Cuckold Humiliation
By CuckoldressAnne.
Charles was in his 50s now. He had earned his fortune and retired. He was still a good-looking guy, very well-maintained and charming. Charlotte, on the other hand, was coming out of her shell. She was going out more, enjoying life, having new friends, and still attracted a lot of guys. At first, Charles was jealous. However, he was discovering a new submissive side. He thought he would always be in charge, be the boss, and tell people what to do, but with his newfound independence, he was enjoying not being in charge, not being relied upon. In fact, when people told him what to do, he would get quite turned on.
Charles started fantasizing about Charlotte with other men and started to watch cuckold porn. He went online, chatting with other guys and mutually masturbating as they masturbated over pictures of Charlotte. At first, Charlotte was fuming when she found out. But at the same time, she was quite impressed that she still had the power to get guys off.
Charlotte’s confidence had been knocked, as Charles was struggling with his libido now that he was a bit older, and Charlotte thought it was down to her. Charles’ newfound fantasy had given Charlotte newfound confidence, and she started being flirty with guys when she was out.
The couple started to use these fantasies and role-play their sex life. Charlotte would tell Charles about instances where guys had flirted with her and where she had flirted back, that she could see the bulge in men’s trousers as she danced. Charles used to get very turned on by this, and his libido would return whenever the theme was him being humiliated.
Charles started to call chat lines. He talked with the ladies about being humiliated, almost like they were counselors. They encouraged him to pursue the cuckold lifestyle. They shared examples from other guys they talked to. This really worked for Charles; he was humiliating himself in front of a stranger, and was not in control.
Charlotte told her friends about this. They were all shocked, as they knew Charles as a High-Flyer boss. They encouraged Charlotte to flirt and pursue other guys and wished their husbands were OK with them cheating.
One night, when she was out, Charlotte got drunk and was dancing and, attracting a lot of attention. A younger guy, Toby, came over, and they started to dance together. When Toby got a little touchy, Charlotte retreated to her friends but did admit to getting very aroused. Her friends made her get back to dancing with Toby, and things got close to the point where Charlotte felt a bulge as they danced close. This made her run away to her friends again.
One of her friends went up to Toby and explained that Charlotte was shy but gave him Charlotte’s number and told him to text her. The next morning, Charlotte told Charles about the events. He was quite aroused. He’s not normally a morning person, but he got really hard as Charlotte regaled her story, and they fucked all morning.
Things were a bit taboo for a few days after the fuck session, and eventually, Charles asked Charlotte if she’d contact the guy; she was very reluctant, and to her this was crossing the line. She told her friends, and they encouraged her to explore things. Eventually, she responded to Toby’s messages and met him for lunch. She told Toby she was married, and she told him all about Charles and his fantasies. Toby backed off, and they parted amicably.
A few weeks later, Toby and Charlotte started texting each other again to explore the art of the possible. Toby said he wanted Charlotte badly but didn’t really want Charles around. Charlotte was happy to meet him, have some fun, and then return home to Charles. Over the next few weeks, Toby and Charlotte texted almost constantly, planning what they were going to do, so it was all transparent and the boundaries were clear.
Charles and Charlotte talked a lot. Charles admitted his libido wasn’t what it used to be, and this really turned him on. It wasn’t really the thought of Charlotte fucking another guy. It was more the humiliation and not being in control. Almost the embarrassment was the turn-on, thinking what his ex-work colleagues would’ve thought or people in the street would have known how pathetic he was.
Charlotte was still apprehensive. She was married. She believed in marriage and its sanctity. She enjoyed flirting with dirty talk, but actually going through with it was different. That scared her!
Charlotte and Toby met up. In fact, they met up a few times. These were all drinks in public or walks and nothing intimate. Charlotte liked Toby. She fancied him, and yes, she wanted to fuck him. She had to get over the moral dilemma. This was cheating, but she was coming around to the idea that everyone seemed to want it to happen.
One night, soon after, Charlotte was out with her friends. She was drunk and having fun. She saw Toby in the club, he was with his friends, she went over to start talking and chatting to him and his friends. They were all very forward, calling her a milf and so on.
Toby was a bit jealous, so he took Charlotte onto the dance floor where he showed her his moves and then started touching her. This progressed to kissing. This was fun. She was enjoying herself. All her friends were watching in admiration as Toby stood there, six plus feet tall, broad shoulders, and muscular, with great hips. Toby’s friends were also watching. Charlotte still had the moves, and her well-preserved size 10 figure with classy boob enhancements and a bit of Botox allowed her to more than compete with the younger girls on the dance floor.
Toby and Charlotte had advanced things as much as they could on a dance floor. Charlotte knew there was no turning back. She said she would be back in a minute and called Charles to say there was no turning back unless he intervened now. Charles giggled down the phone and said to get on with it. Charlotte had a free pass. It still didn’t sit well with her, but when she got back on the dance floor when she was entwined with Toby, her inhibitions evaporated.
Toby asked Charlotte if she wanted to go back to his place.
“I’m not ready for that,” Charlotte said, “I need to take it slowly.”
The two of them decided to leave the venue, maybe go for something to eat or chat things through. As they walked, they found themselves in a quiet corner and began to make out. After a few minutes, Toby noticed no one had disturbed them, so he moved up a gear. His hands were all over Charlotte, grabbing her bum and fondling her tits with no resistance.
After a further check on the surroundings, Toby’s hand moved under Charlotte’s dress to the insides of her thighs. She clenched momentarily, bringing her legs together, then released the clinch and kind of parted her legs slightly, giving Toby access. She passed the point of no return.
As Toby started to move beneath her panties, she reached down to feel a huge bulge in his trousers. This sent her wild. The thoughts of what’s inside there made her wet through. Toby smiled as he felt how wet she was. He reached inside her panties, slipping a finger into her wet pussy. Charlotte opened her legs wider, his hands expertly increasing their intensity. She was kissing him passionately; she had lost herself, and within seconds, she could feel herself building to orgasm.
Toby then pulled his hand from inside Charlotte’s panties. He unbuckled his trousers and let them drop to the floor. Charlotte looked down. Wow! What a gorgeous cock. She knew Charles liked humiliation, but this might be a shock even for him. This guy was big and rock-hard. Charlotte moved to grab his cock, but Toby moved away and swirled her around so she was in front of him.
Toby pulled Charlotte’s panties off. He then bent Charlotte over, and she could feel his fingers entering her. Toby used Charlotte’s juices to moisten his cock. Toby then came up behind Charlotte. She could feel the tip of his cock nudging against her pussy. She opened her legs as much as she could and helped him guide his cock inside. ‘My God,’ she thought, ‘am I really doing this? Am I really cheating on my husband? Am I getting fucked in public! Yes,’ she thought, ‘and I’m enjoying it.’
Toby was very thoughtful. He obviously knew he had a big cock and that some women struggle with this, so he pushed it in, working it deeper and deeper until he felt Charlotte clench.
“Are you OK?” he asked.
“Yes,” she said.
That was all he needed to hear, and with that, he grabbed her hips and fucked her, and when I said fucked her, he fucked her as hard as he could. Charlotte screamed. The violent fucking lasted just a matter of seconds before Charlotte reached under to rub her pussy to orgasm. Toby realized this and fucked for all he was worth. Charlotte orgasmed to a crescendo of screams as Toby pumped away at her. As he felt Charlotte’s legs go weak, he held Charlotte’s hips as he dumped a big load deep inside her. He released the grip on Charlotte’s hips; she almost fell to the floor, and as she stumbled, Toby took a step toward and showered the last of his load in Charlotte’s face and hair.
This brought laughter, which filled the air. What an amazing experience for both of them, happy, joyful sex, totally focused on the moment, and not caring for anyone else. Toby picked Charlotte up and gave her a big hug and a kiss. They became mindful of their situation and felt apprehensive in case anyone had seen them.
“Fuck that was good,” Toby said.
“My God, I am doing that again,” Charlotte replied.
With that, they embraced and walked back into civilization. Toby asked Charlotte if she wanted to stay at his flat. She declined and flagged a taxi, desperate to get home to Charles to see if he was indeed pleased with her antics.
When Charlotte arrived home, Charles was asleep. She contemplated just going to sleep. However, if she were to do this again, she needed Charles to have bought in. She climbed into bed fully clothed and grabbed Charles’ small dick, which disturbed him. Charlotte whispered in his ear, ‘I have been a naughty girl.’
She continued to describe the fucking as Charles stirred and woke. Charles’s cock grew in her hand, this was a relief as she was unsure whether this was what Charles really wanted, but his cock seemed to suggest it was.
“I have a big creampie inside me,” she whispered. “Do you want me to climb up onto your face so you can smell it and lick it?”
Charles’ small dick was the hardest it’s been for years, so she knew the answer was yes. With that, she climbed onto Charles’s chest, lifted her dress, and pushed her pelvis forward so Charles could see what a mess Toby had made of her. Without hesitation, Charles grabbed her bum, pulled her towards his face, and started to lick.
‘My God,’ thought Charlotte. ‘Charles really does want this, which means I get to fuck Toby again.’ She relaxed and just let things ride. Indeed, she started to push as much cum out of her as she could and looked down to see Charles lap up every drop of cum she squeezed out.
Charles reached down and started masturbating. The intensity increased. He masturbated frantically and blew his small dribbling load all over Charlotte’s back. The intensity of the spurt surprised Charlotte. As his moaning subsided, Charlotte climbed off his torso, took her dress off, got back into bed, and cuddled him. They both went straight back to sleep.
Both Charlotte and Charles woke up late the next morning, and it was very romantic. They were kissing and cuddling. It was like the early days of their relationship. Charlotte told Charles the full story of the night before. Charles was hard again, but as he had a really good orgasm the night before, things didn’t go anywhere, and they went down for breakfast.
Charlotte checked her messages. There were a number from Toby thanking her for the night before and some from her friends asking what she got up to. She replied, saying she was OK and they needed to meet up for the full details, which they all did later that day. Charlotte’s friends were amazed and jealous of her antics, but no one could believe Charles’ role in this. It wasn’t the Charles they all knew.
A few days passed, and there wasn’t really much talk between Charlotte and Charles. They were still processing the events, and it was as though they were both slightly embarrassed. It was a bit of a taboo subject.
Following a barrage of saucy texts from Toby, Charlotte broke the ice and said she’d love to do it again. Charles said he would love to be more involved, so Charlotte and Toby talked about the art of the possible. Toby didn’t want Charles around, so eventually, it was agreed. Charlotte could go and visit Toby and go back home to Charles, who also asked if Charlotte could intensify the humiliation.
“The more humiliating, the better,” he said.
It turned out to be the following Sunday for Charlotte’s next encounter. Charles had bought himself a chastity cage and some feminine clothing. He was going to sit in the house with a chastity cage on, having taken Viagra, and Charlotte was going to send pics and texts about her encounter with Toby. Charles was hoping the Viagra and the chastity would cause him pain as he got aroused by Charlotte’s texts and pics.
Charles also talked to a lady on the adult chat lines, and he wanted to talk to her during Sunday afternoon to humiliate himself, culminating in him calling her when he eventually licked Charlotte’s pussy on her return.
Sunday arrived, and there was an eager anticipation in the air. Charles had dressed in his feminine/ sissy outfit and attached his chastity cage, and taken his Viagra. Charlotte spent time getting ready, including new sexy underwear and the skimpiest dress imaginable. She looked gorgeous and very available!
When Charlotte arrived at Toby’s, there were other people in the flat. These were his friends who had come around to watch the football. Charlotte was a bit shy and intimidated, but all her friends made her feel at home. They showered her with compliments and were very suggestive in a humorous way, so she relaxed and felt good, flirting and cavorting around the flat.
Charlotte texted Charles with pictures of all the guys and comments about it being a gangbang. Charles texted back a picture of his small dick straining against the chastity cage and that he was in a lot of pain.
Once the football match started, all the guys settled down to watch. Charlotte and Toby disappeared to the bedroom. Charlotte was shy and didn’t want to make any noise, but Toby asked her to make as much noise as possible, as this would impress his mates.
Still apprehensive, Charlotte relaxed as Toby undressed, and she caught a glimpse of his magnificent cock. For the next hour, Toby and Charlotte fucked, sometimes intensely, romantically, sometimes brutally, and in every position possible. Eventually, following three orgasms from Charlotte and a lot of restraint from Toby, she got what she had come for, Toby’s massive load deep inside her pussy. She was exhausted.
The second half of the football game was just starting. As Toby returned to the group of guys in the room, there was lots of excitement, congratulations, and high-fiving. Charlotte, on the other hand, was quite subdued and embarrassed when she returned to the main living room, but Toby’s mates all carried on their lighthearted banter, and deep down, Charlotte was starting to love the attention.
The friends started quizzing Charlotte about Charles and their cuckold arrangement. It was all really quite fun. Charlotte loved the attention and adoration. She also embraced the humiliation of Charles, which she hoped to tell him about later. Charlotte described in detail exactly what she was going to do when she got home, how Charles was going to eat all the cum out of her pussy. A couple of the guys got aroused by this.
One guy asked if Charlotte would video call Toby when Charles was licking her out so they could all watch, which Charlotte thought was a great idea. Another guy said the situation totally aroused him and was definitely going to masturbate about it later, he then asked if Charlotte would give him a hand, which brought anger from Toby, but he was persistent and asked if Charlotte wanted him to cum in a condom that she could take home for Charles to eat. This started a lot of banter in the group, which transpired as three of Toby’s friends were going to masturbate themselves into condoms for Charlotte to take to Charles.
Toby reluctantly agreed that his mates could masturbate over Charlotte; this seemed to be a power play on his part, but they weren’t to touch or be touched by Charlotte. The rest of the guys and Toby left the room and went to the local pub to watch the end of the football match. This situation was well out of Charlotte’s comfort zone, but she was on a journey, and she was loving it. Charlotte kissed Toby goodbye and said she would call him when she got home.
Once she was alone with the three remaining guys, she started flirting, dancing, and cavorting in front of them. As they overcame their shyness in front of each other, they got their cocks out and started masturbating. Charlotte loved this. She felt so sexy and desirable. Her confidence was at an all-time high.
Charlotte could tell who was the most trigger-happy, and she focused on each guy in turn, dirty talking and being as sexy and slutty as possible to get them to blow their load for her. She could feel herself getting wet and aroused as she feasted her eyes on these beautiful young cocks all hard for her.
One by one, the guys came for her, then disappeared to the pub. The last guy was more forward and, when he was alone with Charlotte, was asking for much more. She didn’t want to lose Toby, so she rebuffed his advances, but he didn’t stick to the arrangement and removed his condom and blew his substantial load all over Charlotte’s dress. She threatened to tell Toby, but he was very apologetic after, so she knew he would never tell Toby.
Charlotte called Charles on the drive home. She told him what had happened and told him about the extra condoms of cum she had from the two guys. She also mentioned Toby’s mates wanted to watch him clean her up via video call. Charles was moaning and groaning on the call, so Charlotte knew his little dick was aroused and in pain.
Charles had been busy in Charlotte’s absence. He had made some restraints out of rope and managed to tie himself to the bed by the time Charlotte arrived home. Charlotte came up to the bedroom. She was shocked by the sight that greeted her, and as she looked at this pathetic man in his chastity, her thoughts couldn’t help thinking about Charles’ small dick and comparing this to the magnificent cocks she had experienced that afternoon.
To bring herself back to the present, she smiled at Charles, who had noticed her dress was still wet with splatter marks from the last cumshot from Toby’s mate. Without hesitation, Charlotte climbed straight onto Charles’ wanton face and pushed all that cum into his mouth. She loved this. She felt empowered, felt in charge.
Charles knew this, and he loved the fact that she was in charge and he was submissive. He was humiliated. He was not in control. Charles cleaned every last drop of cum from Charlotte’s swollen pussy. He was moaning intensely as the chastity caused him pain. Charlotte grabbed his balls and started flicking and pulling his balls to increase the pain.
Charlotte then dismounted. Charles then asked Charlotte if he could ring the chat line and tell the lady what had happened while Charlotte spanked him. He said he needed to be totally humiliated.
“Sure,” said Charlotte, and they got into position with Charles over her knee, his chastity between her legs.
At this point, Charlotte’s phone rang. It was Toby, she answered, and he was thanking her for the day and asking if she was OK. She replied that it was a brilliant day and that she wanted to do it all again. Toby was then interrupted by his mates grabbing the phone and asking if they could see Charles if they could see this chastity.
Charlotte looked at Charles, who was fumbling with his phone and trying to call the chat line. Charles said, “Sure,” and with that, Charlotte turned the call into a video call, pushed Charles off her knee and onto his back, and gave the guys a close-up of his dick in chastity.
There was a commotion and noise from Toby’s end of the call as his mates scrambled for a look. Toby then said, “Hang on a minute, I’m going to cast my phone onto the TV so we can watch.”
It was obvious when Toby’s casting of the phone footage appeared on his TV. You could hear all Toby’s mates laughing and commenting. Charlotte looked at Charles as if to say, ‘Is this too much?’ but Charles seemed to love it.
With the increased confidence Charles’ need for humiliation brought, Charlotte put the phone camera up to Charles’ face, he had eaten most of the cum, but there were still bits of semen glistening around his mouth. This initiated a raucous reaction from Toby’s mates, and any thoughts of calling the chat line disappeared. Charles loved the humiliation from Toby and his friends, degrading him.
One of Toby’s friends asked, “Have you still got those condoms full of jizz?”
“Yes,” replied Charlotte.
“Empty one on Charles’s face,” he said. “Then rub it all over his face.”
Charlotte looked at Charles, and he smiled, so she proceeded to do as instructed, which was met with hysteria and disgust from the other end of the call. Charlotte noticed Charles’ chastity. It was straining to its limit. Wow, he really did get off on this humiliation. A smile came over her face. She knew her life would be much better going forward. She had a lifelong pass to fuck who she wanted, with no retribution.
Charlotte moved the camera to Charles’ small dick and commented how much he liked the cum on his face as his dick was straining against the bars of the chastity cage. One of his other friends was quick off the mark.
“Rub the other condom full of cum all over his little dick… Masturbate him with another man’s cum as lube!” he said.
Charlotte didn’t even look at Charles this time to get the nod of approval, as she knew Charles wanted it. As she poured the cum over his chastity, she started to rub it in, and this rubbing turned into a handjob if you can call it that through a chastity cage.
Charles seemed to have no boundaries in terms of humiliation. He smiled through the pain. Charlotte saw the pain was intense and felt guilty, so she reached for the key and began to unlock Charles from his chastity. “Let’s get ready for this monster,” was the shout from the other end of the call.
As the chastity came off, huge cries of laughter bellowed out of Charlotte’s phone as Charles’ small dick stood to attention in all its four inches of glory.
Charles was imagining his little dick being cast on the large widescreen TV while five guys with much bigger cocks were watching and laughing and saying how pathetic it was. His dick grew the biggest it could (which is embarrassingly small). Charlotte was mindful of this and couldn’t believe this was the once alpha male she fell for. Charlotte started playing with Charles’ little dick, using two fingers to masturbate it to emphasize its inadequate size, flicking it and measuring it against her finger. She was enjoying making the guys on the phone laugh.
It was all too much for Charles. Charlotte knew he was going to cum in seconds. It was the most turned-on she had seen him. She started mocking him, telling the guys to come closer to their tv if they wanted to see the cumshot, as it would be a pathetic little dribble. Charles looked at her, stared deep into his eyes, and smiled. “Go on, you babydick loser, surprise everyone and blow us a big load,” she taunted.
Charles started to buck and writhe as Charlotte masturbated him with her finger and thumb. She had a devious look on her face as she masturbated Charles faster. “Oh fuck,” Charles blurted out as he contorted and bent forward, and the inevitable dribble of cum formed at the end of his small dick.
Charlotte kept masturbating Charles, this was past the point she usually stopped as it became painful, and Charles went through the discomfort trying to cum as much as he could.
The intensity was broken by the guys on the phone shouting and laughing. Charlotte acknowledged this by getting a close-up of the measly cumshot. She then turned the camera on herself and said thank you to the guys, but she needed to go now to mop up the heavy load. This brought smiles all around, and she waved and put the phone down.
Charles broke the momentary silence. “Thank you for that. It was brilliant.”
As Charles disappeared for a shower, Charlotte thought about how the roles had reversed. This once dominant man who had defined her life was now a sissy cuckold. Charlotte was happy. For the first time, she had a voice, and she had a presence. She was loving her new role, and she was getting great sex. Charles was also enjoying himself.
The End.
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