Mom Helps Little Brad

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Mom try's helping son with his chastity cage.
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Brad walked in his home. A dual house, his being on the top while his mother lived below. They bought it together a few years ago and she still would take care of him when needed. He didn't hear her below and assumed she was out shopping or maybe working late.

He scurried upstairs and placed the packaged leather boots on his bed and took his clothes off. Grabbing his black dildo he slathered it with lube and rested it between his round ass cheeks to keep them warm. His bum was big enough to hold objects. For a man, Brad has a rather large bottom. He had always thought it was fat and it became his impetus for getting in shape. Yet it left him frustrated since it always poked out from his pants. That said, when he wore panties he was always flummoxed that his hairless cheeks looked so ...well hot.

He, laying nude in his bed except his cock cage and dildo, unpacked one boot. The plastic bag was from Neiman Marcus. These boots might have been expensive. Maybe the humiliation was meant as an actor of kindness? He unwrapped the bag slowly. He only wanted one boot and then to quickly seal the bag again to keep the other fresh. He pulled out the boot folded the bag up under his bed. He was hit with the familiar foot aroma that he used to spend so much time with when younger. The boots black leather reflected his agape mouth. He extended his tongue and kissed it like an old lover. His tiny penis stretched against the cage and that, now familiar pressure pain, made his anus tingle. He unzipped the boot and the acrid smell became more intense. He shoved his face deep as it could go and felt some slight moisture on his face. He almost couldn't take it ...smelled as if she didn't wash her feet all week. He had to inhale more and more. He didn't know how long it would last. Her punishment was really and act of kindness. He took his dildo from between his cheeks and rubbed his bottom in search for his brown mouth. The anus puckered open and the 7 inch black cock found it's warm reception. Brad imagined his anus working like some Gigeresque oral sucker greedy for a hard ridged human male penis. He slid the fake penis up his ass and found the colon. He began to pulsate back and forth. He laid there for what seemed like hours as a throbbing mass of sucking air and buttfucking. It felt good.

Brad fell asleep. He let the dildo slide out and shoved the boot under his pillow. He slept soundly. Deeper than he had since getting that stressful job. The stink remained on his face and gel between his cheeks. Saturday morning was warm in his bedroom. He slept with only a sheet and when he rolled into his back he was exposed except for one leg. You can guess what happened next.

Bradley's mother let herself in. She went grocery shopping early in the morning and got him some fresh fruit. She was a woman In her mid fifties. Her hair still long with curles, black with flakes of grey scattered throughout. She had gained some belly weight but her ample breasts and full hips still demanded attention. She placed the fruit in his sparse fridge. She wore her active wear that morning since she had started the day with a short run but now it was almost 11 am. She had exercised and shopped yet her only son still slept. She remembered seeing his car when she came home. So he wasn't out that night. She knew she shouldn't be nose but maybe he was sick and she was not a woman with boundaries.

She poked her head in his room and saw him stark naked. She immediately knew she had gone too far. He wa sleeping nude again. Like he did when he was younger. She remembered how often she woke him and saw his bare shoulders. He would insist she leave and the pajamas, that were in the ground, miraculously were back on him when he came downstairs for breakfast. Even then he let his guard down and often she found him laying nude. She shook her head and as she was about to leave noticed the steel cage grasping his penis.

"Oh gawd, Bradley!" Her shout startled him awake. He immediately covered himself.

"Ma ...go away."

"Brad, ...are you ok? What is that ...that thing that's on you?"

Brad knew she saw his cock cage and immediately searched for a lie.

"It's just a toy. It's nothing ...it was a joke and I forgot to take it off. Please."

She stood in the hallway. Trying to give him some privacy.

"It looks very painful. Do we need to call an ambulance?" She was worried.

"No, no, no" He got out of bed and looked for pajamas pants. He put on a grey pair and went into the hallway. It's just a joke gift. I forgot I had it on and got drunk last night."

His mother looked at her handsome liar.

"Brad ...is that some sex device?" She could recount several of his alone time dalliances. The household items that went in his anus were too many to count.

He relented. "yeah"

"You need to take it off." She sighed and found his couch on the living room. He followed wearing only his sweat pants and she continued: "That stuff is fine but you can't forget about it. You can hurt yourself."

"It's fine mom but it's not supposed to come off." He stood in front of her awkwardly. She focused on his face. "I'm taking it off anyway." She gave her verdict and lowered his pajamas fast and furious. He stood there half angered but, as expected, slightly aroused. His pink head pushed from beneath his cage and he blushed. His mom shook her head. "Doesn't it hurt?!"

"A bit..." He felt a burning question form. If they were letting this honesty happen he knew it was time to ask.

"Mom, do you think I have a small penis?" She made a sympathetic face and said: "Aw, is that was this is all about?" She motioned to the cage. "You're just fine. Like most men." She looked at it again and tried to decider how to get it off.

"Mom, just because I'm like most men ...does that mean I'm small like most men?"

She looked a tad annoyed: "You're ...big. ...sure."

Brad knew a lie. "Didn't you always say. Never bullshit a a bullshiter?" She looked at the ground knowing he was right. "Please tell me the truth."

She went to his kitchen junk drawer and returned to the couch holding a hairpin. "I will be honest but you have to let me get this off."

"Well...?"

He thought for a moment. He wanted to know her real opinions but knew he couldn't take the cage off. He would disappoint Jacklyn so much. Then again the very act he remembered with her was too much to let slip.

"Ok" he stammered.

She cautiously, with just her finger tips grabbed the top of the cage and pulled up. She noticed the keyhole and delicately pushed it with the hairpin. As she fiddled:

"Um ...well honey. You are normal very normal ...in size. Don't worry." He began to sigh. "BUT ..." she continued: "Ah well, sweetie ...you're smaller for most women." The blood left his face. "Women like them the size of a big ol' flashlight because it ...well it's like big boobies on women. You prefer those right?"

He was more direct. "What size do you prefer?" She was now into lock problem solving. She knew this gadget was gonna pop once she found the spot.

"Oh I dunno."

"Please don't lie, mom." He was serious enough that she stopped and was a tad irritated now. She saw he wanted only truth not complacency. She paused and meant to send him on a positive path.

"You're father was not very well endowed. He was 5 and a half inches." She shook her head recognizing her admission. "Truth is, the bigger it is, the bigger the orgasm a woman can have. It hits her spot deep inside her and gives her a different and better orgasm than just the clitoris."

He was dumbfounded. He never knew this before.

"Even if it's just thicker. It can rub the entire vagina and give a better orgasm than just from pounding." She saw her son was silent and went back to trying to undo the cage since she didn't want him to walk away dejected. "...but you can still be a good lover. A very very good lover."

He was dizzy with the reality that he was truly inferior. It was consuming him, making him reconsider his worth but tiring him on too.

"Is that why dad left?" He was serious. Her hands stopped fidgeting with the cage. His cock was engrossed and warm beneath the cage. There is nothing hotter than the ball faced truth. But Brad was focused on her answer and she knew she had to speak with him. Even with his penis clad before her.

"Your Dad enjoyed sex with me and then he went through what you are going through now. He knew sex with bigger men is preferred by all women. He knew because he had a well endowed friend who had many many girls. He told me about this friend and I asked to have sex with him. He watched as the guy gave me the best orgasm I've ever had."

She saw the cage had moved a tad and she now pressed his testicles down and placed the hairpin against the lock. His prick pressed more. She could tell he was erect and she worried what it was doing to him. She became focused and worked.

"I think I can get it." She jiggled the cage. Brad was reeling as thoughts of her father being cuckolded by his mother filled his brain. She tugged now on the cage. "Will I have to let me wife fuck bigger men?"

"Yes sweetie. You can always watch and even help. It's the normal way." She said while tugging more.

His head swirled with thoughts of his future wife making him watch a fat cock making her wet and cum. He felt an eruption from between his thighs and up his ass. He looked down and cum was spurting from his cage. As the semen spurt from between the steel rings his whole body felt an intense deflation. His mother gaped and he moaned.

She removed her hands quickly but they were soaked. She looked at the glistening semen and couldn't believe just how much. Brad now red faced felt embarrassed but elated too.

"I'm sorry, mom." He felt terrible with the reality setting in.

There was an awkward pause...

"I'm going downstairs and washing my hands. I'll let you deal with that. Maybe you should keep it on for now. ...it's ok. Well now you know your place with your penis and maybe that made you feel good."

He ran for the shower and she got up to look for paper towels for her hands. She stared at her boy's semen and felt an usual stirring feeling. It was her son and this was his seed. She looked and found herself alone. She put three fingers in her mouth and tasted him. The warm moisture slid down her throat, it tasted like him and she felt oddly normal.

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6 Comments
AnonykAnonyk10 months ago

I love stories where the mother leads her son into being a cuckold. It's so hard to find good ones. I would love a sequel to this story where we dive deeper into the son's head as he and mother go about their daily lives. She'll have to constantly remind him of his place and show how many of society's sexual norms don't apply to him.

Ombra92Ombra92almost 3 years ago

oh boy why this does not have continuation?

tensunny09tensunny09almost 4 years ago

Please continue the story! I like it when the protagonist wears a chastity cage simply because he enjoys it, not because he was forced into one. It would be great if his mum becomes his strict and unyielding keyholder!

AnonymousAnonymousalmost 4 years ago
Interesting story

It is heartbreaking for a mother to have to tell her son the truth. The guy is better off knowing he does not measure up and adjust his expectations. Never bullshit a a bullshiter lol

iwannabeachastecuckoldiwannabeachastecuckoldalmost 4 years ago
Need second part

Waiting for the series

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