Sissy Buttslut Lvl 1

You begin to squirm around in the crib as you see Arabelle slowly begin laying down the dildo attached diaper near your bare ass. As you began trying to kick away the silicone and cloth combo, Arabelle immediately grabs your ankles and locks them in the iron grip of just one of her big yet surprisingly soft hands.

She says "Here we go sweetie." and lifts your legs and butt in the sky as she pushes the diaper and toy under you. She lowers you slowly as you're moaning through your pacifier in protest. Once your butt is low enough, you thankfully miss the smallish pink dildo by mere millimeters and you feel the tip scrape across your winking hole, up into your balls.

You let out a sigh of relief as your ass is fully lowered onto the diaper, your ass now leaning down onto the dildo and the shaft of it clenched between your butt cheeks.

Arabelle says "Don't worry baby, you'll get lots of that little pink training cocky. Mama's just gotta make it all nice and slippery first."

She pulls out a large bottle of lube or some kind of oil and begins pouring it all over down your erect penis, then your balls and all over your asshole and the pink toy lodged next to it.

For a moment you think she's going to rub the oil around your cock, but her hand veers down to your asshole, where she rubs the lube all over the dildo, her fingers brushing against your ass and clenching and unclenching hole.

Arabelle says "Ooo baby, your pretty sissy pussy is winking for mommy. Is this your way of telling me your ready for your stretching in your diaper?"

You shake your head 'no' vehemently, but her fingers move from the dildo to gently rubbing your hole and you have to admit it feels pretty good. No woman has ever touched you there before and Arabelle makes it feel like teasing your ass is an art form.

Then her finger goes from teasing to full blown penetration and suddenly it feels more weird and uncomfortable than pleasurable. She says "Mama's gonna get you ready with her fingers first. I don't wanna see my baby girl cry from getting her virgin pussy stretched too quickly." She winks at you with her finger partially lodged up your ass.

Arabelle continues pushing her slippery index finger into your asshole as you moaned in response to the odd sensation.

Her finger then starts pushing lightly in and out, feeling your loosening ass as she patiently waited for you to stop tensing up. You knew she could probably start finger fucking you at any moment whether you were loose or not, but you couldn't stop clenching around her finger. The situation was just too much, and if you were being honest this woman looming over you and currently penetrating your mostly virgin ass kind of scared you. It didn't help her hands were much larger than a normal girl of normal height.

She sees you continue to tense up and leans in to nearly whisper "Just relax baby and suckle on your paci like it's your bottle". She taps on the ring of your pacifier and the thing glows a faint pink again as you then subconciously begin sucking it as your whole body relaxes, including your tightened asshole.

As you loosen up due to what was clearly some kind of magic, Arabelle begins freely caressing your insides, which suddenly went from uncomfortable to weirdly pleasurable. You let out an involuntary contented moan as she brings her finger all the way out and then adds a second finger.

She smiles at you from above and says "Look at that cute baby enjoying her first stretching. Does baby girl like it when mommy's fingers are inside of her tight pussy?"

She leans in and whispers in a sweet motherly tone "Or does my sissy baby boy like being a naughty buttslut for mommy?"

Just then her fingers rubbed up against something that felt REALLY good and you moaned in ecstacy at the new feeling.

She says "Oops, mommy must've found your little button. We don't want your clitty making creamies before your diaper's on and before mommy can give you your reward. We better stay clear of that for now."

She then pulls her two fingers nearly out and adds a third finger to your ass. You're rhythmically suckling on the glowing pacifier and it's likely the only thing keeping your ass loose for her as she really starts to finger bang you.

Your cock seems like its straining and involuntarily throbbing to the limit even despite the pacifier making your asshole relax. It didn't seem like the pacifier was making your cock and balls relax at all now that you thought about it, maybe the only part of your body that was still straining and almost painfully horny as Arabelle now edged you in a completely different way from before. You felt like even the slightest touch of your cock right now would make it explode across your belly, or you wish Arabelle would just touch that one spot inside of you one more time thinking that might also push you over the edge.

No luck though, and just as you begin feeling like you might cum anyways just from her three fingers, she slows down to a stop and then slowly pulls her fingers out of your hole with a soft *shlickk*.

Before you get the chance to adjust, she says "Okay here comes baby's first training stiffy" as she repositions the pink dildo to line up with your hole and slowly inserts it into your loosened ass.

You groan around your pacifier at the thicker feeling of the toy. She tries to soothe you "Shhh shhh.. take that nice stiffy in and don't forget to suckle on your paci." She taps your pacifier again and suddenly the toy goes in much deeper and smoothly until it finally hilts inside you.

You let out a long exhale out of your nose, your body twitching a little at what Arabelle had just done to you.

The dildo wasn't too bad once stationary, but did she really expect you to keep this in you all night??

She says "Good baby! That's a good baby girl, taking that nice stiffy in your sissy hole."

You then see the inevitable popup:

New Skill: Sissy Buttslut lvl 1

Description: This passive skill allows you to take bigger larger cocks and items up your butt much easier than before. As the skill grows, so will your tolerance for larger cocks in your ass. This skill also adds +15% bonus to total pleasure from anal sex. WARNING: Higher levels of this skill could lead to a sex addiction debuff.

As you lay there on top the pink diaper, ass almost nearly impaled on the pink dildo attached to it, Arabelle says "Now, is baby boy ready for a nice smoochie on his wittle weewee like mommy pwomised?"

Despite everything, you were absolutely ready for her to touch your cock, much less kiss it, which hopefully meant a blowjob. You knew either way, you were gonna blow your edged load the moment her lips touched your cock. Despite this woman's weird obsession with treating you like a baby, she was still expertly edging you like she was a world-class sex masseuse and you weren't ashamed at all about it at this point that you'd blow your load the moment she touched you.

She continues "You've been such a good boy and a slutty little good girl for mommy, and now it's time.." She pauses her words and leans down toward your neglected throbbing cock. "..for mama to give you.." She's only an inch away and your worried you were gonna blow before she even got there. You groan in sheer lust. She continues "..a nice kiss on.." You close your eyes and get ready to try to make the most of the stimulation. Suddenly she shoots her mouth towards your stomach and blows into your bellybutton making a trumpeting sound into your belly.

The lack of usage of your hands and being completely splayed out and your ass pegged on a dildo, meant you couldn't do anything to stop her sudden mouth tickling. You began flailing and kicking your legs and pushing on your wrist restraints to stop her. You were moaning in protest and nearly laughing around your pacifier as she kept doing it. Your ass was squirming on top of the dildo and any thoughts of cumming just flew out the window.

She slows down her breath and then stops completely, giving you a kiss on your belly before she pulls away. When she's back looming over you, she has a the same motherly smile on her face, except maybe with a hint of playfulness now like she was holding back a giggle.

You just close your eyes tight and groan loudly in frustration at her denial yet again. She was obviously doing this on purpose. You thought she was at least supposed to "take care of your needs" but she was clearly putting her own needs and desires first.

She notices your frustration and continues smiling as she says "Oh don't be like that sweetie, mommy will still give you that kiss on your tiny winkie."

She leans over and pulls up the front of the diaper in one motion, wrapping it tight over you with both her hands. As she holds the sides tight, she leans down and kisses the front of your diaper right where your erection would be.. Annnddddd you barely feel it. The thick padding that she was purposefully holding very tight and her gentle kiss on the fabric barely allowed you to feel her lips. The very slight feeling of her lips just made your cock throb again into the diaper and only worked to tease you further.

You deeply exhale again and groan. Arabelle leans back up and says "See honey, mama keeps her word" and boops you on the nose like she was teasing you and secretly loving it. You couldn't tell if she was purposefully doing it or genuinely thought she was being playful, but you were assuming the former at this point.

Arabelle fastens the straps of the diaper and you feel the dildo fully pull into you as the diaper becomes taut around your pelvis and bottom. She taps the diaper between your legs where the dildo is as if it was a job well done and says "Okay sweetie, let's get you in some adorable sissy clothes and get you ready for your nightly feeding."