tagLoving WivesWedding Night Cuckold Ch. 01

Wedding Night Cuckold Ch. 01


Author's note: this is a story in the "cuckold humiliation" genre. If this isn't your fetish, skip this one.


"This place is incredible," Olivia said as she walked from room to room. The house was indeed a sight to behold: roof-top terrace, a gorgeous view of the city, marble countertops, outrageously large and beautifully landscaped. Olivia could not help wondering how Emily and Richard, who always seemed to struggle financially, were able to afford it.

"How ever did you manage to buy this place?" Her husband James must have had the same thought.

"Well..." Strangely enough, Emily seemed a little discomfited by the question. After a short pause, she motioned them to a nearby sofa. "Let's sit down."

"I haven't told this to anyone," she began after seating herself across from them. "It's just that -- well -- I heard the two of you have some problems with debt?"

James and Olivia shared an uncomfortable glance. They had both taken out six-figure loans in the process of getting their MFAs. At the time, it seemed as if the credentials and connections would be worth the hefty price tag. Now, several years later, with neither of them making any headway towards worldly success - Olivia's paintings were not selling much and James' novel was rejected by several publishers - that decision looked a bit foolish.

At the very least they had each other, having met in one of the seminars the program required the incoming students to attend.

"Yeah," James said after a long pause. "To tell you the truth, we've been thinking of moving in with my parents back in Kansas."

Emily nodded. "I'm just going to come out and say it," she said, taking a deep breath. "I was paid" --- she named an amount of money that sounded enormous, obscene even -- "to cheat on my husband on my wedding night."

"My God," Olivia blurted.

"Holy shit," James said simultaneously.

The two of them had been at Richard and Emily's wedding only a month ago. James remembered how elegant Emily looked in her wedding dress, almost chaste even. Tall, with an athletic frame and long black hair which she usually kept in a bun, Emily was gorgeous. James' cock tingled at the thought of her fucking a stranger on the very same day they had seen her get married.

Olivia had been a bridesmaid at the wedding and Emily was set to return the favor in a months' time when James and Olivia would finally tie the knot. Though he was quite enamored with his wife -- Olivia's beauty was almost the opposite of Emily's, with wavy straw-colored hair and large breasts that always seemed to fill out whatever it was she was wearing -- Emily made regular appearances in his fantasies. He was particularly fond of imagining the two of them servicing him together....

"How could you do that to Richard?" Olivia sounded to be in a state of shock.

"Richard knew all about it," Emily replied calmly. "He was there, watching the whole time."

Olivia gasped but said nothing. With her mouth hanging open, she seemed to be rendered speechless.

"Neither of us regrets it," Emily continued. "It was a very large amount of money, you know." She shifted her gaze from Olivia to James and back. "The house is a nice perk but more important is the the ability to pursue the careers we chose. You know yourself how hard it can be."

Like the two of them, Emily and Richard were trying to make it in the art world. The four of them had all met at the same MFA program.

"I'm sorry if I shocked you," Emily said. "Do you want to hear more or shall I drop it?"

"It's just so unexpected," James said.

"It is," Olivia chimed in apologetically. "We don't mean to be judgmental. We're your friends. You should tell us."

Emily nodded. "You might remember the man from the wedding. An slightly older gentleman by the name of Trevor Montgomery?"

James vaguely remembered the man. Early 50s or thereabouts, bulky, firm handshake, he spent most of the evening talking to Emily's parents. He barely registered on James' memory of the wedding.

"Mr. Montgomery is a very wealthy man who enjoys...this sort of thing. We're not the first couple he had persuaded to agree to something like this."

Emily paused.

"Once everyone had left, he came up to the bridal suite with us. It started off very awkwardly. I chatted with him aimlessly about the wedding as Rich made us drinks. Eventually, Mr. Montgomery just put his hand around me and brought my lips to his own."

Olivia could not restrain herself. "Rich just watched you kiss this man!?"

"He did," Emily met her friend's gaze. After a moment, Olivia's outrage subsided and she began to feel sorry.

"I didn't mean to be rude," she said. "It's just that..."

"I understand," Emily said. "Yes, my husband watched me make out with another man. I'm sure it wasn't easy for him, to watch me kiss this stranger right in front of him. Not only that, Mr. Montgomery ran his hands all over me as we made out, fondling my ass and boobs.

"This went on for a few minutes. Afterwards Richard undressed me. It's one of Mr. Montgomery's fetishes -- he wanted my husband to undress me and present me to him.

"Rich fumbled with my wedding dress for a good long while. When he finally lowered it to the floor, my first instinct was to cover my breasts with my hands. Mr. Montgomery smirked when he saw it and it occurred to me too how ridiculous it was.

"Still I was so embarrassed to be standing there, half-nude, in front of this man, on my wedding day of all times. It seemed like forever until Rich took off my stockings and shoes. Finally, my husband lowered my panties to the floor and I stepped out of them. He took my hand and brought me over to Mr. Montgomery, putting my hand in his."

"Jesus Christ," Olivia said. It was a little too much. She looked at her husband. "Could you do something like that?"

"What happened next?" James ignored his wife's question.

"Well..." Emily paused. "I have to explain that Mr. Montgomery is a very dominant man. Throughout the evening, he seemed to delight in humiliating Rich a little. Once I was completely naked, the first thing he wanted to do a cock-comparison picture."

"A what?" Olivia asked.

"He undressed and told Richard to take off his clothes as well. Once they were both naked, he had me stroke both of their cocks before taking a picture of me with a cock in each hand."

"Here," Emily said and handed James her phone. Trying to steady his hands, James took the phone. Olivia looked faintly repulsed but leaned over and they both huddled over the small screen.

The picture showed Emily completely naked, although, because it was taken from above, only her breasts were visible. They were c-cups, looking firm and perky; definitely not as large as Olivia's, James thought, but fantastic nonetheless. He had never seen his wife's friend naked. He imagined cupping them.

There were indeed two cocks in the picture, both held by Emily. The contrast between them was as stark as could be. The first was as thick as can, whereas the second resembled nothing as much as a carrot; the first was long and meaty, whereas the second seemed to be only half as large. Emily seemed to be almost enthralled by the first one.

"Holy shit," Olivia exclaimed. "That's a huge cock."

"Isn't it?" Emily smiled. "Yes, Mr. Montgomery turned out to be very well-endowed." She leaned over and looked at the picture. "I was happy to see that Rich was fully erect too. At least he was enjoying the proceedings in his own way. Still, even at full-mast he was no match for Mr. Montgomery."

"I've never seen one this big," Olivia said, seemingly mesmerized by the image.

Emily smiled again and cast an appraising look at the bulge on James' pants.

"Yes, it was quite enormous," she said, taking the phone back.

"What happened after you took the picture?" James was eager to change the subject.

"Mr. Montgomery laid me down on the bed and pulled my legs apart. He motioned to my husband behind him. Rich's job -- poor thing -- was to hold my legs in the air as I was being fucked. Mr. Montgomery wanted him to have some part in the proceedings."

"My God," Olivia said.

"And then he started sliding it into me..."

"How did you even take it?"

"It hurt at first," Emily admitted. "The first thing I felt was pure pain. I've never had anything that big in me. But after a little while I got used to it. Honestly it felt amazing. Its just...I don't even know how to say it...I've just never been filled like that before."

"Did you come?" Olivia gave her friend a tell-me-the-truth look.

Emily blushed. "Yes," she said a little sheepishly.

"Wow," Olivia said.

James noticed his wife's voice lost the harsh tone of condemnation she seemed to have earlier. He even thought he could discern a note of envy; then again perhaps he was imagining it.

"I came so many times," Emily went on. "When Mr. Montgomery started pounding me, I became livid. I never screamed so much before. In between the 'ooh' and 'aah's, I kept yelling for him not to stop. When he called me a whore, I told him I was his dirty slut and that he could fuck me whenever he wanted. I would have said anything to keep his dick in me.

"I came after only a minute of having him inside of me. It was very embarrassing because I ended up squirting my juices all over him. I never squirted before. When my orgasm subsided, my first impulse was to apologize to Rich. I looked my husband in the face -- he was blushing very hard and looked a little devastated even as he kept on dutifully holding my legs apart -- and said I was sorry, very sorry. I'm not sure if that made it better or worse."

Emily looked away. "I never quite realized what I was missing until my wedding night. Ironic isn't it?"

"I'm afraid it was very hard for poor Rich," she continued after a slight pause. "But I couldn't help it, you know?"

She searched Olivia's eyes for some flicker of sympathy and James was a little miffed to see his wife nod understandingly.

"Anyway Rich enjoyed it too," Emily said defensively now. "He must have. He was very hard the entire night."

"All I can say is that it was a wild night," she went on. "I lost count of how many times I came. Rich came many times too, though he wasn't allowed to put his dick in me. That was part of the deal -- only Mr. Montgomery could fuck me on my wedding night.

"But Mr. Montgomery was very nice and always made Rich a part of things. He had the two of us make out as he took me from behind. Or he fucked me sideways while my head was resting on Rich's lap. Things like that. Rich masturbated rather furiously through it all."

Emily looked at them uncertainly.

"Anyway," she said, "That's the gist of it."

"Wow," James said, not quite knowing how to reply. His dick was painfully erect.

"And you're happy with it all?" Olivia sounded incredulous.

Emily nodded. "The money was very good. Both Rich and I came so many times. I guess we both enjoyed it in different ways."

She looked back at the couple. "I told you all this because your wedding is coming up. Do you think you might consider something like this?"

"Hell no," James said.

"My god, never," Olivia answered simultaneously.

Emily smiled. "I guessed as much, but thought I'd ask anyway. If you change your mind, just let me know."


"Can you believe what we just heard?" Olivia asked as their car pulled out of the driveway.

"Yeah," James replied. "Holy shit."

"I just don't understand how her husband could be okay with that," Olivia said.

"No clue. I'm totally speechless." In truth, James was still painfully erect, his mind swimming with thoughts that made ordinary conversation near impossible. He couldn't wait to get home, when he could excuse himself and have a discreet wank somewhere private.


After watching the couple drive away, Emily pulled out her phone and dialed her husband.

"We are well on the way to picking up that bonus."

"It went well then?"

"As well as could be expected. They were shocked of course. But their wedding is not for a month. I think they'll come around."

"You sure?"

"Olivia's always had a thing for big dicks. She's very prim and proper these days but I think a few stories of our wedding night will bring out her inner slut."

"As for James, I used his computer a few years ago, and took a peep at what he had on there...there was a lot of cuckold porn."

"Still," Emily continued thoughtfully, "he might need a little more persuading." She paused for a moment. "Speaking of which...Mr. Montgomery called today."

There was a silence on the line.

"Oh?" Richard said neutrally.

"He offered us a half as much for a repeat."

"We don't need more money."

"We don't," Emily agreed. "Still, it'd good to have. We could buy a beach house. Besides..."

She paused again.

"...shall I tell you what he has in mind?"


"Where are you?"

"Driving on the highway."

"Take out your cock then."

There was a sound of a zipper coming undone.

"This time he wants to fuck me while I'm wearing my wedding dress. You'll get to be the one holding it all up as he's thrusting into me."

There was no reply except the sound of some labored breathing.

"He also said he wants to take me doggystyle while I look into your eyes. He wants me to tell you how much better his cock is compared to yours. Thicker. Longer."

"That sounds awful," Richard said.

"Are you touching yourself?"


"He said he's going to fuck me very roughly this time," Emily went on. "He said he will do whatever he wants to me, call me all sorts of dirty names, spank me, use me however he wants. We'd have to agree for me to be his total slut for the evening, no holds barred."

Richard didn't reply but Emily could hear the sound of his hand pumping his dick.

"Shall I tell him we'll go for it?"

There was some more silence. "One condition."

"Yes dear?"

"If Olivia and James go for it...then I want to fuck her too. It doesn't have to be on their wedding night. But I want to fuck her."

Emily gasped.

"You want to make love to Olivia?"

"She's very pretty, isn't she?"

"She is," Emily said. It felt strange to be having this conversation, to talk to her husband about another woman he wanted.

"I've always wondered what those breasts of her look like up close. They have to be enormous."

It was hardly fair for her to deny her husband this, especially given what he went through -- and would go through -- if they agreed to Mr. Montgomery's new proposal. She felt a pang of jealousy though, imagining Olivia's big milky tits wrapped around her husband's cock.

"I don't want to lose you," she said into the phone, unable to control herself.

She did love Rich, more than anything. She had never cheated on him before their wedding night; and if he had told her that under no circumstances were they to agree to Mr. Montgomery's proposal, she would have gone along without question. She simply thought they could have it all, love, money, wild nights of sexual submission.

"How can you even worry about that?" Richard said reproachfully. "You know nothing will drive us apart."

Emily took a deep breath "Okay," she said, a little calmer now. "I'll call Mr. Montgomery."

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by Anonymous

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by Anonymous05/14/18

One of the Best Stories on here

Love this story - desperate to read the next chapters. Really hope you return to writing on here soon.

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by Anonymous05/01/18

More cuckold crap!

The vast majority of male readers (> 99%) hate cuckold stories. So why do you waste your time writing them!

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by newtype252512/01/17

loving this but needing more chapters!

Really dig the story and would love to read more but you went away... Here's hoping you make a comeback!

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