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 jut 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.

(Alex has returned to Sam’s lofthouse.)

Alex was now in the playroom of Sam’s lofthouse on the raised platform bathed in light. He was standing spread eagled in front of the mirror with his hands cuffed to the ceiling with a spreader bar on his ankles keeping his feet apart. Having not cum for seven days his cock was fully erect and looked as though it had no intention of going soft anytime soon. Sam had left him in the hands of her friend Jennifer who was standing right in front of him, she seemed to be examining his body from head to toe. She was dressed all in black with thigh high stiletto boots and Alex could see that she was someone not to be trifled with.

“Hmmmmm.” She said as she ran her fingernails across his chest and stomach. “Such a nice, pristine boy.” She purred.

“T-t-t-thank you very much, Miss Jennifer!” Alex gasped.

Without saying a word Jennifer disappeared into the shadows, Alex heard her stiletto boots clicking on the floor as she returned behind him. He then felt two stinging blows, one to each Ass cheek, causing him to scream in pain.

“I did not ask you to speak, boy!” She hissed in his ear and stepped in front of him holding, what he knew, was a leather spanking crop.

“You will find me very different from Sam and you only nod your head. Understand?” She hissed.

Alex nodded his head emphatically and looked at her in terror. This is not I agreed to with Sam, he thought to himself. But what could he do? Once again he had submitted himself to Sam’s control only for her to pass that control to someone else.

“Very good.” Jennifer said, then she slapped both of his nipples with the crop, causing Alex to wince in pain. This time he did not utter a sound although he began breathing heavily yet again. He looked down at his nipples and saw that two red marks were already beginning to show on and around them.

Jennifer then moved into the shadows again and stepped behind him and placed a blindfold over his eyes.

“It’s probably best you don’t see what is about to happen, boy!” She hissed.

Alex gulped and felt that his cock was beginning to soften. He made it quite clear to Sam that he was not into pain, she knew this when she ‘interrogated’ his cock a week ago, he found it a big turn off. He then felt Jennifer groping his hairless balls with one hand.

“What’s this?” She asked. “You don’t find me and my actions Horny?”

With that he felt more stings to his nipples and a third to his belly button. He began to whimper and shake his head frantically and to his relief his cock began to harden again, mainly due to having his balls tickled. When his cock became fully erect again he felt a sting to its head, Jennifer had slapped him there, he clamped his mouth closed and groaned deeply. He also pulled at the cuffs attached to the ceiling with all of his strength but only succeeded in briefly pulling his feet of the ground.

“Open your mouth, boy.” Jennifer demanded.

Alex felt her slip a gag into his mouth which he examined with his tongue and knew straight away that it was a dildo gag. He also noticed that it was covered in a syrupy substance that had a bitter taste to it.

“The dildo is coated in syrup to stop your throat drying out, boy.” Jennifer barked. “So suck! I want to see those pretty cheeks of yours working overtime!”

Alex obeyed immediately and began sucking and licking the dildo gag and swallowed the syrup.

“You are a fast learner, boy.” Jennifer admitted. “I’ll be back shortly, so you just keep sucking.” With that Jennifer left the room.

Jennifer entered Sam’s control room and found her watching Alex on the several monitors that were fed via the several cameras in the playroom.

“The erectile dysfunction drug you soaked the gag in will take about five minutes.” Jennifer said. “That should keep him fully erect for four hours despite what we are going to do to him.”

“Just make sure you don’t go too far.” Sam replied, looking up at her. “I don’t want to drive him away, he shows so much promise.”

Jennifer looked at one of the monitors and noticed that Alex had stopped sucking the dildo in his mouth. She reached forward and pushed a button on the computer keyboard on Sam’s desk.

“Keep sucking, boy!” She shouted into the microphone.

She smiled at Sam when Alex began sucking the dildo deeply again.

“Don’t worry.” She said, looking down at Sam. “I’ll do just enough to make him terrified of me so that he takes to you a lot more!”

Jennifer re-entered the playroom, her heels clicking on the floor, and ran her hands down Alex’s back and cupping his Ass cheeks. He was now covered in a sheen of sweat and jumped under her caresses, she also ran her fingernails across the welts on his Ass causing him to gasp in pain. His cock was painfully erect and he couldn’t understand why.

“Well, boy.” Jennifer whispered in his ear. “It would seem that your cock is finally excited about pain!”

Alex began breathing heavily through his nostrils, shaking with fear.

Thirty minutes later Alex was a quivering mess. Jennifer had used the spanking crop to torment most of his body with stings and slaps. His upper torso was a mass of red welts where he felt the crop’s touch, she even slapped his cock several times, which remained consistently hard during his ordeal. Tears were running down his face and he was wracked by several sobs, what he didn’t know was that Jennifer had gone easy on him and had not broken the skin in any way.

Jennifer had left the room and left Alex alone with his thoughts. Although he was shaking with pain he still couldn’t understand why his cock was rock hard. After about five minutes he heard footsteps on the floor and instinctively flinched, expecting more pain.

“Don’t fear, Pet.” Sam said in his ear. “For the rest of the evening you will experience pleasure, if you do as you’re told. Would you like that?”

Between gasps and sobs Alex nodded.

“You’ve been such a brave boy tonight, Pet.” She cooed. “You’ve earned it.”

Alex then felt a cool liquid being squirted over his shoulders that began to run down his chest and back.

“This is coconut oil, Pet.” Sam said. “With a little bit extra, it will help soothe your skin.”

Sam began to rub the oil into Alex’s body from his wrists all the way down to his feet. The oil made his skin sensitive to the touch and the nerve endings all over his body were turned fully on. Alex felt Sam’s hands roaming all over his body to rub the oil in, even into the recess of his Ass crack and anus. She gave his balls a generous coating of oil but did not touch his cock, which was drooling long strands of precum down to the floor. She looked at Alex’s body that was now covered with a glistening sheen, that was given greater emphasis under the lights. His thin, athletic body’s muscles could be seen in greater definition than before and she thought he looked very very sexy.

“See you soon, Pet,” She whispered in his ear as she ran her fingernails across his chest. Alex gasped behind the dildo gag still in his mouth and was once again left alone, blindfolded and stretched spread eagled in his bonds.

“Give it five minutes, then we’ll start.” Sam said to Jennifer as she entered the control room.

Jennifer nodded her agreement and they both watched Alex in silence, as he continued breathing heavily, on the monitor screens. They could clearly see his rampant cock erect and drooling.

Alex was breathing softly in the playroom with his chin resting on his chest when he heard someone enter the room. He tensed up as the footsteps got closer.

“Did you miss me, boy?” Jennifer hissed in his ear.

Alex obediently nodded his head, even though it wasn’t true, but thought it best to go along. Jennifer attached a leash to the d-ring of his collar and hooked to the ceiling hook, she then released his arms from the cuffs above his head. She immediately cuffed his hands behind him. Alex was now in the same position as the previous week, only this time his feet were kept apart by the spreader bar. He then heard her moving something in front of him, then she coated his cock with lots of lube and began gently stroking it even though he was rock hard.

Jennifer then grasped his cock firmly and began rubbing his cockhead up and down against what Alex felt was someone else’s body. He felt elated that he was finally going to get to fuck someone’s Pussy as Sam had promised him earlier. Jennifer positioned his cock and hissed in his ear.

“Now push your cock all the way in, boy. Very slowly, understood?” She said.

Alex nodded and, as instructed, slowly began inching his cock forward. He began to gasp as he felt the warm inner folds of someone else’s body for the first time in weeks. He also heard gasps coming from the person in front of him and began to hope he was finally fucking Sam. He stopped pushing when he felt his balls touch the Ass of the body below him.

“Now don’t move, boy.” Jennifer hissed once again. “Understood?”

Alex whimpered, desperate to finally cum, nodded his head.

After a few minutes Alex felt the blindfold whipped away from his eyes, the bright overhead lights forced him to keep his eyes half closed in order to adjust. When the pain receded he looked down and felt a sense of revulsion. Alex saw that his cock was balls deep in another man’s Ass!

He looked up at the mirror and saw Sam and Tam watching from the same two chairs as last week.

“I said you would have the opportunity to fuck a Pussy, Pet.” Sam said. “I didn’t say it would be a women’s…..”