Sissy Office Training - Part 2: Cuckold Timeout

You watch in stunned silence as Gabby continued to lap at and suck on the tip of your mother's soft cock. You were first confused at what Gabby's purpose was for being here, but now that confusion turned into bubbling annoyance. Was this your mother's plan?? Make you watch as some office bimbo sucked her cock, and it was supposed to be some sort of punishment for you?

You inwardly scoffed and laughed thinking this was such a dumb plan by your mother, knowing it wouldn't accomplish anything except make your knees sore from sitting here. Well.. at least you got a free show, as some cute girl who looked like she belonged on the set of 'Full House' tried taking a monster cock that even you sometimes had trouble with.

You watch smugly as Gabby is licking your mother's shaft and the underside of her cock. You silently give her a sarcastic "good luck", seriously doubting whether this small girl would even be able to satisfy your mother's bottomless libido even a little.

Gabby reaches her hand down into your mother's pants to pull her huge balls out and starts gently fondling them as her lips are latched onto Jennifer's cockhead and you see Gabby's tongue swirling around the soft head in circles. Her lips suck in a bit more of the head and then you see her tongue playing with your mother's foreskin and licking every nook and cranny of the end of her dick.

The show is inadvertantly making your cock a bit tight in its confines, but you're still smirking at the notion that the small intern would be able to handle your mother's beast.

Just as you have that thought, you see your mother's dick slowly expanding and swiftly becoming semi-hard, already filling out Gabby's mouth. You lose a bit of your smug attitude at the sight of your mother getting hard so quickly. The next second, Gabby is sliding Jennifer's cock in her mouth and down her throat in one smooth motion, maybe making it 2/3rds of the way down your mother's cock in the first real pump of her mouth over Jennifer's dick. The irritating part was that Gabby made it look easy, and as the small girl pulled her mouth all the way to Jennifer's tip, licking her piss slit, she again gulped down your mother's dick taking it back down her throat and going and going and going.. and making it all the way until Jennifer's fat balls were snug against Gabby's chin. Gabby even stayed there with Jennifer's cock all the way down her tight throat and gently rocked her head from side to side, making loud gurlging sounds echo around the room. You thought you could see the bulge in Gabby's throat as she effectively became you mommy's literal cocksleeve, and at this thought, you had a surprising surge of emotions.

By the time Gabby pulled off her cock, you were seething with irritation and maybe deep down a bit of jealousy. What the hell?? Why were you even registered as your mother's cocksleeve if she had professional sex interns at her beck and call to begin with?? You weren't as much irritated someone else was sucking your mother's cock, but more so that you were put through all this when it was clear Jennifer had other options to relieve herself.

You close your eyes, try to clear your head and take a deep breath, reminding yourself that you didn't really want the job as your mother's cocksleeve to begin with and the position was initially **** upon you. You'd be way happier if you could just go back to having a normal life, so why should you care who sucks your mother's cock.

As your eyes are closed, you unwittingly don't notice as Jennifer, whose working on her computer, is grinning, knowing that her cocksleeve son was getting jealous at somebody besides him deep throating her giant motherly dong. Jennifer knew full-well she was a jealous woman, especially when it concerned her son, and she also knew full-well that she was a big fat hypocrite for actively making her boy stew in jealousy. She didn't care, cause she knew after today's sissy training, Marcus would be begging just to get a little taste of her fat cock and the idea of her son being her own personal needy slut excited her to no end.

Still caught up in trying to clear your thoughts, you hear your mother address Gabby "Mmmmm keep doing that with your tongue baby girl."

At the use of a pet name so close to the one she uses for you, you felt the first real pang of jealousy, unwanted as it may have been. You knew this was just a dumb game and somehow part of your mommy's 'training' though, so you again tried your best to ignore the annoying uninvited feelings. You kept telling yourself, only a few days ago, you wouldn't have given a shit at all, so why should you care now??

You looked up at the scene and saw that Gabby now had your mother completely erect and was masterfully sucking on the head of Jennifer's cock while massaging her shaft with both hands with fervor. You let out a low groan in frustration, not meaning for it to be heard by anybody but you.

Your mother says to you "Everything okay sweetie?" "You don't need a pillow for your legs or anything do you?"

Your legs were actually kind of sore, but you didn't want to give her the satisfaction, so you respond with a self-satisfied "Everything's perfect Mom" "Just enjoying the feeling of this plug giving me soothing pleasure. It's actually quite relaxing."

Your mother is silent for a second at this, and you think for just a moment you might've scored a point; instead you unexpectantly see a concerning devilish grin on her face that makes you inwardly sweat.

Your mother excitedly answers "Hmm.." "Well I'm glad you're enjoying yourself, because you just reminded me, I forgot to turn up the intensity for your punishment."

Just then, the low-medium vibrations on your buttplug shot up to medium, medium-high, and all the way to the max setting within the span of 2 seconds.

At the sudden change, you involuntarily moaned and even let out a girlish squeak. Your body slumped over grabbing at your caged cock, which had somehow felt the sensation coming from deep within your ass and prostate.

Your forehead now pushed up against the floor, you hear your mother smugly and cheerfully say "I'm glad you like the vibrations on your prostate massager so much baby, I'll have to make sure to order a stronger one next time I shop for toys for you." While she's talking, you can hear nonstop slurping and sucking sounds throughout the room, really proving Gabby's determination to be the top paid office whore.

Your mother bends over her desk and hits the intercom button "Hey Porsha, can you bring a big pillow in here for my darling boy to sit on. We don't want his precious little knees getting bruised." She releases the button, but then, as if just realizing she forgot something, she presses her finger back down on the intercom and says "oh and Porsha, apparently Marcus's plug isn't strong enough for his liking. Do you know the ETA on Big Bertha?"

A moment later, you hear back "Yes ma'am, the delivery crew just got here, I'll bring it in with a pillow."

You were still slumped over on the floor as if you were praying to the Goddess of Kama Sutra to send you a miracle to release you from your tiny pink cock cage. You were desperately trying to get used to the wild sensations happening in your body, when you hear the office door open and presumedly your mother's assistant has entered to give you a pillow and whatever "Big Bertha" is.

Porsha was a 30 something year old woman with her long blonde hair pulled back very tight in a ponytail to the point where her hair looked like that of a BDSM mistress. She had on stereotypically-shaped secretary glasses and a tablet under her arm. She also had a red collared shirt with the top few buttons undone, showing impressive cleavage, tucked into a black pencil skirt that cutoff midway up her thighs. You looked up from the floor to see she was carrying a large purple pillow, that might've been a doggy bed she snatched from another office.

You looked back down to Porsha's legs and saw she was wearing black stockings. Your position, hunched over on the floor, also awarded a front row view to her big swinging dick with the head reaching below the hem of her skirt. Just like you saw on another woman in the office earlier, it appeared Porsha was sporting some designer futa cock lingerie and even had something harnessed around her extremely large balls. Her balls were practically spilling out of the harness, and they were indeed far above the average size even for futas thus the red fabric of the lingerie looked like it could barely contain her impressive sack. You vaguely remember this type of futa lingerie being called ball-bras, as your mother already has several similar types of lingerie for her cock and balls at home.

You look up from under her skirt to see Porsha lock eyes with you from above. She's giving a knowing grin and gives a flirtatious wink in response.

She says "C'mon cutie, let's get you up and situated on something more comfortable."

Porsha's voice is like honey and might've had the barest hint of a Southern drawl to it. You collect your sex-tortured brains off the floor and stand up, so Porsha can lay down the pillow, which you're now very certain is almost definitely a doggy bed, thankfully without any hair on it.

Porsha then runs back over to the office door and waves someone in. She holds the door open as two large burley futa women heave some type of contraption through the door.

It looks like some type of turbo-charged sex machine with a colossal 2-foot dark brown dildo on the end that makes your eyes go wide and your stomach fill with fear, making you forget all about the beating your ass was taking. That was much much bigger than your mother's dick, and it looked like it was attached to a machine with an engine in it that could fit in a small car. You idly notice there are straps around the sides, making it seem like you were about to get strapped in while taking this giant fake cock doggy style.

The delivery women set the intimidating sex machine next to your "pillow" so the silicon cock was looming over it, making it clear exactly where you would be situated for all of this.

You could hear the sucking and slurping sounds of Gabby going to town on your mother's giant cock as the two large futa left. Still standing to the side with your leash dangling down behind you, you hear Jennifer say "Perfect! Now do you have those outfits Porsha? I'm worried this isn't going to be enough to teach Marcus some manners and proper humility."

Porsha answers "Yes ma'am" and quickly scurries out the door.

You could see through the office windows as she picked up a bundle of outfits on hangers and hastily came back through the door. You finally seem to take full awareness of all the eyes watching you from out in the rest of the office and have the urge to hide your exposed body, not to mention the shame of being locked in a tiny pink cage while a plug is vibrating up your ass. You close your eyes and take deep breaths, which only makes you focus on the slurping sounds from under Jennifer's desk.

As you open your eyes, you see Porsha holding up the clothes for your mother like some office presentation and says "Alright ma'am, first we have this pretty ensemble" and held up what was clearly a slutty maid outfit with a frilly apron on the front, which humiliated you just thinking about being dressed as a sissy maid and having to walk around the office floor taking out the trash and dusting desktops. You weren't sure you'd survive long if you left your mother's office unsupervised, even with her influence in the building.

Your mother makes a swiping motion with her hand, so Porsha continues "Next we have this cute kitten outfit, which is my personal favorite" and holds up a white outfit that is just a narrow top with a heart-shaped hole in the middle to show off cleavage and see-through white ruffled trim along the bottom of it and over the shoulder straps. The other part was just white panties with embroidered cat ears on the front and the same see-through sheer ruffled trim along the sides over the thigh area. You additionally recognized white fur cat ears on a headband attached to the hanger and a white tail that seemed to be connected to a decently-sized black buttplug, which appeared to be how the tail was worn.

Your mother chimes in "Ooo I like that one, but it would be a shame if Marcus couldn't wear the tail since his hole will be rather occupied." She then adds "show me the rest."

Porsha nods along and then holds up an extremely frilly pink and white short fairy dress that nearly looked like some tutu that would barely cover your ass and crotch, if at all. Going by the rose gold tiara attached to the hanger, it was some kind of perverted sissy princess costume. In addition to the dress, it also had frilly little armbands and thigh high white stockings with what appeared to be a pair of pink ruffled panties that seemed to only enhance the humiliation that would be felt by wearing this outfit. The thing had so many frills on it, you were sure it was designed for optimal humiliation of males the futa designer wanted to turn into whimpering sissies.

This might've been the worst one yet, and you thought to yourself in panic "Please don't pick this one, please don't pick this one..."

Your mother apparently could read your mind, because she instantly and excitedly says "I think we have a Winner!" and followed it with a domineering moan, while Gabby simultaneously gave a loud slurp.

At this point you're now taking note of all the horny futas outside the office glancing at you, and you're legitimately starting to lose it. You count at least 12 women watching you and not even hiding their enjoyment from the spectacle.

You decide it's now or never to speak up. You're afraid of what your mother might do next if you gave her backtalk, but you felt like this was going way too far.

You unthinkingly blurt out "Mommy please! This is too much!" "I don't think I can do this in front of all these people watching." "Can I please just go back to sucking your cock?" "I promise I'll be a good cocksleeve from now on..." and follow it up with a final and pleading "Pleassse...."

Your words, however, seem to fall on deaf ears as your mother gives a stern response "Marcus, maybe you should've thought of that before you disobeyed me earlier and didn't even try to hold back your little cumload" "I told you what would happen over and over again if you couldn't get a handle of your urges."

A bit of your anger bubbles up over how unfair this all was, so you instinctively say "That's not fair though! I can't help it if I cum sometimes and you were literally touching me when it happened, which is why I had an accident at all!" You were practically shouting now and you couldn't help but feel you were digging your own grave.

Your mother retorts "Young man, this was second time TODAY you came without my permission. I think I've been beyond patient as your mother and registered owner."

You try to add "But-"

"And most importantly!" Your mother interjects. "I felt you trying to hump my hand when you shot your little cummies earlier." "You must think your mommy's stupid huh?"

You try to say "No I-"

"You know what you did mister! You had the ability to at least try to resist, but instead you prioritized your own pleasure over that of mommy's." "You've been a selfish naughty brat all day and now you're in sissy timeout as punishment and you've got nobody to blame but yourself. You're just going to have to deal with it young man!"

This final lashing from your mother shut you right up and you felt like you had no good rebuttle for it. You weren't sure if you had the capability to stop yourself from cumming but you internally had to admit you wanted to cum in the moment and may have purposefully humped your mother's hand, but it was still an accident and you were trying to hold off your orgasm.

As you thought this over, you could hear the background "GLUCK GLUCK GLUCK.." noise of Gabby deepthroating your mother and you felt like you were about to cry with all the stress and emotions pressing down on you of having to get plowed in a sissy dress in front of so many office women. You felt the walls closing in and knew there was no way out of this.

Your mother again must have read your mind because she instantly says "Okay Marcus, I'm going to compromise with you just this once, since you seem to genuinely be having a tough time adjusting to the voyeuristic part of your job as my cocksleeve." She continues "But I'm going to say this right now, you need to eventually adjust to other futas watching you service your mother, no matter what the task is."

You nod along to this in panic and fear and then Jennifer continues with more "And in exchange for closing the blinds this one time, you're not going to complain, whine or moan. You're going to put on your pretty sissy princess dress, strap in to get fucked by Big Bertha and watch patiently as Gabby greedily slurps up all of mommy's delicious loads that you lost the right to eat".. "Do you understand mister?!"

You quickly answer "Yes mommy. I understand.." and then remember to add "Thank you mommy.."

As your conversation ends, Porsha is already beginning to close the blinds, and by the 2nd window, you could hear a whole group of futa by the water cooler grumble and loudly complain about missing the show when it was just getting good.

You stand there patiently with the max vibration whirring sounds tickling deep within your ass, as Porsha finishes lowering the last blinds. You were sure that if you didn't get dressed up or get fucked by this sex machine thing, your mother would happily raise the curtains back up as punishment for further disobedience.

You try your mother's patience one last time by asking if Porsha can also leave and your mother says "Marcus..! You're on thin ice young man."

After a moment, she then says "Porsha will leave after you're all ready and strapped in.. now shush, mommy's trying to give Gabby a taste of her creamy nectar."

You instinctually lick your lips at this remark, feeling jealousy that your positions aren't reversed, but resign yourself as Porsha picks up the insanely humiliating outfit and begins to pull it off the hanger for you.

First Porsha unhooks your leash, as you're not even being used by your mommy right now, then she takes the pink tutu frilly dress and pulls it over top your head and now matching pink collar. You look down and realize your pink cage also matches the color scheme and you notice it's on full display as the dress doesn't even come down past your hips. You look behind you and yep, the pink buttplug is also on display. You're suddenly extremely thankful you fought to close the blinds otherwise you might literally be dying right now of embarrassment. You felt Porsha's slender hands fitting the frilly armbands onto your forearms and realize you might just croak anyways from Porsha's presence alone.

You quietly groan to yourself in frustration and embarrassment. Porsha must have heard you though, because she coos to you "Aww sweetie, you have nothing to be ashamed about. Take it from me, this adorable outfit would drive any futa absolutely wild.

She steps forward so her pencil skirt and cock are pressed into the back of your thigh and ass. She says "You feel that sweetie? That's all from you" stroking your jaw line as she says this. You could indeed feel Porsha's hard cock as it's straining in her cock lingerie, the thin fabric of her cock sock the only thing between her big dick and your quivering ass, and you suddenly felt a bit better about the situation, at least to the point you didn't want to jump out a 7 story window.

Porsha pets the back of your hair and neck like she's trying to calm down a spooked animal and coos "shhhh" sounds at you. She then says "Now lift up your leg cutiepie and let's get these matching cute panties on you". You lift both legs into the holes and Porsha pulls up the pink ruffled panties to your waist after rustling them past your tiny pink cage. Porsha then surprises you by reaching her arm around to your cock and grabbing it through your panties. This makes you blush harder than when you felt her hard cock and whisper to her in panic "Porsha..??"

You then realize Porsha was pulling your cock cage out a designated opening in the front of the ruffled panties, which you don't know why you're surprised by. You just then realize the breezy feeling on your ass and look behind to see a huge hole cut out of the back of the panties totally exposing your asshole and much of your ass cheeks.

You sigh and let Porsha continue rolling up the thigh high white stockings on your legs that also have pink ribbons at the top, in case the outfit wasn't girly enough.

Porsha takes a step back and gives a whistle, to which you instinctively curl up in yourself like some bashful girl. You realize what you just did and become even more humiliated and cover your hands over your face and quietly groan.

It's at this moment, your mother sees you and the slurping sounds from Gabby having become complete throat fucking as Jennifer is nearly about to cum.

Your mother says "That's right baby girl! Take! My! Dick!" and explodes in Gabby's throat while giving a side glance to you as she said it.

You weren't sure if she was talking to you or Gabby but either way you just wanted to get this over with, so you walked over to the "Big Bertha" machine and waited for Porsha to set it up.

You were still highly afraid of the huge dildo on it, but by some miracle to the heavens Porsha walks up with a pale skin colored dildo maybe half the size and considerably smaller than your mother's cock, maybe 10 or 11 inches long with average thickness for that size.

Your mother says "Don't worry Marcus, you need to earn that big cock first, but I promise you, that new one is still going to be no cake walk." "We call that Big Bertha, but the official name for it is the "Male Pacifier 3000 and I think you can guess why."

You see Gabby laid out on her back on the floor with her mouth open and tongue nearly out of her mouth, and your mother must be giving her a break to get a close up look at your own humiliation.

Porsha finishes adjusting the 10 inch cock on it and are expecting her to guide you onto it, but your mother says "You can go now Porsha", to which Porsha replies "Yes ma'am" and reluctantly scurries out of the office.

As she leaves, you see several futas outside the door trying to get a peak inside the office as the door is closing back up.

Your mommy places a flat hand on your chest and the front of your sissy dress and then runs it down around your side and all the way to your ass to get a thumb and forefinger around your plug.

She says "Ohh baby boy, are you ready to get fucked and pacified like a good girl while mommy has lots of fun with her new cocksleeve?"

You close your eyes and groan slightly, trying not to let her stinging words get to you. You can't help it when you're dressed like such a little girl, while your mommy is essentially cuckolding you for her own pleasure. You didn't like it at all, but at the same time your cock was straining painfully against the walls of its cage and the vibrations in your ass made you wish desperately your mommy would just fuck you instead of some smaller silicon toy.

Your mother seems to notice your frustration and smiles reassuringly at your situation. She says "Mommy wants to see you learn to cum even when your locked in that tiny sissy cage." "This will be good practice baby so try to make the most of your punishment."

She slowly begins to pull the vibrating plug out of your ass, supposedly to make room for something much bigger. You let out suppressed moans and whimpers as she gets it out halfway and then feel the last of it squeezing out of your hole. You're surprised to feel an empty feeling from its disappearance, which just makes the urge for your mommy's cock even stronger, but you already know what's in store for you.

Your mother then says to you sweetly "Are you ready for your sissy pounding baby?"