Cuckold Husbands Regret Ch. 01

This is my first story so i hope you guys like it. i have more ideas for a new chapter, let me know if you want to hear more after reading.

It was a Normal day at home for Wayne and his wife Jennifer who had been happily married for 20 years now both aged 46.

Wayne was your usual 46 year old, standing at 5'8 not very athletic but still in good shape for someone who worked as private landscape contractor, so he was always active.

His wife Jennifer was your usual conservative housewife that pranced around cleaning in a sundress on the daily while Wayne was always at work. For a lady her age, she still had guys turning their heads due to the way her ass swayed and tits bounced, but for Jennifer she only ever had eyes for Wayne and could never imagine sleeping with another man.

As Wayne got off work one day him and a few work friends went to the pub to wind down after another long day. Not long after their first round, Wayne was more quiet than usual when he overheard other patrons talking about swinging, so Wayne decided to go over and introduce himself.

"Wayne: Sorry to intrude, but I was wondering if I could join you?"

"Patrons: No problems, pull up a chair and join us."

"Wayne: I'm just a little curious, what's swinging?"

Just then everyone at the table burst out laughing, wondering at how it was possible Wayne didn't know what swinging was.

"Patrons: Well my good sir, swinging is where you and your wife meet other couples and have sex and if it's something you both like then it could become regular. One thing I will say is, seeing as you don't know what swinging is then you may want to try being a cuck first and before you ask, a cuck is someone that watches his wife get fucked by another man solely for both their pleasures that way it's not considered cheating if you allow it and your wife participates."

"Wayne: woah that seems like a lot, and you guys have tried it?"

"Patrons: Plenty of times, my wife loves it and only has sex with other guys when I'm around, it keeps the marriage healthy, why don't you and your wife give it a go?"

"Wayne: Hell no, she'd never go for it."

"Patrons: By you saying that it gives us the impression you thought of it, give it a few days and maybe you'll change your mind, well we better head off, it was nice meeting you."

When they left the table Wayne couldn't shake the thought of swinging or becoming a cuck and he couldn't help but feel turned on by the thought of it, but came to the conclusion, that it was the beer making him think that way and before his work colleagues noticed his erection he told them he was leaving.

On the drive home the thoughts kept coming back of watching Jennifer getting fucked by another man and the more he thought about it, the more he got turned on. As he pulled into the driveway, all he could picture was fucking Jennifer and decided he was going to take her where she stands to get the release he needs.

When he walked in the door, Jennifer was standing in the kitchen in a satin nightgown with the fabric clinging to her ass and without hesitation and a little liquid courage Wayne went right up behind Jennifer and bent her over the counter top.

"Jennifer: Wayne what the hell are you doing."

"Wayne: Shut up bitch I'm taking what's mine."

As he had Jennifer bent over he lifted up her nightgown pulled her panties to the side and started eating her pussy from behind sucking all of her juices causing her to grab his hair and shove his tongue further into her pussy, just then, Wayne stood up, unbuckled his pants and shoved his full erect 6inch penis into her pussy but because he was so erect he knew he wasn't going to last long and the more he pumped into her the closer he got to exploding.

"Jennifer: Fuck, yes that's it baby, pull my hair don't stop, fuck my pussy, fuck it."

And without warning to Jennifer, Wayne exploded in her with his most powerful orgasm yet but the feeling was short lived.

"Jennifer: What the fuck Wayne, are you finished already?"

"Wayne: Yea, is that a problem?"

"Jennifer: Ofcourse it's a problem, yes it felt good, but the least you could do is finish me off as well, what got into you anyway?"

"Wayne: I was at the pub after work and met some guys that were telling me about this swinging thing or becoming a cuckold."

"Jennifer: What are those, and why we're they the cause of this."

"Wayne: So basically swinging is where a couple would go out and meet other couples and swap partners and indulge in meaningless sex but they said seeing as I haven't done that, I should start with being a cuck first which is someone that watches their wife fuck another man but it wouldn't be considered cheating as you'd have my permission to do so and it can only be done in front of me and after picturing it, I guess it turned me on."

"Jennifer: So let me get this straight, do you mean to tell me, you want to watch me fuck another man?"

"Wayne: Oh definitely not, it was only a thought is all."

Jennifer started thinking to herself, "I could never let another man fuck me, my body is Wayne's only, what would our daughter think of it, could this mystery man last longer than Wayne."

"Jennifer: Fine, I don't want you touching me for the rest of the night."

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

For the next few nights nothing happened, not a hug, an I love you, not even a kiss just pure silence. Jennifer noticed over those few nights, Wayne's behaviour was changing like he was actually considering it, becoming a cuck, but deep down so was Jennifer and the more she thought about it, the more she knew tonight was the night she was going to convince him to make it be his decision.

When Jennifer and Wayne got into bed she took off her panties and bra, got between Wayne's legs and started sucking his cock.

"Jennifer: You like it when I suck your cock like this?"

"Wayne: Yes my love."

"Jennifer: Do like watching me shove your cock down my throat?"

"Wayne: Yes my love."

"Jennifer: Ok, keep your mouth shut because I'm about to ride your cock."

When Jennifer got on top she looked into Wayne's eyes and could see the feeling he loved of entering her pussy and knew this moment may have been her only chance.

"Jennifer: You love watching me ride your cock don't you?"

"Wayne: Yes."

"Jennifer: How would you like to watch me ride another man's cock."

"Jennifer: Ooh someone's getting turned on, have you sitting in a corner watching another man's nice hard cock glide in and out of your wife's mouth making her a little whore."

"Jennifer: Do you want to watch your wife fuck another man?"

"Wayne: Yes, I want to watch another man fuck my wife."

"Jennifer: That's a good boy I knew it, now cum for me."

"Wayne: Mmmm that's it, milk my cock, with your pussy."

Even though Jennifer didn't get to orgasm, she was still satisfied her plan was going to work.

After a few days passing, the thoughts of another man had left Jennifer's mind, that was only until Wayne bought it up at dinner.

"Wayne: So I've been thinking, if you were being serious about fucking another man, would you like to start looking?"

"Jennifer: You've got to be fucking kidding Wayne, you're actually considering watching another man fuck your wife, I'm nothing but faithful and have kept my vowels since the day we married."

"Wayne: my love just hear me out, it'll only be once and I'll be there."

"Jennifer: I'm not some sort of fucking toy you can just pass around."

"Wayne: Please my love just this once and that's it."

"Jennifer: Pump as much cum as you can into my pussy and eat me out."

"Wayne: That is disgusting, I'm not going to eat my own cum out of you."

"Jennifer: Do you see where I'm going with this, you want me to do something disgusting, in order for me to do that, you must do what I asked for me."

And with that, Jennifer got up from the table and made her way to their bedroom to see if Wayne would take the bait. First she got completely naked, dimmed the lights and spread her legs.

10 minutes later as she wait, Wayne walked in and without hesitation, started fucking Jennifer crazy and she was surprised to say the least at the amount of stamina he had and she began to enjoy it, but that fantasy was short lived and he came not long after but just as he was went down to eat her out, she spoke up.

"Jennifer: hold on the there Mr get on your back, I'm going to ride your face, so you can suck every ounce of cum."

"Wayne: Hurry up then before I change my mind."

Just then Jennifer straddled his face and grabbed a fist full of hair shoving his mouth to her pussy as he started sucking her pussy lips and taking all of his own juices. She was enjoying every second of it that much, she was riding his face even harder, then out of no where, along with his cum being sucked out she had reached the best orgasm that she could remember with her juice running down his chin and the second she did that her hips started bucking and within minutes she laid down on her back and was fast asleep.

When Jennifer woke up laying naked, she looked next to her, and Wayne was no where to be seen and she could hear noises coming from the kitchen so she got up and went to check it out. When she got there in her nightgown, Wayne was cooking breakfast and Jennifer could feel herself getting horny because waking up to breakfast being cooked felt like a thing of the past.

As she walked up behind him, she pressed her tits into his back, reached into his boxers and started stroking his cock.

"Wayne: Ooh what's gotten into you this morning, I take it you had a good night."

"Jennifer: mmmm I had an amazing night, now turn around and face me."

Without even hesitating Wayne turned around, Jennifer dropped to her knees and started sucking Wayne's cock like never before. Wayne grabbed the side of her head and started fucking her mouth, causing massive amounts of saliva to come from Jennifer's mouth as she gagged and to Jennifer's surprise, Wayne wasn't cumming.

Sucking his cock wasn't something Jennifer always did but in that moment she was loving it because he was lasting and for that small reason she was contemplating on not going through with fucking someone else as her tongue was running along the bottom of his cock.

"Jennifer: Am I sucking your cock good enough my love?"

"Wayne: It feels fucking amazing, can you swallow my load."

"Jennifer: Ofcourse I can my love when ever you're ready."

As Jennifer was slobbering over his cock, stroking his shaft at the sametime sucking his mushroom head knob, she could feel him about to cum, so she got ready.

within seconds he was spurting out rope after rope of cum directly down her throat and she was swallowing like a champ.

Just then she stood up and said.

"Jennifer: Did you enjoy that my love."

"Wayne: I truly did baby."

"Jennifer: I know we made a deal my love but do I really have to go through with having sex with another man?"

"Wayne: after what you made me do lastnight, yes, the deal still stands."

"Jennifer: Baby just think about it properly please, my pussy is yours and yours only, I don't want to cheat."

"Wayne: It's not cheating my love I'll be right there."

"Jennifer: I can't do it my love, my body is yours only."

"Wayne: We made a deal and that's that, no backing out and plus, it'll be one time only, I promise."

"Jennifer: Do you really mean that my love, one time only."

"Wayne: Yes I promise, once you and whoever we choose have sex where his cock has been in you, that's it."

"Jennifer: whoever we choose?"

"Wayne: Yes my love, whoever we choose, why I say that is because if you're going to be the one to fuck him, you should atleast have some input, I don't want you fucking someone who looks dirty."

"Jennifer: Well I guess I should be saying thank you, even though I don't want to do it."

Once that conversation was done, Jennifer and Wayne had breakfast then went on with their day having no interaction at all but as the night was drawing closer Jennifer decided to make one last play at not going through with it because she generally didn't want to do it, but, unfortunately for her, her request fell on deaf ears.

"Wayne: My love, I'm going to set up the ad now, would you like to join me?"

"Jennifer: I'm ok just let me know when it's done."

When Jennifer left, Wayne got to starting the ad with a picture of Jennifer in her nightgown wearing no bra or panties to where you could see her nipples poking through and also made a fake email for guys to send messages through to. The moment Wayne had in his head what he wanted to say the ad read.

**********

- Husband and Wife looking to explore Cuckold.

We are a married couple that are wanting to widen our variety of experiences by giving one lucky man the opportunity of having sex with my beautiful 46 year old wife pictured whilst I watch. As this is our first and only time, we are looking for someone that is experienced in making men a cuckold and can take control, but also someone that can stick to a plan of making it happen and won't back out because it's something we both want.

My Wife has an amazing set of tits that she loves being sucked and has every guys head turning the way she walks and is up for most things but more details can be spoken about when we get to chatting, so if this sounds like you then please send us a message my name is Wayne and my wife is Jennifer.

***********

"Wayne: The ad is all done my love now it's just time to wait for replies."

"Jennifer: Do you think we will get any replies."

"Wayne: Ofcourse we will, any guy would be lucky to fuck the lady I married with my permission as I watch."

30 minutes later as they we were watching TV, all Wayne and Jennifer could hear was a ding noise constantly going off, at first they thought it was the Show but later came to realise it wasn't. So Wayne got up and followed the noise to see where it was coming from and the noise lead Wayne to their room. When he got in there, there was notification after notification of people sending emails in reply to the ad he put up, so he quickly called out to Jennifer and she came running to the room asking what was up.

"Jennifer: What's going on?"

"Wayne: That noise is coming from men replying to the ad."

"Jennifer: What does it say."

As she hadn't read the ad yet Jennifer sat down and started reading and when she got to the end her eyes went wide and the first words that came out of her mouth were.

"Jennifer: Don't you think that makes me sound like a cheap slut?"

"Wayne: ofcourse not, but like it says other things can be discussed to the potential meeting, but you've got to look at it from my perspective, I'm willing to sit there and watch and have another man fuck you, that's gotta count for something."

"Jennifer: Well you don't have to say it as though I'm some form of property but it's ok I trust you."

Wayne and Jennifer sat at the computer for atleast an hour because as they got close to the end of reading each one, more just kept popping up and it seemed like they were never going to end. Eventually the emails stopped and most of them were filled with the same nonsense and never really stuck but they did come across 3 emails that sounded interesting, so they slept on it and Wayne told Jennifer she could choose who her suitable mate could be when they woke up.

When Wayne woke up in the morning he was surprised to see Jennifer wasn't in bed, but better yet she was one the computer.

"Wayne: my love, what are you doing?"

"Jennifer: I'm going through the 3 potential choices."

"Wayne: Have you picked one?"

"Jennifer: Yes, I have."

"Wayne: Ok, which one."

"Jennifer: Frank."

"Wayne: Why him, isn't he the youngest out of the 3?"

"Jennifer: Yes, I understand and get that he's only 29 but the reason I chose him was not because of his age, but because he's only messaged once."

"Wayne: So you're only choosing him because he only messaged once, you'll have to explain a little more."

"Jennifer: Well the other 2 have kept messaging non-stop and their message just got a little to graphic, so that's why I chose Frank."

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

- Frank's reply

Dear Wayne

I have read through your ad a few times and I believe that I could be the man you and your beautiful wife are looking for, I'm not going to bombard you with constant messages I'm just going to let you know that I'd be interested in helping and to make the situation more comfortable, we could meet in person and get to know eachother first.

Yours Sincerely Frank

***********

That very morning Frank was sitting at home anxiously waiting on the computer wondering if he'd get a reply or just be completely ignored.

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

Dear Frank

Upon reading your reply to the ad, my wife has decided to accept your offer and has requested a picture of yourself to seal the deal.

Yours Sincerely Wayne

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

When Frank read the reply he started getting all excited that he took his shirt off stood in the mirror and snapped what seemed to be hundreds of picture and over the next 20 minutes he was deciding which one to send.

Now Frank stood at 5'9 with an athletic build, he wasn't the most good looking in the world but what he didn't have in the looks department he made up for in the bedroom.

Without giving it a second thought, Frank sent the picture.

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

"Wayne: The picture is here my love."

"Jennifer: Woah he's not the best looking but he definitely does look clean."

"Wayne: should I ask him for a picture of his cock so you can see what you're getting yourself into?"

"Jennifer: You can if you want but I don't really care because it's only happening once."

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

Dear Frank

I hope it's not to much to ask but I was wondering if you could send a picture of your cock for my wife to see.

Yours Sincerely Wayne

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

Dear Wayne

As much as I'd love to send a picture of my cock I'd feel more comfortable of her seeing it in person so we all know that this is real. In saying that, if this is real, meet me at the 93 Spade Cafe at 3pm tomorrow, there's no need to reply after this message, just know that I'll be there waiting at 3pm.

Yours Sincerely Frank

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

"Wayne: Ok, so Frank said no to the picture of his cock but, he did say that he wants to meet us at the 93 Spade Cafe at 3pm tomorrow so that we all know this is real and that if you want to see his cock it'll be in person."

"Jennifer: Ok, I'll make sure I'm ready for it by tomorrow, but just for one last time, do I have to do it because I don't want to."

"Wayne: Yes you do, we had a deal."

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

As the day went on Frank was sitting at home contemplating what to say or even bring up when he meets Wayne and Jennifer, how would he introduce himself but the more he thought about it, the more he was drawing a blank at the fact he was going to fuck another mans wife as he watched. The truth was, Frank knew he had no experience but because it had gone the way it had, he now had to fake it but to get a fair idea of what a cuckold was he had to research it.

He found out from reading online there were many ways of a husband being a cuckold but the one that was most common was where the husband was humiliated, it wasn't franks nature but he had to be confident and using that type seemed like his best bet.

The day and night had passed quicker than Wayne, Jennifer and Frank could've anticipated and before they all knew it, it was 2pm only an hour away of them meeting.

Frank left his house at 2pm and got to the Cafe at 2:30pm which gave him enough time to get rid of his nerves. At 2:50pm Frank noticed a car drive past slowly and due to the picture in the ad he saw who he could only assume to be Jennifer.

5 minutes later, he realised he was right, he could by now see Jennifer and Wayne walking towards him, so he quickly stood up Gave Jennifer a hug and pulled a chair out for her.