A Sissy For Mom And Sister Ch 03

CHAPTER 3.

"How did baby sleep last night?" I hear my mom's voice calmly say.

"Good Mom, what's for breakfast?" I ask.

"Ok sweetie, A few ground rules. I've read the 'Age Play Guide' again, and this is what's going to happen. You will only call me 'mommy' for now on. During your daily activities, you won't speak unless spoken to, and will mainly use 1 or two word sentences. If you need to talk to me about important stuff, we can have some normal dialogue, only if I approve.

"Even though you're an adult, your sister will be like another carer, or mother figure to you, so you will talk to her the same as you do me. As per the guide, you will wear your pull-ups at all times, and we will embarrass the hell out of you about this, and your...tiny little problem," Mom explains, while rubbing the front of my pull ups. Remember, the very things that embarrass you the most, will eventually give you pleasure.

"You will do everything we ask of you, otherwise you will be punished. I give Carly full authority over you, and I consent to any punishments she sees fit while I'm out.

"This doesn't have to be forever, Sammy, and we will work through this, so the more you lean into it, the quicker it'll be. The rest we'll work out on the way."

"Mommy," I say, sitting up in bed. "I will try my best to do what you want, but please don't make me do this in public."

"Oh don't worry Sammy, it'll mainly be around the house with Carly and myself."

Mainly? That's not quite what I was hoping for. How am I supposed to wear my pull-ups out in public without anyone knowing.

"Ok, you're all wet, Mommy is going to change you now, and we need to take this big dress off you, that's mommy's," she says with a giggle.

Wow, mom is being so dominant. I kind of enjoy her bossing me around, but I'm not sure about being treated like a baby for an undisclosed amount of time.

Mommy drags the sheets down and pulls the soft white nightie up over my head. She lifts my legs up and puts a towel under me. I hear the material on the fluffy white diaper being pulled at as she slowly pulls them off.

"Oh you've done big wee's, lets get you all cleaned up," Mom says in a cute voice.

She wipes my squashed little penis with a wet wipe and starts massaging some cream over my little parts.

"Did all that wee come from this tiny little thing?" She ask's while her fingers coat me in baby oil.

Mom gets another handful of baby oil and rubs it up my chest and around my small, puffy nipples. She puts another diaper on me, dresses me in a tight, white singlet, and holds my hand as I walk downstairs.

"See, was that so bad?" Asks mommy.

I look up and try to give her a smile. It probably wasn't too bad I thought, but now I have to face my sister. She LOVES doing role-play, so I can only imagine what she is scheming.

"Oh Sammy, you're awake!" Carly says, running over to hug me. She's wearing one of my t-shirts and I feel her perky little boobs pressing against me.

"Mommy has work today, so it's just me and you. I'll be like your babysitter haha," She says.

I'm not sure how I feel about that, but it looks like I don't really have a choice.

"Ok Sweetie, time for your breaky," mom says, guiding me towards the table.

I eat the Wheaties while my sister feeds me, making aeroplane noises. She's really getting into this. I laugh a little at first at her silly sound effects. The first laugh I've had in a long time, actually.

"I think little Sammy likes this," Carly says.

I give her an embarrassed smile.

I feel like I need to go to the bathroom again, so I look in the direction of the bathroom and start to get up. That is, until I feel a firm hand on my shoulder.

"Does little Sammy need wee's?" Carly asks, in a ridiculing voice.

I nod my head. I think I know where this is heading.

"You've got to tell us when you need to go Sammy. This is like when we had to do this last time. If you ever want to get out of these diapers, you need to tell us when you need to go wee's," Carly says in a condescending voice.

I'm red in the face with embarrassment, a new kind of embarrassment. We hadn't spoken of my bed wetting for a long time, for very good reason.

With the aim of quelling the incontinence dialogue, "Wee-wee's," I say, looking up at my sister. I feel a slightly warm feeling as I wet the inside of my baby diaper.

As an adult, there is not much that is more belittling than having to tell your sister you are doing 'wee wee's' in a diaper.

"Ok sweetie, I'm off to work. You be a good boy for your big sister, and mommy will bring home a special treat," Mom says, leaning in to kiss me on the forehead.

"Bye Mommy," I let out.

"Awwww that's so cute," Carly says, milking whatever this is for all it is worth.

The door shuts behind Mom and I hear her car start up.

"We have such a fun day coming up Sammy, I'm sure you're going to love it. But first we need to change your diaper. Come with me," Carly says.

Already, I think? I guess I had just wee'd in there.

We walk over to the lounge and she lays me down on the large change mat.

"Can baby lift their legs up for big sister?" Carly says in a funny voice, pulling my diaper off.

I reach down and grab her hand, "I'll do this to please mom, Carly, but I'm NOT doing this for your entertainment all day while she's out!"

I feel a sharp pinch on my little balls as her nails dig in.

"Oww, what the fuck Carly," I yell. Another sharp pinch and then a very firm squeeze.

"OWWW!" I yell again. I feel her other hand move up and squeeze my sensitive nipples, and I yelp again.

"Sammy," she says calmly. "Mom has told you to listen to me as an adult and your carer when she is out, and I have permission to punish you how I see fit," she says, hovering over me.

I feel her firm grip on my thigh now and realise she is probably slightly stronger than me.

"So, any more of that and I'll send the photo of us in the change room, trying on matching pink panties, to everyone you know. I even have a screenshot of your comparison photos from the doctor. Your teeny tiny baby dick and peeny balls, next to that nice thick cocked man, and his big firm balls. Both photos have clear shots of your face too."

I think of many things to say, but "ok" Is all I manage, feeling deflated and little defeated.

"You're going to do all the things I want you to do today, until mom gets home, and I'm thinking of some REALLY good things," Carly says.

I think about my teeny balls aching, and my sensitive, pink nipples, stinging from her attack, and I nod in compliance.

"First we have to make sure you're all clean and healthy. Mom says you haven't done poopies since your accident. So, we're going to head upstairs and put you in the bath. I'm going to give you an enema to help clean you out, come along now," Carly says, gesturing to take her hand.

This reminded me of our childhood, when she would always want to play doctors and dress ups with me, only this seemed way more intense.

I kneel in the bath and feel her drip something cold on my clenched rear passage.

"Now I'm going to squirt some water inside you, and you're going to try and hold it as long as you can. We'll repeat that a few times and then we'll be done."

I wince when I feel a soft object being pushed firmly inside me.

"Relax your bum, and let big sis take care of you," she says, as I feel warm water flooding my insides.

I let out a long, high pitched moan, feeling my insides slowly filling up, and after a few seconds, she finally pulls the rubber nozzle out. How long has my voice sounded like that? It felt squeaky and high for some reason.

"That's it, hold it now," my sister tells me, rubbing her gloved hand on the back of my neck.

I feel so full that my stomach is slightly bulging. After what seems like an hour (probably 5 mins), I start moaning again and realise I can no longer hold it. My sister takes a step back and points to the toilet.

"Ok little Sammy, hop up on the big boys potty and you can let it go now."

I close my eyes, instantly relax and let out all the water that flooded my insides.

"Good job, now back in the bath," Carly says.

I get down on all fours again and she slides two lubricated fingers into my tight little passage. She works them in and out a few times.

"Wow such a tight little boy. I wonder what we can do about that," she says with a slightly maniacal laugh.

Oh god, I can only guess what is running through her head. She could be so nice at times, and equally as mean to me when Mom was out, the same as our childhood. She had definitely stepped it up a few levels though.

After two more rounds of this, I found myself feeling a bit weak and shaky in the bath. Surely it was nearly done, do I dare ask and risk further punishment? Not while I'm on all fours with my bum up in the air and a belly full of water.

"I.. I'm not feeling well," I murmur.

"Well you've been clean since the first one, I just wanted to see how much you could take. You can let this one go in the bath now," She firmly says.

Carly slides two gloved fingers inside me as if trying to stretch me open a little. My legs start shaking and I feel an intense, involuntary pushing from deep inside me. Almost a contraction-like push, if I had to describe it.

I feel a wave of relief and an intense type of (almost) pleasure, as I feel my body pushing harder and harder, without trying. I don't know if this is some kind of semi-climax, or just my body showing me that it is relieved.

Then I hear those words again. "Good little girl, you're being such a good little sissy for me now".

I take a while to regather myself and hop out of the bath.

"You've been really good Sammy, I think you deserve some diaper-free time now," Carly says with a smile on her face.

I wasn't expecting that, but it sounds good, I think to myself, as my sister dries me off with a towel. She then leads me by the hand through the doorway of her room.

"Ok Sammy, big sis is going to play dress ups with you now."

I stop, let go of her hand, and roll my eyes in distaste.

"OWWW!" I squeal, feeling the stiff prongs of her hairbrush on my right bum cheek.

"OK, OK," I say, walking a little further into her room.

I hear the brush whoosh through the air again before it lands again on my bare bottom.

"You will say 'yes big sis' when I tell you to do something. Not, ok, ok," Carly says commandingly.

"Yes big sis," I let out, with almost a tear in my eye. God that hurt. I look down at my butt in her mirror and see hundreds of red dots coming to the surface.

"OK we're going to play a game called big sissy and little sissy," Carly says, reaching into her underwear drawer.

"The little sissy must impress big sissy. She has to get fully dressed in big sissy's clothes, and must guess what I think will look best, then put it on. If she guesses incorrectly, she will be punished with the hairbrush... or other things more humiliating," she says with a wicked smile.

I go over to her draw and start to look through them. There has to be 40 pairs of panties and thongs in there. I know she probably doesn't want me in any of her plain stuff. I can tell she is aiming to humiliate me, so I rifle through and find a red lacy thong.

*WHACK* on my bum. Aww God it stings! I dig through and pull out a pair of pink panties with love hearts on them.

*WHACK*. I wince and close my eyes to try and block out the stinging on my backside. She decides to give me a little hint and nods her head over to her dirty clothes basket. I reach in and grab a black satin thong out.

"Smell it," she directs. I give her my most reluctant look.

"I've seen you do that to mom's panties before, go on, do the same to mine," she instructs.

I bring them up to my nose and see a big patch of white, sticky paste in the crotch. It smells similar to moms when the smell is stronger and little different.

I hate these games, but at the same time, this feels so taboo, so wrong. I feel my tiny little penis flinch out a bit.

"Oh does little sissy like that? Is it making her tiny little clit hard?" Carly ask's.

I pause and look down at my crotch, taking onboard her description. She lifts her hair brush when I don't answer.

"Yes big sis," I say quietly.

"Yes What?" she barks back.

"Yes, I like smelling your worn panties big sis. It makes my little...... Thing throb," I say, feeling humiliated. I can't bring myself to call it what she calls it, that's too far and I think she realises.

"Good sissy, now put them on and look for your next item to wear," she commands.

I slide the soft satin up my smooth legs, and pull the elastic waist up to my hips. The back wedges snug between my cheeks, and the front pulls my tiny penis in almost flat against my body. I feel a cold, sticky patch against the skin on my small mound of skin.

It makes me throb thinking about wearing her thong with her wet pussy juices in them. Why do I think and react this way to something so gross?

She points to the other side of the room. I rifle through her drawers until I see a garter belt made from the same black satin as the thong. I wince in anticipation of being hit again.

Her arm doesn't move, so I start to try them on. I pull the soft satin up past the thong, over my hips, and see the little ribbon straps with clips, hanging down. I look over for big sis's approval, she gives me a nod, and I see her very subtly bit her lip.

What was she thinking about now?

I've got the hang of this game and know what I need to find now, I tell myself, rummaging through the draws. I spy a large, pink appliance-looking thing with some buttons on the bottom of it. I'd never seen that before in her top drawer, probably because it was up quite high. She pushes the draw quickly shut and says, "That's for big girls, in that draw. Unless you want to be a big girl, I'd stay out of there."

I think about what it would be and come to a vague conclusion. I'm guessing she might have that because she gets lonely sometimes. She has a lot of flings with guys, but they never seem to last. Carly will get visits from guys a few times, and then we never see them again. She mainly hangs out with her alternative looking girlfriends. Maybe they were her girlfriends?

That's it, a pair of black stockings with lace around the top. I look through the next draw and find the matching strapless bra.

"Very good girl, you have caught on very quick. Let me help sissy with these, they can be difficult for a little girl to do," Carly says, holding the stockings open for me to step into.

She slides them up my legs and it tickles the inside of my thighs as she does so. I feel my tiny penis start adding to the sticky patch in my sister's thong.

Carly moves behind me and pulls her bra up over my sensitive, puffy nipples, and clips them together from the back.

I look in the mirror, and through the transparent lace cups, I can slightly make out the pink of my nipples. I'm not sure why, but It reminds me of my ex-girlfriend Jenny's boobs, and I feel a small rush of adrenaline, like I'm close to squirting in Carly's thong. I also don't mind the feeling of my sister behind me, being so dominant.

I look back at the mirror, shocked, as I take in the image of my lingerie-clad body.

*Click*. I spin around to see Carly taking a photo on her phone. I instinctively cross my legs to at least try and cover myself.

"There's not much to hide there little sissy. I'm still shocked at how much smaller you've gotten in the last couple months. I mean, it was always tiny. But now its...like a little nub, like a little.. clit...and its a bit cute." She says, with a slightly different demeaner, looking over my body.

"You're playing along well, so I didn't NEED to take that photo, but you're actually looking.... quite...er... feminine Sammy," Carly says, with what sounds like a lump in her throat.

This seems strange, her whole attitude has changed in the last minute or so. She seems to have gone all quiet.

"Come over to the bed, little sissy," Carly commands. "OK, you've listened well, but you will still be punished a little bit...."

Confusion is written all over my face. What had I done? I did everything she asked for!

"You grabbed a bra that's a bit big for your puffy nipples to fill out," Carly says, laying back on the bed, wearing only my oversized athletic shirt.

"Now, I'm going to let you choose your punishment this time. You can have the hairbrush 5 times on each of your pink nipples, or....." She pauses, directing her eyes down between her legs.

I glance down but am not quite sure what she means.

"Do I have to spell it out? Hairbrush... or get down here and show your appreciation to your sister for babysitting you all day. And I won't take it easy on you with the brush either," she says, slowly creeping the shirt up her legs, allowing me a glimpse of her smooth pussy.

I can see a couple of spots glistening in between her smooth folds. I think she must be really enjoying this. I remember how much her squeezing my puffy nipples hurt earlier, and decide they are so sensitive, that I simply could not handle the brush even once or twice.

My heart racing, I move onto the end of the bed, and very tentatively move my head down towards the middle of her legs.

Why did she want this? She was a hot piece of ass, and could have any guy she wanted. Why did she have her tiny-dicked little brother, dressed up like a slutty girl, directing me to somehow pleasure her smooth pussy.

I feel her fingers run through my hair, and then her firm hand on the back of my head. I can smell her almost intoxicating aroma.

"Tell me what you choose little sis," Carly says, running her other hand over her own perky boobs.

"I want to show my appreciation, and... please big sis for taking care of me," I say with an air of reluctance.

I feel her fingers firmly grip my hair, while reaching for the hairbrush with the other hand.

I realise the cue.

"I want to please you and your nice pussy. I want to lick big sis's pussy because it's making my tiny, useless penis leak into my satin thong," I finish saying, feeling her hand pushing the back of my head firmly into her dripping wet sex.

"Lick it up and down," she moans, as I taste her salty but sweet wetness. It feels so soft and smooth on my tongue.

"Ah good little girl," she whispers, starting to move her hips to the rhythm of my tongue. I feel the wet patch in the front of my sister's thong grow larger. It starts to mix with her leftover stickiness, as I lower my hips down and straddle one of her shins.

I have no idea what to do, so she describes exactly what she wants, and I do it. My face is covered in her juices. As wrong as this feels, I'm starting to get really turned on, and start to grind my tiny, wet bump against the front of her leg.

"You have a tiny, pathetic, little penis, sissy. Hump and squirt your useless seed on my leg. That's as close as you're going to get to fucking someone."

Carly thrusts her hips and slams my face into her pussy, while I whimper at the feeling of her sharp nails, digging into the back of my neck. I notice her panting getting heavier, and she lets out a huge moan.

"Gooood girl...mmhmm," she screams, trying to muffle the noise with her own hand.

With my sister's pussy reaching orgasm on my face, it is sensory overload for me. I squirt in the front of my sisters thong, while grinding and humping, back and forwards on her leg. My moans drowned out by the force of her hand, pressing my face into her dripping, wet pussy.

Her body goes limp on the bed, and I keep licking, very slowly and gently, until her hand moves off my head, signalling I've finished my duty.

"You did very good little sissy. You followed ALL of my instructions. I can't believe your little pee-pee squirted in my thong, just from that. I just love how submissive you are becoming."