The Ultimate Sissy day for me

[ppbenn]

The Ultimate Sissy Day For Me

 

"Good morning my beautiful sissy baby," Mommy smiles at me as she says this as I rub the sleep from my eyes. I yawn and stretch in the bed that we are lying in together.

 

"Good morning Mommy." Just like I always do; normally it's through text, but when I can tell her that in person it means more to me.

 

"Now baby I know we had fun last night while we were out with our friends, but Mommy has big plans for you today, and we can't be lounging around all morning if we are going to get everything done. Don't you agree?"

 

"Yes Mommy. I'll get up." I tell her as I start to move and take the covers off of me. 

 

"Not so fast baby. First rule of today is that you don't do anything unless I tell you to. Is that clear?"

 

"Yes Mommy." I can already feel butterflies as she tells me that she is in absolute control today.

 

"That's my good sissy baby. Now what kind of Mommy would I be if I didn't give my baby some breakfast? Not a good Mommy that's for sure, and I am a good Mommy aren't I diaper butt?"

 

"You're not a good Mommy. You're the best Mommy and I love you."

 

"Awww you're sweet crinkle slut, but first you need to eat." Mommy tells me  and she pushes me down flat on the bed and sits up. 

 

Within seconds I am looking up at her breasts as she sits on my chest. I can feel the heat from her pussy on my bare skin. My cock is beginning to stiffen inside the confines of my diaper, but Mommy obviously has other plans. 

 

"Do you know what's for breakfast for you diaper slut?"

 

"Pie?" I ask trying to be coy, but Mommy isn't having none of that today.

 

"No baby you're getting Mommy's pussy and you're not going to stop eating that until Mommy is satisfied."

 

Having said that, she moves up and places her hands on the wall behind me and slides her body up mine until her pussy is just above my mouth.

 

"Go on crinkle butt eat your breakfast for Mommy."

 

I stuck my tongue out and began to lick her. I always enjoy pleasing Mommy like this, and today is no exception.  

 

“That’s right baby, make Mommy cum. You are just for Mommy’ pleasure today.”

 

Within minutes Mommy came on my face, after she slid off my face and cuddled up to my naked body I could feel her breath calming; as she came down from her orgasm.

 

“Ok slut. Now it’s time to get something to eat for real and then we can go have some fun.”

 

Breakfast was a simple affair of eggs, bacon, toast and coffee and as soon as it was finished, Mommy had me wash the dishes and put them away. When the dishes were cleaned to her satisfaction; Mommy led me back downstairs and told me to lie back down on the bed while she got my outfit ready for the day.

 

I thought I would at least get to see what I would be wearing before Mommy dressed me in it, but Mommy had other plans as she grabbed my blindfold and put it over my eyes.

 

“Mommy is so excited for today. However I need to make sure that you look pretty too. Mommy is going to plug your ass cunt today and cage that little clitty of yours today. Don’t worry though Mommy will make sure that your diapers are extra thick because I know that once a plug is in your ass and your little clitty is all caged up; you’ll be a leaky mess so Mommy will keep you all padded up and make sure that she has extra diapers on hand when we go out so that I can change you. Does that sound good sissy slut?”

 

“Yes Mommy it does sound good.”

 

“I’m glad it does because you didn’t have a choice anyways. Now for what to wear”

 

After a few minutes of looking through clothes Mommy decided on an outfit and dressed me up. It was nothing overly fancy just a pair of sweatpants ( which I was thankful for, due to my wonderfully thick diapers,) one of my printed onesies and a large tshirt.

 

“Ok sweetie you’re all ready. Now I want you to take your diaper bag out to my car while Mommy gets dressed. Oh and get the red bag beside your diaper bag out there too, but don’t look inside it Mommy packed some extra things in there for you to wear later.”

 

I grabbed the two bags and took them to the car. When I got back inside Mommy told me that I could go wait for her outside and she would be there after she put on some make up.

 

A short while later as I stood outside on my porch smoking one of my cigarillos and drinking a monster: Mommy came out looking as beautiful as ever and with a sharp smack on my thick bottom told me it was time to go.

 

Since Mommy does not like driving she had me drive and told me where to go. The first stop was a grocery store where we went in and got some alcohol. I was conscious of my diaper as I crinkled and waddled down the aisles but just to be sure Mommy smacked my butt a few times to further remind me of my padded state. Before we left the store though Mommy led me over to the cosmetics aisle where she told me to pick a lipstick but also to make sure that it was good one that wouldn’t smear when she had her cock in my mouth later. 

 

I decided on a bright red one that supposedly was long lasting and wouldn’t stain later. When I handed it to Mommy I was rewarded by her telling me that it was a good choice and I was going to be such a pretty little sissy cocksucker for her later.

 

Our final stop after leaving the store was a small hotel room that Mommy had already reserved a room at. She went into the lobby and checked in and then came back out a few minutes later with the room key. I drove around to the back of the hotel and got the bags out while Mommy unlocked the door. 

 

“Are you still dry sweetie or does Mommy need to change you?”

 

“I’m still mostly dry at the moment Mommy.”

 

“Mostly dry? Hmmm Mommy had better check you because I know how much of a little pee pee pants you are and I don’t want you to leak all over the bed while Mommy is having her fun with you. Go ahead and strip down to just your onesie and diaper and Mommy will be with you in just a minute. I have to step out and make a quick phone call.”

 

“Yes Mommy.” I did as she told me while she stepped out of the room. 

 

I was a little self conscious when she came back in and there I was in nothing but an obviously thick diaper and onesie laying on the bed in full view of the parking lot, but luckily no one was nearby that could see in the room.

 

“Ok sissy slut; let Mommy see just how “mostly dry you are.”

 

Mommy sat on the bed in front of me and undid the snaps of my onesie and told me she was proud of me for staying mostly dry up to this point, but she added that she was sure that would change soon. 

 

“Well it’s still a little early but since Mommy has plans for you here in a bit and I want to make sure you stay hydrated go ahead and get something to drink, but for every two of your beers that you drink I want you to drink one bottle of water, and to make it easier for you to do that Mommy put a bottle in your diaper bag and I will give it to you myself.”

 

I grabbed a beer and fixed Mommy a coke and rum and then cuddled up beside her on the bed so we could watch a little Saturday college football while we relaxed and enjoyed each other's company.

 

After my second beer Mommy had me fill up the baby bottle she had put in my diaper bag with a bottle of water and let me lay my head down in her lap while she fed me the bottle. I have to admit that lying down in her lap and having her rub my freshly shaved head while she told me that I was her good little diaper boy, had a very relaxing effect on me. After the bottle was finished I told Mommy that I had to pee.

 

“Go ahead and go potty in your diapers then baby, Mommy made sure they were extra thick because you are such a heavy wetter.”

 

I got up and went to the other side of the bed closer to Mommy and while I wet my diaper like the little baby I was, Mommy cupped my diaper and I shivered in near orgasmic bliss. I can’t explain why though. Maybe it was because I was in such a vulnerable state at the moment and feeling Mommy’s hand cupping my diapered crotch reassuringly while I voided my bladder had me feeling loved and cared for, but also a little humiliated; because I felt like I had no choice in this matter while she watched me. Whatever the reason, I know that I liked it and when I had finished wetting my diaper, I nearly fell down on the bed beside Mommy.

 

“You’re such a good diaper slut using your diaper for Mommy. Come lay down beside me and show me how else you can be a good slut for me.”

 

“Yes Mommy.” 

 

I laid down between her legs and moved her shorts and panties to the side so that I could please her with my mouth again for the second time that day.

 

“That’s Mommy’s good little slut, make Mommy cum. Come on baby, you can do it.”

 

As I licked her she rubbed my head and told me how I was doing such a good job making her happy.

 

It wasn’t long after I started licking her that Mommy had an orgasm and then another while I sucked on her clit. Finally she had enough and told me to come lay beside her. We cuddled like that for a while and then Mommy told me I could have a couple more beers while she went and took a shower. 

 

“You did such a good job baby, you make Mommy happy and I love you very much. When I get out of the shower Mommy is going to change your diaper and get you all prettied up for the rest of the evening. No matter what, remember that Mommy loves you and you are mine and I will never do anything to hurt you, and I am going to do my best to make your sissy dreams come true.” 

 

She gave a kiss on the lips then went and got in the shower. While I laid on the bed for a few more minutes just reveling in how much I felt loved and cared for at the moment. Eventually I heard the shower running and got up to get myself two more beers, but also taking the time to refill the baby bottle with water for when I finished them.

 

Thanks to the tall boys of beer and the bottle of water I wet myself again while Mommy was in the shower and the thick diaper between my legs became even poofier as I peed. 

 

When Mommy got out of the shower and saw my soaked state she laughed and commented about how big of a baby I was. Before she changed me though she got dressed in some of her pretty lingerie and told me it was almost time for some fun.

 

“Obviously Mommy needs to change you first; so let’s go ahead and do that. You know what on second thought I don’t want you smelling like a pissy diaper baby so go ahead and strip and Mommy will draw you a bath so that you are all nice and clean for later.”

 

I had no idea what was planned for later, but the thought of Mommy giving me a bath had me feeling excited and I quickly took off my onesie and diaper. The latter fell to the floor with a wet plop. Mommy did have to remind me to remove my butt plug though, but I wasn’t allowed to remove cock cage other than to take off the small metal padlock so that it wouldn’t get wet while she bathed me.

 

By the time I was naked and ready Mommy had already drawn the bath water and had it filled with a lavender scented bubble bath. I stepped into the warm water and felt even more content than I did earlier while she washed me with baby wash.

 

“You’re being such a good baby today and Mommy is proud of you.”

 

Her words washed me over and left me with a feeling of warmth and love. 

 

Before she finished washing me and having me get out of the tub; she had me stand up and turn around so that she could wash my backside. I felt the washcloth between my cheeks as Mommy made sure I was all clean and then her hands on my shoulders and her voice in my ear.

 

“You have been a very good boy so far today, but we both know you aren’t a baby boy are you sissy?”

 

“No Mommy, at least not today.”

 

“That’s right sissy and not any other day either unless I want you to be. Now you’re going to get out of this shower and Mommy is going to dry you off and then I will lay you on the bed and tell you all that she has planned for this evening and for her diapered sissy slut. Understand?”

 

“Yes Mommy.”

“Good girl.” She let go of my shoulders and then gave me a swift smack on my bare ass.

 

I let out a little yelp; which made me chuckle. “That was nothing slut. Mommy has much bigger plans for that ass of yours tonight.”

 

I stepped out of the tub and unplugged the drain so that the water could drain and was then dried off by Mommy and led back into the bedroom area and told to sit on the bed. 

 

“Ok my little sissy slut close your eyes.” Mommy ordered me. 

 

I did as she told me and then she had me lift my arms. She slipped something over my head and then threaded my arms through presumably the sleeve holes. Whatever she was putting on me felt soft, and silky, and I could feel my clitty try to harden despite the cage Mommy had put on me.

 

“Ok slut you can open your eyes now.”

 

I opened my eyes and saw a beautiful satin pink dress on my body. The shade of the pink matched my cock cage perfectly. 

 

“Do you like it sissy?”

 

“Yes Mommy I love it. It feels so soft and I don’t know but I feel pretty now.” I felt my cheeks flush as I made the minor confession, but when I looked at Mommy she was just smiling.

 

“That’s good baby, Mommy loves making you happy and you are correct, you do look pretty but this is all you’re going to be wearing tonight. Now go ahead and lay down on your back so that Mommy can finish getting you ready.”

 

“Yes Mommy.”

 

“Pull your legs back for me slut, Mommy is going to put a toy inside your bottom.”

 

I pulled my legs to my chest and watched as Mommy poured some lube on her fingers. “Look at this little sissy hole; it’s just begging to have something in it. Do you want Mommy to fill your ass pussy up slut?’

 

“Yes please Mommy.”

 

“Good girl, Mommy loves making her slut happy do you know why?’

 

“Because I make Mommy happy?”

 

“That’s right baby you do make Mommy happy, and I can’t wait for everything later either.”

 

She probed my bottom with her fingers for a few seconds before sliding the toy inside me. I moaned at the feeling of being filled and could feel myself slipping into a sub space as Mommy pushed the toy against my prostate. 

 

“You’re such a greedy little slut that toy slid right in. Does it feel good”

 

Before I had a chance to respond to her question an intense vibration overtook me and I shivered with intense pleasure.

 

“Oh, does the baby like that?”

 

“Yes Mommy, that felt wonderful.”

 

“Well Mommy has been wanting to try this toy out for a while. It’s a remote controlled prostate massager and that was only at the second setting it goes up to ten.”

 

“Holy shit Mommy!”

 

“Holy shit is right baby. Mommy is going to be playing with this toy all night and I’m going to enjoy watching my diapered slut writhe in pleasure.”

 

“Yes Mommy thank you.”

 

“Don’t thank me yet baby Mommy still has lots of plans for you tonight. Would you like me to tell you?”

 

“Yes please Mommy.”

 

“Ok I will, but first let me go ahead and make sure you’re all ready. I can see how excited you’re getting even with your clitty all caged up; so I better make sure that you’re diapered up nice and thick. I don’t want any leaks or mysterious stains on the bed for housekeeping to find.”

 

“Yes Mommy.”

 

“First things first let’s get you diapered. Hmmm...let’s see earlier you had two stuffers in your diaper but you’ll be laying down most of the night so I think we should add a couple extra to that to make sure you don’t leak. Lift your bottom for me.”

 

I lifted my bottom and Mommy slid a thick pink diaper underneath me with the added stuffers.

 

“Oh my this is almost too thick to tape up properly. Well no worries it will just be a little more snug, that way it can press up against your sissy plug.” Mommy told me as she tapped the toy that was inside my bottom; causing me to shiver a little bit.

 

“Awww my diaper slut likes their toy doesn’t she?”

 

“Yes Mommy it feels good”

 

“That’s good slut, now Mommy is going to remove your cage, but that doesn’t mean your cocklet is going to get anywhere near a warm, wet place to cum in. Well I guess that’s not entirely true. Here soon your diapers will be warm and wet and babies do wear diapers to contain their messes even if it’s just a sticky mess like you’re going to make.”

 

My cage was removed and then the diaper was pulled up nice and tight between my legs. Mommy was right that the diaper was a little snug and it pressed tightly against the plug in my ass. After the diaper was taped snugly around my waist Mommy grabbed a pair of pink stockings that she had hidden earlier so I didn’t  see them. She slid them up my legs. The soft feeling of the stockings and then Mommy running her nails up and down my leg once they were in place had me feeling breathless. 

 

“You’re looking so pretty for Mommy, my little sissy slut. We’re almost done and then Mommy will tell you all she has planned for you. Ok”

 

“Yes Mommy,” I replied. I have to admit being kept on edge all day about all the plans she had for me left me feeling wanting, but I did want it and I wanted this beautiful woman whom I loved and called Mommy to give it to me.

 

Mommy got off the bed and came to stand beside me. “Just a couple more touches and my diapered sissy slut will be all ready for Mommy. Next we have your pacifier here, and Mommy even bought a pink pacifier clip for your pink pacifier. You look pretty in pink, baby!”

 

“Thank you Mommy.”

 

“You’re welcome baby! Now hold still while Mommy puts this lipstick on you. After all you want to be a very pretty sissy cock sucker don’t you?”

 

“Yes Mommy. I want to be a pretty sissy cock sucker for you.”

 

“Good girl!”

 

She put the lipstick on me and then gave a tissue to blot my lips a little.

 

“There we go, baby doll. Now just a couple more steps; hands over your head, and spread your legs.”

 

I did as I was told and watched as Mommy secured my hands and feet to the bed frame with velcro cuffs.

 

“Ok baby two more things and one is something new, but Mommy has been wanting to try it for a while.” 

 

She grabbed a blindfold and had me lift my head so she put it in place over my eyes, plunging my vision into darkness. Then I felt her securing something to my thighs. When she finished securing it, I sensed her stepping back and then heard her say. “You look so adorable, baby. Almost too adorable for me not to want to fuck right now, but there are other plans, but first let me take a few pictures of my pretty in pink slut.”

 

“There we go baby. Mommy is all done teasing you and I shared all the pics on fetlife; so that everyone will know you’re my pretty pink, diapered, sissy slut!”

 

“Here’s what’s going to happen. Here in a few minutes a couple of Mommy’s friends are going to come in here and they’re all going to see how fucking adorable you are. They’re probably going to want to tease you. They’re going to want to touch your stocking clad legs, and they are most definitely going to want to feel that ridiculously thick diaper between your legs. They are going to want to play with the remote control for the toy in your little sissy hole. They are going to want to play with the vibrator that I have strapped to your leg; which is pressed right against the padded cliitty of yours and Mommy is going to let them do this. Hell Mommy is going to join in. Then we are going to have some drinks and maybe order some food for delivery.  Mommy is going to feed you and give you your bottle to drink; which by the way you did a good job filling it up for Mommy earlier. After all that is done then Mommy is going to let them wear my strap on and you are going to use the pretty red cocksucking lips of yours to suck their cocks, and show them how you do an incredible job sucking cock. Does all that sound good baby?”

 

“Yes Mommy, but I’m a little nervous and scared.”

 

“Don’t be baby Mommy will be right here to protect you and not let things get out of hand and you can say ‘red’ at any time and Mommy will stop whatever is going on to take care of you. Ok?’

 

“Yes Mommy, thank you.”

 

“You’re welcome baby. Now I can’t say for certain but maybe one of Mommy’s friends will want to see what else you can do and Mommy will let them see how well you take a cock in your ass, but I don’t know about that yet. Nonetheless it’s all going to end tonight when you show Mommy and her friends just how much you love having your sissy hole played with; because Mommy is going to turn the toy in your ass pussy up to ten and then I am going to use that wand you love so much right on your clitty and have you cum as much as we want you to. Ok slut?”

 

“Yes Mommy.”

 

“Oh and this is only for tonight, next time Mommy will see about getting a real cock for you to suck and take in your diapered sissy ass. I hope you’re ready because I just heard a car door.”

 

I waited and laid there patiently for a few seconds, wondering what in the world I had gotten myself into, but then I heard Mommy say, “come on ladies; he’s all ours tonight!”

 

[diaprbayb]

[wetste]

Cool story so far