Author: Stephanie
He fidgeted and nervously glanced at his watch as he sat waiting at the restaurant to meet a person willing to provide him an answer to his desire. He couldn’t believe he was doing what he was doing, after-all he was a relatively successful business man and everybody came to him for answers. Nobody who knew him would think that his life was missing some and he had been searching for the answer. He kept glancing at the door hoping the individual would show. He jumped suddenly when his cell phone vibrated. Quickly he picked it up and answered it. “Hello?” He said, but all he got was dead air. Confused, he went to the call log to see whom he might have missed, only to discover the received call was blocked.
The phone call had distracted him so that he didn’t notice the beautiful woman slide into the seat across from him. “Hello Stephanie.” She purred and he dropped his phone startled by her voice. “Hello, Mistress Chianti.” He managed to stammer out. She laughed and said, “Did I surprise you?” “Yes Mistress Chianti you did.” “Good, I love to keep my subs guessing.” She said smiling seductively at his nervousness and continued, “So tell me a little about yourself and why you want me to help you.”
He explained about his work and business and how he was lacking something in his life. He further explained that he had tried dating, but the relations always ended in an unsatisfying manner. Finally he explained the reason he had sought out Mistress Chianti, “You see, I’ve always been attracted by aggressive women and want to explore my submissive side, want to be used and abused for her entertainment.” “Is that all?” she probed. “No, I’d really love to have a woman turn me into her special gurl, her sissy maid slut.” He answered more quietly. She laughed and said, “Don’t worry Stephanie, I’m the one who will make you my gurl. Now we need to order dinner, where’s that waiter?” The waiter was flagged down and they put in the order.
“So Stephanie, how long have you wanted to be a sissy?” Mistress Chianti asked. “Ever since I was a sophomore in college.” He replied. “Really, and all this time you’ve never found a Mistress to make you her slave?” She responded shaking her head slightly. “Well I’m glad I’m the one who’s going to help you realize what a sissy slut you are, and I’ll do it right.” “Thank you Mistress Chianti, I appreciate it.” He responded and she shot back, “And well you should, but you’ll learn how to show your appreciation.” They finished the dinner and he paid the waiter, tipping well. Mistress Chianti noted the tip and said, “You do tip good, and I hope you realize that as my gurl, I expect regular presents showing your appreciation the privilege of being trained by me.” “Yes Mistress Chianti, I do realize that.” He replied as he helped her with her coat and then picked up a small travel bag.
As they walked to the door, she asked, “Where are you staying?” He looked a little shocked and responded, “ You told me not to check in and to take a cab here directly from the airport.” She laughed, “Good, I was just checking to see if you can follow directions and you can.” “Thank you, Mistress Chianti.” He replied as a wave of relief washed over him. He followed her to the back of a very nice BMW and she opened the trunk. “Get in slut.” She ordered. “What?” he responded shocked, to which she slapped his face and said, “Get in, you’re not yet worthy to ride in the car with me, and don’t questions what I order you to do.” “Sorry Mistress.” He answered looking around as he crawled into the trunk. The trunk lid slammed shut and he heard the Mistress laughing as she made her way to the driver’s side.
In total darkness he heard the car start and shift into gear. They hit a bump as the car turned and accelerated. Suddenly a light came on in the trunk and Mistress Chianti’s voice came over a speaker. “Stephanie, since you were able to follow directions about the restaurant, I’ll assume you also purchased the items I told you to and brought them with. Don’t bother answering, I can’t hear you. Remove your clothes and put the items you purchased on. You have roughly 20 minutes to comply before we arrive at our destination.” He struggled to removed his street clothes and pulled out the items he had purchased. Struggling, he put on the bra, panties, garter, nylons and red stiletto heels. The bra, panties, and garter were red and the nylons black. He folded his street clothes and put them into the travel bag along with his watch.
The car slowed and turned. It felt like it traveled a couple of hundred yards before it finally stopped. Steve strained and heard Mistress Chianti’s heel tap out a steady beat on the drive. But they were travelling away from the car. Panic swept over him as he thought he was being abandoned. But then he heard the steps come back and the car door slammed. The car moved forward again and stopped. The sound of the engine echoed and he heard the sound of a garage door closing. The car shut off and the trunk opened. There stood Mistress Chianti who laughed when she saw him. “Good God Stephanie, you are a sight, but we’ll fix that. I see that you shaved as I told you to, very good, now get out of the trunk.” “Thank you Mistress Chianti.” He responded automatically as he worked his way out of the trunk, but stumbled a little as he tried to get his balance in the heels. He quickly glanced around and went to take the travel bag. “Oh leave that slut you’re not going to need that, follow me.” Mistress Chianti said.
“Yes Mistress.” He responded marveling at how quickly he was being conditioned to answer with Mistress attached. They walked across an empty space toward a door, She opened to door and said, “What your step.” He saw her descend a set of stairs that lead to the basement. He followed, holding the rail and looking as he descended into a softly lit room. “Don’t worry Stephanie, I’m just taking you to your quarter.” Mistress Chianti mused. “I’m not worried Mistress.” He replied. “Well you should be, because I do like to discipline my sissies to insure that they adhere to my training.” She laughed. “Yes Mistress, I was mistaking, I’m a little worried.” She laughed even harder, as she opened another door. He followed her into a salon and saw a make-up area, wigs, and nail polishing table. She was watching Stephanie and said, “Now are you starting to worry?” “Yes Mistress, but I crossed the threshold so now I’m yours.” He replied. Good Answer.” She answered as she exited the salon through another door.
As he passed through that door he found himself standing in the laundry room. He looked around and Mistress Chianti took two steps to another door. “Stephanie, here’s your room.” She advised as she walked in and he followed. He saw it was like a small hotel room with a single bed covered with a pink quilt, a nightstand and light, a small bathroom with shower, sink and toilet, and an armoire. “Mistress Chianti, this is nice.” He commented. “Of course it is, I want you well rested for the training.” She responded curtly. “Now follow me.” She said. “Make sure to close your door.” “Yes Mistress.” He responded and turned to close the door. He quickly caught up with Mistress Chianti as she started to enter the door to the salon he passed through before.
As he came into the brightness of the salon, Mistress Chianti said. “this is where you’ll transformed into my sissy slut gurl, but we have to prepare you before you get here, follow me.” “Yes Mistress Chianti.” He replied quickly following here through another door. There before him was a room lit by soft red lights with whips, cuffs, harness and stocks lining the walls. He gasped slightly and Mistress Chianti responded, “Yes it is breath taking now get over here slut.” “Yes Mistress.” He replied quickly moving to where she had pointed. She moved to the wall and grabbed a spreader bar, various leather cuffs and a penis gag. She swiftly moved back to him and put the leather cuffs on his wrists and attached them to a bar suspended over his head. She then put cuffs on his ankles and attached the spreader bar to each ankle cuff. Standing up she ask, “Is that comfortable?” “Yes Mistress.” He replied. “Well it’s not suppose to be.” She said as she walked to a rope tied to the wall. Untying it she began to pull it and he felt himself being raised until he was on his tip toes. “There is that better?” She asked again. “Yes Mistress.” “A little uncomfortable, maybe.” “Yes Mistress, it is.” “Who cares.” She laughed and came back in front of him. “Open your mouth slut.” She ordered. “Yes Mistress.” He replied and she thrust the penis gag into his mouth. He gagged a little and she laugh.
She then walked behind him and he heard her taking something off the wall. Suddenly he heard the sound of the air splitting and felt a sharp pain across his ass. He flinched and she laughed , “Can’t get away can you? But this is how I prepare you to be the slut I want you to be, I break you down and build you up.” She applied a few more strokes across his ass then just as quickly as it started it stopped. He heard her move back to the wall. This time she returned and moved around to his front. She was holding a cock and ball harness and several objects on short chains. She quickly installed the harness on his worthless manhood and began attaching the objects to the harness. “These are weights slut and they are there for my entertainment, not yours. Nod if you understand.” She said with a slight lilt in her voice. He nodded and groaned slightly as the weight began to pull down on him. She laughed and gave the weights a shove with her foot, causing him more pain.
She went out of his field of vision again and when she returned she had nipple clamps and clothes pins. She pulled his bra down roughly and applied the nipple clamps. She then knelt down and hummed softly as she applied clothes pins to the exposed parts of his penis and scrotum. His groin felt like it was on fire, between the pain of the weights and the application of clothes pins. She looked up at his face and laughed. “I can see you’re enjoying this, but you know what, something’s missing.” She stood up and removed the penis gag, then quickly turned towards a roll-around cart. She opened up a drawer and pulled out various make-up containers, brushes, and applicators. She took up a foundation and brush and looking at stephanie’s face began to apply it. “Stay still bitch, otherwise you’ll mess it up.” She hissed at him. “Yes Mistress Chianti.” He replied realizing that his jaw hurt from the penis gag.
She worked swiftly and finished the make-up by applying bright red lipstick. “Purse your lips you silly slut, how else are we going make sure you have fuckable lips.” Mistress Chianti chided him. He pursed his lips and as soon as he was finished she thrust the penis gag back in his mouth saying , “There a poster gurl for Sissy Charm School.” He tried to respond but only managed a grunt. “What’s that slut you want more?” Mistress Chianti said as she placed a pink wig on his head. She turned and picked up a riding crop and began flicking the clothes pins off his penis and scrotum. The pain rushed through his groin as the blood returned and he writhed between ecstasy and agony.
She continued to torment him and finally released him saying, “It’s almost Midnight slut and time for you to get some rest, tomorrow is going to be a long day.” “Yes Mistress and thank you.” He responded. “Follow me.” She commanded and headed to the door they had entered. “Yes Mistress.” He replied and walked a little stiffly behind her. They went back to his room and she said, “There’s a Teddy in the armoire for you to wear, wash up and go to bed.” “Yes Mistress.” He replied as he entered the room. She didn’t say anything else as she closed the door and he heard the lock on the door click and realized he was committed now and there was no turning back. He went to the armoire and saw that it had been filled with women’s clothing, shoes, and undergarments. He also saw three wigs and an empty wig stand. Removing the pink wig he placed that on the stand and taking the teddy he made his way to the bathroom and washed off the makeup. He put on the teddy, carefully folded the clothes he had worn placing them in the drawers of the armoire. He turned and fell into bed, the soft ache of his body lulled him off to sleep as his mind wondered what Mistress Chianti had in store for him in the morning.
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