Tucked In by "Mommy"

Continued from: A Special Bedtime for Russell

A Sarah Jane story 

"Now, be a good girl and bring the plug and lubricant to Mommy," I sang out from my seated position on the ottoman. No doubt Russell, in this very moment would be holding and handling the realistic plug in horror, feeling its veiny contours, fully aware of what was about to happen next. 

Russell gathered the towel with the two items balancing on it, his cheeks flushing crimson like his bare bum, and presented them to me. I accepted the towel with a nod of approval, setting the items aside momentarily as I shed my robe, exposing my stocking tops and garters, patting my strict lap invitingly. 

"Pull down your panties and lay across Mommy's lap once more, my sweet girl," I cooed, gently caressing his sore bottom to guide him over my knees. I took a moment to admire the sight before me - his bare bottom, still rosy from my slipper, upturned and vulnerable. 

Reaching for the lubricant, I squeezed a generous amount onto my gloved fingertips, spreading it liberally over his tight little hole. Russell gasped as I breached him, my digit sliding easily into his naughty bottom. I spent a little time on his prostate, finger beckoning it from inside him, milking-out a few spider-strands of pre-cum that I knew would be glistening from his chastity cage and dampening his panties when he slips them back on. 

I worked him open a little more, adding more lubricant as needed, until I was satisfied with his readiness. Only then, did I reach for the plug, coating it thoroughly in the slick lube. "Relax, little one," I whispered, pressing the tip of the plug against his pucker. Russell whimpered as I pushed forward, his body resisting the intrusion. But I was patient, working the plug in millimeter by millimeter until it was fully seated up his bum. I could feel his muscles clenching around the base, his body adjusting to the unfamiliar fullness. 

Gently, I pulled his panties back up, pulling them high on his hips so the thong portion would help hold in the plug. "There now," I cooed, helping him to stand and turning him to face me. "How does it feel to be nice and full, just like a girl? Does it make you feel owned and claimed by Mommy?" Russell nodded, too embarrassed to speak.

I guided him to the bed and had him lay down on his side. Laying down on his tummy would be no good for the cock cage, if he was laying on his back he would become acutely aware that he was recently spanked and now anally plugged. On his side, in a vulnerable fetal position was perfect to be "tucked in" by Mommy.

From the bedside table, I retrieved four baby pink bondage cuffs, their soft leather brought a beautiful scent as I held one of them up to my nose. With gentle but deliberate haste, I secured the cuffs around Russell's wrists and ankles, adding a small brass padlock to each buckle. As I worked away, I couldn't help but admire the picture he presented - a vision of feminized helplessness, his frilly attire a mockery of his masculinity. 

With one final length of narrow chain, I connected his ankle cuffs to his wrist cuffs, with more than enough room to comfortably move about on the bed. 

Once he was fully restrained to my liking, unable to reach back and remove the plug or his attire, I leaned over and pressed a gentle kiss to his forehead. "There you go, my sweet little girl," I sang out to him. "All tucked in and ready for bed. Mommy will be up to join you in awhile," I promised, my voice laced with maternal care. "In the meantime, you just rest there and think about how lucky you are to have a Mommy Domme to keep you safe and controlled."

With a final whimper from him, I glided out of the room and went downstairs to get some fruit, still feeling like an absolute Goddess. 

I couldn't help but think of Mistress Andrea, as someone I once had to call "Mommy", when I was draped over her knee, dressed like a little girl. I now had a better understand of what it felt like on this side of the hairbrush, the pride, the caring and nurturing of your submissive...it was a lot of work, but well worth the return on investment. 

I wanted to tell Mistress all about tonight, I wanted her to be proud of me and what I was blossoming into. 

I text her a picture with no further description or details, just this: 

Moments later, my phone on the counter buzzed to life. 

Mistress asked a few more details, I shared mostly everything. In our particular arrangement, it is thrilling, butterfly causing and humiliating for Russell to know that another woman, or several women, are aware he is spanked, kept in chastity and as of tonight, "forcibly" feminized. It was part of our contract that he is owned by me, but must obey the likes of Mistress Andrea, Summer and if she ever comes back to Canada, Cassandra. 

A "surprise" at Mistress Andrea's Facility usually meant I'd be leaving there sore, degraded, humiliated and blissfully indulged, in all my kinky cravings. But after this role-switching with Russell, I'm not sure I'm in the right headspace for one of the Facility's many surprises. Lucky, Mistress put my mind and my heart, quickly at ease. 

Coffee-talk sounded nice, just Andrea and I...

But my mind was reeling with self-doubt, almost like I was intimidated, but I shouldn't be, should I? 

Am I really one of them now, have I been turned to the dark side? 

Am I a female Dominatrix?

Sarah Jane 💟

Continued in: Little Spoon

 

Ponytail

Continued from: Back to School

A Sarah Jane story: Ponytail

Hello everyone, it's Sarah Jane writing to you, under Mistress Andrea's strict instruction. I just came back from the stables, having completed my first day of pony training. I'll try to write about it now...I might be a little lost for words though. I still feel so degraded and ashamed about the whole situation. About how something so humiliating, betrays my naughty cunt so badly. I fuckin' hate her right now! I hate when my cunt does this to me, betraying and exposing me like this. I don't know whether to cry right now, or throw my legs in the air and masturbate. My mind is so messed up...conflicted. 

I guess I'll start with the initial conversation I had with Bella, when I first descended into the dungeon space of The Facility and found Bella near the stables, waiting for me. My only instructions from Mistress was to arrive naked, with my hair done in a high-pony. 

She's always so Goddamn elegant and gorgeous. She's intimidating to be around, and now she was holding a horsewhip. 

"Are you going to whip me, Bella? Or Ma'am? What am I required to call you?" I nervously asked her, ignorant of the protocols of pony training. 

"No Honey. I am not going to whip you and you don't call me anything. I am a slave also, remember?"   

"In-fact, you and I aren't allowed to speak to each other at all. When Mistress arrives just keep your eyes down and listen for her commands." 

"So, you've done this before, Bella? What's it like? Is all this necessary, this horse training?" 

I watched her eyes glaze-over with moisture, as her gaze became distant, like she was accessing some horrible, traumatic memory.

 

In an emotionally-shaky voice, she responded. 

"It's...*sigh*...it's dreadfully humiliating, what you're about to experience, Sarah."

She paused, dramatically, allowing my suspense, curiosity and butterflies to frenzy.

"But if you're anything like me, when it comes to humiliation, Sarah...well, you know...what it does to people like us?" 

She blushed deeply, unable to hide her shame as she eluded to involuntary arousal. 

"So I have to become a horse, or act like one? In order to feel more humiliated?" 

"No, no Honey. Pony training is much more than that. It teaches you how to move gracefully and elegantly, with deliberate purpose. It accentuates your sexuality, by framing and presenting your most intimate areas. It strengthens and elongates your legs, tightens your bum and works your core." 

"Despite how terribly humiliating it is, it's meant to prepare you for the elegance and grace that is required in the Upper Floor."

"And you'll be here too, Bella? In the stables?"

"Yes. When Mistress trains you she likes having a witness to your humiliation. Pony training down here is always done in pairs."

I think I audibly groaned, like a total whore, at the realization Bella would bear witness to whatever awaited me. 

"Now c'mon, quick. Get into your stall. Mistress will punish us both if we're out of position. 

I soon found myself in a strappado pose, with a spreader bar forcing my legs open and a pony bit in my mouth. 

Everything was facing my stall door and on display. My dripping cunt, my puckered asshole, I felt so exposed and aroused at the same time. Bella told me she'd be right outside the door, then she told me to be brave. That was the last time we spoke to one another for the rest of the session. Mistress Andrea was coming down the hall. 

As I dangled, helpless in my stall, bound and gagged...my mind was racing. That line freaked me out. What exactly was I in for here? 

And WTF did she mean?! "Be brave"...??!

I guess I was about to find out. I could hear commanding boot-clicks against the floors outside my stall. 

My trainer had arrived...

To be continued. 

sarah jane xoxo

Continued in: The Stable Master