Alex in Wonderland Ch. 03

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 in the original series could have taken. You should read Online Chastity chapters 1-6 to see how Alex ended up here.

(The ongoing story of sweet Alex falling for the wrong woman online and paying the price. Or is he?)

"I think that's enough for a first session, Sam." Tam said, with an expression of concern.

"You really think so?" Sam replied. She looked at what was now a mirror, knowing perfectly well that Alex was watching them intently from the darkness. "I bet he is standing there with a semi right now waiting to go again!" She claimed.

"But you told me you were going to go easy on him at first." Tam said. "You also told me yourself when you first messaged him that he was perhaps too sweet, didn't you?"

This last statement made Sam think that Tam was right and it was probably best to take things slow. Besides she already knew that Alex was way out of his depth in the world of kinky fantasies. Listing your fantasies on a website was totally different to living them out in the real world. Hell he thought that she had no idea what a Cellmate 2 chastity device was. She played dumb about it and Alex fell for is so innocently and completely.

"Maybe you're right Tam." She admitted. She looked at the mirror again and remembered that is so easy to entice Alex into giving up control of his cock. If she reeled him in so easily once surely she could do it again if necessary?

"Okay." Sam said. "You win, lets get him out of there and get him ready for the next phase. You will stay and help won't you?" She asked.

"Of course!" Tam replied. " I intend to enjoy this as much as you!"

On the other side of the mirror Alex was watching the two women, completely oblivious at how he had been set up. He didn't know it, but as soon as Sam received his message on Fetlife, she had hatched this plan With Tam to draw him in.

Alex saw Sam get up and begin to make her way towards the room he was leashed. He also saw that Tam had plopped down on the luxurious sofa. She immediately started looking at her phone, probably playing back the video she had taken of his humiliation.

Sam entered the room and walked up to the platform where Alex was standing. She noticed that his breathing was returning to normal after his exertions and his whole body was covered in sheen of sweat. She began stroking his back and shoulders tenderly causing him to tense up.

"Don't worry, Pet." She said in a soothing voice. "You have done as well as can be expected for your first session."

She ran her hands down his sweaty back and cupped his ass cheeks before moving around in front of him to caress his chest and tweak his nipples. Sam immediately noticed that Alex was indeed sporting a semi-erection.

"I knew it!" She giggled to herself. "Pet, we are going into the lounge now. Would you like that?" She asked and began fondling his balls with one hand and stroking his cock with the other.

Alex began breathing heavily again and began moaning behind the gag still in his mouth, but managed to nod, knowing he had no choice in the matter. Within seconds his cock was fully erect once again and he began quivering.

She smiled knowingly. "Still feeling horny are we, Pet?" She asked.

Alex nodded vigorously and could not stop himself from thrusting his cock forwards into her hand. Sam began laughing at Alex's desperation. At the the same time she was impressed by his stamina, having already cum twice he was clearly eager to go again as she well knew.

"Now now, Pet." Sam said. "You have to earn your release."

With that she stopped stroking his cock and began to squeeze his balls until he began to wince in pain.

"Now I know you don't like pain." She said. "But that is what you will get if you fail to obey. Understand?" She asked.

Alex once again whimpered but nodded his understanding.

"Good boy." Sam said as she stroked his face and released his balls from her firm grip.

"Now, as you have been mostly good tonight I'm going to make you a little bit more comfortable." Sam declared.

She produced a small key from the pocket of her catsuit and unlocked the high-heeled shoes that were attached to Alex's feet. He let out a sigh as he placed both feet to the ground and wondered to himself how women managed to wear shoes like that for hours at a time. Sam then unstrapped the inflatable gag from his head and removed it from his mouth, it was saturated in his drool. She produced a cloth from her other pocket and gently wiped the drool from his chin and chest. She then released the leash from the hook in the ceiling and pulled Alex towards the door that led to the lounge.

"One last thing, Pet." She said. She turned around and produced the blindfold that Alex had worn earlier and placed it over his eyes. She then gave Alex's cock several strokes to ensure he was fully erect and breathing heavily again. She then whispered in his ear.

"From now on, Pet it's Miss Sam or Miss Tam." She then ran one fingernail across his cockhead. "Understood?" She asked.

Alex jumped, gasped and squealed on tiptoes.

"Yes, Miss Sam! Yes, Miss Sam! Oh my God, yes Miss Sam!"

"You should be aware, Pet." She whispered. " I know exactly where to torture a boy that would drive him insane." She then ran her fingernail across his cockhead again, the skin was as tight as a drum. "Do you believe me, Pet?" he asked.

" I believe you, Miss Sam!" He squealed again on tiptoes. "I believe you, I believe you, I believe you, Miss Sam! OHHHHHHHHHH!!" He arched his back, but there was no escape from the exquisite torture Sam inflicted on him.

"Good boy, Pet." She cooed. This is going to be easy she thought to herself and led Alex into the lounge while he was still whimpering.

Before Tam could look up, Sam explained. "Tam! Before Alex goes home he wants to put on another show for us!"

Tam looked up in surprise and threw her arms up in the air...