Mommy Makes her Sissies Share a Pussy

Your mother has the purple doggy bed in her hands from earlier and lays it down on the open floor in a dry area away from the puddles of cum. You realize just now that she must've moved the floor pillow before you all started the messy bukkake party.

Once it's on the ground, your mother says to you and Gabby "Okay my babies, this is the last thing before I let you both clean up and take a break for a bit." "Now princess, I have an important question for you." After a short pause, she says "Do you want to get out of that tiny sissy cage locking up your clitty?"

You answer a bit too fast "Yes!". Though you immediately try to correct yourself, "I mean, yes please mommy.." you say in a nicer more submissive tone.

She says "Well you're going to get your chance to free yourself for the rest of the day baby, assuming you don't misbehave again later." "You just need to beat Gabby in a little 1 on 1 challenge. We'll make a fun game out of it." Your mother seemed excited and eager, which already gave you quite a bit of worry.

You give a confused look at her proposal, but your mother continues "Now I know your both probably tired and need a break, but you'll both be able to lay down on your backs for this and relax." "Except maybe *You shouldn't relax too much princess." She says this while locking eyes with you.

She continues further "Before I explain anything, I want you to both lay down, but before even that-" Your mother throws a white towel towards you, insinuating she wanted you to wipe as much cum off you as you could - Gabby too probably, since she got hit with a lot of splatter and ricochet while pounding your ass.

You take a few minutes wiping yourself off as best you can. It feels like drying yourself after a bath or shower given the huge amount of cum you were soaked in. Gabby uses a corner of the towel to wipe the cum off her own body, though she had far far less to worry about and looks perfectly clean and new by the time she's all done.

You, on the other hand, feel like no matter what, you couldn't get all the cum off of you. Your pink princess costume also looked beyond stained with cum, slowly drying on the fabric. You probably looked like Rapunzel after she had just pleasured an entire city in the town square, or Cinderella after she jerked off every cock at the Palace Ball.

Your mother chuckles at your messy cute dress and says "Sweetheart just take that off for now, it's only going to get in the way." She adds "You too Gabby, everything but the naughty bits."

A minute later, and you and Gabby had shedded all the kinky garments of your outfits so you stood there completely nake in nothing but a pink cock cage, while Gabby stood with just a white cat tailplug protruding from her asshole. You had honestly forgot she had been wearing it while she was railing you that entire time. The only other clothing you both wore were nearly matching white thigh high stockings that had coincidentally been a part of both of your costumes. The moment you tried to take them off, your mother told you to leave them so both her sissies matched in their cute stocking. Unfortunately, the only difference between your stockings and Gabby's was that yours had pink bows at the top, right above your knees where the stockings cut off, already making it seem like you were the bottom between the two of you.

Satisfied with your current state, your mother gestures for you both to step onto the doggy bed and says "Lay down on your backs and butts in the middle of the pillow. I want those cute little asses touching and legs criss-crossed over one another like you're scissoring."

You both awkwardly sit down and press your crotches together before laying down the rest of the way. Your mother says to Gabby "That's it baby girl, just pretend like you're about to scissor your eager little sister." You close your eyes tight in embarrassment, realizing this new position was somehow hitting pressure points of humiliation despite all the shit you had already been through today.

When you're both done situating, you and Gabby have the cracks of your asses smooshed against one another, your small cock and balls laying over your stomaches, except in your case, it's just a small pink cage sticking out the same as always. Both your white stocking clad legs were under and over one another, like you were in the most perverted game of footsie ever. Your mother definitely had you both looking like 2 sissy playthings, ready to amuse her.

Your mother then turns to you completely and says "Here's the deal baby. Mommy is about to unlock your frustrated little clitty." "Whether it stays unlocked it going to be entirely up to you however." She puts both her hands on her hips, long soft cock swaying between her legs and continues "Do you remember WHY you were put into sissy timeout young man?"

You hesitate for a moment and answer cautiously "Because.. I accidentally came on your hand?.."

Your mother glares at you expectantly, so you try to clarify further "I came without Mommy's permission.. a few times."

She says tersely "Anddd??.."

You quickly try to answer the rest "And umm... and I thrust into your hand cause I was being selfish and I'm sorry and please I've learned my lesson mommy! I swear!"

Your mix of a full confession and pathetic begging seems to satisfy her, so she continues "Hhmmph, well we're going to see just how sorry you are mister."

She says further "The rules are that you must hold those cute little cummies in as long as possible. If you can last longer than Gabby here, then you won't be locked back in your tight pink cage and your punishment will be over. If you're a good boy, you might never have to have your tiny cock locked up ever again. Wouldn't that be nice?" "However, if you blow your little baby load before Gabby, you will immediately be locked back up until Mommy says so or I think you've learned your lesson." "Any questions?" She directs her question to both of you.

Gabby says somewhat quietly "Umm.. if I lose, will I be locked up?.."

Your mother answers "No don't worry sweetheart, you didn't do anything wrong and there's no need to punish you." Gabby lets out a sigh of relief. She had never been subjected to chastity before but it seemed like the cage you had on wasn't easy to deal with. Your mother suddenly adds "HOWEVER, if I catch wind that you're purposefully letting my sissy cocksleeve of a son win, I will make you wear that tiny pink cage at work for a whole month!"

Gabby makes an "Eeep!" sound at that very serious threat. Clearly the thought had crossed her mind, as it seemed like she was growing a bit closer to you, as evidenced by her playing with your caged cock moments ago.

Gabby says "Okay, I promise I'll give it my all uhh.. mommy."

Your mother then reaches down to her own neck and bosom and pulls out a barely visible small necklace. She takes it off from over her head and holds up a tiny white key that seemed to be the key to your penile prison cell.

She then leans down over top her two adjoined sissies and grasps ahold of your pink cage to steady it. Unfortunately, the attention causes it to jump in her hand, trying its best to throb and break out of its confines.

Your mother says "Shhhh, calm yourself baby. I know your little princess clitty is frustrated, but show mommy how big and brave you can be for her."

You take a deep breath in and out, as your mother reaches down to insert the tiny key and unlock the first part of your cage. You hear a tiny *click* and then you feel the plastic sheeth begin to be pulled off your poor tortured penis. Your mother blows on your frustrated pulsing penis as she slowly inches the chastity off your mostly soft but swollen cock. You can feel your penis growing in real time as she shimmies the plastic sheethe off your length. Soon enough, the shaft and head pop free to reveal an already hardening chubby, about to become a throbbing boner.

Your mother lets out a low slightly annoyed growl and says "Baby, I didn't even get the whole thing off yet, control yourself!"

You take another deep breath as your mother's gentle fingers clinically grasp the base of your shaft and balls to pull off the bit encircling your base. Her fingers were already overstimulating you, making you hard and you highly doubted you could even last a full minute of any slight stimulation.

Once she pulls the last part of your chastity free, your cock immediately finishes becoming rock hard and throbbing into the sky. Your mother says "Hmmm I want to see you try harder than that little man."

You answer in barely contained lust "I'm trying mommy I swearrr. Everything feels so sensitive right noww."

Gabby is watching you from the other side of the doggy bed, biting her lip while staring at your small throbbing cock. Your mother says "Alright, well we better get started now then." She then leans over her desk and grabs a box, she opens and pulls out a pinkish purple squishy cylindrical thing.

Your mother says to you both "This is what we call an onahole, a lot like a pocket pussy.. or fleshlight.. not to be mistaken for a cute sissy cocksleeve like yourself though, but very similar nonetheless." She looks at you with the hint of a grin.

She says "We're going to pretend like this is your little girlfriend that you both share together." "See, she likes big cocks or at least normal sized cocks, but her two sissies have little tiny cocks that don't satisfy her, so she only let's you both make love to her when you put both your itty bitty cocks together so she can ride them at the same time." "She's quite the innovative young lady isn't she?"

This seemed like just more humiliation on the pier for you, but as you looked towards Gabby, her cock is completely hard just like yours, though for obviously different reasons. It seemed like your mother's humiliating roleplay was turning Gabby on quite a bit from what you could tell. You look at your mother and her cock is also becoming a bit hard as she continues giving life to her wild fantasies.

You hear a bottle squeeze out liquid and see your mother pouring lube directly into the toy's squishy hole. She puts the bottle back down and then lights spreads the lube on the end before continuing her talk.

"Now! Put those tiny sissy clitties together so your girlfriend.. mmm Jenny.. can try to satisfy herself by cramming those cocks in her at the same time.

Your asses already being smooshed together, it doesn't take much movement to press yours and Gabby's cocks together too. As you both lean a bit forwards, your balls begin pressing up against Gabby's for the first time. You gasp, feeling the stimulation shoot through your cock, making it throb and bob up and down as your balls were smooshed together.

Your mother holds up the onahole and says to you both "That's it little ones, your girlfriend here wants to see her two cute sissies snuggle their balls up to one another. Maybe if both of you shoot at the same time, they'll give her at least a normal sized cumshot." You hear Gabby let out a barely audible hiss and moan at the words, before your mother continues, "Also Jenny is really amused by how her one sissy looks like he's about to pop his little load just from a bit of ball cuddles."

Ignoring your mother's lewd and obscene comments, you try to push your cock up to meet Gabby's. Your mother again says "Mmmm it's like your sissy cocks are kissing and making out with each other. Jenny is so turned on right now and can't wait any longer to easily bury those cocks in her wet hungry snatch."

The moment the bottom of your shaft and head rubs up against the bottom of Gabby's hard smooth cock, you almost cum right then and there. You reflexively pull back to stop yourself from cumming right away, though you knew this would not go over well.

After a moment of not pushing your cock back to Gabby's, your mother says "Tsk tsk.. baby, your girlfriend needs both her sissy cocks, she's going to get quite angry if you don't press your little cocks together soon." "In fact, she might have to go out and find a big footlong Mommy-sized cock, tie her sissies up along with their little willies and make them watch her get fucked all night long by a big giant cock if you don't satisfy her soon." Your mother says in a whisper "That would be a Game Over sweetheart." clearly insinuating this would lead to you getting locked in your pink cage again.

Her lewd fantasies aren't helping to calm down your wild libido though, so after another few seconds of hesitating to continue, your mother walks over to her desk, pulls something out and then holds it up for both you and Gabby to see.

She says "If my precious sissies don't put their cocks together in the next ten seconds, Mommy, and by extension Jenny, is going to shove this big double dildo up both your asses and make your heinies snuggly meet in the middle." The tan skin-colored double dildo in question looked at least 9 inches big on both sides, maybe more, and pretty girthy.

With both of those very real threats made, you steel yourself and think of un-sexy thoughts, take deep breaths to **** your orgasm to subside and slowly press your cock back to frot and press up next to Gabby's dick, ready to take an onahole pussy together. You just hoped you could last.

You're trying real hard to keep your dick as frozen as possible, so not to overstimulate it by simply rubbing against Gabby's smooth cock even a little. However, you can feel Gabby's heartbeat through her member, as her cock ever so gently pulses against yours. By trying to keep your dick as still as possible, it seemed like it was making it even more sensitive and the tiny barely present touches and pulses from Gabby were stimulating you even more than if you were both stroking your cocks entirely. Even her breathing was making it seem like her cock was just barely brushing against yours with little micro-movements. The subtle sensitive touches and tingles on your cock was making your toes start to curl in your white stockings, and you try extremely hard to hold your orgasm back, feeling like you could pop at any moment.

Gabby clearly seemed to notice this as well, or was just simply turned on at the idea of both your cocks about to be plunged in a fake pussy together. Her breathing picking up only made the situation worse for you and harder to hold back your orgasm.

Your mother holds out the toy about a meter above your waiting cocks like she's readying to put on a show. She says "Okay my eager sissies, your girlfriend is ready to take those little cocks. She's going to lower herself onto them in five..."

You let out an involuntary whimper as Gabby's own excitement presses her cock up to yours even more in anticipation. Your shaky breathing picks up as your mother lowers the toy closer and says "fourrr..."

You close your eyes and try to think of something else entirely, before your mother says "threeee.."

You hear Gabby quietly moan across from you and her cock throbs excitedly against yours, making yours throb back.

"Twoooo.."

Both your cocks are involuntarily throbbing against one another. You can't help it yourself and its only drawing you to the edge of orgasm. Based on Gabby's own eager moans, she might've been in the same situation as you, at least you hoped that was the case, otherwise you were about to cum a lot sooner than her.

"Onnnneeeeee..."

You let out a half moan half whimper as you held back your orgasm with all your might, trying to ignore your cocks bouncing off one another as they throbbed against the underside of each of your shafts and heads.

Your mother punctuates the end of the countdown with eagerly saying "Here it comes!.."

As both you and Gabby flex each of your cocks up against one another, you suddenly feel a soft squishy wet object slowly touching your tip. It presses down onto your cock like you were pressing your cock into a plump soft butt cheek covered in lubricant. The pressure on your sensitive tip makes you whimper, toes curling trying to hold back your orgasm with all your focus. However, the moment the squishy toy snaps and pulls both your cocks into its slippery soft hole, your cocks squish together rubbing them from all sides of your head and tip from both the onahole and the warm cock below you. The part that really pushed you over the edge though was how Gabby's frenulum was smooshed right up against your own sensitive patch of skin that was your own frenulum. It sent tingles down your cock, across your body and suddenly the dam broke whether you wanted it or not.

The next moment after your cock heads penetrate the fake pussy, you let out a whiny "Nnnnnggghhhhh.." and begin cumming right into the end of the onahole and seemingly all over the tips of both of your relatively small cocks.

Gabby makes a satisfied moan as she realizes what's happening as warm fluids begin covering her throbbing cockhead.

Your mother then peaks her head around the toy and soon sees white goo seeping out the end of the toy and down along both of your's and Gabby's shafts. She says excitedly "My goodness! Some little sissy seems to have exploded in sheer excitement at the mere thought of penetrating a real pussy for once."

The irony of your mother's words was not lost on you, but all you could focus on was releasing your backed up balls now that you reached the point of no return.

After a few more shots of cum into the purplish pink onahole, you cover your hand over your eyes and face, realizing the consequences of your cumshot might be even worse than you thought given how fast you came.

Your mother, seeming to read your mind, says "Hmmm, it would seem my naughty sissy cocksleeve couldn't even last more than a full second before blowing his little load."

You groan into your hand in disappointment as your orgasm subsides and your mother continues humiliating you. She says "Looks like my baby boy will always and forever be a cute little quickshot."

She slowly pulls the onahole off your heads and then squats down next to your upper body. You still had one small round left in the chamber and end up shooting a mini wad of cum right onto Gabby's cock. The feeling of your load makes her cock throb up against yours again, right before you fully lie back to the ground again and your spent cock falls back against your stomach in defeat.

Your mother cups the side of your face in her hand and coos at your embarrassment. You take your other hand and cover your face completely with both hands, sighing at your predicament.

Your mother says to you in a loving tone "It's okay baby, I can tell you tried really hard this time to hold your little cummies back for Mommy. It only matters to me that you try your best to obey mama."

You sigh deeply into your hands again as your mother continues "Baby... Are you upset because you can't hold back your little loads?"

You say through your hands "I don't know.."

Your mother tries to comfort you again "Honey it's not the end of the world, this just means that your place in satisfying girls and Mommy especially is taking big penises up your tushie and in your cute little mouth." "Honestly, this was why mommy legally registered you under her to begin with, I thought it would be for your own good and to direct you on the right path."

You sigh in frustration and say to her "I was just locked in chastity for the last several hours, I can still have sex fine.."

Your mother says comfortingly "Sure you can sweetie, that's the spirit."

You say "The thing is.." and take your hands off your face to look at your mother, "Do I really have to get locked in that pink plastic thing again?.."

Your mother says more sternly "Sweetie, I can't just waive your punishment because you asked nicely, this is for your own good and you have to learn some time that life isn't always fair."

You let out an annoyed sigh and grumble, but quickly stop before your mother gets angry. Noticing your frustration and still mostly in her caring-mommy mode, she says "However.. I do recognize that your little willy was just denied orgasm for quite awhile and maybe you should be given one more chance." "I suppose since Gabby just came in your plump little butt, it would be fair to let you cum too before squaring off with her."

She looks to Gabby and says "Is that okay with you honey?"

Gabby nods enthusiastically, clearly on your side in the matter and wanting you to succeed.

Your mother then stands back up and seems to get back into character. She says "Alright then, since one of my little sissies was a bit too eager, Mommy is going to issue a punishment so you can both try again."

She slowly reaches over and holds up the double dildo. She holds it ceremonially for a moment, insinuating what your "punishment" is and then takes the bottle of lube and squirts it in excess over each end of the dildo.

She says "You're lucky mommy is so nice to lube this up before shoving it up your cute little asses."

Gabby says to her "Thank you mommy", which prods you to repeat it yourself.

She then squats down next to your adjoined asses and motions for you both to back up a little.

Once there's enough room, she first slides a bit of one end into Gabby's pussy. Gabby moans as your mother teases her with the end of it. She says "Do you want this in your tight pussy or your needy little asshole?"

Gabby bites her lower lip and then quietly says "..asshole please."

Your mother smiles at her answer and says "That's a good girl."

She pulls the end out of her pussy and then pushes it easily into her ass, illiciting even more moans from Gabby.

She pushes most of the one side into Gabby's ass and then positions the other end to line up with your own winking hole.

She says "Here it comes baby. Deep breath and then relax and let it go when I push in. Just imagine it's Mommy's cock and it'll be a piece of cake."

You briefly think about the fact that her dick was bigger and way girthier than this thing before deeply breathing in.

You feel the tip prod your hole and then as ordered, you let out a deep breath as your mother pushes it into your relaxing hole. You whimper as the somewhat large dildo is inserted nearly the whole way into you.

By the time your mother stops, there is only about 2 to 4 inches of space separating your's and Gabby's asses and cheeks from one another.

Your mother says "Your going to have to squeeze in tight sissies, otherwise your little cocks won't be close enough together for your girlfriend to sit on." She emphasizes this by grabbing the dildo in the middle and giving it a little shake and then slightly sliding it back and forth, making both you and Gabby moan and whimper.

Then, with your mother guiding you to push together with a hand on each of your thighs, you and Gabby slowly lift your butts off the ground to try to squeeze in the rest of the way. You both moan as you push the rest of the way and your ass cheeks touch and smoosh together yet again, but this time with a giant dildo connecting you both by the assholes, almost like a reverse chinese finger trap.

With both of you laying on your backs, your mother then leans down to forcibly smoosh both your cocks together in her hand. When you first began fitting the dildo into your ass, your cock was still soft, but after pressing up against Gabby again, your cock is slowly hardening. Feeling your mother's fingers smooshing your cock up against's Gabby's still rock hard cock only makes you grow even more.

By the time your mother begins counting down again for your "girlfriend" to "sit on you", your cock is now fully hard and throbbing against Gabby's dick once more.

You hear her say "Twoooo..."

Gabby pushes against you and the double sided dildo in excitement and you whimper again before you hear "Onnneeeee.."

You quickly prepare yourself, readying to hold back another orgasm so things go a bit differently this time.

You suddenly feel the onahole squish around the head of your penis again and after a second, both your cock heads are in the lubed cummy end of the toy again. Your mother lets out a satisfied moan "Mmmmmm.." and says "Your girlfriend loves feeling both her sissies inside her at the same time." as she pushes the fake pussy down around your shafts, all the way until it presses up against your pelvis. Your mother keeps forcing the flexible toy down over your cocks, scrunching it up and squishing it down over your shafts as far as it'd go, but neither of your cocks come out the other side, emphasizing yet again that neither of your penises are very big.

She lets the toy sit on both of your cocks comfortably for a few seconds. Your cock throbs against Gabby's and hers throbs in response. Thankfully, you don't even feel close to another orgasm, showing that your quick cumshot was, in fact, just a side-effect of being denied in chastity all morning. You already knew this, but you felt relief anyways.

Soon enough, your mother begins stroking the onahole over both your dicks, causing squelching sounds each time she pulls it up and each time she glides it down over both of your lengths until it reaches your pelvises.

Your mother says "Mmmmm your girlfriend might actually cum this time if both her sissies can last a bit longer. I guess we'll see who will pop first this time."

It isn't long until Gabby starts breathing heavy and begins rubbing her ass and balls along yours for extra stimulation. This causes both of you to moan, feeling like your whole lower body was being pleasured in every way.

Gabby begins moaning even louder and her eyes involuntarily look up to her hair and mouth open in pleasure.

To your alarm, she begins bucking up into the squishy toy, which has the added ability of pleasuring both of you, since both the dildo is grinding into you between both your asses and Gabby's cock is rubbing up and down against the underside of yours, whether you move or not.

The fact that you weren't the one instigating the movement, probably made it even more stimulating making it feel like someone else was playing with your cock and ass. You half-shout to the girl "Gabby wait-"

Gabby isn't listening though, she's too caught up in her own pleasure to register your words.

You say again "Gabby! Please slow down!.."

Suddenly you feel like you're yet again fighting the urge to cum, right back where you started so to speak.

You might feel less backed up as before, but this time both your cock and ass are being massaged and milked in a pretty overwhelming way.

Your soon showing your battle on the outside too as you moan and mewl "Mmmnnggh", catching your mother's eye, as before she was mainly watching Gabby bucking up into the toy.

Your mother says "Hold it in baby! Your doing so good this time. I think Gabby's really close." As she says this, you hear Gabby making lewd panting noises like a desperately horny mutt humping a leg and wanting to cum really bad, except in this scenario the leg was your own cock and ass Gabby was getting off on.

Gabby's bucking only gets more and more enthusiastic until your mother isn't even pumping the onahole over your cocks anymore, she's just letting Gabby do all the work.

You feel like your ass is getting pumped and grinded by a dick while you were sharing a pussy with the most enthusiastic perverted futa, who was bullying your own cock into submission while both lodged in the same pussy. You tried not to think about it, but Gabby was, in fact, milking your cock by just rubbing it and frotting against you, causing the onahole to rub around your cock as well, whether your mother was moving it or not.

The cock frotting against you was so smooth and slippery, it was sending tingling sensations up your body. You plead with Gabby again "Please slow down! I-"

Your face scrunches up as you try to hold back an orgasm, but even if you could hold it back, Gabby doesn't stop or slow down one bit. You shout out "..noooo.. Nnnngghhh!" Your cock yet again shoots your creamy load all over both of your cocks inside the onahole.

Gabby still doesn't stop frotting against you, so the cummy mess is only used as more lubricant for the hypnotized girl pumping her cock up against yours.

Your mother says to you "Oh honey.. you didn't.." you continue cumming into the onahole as she continues "baby, I won't be able to give you another pass this time, I'm sorry sweetie."

You continue moaning as you squirt more and more into the tight space, "Mmmnnnghh". Your mother gives you a warm smile, places a hand on your stomach and says "That's it baby, get all those nasty cummies out before mommy locks you back in your cage."

Your moans transform into a groan as your mother reminds you where your cock is now going after all this.

Your cock squirts out it's last two small loads as your orgasm begins to subside. A moment later and your breathing heavily in relief, while your cock is overstimulated, still getting rubbed against Gabby's slippery cock and the onahole.

You move your hand down to the toy and motion to pull your cock out of the fake pussy before your mother suddenly says "No no no! Do not pull your little willy out of there young man! You're going to sit there and think about what you've done while Gabby finishes off your girlfriend for the both of you!"

You're taken aback by your mother, but you suppose you really shouldn't have been. Your cock was already extremely sensative and uncomfortable having to let Gabby smash against it inside the onahole.

As your cock continues to soften, you grit your teeth and let out hard breaths and whimpers as you try to storm the torturous overstimulation. It suddenly feels like Gabby's cock gets twice as big and begins bullying your shrinking floppy cock in the squishy toy. She's not even frotting against you as much as just pounding and grinding your soft cock into the ridges and side of the onahole. It's like she's using you as a pillow to bully and grind her big cock on top of until she could cum from it.

You say to your mother in desperation "Please mommy, let me pull it out! This is too much!". She only looks at you and says sternly "Nuh uh sweetie. I gave you two chances and you still came before Gabby both times. I want you to sit and watch Gabby fuck your girlfriend and feel her big powerful adult cock on your soft little baby one. Pay attention and maybe you'll learn just a bit about how to pleasure a pussy, though I doubt it."

Okay.. you began to feel like your mother's roleplay was going a bit too far all of a sudden. One second she's loving and motherly and the next second she's mean-spirited and humiliates you and your pride, whatever's left of it at least. You supposed the humiliation could be exciting at times, but sometimes it seems like she just goes way too far.

After what seemed like several minutes of gritting your teeth to the overstimulation, Gabby soon changes up her rhythm and starts grinding her ass in circles on the double dildo, making your end of the dildo explore your asshole, along with her dick now rubbing against you in little circles.

This sparks your mother to start slowly moving the onahole up and down again in very slow sensual motions. You look at Gabby's face and she seems lost in her pleasure, biting her lip and her face red and flushed as she takes slow deep breaths.

It's at this moment, she grinds the dildo into you so it rubs across your prostate, surprising you and letting out a deep gutteral moan. Despite being enthralled in her pleasure, Gabby must've sensed your pleasure and felt your ass shaking against her as your prostate was stimulated, because the next second she's grinding on the dildo in the same exact manner so to try and illicit the same reaction from you.

After a few tries, she manages to succeed again and you're moaning yet again at her pressing the double dildo into your ass on your button. She starts to just focus on this movement, and you lean your head back and arch your back as she grinds and milks your prostrate with nothing but her own ass and hips.

Before you even noticed it, your cock is nearly rock hard again, stretching out the onahole alongside Gabby's still throbbing cock. You couldn't believe Gabby was still going. She might have a similar cock size as you, but she definitely still had the stamina of a futanari.

Gabby continues grinding the dildo into your ass, making you feel so good that now you even start bucking up into the onahole a bit. Your mother says "Oh my! Looks like my sissies are finally earning their keep. I think you're both close to shooting your little loads this time. Your girlfriend seems to be right there with you."

As you and Gabby continue bucking into the onahole, moaning and mewling as you get close to climax, your mother starts pumping the onahole in fast short motions. She says "Your girlfriend wants all three of you to cum together." "Ready?.. Five.."

You moan at the insinuation, knowing your cock was ready to explode again at any moment.

"Fourrrrr.."

Gabby grinds HARD into your ass, making herself moan in absolute pleasure "Hhnnnghhh"

"Threeee.."

Gabby pushes into your ass again grinding the dildo into your prostate in what seems like a final climactic motion, shooting sensations up your body that start in your ass and make you feel like you need to pee out your hard throbbing cock.

You realize Gabby pushed you over the edge and you were having an anal orgasm. You moan wildly as your whole body squirms and shakes around the 9 inch dildo inside you.

"Twoooo.."

The sensations build in your body and then focus into your crotch. Suddenly your shooting into the fake pussy yet again and still bucking up to add more cum to cover your throbbing cocks even more.

Your mother says in mock disappointment "Oh baby... such a naughty boy."

She continues to announce "Onneeee!"

She says "Finish your girlfriend off for the both of you Gabby. Your sissy partner is all tuckered out, so pump extra hard and make her cum with just your powerful bull cock."

You feel Gabby's balls pulse, her cock throb against yours and suddenly she screams "Huhhhnnnggghhh" as she releases a huge load into the fake pussy, making you feel like the onahole was suddenly submerged in girl cum. A squirt of white cream flies out the top and all over your mother's hand and top of the toy.

Your own cock is still cumming as well, but you're certain the torrent of cum squirting out the top has nothing to do with you. You continue to squirm and buck as you ride your anal orgasm. You feel Gabby cum again and another big squirt launches out the top of the toy, even higher this time.

Your mother says to Gabby "That's it sweetie, bust that big powerful load into your girlfriend and fill her to the brim."

Gabby cums a few more times until the cum is flowing out the bottom and covering both your shafts and pooling around your hugging balls. As your orgasm begins to die down, the cum from Gabby's end continues to flow down the toy and is now leaking down to your asses, pooling around your cheeks and running down the double dildo. You could even feel her cum running down the dildo and trying to seep into your ass.

Her orgasm continues, feeling her balls and cock pulse and throb a countless number of times.

After an unknown amount of time and a whole lot of cum, her body gives one final shake and then relaxes in absolute bliss, running her hands over her body and breasts.

Your mother chuckles at the scene and says "Wow, that was a lot of cum for your girlfriend's little pussy. She thinks maybe next time she might just have Gabby fuck her all on her own and maybe princess could sit to the side of the bed as you watch Gabby impregnate your girlfriend without you. What do you think baby?"

You roll your eyes and let out an annoyed sigh as you say "Whatever.."

Your mother says a bit more seriously "If you keep that attitude going, she might just have to tie you up and sit you down on a big vibrating cock while you watch."

You answer in a sarcastic tone "Sorry mommy, you're right my tiny cock would be useless and I'd only be happy watching and getting my ass destroyed in the corner."

She says sternely but also a bit amused "Well! Someone is a bit fussy cause they have to go back in sissy timeout."

She pulls your softening cock out of the onahole with a squelching sound, releasing and dribbling even more cum over both your cocks and balls. She then lays the onahole, still attached to Gabby's cock, on the girl's stomach, letting her lay sleeping on the ground with her spent cock inside the messy well-used toy.

Your mother continues in a playful voice "And here I was thinking you would just go back in chastity, but I'd still let you cum freely. I was going to compromise with you, but if you're just going to be a brat, you might have to go back in sissy cuck timeout after all."

You look up at her and lock eyes. After a moment of introspection, you say "I'm sorry for being a brat mommy. Please let me cum again.."

She says "I don't know, that didn't sound very pleading"

You sigh and say a bit more pathetically "pleeasssee don't put me back in sissy timeout mommy. I swear I've learned my lesson, and I promise to be a good boy."

She says back "You already are my good boy baby. Now stand up so mommy can put your pink cage back on that little clitty."

You inwardly groan, but carefully pull the double dildo out of your ass and separate from Gabby so it's half sticking out of her ass and prone body covered in cum and sweat.

You whimper as you squeeze your slightly gaping hole, still slick with Gabby's cum from earlier. You stand up and your mother leans forward, pink cage already in her hand.

She locks you back up and clicks the little padlock back on.

You ask her "How much longer do you think I have to wear this mommy?"

She says "We'll see baby. At least until momma has a turn with your ass." She emphasizes this by reaching around your body and squeezing your plump ass cheek.

This put all kinds of lewd thoughts and images into your head, but you shook them away as you suddenly thought of something.

You say "Hey was I always supposed to lose this challenge with Gabby? You make it sound like you set me up to lose and this was all part of your plan from the beginning."

Your mother doesn't even flinch and says "Your such a clever boy, you know that." She cups your face lovingly and continues, "But no sweetie. I suspected you might not win, Gabby is still a futa after all, but that is why I gave you *two chances if you recall. And even if I gave you a third chance, you still would've lost baby. I saw you blow your little load at the end a second before Gabby. I was being more than fair mister."

She then takes a more assertive tone and says "Okay then, I want you and Gabby to go clean up and then maybe you can take a little rest for a bit."

She continues "Now see if you can wake up Gabby and ask her to take you to the shower facilities."