Sissy Office Training - Part 1

Your mother leads you through the front doors. A cool breeze of air hits you as you walk into the front reception area.

You immediately see the receptionist Sally talking to some other woman who looks like she works at the mailroom with a mailcrate next to her on wheels.

Sally looks like she's in her mid-40s with short brunette hair and glasses, while the mail clerk looks like she's in her late 20s, with blonde hair in a ponytail, khaki brown shorts ending right above her knees and a bright blue collared shirt with a mail bag over her shoulder - very plain but still showing off a hefty rack under her work shirt.

Sally cheerily says "Good morning Jennifer! Bringing a registered cocksleeve with you today again?"

Your mother answers "Yep, my son Marcus is going to be working under me most days from now on. I might be running him through some cocksleeve training today as well."

Your mother swipes her ID card at the desk and says "Uhmmm, I picked up a cocksleeve ID card for my son the other day I had requisitioned, let me just find it." and began rooting around her designer purse.

While your mother is checking, the receptionist says "And how are you enjoying working here so far cutiepie?"

You nervously answer "Uhhmm, it's good so far... uh.. everyone seems nice here.."

The mailroom lady sees the cum-stained and drenched front of your pants and playfully says in an English accent "Awww was someone excited to get out of the house and come work under his mummy today?" tousling your hair as she said it.

Your face went a bit red at this and you froze up not answering.

The mailroom lady turns to Sally and says "Dawww he's shy. He's just the cutest thing."

Your mother at that point gives up looking and answers "I'm sorry Sally, I must have left it on the bedside table. This little rascal woke me up this morning with a morning blowjob and got me all turned around", your mother rubbing your bottom as she says this.

Sally answers "Don't worry about it Jennifer, you're practically the boss around here." In a mock hushed tone she continues "though you might want to bring it next time or else your little cutiepie cocksleeve might get snatched up when you're not looking."

Your mother chuckles at this and says "Oh I'm not too worried, I already marked him over the weekend" and turns you around and lifts up your shirt to show the 2 futa the tramp stamp tattoo she gave you, saying "Mamma's Toy" with a crossed out "B" before the T.

Both women let out a scandalous "Mmnnnn", the mail girl visibly getting hard in her khaki pants looking like her growing bulge might break the zipper.

The receptionist says "Wow Jenn, what a lucky girl you've been." "I'll tell you what; let me give you a temporary badge and name tag." and she begins writing on something in black marker.

A moment later and she hands the badge and clip to your mother. She looks at it and gives a melodic laugh, turning to you to clip it onto your breast pocket. Once she backs up, you see it reads "Mamma's Toy" with your mother's employee ID number written underneath. It even had the crossed out "B" and everything, just making it more humiliating.

Your mother then continues "Okay ladies, me and Mamma's boy gotta head up to the office. See you later Sally, and.." "I'm sorry, I didn't catch your name.", speaking to the mail girl.

She says "Oh apologies, my name's Alice. I actually deliver your mail to you." She moves forward to shake your mother's hand and continues "they just changed my route, or else I would've popped my head in already to say Good day."

Your mother responds "Well maybe Marcus and I will see you later today."

She says back "sounds fabulous" as you both turn to leave, you being lead by your leash.

After a short ride in the elevator, where you could feel your mother's big elongated dick grinding up on you from behind through her pants and blouse, the doors open to your mother's floor. You could see several cubicles with office women of various ages and body types, a couple offices including your mother's near the middle, a conference room with three executive-looking women sitting at the end of the table discussing something, and several interns or assistants messing with the copy machine or doing several tasks around the office. Every now and then you saw big angry-looking bulges in some of the women's pants or skirts and one futa in particular looked like she might've been jerking off under her desk. She closed her eyes like she was trying to imagine something or maybe she was just about to cum.

As some of the women saw you walk from the elevator through the pathway around the cubicles, being led by your mother on your leash, you could see some of them stop what they were doing to hungrily stare at the two of you. You saw one woman biting her lower lip at her desk and passed another one walking by you, biting her finger with her cock hanging out the bottom of her pencil skirt. It seemed to be wrapped up in some fabric or silky lingerie, like some type of designer sock for her big penis.

As far as you could tell, you were the only male on this floor. Maybe you were allowed to be here since Jennifer was so far up the corporate ladder? You weren't sure, but you knew for a fact you'd be in big trouble right now if you weren't getting led around by your mommy on a leash, clearly already claimed as a personal fleshlight.

You turned the corner and were surprised to see a nicely dressed futa in a suit jacket pounding what might have been her young assistant or intern from behind. The girl bent over the desk had her blouse half-off in a disheveled manner and her pants around one of her ankles and heels, with her legs spread apart, taking it like some type of office whore.

As you passed by, right in front of them on your leash, you could see the woman receiving had a fairly small cock for a futa, maybe even a little smaller than yours. Jesus, did these women just want to dominate people with smaller dicks than them or was it just a coincidence?

The woman getting pounded had medium red hair falling out of a bun and had her hand over her mouth trying to suppress her breathly moans. She had some chub on her belly and love handles but was still smaller than most futa. The black haired woman behind her was picking up her rhythm and was really going to town on this poor futa girl.

The women doing the pounding saw you passing by on your mother's leash and gave one last big push forward, going as deep as she could and holding it, giving tiny humps while balls deep. Her eyes went half lidded, and... was she cumming???

You realized she was most definitely cumming and her eyes were fixed right on you. She grinned at you and blew you a kiss in a seductive way.

As you were mesmerized by the spectacle, you felt a tug on your collar and began walking forward.

Your mother said "c'mon baby, we gotta get you latched back on momma's cock."

You then approached her office, which was surrounded by three sides of large windows facing populated hallways and the rest of the office area. The back wall was mainly the same large windows pointing out to a view of the rest of the city, some tall trees and the parking lot down below.

You entered her office, waiting as your mother placed her purse on the desk and circled around to close the door. This didn't do much for privacy though since all the blinds were up and even the women who were just fucking could see you through Jennifer's office windows, the one woman still throwing you sidelong glances through the glass barrier.

Jennifer then sat down at her desk to log on to her computer, bringing you closer with the leash, standing on the other side of the desk.

You give her a nervous "uhmm mommy?"

She answers "Yes sweetie?"

"Can we maybe close the blinds?" You ask, already knowing the likely answer.

Your mother surprises you however and says "Ohh baby, are those other futa making you nervous with their eyes on you?"

You try to answer back in a language she'd understand, "Well maybe a little.. I feel like I do a better job at pleasuring your huge cock when I don't have to worry about other people watching.."

Jennifer responds "Aww it's so sweet you care about doing your best to suck mamma's cock." She continues more seriously "However baby, part of today's goal is sissy training for you, and mommy needs to know you'll be focused on suckling her big cock even when other people are watching." She adds "and even if other people are in the room or playing with your holes directly." "Do you understand baby boy?"

You answer defeated "yeah mommy".

She says "that's a good boy, now take those pants off and fold them over the couch, mamma wants you bottomless today."

She lets go of your leash so you can take your pants and underwear off and place them over on the arm of the couch in her office. Maybe they'll dry off before you leave. Your soft cock is dangling freely now, and in a building full of hung futa goddesses, your dick has never felt smaller.

As you turn around, you see your mother has again unzipped her pants so her cock is dangling out over her zipper. This time her balls are pulled out over her pants and panties, allowing for you to have complete access to her impressive package.

You then do your duty as your mother's personal fleshlight and walk around the table and get down on your knees in front of her.

She responds to this by spreading her legs enough to give you space to start licking every inch of her cock.

As you start licking her shaft, you feel her reach down and grab your leash again. She says "give momma's full balls a kiss." and pulls your leash towards her until the tip of your nose was pressed up into her big balls.

You already made this woman cum 3 times today, so you were actually a little surprised when you leaned forward to give the center of her ballsack a smooch, it felt swollen and full of a new load about to explode from her hardening cock. Your eyes widened a bit at this - your futa mommy was a total monster.

She then said "now mommy's left one"

And you repositioned your head to kiss her testicle on your left side.

She then said "now your other left." and yanked your leash over to her other side, so you wouldn't kiss the wrong one again.

You gave her left ball a big kiss nearly sucking it into your mouth and then you licked up from the bottom of her sack to the base of her shaft and then all the way up to her head in one motion, ending with you sucking/kissing the very tip where you tasted a glob of her pre-cum.

Jennifer says "OOooo that one gave mommy shivers. Good boy."

You beamed at the compliment as Jennifer continued "now get mamma's big dick in that mouth baby." She pulled the leash towards her while saying this, pulling your lips over your mother's shaft, already halfway up the length of her cock.

Suddenly you heard a "Rrrrrrrmmmm" and at the same time felt the sensation in your ass, as your mother likely just turned on the vibrate or massage function on your anal toy.

Your surprise was short lived however as your mommy continued pulling your leash so you were quickly approaching towards taking your mamma's big dick balls deep.

The vibrations of the plug were rapidly making you horny again even though you felt like you didn't have much more cum to give at the moment.

You were pulled down your mother's cock until your chin snuggly rested against her swollen ballsack. This feeling of fullness coupled with the vibrating plug was enough to start forcing your dick up, until you had close to a full erection again.

Your mother could sense your horniness as she tilted her body over to the side to reach a hand down to your cock. She grabbed at it brushing her fingers over your frenulum, illiciting a moan and feeling the first stimulation on your dick since breakfast.

She said "Good. No cummies baby." "The first sign that your little weewee has cum without my permission and you're going in your cage until this afternoon, maybe even tonight."

Your stomach drops a little at this announcement, knowing there was no way you could last until this afternoon. You were screwed.

You wonder if she knew that and was rigging the game before it even started..

Just then she increases the vibrations on your plug from low to medium-low and you felt your dick go rigid as a wooden plank. You were still gulping down the majority of your mommy's dick, going in and out a few inches at a time and massaging the bottom of her cock with your tongue.

It was unfortunate that your mother's desk didn't have a back to it, as anyone looking in the office could see you with a pink plug up your ass, getting lead to suck a big cock balls deep on a pink collar and leash. You must have looked like a real office slut and desk fleshlight. It probably resembled a scene from an extremely kinky porno, like one of the 'Boy Sluts' films you knew your sister Zoe had an entire shelf of at home. You knew there were likely several futa watching the kinky spectacle right now and some probably masturbating to it at their desks. Thank god you weren't leaving this building alone.

Just then your mother picks up the pace of her subtle humping and pulling your face forward on her cock.

She says "Okay honey, get ready for mamma's first load of the workday!"

You suckle and slurp her big cock and, trying your best to deep throat the anaconda in quick long intervals. She pulls you all the way to her balls, smooshing your chin and lower lip to her heavy balls full of her gooey baby batter.

You decide to reach out your tongue as far as it'd go, licking her smooth full balls and massaging your tongue from underneath them and all around, giving your mommy's nutsack the tongue bath it deserved.

She reacts intensely to this "Ohhh goddd baby boy, that's sooo fucking gooooddd!", hearing your mother swear so openly. She was also borderline screaming, so unless her office had soundproof glass or something, you were sure the whole floor could hear this mamma bear about to bust a giant load down her cub's throat.

You continue your tongue bath on your mommy's balls even more enthusiastically and she follows up with "Mmmnnngggghhh.. Mommy's about to cum!! Mommy's about to- uwhhhaaa hhaaahhhh" she was practically singing and letting out her own brand of orgasmic noises.

Just then you felt her balls pulse in your tongue and her big cock expand, and the next second a massive jet of sweet mommy cum was shooting out her balls, shaft and into the back of your throat at high velocity like a firehose. The first two jets feel like the cumshots may have genuinely shot down your throat too hard and left your esophagus a little raw, but it was worth it for that sexy intense reaction.

As shot after shot of thick creamy baby batter went down your throat, you could feel your own cock try to shoot off again. This blowjob was just wayyy too hot and you knew the vibrating buttplug was a huge problem as well.

On the 19th or so stream of mamma's cum, you could feel your cock about to burst, but you knew there'd be no hiding it this time if you came all over your mother's office floor. You pulled every bit of strength you had and held back from busting your little load on the floor.

By the time her orgasm was petering off, you got your libido under control and gulped down the last few wads of Jennifers thick batter.

She let out a deep slow breath and said "Whewww baby, you're getting better and better at milking mommy's loads right out of her sack." "At this rate I'm gonna be the one addicted to your pretty mouth and not the other way around."

She lets out another sigh and says "mamma's gonna do her best to fix that before we go home to your sisters though." lovingly petting your cheek, your mouth still stuffed to the brim with massive mommy meat.

You don't answer her as you're still trying to get a hold of yourself, but just then, she tilts down again to stretch her hand out to see if you had shot off your little cummy load. Her fingers softly and gently grab at your throbbing cock for less than a second, which is all the stimulation you needed to uncontrollably explode all over the floor and now your mommy's hand situated right on and in front of your cock.

You try to get out a quick very muffled "Mommy can i pleasseee cum!?" but before you can even finish muffling "Ahmmnny" with your mouth still stuffed balls deep, your own throbbing dick is already exploding over your mother's soft hand, which she still has not let go of and you instinctively hump forward into her hand and shoot at least three shots of your cum until she realizes whats happening and quickly pulls away, leaving your cock to flail up and down shooting at least 5 more shots of cum you would have never guessed you still had in you.

As your last jet of cum shoots out, barely catching any air, you could feel your mother's cock, at the same time, shoot one last stream of her own delicious jizz, gobbling it up like a $2 whore, enjoying your own release in the process.

As she starts pulling your head off her big dick, she brings her other hand up that was gently brushing your cock to initially check for accidents.

You slide off the tip of her cock with a loud *POPP* and your mother is holding her hand up that is now drenched in your own messy accidental load.

She looks at it, her face transitioning into an unhappy expression, and then quickly rolls her chair out to be 100% sure of what just happened. She immediately sees your dripping little dick and a shotgun splatter of cum on the floor originating from your spent penis.

She looks at you, the most angry and cross you've seen her all day. She lets out a low disapproving grrr "Mmrrrrrrmmm" and very loudly says "OHH UH UH!! You are in such BIG Trouble Mister!!!"

Everyone in the office, if they weren't already paying attention that is, turn there heads to see a slutty-looking sissy cocksleeve on the floor of your mother's office looking guiltily at his spent little male penis, while his big-dicked mother looked like she was ready to lock him up and throw away the key.