Cuckold Husbands Regret Ch. 01

All that was going through Frank's mind was how ravishing Jennifer looked with her long blonde hair tied up in a pony tale and was even more excited that he was possibly going to fuck her.

"Frank: Wayne I must say, you're a lucky man to have such a beautiful wife."

"Wayne: Already starting with the compliment I see."

Frank: Well I'm not here to lie, I'm just here to accomodate yours and your wife's request."

After a good amount of small talk Jennifer sat there quiet most of the time just going over how she could potentially be fucking the man that sat infront of her that was not her husband.

"Frank: so Wayne, with all being said, would you be cool with me swapping places with you so I'm sitting next to your wife, only if that's ok with her ofcourse."

"Wayne: That's ok with me, I don't see why we can't start now, what do you think my love."

"Jennifer: Yea I guess that'll be ok."

Just then, Frank and Wayne switched places to where Wayne was now across from his wife sitting next to another man.

Frank could smell the sweet aroma coming from Jennifer and it started to turn him on. He began to make some more small talk with Wayne always keeping eye contact with him and as he was doing that, his hand started to wander onto Jennifer's thigh where Wayne couldn't see.

Jennifer flinched when Frank placed his hand on her thigh so Wayne asked if she was ok and Jennifer replied, yes I'm fine. When Frank heard that, he decided to push it a little further and pulled up her short skirt and placed his hand between her thigh rubbing up and down but kept it there without going any further.

"Frank: So I'm honest and open and wanted to bring up your question about me sending a picture of my penis, is that something you 2 wanted?"

"Jennifer: Yes please."

"Frank: before we do that, I have 1 question for you Wayne, how much do you truly know about what being a cuckold is?"

"Wayne: Well I do understand it is where I watch another man fuck my wife."

"Frank: Well that is true but there's many different forms of what of being a cuckold is, my type is the dominant type and if this is going to be a 1 time thing I'd like to give you 2 a proper experience of it, of my my type that is, so if you're up for it just let me know."

"Jennifer: Can you explain your type?"

"Frank: My type would be where, your husband would obviously watch me have sex with you but the catch is, he would be required to do as I say as well, I've had men that got off just from being tied to a chair and watching me have my way with their wives I've had men that have loved being naked with a collar on and sat in a corner but what made them enjoy it was the thrill of never knowing, so would that be something you're interested in?"

"Wayne: If that's what would give us the best one time experience then I'm more than happy to do that."

"Frank: Ok back to the cock conversation, there's a public restroom away from everyone just a 5 minute walk from here, I want you both to follow me so you can see it with your own eyes."

Just then Frank went into the Cafe and paid the bill for both of their meals and started walking towards the public restroom. As he got in there both Wayne and Jennifer walked in seconds after and one last time Frank asked them.

"Frank: Do you 2 want to see my cock."

"Jennifer & Wayne: Yes."

"Frank: Ok Jennifer if you want to see it, I want you to get it out yourself."

Jennifer then looked at Wayne and he could tell the hesitation she had at that moment and that she wanted to just run but to herself Jennifer thought she had come this far and that she may as well see it though. With a deep breath, Jennifer got on her knees and slowly unbuckled Frank's belt, pulled down his zipper and from his waist band proceeded to pull down his briefs, and at no point was Jennifer or Wayne prepared for what popped out.

Standing there both shocked with wide eyes.

"Jennifer: What the fuck is that?"

"Frank: is it big?"

"Jennifer: It's a monster, I don't even think it'll fit in me."

"Frank: It's just over 10 inches fully erect with a girth you wouldn't be able to fit a hand around, so if you want to take a picture, now is the chance."

"Jennifer: Here's my phone, take a picture of me holding it, it's the biggest cock I've ever seen."

On the car ride home, Wayne was quiet to say the least but Jennifer on the other hand was screaming in her head.

When they were home Wayne finally spoke.

"Wayne: Do you still want to go through with this?"

"Jennifer: Most definitely not."

***************

Dear Frank

Myself and Jennifer have spoken and we think it's best we not go through with it.

Yours Sincerely Wayne

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Dear Wayne

Could you please tell me why a change of heart?

Yours Sincerely Frank

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Dear Frank

Myself and Jennifer have had a pretty ok sex life our entire marriage and in complete honesty, our worry is the size of your cock, yes it's a 1 time thing but the size scares her.

Yours Sincerely Wayne

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Dear Wayne

If it is a 1 time thing, I do have a solution.

I have been in this situation before and trust me I can make this enjoyable for all of us. If you're truly keen on being a cuck for once in your life, I can train Jennifer's pussy to take my cock, what that means is, I have a sex machine and different sized dildos to accommodate and slowly move up before she's confident enough to take me. And when she does finally have enough training, she can and that's it, your cuck experience would be over. If that sounds like a plan I'd love to hear back from you.

Yours Sincerely Frank

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Dear Frank

I have spoken with Jennifer about your proposal and she would be ok with trying it your way because she said you seemed nice enough at the Cafe and that rather than us waste time we might as well give it a go.

Yours Sincerely Wayne

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Dear Wayne

I'm glad to hear you are both on board, here's my address. I want both of you at my house 9pm sharp no later, please be prepared.

Yours Sincerely Frank

*******************

When the last email was sent their nerves had set in and though he never said anything to Jennifer, Wayne's main concern was his cock being that much smaller to that of Frank's, so there was a feeling of Jealousy, but seeing as Jennifer didn't want to go through with it he felt safe and he could use that to keep his control of the situation.

At 7:30pm Wayne watched Jennifer as she was picking out some panties and his nerves started to get the best of him, so to get past that, he decided without a second thought, to have his way with Jennifer before they left.

Unaware to Jennifer, Wayne walked up behind her tearing off her clothes pushing her naked body up against the wall a vigorously poking her pussy. Jennifer never said a word because she was actually enjoying it, she was enjoying this side of Wayne. Just then he pushed Jennifer to her knees having her suck his cock for the next 2 minute before standing her back up and slowly pushing his cock in her.

As he bent her over he grabbed a fist full of hair and started fucking her causing her to moan even more and for what seemed like an eternity, Jennifer squirted all over the bed sheets something she had not done in so long.

"Jennifer: That's it my love, fuck this pussy, take this pussy, cum in me now."

Wayne didn't need to be told a second time and blasted in Jennifer but knowing the time they both got up and headed for a shower to get ready.

When they got to Frank's drive way, they parked up, had a breather said I love you to eachother followed by a kiss and made their way to his front door by walking up the small set of steps he had.

Jennifer was ultimately the one to knock on his door as they waited nervously knowing there was no turning back. Just then Frank opened the door standing there with no shirt on showing off his somewhat of a 6pack of abs. As a shock to both Jennifer and Wayne when Jennifer stepped in the door, Frank pulled her in tight by the waist and gave her a firm kiss on the lips which she returned making Wayne both Jealous and aroused that his wife somehow willingly kissed a younger man.

When they walked inside, Frank took them to a room at the other end of the house and said.

"Frank: This right here is where the training will take place, do you have any questions?"

"Wayne: Yes, what is the process of tonight going to be?"

"Frank: Well first of all what are your guys limits?"

"Jennifer: Seeing as I'd be the main player in this thing, I'll make that decision by saying, at no point is there to be any butt stuff and besides that I'm open to following your instructions when it comes to my training."

"Frank: Ok, first off, Wayne, I want you to sit In that chair and Jennifer come and sit next to me on the bed."

When Jennifer and Wayne had sat down, Frank placed his opposite hand in between Jennifer's thigh.

"Frank: Wayne at no point are you to look away or try to stop me."

As he said that, Frank turned to Jennifer and spread legs apart as she leaned back on her hands. Frank began to slowly caress the inside of her thighs causing her to shiver with each light touch moving closer to her panties and when she let out her next moan, Frank darted his tongue into her mouth and their lips were locked as they made out right infront Frank who wanted to stop it but couldn't help his arousal. Frank then got to her panties and started rubbing her pussy setting it off like a sprinkler system with the amount of juice drenching the gusset but Frank ended up telling Jennifer.

"Frank: Alright, now stand up and take your panties off then walk over to your husband and put them in his mouth."

She walked over to Wayne who was in shock, opened his mouth and put in her wet panties.

"Frank: Now I want you to stand him, strip him naked and blindfold him then tie him to the chair he's in."

As instructed Jennifer stood him up, took off his clothes, blindfolded him and tied him to the chair as best she could. Wayne on the other hand was sat there in shock as this was all happening and now with no vision.

"Frank: Now Frank, I'm going to take Jennifer to my room and Prepare her for her training at no point are those panties to leave your mouth, Jennifer follow me."

When they got to the room Frank said to Jennifer.

"Frank: Alright now take off your dress and bra so you're completely naked then put on this tight black 1 piece suit.

When she was done, she looked down at her crotch.

"Jennifer: is there supposed to be a hole there?"

"Frank: Yes there is, now walk towards me, so I can inspect your body.

As she was standing in front of Frank, he started sucking on her nipples through the 1 piece suit and poking her pussy and noticed that it felt wetter than he was expecting.

"Frank: Why is your pussy so wet?"

"Jennifer: I had sex with with Wayne before we came here."

"Frank: Ok, that's about to stop."

He then stood up and proceeded to walk Jennifer back to his training room then made her take off Wayne blindfold.

"Frank: Now, I'm going to say this once and once only, Jennifer has informed me, you 2 had sex before you came here, that is not to happen again. The days yous are coming over for training, you are not permitted or allowed to have sex and from now on Jennifer when you and Wayne are in my presence you are to refer to him as cuck only do I make myself clear."

"Jennifer: Yes."

"Frank: on days of training, this 1 piece suit is the only thing you are to be wearing and I want your pussy clean shaven at all time, am I clear?"

"Jennifer: Yes."

"Frank: Alright, now what I want you to do is, take your panties out of Wayne's mouth and untie him. And Wayne once she done then I want you to eat her pussy and make her cum so she's ready for her training, do you object to anything I've said?"

"Wayne: No."

"Frank: Ok good we can begin, and just to let yous know, the training will take 1 month Max and once myself and Jennifer have had sex, then you 2 won't have to see me again, are yous good with that?"

"Wayne & Jennifer: Yes."

"Frank: Alright, now begin."

He stood there in amazement as this married couple were doing as they were told, Jennifer climbed on to the bed on all fours as Wayne followed staring at her pussy as he started licking.

"Jennifer: Mmmmmm that's it cuck, lick my fucking pussy like a good boy, get me ready for my training."

With that Frank started setting up his training gear, he first put up the type of chair you'd find in a Gyno office with the stirrups and bought in a bag full of different sized dildos to put on the machine. As he rolled in the chair to put it in the opposite corner they kept going and not stopping, he then lowered the chair so it was level enough for the machine to make sure Jennifer's first training session was comfortable.

"Frank: So Jennifer, is he eating your pussy well enough to cum?"

"Jennifer: No, the cuck isn't."

"Frank: Alright cuck, this is how's its going to be, the size of dildo going in Jennifer will depend on how quick you can finish her off, the longer you take, the bigger it'll get, so, I suggest you hurry."

"Jennifer: Hurry up cuck and make me cum, if I get ripped you won't be getting any sex for the entire month."

That gave Frank an idea.

"Frank: not to be mistaken but you must also know Wayne, you will not be cumming tonight or this month, sex may be on the table but you cumming is not allowed, even masturbation is off the table for the month and in saying that, for my services I will be expecting complete honesty from you both, if I don't get complete honesty, I will call quits on this whole thing.

"Jennifer: Did you hear that cuck, hurry just make me cum."

Sure enough the way Wayne was eating her pussy was as if he was making love to it.

"Jennifer: That's right cuck just like that, suck my pussy right now, I'm about to fucking cum don't stop."

Just then, Jennifer's body dropped and she started spazzing from the orgasm she just recieved.

"Jennifer: Where did that come from cuck, you've never eaten my pussy like that before, maybe if you made me cum like that more often we wouldn't be here."

"Frank: That's enough, now tie him back up the way he was before and stand infront me."

When Jennifer was done putting her panties back in Wayne's mouth and tied him up, she walked over to Frank just as she did in the room before hand.

Frank couldn't stop looking at the beauty that stood there before him knowing that Wayne was sitting there watching his wife, the love of his life prepare to begin the training of taking another man's cock. In his mind, Wayne thought Jennifer was just going to be trained but Frank had other ideas to further humiliate Wayne and have a little fun.

When Jennifer was stood infront of Frank as he sat down he pulled her in close and placed both of his hands tightly on her firm ass cheeks and started sucking on her nipples through the fabric of the 1 piece suit. Jennifer just stood there with her back to Wayne and with both the feeling over arousal and guilt to the point she didn't know what to do, but because she had her Husbands permission she ultimately chose to enjoy it placing a hand on the back of Frank's head as he was sucking on each nipple being covered by fabric, she even went as far as letting out moans and forgetting that Wayne was at the back of her. Frank then stood up.

"Frank: Alright, now what I want you to do Jennifer is getting down on your knees and pull out my cock."

She then proceeded to do as she was instructed by getting down on her knees with her back still facing Wayne and slowly but surely rubbed the bulge of Frank's cock then put her hands in the elastic waistband of his sweat pants and pulled them down as seductive as she could. When his cock popped out, she didn't ask any questions or say a word, she just spat on the head of his cock and started stroking it and in the background they could both hear Wayne squirming in his seat.

"Frank: Get up and take your panties out of his mouth."

"Wayne: What the fuck is going on, how is this a part of her training."

"Frank: Cuck, all I told her to do was pull my cock out, anything after that is on her, so you might want to ask her that question."

"Wayne: What the hell are you doing Jennifer?"

"Jennifer: My love, I mean cuck, I just want to see it at full strength so I know what I'm getting myself into so calm down."

Just then she put her panties back into his mouth but this time put tape around his mouth as well then proceeded to get back on her knees infront of Frank and continue stroking. Frank was having a blast and from what Jennifer just did he started getting turned on and said.

"Frank: That's its baby, now put it in your mouth."

"Jennifer: I can't do that, what about my husband."

"Frank: you can and you will, and what's he going to do, the cuck is sitting there tied up, now suck it."

At first it was a struggle for Jennifer once he was fully erect because she had never had a cock that big in her mouth but due to all the saliva it began to become easier for her. She was enjoying herself as time passed with a gigantic cock in her mouth and even the squirming from Wayne had stopped.

As he sat there watching, he now finally got why Frank said that, when at first a cuck would get jealous bit start to enjoy it and get aroused and it was true because Wayne started getting hard watching his wife suck another man's cock.

"Frank: Mmmm that's it bitch gag on my cock, you're a good cock sucker aren't you."

"Jennifer: I hope I am."

With his hand holding her ponytail.

"Frank: Don't worry baby you are, now get ready because I'm about to cum on you."

"Jennifer: Please don't."

"Frank: Be quiet or ill make you swallow it just take a look at your cuck husband, he's enjoying it, his cock is hard."

"Jennifer: are you enjoying this cuck?"

He nodded no.

"Jennifer: Then why is your small cock so hard, do you like me with another man's big cock barely fitting in my mouth?"

He nodded no as Jennifer started to suck Frank's cock again.

"Jennifer: Alright Frank, hurry up and cum on my chest with your fat cock.

She started spitting and stroking his cock as fast as she could with both hands barely fitting around his shaft aimed at her chest. Then suddenly Jennifer freaked as she had never in her life seen so much cum shoot from a cock and even though she felt dirty as it was happening, she also felt proud that she was the one who made it happen. When Frank was done Jennifer was in for a shock.

"Frank: Now scoop some up and taste it."

"Frank: Alright, that's a good girl, how did it taste?"

"Jennifer: It tasted ok."

"Frank: Have you ever tasted cum before."

"Jennifer: I tasted cucks once but you tasted a lot better."

"Frank: So, my cock is bigger than his and I taste better than him, now what I want you to do is, go up to him and rub your cum filled chest all over his face."

"Jennifer: Don't make me do it, he's already been humiliated enough."

"Frank: I'm not asking you, I'm telling you."

She turns towards Wayne and starts walking upto him slowly with her head down, when she got to him though, she sat on him placing his much smaller cock into her sloppy pussy and whispered in his ear so Frank couldn't hear and said.

"Jennifer: I'm sorry my love."

As she was rubbing her chest in his face, she began to ride him and something in Frank could tell Wayne was going to cum.

"Frank: Ok that's enough get up and sit in the chair and put your feet in the stirrups."

She did as she was told and when she was sitting in the chair, Frank tightened the on her feet hands and waist.

"Jennifer: What the hell are you doing?"

"Frank: don't you worry, it's to hold you in place when you orgasm and the machine keeps going."