Alex in Wonderland Ch. 08

DISCLAIMER-This is a series of fan fiction, most of the characters in this series follow on from ONLINE CHASTITY by FICT which can be found in the BDSM part of Literotica. This is just my view of what paths the original characters from the original series could have taken. You should read Online Chastity chapters 1-6 to see how Alex ended up here.

(Alex is falling deeper under Sam's control)

Alex was beginning to get frustrated, it was now Wednesday, and he couldn't remember the last time he had gone so long without an orgasm. He was also beginning to wake up with large pools of precum leaking from his cock, staining his bedsheets and began to suspect Sam was tormenting his balls while he was sleeping. Despite this torment of being caged in chastity he was still trying to go about his normal routine however and, despite some knowing glances and lewd comments, he was not covering the shock collar around his neck. He was also trying to come to terms with the fact that Sam was either watching him from afar or w s employing someone to keep him under surveillance. He was now beginning to feel that Sam's control over him was getting out of hand.

He did however feel in control inside his own apartment and felt safe enough to wear high necked shirts while taking part in Zoom meetings with clients regarding his job as a graphic designer. During one such meeting there was a knock at the door which turned out to be a Fedex parcel. Alex was very curious about the contents because he was not due to have anything delivered. Once the final Zoom meeting of the day was over Alex got a knife from the kitchen and opened the parcel.

The contents of the parcel made his heart skip a beat as well as causing his cock to twinge in its confinement. Inside were about twenty women's panties of various colours, there were also lots of stockings and garters. There was an envelope with a letter inside it that Alex opened and began to read with some trepidation.

'Pet I haven't forgotten how excited your cock became when I asked it about throwing out your underwear and replacing them with women's panties. I have added a few extras just to keep things interesting. From tomorrow you will wear women's panties, stockings and garters at home and panties when you go out. To ensure you obey I will send text messages and you will get a small amount of time to send me a photo. These instructions will be sent at random times so I suggest you keep your phone charged and close. If you fail to meet the time limit I give you in the message your balls will deeply regret it. This also applies to the high necked shirts you are probably wearing for your Zoom meetings with your friends and clients. As for tonight Pet I want you to use your photography skills and equipment to send me lots of photos of yourself testing out your new underwear. Make the images sexy and do not cover your face. Sam'

Alex was once again speechless, his brain was feeling utter despair but his cock was straining with all its might against the cage that trapped it, it was also leaking precum in strands that were soaking his boxer shorts. It seemed to Alex that Sam could read his every move and just when he thought he retained some control she crushed him in the blink of an eye. He began sorting through the box and noticed that some of the panties were silky with garish lace and some were rather nondescript. The stockings were mainly black sexy looking numbers as were the garters. With a reluctant sigh he got up to fetch his photography stuff and do as he was told.

He decided to set up his cameras in the lounge at first, then intended to move to his bedroom later in order to create some variety in the hope that Sam would be impressed with his photography skills. He also scoured the internet for magazine shoots on order to get some inspiration from the female models and their poses. For the next hour Alex was taking photos of himself, the cameras were on tripods and taking shots at automatic intervals, so he was able to strike provocative and hopefully sexy poses that would make Sam impressed with his efforts. All the while his cock was as hard as it could get in the cage and leaking precum almost non-stop, his brain however was thinking this was a terrible idea.

It was now Friday morning and, true to her word, Sam had sent him several messages demanding photos to check he was following her instructions. The length of time he was given to text back varied from 10 to 20 seconds, on one occasion, when he was out running, he was given 30 seconds. Sam obviously knew via the tracker in his neck collar that he was in the park and would be forced to dive into some bushes to send the photo in order to not get arrested. He was also very careful with his Zoom meetings because the stockings and garters, along with the panties he was forced to wear, could not be seen by his clients. He could not risk putting trousers on while at home in case he struggled to get out of them in time for Sam's photo demands and got his balls shocked, something that terrified him.

At 2 pm Friday afternoon his phone beeped, alerting him to a new message, he jumped to pick it up and saw another message from Sam.

'Pet be at the coffee shop at 5 pm make sure you are wearing panties, Sam'

Alex breathed a deep sigh of relief, for the past two days he was on tenterhooks, Sam had such control over him that he was becoming terrified of what she might do next. Although this was something he had initially wanted the reality was still sinking in, yet his cock was constantly straining to escape the cage and continually soaked his panties with precum.

He entered the coffee shop at exactly 5 pm and saw Tam behind the counter, she gave him smile and pointed to two large coffees on the top of the counter and gestured with her head that he should go straight upstairs. Alex blushed and did as instructed. The door to the lofthouse was open.

Alex stepped through the open door and saw Sam standing by her sofa in her catsuit staring intently at him. He gulped and stood completely still as though transfixed, like a rabbit caught in a car's headlights.

"Hello, Pet." She said. "How has your week been?" She asked.

"Fine, Miss Sam." Alex replied, blushing deeply and looking at the floor.

She walked towards him and he felt she looked like a panther stalking its prey. As she got closer she put her hand into the pocket of her catsuit and produced a small key. It was the key to the collar and cock cage.

"It's yours if you want to end this, Pet." She said.

Alex merely smiled.

"Shall I place my clothes in the duffle bag, Miss Sam?" He asked.

Sam gestured to the duffle and Alex began removing his clothes including his panties without further comment. Apart from his collar and cage he was naked before her once again. Sam reached into one of the drawers of the coffee table and tossed a pair of handcuffs at him.

"Put those on, Pet." She said. "Behind your back."

Alex did as instructed and waited as she hooked the duffle to the same carabiner and watched as it went up into the rafters. Sam walked towards him with the key and swiftly removed the cage that had imprisoned his cock for a week. His cock immediately swelled to a full erection, finally free from its captivity as Sam also removed the ring behind his cock and balls, she placed them on the coffee table.

"Tell me the truth, Pet." She said while slowly stroking his cock with one hand an fondling his hairless balls with the other. "How has your week been?" She asked again.

"D-d-d-d-difficult, Miss Sam!" He gasped. "A-a-a-a-also f-f-f-f-fun, Miss Sam!" He admitted.

"I must say, Pet." She cooed. "The photos you sent of yourself were very good and very tasteful."

Alex realised that she was impressed with his photography skills and he felt pleased by her praise. Sam's hand was soon covered in his precum, so she held it up to his mouth. He opened up immediately and began to suck her fingers clean.

"You must be very eager to cum, Pet." She smirked.

"Yes, Miss Sam." Alex replied, his chest rapidly heaving with deep breaths.

"Well let's get started." She said.

She attached the leash to the d-ring of his collar and led him to the playroom. As they passed he noticed that there was now a blind on the wall of the lounge, covering the mirror that looked into the room where he was humiliated seven days ago.

"I've made a few changes since last week, Pet." She said when she saw him staring.

On entering the playroom Alex noticed that the lighting was different, the raised platform was now decked in bright light from overhead spotlights. The corners of the room were now in dark shadow. He also noticed that there was a large plastic tarpaulin covering the floor and the silicone pussy he fucked was now missing.

They stepped onto the platform and Sam unlocked Alex's handcuffs.

"Raise your hands, Pet." She instructed.

Alex did so and looked up to see two cuffs attached to the ceiling about three feet apart. His hands were now cuffed above his head. She then disappeared to one of the dark corners and returned with a metal bar two feet in length with ankle cuffs at each end. She had him spread his feet so that he was now spread eagled on the platform in front of the reversible mirror.

Sam stood in front of him and gently stroked his face and cock.

"Ready, Pet?" She asked.

"Yes, Miss Sam." He replied with a gulp.

She stepped back smiling and Alex jumped when he felt a hand rest on his hip and another stroked his ass.

"Hello, Alex." A woman's voice said. "I'm pleased to meet you."

Alex turned his head and saw a woman he did not know dressed in black. She was wearing a black corset with matching stockings and suspenders and thigh high stiletto boots. Her hair was also black with a long ponytail dropping down her back between her shoulder blades.

"This is my friend, Pet." Sa m said. "Her name is Jennifer and she is going to look after you for a while."

"H-h-h-h-hello, Miss Jennifer." Alex stuttered. "H-h-h-how are you t-t-t-today?"

"He is so polite!" She laughed as she looked at Sam. "Where did you find him?"

"He found me." Sam replied.

"If you please Miss Jennifer tonight, Pet." She said. "She might let you fuck a real pussy. Would you like that?"

"Yes please, Miss Sam." He replied. "I would like that very much, Miss Sam."

Sam nodded and left the room.

Alex was now at the mercy of another woman he had just met..........