Submission Heaven Ch. 03

Mom's finger was gently sliding in and out of my ass.

"...and tell your new boyfriend I said hi, if you want :)" she finished to dictate.

I was lying on my back on my mom's bed, my legs spread wide, wearing her panties, in the difficult task of typing the most humiliating text message I had ever sent to my ex-girlfriend, all while accepting mommy penetrating my ass.

Reading the message on my phone, I hesitated.

"Did you send it?" my mom asked, gently pushing me with an ever so slightly impatient tone, slowly but forcibly plunging her whole middle finger in my butt, up to the knuckle.

I gasped and moaned, trying to move, but my legs were tied to the bed. I had to take it all in.

My twitching dicklette squeezed a drop of precum as I sent the message, shaken by a jolt of humiliation and excitement. I showed it to her.

"Good. She has not answered to your messages for, what, five days? But what did mommy teach you?" her finger now resuming the slow penetration, varying with each thrust the amount of finger she was feeding to my tight, lubed hole.

"A good friend texts his miss e-everyday"

She gave a smile of approval as her finger curved upwards and started massaging a round place in my ass "Gooood boy..."

I moaned as she circled it "Do you like mommy playing with your button?"

I didn't answer. As always, she was filming me with her phone, and the amount of unrepeatable stuff I was saying in front of the camera was now starting to be really embarrassing. She pressed harder, causing my voice to crack up "Y-yes mommy"

"What do you like about it?" she asked, her finger now doing very soft but quick presses on it. It was now the fifth day in a row that she'd been training my ass, and she was developing an increasing desire to make me confess all my deepest, shameful feelings.

"I-it's like...aaaah...it's like you're touching the...the root of my dick" she suddenly pressed very hard, and I realized my mistake "Uugh - of my Pinky! I meant my Pinky Pinky!" I corrected myself.

"And it makes...it makes me all hot" I said, looking away from the camera. It was true. No matter how shameful I felt, I had now started to look forward to the daily sessions with my mom. The penetration itself was uncomfortable at first, but then it made me all tingly...and the prostate massages...

"To think that I believed I had to ease you into it" she purred "who knew you were already playing with your anus...what a curious little man we have here"

"I did it just a couple of times...to know what it feels like..."

"Oh, don't downplay it. You hole was already so loosened up and ready for mommy"

She paused, then, with a sterner tone she resumed "Do you think Henri would do such things?"

That name stinged my ego instantly. Henri was Gwen's new boyfriend, and I was painfully aware of what they were doing in their 2 weeks stay at his house, outside the city.

"I-I don't - aaaah" she slowly circled my button again, the circular motion being unbearably pleasurable "I don't know..."

"Oh no baby. He's a stud. Was he in the photo Gwen sent you at the cinema? She had him all in her throat" I nodded, looking away, trying to hide my shame and my pleasure at the camera "Beautiful dick, that one. And he's fucking your ex-girlfriend probably in this very moment. Isn't it why we are doing this, sweetie? We need you to develop your empathy towards women, to feel what they feel..."

She increased the pace of the penetration "Maybe she's even taking it up the ass at this very moment..."

I released another high pitch moan.

"Yeees, it feels good to think about that. That another man is giving her so much pleasure...that's good, sweetie, we want to encourage that, we want you to lose all your toxicity...and you sure are staining those panties well"

My panties were indeed drenched in precum, and after a whole day of leaking into them they had a deep scent of sex.

"Now that we wrote to her, it's time for our daily lesson"

She withdrew her finger, leaving me empty, and she pushed it into my mouth, having me lick my juices. She was wearing a sexy night camisole and a silk vest, sheer tan pantyhose and peach-colored satin boudoir mules, the ones she always walked in the house with. God, I loved those shoes. To think how many times I masturbated while smelling them...

She sat on the bed, in between my tied legs, and she spread her long legs in front of me, resting her feet at the sides of my head. I took a deep breath, dreading the impending edging session.

She pushed the slit of my panties to the side and applied more lube on my hole. The camera as always on the tripod, filming. Her finger back in my ass. She fed me a large drop of precum I was leaking, and he started slowly jerking my Pinkie with two fingers through the satin fabric of my panties.

As with previous days, she kept edging me slowly and lecturing me, while I gasped in pleasure and torment, barely able to answer her.

"I was thinking of the video Gwen sent you, at how hard, how long her guy fucked her. There is no way you could do something like that, be that big...that strong... having such endurance..."

The sensory overload I was on didn't allow me to be infuriated at her words, not with my dicklette on the verge of cumming, not with my ass so hot in pleasure from her penetration.

"Isn't Henri so generous to lift you of this burden? Freeing you from the need to perform, the need to fuck? Not that you're by any means Gwen's boyfriend anymore, but when you'll find the perfect match for you it will be so much more comfortable being yourself, sweetie...a good, nice, pussy-free cuckie..."

"Not for me!" I cried, my dicklette responding instantly to that new, unexpected possibility.

Once again, the stroking stopped "Yes sweetie, cumming it's not for you. See? A good sissy knows that she has to cum only when allowed to...she can't risk making a mess at the wrong time..."and she giggled.

She was mindful of my responses to the different words that she said, and had started using them more often. Sissy...cuckie...

I squeezed my crotch, and I released a long moan as the gentle massage of my pleasure button that my mother was giving me accompanied my thoughts, and made me squeeze a large globe of precum from my Pinky.

I couldn't tell how much I stayed there. Half an hour? My abs hurt as I breathed hard and long to contain myself, squeezing my crotch muscles to avoid cumming, but having as a result just my butt squeezing harder on my mother's finger, making my prostate sing with pleasure.

When my stamina was almost over she stopped, and slipped the panties off me.

"I'm honestly surprised by your progress, honey" she said, sitting beside me "You've worn your cute panties all these days, you've endured all my edgings..." she looked almost disappointed as she said this, though.

"It's time for a reward." She placed her feet on my face. I moaned and took a deep breath of her warm soles, my hands touching and massaging her nyloned feet.

"Do you deserve to cum?"

"I-I don't know mommy...can I make a piddle?"

"Mmm..." she started stroking me again, this time with her whole hand, in a very slooow motion.

"Would you like to cum with my feet on your face? A true orgasm?"

"Oh yes mommy, yes please" I whispered from under her feet. I felt that if I had cum in that moment, my dick would have shot gallons of cum.

She started stroking harder "Well, a dirty small dickie like you doesn't deserve it, right? What can we do?" she pretended to be in deep thought "Well, if you want a true orgasm you will get it, but you'll receive a hard punishment afterwards. I'll make you sure you regret it".

My heart suddenly plummeted. She clearly didn't like this option.

"If you want me to ruin it, you won't be punished, but our sessions will become longer, and harder" she said, and I felt a new, sudden intrusion into me. She was pushing a second finger in my ass.

"But if you completely give up cumming for today...you'll have a special reward..." she purred. I grit my teeth as her second finger was now all the way in.

My button was all clenched up, my dicklette sensitive as I'd never felt it, my balls so full and heavy it was becoming uncomfortable. There was no way I could have just walked away without cumming. But what about the punishment? I had to cum, but I couldn't defy her...

She was now fucking my ass with two fingers at a steady rhythm and stroking my cock like crazy "Then? What is it?"

I was not ready. She kept stroking. I felt on the brink of orgasm.

Obey her.

"N-not for me! NOT FOR ME!!!"

She let go.

My cries were deafened by her feet on my mouth as I desperately felt my Pinky Pinky being released right before the point of no return.

My mom was still stern and serious, but you could tell she was pleased.

"This is the answer I hoped for. You took the obedient option, the one that pleases mommy, like the good boy you are"

She laid beside me fondled my full, sensitive balls in her hand.

"And now, for your reward..."

I looked at her, desperately horny and out of my mind, burning to know what I had gained out of my torture.

"...you'll be mommy's personal assistant tomorrow, at the office. A whole day with mommy, as her little helper... we will have a lot of fun, sweetie... and if you keep behaving..." she whispered to my ear "...mommy's going to let you cum with her feet"

I forgot all my desperation as my eyes brightened with lust.

***

I was licking my mother's feet when someone knocked at the door.

"Grace, you have a moment?"

"Sure, Don, come in"

I freezed.

The door opened, and I heard footsteps of a man. They briefly spoke about a new client. I could hear the warm, strong voice of the man.

"Is that all?"

"Yeah. I'll leave you to your work now" and soon the door closed again.

I turned, trying to see if the desk had some empty space. Fortunately, I was completely hidden.

"Why did you stop, Chris? Resume."

I nodded and began worshipping my mom's feet again, laying prone under her desk. That day, even though it was a Sunday, the whole office was doing overtime, and my mom brought me with her to help.

"You thought I would have left you all alone on a Sunday? Oh, sweetie, you know mommy loves you. Besides, we really cannot risk you getting frisky all by yourself and making a piddle without permission, can we?"

"No, mommy"

"Exactly."

The office managed real estate properties, and directly owned many of them. As the partner with the highest percentage, my mom was actually the boss. I mentioned previously that she is actually my stepmother, and that she inherited my father's wealth. You might think she just enjoyed the inheritance, but she actually worked hard to make that fortune grow, acquiring new property and becoming a skilled businesswoman.

"Ooh yes baby keep massaging...keep licking...if you keep being a slacker in your studies, I think we found a good place for you in this office...as my personal mat..."

I sat there, taking her insults in. While I smelled and licked her feet, today in lovely sheer brown nylons, I felt again the indescribable arousal coming from her humiliating words. It felt right, and secretly...I wanted more. I shifted my legs and felt the sticky sensation of precum in my lace and satin panties.

I stayed there for a while, eventually lying down on the moquette floor at her request, my face providing a literal mat for my mom's feet to rest on.

In that position, I let my mind wander elsewhere in a desperate attempt to distract myself from her beautiful feet resting on my face, every breath I took being a sweet, intoxicating torment for my dicklette: I knew all my excitement would be left there, frustrated, denied of any relief.

"All right, it's time for a break sweetie"

I was shaken out of my thoughts.

"Get up. I'll be going out for lunch with Don. In the meantime, there is someone I'd like you to meet..." she said, with a wicked look in her eyes.

I put her heels back on and got up. Grace opened the door of her office and led me through a corridor to another room.

"Helen, can I come in?".

The door opened, and I was surprised by a stunning sight.

A girl in her mid-20s, of mixed race, with beautiful amber skin and sharp green eyes, stood by the door. Her make-up and attire were perfectly professional, and she radiated a striking aura of elegance. She was, the same as Grace, visibly taller than me, especially so when considering her heels too.

"Grace, I was just about to finish. The contracts you requested are ready" she said.

Her voice was musky and warm like spiced honey.

"I can start the next ones during lunch hours"

"You're such a doll, dear. Your dedication is admirable" my mother said "To keep you company, I entrust you with my baby boy" and she pushed me forward "he's a bit shy, but he has his uses..."

The girl smiled.

"Now, I must leave with Don. I'll see you later!"

Grace left the room.

I was now alone with the girl.

"Quite the woman, your mother, uh?" the girl giggled "I'm Helen, by the way" and she reached out a hand to me.

"I-I'm Chris" and I shook her hand, my mouth still gazing half open as I couldn't look at her in the eyes.

And so, we had lunch. We ordered something as she quickly finished the work she had. She looked smart, orderly, precise and effective. I admired how she got the final phone calls through, her sweet attitude melting the hearts of the clients.

We talked, we laughed. A wave of good feelings washed over me and I forgot all the travesties of the previous weeks, even the fact that I was currently wearing frilly panties under my clothes, and that my balls were painfully full.

All the initial embarrassment was gone, and I felt that she was having a very nice time with me as well.

Girls like her are not for you.

She was sitting on the desk with her legs crossed, her long, toned legs encased in tan pantyhose.

She wore a cream-colored short skirt and heels of the same matching color. She wore a teal turtle neck sweater, and had her dark hair lifted up in an impeccable chignon.

She asked me all sorts of personal questions. I tried my best to look interesting and cool but I couldn't help feeling kind of silly. She kept listening nonetheless, looking genuinely interested.

I loved her laugh.

When it was my time to ask, I learned that she was a new acquisition of the office, as she was hired by my mother for a 6 months internship right after she got out of university.

While talking, she was looking for a comfortable position to sit on the desk, so she removed her heels and rested her feet on it. Her feet were perfectly pedicured, with her soft pastel teal nail polish being elegantly on match with her sheer tan hose.

"Oh, do you mind?" she said. Only then I noticed I was intensely staring at her feet.

"Oh, n-no, not at all, actually..."

***

"So...do you have a girlfriend?" she suddenly asked, interrupting the flow of the conversation.

"I...she kinda left me..."

She left the desk, came in front of my seat and held my hand. Her hand was warm and soft. She was close enough I could smell her delicate perfume "Oh, I'm so sorry Chris. Who would do such a thing to a guy like you?" she said while slightly looking down on me, being around 10cm taller than me.

"Oh, believe me Helen" my mother said, surprising us as she entered into the room "You would like the girl. She's a brilliant one, quite like you"

I looked at the clock and noticed that my lunch with Helen had been going for almost an hour and a half.

"Hope you two had a lovely time together"

"Oh, yes Grace, your son is a special boy" Helen said.

"You don't know how much..." she smiled.

"Now, Chris, I'd like you to come back, I have a pressing...issue you have to work on" she said, and I quickly got by her side.

I said goodbye to Helen, still charmed by her eyes, her wits, her perfume...her pantyhose...

I was quickly back in my mother's office. She closed the door shut and pointed her finger to her desk. I quickly knelt under it. She sat on the edge of her office chair and got close to me. She opened her legs and I saw her pantyhose had been ripped at the crotch. Did she do it...? She saw a questioning look on my face, but she ignored it. She put the slit of her wet panties aside and I met her drenched pussy.

"Quick, Chris, mommy's pussy is drooling..."

I got on my knees and plunged my mouth onto her, lapping and servicing her.

"Mommy got really horny during the break with Don...and all the while I kept thinking of my baby boy, always ready to fall on his knees for me...the man of the house..."

I kept exploring her pussy hungrily, feeling like a man. The man of the house. There I was: a moment I was flirting with Helen, the next one I was sucking the pussy of my exceptionally beautiful mother.

After but a couple minutes, though, I felt another taste in my mouth. I looked up at my mother and met her pleased gaze, piercing mine.

"Be sure to swallow it all...don't let anything spill..."

She was not cumming, not even close to her climax, yet her cum was already overflowing in my mouth. I felt the familiar mix, a part being similar to the wetness of her pussy, and then another, more dense, sweet, with a fishy aftertaste. She put her hand on the back of my head, pushing me further in. I reached my tongue deep into her hole, having to swallow quite frequently mouthfuls of her overflow.

"He sure let out a lot..." I thought I heard her whisper, but I couldn't quite be sure, with my head being squeezed between her thighs.

I suddenly heard the sound of her heels falling and I felt her feet on my crotch. "Unzip" she said. I hurried to obey, lowering my pants and revealing my girly see-though panties, a big stain of precum in the middle. She played with my scrotum with the back of her foot, while slowly stroking my dicklette through the panties with her other sole.

Click, click, click, she was typing on her desk phone, as if calling someone. Her feet felt amazing on my panties, her toes digging into my sack and wiggling on the head of my dicklette sending me shivers all along as she went up and down.

Was she going to ruin me or actually make me cum...?

"Mommy, c-can I make a piddle?" I asked, unsure if I actually had permission to cum.

"Shush, I'm making a call"

I breathed long and deep, trying to hold on as much as possible.

She said something I didn't hear on loudspeaker.

She kept stroking as she raised a foot on my face. I held her close to me, as I inhaled deeply under her toes, the sweet, sweaty scent bringing me a lot closer to my impending orgasm.

"Mommyyy please can I..." I groaned, my fantasies coming true as her toes stroke my dick.

Knock knock. The door opened. "Grace, you called?" Helen said.

My heart stopped.

She entered the room. My orgasm rose and rose, the strokes on my dicklette becoming firmer, the nylon of her toes massaging it through the sheer fabric of my frilly panties being unbearably erotic.

"Yes, I have the documents you wanted on my desk, take them" Grace said.

Then she looked down at me, under the desk, with a devious smile "...as for you Chris, it's ok, go ahead and make a piddle for mommy".

I heard Helen's footsteps come forward.

"Nononooooaaaah!"

I tried to suffocate my moans with mommy's foot on my mouth as she sent me over the edge of a massive orgasm, exploding inside my pretty panties, her toes massaging the head my dicklette all along, wave after wave of mind-melting bliss as I released my load inside my panties.

"Uuuughhhh"

I couldn't stop moaning, my whole body spasming in pleasure for interminable moments as I felt my hot cum spray out.