Son for Hire Ch. 56-70

Evelyn slips her arm around mine and tells Kitty. "Before you two silly kids head out shopping I need a few minutes with Donald."

"You da boss Evie." Kit points at her with double finger-guns. "Catch ya later."

"I'll see you later."

"I'll meet you at the truck darling." She winks to me with a little smirk, knowing full well Evelyn and I were likely up to no good. She spins and leaves us alone.

"Thanks Kit." I say after her as we watch her curly hair bouncing and bobbing down the stairs.

"Evie." Evelyn chuckles. "I like her. I really like her."

"Yeah, she grows on you." I admit. "Like a rash."

"Donald!"

"Just joking. So what did you want to talk to me about?"

She looks at me in that way a mother does and brushes some hair away from my forehead, just fiddling with me for the sake of fiddling. She enjoyed touching me and I was only too happy to be touched. "You live here now my boy."

"Yes Ma'am." I smile.

"And you are heading out." She traces a finger down my cheek to lightly pinch my chin.

"Yeah."

"Do you remember what that means?"

"Uh...oh!" It takes a moment but the recollection strikes me shortly. "My cage."

"Mmm hmm." She nods. "You are my boy. Mine." She strokes her hands down over my hair and across my shoulders. "I want you safe and snug and locked up tight. Nobody touches your little guy but you and me right now. He's Mommy's special guy until I say otherwise."

I bow my head with a bashful grin. "Yes Ma'am. I am yours."

"And I look after what is mine. If you meet any girls you like out there I want you to come home and tell me all about them." She says as she caresses my cheek. "My boy deserves a good woman. A girl who can appreciate him for who he really is. Not some good time girl just after your body."

I cannot help but giggle. "Good time girl?" I thought it so silly, her old fashioned hokey way of talking combined with the ridiculous notion that I was out there having to fend off throngs of babes all the time, but it was silly in the special way only she could be. "There won't be any girls, don't worry."

She was dead serious though. Gazing into my eyes and gripping my shoulders she states. "We will find you a woman who deserves you Donald. One who will treat you right." I was about to assure her again that I had already found the woman of my dreams and that she was standing right in front of me but she continues on with a command. "Okay, quick now baby. Kit is waiting. I want you to go downstairs, take a very cold rinse, get into your cage, then hurry on back so I can see." She turns me by the shoulders toward the stairs and swats my bum. "Go."

"Yes Ma'am." I titter as I take off to obey my command. Oh how I loved having a Domme to obey.

Moving quick I do exactly as I was told. I zip down to my new home, dig out my cage, find a towel, and then head into the washroom to be blasted by very frigid jets of water. "Whoooo!" I hoot as the shock of cold washes over me from my neck down. The force of icy streams was at least three times greater than the feeble water pressure back at the old place and in just a few intense minutes I am already shivering. Good boy that I am though I bear it for long as I can. The cold water invigorates my whole system while also washing away the sweat of the move. It also causes...shrinkage, which I am soon thankful for. After my time with Evelyn in the bedroom my libido had been simmering at a constant rate of horny and I'd been sporting a chub ever since, after that shower though my genitals were in full retreat. After toweling myself off I have not trouble at all feeding my shriveled manhood into its cage. Hell, unlike normal, there was room to spare! Hurried I dress and dash back up to find her and show how good I was locked up.

I find Evelyn not in the kitchen or in the main floor at all, but still up in her bedroom. I poke my head into the partially closed door. "Mum?"

"In here." I hear from the attached washroom. "Come in."

I walk through, still adjusting my stride and how my cage was seated, and enter the washroom. I find her standing near the sink. The way her eyes lit up at just the sight of me...well, it gave me life. You could not fake a look like that. If every man and woman saw genuine love like that in the eyes of their beloved the world would be a much nicer place. All of the pain and abuse I'd suffered at the hands of my mother, that I only recently realized I carried around with me like an anchor in everything I did, was momentarily forgotten in that feeling of strength and confidence I got from my Mommy.

"Hello handsome." She says.

"Hi." I say meekly. She loves it.

"Let Mommy see." I nod. Undoing my pants I let them fall then pull the front of my tight underwear down to reveal my bound penis. It looked kinda funny pressed against the clear plastic. To Evelyn it is the most wonderful sight. "OHHHH!" She croons. "He is adorable!"

I laugh. "That cold water had him trying to hide."

"Get over here!" She waves me in. Stepping out of my pants I come in close. She cups my package and admires it with burbling glee. Her caging me was an act of dominance, no doubt, but not one of humiliation like some of the things I'd read online since I'd been given my cage. She caged me because I was hers, her property as far as I was concerned, and not because she wished to belittle me or emasculate me. I could swing free all I wanted while under her roof but out in the world she wanted me safely under lock and key. "Look at him." She says. "Just look at him! All snug as a bug."

Thrusting my hips forward I show it off proudly. "Nobody's touching him without a key."

"You're comfy?" She asks. "You practiced peeing with it."

I roll my eyes. "Yes Mom."

"Good." She kisses two fingertips then touches my cage. She then tucks my undies up over it and pats my chest. "You are a good boy." Stepping to the side she reveals a mysterious small black box on the counter behind her.

I look at her with an expression of exasperation. "Another present, seriously?"

She laughs. "I can't help myself."

"You really are going to end up spoiling me."

"Rotten." She says shamelessly. "Open it."

My gratitude already full to bursting all I can do it accept the gift with humble appreciation. I step up beside her and open the fancy hinged box to reveal a vibrant turquoise...thing...cradled within a satiny pink interior. It was one solid piece of silicone with a bulbous end that tapered down into a narrow shaft that then ended in a crescent shaped base. My first thought was that it was an enormous binky designed for adults. It seemed awfully big though for that purpose. I hadn't intended on going that far in our roleplay...but if this is what Evelyn desired I'd at least give it a try. Just before I say something embarrassing though my mind shifts and the object's true nature is revealed to me.

"A butt plug?" My dick swells, only to be instantly constrained by my cage.

"It will help us get you ready for me." Her hand glides across my back as she sidles in next to me to look down at it with me. "Blue."

"My favorite color. You remembered." I smile. "You want me to wear this? Now?"

"I never said that." She says softly. "Do you wish to wear it out?"

"Yes please."

"Ask nice."

Touching the bulbous head I feel the soft texture of the silicone. "Please. Please may I wear my plug Ma'am?"

"Mmmm." She hums warmly, the hand at my back gliding down to be filled with a cheek of my ass. With a gentle squeeze she whispers. "Of course my prince."

***

Chapter 64

With my permission given Evelyn takes control of me. Wrapping her arms around me she lightly nuzzles the short hairs at the back of my neck and sends delightful tingles down my spine. Pressed into me like she was I could feel the fat shape of her semi-erect cock through her dress.

"Ohhh." I sigh as she grabs my pecs to squeeze them while giving me little kisses around my neck. The cage around my dick goes from snug to super tight as my body responds to Mommy's love.

Reaching past me she slides the box across the washroom counter to clear it in front of us. With her other hand she lightly pushes me down over it. Bending at the waist I lower myself and rest my elbows on the counter. As I look up into the mirror to look at her reflection I watch as she grips my hips and presses herself firmly into my butt, hard enough to let me feel her her girthy lady schong even better.

"Oooo." I coo and very subtly grind my bum in small slow circles against her. Through the mirror I look at her, pleadingly and bravely, showing her that I wanted her to take me here and now.

"Mmm." She smiles as her soft hands glide up my sides to slide in under my shirt. Her fingers stroke back down my stomach. One hand pauses at my belly button to tease it with her middle digit as the other continues down to slip beneath my undies and play with my short soft pubes.

"Oh!" My manhood strains against the plastic walls around it but try as it might it simply could not escape. Through clenched teeth I let out a hissing breath. I was already so damned worked up from earlier, my lust was burning as hot as I could ever remember it, but not only could I now not find relief in an orgasm...now I couldn't even get hard! The denial only made my passions build and build like a boiler without a steam valve to release the excess pressure. With my cock blocked off all of my burning desires readjust to just my hungry ass. Grinding harder against her I mewl pleadingly. "Fuck meeee."

"Shhhh." She feels around my caged penis and tight balls, tickling the latter and watching me squirm.

"Mmmmm! Mum!"

She chuckles and brings her hands back to my hips. With a very soft swat to my butt she says. "Patience is a virtue."

"Whooo. Yes Ma'am."

Backing off of me Evelyn takes the waistband of my underwear, one of the cute pair that she'd bought me, and pulls the back of it down over my ass. With a pat at the small of my back she says. "Stay."

"Yes Ma'am." Bent over with my ass exposed I grip my new toy tightly in my hand as I watch my milf domme go about her business.

She gathers a wash cloth, a towel, soap, and an anal lube that she had on hand knowing full well that I was going to ask to try out the plug. She walks up beside me and turns on the sink. Testing the water with her wrist she gets it just the right temperature and wets the cloth. "So what are two off to buy?" She asks as she puts just a tiny dab of soap in the cloth and massages it into suds.

Forcing myself to focus I say. "Sofa. Kit already has her eye on one."

"Nice." Evelyn rings the cloth out leaving it wet but not sopping.

"We were going to get other stuff." I say as she walks back around behind me. "But with that stuff you just gave us...oh!" I am interrupted by the feel of the warm wet cloth sliding up and down the crack of my ass. Even though I had just rinsed off she wanted extra clean down below. With a warm Mommy smile she looks down at my tush as she very thoroughly and very gently cleans me. I swallow and continue. "Um...with that stuff...you gave us...ooo...we can now put more of budget...whooo!...into a television."

"A TV? That'll be nice."

"We've never had good one before."

"Mmm." She nods with a final wipe. Pausing a moment, as if weighing something up, she continues staring at my ass...before lowering herself to her knees behind me. "Just a taste."

"Ma'am?" The next I knew my glutes are being spread apart! A moment later comes the touch of a tongue right smack dab in the center of my butt hole. "Oh God!"

Her face cheeks pressing in tight along the inside of my ass cheeks her strong, wet tongue laps and probes at my sensitive back door. Lowering my head I close my eyes and focus entirely on the incredible sensation of having my ass eaten. Her tongue circles my anus before knocking at my entrance with a series of rapid taps. With all of my libidinous energies already focused there each teasing tongue tap sends sexual tingles up through my whole body.

"Mmm." She hums. "You taste so good baby." She slurps hungrily at my hole. "Mmmm! So good."

"Ohhhh!" I bend all the way down so that my chest and cheek touched rested on the counter and tilting my hips slightly up I give her even more ready access to my hole.

Just like with her blowjob she goes down on me with such care and tenderness that it brought a tear to my eye. She treated me so nice. Like something precious and fragile and irreplaceable. While slow and gentle she is not hesitant. With lips and tongue she eats me out with an enthusiasm that could not be faked. Gradually at the firm patient proding of her incredible tongue my sphincter begins to loosen and open. The feeling as her tongue plunges inside of me...exquisite! Suddenly my caged pecker didn't seem an issue, all I needed right now was THIS!

"Ohhhh God yessss!"

"Gooooood boyyyy." Her wet lips give my anus a sucking kiss then she pulls away. The next moment comes slick lube that, unless I was mistaken, had been warmed in her hand as she ate me out as it was already nice and warm as she rubs it into me. "You have such a beautiful ass baby."

"Thank you."

"Like a pretty little starfish." She taps it finger a few times to make it spasm. "Look at it dance. He he he. So pretty."

"Mmmm." I moan as she slides the finger into me. "Nnnnnngh!" Then right out again. "Ohhhh." I whine.

"Shhhhh." Standing up she says in a low voice. "Give me your plug."

I pass it back to her.

"Get up on the counter."

I stand up and turn around to face her then hop back up onto the cool marble counter. She didn't need to order the next bit as I automatically spread and raise my legs for her. She gives me a proud nod of approval. "Look at you my boy." She lubes the rounded turquoise tip of the butt plug and coats it right down the crescent base with her finger before steping into me. She pulls me legs loosely around her. Feeding arm down between us she feels around a moment to center the toy at my lubed and ready asshole. "If it hurts or something doesn't feel right..."

"I'll tell you."

"Good boy." She says. "Hold onto me baby. Hold onto Mommy."

Reaching my arms out I take her around the shoulders and pull myself closer. The base of the plug she plants against herself, using her body for extra power and control. The effect of which made it seem like she was holding her own cock and that it was this that she pushes up against me. Her other hand comes up to my head. She combs her fingers through my hair then hooks her hand around the back of my head. Her eyes stare deeply into mine as she very gradually leans her weight in, moving in just the way she would if it was actually her penetrating me.

"Nnnnngh." I groan as the toy begins to make progress. It was blunter and thicker than my dildo but I was well lubed and warmed up for it so it isn't too hard to relax and open up to it.

Gazing into my soul Evelyn whispers. "That's it. You can do it my love. You can do anything!"

"Ohhhhhh." I sing as the thickest part of the bulb stretches my ass like never before, another humbling reminder that despite my will to do it and the fact I'd come a long way my body was simply not ready for Evelyn's monster yet. "Hahhhhh!"

"Gooood, gooood, you are doing so well." She very slowly thrusts into me

"Hmmmmm!" I hold to her, genuinely borrowing strength and courage from my Mommy's embrace as the stretching begins to burn just a little bit. Evelyn holds me tight, never letting go. And then all of a sudden...pop! The plug slips past the thickness and my hole tightens down around the much more slender shaft, pulling the rest of it inside of me. "HAAHHH!" I gasp as the bulk of the bulbous end fills my rectum.

Evelyn grins. "How is it?"

"Hahhh...good...real good." I gasp. "Oh my!"

She kisses me. "You did so good." Twisting the toy just a little bit and sending fresh sparks of joy through my ass as I feel silicone plug grind over my prostate she centers it so that the crescent base was snugly fit perfectly along the curve between my cheeks. She pats it twice. "There you are. Caged and plugged and ready to go out."

My cock twitches impotently in it's cage and my anus bears down hard on my ass filling plug and a lust worthy of Eros himself rages through every fiber of my being. I was supposed function like this!? "Ohhhh God!"

***

Chapter 65

Evelyn pulls my underwear up over my butt and gives me an adoring pat. She steps back. "Is it comfortable?"

Slowly straightening up I feel the ass filling plug shift slightly with my movements. "Oh! Um, yeah."

"Doesn't hurt or pinch or anything?"

"Uh, noooo. It's...interesting." At a loss of words of quite how to describe 'interesting' was all I could think of. There was no discomfort at all, if anything it was quite pleasurable. I felt this wonderful fullness as the bulbous head filled the space just inside of my booty hole. If it were any larger I think it would have been a challenge but she had wisely chosen a small one to start me off with. The crescent base sandwiched between my cheeks was actually the weirdest bit as it kinda felt like I had a hard lump of shit sitting in my drawers, but I would quickly get used to that. I swivel my hips. "It's sort of nice actually."

"Good." She smiles. "Walk around. See how it feels."

I walk a slow circle around Evelyn. "Ohh, it's sorta shifting in there. Pressing against...things. Whoo!" I laugh. The choice of silicone was a good one as it allowed it to bend with me. I was thankful now she hadn't given me something hard and inflexible like metal or glass. It wasn't just the plug making things feel so different. It combined with my cage left me feeling well and truly contained yet so virile and potent, like a mighty genie trapped in his bottle awaiting his master's touch to release him or some powerful savage beast that must be restrained for the safety of those not his tamer. The more I walk the more I get used to it and before long I am walking relatively normally. The real hard part was containing my sighs of joy as the toy rubbed my P spot. "How do I look?"

"Sexy, cute, lovable."

I chuckle. "I mean do I look like I'm walking normal."

"Yes." She says and steps up to slide a hand across my back. She kisses my shoulder. "If the plug feels bad, in any way, I want you to take it out. Okay?"

"Sure." I quip. "I'll just bend over in the furniture store and pop it out."

"Find a washroom silly." She laughs and hugs me then pats my tush. "Since this is the first time you are wearing one I don't want you out for too long. No more than a couple of hours, okay? And no heavy lifting or roughhousing or anything too strenuous."

I cannot help but smile. She sounded so much like a worried mother. "Yes Ma'am."

She then pats my caged peen. "And I am sure my little guy would like to stretch out."

"Yes Ma'am."

"The faster you go, the faster you're free."

"Yes Ma'am."

"Good boy. Okay, get dressed now my pet. Kitty is waiting."

"Yes Ma'am." I get my pants back on and check myself out in the mirror as Evelyn watches me. In the reflection all looked normal, what was happening within my undies was a kinky little secret only she and I knew. I loved it!

Evelyn hugs me from behind, a long joyful possessive embrace. "Come back home to me my prince."

"As quick as I can." I bring my arms over hers and hug them into me.

After a few more tender moments she lets me go. I kiss her cheek and head out the door. Our suite was already locked up and I find my sister out at the end of the driveway chatting with one of the neighbors. "Darling!" She waves to me. Turning to the tall brunet woman Kit says. "Gotta go. It was nice to meet you."

"Indeed." The woman drolls. She gives a look and a slow nod then heads off down the sidewalk.