked at the clock, she knew she had better do the same.

When she got undressed for the shower, Frank's number fell to the ground so she picked it up and sent him a text.

"Jennifer: Hey Frank it's Jennifer this is my number."

When she got out of the shower she had a message waiting.

"Frank: Hey baby how are you feeling?"

"Jennifer: Im feeling good, thank you for lastnight, it was amazing."

"Frank: No need for thanks, I'm just trying to help, what are your plans for the day?"

"Jennifer: I've just finished a shower and put the one piece suit in the wash and now I'm getting ready for work."

"Frank: How would you like a lunch date today?"

"Jennifer" Maybe, I don't know, wouldn't that be pushing it meeting up with you, without my husband?"

"Frank: Not at all, there's no training involved, just a lunch date, so are you in?"

"Jennifer: Ok, count me in."

Once Jennifer got dressed she left for work but as she got there her work colleagues noticed she was walking weird and asked if she was ok and she just replied yes.

When she sat at her desk, she could still feel the tenderness of her pussy and flashes of the night before started coming back and it began to turn her on but what made the situation worse, was the fact she was meeting the man who caused this for lunch and she couldn't wait to see him.

As lunch came she got in her car and headed straight to the lunch bar to meet Frank and when she pulled up, she could already see him.

"Jennifer: When did you get here?"

"Frank: Not long ago, you're looking beautiful today, may I steal a kiss?"

"Jennifer: For that compliment, yes you may."

So Frank stood up and planted a kiss right on Jennifer's lips.

"Frank: Did Wayne tell you about our Training days?"

"Jennifer: Yes, he briefly mentioned every second night at 9pm."

"Frank: Ok that's good, and do you remember on days of training, the one piece suit must be worn all day?"

"Jennifer: But I have work tomorrow."

"Frank: Well I guess you'll be taking the day off, listen it's only for a month and after that your lives can go back to normal and don't forget shave your pussy tonight."

"Jennifer: Ok, well I've got to get back to work, I'll see you tomorrow."

At work Jennifer started to feel guilty about having Frank's number and now hiding the fact she just had lunch with Frank from her husband.

The night went as it normally did nothing to major, both Jennifer and Wayne had dinner then went straight to bed. When she woke up, Jennifer collected the one piece suit and put it on and lounged around in it all day waiting for Wayne to get home from work so she could get to her training because she was actually looking forward to it.

When they got to Frank's house the process was the same, he was happy her pussy was shaved so he said to Wayne.

"Frank: Ok Wayne I want you to wait outside the training room for a few minutes whilst I take Jennifer in there to begin training."

"Wayne: Why can't I be in there?"

"Frank: I'll tell you when I come out."

So Frank and Jennifer went into the training room and he made Jennifer drop to her knees and start sucking his cock and as she was gagging he could hear a knocking at the closed door.

"Frank: Hold on I'll be out there in a sec."

So Frank started ramming his cock down her throat even harder then eventually covered Jennifer in his cum all over her face and tits before lifting her up and placing her in the chair and strapping her in. When she was strapped in he told her.

"Frank: The next couple of weeks are going to be different baby."

"Jennifer: What do you mean?"

"Frank: Well today, your getting a bigger dildo and you'll be left of the machine for 30 minutes and once done that'll be your training over."

He then spit on her pussy and placed the dildo inside her, turned it on and walked out of the room naked to make Wayne jealous of his size.

"Wayne: So what was that about?"

"Frank: Well before I bought it up with you, I wanted to let Jennifer know first that over the next couple of weeks, there won't be any training with us in the room only her and each session will only go for 30 minutes, there's no reason to have you as a cuck when nothing is happening. The reason for this whole thing is for you to be a cuck when I fuck her and the first session was just to give you a taste of what that'll be like."

"Wayne: Ok but that doesn't explain why you're naked."

"Frank: The reason I'm naked, is so that when I get a bigger dildo I can place it next to my cock for her to see her progress like I did tonight, I also had her suck my cock to get her motor running. I've put a bigger dildo in her, can't you hear her cries?"

"Wayne: I can, will she be ok?"

"Frank: ofcourse she will, it's just going to take a few minutes before she gets used to the size."

*25 minutes later*

"Frank: Ok, I'm going to turn off the machine, her training is done for the night, I want you to follow me."

When Frank and Wayne entered the room, Jennifer was shocked to see both of them, wondering in her head what her husband would be thinking of her in that moment with a big puddle of her juices on the floor.

Once Frank turned off the machine and took it out of Jennifer, she felt a sense of relief come over her as her body was shaking and spazzing uncontrollably. As she repeated the word fuck, Frank sat in between her legs as she was still strapped in and lightly started rubbing her bald pussy and clit.

"Jennifer: Be gentle."

"Frank: Don't worry, I'll take care of you."

As he kept rubbing, he slowly started sliding 2 fingers in and out which started to turn her on again.

"Frank: So before we end this session, I need to have a word with both of you, to make sure you still want to continue after tonight because after tonight there's definitely no turning back."

"Wayne: Sure what's up."

"Frank: As the training progresses, Jennifer's pussy is going to stretch each time, and with each time it stretches there's a possibility it'll never be the same after the month is over."

"Wayne: What does that mean exactly."

"Frank: what that means is, is that after this month is over and life goes back to normal, your sex life may never be the same because her pussy will have opened up a lot more."

"Wayne: Oh shit, I didn't think about that."

"Jennifer: What do you mean you didn't think about that, I'm the one being trained, the decision to keep going should be up to me, not you."

Whilst this conversation is happening, Frank is still poking and rubbing Jennifer's pussy and at that point, Wayne started getting jealous.

"Wayne: I know I'm just saying."

"Frank: Well do you 2 wish to continue?"

"Jennifer: We do."

When Jennifer and Wayne got home, Jennifer just told Wayne to lay her on the bed once again before he showered, but when he got out he asked her.

"Wayne: My love, aren't you worried about getting stretched?"

"Jennifer: ofcourse I am, I was worried when I first had seen his penis, but because I was doing it for you, it didn't matter, please don't bother me tonight I'm need some sleep."

Over the period of the next 2 weeks Jennifer's training was mixed with pleasure and pain as the dildo moved up in size each time. Wayne on the other hand noticed a change in his wife's attitude, which to him was both sexy and annoying but he was glad this somewhat of a nightmare was almost over but his hormones were getting the best of him and he constantly kept asking Jennifer for sex but she kept denying him her body which started to annoy her and she said to him.

"Jennifer: If you want to have sex with me, and put that cock in me, you can ask Frank."

"Wayne: I shouldn't have to ask Frank if I can have sex with my own wife, what's gotten into you?"

"Jennifer: Nothing has, but if you knew how my pussy felt after each training session you'd understand, so as I said before, if you want to have sex, ask Frank coz I don't want it messing with my training."

Feeling defeated, Wayne did as Jennifer said and called Frank.

"Wayne: Hey Frank, I just wanted to know, would it be ok to have sex with Jennifer?"

He couldn't believe he had to ask Frank for permission to fuck his own wife which started pissing him off because he felt it was going to far.

"Frank: She's your wife, do as you please just remember what I said, you can't cum, and if you do this whole thing will be called off."

"Wayne: thanks Frank, see you at the next training session."

Wayne walked back into their room and told Jennifer, Frank was ok with it, so without hesitation Jennifer got on all fours in the doggy position ready for Wayne to put his cock in her when she felt his tongue enter her pussy.

"Jennifer: What are you doing, you asked to have sex, not eat my pussy, put your cock in me already so I can sleep."

"Wayne: What's your problem?"

"Jennifer: My fucking pussy hurts, that's what's the problem."

He froze for a few seconds then put his cock in Jennifer but he could now feel the difference that she was stretched and his cock was barely doing anything. He kept pumping and pumping but the sex just wasn't the same, yes her pussy felt amazing but the sex just had no emotion behind it, so he slammed and slammed and slammed harder and harder then for him tragedy struck, he had ejaculated all in Jennifer's pussy.

"Jennifer: What the fuck did you just do."

"Wayne: I came I didn't mean to, it was an accident."

"Jennifer: Accident or not, you knew the rule, so who's going to tell Frank you cum in me."

"Wayne: He doesn't need to be told."

"Jennifer: Well if you don't tell him, I will."

"Wayne: How would you do that huh?"

"Jennifer: I have his number, that's how."

"Wayne: Alright alright I'll tell him."

When she said that to him, he got agitated and angry but thought it may be better he do it than her as he did make a deal with Frank.

The phone kept ringing and there was no answer and this went on for about 20 minutes before Frank finally picked up the phone.

"Frank: How was the sex."

"Wayne: It was good and bad."

"Frank: What do you mean."

"Wayne: Well her pussy felt good as always but I cum in her, I didn't mean to but it just happened."

"Frank: First off i want to say thank you for being honest and letting me know but because you've broke the deal we made you knew the risks, and it's because of that, I can't participate in this anymore."

After saying that Frank immediately hung up the phone and knew there was about to be an argument between Wayne and Jennifer and all he was doing was waiting on the call from either one of them.

"Jennifer: So what did Frank say."

"Wayne: He said that because I broke my end of the deal, he's no longer willing to participate."

"Jennifer: Please tell me you're kidding."

"Wayne: I'm Sorry my love but I'm not."

"Jennifer: You fucking idiot, all you had to do was not cum and you couldn't even do that, I went through those weeks of training my pussy and stretching it, knowing it'll never be the same again for absolutely nothing. I was doing this for you when I didn't want to do it, and you only had to last 5 more sessions."

"Wayne: I'm sorry my love, I truly am please forgive me."

"Jennifer: No cuck, I will not forgive you, I did this for you, and you messed it up."

After that heated argument Jennifer was wondering if she should message Frank to see if there was an arrangement they could come to but decided not to incase it made the situation worse. Over the next few days Jennifer and Wayne did not speak at all, they didn't even sleep together and Jennifer started to actually miss her training sessions so bad she actually started crying, which those feeling would have been heightened due to it being that time of the month.

One night as Jennifer lay in bed crying, Wayne happened to walk past her door and ask.

"Wayne: My love what's going on are you ok."

"Jennifer: Go away, don't touch me, this is all your fault, why couldn't you keep your word."

He then started to feel guilty for putting his wife through this ordeal and wanted to comfort her but didn't know how. He felt the best thing he could do was to call Frank to see if he could change his mind. When Wayne was trying to call Frank, he never answered for another day but when he finally picked up Wayne spoke.

"Wayne: Hey Frank sorry for all the calls I was wondering if I could get a moment of your time?"

"Frank: Yea sure what's up?"

"Wayne: Look I feel absolutely bad for not keeping my side of the deal but I don't feel Jennifer should be getting punished for it, she has put in so much effort."

"Frank: So are you telling me that you should be the one being punished and not her?"

"Wayne: Yes."

"Frank: Alright, if you believe you should be the one getting punished, I've got an idea but you probably won't like it."

"Wayne: If it'll cheer up Jennifer then just name it."

"Frank: Ok, well as you know, before you broke our deal before, there were only 5 training sessions left but my new deal is, if you want this to continue there won't be 5 training sessions, the big deed will happen in 5 days."

"Wayne: What do I have to do?"

"Frank: what I want you to do is drop Jennifer off to my house for 3 days."

"Wayne: It's that time of the month for her she has 2 days left on it."

"Frank: Ok, then in 3 days, I want you to bring her over for 3 days then she will have 2 days to rest before you watch us have sex."

"Wayne: Ok do we need to bring anything for the 3 days?"

"Frank: I don't think you understood me correctly, when I said I want you to bring her over for 3 days I meant you won't be there with us for her training, because it's going to be intense and it's part of your punishment."

"Wayne: So let me get this straight, you want me to drop my wife off to your house for 3 days for training then after 3 days pick her up to rest for 2 days before you fuck her?"