Cuckold Husbands Regret Ch. 01

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"Frank: yup correct."

"Wayne: Thank you, I'll let her know."

*10 minutes later*

"Wayne: My love I have a surprise for you."

"Jennifer: What would that be."

"Wayne: I just spoke with Frank and he's going to train you again if you're up to it."

"Jennifer: Yes yes yes, thank you my love."

"Wayne: But there's a catch, once you've finished your period, he wants me to drop you off to his house for 3 straight days of training before having a 2 day rest before having sex with him."

"Jennifer: Wait so I'll be staying at his house for 3 days of training, will you be there?"

"Wayne: No I won't because thats my punishment for cumming."

As Wayne predicted, the next couple of days came and went and it was time for Jennifer to be dropped off for training but Wayne was glad to be alone because that way he could masturbate and cum and not feel guilty. Wayne was going to be dropping Jennifer off first thing the morning so she'd be able to get in a full first day of training.

As they arrived, both Jennifer and Wayne walked to the front door and knocked then patiently waited for Frank.

"Frank: Jennifer I'm glad you're here, go into the training room and wait for me."

"Wayne: Can't I give my wife a quick kiss goodbye?"

"Frank: No."

"Jennifer: Just leave cuck I'll see you in 3 days."

"Frank: Well, you heard the lady, we'll see you in 3 days."

When Frank said that he closed the door in Wayne's face which didn't make Wayne to happy and actually started making him angry so he stood there knocking on the door demanding to see his wife to no avail so he left.

Once in the room, Frank ordered Jennifer to strip, she was hesitant at first but gradually did as she was told because in her mind she was there solely for training and felt this was a part of her training.

"Frank: So Jennifer, do you have any questions before we begin?"

"Jennifer: Uhm where will I be sleeping?"

"Frank: You'll be sleeping with me in my bed."

"Jennifer: But isnt that crossing a line, I thought I was only here for training."

"Frank: You're correct, you are here for training but because of your husband breaking the deal, this is an addition to it and before I forget, even though the training may be intense there will be pleasure, because I've decided to go up to the final sized dildo for the 3 days."

"Jennifer: Should I be worried about the size?"

"Frank: Yes and no but, you're here to be trained so you can either call Wayne up now to get you or you can see it through."

"Jennifer: I'll see it through."

"Frank: Ok, your training can begin, but before you get put in the chair, pull my cock out."

Jennifer got on her knees and was amazed when his cock sprang to life, she was mesmerised to say the least and actually felt as though she missed it. Jennifer began to slowly stroke his cock adding some spit so it could enter her mouth easier, when that was done, Jennifer knew her assignment and began to work his enormous cock in her mouth and doing it as she pushed the thoughts of Wayne's small cock out of her head, legally she was married but right there and then she was single.

"Frank: Mmmmm that's it baby suck my fucking cock like a good whore."

"Jennifer: Thank you for giving me another chance with your cock."

"Frank: That's ok baby, just keep sucking."

Jennifer felt herself becoming aroused as his slick cock had her mouth wide open and going in as far as it could.

"Frank: That's enough sucking my cock for now, it's time to begin training."

"Jennifer: Just a little longer please, can I make you cum."

"Frank: Ok, but make it quick."

At that point she felt as though she was possessed by some kind of cock craved demon because she started gagging and stroking Frank's cock as fast as she could just to make him cum and to Frank's surprise it was working because 2 minutes in as he stood, Frank's legs started to spasm and his cock exploded all over Jennifer's face and tits and by her facial expression she was enjoying it all.

From the beginning of Wayne and Jennifer's marriage, she felt all the things they explored sexually were enticing and adventurous but on her knees in front of a younger man covered in his cum, she now knew that was not the case.

"Frank: Ok now stand up so I can strap you into the chair."

Without question she did as she was told.

"Frank: Now today you will have 2, 1 hour sessions they're going to start off slow but will speed up as the hour progesses."

Before putting the dildo machine in her, he sat down on a chair in between her legs with her pussy on full display and began rubbing her clit. The more he rubbed the more she got turned on because it had been so long since she got any type of feeling like this from Wayne and she didn't want it to stop.

"Frank: Are you ready for the dildo baby."

"Jennifer: Yes, fucking put it in me."

Now words after that were said until the tip touched Jennifer's pussy hole because as the dildo entered she screamed at Frank to take it out but there was nothing she could do as she was strapped down.

"Frank: you wanted the dildo in you and that's what you're getting."

He then proceeded to put it on a 1 hour timer so once that 1 hour was up it'll shut off itself.

"Frank: Calm down, baby it's going to get better I promise, like I said, it'll start off slow."

Taking his word for it, she bit her lip and took it, the pain she was feeling slowly started to subside the longer it went on and as it got faster she was hit with wave after wave of orgasm. The whole time Jennifer was squirting, Frank sat next to her pinching and sucking her nipples sending a shock wave of pleasure through her body, she was actually taking it better than Frank first anticipated but he guessed it would've been due to previous training days.

"Frank: How are you like it?"

"Jennifer: It's so, argh, fucking good."

"Frank: That's what I like to hear, you've done a good job, but your first session for the day is almost over."

"Jennifer: Already?"

"Frank: Yes baby, unfortunately, don't worry next thing you know, you'll have my cock in you."

When she was done, once again, she couldn't get up, so Frank thought ahead and made her a nice warm bath and even though it was day time it was still cold. When he picked her up she asked him.

"Jennifer: Where are you taking me?"

"Frank: I've just made you a bath to clean yourself up and wash the cum off you."

"Jennifer: Really, you didn't have to do that for me, I didn't mind having your cum on me."

"Frank: It's ok, you can have more on you later if you'd like?"

"Jennifer: I'd like that."

"Frank: Ok, even though you're here for training I still want you to know I'll take care of you."

"Jennifer: I wish my husband was like you, he hasn't done things like this for me in so long."

When Jennifer was in the bath Frank washed her face and tits clean of his cum then picked up the courage and kissed her. She repayed him by kissing him back and instantly there lips were locked in passion as his hand made its way to her pussy.

Like in the room, he began to rub her clit ever so slowly having her arousal spike at the same time poking her pussy.

When she was done in the bath, he got her out dried her off and assisted her to his room as she was able to walk a little. As they lay down he put on a movie and they both fell asleep as if they had been going all night.

Jennifer woke before Frank and looking at the time it was getting late so she woke up Frank and asked him to be trained. The process was repeated followed by a bath and back to bed and just like that Jennifer thought to herself that the first day was already over but little did she know Frank had a surprise for her.

In bed he went under the sheets and started licking her inner thighs giving her a tingling sensation that she had never felt before. As his tongue skimmed across her clit she let out a small moan as she rubbed his head.

"Jennifer: That's it baby keep licking my pussy, make it feel better after stretching it for your cock."

He then stopped moved up her side and aggressively started finger banging her as she grabbed him.

"Frank: Who's pussy is this?"

"Jennifer: It's your fucking pussy aaaaaargh I'm gonna cum fuuuuuuuck."

As her orgasm subsided Frank's fingers were dripping as she was covered in sweat from the exchange, so he moved his hand up her body grabbing her tits and squeezing them.

"Frank: How do like being stretched?"

"Jennifer: It hurts but I'm getting used to it, it feels amazing."

"Frank: what do you feel your husband is thinking right now."

"Jennifer: I don't really care, I'm just enjoying how you're making me feel."

As the feeling in the room calmed down Frank and Jennifer slowly drifted off to sleep naked with his cock nestled in Jennifer ass crack.

The next day was Jennifer's relaxing day, the feeling in her legs was a little better, her and Frank even went out to lunch together and took some pictures of them and sent them to Wayne.

"Jennifer: I hope you like the pics cuck, 1 more day to go and I'm yours again."

"Wayne: You're mine? In the photos you're acting like his."

"Jennifer: Well I am his for 3 days I don't see the big deal, it's your fault I'm here anyway."

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

"Frank: What's wrong?"

"Jennifer: Nothing really I just sent a picture of me and you to Wayne and I think he got jealous."

"Frank: He needs to calm down, there's one more day of training, me and you are having sex once and yous won't see me again."

When Frank said that Jennifer's expression changed because she knew once this whole thing was over with, her sex life and marriage were never going to be the same. When they were home they just lounged around watching movies for the rest of the afternoon and night.

Once morning came Frank was awoken to the surprise of Jennifer sucking his cock.

"Frank: Ooh baby what did I do to deserve this."

"Jennifer: Well I go back to my husband tomorrow so I wanted my last day here to be good, so what better way to say thank you than to suck your fat cock and attempt to swallow your cum."

"Frank: I might not let you leave, if this is what I'd be getting."

"Jennifer: Well I do have your number so I can always text you."

"Frank: I can't wait to fuck and stretch your pussy, I want it so bad."

"Jennifer: When we have sex, it's your pussy."

"Frank: Are you ready to swallow?"

"Jennifer: Yes baby give it to me."

She then swallowed a large amount of it but still had cum dripping down her chin and for some reason which Frank did not know, Jennifer got her phone and took a picture.

"Frank: Why did you take a picture?"

"Jennifer: I sent it to my husband so he knows what I look like after swallowing cum."

"Frank: oooh you must want to start an argument with him."

"Jennifer: If it does, I don't care, he bought this side of me out and I love it."

"Frank: Come here and kiss me and slide your wet pussy over my cock."

"Frank: Oh that feels so Good baby, I just want to fuck you right now and not wait."

"Jennifer: I want your cock in me as well but I don't know if we should, the deal was, when we have sex, my husband would be there and if he isn't there it'd be cheating."

"Frank: Is it cheating if we both want it."

"Jennifer: Yes it is, but let me think about it."

When they were done talking they made their way to the room to begin Jennifer's first session of the day. As the dildo was inserted she took it easier than the previous day and enjoyed it sooner than she hoped. Frank just sat there watching her take it, and his cock grew, so he stood at her head and started fucking her mouth in the middle of her training causing her to gag, when he came all over Jennifer, her training was up.

"Jennifer: That's was the best sexual experience I've ever had in my life, I didn't want it to end."

"Frank: I'm glad you liked it baby, I didn't want it to end either, I wanted to put my cock somewhere else, but unfortunately I have to wait."

"Jennifer: You don't have to wait anymore because I've made my decision about having sex with you, but if we do, there's no more training and you have to let me relax for the rest of the day."

"Frank: Ok baby it's a deal."

As the day went on, they knew what was coming but stayed in a warm naked embrace as Jennifer slowly stroked his cock not wanting to let go and when she looked over, Frank was fast asleep. When he woke, he got up and decided to make dinner as the day had gotten away from him after his sleep.

When they were done with dinner and all dishes were done they made their way back to the room where Frank slowly walked towards Jennifer pulling her in ever so passionately and kissing her on her lips. As their lips were locked, Frank took a firm grasp of her ass pushing her against the wall and as much as she didn't want to admit it, she wished her marriage with Wayne had this type of passion and dreaded that she had to go home to somewhere she would never get it again.

"Jennifer: That's enough baby, let me take care of you."

On her knees, she started teasing the tip of his cock with her tongue before putting in her mouth. At the start of the whole thing she didn't even want to think about being with another man but after feeling what she has, it all came as normal.

"Jennifer: You ready to put it in your pussy baby."

"Frank: Yes."

When on the bed, Frank got on top of Jennifer in the missionary position with her legs wide apart and started teasing her by rubbing his mushroom head over her clit sending shocks of pleasure through her body.

"Frank: are you ready?"

"Jennifer: I think so."

As she felt his cock at her pussy entrance, she pulled him in close knowing what was going in her was going to hurt. When his cock head popped in she gasped for air feeling as though she had just been ripped and knew her pussy was never going to be the same.

With Frank slowly moving in and out with only a quarter of his cock, Jennifer started getting used to it and started getting wet but at the same time had a feeling of guilt go through her that she was fucking another man and cheating on her husband, whom with all that was happening, she still loved and had to remind herself it was just sex.

"Frank: Do you think you can take more?"

"Jennifer: Yes but please go slow."

With each movement Frank was pushing further and further at the same time stretching her. At certain points it seemed gruelling for Jennifer but she was committed at that point of adjusting so she began to rub her clit which for her sake was working and the more she rubbed, the wetter she got.

As her juices were flowing, it became easier to accomodate to Frank's size and motion, once she stopped rubbing her clit Frank picked up speed with his thrusts becoming more harder and though she had never had a cock so big, the longer she spent with his cock in her the more turned on she became.

"Jennifer: Fuck fuck fuck."

"Frank: You want it harder baby?"

"Jennifer: Just hurry and fuck your pussy, fuuuuuck, give me that fat fucking cock, my husband cock will never satisfy me like yours."

"Frank: That's a good girl."

All thoughts of Wayne were leaving Jennifer's mind as she was taking most of Frank's cock, she didn't care about being married she just cared about being stuffed by so much meat.

"Jennifer: fuck, you're going to make your pussy cum baby, fuck your pussy fuck it.

"Frank: Who's cheating pussy is this."

"Jennifer: It's your cheating pussy, please don't stop pleeeeease argh fuck.

Her mind felt like it was working overtime confusing herself with all she was saying and all she was thinking. She didn't know what was happening to her, she kept wondering if all she was thinking and saying was because she was enjoying the sex and that if it was all just sex talk but in the moment it just felt right. She knew once she got picked up in the morning that she'd feel something she just didn't know what but for the moment she got it down to what she was feeling, was nothing but pure lust.

Frank was loving every second about drilling this 46 year olds pussy having it get wet all over his cock and he knew he was doing something right. Jennifer on the other hand was purely hypnotised by pleasure and with the aggressive pumps Frank was giving her she came all over his cock at the same time as fidgeting whilst he kept fucking her.

"Frank: You ready for me to unload in my stretched pussy?"

"Jennifer: Slow down slow down, you can't cum in your pussy, that's just pushing it to far."

"Frank: What happened to it being my pussy."

"Jennifer: When we have sex it's your pussy, you've got to remember I'm someone else's wife and after we fuck in 2 days this is over, what happens if I get pregnant."

"Frank: Tell him the baby is his."

"Jennifer: I can't do that and will never do that, he may be a cuck but he's still my husband."

"Frank: And yet here you are being stuffed by another man's cock, so just be quiet and take it."

From that point as she was about to speak Frank then picked up speed once again not stopping the assault on her pussy and once again Jennifer lost all sense of right from wrong and continued to take what she could.

Frank then took his cock out and made Jennifer get on top and ride him pulling her in close as she sat on his cock, and as he held her head down with one hand behind her neck his other hand slid down her back and entered her puckered butt hole before he began his last assault to have her hooked.

"Jennifer: Ouch Ouch Ouch take it out now."

"Frank: You're taking it, don't worry I'm going to fuck you real good."

In her efforts to stop, she tried wriggling but due to the way he held her she couldn't move and had no choice but to take it and after a minute of her pussy taking a pounding she didn't mind and like previous times began to enjoy it.

"Jennifer: Slam this fucking pussy with your cock, give it to me baby I love it."

"Frank: I know you love it baby, I'm almost there."

He then went harder than he had throughout their fucking session causing Jennifer to cum on his cock once again."

"Jennifer: Oh my fucking God I can't take it anymore this is to much fuuuuuck unload your fucking cock in this pussy baby do it, I don't care give me your cum, make it dripping wet."

That was all he needed to hear and pushed Jennifer's ass right down on his cock hitting her cervix and continuously came until his balls were drained. Sitting with his massive cock in her she just stayed there as her orgasm subsided kissing him passionately as they were calming down from the best fucking session they had both had, she didn't want to kiss him but the feelings were just there and the moment felt right.

"Jennifer: Thank you baby that was amazing, i think your pussy is going to need these 2 days to recover."

"Frank: You're welcome baby it's was my pleasure, did you want to go for a shower before bed."

"Jennifer: Yea I might do that, but I'll have one alone if that's ok."

"Frank" ofcourse that's ok baby take all the time you need."

When Jennifer got into the shower her legs felt like jelly after the most mind blowing sex she had ever had in her life and as she felt the cum dripping out of her, she was stunned by the amount coming out and felt proud, she was the one to make him cum that much. As she rubbed her now swollen pussy, she started to feel aroused and got the showerhead pointing it directly at her pussy and as surprised as she was made her cum in seconds.

It got her thinking she was some type of sexual deviant now and wondered if she'd be able to control these urges. when she was done she hopped out of the shower to go to bed and when she got in there, Frank was fast asleep still butt naked and on clean sheet, so she looked at the clock and she was stunned, she was in there for over an hour and for some strange reason, she crawled on the bed, kissed Frank's cock instead of him and said goodnight.