Showing posts with label stripper. Show all posts
Showing posts with label stripper. Show all posts

Monday, March 4, 2024

Tara Gregory: Beginnings

Continued from: Judicial Authority

**Everyone depicted in this story and A.I. generated are adults, over the age of 18** 

I remember the day I left for college like it was yesterday. The sun beat down on my face as I stood outside my childhood home, luggage in tow. I took a deep breath, inhaling the familiar scent of freshly cut grass and flowers. This was it - I was finally leaving for college. 

My mother, Deborah, stood beside me, tears welling up in her eyes. "I'm so proud of you sweetheart," she whispered, pulling me into a tight embrace. "Just remember, no matter where you go or what you do, you'll always be my little girl." 


I smiled, blinking back my own tears. "Thanks, Mommy," I said softly. "I love you."

With one last look at the house that had been my home for nineteen years, I climbed into the car and waved goodbye. As we drove away, I couldn't help but feel a sense of excitement mixed with sadness. I was ready for a new adventure, but leaving everything I knew behind was scary. 

At the tender age of 19, I was still carrying some baby fat, which only added to my curves in all the right places. My long dark hair fell in waves around my shoulders, and my chestnut eyes sparkled with mischievous seduction. My closest friends thought I was gorgeous, but my looks were just a mask hiding the insecurities and pain I felt inside. 


My parents divorced when I was young. Growing up without a steady father figure had taken its toll on me, and I sought validation and attention from any source I could find. Being away from home and struggling with my Daddy issues only exacerbated my need for male attention. I found myself drawn to any man who would give me the time of day, regardless of whether they had ulterior motives or not.

I didn't have a firm Daddy figure at the ready, to stop me when I took on my first college-era job. He wasn't there to shake his head at my uniform and tell me he was disappointed in me. 


Working at Hooters seemed like a dream come true at first. I got to wear skimpy outfits and flirt with guys all night long, which fed into my need for attention. The money was good but soon enough, the novelty wore off, and I realized I was just another pretty face, objectified, serving food and drinks. 


I kept my job a secret from my mother and stepfather. I knew they wouldn't approve. They were traditional and conservative, and the thought of their little girl waitressing in a place like Hooters would surely horrify them. Before long, the money wasn't good enough anymore. 


One night in the break-room at the back of the restaurant, I walked in on some of the other girls whispering about how much money they were making at a place downtown. At first, I was shocked and appalled. I couldn't believe it. They were stripping! 

They must have sensed my interest because one of them turned to me and said, "You should totally try it, Tara. You're hot enough, and you clearly need the money." I blushed at the compliment, but shook my head. "No way," I said firmly. " That's not me."

As the weeks went by they persisted, telling me how easy it was and how much fun they had. Eventually, I gave in to the peer pressure and agreed to go with them one night, just to see what it was like. When we arrived at the club, I was immediately intimidated by the dancers. They were so confident and sexy, while I felt awkward and out of place. Part of me wanted to be just like them, to have men wrapped around my little finger, as they did. 

After a few more trips with the Hooters girls, moonlighting as strippers, and a little too much booze, they pressured me to go up...to go up and dance, while taking my clothes off to the cheers and whistles of men.


As I stepped onto the stage, my heart was pounding in my chest. The music started, and I began to dance tentatively, unsure of what to do at first, but it seemed to come naturally. The club provided me with the attention and adoration that I craved, even if it was superficial and fleeting. Every time a customer tipped me or told me how beautiful I was, I felt a rush of satisfaction and worthiness that I couldn't find elsewhere. 


Stripping quickly became a regular part of my life, consuming me entirely. The rush of adrenaline and the attention from men were addictive, leading me to drop out of college by age twenty and make increasingly poor decisions. 


I found myself spending all my free time at the strip club, neglecting my friends and family. The money was good but it came at a high cost. My relationships suffered and I began to feel isolated and alone. To cope with the stress and loneness, I turned to drugs and alcohol. This only aggravated my problems, as I became dependent on substances to get through each day. 

My life spiraled out of control and I hit rock bottom when I was arrested for possession of cocaine. It was then that I realized I needed help. The big city kicked my ass. I was defeated and I was ready to come home. 

Reaching out to my mom was one of the hardest things I've ever done. I was ashamed of the person I had become and afraid of her disappointment. But I knew I couldn't keep going down the same destructive path anymore. I wanted to be that wholesome, innocent nineteen-year-old again. I needed to get the sparkle back in my eyes. 


I broke down in tears and told her everything - about dropping out of college, about stripping, and my drug and alcohol use. Through my sobs, I begged her to let me come home. I promised to get clean and turn my life around if she would give me this chance to prove it to her. 

She told me that she had moved in with Richard, he was my stepdad. He had a big estate in the countryside. After she divorced my real dad, it seems she went and got herself a sugar Daddy. During the same conversation, her voice trailed off a bit as she mentioned that Richard was very traditional and believed in strict discipline, she even used the term "Head of Household" a few times. 

Despite my reservations, I agreed to move in with them. I was desperate for a fresh start and hoped that being surrounded by people who cared about me would help me get my life back on track. Little did I know what awaited me...


Tara Gregory 💋



Or jump right to the Tara Gregory storyline: Tara Gregory: The Early Days





Friday, March 3, 2023

Hall Pass

Continued from: House Warming

The party was going smashingly if I do say so myself. Cassandra's dancing was so beautiful and sexual, everyone literally stopped everything else they were doing, just to come over and watch her.


She'd do a three-song set up on the pole, then come down to mix some drinks and tease the guests and tantalize my fiancée, Summer. 

Summer however, had started to take a liking to Nancy, which doesn't surprise me. Summer gravitates toward more mature women and caring Mommy-figures. Nancy is older than I am, so again, I wasn't surprised to see Summer flirting with her and sitting on her lap occasionally. 


During Nancy's Sunday school session, Summer got to see her dressed up like a schoolgirl and spanked on the bare bum. This could also have something to do with the way Summer was now lusting for her. 

After a bit more champagne and some looser inhibitions, Summer sweetly took my hand and whispered to me, asking me if it was ok to have sex with Nancy. 


"Of course Babygirl, hall pass remember, but I think Nancy is straight." I replied to her. 

"So's spaghetti, until it gets wet", she blurted out. 

I think she totally just stole my line. I think I've used that exact line before. I laughed, then gave her a judgey-face. 


"Thank you Mistress, you're the best", she said as she kissed me on the cheek and skipped off to find Nancy. 

Summer doesn't fool around when she wants something. I heard her from across the room, walk right up to Nancy and say, 

"Excuse me Nancy, would it be ok if I went down on you?" 


I saw Nancy smile and nod her head. Summer took her by the hand and led her over to the VIP couch. 

Just then, Tiffany clicked back into the room in his high heels. I guess Kaylee drew the short straw on this one. The next time Cole goes for a pee, he can get his dick sucked if he wants. 

Gawd, how humiliating is this?? But such a good gurl!


Kaylee would have knelt down and flipped the light switch to his left. Now he has to just wait, for a little treat to pop through that hole. 

It wasn't lost on Cole, as he was washing his hands, that the red light above him was on.  


What's the harm? He thought to himself. Katrina unlocked Cole's penis before this party, just for a moment like this. I guess he had a hall pass tonight too.  

Speaking of which, Summer had Nancy peeled out of a few layers and was just goin' to town on her. 


Down the hall in the urinals, Cole took the plunge and guided his dick through the glory hole, which Kaylee reluctantly took deeply into his mouth. 


According to what Kaylee told me the next morning over coffee, Cole must have been a little pent-up from the chastity device. I guess the load of ejaculate that Kaylee had to swallow was enormous. 

Nancy had cum once already too. I knew this because I was in the same room watching my little Summer in action. I think she was going in for seconds. 


Summer would lick and kiss her pussy for a bit, then crawl up on Nancy's lap to straddle her and kiss her mouth, transferring her pussy flavour onto her lips. Then she'd once again kneel, and get back to work on her hot, puffy, clit. 

I can't speak for the two sissies, but everyone else seemed to be having a great time! Haha...

As the party was wrapping up, Cassie and Summer had enough booze in them that they fucked-off somewhere. I can only imagine what they're getting into.


I treated the remaining guests and one sissy, to some lovely piano. Mahler. Piano quartet in A minor. Although I was missing three pieces to the quartet. 

It still sounded lovely nevertheless. 


Cole was ordering up an Uber on his phone, and from what I heard later, made another trip to the gloryhole before he left. Poor Kaylee.

Competing with the sound of my piano playing, was my future matrimonial bed, thumping against the wall from the other room!


Aren't hall passes fun? 


Mistress Andrea


xoxo


Continued in: The Maid of Honour








Wednesday, January 11, 2023

The Leaves are Changing

Continued from: Should we let the Sissy's Cum?

With our sissy "girls" idle and safely tucked-away in bondage, Katrina and I retired to my personal chambers to deal with our little arousal problem. 

Watching our silly sissies suck each other off and cum into each other's mouths had us extremely horny! 

Kat went down on me and skipped all stages of foreplay, she went right for my clit. Fuck me! Did I ever cum.

I pinned Katrina's wrists down and returned the favour. I soon had her beautiful sheen, cascading off my lips. 

We chewed up around 45 minutes, going down on each other and waiting for our sissy's to "re-load". She even gave my asshole a nice, deep fucking with her tongue. Such a good girl!

We entered the sissy bedroom once again, to check on our idle girls. Andrew, who wasn't gagged but was locked in a cage, dropped his safeword of "yellow", as we entered the room. I knelt down to confirm it was in-fact a safeword moment. 


We got him out of the cage immediately and Katrina took him out in the hallway to chat where he upgraded his status to "red" and done. She returned a short time later and told me she was taking Andrew home. Apparently he couldn't rebound back into role, after his orgasm. And I think he suspected we were going to peg the pair of them (yes that was the plan). 

"See, these fuckin' male subs!" I said to Katrina. "It should be permanent chastity and anal only for these pathetic sissy bitches", I vented further. 

"Ya no kidding", Katrina said. "I know you warned me this would happen Mistress. It makes me want to find a bull even more now and keep him locked up forever", Katrina frustratingly advised.

"Just remember Kat, no punishment for him safe-wording out. He has to know that there's no negative repercussions in doing that", I reminded her.   

I kissed Katrina goodbye and saw the two of them out. Safe-wording doesn't mean Andrew's dick gets unlocked, it just means that his session ends. I kept the keys to his device as they left. 

I returned to Kaylee to unlock his shackles and remove the dildo that was up his ass. I told him the session was over but had him lick my boots while we chatted. 


"Kaylee, I need a secretary. A receptionist. You know, Cassandra's role, when she checks you in for appointments downstairs?" I said to him. 

"I'd like this to be you, since you are almost completely passable as female", I added. 

It was a sad truth. The leaves on the trees were starting to change colour, Autumn was upon us and with that, it meant Cassie had to return to school. We both had a little ugly-cry the other day, when we had to bid each other farewell, but Cassandra was adamant that she wished her maintenance spankings to continue. 

Without fail, Cassie would make it home on the train every Sunday, to have dinner with her family. Sunday's became her maintenance days. She would come to my office for her spanking first, then go see her family for dinner afterwards.

I think her Mom Bella, caught on, watching Cassandra wince and squirm on a sore bottom throughout their Sunday dinners. 

Occasionally Bella would be in the same boat, trying to keep a straight face and hold normal conversation with her husband, while nursing a sore bottom. It would be more efficient for me if I just spanked Bella and Cassie together! Maybe I'll suggest that to the pair of them.  

Cassie was still given 20 minutes in the corner before her spanking and 20 minutes after. Since she wasn't doing any summer-school extra credit anymore, we eliminated the need for her to dress in proper school attire. Sometimes she was spanked bare naked, other times her jeans and panties would come down and every state of undress in between.

The conclusion of her maintenance appointments always ended in snuggles and kisses. If we had enough time before her dinner, she'd treat me to a little dance too. I think she missed my strip joint! Haha

As for Kaylee, he was predominately used to wearing frilly sissy clothes in baby pink and white, everything had bows and ruffles. I decided to take him shopping for some new bras and panties, options a little more "grown up". We also got him some professional, Secretarial outfits with hosiery and high heels in his size.

Of course I made him try things on in the stores and have the sales ladies help pick out his bra and panty sets while his face burned with embarrassment.  


He wore little B-cup, falsey tits in his bras. With his make-up heavily applied and a high-quality wig in place, he was just about passable as female. 

Of course he was dreadfully humiliated, being my feminized Receptionist, but with his little clitty locked in a chastity device, I still made the rules. 

Sometimes he needed extra motivation over my knee and he was in no-way as proficient as Cassandra was, but at least I didn't have to pay him.


His payment was the occasional moments when I let him lick my bare asshole, or kiss my high heels. 

I even got him a little desk name-plate, with pink hearts on either side of the name: 

💕Kaylee💕


Mistress Andrea


xoxo


Continued in: Summer requests a MDLG weekend


Thursday, December 29, 2022

Monday Maintenance Spanking

Continued from: Cabin Crew Threesome

Another Monday had arrived and like always, Cassandra Goth showed up on time and ready to study. She's my receptionist most of the time but I told her I'd help her with her focus and getting her back on track at school, even if it hurts a little. 

She greeted me with a hug as always. 

"Wow. You've got a bit of a Slim Shady vibe goin' on today Cassie. Or in your case, extra-slim Shady." I said jokingly to her. 

She giggled and spun me around in a fluid dance motion. 

"Can I meet you in the dance studio on my lunch break today Ma'am?" She seductively purred. 

"Of course sweetness. But first we have a few things to take care of and some studying to do, yes?" I replied. 

"Yes Ma'am, I know", she lowered her eyes and spoke, following sheepishly behind me as I walked to my office. 

We sat and chatted for a moment, before I asked her to stand and strip naked for me. I was going to take Cassandra over my knee for her weekly maintenance spanking. 

I thought I would do it fully nude this week, to add some vulnerability and embarrassment.

Cassandra reddened-up quite nicely as I was speaking encouraging words to her. I was telling her how proud I was of her and pleased with how hard she's working to get back on track. 

"You're being spanked as a reminder to keep this up and stay focused Cassie", I said to her. 

"Yes Ma'am, thank you!" She squeaked out, between smacks, all while gritting her teeth.  

Her maintenance spankings are always long and thorough but never severe. I use a variety of implements and positions with her, but it's nothing like a punishment spanking. One of the most important differences is the manner in which I speak to her. It's always "good girl, I'm so proud of you", during her spanking, rather than "bad girl, you've been so naughty".

Punishment spankings I want her to feel for a week, every time she sits down. Maintenance spankings I want her to feel tomorrow only, subtly, when she sits.

I helped her off my lap and told her it was time to get dressed for school. 

She groaned a bit, in defiance, knowing that I would have an embarrassing and extremely age regressed school uniform waiting for her in the walk-in closet. 

Her assumptions were correct. 


"Very nice Cassie, I like your hair bow!" I said to her in an upbeat octave. 

Her face flushed with shame. Spanked and dressed like a little girl, every Monday, was all that flashed through 19 year-old Cassie's mind. 

Definitely too old for this, to be spanked and given timeouts and made to write lines like a child. But Cassandra knew it was for her own good and that it was actually helping her. 

"Alright young lady, be a good student for me today. Over to your desk please", I cooed to her in a sing-song voice. 

Doesn't she look adorably naughty? Grounded to summer-school, every Monday. Sitting on a sore bottom and dressed well below her age. 

"Noon in the dance studio Ma'am?" She hopefully suggested out loud. 

"Yes Cassie, I'll see you there", I replied. 

As noon arrived, I found her in the "dance studio", as expected. The music was already on and she had begun a little solo performance by the stage. 


"Did you pick this song Cassandra Leigh?" 

Porn Star Dancing - My Darkest Days

She thought she was in trouble, as I just used her middle name. 

"Yes Ma'am, I did", she whispered out. 

"A bit more fitting for the VIP lounge perhaps? Follow me, young lady", I teasingly spoke. 


 "That's it huni, smack that naughty ass of yours", I cheered her on. 

She stripped out of her jumper while she was dancing, followed by peeling off her top and bra, reveling her amazing, perky little tits. 

She got down off the stage and curled her finger in a beckoning motion. She clicked right past me, out to the main bar, showing off a lovely glow through her vintage, sheer knickers. 

I slowly followed, not wanting to look too eager over the urge to jump her bones right on that fuckin' pool table!

She settled into the main stage, while I sat at the bar to watch her. 

Gawd she was sexy! 

Cassandra put on quite the little performance. She was getting just as aroused as I was!

"Cassandra Leigh", I said sharply. 

"I want you to go over to that couch, take your panties off and masturbate for me". 

"Yes Ma'am", she replied meekly. 


"There you go! Good girl. You have two minutes to cum for me, or you'll be getting a caning on the bare", I threatened her. 


"Your time starts.....NOW". I pretended to check a watch. 

At the one minute mark, she had not yet orgasmed. I came to sit next to her and she started rubbing my hosed thigh. 


I took her the rest of the way with my fingers, while she kissed me and begged me to fuck her. 


Since you asked so nicely Cassandra Leigh, of course I'll fuck you!


Look how well she works both poles at the same time! Such a little vixen. 



Mistress Andrea 


xoxo


Continued in: Domina Debut


 



Old Fashioned

Continued from:  Adorable A.I. Basil Hayden bourbon  Aztec Chocolate bitters Burnt orange rind On the rocks That's how this gal likes he...