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Submission Heaven Ch. 05

Story Info
Sissy son is gently cuckolded by his loving, sadistic mommy.
7.2k words
4.53
1.9k
6

Part 5 of the 5 part series

Updated 07/10/2023
Created 08/25/2022
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I walked towards the front door with fear strangling my guts. Step after step, my feet encased only in my cumstained pantyhose made no sound throughout the living room, as I advanced to open the door to the guest.

Who is it?

I felt my mother's gaze on my back. She was waiting at the base of the stairs, watching me greet the guest, as she ordered me.

They're going to see me like this...

"The real you..."

It would be the first time someone other than my mother would see me in girly clothes.

I looked at my crotch anxiously. My transparent, frilly panties and my ripped pantyhose did very little to hide the pastel pink chastity cage. My sheer white nightie arrived at covering barely half of my butt. I adjusted the lacy end of the see-through nightie to cover my crotch as much as possible.

I felt an overwhelming impulse to run away, but with my mother watching me, I was petrified: I had to obey. The humiliation was going to be total.

In front of the door, I hesitated. My head was spinning and my mouth was suddenly dry. I couldn't think straight, with my legs shaking, my vision getting spotty, my dicklette getting uncontrollably hard and hurting in its cage as I felt it leaky again...

"Chris. Open. The. Door" Grace sentenced.

Butterflies were furiously flying in my stomach.

Obey her.

I spent all the strength I had left to reach for the handle and I opened the door.

Behind it, a man.

"Good evening, young lady."

He smiled at me. A tall, black man in his 40s, dressed in a classy business suit stood before me. His musky voice was familiar to me, his smile warm on his handsome features.

"G-good evening, mister..."

It was Don, one of my mother's main business partners in the real estate studio. I had never been fully introduced to him, but I knew my mom spent a lot of time with him. And not only in the office.

"Well dear, aren't you going to let the guest inside?" my mother said, approaching us.

I snapped back to reality, fully opening the door and moving to the side.

Don came inside, towering over me at around 190cm of height and broad shoulders - yet something reassured me about his demeanor, suggesting me not to be scared.

Only then I realized I had frozen again, and was just blankly staring at him.

"...yes?" he said.

My mother chuckled "Forgive my daughter, Don, she is usually sleeping at this time in the night"

Daughter?!

My mom reached us and greeted Don with two kisses on the cheeks.

"You and your mother make a delightful pair of twins, my darling..." he said to me. My mom's silk pastel-peach vest made indeed a good match with my sheer nightie.

"Christine, sweetie, take care of Don's coat. It would be lovely if you also served us some wine. Can you do that, baby girl?"

"Y-yes" I muffled instinctively, surprising myself as I uttered those words in a feminine tone.

"Perfect. We'll be on the couch"

Don handed me his heavy coat, which I put on the hanger next to the entrance. I could tell his cologne was expensive and refined, the scent engulfing me gently.

"You've finally agreed to let me see your house for once, Grace" Don said, looking around.

"Well, things are changing fast in this household..." she answered.

I heard them talk from the kitchen as I poured two glasses of wine, trying to come to terms with what was happening.

Mom called me...Christine?

And yet my whole demeanor had shifted towards a feminine façade as soon as Don entered the house.

Rather than letting him know that I'm a boy in women's clothes...better for him to actually think I'm a girl?

Confused, I got back to them only to see my mother leaning against Don's shoulder, her hand on his chest.

"Thank you, lovely" Dan said, his warm hand briefly over mine as he took his glass "Besides...Grace, didn't you say you had a son?"

"You must have got that wrong, dear" my mom replied sharply, and she imperceptibly looked at me for a moment. I could tell she was amused.

"Now, this really is past Christine's bedtime. I know she started uni, now, but what can I say..."

She turned to Don and gave him a light kiss on the lips. She looked back at me.

"...I'm a protective mother"

I blushed hard and stood there, shocked.

I had never seen my mom with another man.

"Come, love, let's put you to bed"

Grace stood, came close to me and whispered something in my ear, telling me to repeat after her.

"M-mommy, I can't say..."

"Shush now, go ahead and be a good girl."

I hesitated for some moments, Don looking at me in a puzzled but amused way. Then I said it.

"T-thank you...for taking good care of my mommy."

***

Mommy's finger gently entered my mouth.

"That's sooo naughty of my little girl...mommy brings in a guest and your clitty can't stop leaking..."

In my trembling, messy emotional state, tasting my precum was having the effect of a pacifier.

"Did you get all worked up for our little game? My daughter. Ooh, sweetie, you're blushing again! That is just adorable. I'll be honest, I had you wear these frilly clothes as a momentary amusement, but since you like it so much, we will be sure to bring Christine out more often"

She looked at me, drinking in all my embarrassment. I faced the floor, avoiding her gaze, my belly squeezing liquid fire in my loins. Humiliation. Incredibly arousing humiliation. With a finger under my chin she brought me back to face her.

"You did a good job, cleaning me up from Don the other times" she said, admiring my incredulous expression "Yes, mommy thought that my little girl is big enough now to know she's indeed not the man of the house, and that from now on Don will be our regular guest"

It was as if all my suspicions were proved right...and then more. Yes, she was seeing other men. Yes, what I licked from her pussy was...

"You asked why I moved your bed to the wall, two days ago. Well, now you know..."

She came close to me "...it is for you to hear loud and clear mommy making love... to another man."

She paused, observing me, taking note of my every reaction. I was caught by shivers. Shock and, incredibly, uncontrollable arousal.

"You see, ever since your situation with Gwen changed, I know just how much you are starting to find...appropriate for you this whole cuckold lifestyle..."

A myriad of reactions sprung inside me at that term, but she continued "...and I want you to know that mommy supports your sexuality, no matter how...peculiar it might be. I want to gift this to you. To let you experience it safely, with mommy by your side"

She held my hands, her tone now warm and encouraging.

"How about you try being mommy's little cuckie for a while, sweetheart? Hush, baby girl, let me finish. I want you to know that as long as mommy is feeling good, you are going to feel good too, as you explore new things with her. Uh? Oh, no silly. Of course your cage stays on. Your focus should be on my pleasure, remember? Besides, you will have other ways to play, more fitting to what you really like. You will continue taking care of my feet...and licking my pussy...plus, you have the new little friend mommy got you!"

Her eyes were now glistening as she reached for the pink dildo and intertwined my hands and hers around it.

"You will grow to love it, sweetheart. I will make sure you two become very good friends" she sentenced. From her tone, she was not sharing an intention or a promise: she was stating a fact.

"Do you know that..." her voice went down to a whisper as she came close to me, her body pressing against mine.

"...you have permission to make all the piddles you want with it?"

Again she was observing me with a penetrating gaze, the one I felt she could read my mind with.

I can make piddles? But how can I possibly...?

"What do you say?" her tone suddenly demanding.

"I-I don't know mommy, I..." cornered, with no way out and too much to ponder, I couldn't muster any response.

Like a lioness with her prey, she kissed me. I was overwhelmed by her, melting under her touch. Her kisses tasted like honey, and I desperately yearned them. Her hand over my panties-covered cage made my erection ever more painful.

My breathing was frantic as she stopped kissing and stroking me "It's okay love, sleep over it. We'll talk about it tomorrow" she said in a motherly tone, placing the dildo once again in my hands.

She left my bed and headed to the door. Her tits swayed gently in her silk vest, her deep perfume followed her, her subtle smile framed by the long blonde mane. She was disarmingly beautiful, all dolled up. Radiant.

She stopped at the doorstep, turning to look at me one more time before going to another man.

She smiled.

"Don't be shy with the lube"

***

I sat alone on my bed with my thoughts and my pastel pink dildo, trying to process everything that had just happened. But not for long. A few minutes later, I heard my mom and Don move to her bedroom, beyond the wall.

I tried to just fall asleep, so I wouldn't have to deal with anything: I yearned to just make everything dark and simple. Safe.

But I was aroused out of my mind.

Then I heard a smack. And another. Soon, movement on the bed. Mouth sounds? A deep moan by Don. I raised my head from the pillow and put my ear on the wall. I gasped and almost yelled when the headboard hit the wall from the other side, the vibration of the pound loud and clear, making me recoil from the wall.

As they picked up the pace, my cage strained hard and once again started crying precum.

I imagined her there, on the bed, her pussy spread wide open, and...

I gulped down a precum drop, almost automatically. Then I gave the pink shaft a guilty look.

In the closet's mirror, I saw in what state I had been presented to Don: my long blonde hair were still elegantly braided, and my pantyhose ripped.

My stomach contorted in shame, and my hand gripped hard on the dildo. My thighs slid one over the other, the swisssss sound and sensation of the nylons making me suddenly weak.

My ears filled with my mother's moans, looking at my feminine reflection in the mirror, I caressed my anus beneath the panties.

Then I grabbed the lube.

***

I gathered mine and Gwen's books neatly in our backpacks while she chatted with her friends in the classroom. I took both heavy bags, one on each shoulder, heading outside to wait for her.

After our breakup, I had started noticing something: it seemed like everyone looked at me with some sort of amusement.

Everyone knows she was sleeping with other guys, all along.

I couldn't know this for certain, but my gut feeling was clear. As I grew more and more paranoid I saw mockery at every corner, and I had started cutting loose more and more parts of my social life, of the few acquaintances I had.

Soon, Gwen had become the only person I talked to in class. One night, during our usual ritual, I had talked to my mom about this while worshiping her feet. I recalled her words:

"It's better for you to get away from your toxic friends. They don't understand you. They can't. We don't want to waste all our beautiful progress, right sweetie? It's all right, you have mommy by your side, and Gwen. It's all the love you really need. Don't ruin it."

Lost in thought, I sighed at the realization that my mind had not retained anything from that day's lectures: the constant chastity made me restless and constantly frustrated and, after the previous night, I was lightheaded and sleep deprived as well, still trying to process everything that had happened between my mother and Don.

The turbulent night had also caused me to oversleep in the morning and, in a rush to avoid being late, I had forgotten to put my mandatory daily undergarments: the panties and pantyhose that each morning my mother placed on my desk were in fact still there, together with the soft rubber butt plug I had grown so accustomed to. Without it I was feeling empty, but I appreciated the relief after having played with myself the previous night.

Once again, anxiety washed over me as I dreaded to meet my mother that night: she had proved time and time again that she would punish every transgression.

But I've been such a good girl yesterday...

As I reached the opposite end of the university courtyard, deep in my conflicting thoughts, I rested one of the backpacks against the fence, and I felt it give out.

BUMP!

I turned in horror as I saw I had missed the fence and had pushed the backpack over a big motorcycle parked next to me, making it fall on its side.

"What the fuck are you doing?"

Suddenly, two strong hands lifted me from the collar of my shirt "I'm talking to you. Are you blind, you fucking twink?"

I struggled to touch the ground on my tippy toes as I tried to protect my face instinctively. That must had been a pretty pathetic sight, as my aggressor let me go in laughter. Only then I recognized the imposing figure of my classmate.

Tayshaun.

"Pick it back up. If there's so much as a scratch..."

I quickly got away from him, reaching for the motorcycle handlebars. But they were not moving.

"Come on prissy, lift the damn bike"

Scared, my heart pounding in my head, I pulled and pulled, tensing my scrawny muscles, but the bike was just too heavy. As I heard the growing chatter and laughter of the students all around, I was aware everyone was looking at me, and I felt my face going red.

Tayshaun grabbed the handle with one hand and easily pulled the bike back up, without an effort. I took a look on the other side, and I was relieved it looked intact.

"You are a lucky man"

"I-I'm sorry Tayshaun, I didn't mean to-"

He stood tall over me, his presence making me shiver "Stay away from my stuff. First warning" he said, and he pushed me dismissively as he walked away. Still, it was enough force to send my butt on the ground. He paused for a moment, looking if I had anything to object, but all I could do was look down, and I waited for him to go.

A laugh spread in the courtyard. I saw Gwen covering her mouth with her hand, badly concealing her laughter among her giggling girlfriends.

***

"You shouldn't have provoked him"

"But I didn't, I just..."

"You know Tayshaun is stronger than you. You did well to submit in the end" Gwen said, and she gave me a peck on the cheek.

Those words burned, but my heart beat hard in my chest when Gwen's head rested against my shoulder, as we laid on her bed. We were in her room, watching a show, and after inviting me to get close to her, soon we were snuggled up to one another.

If it wasn't clear by this time in the story, she was the girl I had always been in love with. Ever since we were 13, when I started noticing girls, she had been the One. The first girl to make my heart beat, the classmate I found myself thinking about, wishing I was closer to her, that I was in her head as much as she was in mine.

At first, all of this was innocent and romantic - I still was a romantic at heart - but now, as freshmen...I had developed a total sexual obsession with her. I watched her body grow into the most stunning and perfect goddess she could be. As tall as a model, her perky breasts were plump and firm, her waist sinuous and slim, her hips wide and florid, her butt toned and jiggly at the same time. Her pretty feet...perfect.

After years spent trying to get her attention, I lucked out during a school trip and we became friends. She seemed to really enjoy my gentleman and servile ways, how I spoiled her and did everything for her. Until...

"You know, it's nice cuddling up with you now" Gwen said, snapping me out of my thoughts as I caressed her hair. It all felt so precious. The girl of my dreams, there, in my arms...

"Yeah, I feel the sa-"

"It used to be so stressful. Having to constantly keep your hands from touching me inappropriately, expecting your inevitable requests to do...things to you, even if I told you time and time again that I don't like you that way..."

I hoped Gwen was over this, but her reminiscing over our "relationship" was sending me in the same spot I had felt before: small, inadequate and angry. Only, this time, with my dicklette strenuously locked in its small cage, there was no trace of anger left, replaced completely by guilt and...arousal.

I felt my small nub stir in its confinement.

"I had doubts, you know, about sending you those photos and videos, of me and my dates" she admitted "but you were being so stubborn. I knew they would have been more effective than just words. Were they?"

"Y-yes..."

"Good. I don't know what turned you around, but I'm thankful for that. Now I actually feel safe. I know that even here, on my bed...you wouldn't try anything"

The demolition of my ego left me speechless, but she wouldn't have it.

"Right?" she insisted.

"Y-ye, of course I wouldn't..."

Good girl...

"That's such a relief..." she purred, hugging me closely and giving me another kiss on the cheek.

"I'm actually kinda horny right now, you know?" her voice down to a whisper. Her lips were so close to mine. My cage radiated such an incredible amount of frustrated energy...

Is she going to...?

"So, I thought of a fun thing we can start doing together" she said, reaching for her phone in her bag.

My heart filled with anticipation. What did she have in mind? She laid back next to me as she scrolled through her apps, until she opened one with a flame logo. It was a dating app.

"Wouldn't it be fun to help me swipe? Come on, give it a try" she giggled, euphorically.

What she was asking me was outrageous. Any man would have walked away in that instant...

"Good girl.."

...but I couldn't help but feel the familiar heat sensation in my belly, radiating shame and pleasure in the same amounts as I sat in my humiliation.

The truth I could not admit to myself was that, after all the conditioning my mother had put me through, I was actually getting addicted to it.

As I held her phone, the first thing I noticed on her profile were the hundreds of likes and countless messages she had received. I had the vertiginous realization that there were thousands of people out there trying to get in her panties, and that she had all the power of choice under her fingertips.

The first profile on the stack was a clean faced 20-year-old boy, a bit on the short side, with a picture of his diploma, one with his family and one with a big LEGO set.

As I pondered the absurdity of the situation, that swiping right meant vouching for this guy to go out with the girl I was in love with, I thought that at least he looked like a chill dude. I attempted to swipe right.

"Wait, really? This guy?" Gwen chuckled.

As we spent the next minutes swiping, she blocked every suggestion I gave "Chris, really, I don't understand what criteria you're following. All these guys seem somewhat...they are not men. Let me show you. Here, yes. He is hot" she said, looking at the profile of a tall Brazilian man, showing his perfect abs as he hugged his dog on a yacht, his blue eyes the color of the sky.

She swiped right.

A black 29-year-old guy looking slick in a dark suit as he came out of a BMW in front of a club, a picture worthy of a Hollywood star.

She swiped right.

37-year-old entrepreneur in the company of three women on a rooftop cocktail night.

Swipe right.

24-year-old NBA G league player, 2mt tall.

Swipe right.

I lost track of time as we swiped and swiped, matching extremely successful, handsome and rich men, with interesting lives and a striking sense of fashion, all living nearby.



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