Convincing Kevin Pt. 02 - Finding 5 Lucky Men

Kevin gently woke up from his amazing night of teasing and pleasure at the hands of his wife Katie. He always loved nights when he was allowed to cum, for obvious reasons, but also because Katie usually permitted him to sleep without being in his chastity cage. His small morning hard on and the thoughts of the previous night had him in a great mood. Then he began to recall what he had agreed to in the heat of passion.

He had agreed to Katie's demand that he would find a number of candidates to have sex with her so she could continue to keep him locked up indefinitely as well as enjoy the sexual pleasures she fully deserved and that Kevin could not give her. There was a twinge of regret in the back of his mind as he thought about the realities that lay before him but he also realized how hard his cock was thinking about such realities. The nervous excitement was interrupted by the sound of Katie stirring.

"Morning pussy slut," She grumbled as she stroked his hair. Get me my coffee and then wake me up with that tongue of yours. I am still hot from thinking about all the men you are going to be finding for me."

Without saying a word Kevin got up and obeyed his beautiful wife's command. He made her coffee just how she liked it and as he handed it to her he crawled under the covers and began gently caressing her pussy with his tongue. She could tell how much he loved worshipping her because he would get so close to cumming just from pleasuring her. As he built up the tempo and began licking her more steadily she had to muffle a light, breathy moan so as not to awake the sleeping children. She grabbed her phone and found some porn to help her get over the edge. Katie settled on an interracial gangbang video where the woman was getting roughly used in every hole, sometimes all at once. She imagined being in the center of all of those large cocks and it very quickly put her to the edge. She grabbed Kevin's head with her hand and aggressively fucked his mouth as she began cumming. She held him there for some time before releasing him.

"Thank you for letting me service you Miss Katie," He said to her, genuinely happy to be able to provide her with some pleasure.

"You are welcome Slut. Now you remember our agreement from last night don't you?" She questioned. He nodded. "Good, well I am going to send you my requirements now, I expect you to find five suitable candidates for me by the end of the week. Also put your cage on, that is enough freedom for your little cock." She said devilishly.

Kevin smiled and said "Absolutely Miss Katie," he put on his small metal cock cage and then began getting ready for work. It would be difficult to be productive this week, especially if he had the task of scouring the web for men for Katie.

As Kevin arrived at work he read the email that Katie sent with her requirements. It read:

"Good morning Cucky (boy do I love calling you that already!) I hope you don't disappoint me as much as your penis does. Make sure the men you find meet all of the following criteria:

1. Between the ages of 40-55, I want him old enough to know how to fuck, but not old enough where he can't fuck me multiple times in a night.

2. His cock needs to be 7 inches or larger, make sure he provides proof of this

3. I would like him to be tall and strong, someone who wouldn't have any trouble manhandling me.

4. He must be dominant. I know I let you pretend sometimes but I want to be put in my place by a real man for once.

5. He must be clean of all STD's and willing to provide a recent test. You know how much I hate condoms.

Good luck, if you do well I will give you a surprise!"

As Kevin read the email he felt himself trying to get hard in his cage. He thought to himself, "Hmm I don't think it will be hard to find anyone that wants to fuck my curvy wife, where should I start?"

He had no idea where to start. He could probably find a large number of guys on Tinder but not sure how many of them would be dominant. He googled "How to find bull for cuckold couple" and did a lot of research. He settled on making a profile on Adult Friend Finder. It wasn't like the niche cuckold and bull websites that he found but it seemed to have the largest user base and everyone on the website was looking for sex rather than dating. As with most online dating platforms, it was flooded with way more men than women so the numbers were in their favor.

He answered some basic questions and found a few casual pictures of Katie as well as one tasteful nude photo of her sexy backside just to be sure to attract the best quality candidates. He edited out her face in the photos to remain discreet.

In the bio he wrote: "Looking for a strong, fit, dominant man between the ages of 40-55 to please my wife. Must be at least 7" long, clean of all STD's and local. Must be able to go multiple rounds in a night. Experience as a bull is a plus."

He created the profile, browsed a few random profiles and then waited. Later that night he decided to check his Adult Friend Finder mailbox to see if there was any interest. When he logged on he saw that he had 29 new messages. 29 people wanted to fuck his wife - something he was rarely allowed to do. He instantly felt his small member trying to inflate within the confines of his chastity cage.

"29 new messages from guys who want to fuck you Katie!" He eagerly told her as they were playing around on their phones before bed.

"What? Are you surprised that so many people are attracted to me?" She playfully quizzed him.

"Erm, no, that's not what I meant!" He said defensively.

"Good, just make sure you find the best ones. Don't disappoint me."

Kevin went through the messages one by one and inspected their profiles as well. Some responses were easy to weed out, too old, too fat, cock not big enough. Other replies were too short, he could tell that they wouldn't put forth any effort if they actually did meet the criteria. 9 of them had potential. Kevin carefully selected 5 to send to his wife. All men agreed to show proof of recent STD testing and had no problems cumming inside Katie.

The first one that caught Kevin's eye was a 43 year old personal trainer. His name was Jerome and he was mixed race black and white. He was very fit and said that he "owned" a cuckold couple in the past but they moved away and he had been missing them in the last couple years. He was single and preferred it that way. He owned his own home not too far away. He included a picture of his cock which was a good amount larger than Kevin's. Jerome said he loved bondage and rough sex and claimed he could last as long as he wanted which is something that Kevin was completely unable to do.

The second man that made the cut was a 55 year old black man. His name was Ray and he was very sturdily built, thick and tall. Ray was a blue collar type, said he was a welder and was good with his hands. He had a very large dick that he said was 9 inches and thick and the pictures backed up that claim. He said he had been in the lifestyle for many years an introduced many women to the pleasures and freedom of being a hotwife and loved to show cuckolds what a real fucking will do to their innocent wives.

The third man was a military man. 44 years old, white with a shaved head and a thick brown beard, he looked like he worked out regularly. His name was Rich and although he only had a picture of his cock soft, it was already much bigger than Kevin's was when he was hard. He said he had no experience with cuckold couples, but that he had been doing a lot of research and found the idea very erotic. Rich claimed that he was an expert at making women squirt and that he was confident Katie would be no different. He also said he was very into anal and that he has made many women cum from anal alone. Rich loved to double-penetrate women and if Katie was up to it, said he had a couple hung friends that could join him if she was interested.

The next gentleman that Kevin chose was the youngest of the group. He was a 39 year old man named Jason and very handsome. He was white with short blonde curly hair and said he was a real estate agent so he could schedule free time during the day or night. Jason was looking for a couple for a regular thing. He seemed to be the friendliest and gentlest of the bunch but said he had done this a few times before and now couldn't live without the kink of fucking a married hotwife. His penis was larger than Kevin's and he was uncircumcised. Kevin was unsure what Katie would think of that since they had never discussed if she had a preference. He said he would love to take Katie out for a night on the town before showing her a good time in a nice hotel room.

Kevin was unsure how he felt about Katie going out to dinner with other men. What if somebody saw them together? For some reason he was comfortable letting another man have sex with his wife but had hesitations about it becoming more romantic. He couldn't help but picture them kissing in a dimly lit bar or restaurant while he was at home locked in chastity. The mixed feelings of arousal and shame were very powerful.

The last man Kevin chose to send to Katie was a successful black man from the next town over named Will. Will was a successful businessman and at 49 years of age was the CEO of a small company. He said he was very financially well off but never got married since he was working so hard through his younger years but had more time now that he was set in his career. Will said for the last 10 years he had become very experienced in training cuckold couples and he would love to mentor us. His email stated that he could help Katie in her domination of Kevin and would enjoy spoiling her with new lingerie, nice dinners, and nice hotels. Will did not look like he worked out, but had a dad bod with a big chest, arms, and stomach. He had dark skin and a shaved head and was wearing a nice suit in his photo. His cock looked like it was straight out of a porn movie, and looked to be at least 8 inches long and as thick as Kevin's wrist. Will finished his message to Kevin with a warning, "Once your wife gets a taste of my cock, I guarantee she will never have a need for your small dick ever again. I will ruin her, and I will quickly make her addicted to me."

The thought made him nervous but excited at the same time. He loved pleasing his wife and wanted her to have all the pleasures she truly deserved but he also enjoyed fucking her, even if it was infrequently lately. How serious was Will's warning?

Kevin waited until the following night in bed to send the candidates to Katie. She quietly studied every one of them for what seemed like hours.

Finally she broke the silence. "Good boy. This is going to be a much more difficult choice than I thought. I could imagine myself with all 5 of these men, they are all so hot! My pussy is aching just thinking about it! Get to work while I try to narrow this down."

Kevin slid between Katie's spread legs as she continued to study the laptop screen. She was indeed already slick with her juices and he was able to bring her to orgasm much quicker than he normally was able to.

"Mmmm that was nice. I am still so turned on though. I am not done with that tongue of yours yet, go a bit lower and don't stop until I tell you to." She firmly stated.

Without another word Kevin slid a pillow under her ass and began licking at her ass. First gentle licks around the edges, and then he mixed in probing movements almost as if he was trying to fuck her with his tongue. Licking her ass was a reward of the highest caliber for Kevin and he was so eager to please. As he rimmed her ass he moved two fingers into her wet cunt and massaged her g spot as he steadily brought her to another orgasm. He simultaneously felt her pussy spasming with her asshole, closing tightly around his tongue and fingers.

"Ohhh god that was good. While your penis doesn't do much for me, you are becoming more and more useful with your fingers and tongue." Katie joked. "I've decided I want to find the best one." She said with a smile. "You found me 5 great potential guys and the only way to figure out which one can fuck me best is to try all 5 out!" Kevin's eyes widened. "This is what you wanted, isn't it my little ass worshipping cucky? For your wife to get the pleasure she deserves? To get treated like a proper slut for once in my life? Don't I deserve the best?"

With an argument like that, Kevin couldn't think of a rebuttal. "Yes Miss Katie, you certainly do." He conceded.

"Good boy, now I will take care of contacting them from here. Do you think you have earned a reward?"

"Well I am glad you like the men I found but I know that I forgot to take the garbage out this week." He admitted.

"I am glad you brought that up, I suppose I have to punish you so you don't do that again don't I?" Kevin looked mildly scared. This part of their female led relationship was difficult for Katie but she knew she had to do it to ensure her authority and Kevin's obedience was absolute. She firmly grabbed Kevin's balls and told him to stand up. "10 seems like a good number, don't you think?" Kevin nodded, unsure of what that meant exactly but did not want to question her.

THWAP, "One!" She said with a slight grin as her hand quickly swung up and slapped his cum filled sack. Kevin involuntarily bent over as he grimaced. "Oh come on, I have seen some of those CBT videos where the women kick with full power into the guys, that was just a love tap!" She laughed. There wasn't as much pain in Kevin's stomach as he anticipated there would be. He realized that Katie was right, his balls probably could take a lot more of an impact than she was serving.

THWAP, "two!" THWAP, "three!" THWAP, "four!" THWAP, "five!" THWAP, "six!" THWAP, "seven!" THWAP, "eight!" THWAP, "nine!" THWAP, "and ten! Well that wasn't as difficult as I thought it would be, that was kind of fun!" She admitted with a grin. "Your balls are so soft and bouncy!" She bent over and dangled the key to Kevin's chastity cage, which was hanging on her necklace, close to his penis. "Well you certainly have deserved this, don't you think?"

"Oh god yes Miss Katie, please unlock me!" Kevin begged. Katie clumsily unlocked his penis and began licking it to life, easily able to fit his whole soft cock in her mouth she teased and massaged it with her tongue.

"Hah, it doesn't even know how to get hard anymore huh?" She teased. Kevin's cock definitely took a lot longer to inflate than before. After being regularly locked up and unused for weeks at a time his dick took a couple minutes to get hard again. It had been 18 days since his last orgasm. "Since it's been so long since I have let you cum and you have been so good, I will let you choose which hole you can fuck me in" Katie's sultry voice informed him as she crawled onto the bed on all fours, her gorgeous ass facing him. "It might be a while before you get to do this again." She reminded him.

Kevin didn't hesitate. He loved Katie's pussy with every fiber of his body but her ass was this glorious forbidden and unexplored wonderland. He grabbed the lube and coated his 5" cock. Then his fingers found her hole. First circling around it, trying to coax it open and then inserting one and then two fingers. She was very tight, he felt pressure clamping from all around his fingers as he tried to stretch her out. "I hope she doesn't let any of these guys have her ass, she is way too tight for that." He thought to himself. After a minute or two of warming her up he lined his stiff cock up with her hole and gently slid it in. Katie gasped a little. "Are you okay my love?"

"Yeah, your cock isn't that big bitch boy!" Katie playfully said. Kevin began pumping and immediately could tell he wouldn't last long. His groans gave Katie the hint that her premature husband could not hold out enough to give her any real pleasure.

"Oh yeah cucky, do you like fucking my ass? Are you going to fill my slutty ass up with your 18 day load? Go on, you know you can't hold out for long." She teased.

Kevin knew she was right. Her soft ass bouncing back on him always pushed him over the edge even when he was regularly jerking off. Now that he was owned by Katie, and with all the action he had prior to this it was only a minute before Kevin was groaning louder and louder.

"That's it, pump all that cum up my tight married ass. You know what is going to happen after?" She asked?

"Oh god you aren't going to make me clean it are you?"

"That book you suggested I read said to make you eat every load you are allowed!" She responded.

That was all he could take, Kevin exploded spurt after spurt up his wife's beautiful behind. Katie slowed her bouncing to a couple long strokes and then said "You better get under me quick before I spill a drop or you'll be severely punished!"

Kevin quickly got on his back and slid his head under his wife's ass. Only inches away he could see a drop of his thick cum ready to leak out of her. She scooted a little bit to position herself perfectly and then sat up, quickly bringing her used hole to Kevin's mouth.

"Ohh yeah that feels good, make sure you get your tongue all in there!"

Drop after drop came out of Katie's ass as Kevin swallowed several times. After it slowed down he was able to use his tongue to clean the outside and then push into her to see if there was anything left. Katie pushed slightly and another spurt found the back of Kevin's mouth. He worked on her for several minutes as she grabbed one of their big dildos and fucked herself to a third orgasm of the night, grinding her ass on Kevin's tongue as she came. Two orgasms in a night was an extremely rare occurrence for her but three orgasms was something that was unheard of in the entirety of their relationship. Kevin knew that Katie was beginning to unlock her sexuality.

"I am learning to like this ass worship you are so into," She said proudly. "And you practicing eating creampies could come in handy someday."

In such a short amount of time Katie had seemingly completely embraced the cuckold lifestyle. Was she as serious as she sounded or was she playing this up for Kevin's benefit?

"Thank you Miss Katie for letting me serve you and for my orgasm," Kevin warmly said as they cuddled afterwards. "I am so excited to begin this chapter of our lives!"

"Thank you for getting us into this," She said, genuinely happy at how close this female led relationship was bringing their marriage and excited for what the near future would bring.