Stuck with his Mother-in-law
Friday:
It was a lovely Friday morning when Eddie said goodbye to his wife, Mary. Little did he know that this day was going to turn his life upside down.
"And remember: Be gentle! She really is kind, even though she doesn't always give that impression."
Mary kissed her husband for the last five years on the cheek, before getting in the waiting cab.
She had been looking forward to this weekend for a long time. At last, she would see Taylor Swift live in concert with all her best friends. Eddie was happy for her, and had been looking forward to spending a weekend all alone in their house.
To relax and do whatever he wanted.
He had planned to consume enormous amounts of porn and jerk off until his hands and dick were sore. But those plans had to be changed when his wife had declared that his mother-in-law was coming to town the same weekend.
And she was going to stay at their house. Eddie couldn't say no to that. He had a funny relationship with Tracy, as she was called.
Mary had her good looks from someone, and that was her mother. They had a tight relationship, as Tracy had just turned 20 when Mary was born. That meant that his mother-in-law hadn't yet reached 50 years of age.
She was a real cougar, and in his deepest fantasies he had envisioned fucking her long and hard.
But that was far away. It didn't seem like Tracy liked him at all. She never even smiled at him. To her, Eddie was like thin air.
This was going to be a difficult weekend, filled with awkward situations, tip-toeing around each other.
Then the doorbell rang.
She was here. Eddie opened up the door, and was met with something totally unexpected.
His mother-in-law was smiling as bright as the sun.
Her curvy figure was concealed under a tight-fitting red turtleneck sweater and a rather short pleated skirt. Her blonde waist long hair danced lightly in the wind.
He looked down at her stocking-clad muscular legs, which were supported by black stilettos. The heels were high, at least six inches. Behind her he could see two large suitcases.
His mother-in-law was in town, and he felt his dick rapidly growing in his pants at the sight of this sexy cougar.
Her red-lipsticked mouth moved. Out came sugary words.
"Hello, sweetie! How nice to see you! And so kind of you to let me stay over here."
Her diamond earrings and pearl necklace moved as she leaned forward to give him a hug.
The warm embrace of her big bust made his dick a little bit harder as their bodies met.
She must have noticed his boner. Eddie hoped she didn't make a fuzz out of it.
"Will you help me with my luggage?"
"Of course, Tracy. No problem. Come on in."
Eddie took care of the luggage and moved it to the bedroom upstairs she would be using for the weekend.
When he came back downstairs, Tracy was sitting on the couch with her legs crossed. She was still smiling.
Eddie sat down on the couch beside her, but he was confused by all this. Why was she so happy?
"I am sorry to say this, but my friends have cancelled. So it seems you are stuck with your mother-in-law for the weekend."
She giggled and let out a small laughter.
"Ehh. That's okay. It's lovely to see you, though. What do you want to do, then?"
Eddie tried to hide his real feelings as best as he could while displaying a false kindness.
"There is one thing I have been thinking about. And your erection at the doorstep made my mind up."
Eddie didn't understand. Was she hitting on him? He didn't know what to answer..
"Ehh.. What?"
"Don't be silly, Eddie. I am an experienced woman. I know what that feels like. And it's perfectly normal, I know what I look like and what kind of reactions I invoke. But this brings me to what I really want to talk to you about.."
She took a pause. Eddie's heart was beating faster and faster. What was coming next?
"Mary has been quite forthcoming with me, you see. And the things she was telling me about your sex life really made me worried. After all, my beautiful girl deserves much better than what she has been telling me that you are providing her with. This is why I have tried to ignore you. A man who can't satisfy my daughter, doesn't merit my recognition."
Eddie's head started to spin. He couldn't fathom what he was hearing. The words coming out of Tracy's mouth didn't make sense to him.
"But she gets an orgasm every time! I can hear it! Everyone can, she screams so loud!"
Tracy met his eyes.
"She is screaming, yes. But she has been faking orgasms. Every single time.She has told me that your little dick isn't able to satisfy her - at all.She is a very kind girl, but now she has gotten enough. She has sent in her mother to fix this problem. Do you hear what I am saying?"
Eddie heard it, but couldn't comprehend it. His mind zoomed out.
Before he could move, Tracy had moved over and now sat on top of him. She was much heavier than his short and slender frame.
She cupped his chin with her hand, and he felt her red-painted nails sink into the skin of his cheek.
"I can't tolerate this, and I am going to do something about it, bitch."
She leaned forward and his face drowned in her big boobs. She bent his arms up and over his head, where she locked him in handcuffs. She must have kept them tucked in her skirt.
"Don't you dare move," she hissed at him.
She moved off him, and he felt her locking his feet with ankle cuffs.
Eddie didn't know what to say. He was flabbergasted. He couldn't comprehend what had just happened.
His mother-in-law had locked his ankles and wrists, and he was unable to move.
She stood up in front of him. Her tall and imposing figure dominated his sight.
Tracy spoke in a stern and clear manner.
"A pathetic man like you doesn't deserve my daughter. You are not worthy of her, or any other woman. Do you understand what I am saying?"
Eddie hesitated. He wanted to say no, he deserved everything he wanted. He deserved Mary. And he didn't deserve this! But a look at his mother-in-law made him answer something completely different.
"Yes, I understand. I don't deserve her."
Her answer came fast.
"That's damn right, you little sissy. And I will transform you into something which Mary deserves. She deserves someone who obeys her, who serves her, who caters to her every need."
She paused.
"And you will be that thing. Come over here, sissy. Kneel for your Mommy."
Eddie hesitated. He didn't want to do this. He wanted to escape.
Tracy squeezed his balls as hard as she could. Eddie let out a huge squeak.
"Getting an erection from your mother-in-law only made me sure. Now listen to me, or I will punish you even harder."
Eddie gave up. He got down on the floor and kneeled, with his head against the floor.
"Stay here, sissy."
He heard her walk upstairs, the sound of her heels meeting the floor resonating through the house. He heard her come down again. He felt her attach a collar around his neck and heard keys in a lock. Then something was attached to it.
"Stand up, sissy."
Eddie did as he was told. A leash was now attached to his neck. Tracy yanked it hard and he fell over.
"This will happen again and again, if you don't listen to me. From now on, you will call me Mistress. Is that okay?"
"Yes, Tracy."
She yanked it again, even harder.
"Yes.. what?"
Eddie knew what to say next. His neck hurt as he uttered the degrading words.
"Yes, Mistress."
He was now in his mother-in-law's full control.
She bent down and unlocked the cuffs around his ankles.
"Now, stand up and follow me."
Eddie was quick this time.
"Yes, Mistress".
She smiled at his sudden transformation and newfound obedience. She walked upstairs and dragged him along. They entered the bedroom, where he could see both suitcases open on top of the bed.
"Luckily, you sealed your own faith by helping me with your luggage, sissy. Tonight is gonna be a night you will remember for the rest of your life. Lay down."
Eddie laid down on his back on the carpeted floor while Tracy tied the leash around one of the pillars supporting the bed.
"Tonight you cease to be a man. Tonight you become a sissy. We will start in the bathroom."
She untied the leash and dragged him out of the room and into the bathroom, where she unlocked him and pushed him into the shower. She stood on the outside giving out orders.
"The first step is to get rid of all your body hair. Use Mary's razors and get moving."
It felt so degrading, but Eddie did as he was told. For every inch of body hair he removed, he felt a little less like a man. He was shaving off his own masculinity.
He felt finished, and asked his Mistress for acceptance.
"Very good, sissy. Now dry yourself up and then follow after me."
Every step, every second of it, he felt the collar around his neck. Tracy kept the leash tight, and didn't give him much leeway.
When she was satisfied, she took the towel and threw it in the corner. Then they returned to her bedroom.
"Good work, sissy. Now kneel for me again."
Eddie got down.
"Repeat after me: I am a sissy. I submit to my Mistress. I will never have an erection again."
Eddie flinched.
"Never?!"
Tracy's eyes went black.
"When I say never, I mean it. And never, ever again protest my words, bitch."
Eddie took a long and deep breath, before he repeated the words.
"I am a sissy. I submit to my Mistress. I will never have an erection ever again."
"Good girl. That's right. That ugly bulge will never appear again. Stand up."
Eddie stood up. Tracy held out a pink chastity cage in front of him.
"This will make sure you never get that erection again. But you will want it, oh yes, you will want it. You will do everything to get it."
She hunched down and put the ring around his shaft. She violently pressed his balls through the ring. Eddie squirmed as shivers went down his back.
She finished it by putting the cage itself on top of his now limp and shrunken dick. It wasn't much to brag about.
With a click she locked it and put the keys on the inside of her sweater, down her cleavage and on the inside of her bra.
"What do you say now, sissy?"
Eddie didn't know, but tried to formulate something which would satisfy his mother-in-law. He didn't want to be punished anymore.
"Thank you for hiding my ugly dick, Mistress. I will never get an erection again, Mistress. Thank you, Mistress."
"You're a quick learner, aren't you?"
She let the words hang, and made Eddie think about what had happened in the last half an hour.
He was a quick learner, indeed.
"You're not a man anymore. But you are not exactly looking like a woman, either. That needs to change."
Eddie was just standing here, not moving an inch. He didn't dare to.
If he had wanted to resist it, he couldn't, as his arms were locked. And not to forget the leash. She was powerless, at the will of his mother-in-law.
Tracy had taken out a few items from her suitcase.
"Luckily, Mary gave me your sizes, so I was able to shop in advance."
The level of collaboration between mother and daughter stunned him. This wasn't a fluke, this was very well planned.
She gave him a pair of pink crotchless panties, which he put on. The feeling of satin against his hairless skin was quite magnificent. His dick twitched inside his cage.
Tracy laughed.
"You like this, don't you? I bet you really have been a sissy all the time. Just waiting to be transformed. Tell me I am right, sissy."
"Yes, Mistress. You are correct. I want to be a sissy, Mistress."
She then put a pink garter belt on him and gave him a pair of stockings. The sensation of putting them on was marvelous. It felt so good.
She quickly attached the stockings to the garter belt. Then she produced a pair of fake tits from what seemed like thin air. She put them on him like a bra. They were at least G-cups.
Eddie couldn't see his caged dick when he looked down anymore. Tracy put a bra on him,
"Look in the mirror. What do you see?"
Eddie turned around, and was bewildered by what he saw. Except for his head and face, he looked like a sexy woman. A woman he would have died to fuck.
But now it was him.
He almost forgot to answer her.
"I see a sissy, Mistress."
"And so do I. But we're not finished, sissy."
She took out a pair of black stilettos with ankle straps. She motioned for him to put them on.
He stepped into them, and felt his calves tighten as he stood up on the tall shoes.
Tracy bent down and fastened the ankle straps, before locking each with a padlock. She secured the keys inside her bra, together with the chastity key.
This was a new body. He needed to straighten his back to equal the weight of his boobs, while simultaneously flexing his calves in order to stand up properly.
"We need to work on that posture, sissy. Am I right?"
"Yes, Mistress. You are right."
How quickly things had turned around.
But they weren't finished.
"You are not a man anymore. And that means we need a full transformation, sissy. Sit down by the vanity table, please."
Eddie did as he was told. Not that he really had a choice. Tracy worked fast with trained and experienced hands. He sat down as a man, but when she was finished with his face and nails -- with a long, blonde wig on top -- he looked like a sexy bombshell.
Tracy moved back and gave him some time to take in the newfound sight.
There was not a quiver of masculinity left.
"Would you have jerked off to the sight of this woman, sissy?"
"Yes, Mistress."
"Wrong answer."
She pulled the leash hard and dragged him out of the chair. He landed on his hands and knees on the floor.
"You are not allowed to think of jerking off. Now: Please your Mistress."
She moved his head towards her crotch with a firm hand in the back of his head. She widened her stance to make space for him. As he peeked up under her skirt, he noticed that she didn't wear any panties.
As his tongue met her pussy, she closed her legs on him and trapped him.
There wasn't any problem hearing her commanding voice, though.
"Eat your meal, sissy. And don't stop until I tell you so."
He had dreamt of satisfying his mother-in-law, but not like this. Mary didn't like to get eaten downstairs, so he was unsure about what to do.
But he soon found his rhythm in this submissive, degrading ritual. He moved and twisted his tongue in every manner possible.
But nothing happened. Tracy didn't make a sound. After what seemed like half an hour, she moved her legs apart.
"Come out."
He moved back out again. Down on his knees, looking up at this amazon of fury, controlling every aspect of his life.
"As I suspected, you don't have the ability to satisfy a woman by yourself. We need to use some tools. Stand up and lie down on the bed."
He was soon again unable to move.
Tracy tied the leash against one of the bedposts. She looked through her luggage, and produced a massive, black strap-on.
His mother-in-law fastened it right above his caged dick.
"We need some help, as you are not able to do this by yourself."
She took off all his clothes, and only her high heels on. She moved on top of him, and slowly glided onto the dildo.
Tracy reacted instantly with a moan.
"This is better, Eddie. Go on, fuck me," she ordered.
Eddie increased the tempo and could soon hear her mother-in-law moan louder and louder. The moan turned into a scream as she came and fell on top of him.
She panted heavily for a couple of minutes, before she turned around and smiled at him.
"Did you see what a big cock can do with a pussy? That's what I call a real thing, sissy."
She got up from the bed and walked towards the cabinet behind him. He heard her juggle with something, before she returned half a minute later.
"Turn around and sit up on your knees and elbows."
Eddie did just that, and his eyes met the sight of his dominant mother-in-law with same strap-on now mounted in a harness. It was well lubed, and she stroked it slowly with her hand.
"I am a nice woman. And I want you to enjoy the same things as me."
Eddie automatically lunged forward and tried to run away, but the leash stopped him.
He could soon feel the big cock slowly make its way inside him. It hurt and ached.
"Don't move, sissy. You will be stretched out and get used to it -- sooner than you think."
It didn't take much time before the hurting had gone. It was substituted with pleasure, as all the nerves in his body were activated. He had never felt something like this before. It was a transport into another dimension of sexual well-being.
With a particular hard thrust, she hit his prostate hard and Eddie orgasmed. His dick -- obviously -- hadn't been erect at all, but cum started to leak from his cage and onto the bed sheet.
"Such a good sissy girl, Eddie. Or can I call you ... Emma?"
With the last word, she did another hard thrust, before she pulled out.
Eddie couldn't speak, but Tracy took his moan as an agreement.
"Great, Emma. Now, clean up the mess you have made."
He didn't understand. What?
"What do you mean, Mistress?"
"Eat the cum, Emma. That's what good girls do."
Eddie hesitated.
He had already crossed many lines today. And even though he now was looking like a perverted vision of a bimbo fuckdoll, with his dick locked up in chastity, and just after being fucked in the ass with a strap-on by his mother-in-law, this felt like a bridge too far.
"You can't only get the spoils, Emma. You need to earn it."
Eddie adjusted his body and slowly stuck out his tongue and tasted it. It was salty and sticky and warm.
"Go on now, Emma. Go on."
Eddie forgot everything and concentrated on the task in front of him.
When he was finished, he looked up.
Tracy was recording all of this with his phone.
Eddie didn't know what happened next, but after he had swallowed it, he broke down in tears and started sobbing uncontrollably. The tears ran down his cheeks and destroyed his make-up.
He had been ambushed by mother-in-law, who was cooperating with his wife. This wasn't fair. He didn't deserve it.
He dried off the tears after a couple of minutes.
"It's good to release your emotions, Emma. But remember this: You have not honored your wife as you vowed to do. This is your reward for failing that."
Eddie suddenly felt all his strength disappear from his body. He was drained from the experience. He fell asleep on the bed, like a pet, still tied with the leash to the bedpost.
Saturday:
When Eddie woke up, it took a couple of seconds before he remembered what had happened last night. He rewinded the happenings in his head: The ambush, the dress-up, the fucking. The degradation. The humiliation.
He moved his body, but was yanked back by the leash.
His mother-in-law was nowhere to be seen.
He started to scream.
"HELP! HELP! HELP!"
He heard Tracy walking up the stairs. She was calm as she entered the room. She looked at him with a disappointed smile.
Eddie's screams stopped when she violently forced a ball-gag in his mouth.
Tracy put earbuds in his ears, which removed all sounds. Then she pulled a leather hood over his head. He couldn't see anymore. He could breathe through nostrils in the hood.
He was still flopping on the bed, moving his arms and legs back and forth. The leash kept him in place.
The movement stopped as Tracy sat down on top of him. She turned around and grabbed his feet with her hands. She tied his ankles, knees and thighs with ropes.
She moved his arms over at his back, where she put thumbless leather mittens on his hands, which she strapped tight at the wrist, before she tied his arms together with ropes at the wrists and elbows.
She moved off him, but soon felt her jostling his body into a cocoon of sorts, a kind of leather sleeping bag. She laced it up at his neck, leaving only his hooded face and leash outside the bag
Tracy took off the leash and rolled him off the bed and onto the floor. She rolled him into the sliding door cabinet, where she shut the door.
Eddie was completely trapped and could only move by rolling sideways. He hit the door a couple of times, but it didn't budge.
After a few tries, he gave up.
With no sense of time, place or his surroundings, he was in the cabinet for hours.
He thought about what a mess he had put himself in. Maybe his fate was predestined, but he thought about his erection yesterday. Could he have avoided all of this by not getting turned on by his mother-in-law?
Probably not.
Several hours later, Eddie heard the door slide open.
Tracy bent down and removed his hood and took out his earbuds. She kept the gag in place.
"Well, well, well, sissy. Have you thought things through, Emma? This is what happens when you disobey your Mistress."
Eddie had learned his lesson. Even though he was still gagged, he didn't dare to make a sound.
"I haven't been resting while you have been trapped in this closet, sissy. I have thrown away all your things now, but luckily I have bought some new and more appropriate stuff."
Eddie's heart sank. His options for escaping were getting more and more limited by the hour.
Behind her ominous and imposing figure, he could see the bed filled with lingerie, dresses, shoes and sex toys.
"The shop attendants at the mall were very service-minded when I told them about our situation. They didn't believe me at first, but the videos and pictures I have taken of you convinced them. They almost gave the things away for free, knowing they will have a trusted customer for the foreseeable future."
What future, Eddie thought. Wasn't this a short lived punishment before his wife came home?
Tracy rolled him out of the cabinet and onto the bedroom floor. In front of him, he could see a brand new fucking machine, with a gigantic black dildo at the end of the thrusting arm.
She attached the leash to the metal base of the machine before she untied and unwrapped him out of the cocoon.
Eddie felt fresh air against his skin again, which was a wonderful experience. Tracy didn't stop there, and took off his outfit as well.
He was now completely naked, except for the chastity cage and the breastplate.
She used some of her new gear on him. A spreader made sure his legs were wide apart, and his pussy ready for intrusion.
The spreader bar was attached to the base of the machine with chains. His hands were cuffed again, but the chain was long enough that he could move them a bit to reach a comfortable position.
Then she pushed a button and turned on the machine.
The lubed-up dildo thrust into his boipussy with venom. Eddie instantly felt the intense sexual gratification of being fucked in the ass.
Tracy bent down and put a large cup in front of his locked up dick.
"It won't stop until I am satisfied with the amount. This is your dinner, so remember: Good girls always do as they are told."
He had already started to leak a little bit, and tried to adjust his body so it filled up the cup.
Eddie heard the first drops hit the bottom of the cup when Tracy turned off the lights and shut the door with a bang.
He was in complete darkness. The sound picture of the situation was special:
The cum slowly dripping into the cup.
The steadfast rhythm of the machine.
His muffled aroused moans under the gag as he was fucked into sexual oblivion.
Eddie didn't know how long he was in the room. His mind only concentrated on taking the pounding. His ass went numb after a while, but the pleasure never vanished.
Several hours later, he heard the door open again.
He got thrown out of his trance and looked down at the cup, which was brim-ful with his milky-like cum.
"Great work, sissy. You have shown your value. Now drink it up."
Tracy picked up the cup and took out the gag, before starting to pour the liquid substance into his mouth.
He gagged at first, but quickly opened his throat and took it all in. He visualized drinking a large glass of beer and tried to block out the smell and taste.
Tracy detached him from the machine and replaced the spreader bar with ordinary ankle cuffs.
She sat down on his face, with her head faced against his cock.
She leaned down and kissed his locked-up cock. Tracy took out the keys and opened the cage.
For the first time in a while his cock felt fresh air. It instantly rose and stretched towards the ceiling as a plant reaching towards the sun.
"We can't have any of that, sissy, can we, Emma?"
She started to beat his balls with the large black dildo which only minutes before had fucked him in the ass.
The time in free air was short lived.
He again felt his mother-in-law locking him up in chastity. This time the cage was even smaller, and his little dick was pressed flat against his crotch. The cage was shaped as a real clitoris, and made no secret of what she thought of his little dick.
"I guess you had a little hope of a miracle happening there, Emma?"
Eddie couldn't answer properly, as the sounds from his mouth were swallowed by her juicy ass.
She twerked her ass on his face a little bit to see if his cock was still alive. It throbbed and twitched at the delight of it, but could only muster a small movement inside the cage.
"It looks fit for purpose for me, Emma."
She reached for an item from the bed before she switched positions and sat down on his clitty, facing him.
In her hands was an inverted dildo-gag, which she quickly put in his mouth and strapped tight in the back of his head. The actions were so quick and direct he didn't have even the slightest chance of speaking.
But his ears were still working.
"We need to make you presentable for tomorrow, Emma."
She again attached the leash to his collar before she removed the cuffs.
"Stand up, slut."
Eddie did as he was told. Tracy handed him a pink latex catsuit, which he put on without objecting. The tight latex stuck to his skin immediately. She put pink dog paws on his hands, which she fastened with a belt and locked with a padlock on each arm.
She proceeded by doing the same on his feet, before putting a dog mask on his face.
"You are my little pet now, Emma. A nice little bitch."
She pulled the leash hard and walked him a couple of rounds around the room, before showing him his resting place for the night.
Underneath the bed she had gotten a cage installed.Tracy tanked and pushed him inside, before securing the leash against one of the bars in the cage.
His paws gave him no chance of removing it.
"Use the night wisely, my little pet. Sleep tight."
Sunday:
And tight the night was. When Eddie woke up Sunday morning, his body ached from the soreness of sleeping in a restricted space all night long.
The door opened. He couldn't see who it was before he heard a familiar voice speak.
"I hear my mother has done a good job with you," Mary said.
The dildo-gag prevented Eddie from saying anything.
The cage door opened and Mary yanked on the leash. He crawled outside and looked up at his wife.
She struck a dominant vision, in the same catsuit as him, only that it was black. She wore thigh-high latex boots with sky-high heels and black latex gloves.
Tracy came up and joined them, dressed in a black ribbed turtleneck dress with a pink belt with a golden buckle, dark stockings and black patent stilettos.
Mary held him in a tight grip as she addressed her mother:
"Thank you, mother. I can't even describe what a wonderful job you have done."
"The pleasure is mine, as always, daughter," Tracy answered.
The two women smiled at each other, obviously satisfied with the outcome of their successful plan.
Mary turned towards him.
"I have always wanted a pet, and now I have got it, Emma. Mom is going home, but I will take her place and continue the work she has started."
She bent down and removed the gag.
Eddie was free to speak again. He looked up at the two imposing and dominant women staring down at him.
He wanted to cry, he wanted to scream.
But his transformation had been completed. He could only say two words.
"Yes, Mistress."
The end.