Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereA sense of clarity rang in my brain as a hammer striking a bell: I could never compete. Every fantasy about proving myself to Gwen and getting her to change her mind about me seemed so silly, in front of this army of suitors.
At 18, with my petite and delicate appearance, my bad grades and the little allowance my mom gave me...I didn't stand a chance.
A notification came from the app and Gwen pulled her phone closer, before I was able to see the sender.
"Puppy, would you...would you be a sweetheart and take my shoes off? I want to get comfortable, there's someone I must answer to..."
My heart jumped with joy at the request, and my dicklette had a painful straining spasm. But my curiosity got the best of me:
"Who is it?" I asked.
"Nha-ha, it's private...for now"
I headed at the base of the bed and I took her black leather loafers out, revealing her feet in sheer reinforced-toe nylons. She smiled as I had a shiver of pleasure taking her feet in my hands and inhaling the first sniff of her scent.
We spent countless minutes like this, me gently massaging her feet while she texted, ignoring me.
My hands followed her arches, her toes, her heels. Her soft skin and expensive nylons feeling like heaven in my hands, I nurtured my fetish, feeling it only grow stronger.
"I need your advice on how to handle this guy...he's a tough one" she said "but keep massaging. This guy...he doesn't know who he's talking to"
And so, the conversation started. I heard the back and forth between her and this mystery guy and I was astonished at how bold he was. But while I found some remarks extremely offensive, she on the other hand blushed and smirked. I could have never talked to her that way.
"Mmh, you rub my feet so well Chris. Where have you learned?" Gwen said, as the thought of telling her I was my mother's footstool sent a jolt of beta pleasure in my caged clitty "Or is it just talent? I honestly missed our girls' night... you know, yesterday I removed my nail polish, do you want to reapply it? You're being on your best behaviour...I'll even let you choose the color" she giggled.
I nodded and she removed her pantyhose.
Thinking back on this scene, with her texting another guy while I painted her toenails, it was clear that in that moment things had taken a definitive path, our relationship was forever changed. Aroused out of my mind, I barely understood it, too busy relishing in the privilege of serving her feet.
In all that, I tried my best to give her advice "Why is he saying he doesn't date girls with boyfriends? How would he know? He has never met you"
"In reality...he has, Chris. And I have to ask you to do something for me. I know it's something big, but...I really want to go out with him"
Her saying this to me felt surreal. Involuntarily, I nodded.
"You remember Tayshaun?"
My stomach plunged as I got a feeling of impending doom.
"Could you tell him you're not my boyfriend anymore?"
***
I made my way towards home knowing punishment awaited me.
It was the first time I had forgotten to put my undergarments on, and my mother never forgot to check that everything was in place, every night. What had started like a temporary punishment seemed now like a daily occurrence, with no end in sight.
When I quietly reached the front room handle, careful not to make any noise, I hoped I was early enough to come back before her.
Then the door suddenly opened.
"Welcome back" Grace greeted me with a subtle smile. The motherly apron she was wearing contrasted with her business pantsuit and heels.
As I cautiously got inside, I was enveloped by the unusual scent of dinner being prepared. I left my backpack down and got prepared to fall on my knees and remove my mother's heels, when I saw her heading back to the kitchen. I stood confused as she always wanted me to greet her by kneeling and serving her.
Then another sudden impulse came to me, from the habits she had instilled in me.
I should dispatch these boyish clothes and get into my...
"Chris, darling, help me understand if this needs more salt" my mom interrupted my thoughts.
I reached her to find half the kitchen in beautiful disarray: beef stew, red roasted potatoes and apple pie were on the menu, with pots and oven producing a symphony of scents.
I couldn't ignore a sense of confusion while I tried the stew. I had been the one cooking in the house for a while, and it was unexpected seeing mommy busy at the stove, as I recalled her doing in the past.
"Oh that's so tasty! And enough salt, yes"
"I'm glad you like it. Now wash your hands and sit, dinner is ready"
I watched my mother serve dinner while humming a catchy tune, and I instinctively smiled. It had been years since I'd seen her so radiant. While she always maintained her sense of elegant and strict composure, a certain relaxation seeped from it.
I was expecting a tense conversation about what happened the day before, but surprisingly we dined and spoke pleasantly. She looked so proud, tasting red wine as I told her how I helped Gwen swipe on her dating app. I almost brought up the topic of the accident I had with Tayshaun, but I carefully managed to avoid it.
"It's wonderful that you are able to be so useful to Gwen. Did you enjoy it? If I know my little boy, it felt all tingly down there...you are so brave to follow what makes you feel good, and all it took was a little encouragement as mommy's cuckie..." she smiled subtly.
Her kinky talk made me blush and look down, as I pondered her line of thinking.
Does Gwen also consider me to be...her...?
"It truly seems like things are starting to go the right way, sweetie. We still have much, much more to do, but mommy always notices your progress as an obedient love, doing your homework, not giving up to your toxic tendencies...and yesterday with Don you were indeed on your best behavior" she said, and she kissed me on the cheek. My heart radiated at every ounce of affection from her, and I didn't closely ponder the diminutive way she was addressing me.
She excused herself out for some minutes as I arranged the plates, pots and cutlery in the dishwasher.
It was not so bad. Maybe things were going better than I thought. I enjoyed the company of two extremely beautiful women that I loved, and even if I was not in charge, maybe that was not my place after all.
Maybe this is my place in the world.
Maybe tonight she will reward m-
"Chris. Come here."
My blood froze as I got back to the present. I reached her in the living room, finding her standing next to the sofa. The room was illuminated with dim light, and suddenly I felt in a gloomier atmosphere.
"Imagine my delight this morning, waking up after my wonderful night with Don, coming to your room and catching you still asleep with your cute nightie, your golden hair in mommy's braids...mommy's dildo still inside you..."
She held her phone up high and showed me a photo of me in that exact scene. I plunged into a vulnerable and shameful state, looking at myself in that condition.
"You behaved like an excellent, obedient girl yesterday, my dear...and you sure seemed enthusiastic, am I right?"
With the photographic evidence in front of me, I could only nod.
"So eager to be mommy's little cuckie, yes. So imagine my disbelief at finding these on your desk today, untouched."
I stepped forward, seeing that my worries were, as always, justified. Arranged on the side of the sofa were the panties, pantyhose and buttplug she had selected for me that day.
"M-mommy, I can expla-"
"Shush now, shush sweetie..." she said, hugging me softly, my head gently resting on her ample bosom "We are going to have a precious bonding moment, now, to let our feelings out. It's essential that you remove your clothes first."
It was all happening so fast, I didn't have time to react to her demands.
I nervously complied and stood naked in front of her, wearing only my throbbing chastity cage. When she removed her apron to reveal her business pantsuit, it was as if her demeanor shifted even more gravely.
She sat and instructed me to lay down on the sofa, with my head on her thighs.
"It's important for you to know that mommy rewards all your good deeds" she said, caressing my cheek "but she must also punish every disobedience..."
I was instinctively vulnerable and afraid as I felt a hand now gently cupping my testicles.
"Or would you rather have a careless mother, one that doesn't love you at all?" she asked, pressing slightly harder on my bare balls. I shook my head, feeling how needy I was for her attentions
"No, no, you see, you need a mommy that cares for you, who is on your side, helping you blossom. And for this, mommy has to take the responsibility of controlling your conduct and even punish you for it, if necessary. You see how much progress you have already made, this way?"
As she imparted me yet another lesson, I was gently melting in between her caresses and her soothing voice.
"It's hard, and it requires constant efforts and attention from me, and yet it seems you don't care. But now things are changed, Chris. Perhaps, Christine is going to me more compliant."
Right when guilt was invading me, she suddenly shook me using that name.
Christine.
"Turn around" she ordered, and I did not dare to decline. As I turned with my belly down on her legs, it was evident to me what that position was for.
"Remember that it is for your own good, babycackes."
SMACK!
I opened my mouth but no sound came out, shocked by the hard slap on my butt mom gave me.
Memories of being spanked as a kid rushed up my memory, making me panic even more.
She circled her fingers on the sore spot "Why didn't you wear them?"
"M-mommy I-I was late and..."
SMACK!
"Mommy knows what a liar my little girl can be, so we are going to
SMACK!
take our sweet time and let you
SMACK!
share your real feelings with me, is that right?"
"Mommy I'm sorry I'm so sor-
SMACK!
please please I..."
SMACK!
She stopped and caressed my burning cheeks "Hush, baby...what cute little bottom you have, so smooth and round...now, think well before you answer. Let mommy's spanking clear your thoughts, first. We will take our time, my child, we have aaaall-the-time-in-the-world..." her words a somber verdict that sparked a rush of fear and liquid fire in my loins in equal measure "...just let it happen."
And she resumed. Spank after spank, the pain radiated hard from my scorching bottom as I tried to wriggle away but was unable to do so, as she was indeed taller and stronger than me.
SMACK!
As I took my punishment, I realized how deep the relationship with mommy had become,
SMACK!
how intertwined our lives were now that she was my step-mother,
SMACK!
my lover,
SMACK!
my mistress,
SMACK!
my cuckoldress...
SMACK!
A sense of clarity emerged in me. There was no use in trying to hide things from her anymore: I had to fully surrender, and entrust myself to her. All those changes were scary but they proved that she cared for me, that she loved me...and she wouldn't have done me any real harm in the end...right?
"I-I WAS ANGRY! I WANTED TO B-BE A MAN...AND DO AS I WANT!"
Tears came to my eyes as I cried in truth and liberation.
"AND M-MY CAGE HURTS MOMMY! It hurts and with the pantyhose and the plug my Pinky tries to get hard all the time! It drives me crazy!"
The spanking stopped.
There were long moments of silence, before I felt a cold lotion being applied to my butt cheeks "Shhh, baby girl, shhh...I'm so proud of you...you are so, so brave for letting out the truth to mommy...it's okay sweetie, cry it out as mommy cures your sorry little bum bum"
I kept crying and I felt a rising sense of peace, together with the familiar desperate straining against my cage.
"Is the constant feel of nylons against your trousers arousing you to no end? That's too bad...and the plug, I had not anticipated such a small plug would already stir your little sissy button so much..."
"Nngh...yes mommy..." I grit my teeth as these remarks made me strain even harder in the plastic tube.
When the cream was well absorbed, she turned me back with my head on her lap and kissed my tears away.
"You took the first punishment beautifully, my dear, well done. Now. It greatly displeases mommy that you still want to rebel to me, and that you cannot bear your cage" she said, once again pampering me and caressing my long hair "I hoped you would make the effort of keeping the bad thoughts away, and keep your Pinky Pinky nice and soft in your little cage, it's really such a cute small clitty..."
"But mommy, I don't know how..." a desperate globe of precum squeezed from the pink device as I turned my head in embarrassment. It was at that moment that I noticed the usual tripod and the camera blinking red, showing that, as most of our lewd time together, we were being filmed even then. Mom fed me my precum while she continued:
"No."
"W-what..?"
"I will be very clear now, Chris. Chastity-is-unquestionable."
My eyes filled wide with desperation.
"We talked about how marvelous life can be by accepting yourself, as a beta lover...a sissy...mommy's cuckie..." she read the myriad of emotion that were stirring inside me at the use of those words, but she kept going "But you have hurt me and lost my trust when you decided to touch yourself as you pleased. To ignore the first promise you ever made me."
She gently put her forehead on mine, her voice down to a whisper "None of this has any meaning if mommy doesn't control when you are free to make piddles."
I was crushed, feeling my cage more oppressive than ever as my desperation grew.
"And Don will be here again. And again. Until every ounce of toxicity leaves you, until you can be honest and enjoy it. Openly. And then again and again, of course. Mommy really likes Don, and you will learn to wait with trepidation for his visits"
I heard again in my head their loud and passionate lovemaking of last night, just a wall away from me...
"But..." she reached for something beneath her shirt, in between her ample breasts "...it doesn't mean that my love cannot get a bit of relief when behaving good."
Click!
I looked down as she carefully removed the pink plastic tube of my cage, leaving the base ring in place. A wave of relief washed over me and my modest sex, now standing hard...and still disappointingly small. I could have sworn that it was even looking somewhat smaller.
"T-thank you mommy! I won't touch it I swear, I..."
"Swearing already put you in big trouble, I wouldn't push my luck. But you are free for the evening. We'll see what to do about the nights..." she pondered. It would have been lovely to sleep without my cage: every night I was waking at least once, as my erection battled the useless fight against the hard confines.
"Now, I know you have been waiting for it all day. You may kneel."
I got off the couch, my butt still sorely burning, and I went on my knees. I eagerly kissed her first heel, then the second, and proceeded to remove them. The beautiful scent hit my head as I prepared to feast on my fetish.
"Nha-ha. I said this was the first punishment. Did you forget to tell me anything about the day?"
She knows.
Normally, I would have done anything to avoid another punishment. Yet the clarity in my head was still with me, pointing me to one imperative:
Surrend to her
"Actually, yes, today...I had a discussion with..."
Mommy's stare was hard as steel as I fumbled in my words, trying to at least belittle what had happened.
"I had an...argument with a...a colleague, but then we s-settled good, it's nothing mommy, we're friends..."
I pictured myself going to Tayshaun to give him a free pass with Gwen.
Yeah, a true friend.
"Are you sure? Someone called me today, and told me you were in a fight. With another boy. They said everyone saw you push his motorbike to the ground."
My eyes widened in disbelief. I knew where this was going.
"I-IT'S NOT TRUE! It was an accident, and then he put his hands on me!" I pleaded, still kneeling in front of her.
After a nerve-wrecking silence, Grace let out a deep sigh.
"Disobedient sissies get spanked. But toxic masculinity? That's unacceptable. And we know where it comes from, dear. Give me your hands."
I held her hands, her fingers crossed with mine. Did she want to just hold hands and lecture me about toxicity? My hopes where getting high.
Then I felt the kick.
Thump!
Her stockinged foot delivered a clean, hard strike to my balls that left me without breath.
"It's okay sweetie. One out of three..."
"..nnhh...wha...nononono-"
Thump!
Another kick hit me and pain pierced me like a lightning strike from below.
She had her grip insanely strong on my hands as she kept me down "...just one more. You will soon thank me for this."
Thump!
The strongest of the three kicks broke me as she released me and I fell on the carpet behind me, holding my sac.
"I believe it is no coincidence that the day after mommy's special night, you refuse to wear the clothes she lovingly picked for you and you get yourself into a fight. It's your male ego getting in the way. Oh, what a poor young boy, such lies you were told all your life..."
I slowly got back to my knees, still holding my hurt testies. But I couldn't hide that my Pinky Pinky was springing desperately hard. Almost vibrating.
"...that you must me strong, and competitive, and fuck girls hard...no, oh no no, my baby boy is not like that...but he is a lucky little love, because mommy is here for him now...and we will be kicking all those lies away" she smirked, a threatening tone towards the end that did not go unnoticed, making me look at her afraid.
She stood, and removed her jacket.
"While Chris is in detention..." she said, unbuttoning her shirt "...I still believe Christine deserves to be so, so spoiled..."
She finally slipped off her pants, slowly, pointing her butt towards me while doing so. Where a moment before was the threatening figure of Grace in pantsuit, now was a voluptuous blonde in refined lingerie: a lace brassiere, garter belt, silk panties and stockings.
I looked at her, astonished.
"Sweetheart, be a darling and serve me another glass of that red. We wouldn't want to spoil the bottle, right?"
That mundane order shook me off my stupor and fear. I fetched the wine and as I handed it to her I found myself standing at a safe distance. She noticed this, and pointing at the spot in front of her she invited me to kneel again. I gulped hard. She looked absolutely divine, sitting there in her lingerie. All my wires were being pulled, all my buttons pushed.
"Now only cuddles for my good girl, I promise. Be a love, and fetch your dildo as well. Don't you want mommy to make you feel good while she tells you of last night?"
***
Mommy's feet were brushing my free erection while I moved my hips, taking the pink dildo in and out, the shaft safely secured on the floor by the suction cup at the base. I was hugging her knees, my head resting on her thighs as I slowly went up and down.
And she told me everything.
I grit my teeth for the sweet intruder in my tight hole and for the jealousy, as I listened to every detail, my mother gently caressing me, immensely pleased.
I remembered Gwen telling me of her time with Henri, and I felt as if history kept on repeating itself, over and over, with all the women of my life. Only yesterday, Don was sitting on this same couch, kissing my mom in front of me.