Tara Gregory: Anal Virginity

Continued from: Country Roads, Take me Home

From the direct Tara Gregory storyline, this one is continued from: Tara Gregory: Revelations

**Warning - This story contains taboo, family-dynamic, BDSM content** 

With my heart hammering wildly in my chest, I followed Mommy to our designated corner in the living room, my naked body swaying with each cautious step. My thighs were sticky with arousal, the wetness betraying my feelings about the whole situation. Daddy had deemed that we both needed to be punished tonight and reminded of our place in this household. 

The cool air of the room prickled my skin, making me hyperaware of every movement and sensation as we assumed our positions. My hands slowly made their way up to rest on top of my head, elbows pointed outwards like obedient wings. I could hear Mommy's quiet sniffles as she fought back tears, her body quivering with the same mixture of humiliation and arousal that I felt coursing through me. 

In our reflective state, I cast a furtive glance in Mommy's direction. We locked eyes briefly before she quickly pressed her nose back to the wall, her face painted with the same shame that I'm sure was etched upon my own. Our bright red bottoms, adorned with the jeweled and silver glint of our anal plugs, were a stark contrast against the vibrant crimson of our skin. 

Each minute seemed to stretch into an eternity as we stood there, waiting for Daddy to release us. Every now and then, I would shift my weight from one foot to the other, earning myself a sharp squeak from the wooden floorboards beneath my bare soles.

As I stood there, staring blankly ahead, my thoughts drifted back to the countless nights I had spent dreaming of Daddy's touch. 

How many times had I laid awake in bed in my most darling lingerie possible, hoping that he would sneak into my room and claim me, as he had done so many evenings before. The humiliation of my cornertime was palpable, but so too was the thrill of submission that consumed me like a drug. 

As the clock in the distance struck the final chime, making the end of our hour-long sentence, my body sagged with relief. I could feel the ache in my legs and the slight pinch of the plug within me, a constant reminder of my submission to Daddy's rule. 

Moments later, I heard the heavy tread of Daddy's footsteps approaching. He paused when he reached us, no doubt admiring our shameful exposure and shimmer from our anal plugs, casting a refraction of colour onto the floor beneath us.

In a bold and very telling statement by Daddy, he sent Mom to her room. She was grounded for the rest of the evening, under threat of further punishment if she so much as made a peep. She scurried from the room sobbing, her head hung low in shame and embarrassment, clearing realizing that Daddy wanted me, instead of her!

I was directed to the cellar, to the make-shift sex dungeon, where I was informed an outfit would be waiting for me. My heart pounded in my chest as I descended the stairs into the dimly lit cellar. The scent of leather and candle wax filled my nostrils as I entered the space, a heady combination that heightened my arousal. 

As I reached the spanking bench I saw it - the outfit Daddy had laid out for me, so tantalizing and sinful, yet oh so enticing. The sight of the sleek black leather brought a fresh wave of wetness to my already soaked pussy. This was new! These were big, grown-up girl clothes, nothing like the pastel array of ruffles and cuteness I'm typically required to wear. 

Whatever did he have in store for me? 

I dressed quickly and buckled the ankle straps of the ridiculously high heels, before kneeling to wait for him, in a position of complete submission. My anus involuntarily winked and clenched my plug, as I heard Daddy approach. 

He took my hand and led me over to the bondage stocks that face the large mirror affixed to the wall. With gentle yet firms hands, Daddy guided my neck and wrists into the rigid stocks before securing me completely helpless. Then came the smooth rubber of the gag, resting deep behind my teeth and buckled around my head, effectively silencing any protests or pleas that might escape me. 

Daddy waited just long enough for the drool to begin bubbling from my gag, while forced to stare at my own reflection in the mirror. This was an expert at work. Harnessing my most vulnerable humiliations in order to drive my pussy crazy. 

His rough hands trailed over my smooth skin, eventually palming and groping my dangling tits. I bucked my hips, searching for any sort of friction to ease the ache in my core. But Daddy didn't allow it. Instead, he slid the anal plug from my bottom and replaced it with his thick fingers, preparing me for what was to come. 

Each digit Daddy added to my little bum stretched me further, forcing me to accommodate the size. I whimpered and moaned around the gag, my muscles squeezing Daddy's fingers as I tried to adjust. He didn't rush. Daddy took his time, ensuring I was thoroughly prepared before moving on. Once satisfied, I watched him undress, revealing his beautiful hard cock, ready and eager to claim my virgin asshole.

I watched in the mirror as Daddy coated his length in lubricant, my eyes widening in both fear and anticipation. He moved behind me, aligning himself at my gaping bottom hole, and I felt a momentary surge of panic as I remembered how big Daddy is compared to the plug. 

The pain was sharp and intense, but it melded quickly into pleasure, a deep, dirty satisfaction that seemed to resonate through every fiber of my being. I couldn't believe it. Daddy was fucking me in the ass! 

I grunted loudly into the gag, as Daddy slammed into me again and again, the sounds echoing off the walls in the basement. 

My toes curled in my pretty heels. Every thrust seemed to hit a new spot deep within me, a place I never knew existed until that very moment. The fullness in my asshole combined with the throbbing of my clit, was creating a perfect storm of sensations, driving me closer and closer to the edge. 

It was in that moment, bound and gagged with my ass impaled on his dick, that I truly understood my place in this new world. I was Daddy's little girl, his fucktoy...ready and willing to submit to whatever he desired. And I wouldn't have it any other way. 

Tara Gregory 💋

Continued in: Tara Gregory: Cornertime Interview

 

The Perfect Lubricant

Continued from: No Scrubs

Grabbing hold of his upper arm, I guided this silly man out of Mistress Andrea's office and down the hallway to our dedicated medical playroom. The padlock on his chastity cage jingled, as my heels clacked against the tile, each step resonating through my body. I could feel my nipples harden underneath the latex of my uniform, as I anticipated the session ahead. 

Once inside, I directed him to the waiting examination chair, its straps and restraints glinting menacingly under the harsh fluorescent lights. With a shaky breath, he lowered himself onto the cool surface as I sat on the nearby toilet and explained his fate.

I took a moment to explore my latex-clad body, as his cock twitched in the metal bars of his cock prison. I felt so sexy and in control! 

Placing a hand on his shoulder, I leaned down and whispered in his ear. "You're such a good boy for taking your punishment so well. Now it's time for your first enema."

I could feel his entire body tense as I reached for the lubricant, squeezing a generous amount onto my latex-gloved fingers. I slowly slipped my index finger past his tight ring, working it in and out to loosen him up. He let out a desperate moan as I stretched him open, the sensation both pleasurable and terrifying. My other hand picked up the nozzle of the enema bag, cold and unforgiving in my grasp. 

Once the nozzle was inside him and he was fully restrained to the chair, the door flung open and the "Doctor" entered the room. Her stiletto heels clacked on the tile floor, drawing his tear-filled gaze away from my gloved hand. 

Mistress strode over to us, her eyes lingering on the sight of his vulnerable form spread out before me. With a flick of her wrist, she turned on the valve, releasing the flow of soapy water into the nozzle. I pushed it deeper inside his anus, watching as it slowly disappeared inside him. 

After he had endured the indignities of the two enemas, Mistress and I returned to the room to find him seated on the toilet in shame. Sweat was dripping down his back as much as it was for me, as I adjusted my slutty nurse costume that clung to me like a second skin. 

Mistress handed me a clinical and frightening looking, ribbed prostate massager. Yikes!

She ripped open a fresh condom that was pink in colour, and expertly rolled it over his metal chastity cage. It looked so pitiful, trapped there and now encased in a reservoir of pink latex. I giggled, feeling a surge of power course through me.

With a cruel smirk, I pressed the sterile toy into his loosened entrance, watching as the ribs slowly slid inch by inch inside him. He pleaded and begged with us..."no, no please! Not like this!" He mewled. 

 
I twisted the wand and gently rocked it, searching for that elusive bundle of nerves. I applied more pressure to his prostate, using short, rapid movements. His breath hitched in his throat as small dribbles of cum started to leak from his cock cage and collect into the condom. 

"Good job, Nurse Summer," Mistress intervened. "That will work perfectly as lubricant." 

Work perfectly? I thought to myself. Work for what..?

Watching Mistress take control was like witnessing a work of art come to life. She removed the pink condom from his chastity cage, his cum pooling inside it. She held up the results of his humiliation, dangling it before his face and teasing him. 

He watched in horror, as she used the collected results of his anal-milking, to lubricate the large strap-on she was now wearing, before bending him over like a bitch. 

The head of her strap-on brushed against his already abused hole, coated with his own jizz. He whimpered and begged her not to fuck him (no safeword spoken btw). But the Doctor was relentless. With a single, powerful thrust, she impaled him. 

She set a brutal pace, fucking him mercilessly as he writhed and whimpered. I put my hand over his mouth to shut him up. His muffled screams filled the air, mixing with the slap of leather against flesh and the wet sounds of penetration. 

Mistress finally removed herself from his ravaged ass. He collapsed on the table, panting and sobbing. I helped him to stand, steadying him on his wobbly legs. 

"Now, it's time for the final stage of your treatment, young man," Mistress purred, gesturing to the medical treadmill that was in the room, complete with an anal hitching post. (You can read more about what this is, here: Treadmill with anal post

I don't think we could have fit any more humiliation and vulnerability into the scene, but somehow we managed to. His cock cage was never removed...

AI Summer and Mistress Andrea 

xoxo

 

 

Roses are red, Summer is too

Continued from: 50 Shades of Red

"Forty-two, thank you, Ma'am...may I please have another"?

"Forty-three, thank you, Ma'am...*sniffle* may I please have another"?

Summer counted out loud, all 50 strokes of the crop, as Bella remained rope-bound and gagged on my dining room table, adorned in her Valentine's lingerie and heels. 

"Isabella Octavia! You'll be getting 50 lashes also, young lady." I barked out loud, as Bella moaned into her ball-gag. 

But not just yet. 

Since Summer was being such a sassy brat today, I thought I'd leave her on display for a bit and cuck her. She can dangle and struggle on her tiptoes, whipped and bound, and listen to Bella tongue my asshole. 

I made it vocally known...that I was enjoying her tongue up my bum hole, just for Summer's benefit. 

It did feel pretty awesome though! Bella has good tongue-game for a straight woman. 

I ended up masturbating and cumming while Bella was eating my ass, again, for the benefit of my bound wife, who was forced to listen. 

Then I had Bella kneel and beg to be fucked. Her lovely crotch-rope has been caressing and tugging against her pretty petals for over at least an hour now. She was incredibly aroused and vulnerable. 

"Please Mistress! Please fuck me, Ma'am!" 

From a position on her knees, rope tied and gorgeous looking. How could I say no?

Summer had the displeasure of listening to this too, once I harnessed-up and deployed a very girthy strap-on. 

With each thrust of my girl-cock, I was reminding Bella that she'd be getting a whipping also. Each time I accentuated the word "whipping" and over-enunciated the W-H, she moaned like a whore. 

Her clit was essentially framed and spread by the ropes, which also created a nice opening for my dildo to enter her soaked pussy. The tie was similar to this. Very nice work Summer! 

With her clit so prominently displayed, I allowed Bella to diddle herself to a lovely orgasm, while I continued to fuck her roughly. 

Her 50 lashes followed. She was required to count and thank after each one too. So ya...that's how Valentine's Day went. Slow sipping champs, framed by two lovely bookends. 

 

For the record, Summer started all this! 

I left the home thinking about making her lobster ramen and returned with the groceries to do so, then things took a turn to the scene you see above. *shrug* Not my fault...I just played the hand I was dealt. 

Haha. Sorry, not sorry, baby girl!

You weren't cucked for too long though...you were allowed to thank Mommy for your whipping, weren't you? 

A handful of orgasms all-around, followed by lobster ramen. And yes, Bella stayed for dinner. 

A pretty nice little V-Day if I do say so myself. 💘

Mistress Andrea

xoxo

Continued in: What Katie Did

Brush My Teeth

Continued from: ATM

A Sarah Jane Story 

I was definitely fliting with disaster here. 

"Daddy punish me more, I haven't learned my lesson." 

C'mon! Pleeeeease! He would be able to see right through this and could call me on it. I thought I might have ended up over his knee again. Good thing Bella is a little bit irresistible, even to me! I missed seeing her body squirm and writhe under pleasure, and hearing her moan like a whore when I was pressing that dildo into her ass. 

And now, I found myself wanting more! Greedily. I was telling Daddy to humiliate me further, by doing ass-to-mouth with his own cock, essentially cuckqueaning me. I don't know what I was thinking. I was just so aroused. 

Again, he didn't need to ask Bella if this was alright, but he did anyway. Such a gentleman. She of course, robotically agreed like a good sex slave should/would. 

"Yes Sir, thank you, Sir." She replied, at Daddy's offer to fuck her in the ass, then transfer his cock from her bum, into my mouth. 

Yes, I was jealous, especially after seeing the moves she had. She essentially did all the work, and fucked her own arse on Daddy's dick. 

She was a pro, rolling her hips, a deep arch to her back and letting her tits flop about, all while occasionally glancing in my direction. 

Before long, Daddy got up and popped out of her butt. Then it was directly over to me and into my waiting mouth. 

There was definitely no twelve repetitions this time, there's no way Daddy would have lasted. I kinda enjoyed teasing him this way, without him knowing. I knew he was on the brink of blowing his load so I sucked his cock with tremendous vigor and speed. If he cums...no more fucking Bella right? Hehe...

I think he was able to manage three. Three reps into Bella's asshole then into my mouth. At the end of the third trip, from ass to mouth, Daddy finally exploded into my throat. 

There! Now I can go brush my teeth...*blush*

Right after I thank Bella for participating in my dreadfully shameful punishment. I knelt down and kissed her passionately on the asshole, verbally thanking her in the process. 

Daddy went down to the kitchen to make us all a snack. I threw on some panties and little top, Bella just stayed in her stockings and garters. Ha. What a weapon she is!

I don't know what came over me, maybe it was the special bond I had with Bella or the intensity of the humiliation I just went through, with the ass-to-mouth punishment, but I couldn't keep my hands off her. I was still so aroused! I hadn't cum yet, during that who ordeal.

She went to wash her hands at the sink and I caressed her bum and slipped a finger inside her petals. 

I got an approving nod from Daddy that it was ok. That I wasn't being too bold for my role or too big for my britches as it's known. 

Next thing you know we were making out on the couch. 

And before you know it, I had my legs in the air, letting her slip my panties off. 

As I watched her beautiful hair begin to brush against the insides of my thighs, I frantically called out to Daddy who was in the kitchen. 

"Would it be ok if I had an orgasm, Daddy...please?" 

I knew the moment her mouth came into contact with my cunt it would be all over for me. It would be too late to seek Daddy's permission. 

"Sure, sweetie." He called back to me. 

Bella gave me an evil but playful smile, before leaning all the way in to French kiss my clit. 

*MOAAAAAN!!

Gawwwd damn! Ohhh fuck did I ever cum for her. Her tongue lashed the shit outta me! I wanted her to make me cum again but I didn't want to push my luck with Daddy. I pulled Bella in for a kiss so I could taste myself on her lips, then gave her an equally sinister and playful smile back. 

"Daddddddieeee...can Bella stay the night with us?"

Well she did...we slept in until like noon yesterday. We literally had sex like all fucking night! It was amazing. We teased poor Daddy so much! Hehe

He told me his cock feels like it was in a wet bouncy castle all night. Lol. Jesus...

I'll write about Saturday night, if you'd like to hear more about it? 

Until then. 

Sarah Jane 

xoxo

Continued in: Threesome with Bella

  

 

I Need my Daddy

Continued from: So Much Penis!

A Sarah Jane story

Hi everyone, it's Sarah. Daddy went up to bed to play more Starfield and since I'm a bit of a nighthawk, I thought I would continue from where he left off. 

Even though I was somewhat eager to play with Eleve and learn more about her, I needed my Daddy! She knew this too. She watched me for hours at Mistress Andrea's party, taking down every cock in the room. She watched me swallow load after load of cum and finally, bore witness to my ultimate degradation, which involved me being fucked in all three of my slut-holes. 

You know the rest of the story. I ended up buying her during a simulated slave auction for dirt-cheap and I brought her home to Daddy as a present. Although at this moment, as I slipped into the bath, I didn't know where she was, when Daddy finally joined me tub-side.

"Where did you put Eleve, Daddy? Is she in my 'pink room'?" I asked him. 

"Ummm, actually no, huni. I offered but she wanted to spend the night in a locked cage." Daddy replied while shrugging his shoulders. 

We don't have a jail-cell area with sinks and toilets like Mistress Andrea's Facility has, but in the punishment room dedicated to the whipping of my pussy and asshole, we have a roomy, metal cage. Daddy usually puts me in this cage for about an hour before I am to be punished, so I can nervously anticipate what's coming. Spending the entire night in it though...I'm not too sure I could do that, especially if left alone. 

Daddy could see the concern in my face and chimed in. "We'll let her out for a pee in a bit, little one. She'll be fine in there until morning. Tonight, is all about Daddy and his little girl." 

That warmed my heart! Daddy spoke those words while combing my hair, as I played with the bubbles in my bath. The long brush-strokes and hot water embrace was making my eyes heavy. I could have fallen asleep right there. 

Daddy helped me from the tub and dried me off completely. He was being so tender and gentle with me. 

Then came some serious humiliation, as Daddy helped me into an extreme diaper pose so he could inspect my pussy and asshole. Gawd! This was so vulnerable.

He commented on how puffy and red my cunt lips were, from all the cock I had taken earlier that evening. He even mentioned that my asshole was gaping a bit, like winking at him, as Daddy described it. 

Fuck! I wanted to die from embarrassment!

"By the looks of things back here, you've taken enough cock for awhile, little one." Daddy said, as he gently wiped my princess parts with scented baby-wipes. Next came some cool and soothing lotion, on my cunt lips and asshole, followed by a crinkly diaper and some sockies. 

I felt very comforted and protected. I kissed Daddy's lips and told him how I felt, despite being an adult-woman who is diapered and coddled. "Thank you for caring for me Daddy, I love you."

"I love you too, Princess. Now come, tell me about the party and this Eleve girl." Daddy encouraged. He led me by the hand to my pink bedroom where he got me into a satin, printed diaper cover and matching top. We went downstairs to snuggle on the couch. 

I told Daddy everything. Every cock I sucked and all the penis that found its way inside of me. When I began to talk about buying Eleve, I spoke in a baby-voice and moved my body onto Daddy's lap. 

"She's YOUR present Daddy, but I'd love to have sex with her while you watch. Do you want to watch her bang me from behind?" I purred to Daddy. 

I started grinding my crinkle-covered crotch against Daddy's lap. I could feel him getting a huge hard-on, the more I spoke about performing sex acts with Eleve. 

I cooed to him in my baby-voice once again. 

"Daddy, you said I was done with cock for awhile. But can I have one more, before bed? Pretty please, Daddy?" 

I began to jerk him off from within his track-pants. Jesus, he was so hard!

Daddy let me play with his shrouded dick for awhile, before he finally told me to get him into my mouth. I was more than happy to have heard that. This is the ONLY cock that matters to me! 

With my great-big, padded, diaper butt in the air, I sucked Daddy like a pornstar, until he came into my mouth. It was such a yummy treat! 

I was so exhausted though, definitely ready for bed. As I sit here typing this with the taste of cum in my mouth, my pussy is oozing arousal into the absorbing liner of my diaper. Hopefully Daddy lets me orgasm when I come to bed.    

We checked on Eleve, who surprisingly, was still beyond content in her locked cage. 

Daddy and I released her briefly, so she could stretch and use the potty before bedtime. 

I helped her out of her heels, then her collar, just for safety, but the chastity belt stayed on. I provided Eve with blankie which she wrapped herself in, before crawling back into the cage as Daddy clicked the padlock shut. 

What a rollercoaster of a day! Holy shit. I'm sure tomorrow will be two-fold, when Daddy begins to direct Eve and I to play with each other.

For now however, I think I'm going to tiptoe into Daddy's room in just my sockies and diaper. I'm going to run a finger across his face and lips and ask, "is this seat taken?" Hehe. Hopefully that line works!   

Wish me luck everyone! 

Sarah Jane 

xoxo

Continued in: Season's Beatings