Chapter 1
The phone rang.
“Be at Suzette’s Salon, 555 North Main Street, 12:30 sharp. You have an appointment” she said quickly and concisely before she hung up.
It was Mistress Collette. He knew she was planning something for him this weekend, something that she promised would be “memorable”. He wasn’t quite sure what she had planned. She had been giggling to herself, collecting packages and placing them in a secret black tool bag and had forbidden him to look inside. She placed the bag in his car, where she knew he would be tempted to peek, but also knew that he prided himself in being “well-trained” and able to follow specific instruction.
It was only 9:30, so his 12:30 appointment left him plenty of time to dwell on what she had planned for him. He quickly ran to the computer and looked up Suzzette’s Salon on North Main. It appeared to be a normal salon, haircuts, styling, tanning and the like. Not sure what she had him scheduled to have done. She had been having him grow his hair out, it was now shoulder length. So perhaps she had him scheduled for a hair cut or a trim?
He sipped on coffee as he wondered what she could possibly have planned for him this weekend. She had been teasing him for the last two months about this weekend. She was absolutely sparkling when she talked about her planning, was practically giddy every time she got a new plan brown wrapping package delivered to the front porch. All addressed for “M.C.”, Mistress Collette as he was accustomed to calling her.
He googled the address, 15 minutes away, he had better leave at noon in case of any traffic, he knew that Mistress would not be happy if he was late.
12:20PM
He pulled into the small parking lot, it looked deserted. Saw the small sign on the door that said “For scheduled appointments, text on arrival”. He quickly texted the number listed “Hello, Brad here for a 12:30 appointment”
2 minutes passed and a message came back “Your room has been santized and we are ready for your arrival. Please come in and proceed to room #3”.
He pulled open the double glass doors, and walked inside. A young woman sat at the desk, smile at him. “Brad?” she asked.
“Yes, I have a 12:30 appointment.” He replied.
“Yes, we will be in room three just down here”. She said as she led him down a short hallway.
He turned the corner into room number three, still unsure of why he was here. The room was simple, just a white walled room with a simple table, like a massage table in the middle of the room. “Did she schedule me a massage?” Brad was thinking to himself.
He was standing in the doorway with a dumbfounded look on his face when the young lady said “I’m Hanna, I will be doing your wax today. Go ahead and undress from the waist down”. She was reading notes on her computer screen and followed up with “Oh wait, we are doing a brazilian, legs, chest and abdomen. So you might as well just take everything off.”
Was she serious? She was going to rip all the hair off of his body? And she wanted him to undress in front of her?
She stood looking at him as he quickly scanned the room looking for a towel or drap that he would be able to cover up with, expecting that she would excuse herself so that he would have a minute to collect his thoughts, undress and cover up with at least something.
She must have sensed his hesitation. “We don’t leave the room, so go ahead and get undressed, put your stuff there on the chair in the corner” she said as she motioned towards the small chair in the corner of the room.
He looked at her and then the chair. His heart rate jumped a bit as he remembered that he was wearing a pair of pink thong panties that would be embarrassing to have this young lady know he was wearing.
“I can’t do my job unless you undress and lay here on the table.” she quipped as she patted the middle of the table. “I’m going to see it all anyway, don’t be bashful”.
He thought to himself “she is right, she is going to see everything. I might as well just get this over with” as he pulled down his pants, trying to pull the pink panties off with his jeans. Better to let her think he was not wearing any underwear at all then for her to know about his recent obsession with wearing women’s panties.
He got all of his clothes off and laid down on the table in the middle of the room. The fluorescent lights shined down into his eyes. She pulled on a pair of blue latex gloves and said “we start with a light oil that will keep your skin from pulling too much” as she began to rub an oil over his body, chest, belly, groin and legs. She quickly rubbed the oil over everything, somehow she rubbed his genitals quickly with the side and back of her hand in a very clinical, not the least bit sensual way.
“Have you ever been waxed before?” she asked as she took a wooden spatula and started applying wax to his pubic bone area.
“No first time” he replied as she pulled the first strip of wax off, revealing a strip of perfectly bald skin underneath.
“I’ll try to be nice” she quipped as she applied warm wax to his scrotum and quickly pulled.
“Grab the tip and pull up, hold it up” she said as she dipped another wooden spatula into the warm wax.
40 minutes later he laid there completely hairless from the neck down. He realized that he had never felt this naked in his life. She had even had him spread his butt cheeks and waxed his crack. He was naked and also slightly humiliated.
She said “Ok, I’m all done, you can get dressed now” as she turned to grab a Victoria Secret’s shopping bag that was sitting next to her supply table. “But Collette dropped these off for you, she said you are to wear these home.” she giggled as she handed him the bag.
He groaned as he looked inside and saw a matching set of white lacy panties and matching bra. “A bra? She has never made me wear a bra before.” he was thinking as Hanna stood and waited.
“If you get dressed now, we can check you out up front.” she stated as she began to tap her foot in a way to let him know that she was waiting.
She smiled as she watched him fumble with the clasp on the bra, deciding to clasp it in front of him and then spin it around and thread his arms through. It fit well across his chest, but he was obviously lacking in the chest enough to fill out the DD cups. The panties were nice, silky, thongs, his Mistress knew his preferences in panties. She should, she had introduced him to the pleasure, recently making him throw out all of his boxer briefs after a panties shopping spree.
“Ok, ready?” asked Hanna as she walked towards the door, leading Brad down the short hall and back to the reception area.
“First visit discount, your total today is $265. Will that be cash or credit?”
“Ummm, credit” He mumbled as he searched for his card. Knowing that Mistress Colette will ask, he leave a fifty dollar tip and walks back to his car.
As he gets back to his car, he feels his phone vibrate. His pulse again quickens when he sees that it is a message from Mistress Collette. “Meet me at my house as soon as you’re done at Suzette’s.”
A quick “Yes Mistress” reply and he jumped in his car and quickly pulled out of the parking lot, headed to his Mistress and her promised memorable weekend.
Chapter 2
He arrived at her house. It was a small 2 bedroom, 1 bathroom ranch with a white pickett fence and a large oak tree in the front yard. Very normal, typical house for a very untypical woman.
He parked in the drive, jumped out of the car and practically skipped up the drive. Seeing his Mistress always put him in a good mood, even if she had just made him pay to have all of his body hair brutally ripped out.
He rang the doorbell, then quickly dropped to his knees, to kneel in front of the closed door. Eyes lowered, he prayed that none of her neighbors were watching. He was embarrassed to have been seen by the old guy who lives next door last week. He had tried to suggest a different door protocol after that, but Mistress wouldn’t think about it. She said she likes to open the door to see him kneeling, with his eyes focused on the floor, her feet when the door opens. She says it makes her feel like she is letting her dog in. Her dog. She did often refer to him as her “pet”, so dog makes sense.
“Oh, Hello my pet!” Collette says as she opens the door and grabs Brad’s arm “hurry, come in here, we have so much to do!” she tells him as she pulls him to his feet, inside the door, quickly closing and locking the dead bolt behind her.
“Into my bedroom” she commands as she points towards her room.
Brad quickly walks into the bedroom. Turning to face his Mistress, he looks down towards her hands as he speaks “I went to Suzette’s and got my body hair waxed as per your instructions Mistress”.
“Good boy” she says as she strokes his hair, “Did you leave her a nice tip?”
“Yes, fifty dollars Mistress”
“I suppose that is acceptable” Mistress replied. “Now look here pet! I have my little black tool bag! Aren’t you excited to see what I have put in this bag? I call it your Sissy Bag!”
Brad swallowed hard, “Sissy Bag?” he squeaked
“Yes, a Sissy Bag for my little Sissy Boy!” Mistress Collette said in a motherly voice. “You want to see what I got in my bag for my little Sissy?” she asked, knowing that she was going to show him either way. “You sit here on this chair and Mommy will show you” she said with a smile as she rubbed the seat of the chair she had placed in the middle of the room.
She unzipped the bag and looked inside as if she had no idea of what was inside. “Hmmm, let me see here” she said as she reached in and purposefully rummaged in the bag. “This looks like a good place to start!” she said as she pulled out the CB6000s cock cage out of the bag.
This cock cage was not new to Brad, and Mistress had made a big deal about getting the “s” version of the cage. The “s” stood for “short”, and Mistress loved to remind Brad that he was definitely a “grower”, not a “shower” and that he didn’t need anymore than a short cage, she didn’t want him getting hard at all anyway.
She quickly unzip the case the cage came in and handed Brad the retention ring. He knew what to do with it, and knew that any protest wouldn’t help his case, only would ensure that he would stay caged longer than originally planned. He took the ring and quickly placed it around the base of his penis, circling his cock and scrotum. She grabbed the plastic cylinder and slid it over the tip of his penis which was starting to become engorged.
“Ehh, he almost got hard! You’ll have no use for him today Sissy Boy!” she giggled as she slid the lock in place and quickly snapped it shut. She took the key and dropped it into a jewlery case filled with earrings that was sitting on her dresser.
Turning back towards her bag she said “Lets see… whats next?” she rummaged around some more and stopped suddenly. She quickly spun around and said “take off that shirt so that I can see your bra!”
“Yes Mistress” he said as he sheepishly took off the sweatshirt he had on revealing his lacy Victoria secret’s bra with the saggy DD cups.
She stroked his smooth skin and said “Mommy likes” as she slid a hand into his bra, squeezed his left nipple, gently at first, then harder with a twist. It was enough to make him yelp with pain.
“Oh my poor little boy” she said as she slipped a silicone breast form inside his left cup. She grabbed the fake boob as if she was feeling up a real boob and moaned as she did. As she was doing that she slipped another fake breast inside the other cup. Grabbing both breasts, one with each hand, she gently pushed him back and said “Let me look at you!”
She laughed as she looked at Brad standing in front of her, totally naked, even bare of any body hair. Wearing a cock cage that made his cock look really tiny and now sporting an oversized pair of DD breasts inside a nice lacy bra.
She made him put his panites back on, making sure that the thong was secured in his now smooth crack.
She went back to the bag and pulled out a white satin corset. She walked behind him and stretched it around him, hooking the hooks together first in the front, she quickly tightened the laces in the back, making him inhale as she pulled the corset tight. “I want my Sissy to have a nice hourglass shape” she remarked as she double knotted the ties in the back.
Brad could barely breathe, but managed a “Thank you Mistress”.
“But of course!” she replied as she reached back inside the bag. “Now sit” she said as she turned the chair towards the makeup light that she had sitting by her vanity mirror.
Foundation, eyeliner, mascara, blush and lipstick came out of the bag and onto Brad’s face. Mistress shushed him anytime he would begin to protest. She started to call him Brandy the more that he protested, by the time his makeup was done she was calling him Brandy the Sissy Boy.
“Now you are almost a perfect Sissy Slut!” Mistress Collette said excitedly. “What else do I have in this bag?” she asked as she began to rummage again.
She pulled out a large bottle of lube and a large butt plug. As Brad began to shake his head “no”, Mistress sharply slapped him across the face and hissed at him “dont you dare start crying and fuck up my makeup!”
Surprised, he instantly sat up and regained his composure.
“Good boy, now bend over!” she commanded as she stood behind him and roughly pushed his upper back so that he was bent over the chair in front of him. She grabbed the bottle and squeezed a hefty amount of lube onto his puckered asshole.
As she rubbed and twisted the head of the butt plug against his asshole she firmly said “Now relax, it is going in there, this will be soooo much easier if you relax!” as she said relax a second time she pushed the plug deep inside of his ass.
He arched his back with initial pain. Damn, she had plunged that in fast and deep! He knew from previous experience that the initial pain would wear off as the spasm died down, his ass would adjust to the foreign object that had been placed there by his lovely Mistress.
“That will help you to prance around like a little princess bitch!” she exclaimed as she grabbed her phone. “Now prance so that i can get some pictures!” she laughed as she used her phone to begin to snap pictures. “Stick your ass out” and “let me see those tits!” were orders that she barked out as she made Brad, now Brandy pose and dance around for the camera over the next 30 minutes.
“Thats my good Sissy Boy!” she again laughed as she laid down on the bed and pulled her skirt up high enough to reveal that she wasn’t wearing any panites. “Kneel here at the side of the bed” she commanded.
He knelt at the side of the bed. She placed one leg on either shoulder, leaving her wet pussy just inches from his mouth. His mouth began watering, he wanted to taste her, but he knew better than to taste her without permission. She reached down and slowly rubbed her clit, moaning as she slowly circles it with her forefinger. Slowly running two fingers down her wet pussy lips, teasing her vaginal opening with slight penetration. Raising those fingers back to her now throbbing clit. Pushing down on her clit, rubbing it hard, she starts to gasp. As she begins to orgasm, she clamps her thighs down on the sides of his head while reaching down and pulling his head into her groin “Eat!” she commands and she sprays cum into his mouth.
He eagerly laps at her juices. Running his tongue in long slow strokes, from her asshole up to her clit like he knows she likes. Slowly circling her throbbing clit with his tongue, sucking gently as he slips his forefinger and middle finger into her wet cunt. Sucking on her clit harder as he hooks his fingers forward to expertly bump her g-spot. She gasps as she begins to cum hard and as his works her g-spot over with his first and second fingers, he slips his pinky finger up her tight ass. She screams out as she pumps squirt after squirt of clear fluid onto his face and chin.
Makeup totally destroyed, mascara and eyeliner running down his face he smiles up at his Mistress. She surprises him when instead of stroking his hair and telling him how much she loves it when he eats her pussy, she looks down and complains “You ruined your makeup! Now stand up!”
He stands up in front of her as she returns to the bag, what else could she have in that bag?
She pulls out a magic wand vibrator and plugs it in.
“You must leave that cage on for at least today” she said. “But we will see if we can get you the orgasm that you deserve after that pussy eating fest!”
“Maybe you will have your first Sissygasm today!” she said as she clicked the vibrator to high speed.
Brandy looked down at her cock and realized it was straining hard against the walls of the small cock cage that contained it. She saw the purple head throb inside of the clear plastic. Saw the precum dripping profusely from the slit opening at the tip. Precum oozing out.
Mistress Collette began by slowly running the vibrator over the top side of the cage, then underneath, pressing it gently against Brandy’s balls. It felt so good. Brandy let out a moan as Mistress moved the vibrator to rest on the butt plug that was buried deep inside her ass. She pressed harder as Brandy felt contractures pulsing through her ass, then her cock. Mistress took the vibrator and held it against the cage at the head of her cock while she reached down and pressed on the butt plug with her hand. She maintained the vibrator in one spot as she pushed and pulled and pushed the plug again, working it back and forth over her sissy’s prostate.
Brandy gasped as she felt Mistress working the butt plug in and out, the vibration on the cage feeling as if it was going through her cock into her entire body. She began to feel waves of pleasure, warmth swelling up deep from within her prostate. She began to moan and a short gasp as warm thick fluid started to leak out of the tip of her cock. She felt one long continuous orgasm, with a slow drizzle as opposed to the well known pumping, rhythmic orgasms that she is accustomed to having.
As she continued to cum, Mistress Collette scooped up the white creamy spunk on her fingers and rubbed it onto Brandy’s lips, plunging them deep into her mouth.
“Sissies clean up their messes, Sissy Boy!”