Alex in Wonderland Ch. 10

DISCLAIMER-This 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.

(Alex falls deeper into Sam's web)

Sam was sitting in the lounge of her lofthouse, in her catsuit, when Tam entered having closed the coffee shop. Tam plopped herself down in the armchair.

"How is Alex doing tonight?" She asked.

Sam pushed a button on her mobile phone and the new blind in front of the mirror began to rise to reveal the playroom.

"What have you done to him?" She shouted, holding her hand to her mouth.

Tam looked through the mirror and could Alex's latest predicament at Sam's hands. He was naked, collared, leashed and handcuffed clearly being forced to have sex with another man. He had no idea his cock was inside another man's ass because he was blindfolded, Tam also noticed red marks all over his chest and torso. She turned to Sam.

"You said you weren't going to hurt him, Sam!" She said.

"I haven't hurt him." Sam shrugged. "That's Jennifer's doing. Don't worry. she went easy on him and we both know what a fast learner he is. Now get your mobile out and start recording."

Tam shook her head but did as she was told and began recording Alex's latest humiliation on her mobile. She also noticed that he was covered in oil and the muscle on his body was more clearly defined. She admitted to herself that the scene before her was indeed sexy and felt her pussy getting wet. Suddenly, Jennifer stepped up behind Alex and whipped off his blindfold. As soon as Alex's eyes adjusted to the light she could see the revulsion on his face.

When Alex looked up at the mirror, Sam touched a button on her phone.

"I said you would have the opportunity to fuck a pussy, Pet" She said. "I didn't say it would be a woman's."

On the other side of the mirror Alex instinctively began withdrawing his cock from the man's ass, This brought a rebuke from Jennifer who swatted both of his ass cheeks with the crop. Alex yelped into the dildo gag and jumped forwards, which thrust his cock balls deep back into the ass before him, which drew a gasp from the man.

"Get your cock back in there, boy!" Jennifer hissed. "Now don't move!"

For a few minutes nobody move, all that could be heard was Alex's deep breathing, He took a closer look at the man below him. He was on a kind of medical gurney and was completely shaved of his body hair except for a blonde buzzcut on his head, he was also wearing an identical neck collar like him. Alex could see that he was also covered in oil that shone over his body under the lights. What drew Alex's attention the most were the angry red stripes across his chest and torso, no doubt there were more stripes down his back Alex thought. The man's cock was also fully erect and his mouth gagged. He was also completely immobile, there were leather straps binding his ankles to his thighs. His wrists were then cuffed to the d-rings on the thigh straps. meaning he was at Alex's mercy.

"His name is Nathan, boy." Jennifer whispered in his ear. "He is my pet and as you can see I am very strict with him. Aren't I, Pet?" Jennifer looked down at Nathan, who nodded compliantly. Jennifer looked at the mirror at Sam and nodded.

"Now that you are acquainted with you fellow performer, Pet." Sam said to Alex over the intercom. Jennifer and I have made a wager. To cum tonight you must fuck Nathan and last more than ten minutes, at the end of every minute you will get a ten second break. Your cock however must remain inside Nathan's boy pussy. If you last more than ten minutes I will release you from chastity for two weeks, if you fail there will be a forfeit. Do you understand, Pet?"

Alex groaned, but nodded his understanding, his heart racing at the opportunity of being cage free for two weeks.

"Now begin, Pet." Sam instructed. "Jennifer and I have agreed you can go nice and slow, but you must maintain the agreed pace and you must thrust balls deep every time. There will be consequences if you don't."

Alex nodded and immediately began fucking Nathan at a slow pace that bought a stinging slap on each of his ass cheeks from Jennifer's crop.

"Faster, boy!" Jennifer hissed. "This needs to be a fair contest!"

Alex once again yelled into the dildo gag and began fucking Nathan slightly faster, he also screwed his eyes closed to concentrate and threw his head back. He therefore did not see Jennifer look through the mirror and wink at Sam.

Tam, however, did notice and she turned to Sam.

"I am I missing something?" She asked.

"This has all been planned." Sam said with a smile. "Jennifer knows her role and Nathan has a small part to play as well. Hell last week you were all for it and this week we've got two boys putting on a show for us!"

Tam stared at Sam but still kept her mobile pointed towards the mirror, she had to admit to herself that what she was seeing was indeed making her wet. Two oiled young men in involuntary bondage humiliating themselves in front of three women was indeed sexy. She noticed that Sam looked down at her mobile.

"You may rest for ten seconds, Pet." She told Alex over the intercom.

In the playroom Alex stopped with his cock balls deep in Nathan's ass and closed his eyes taking deep, deep breaths. He desperately wanted to cum, at the same time he was terrified of the forfeit he would have to pay. The tantalising prospect of being cage free for two weeks, however, sent shivers down his spine. He then felt two stings on his ass that made he yelp again.

"Your ten seconds are up, boy!" Jennifer stated. "Get fucking!"

After five minutes, to his amazement, Alex had still not cum. He was on his fifth ten second break when he suddenly felt a tightness engulf his cock inside Nathan's ass. Alex looked down at Nathan in shock and screamed at him through his gag, Nathan was clearly clenching his anal muscles to get Alex to fail. Nathan merely rolled his eyes and groaned but kept clenching his ass.

"What's going on there?" Tam asked, looking over at Sam.

Sam just smile yet again.

"Nathan has been told to start milking Alex's cock with his ass after five minutes." She replied.

"So Alex doesn't have a chance, does he?" Tam asked.

"Nope." Sam replied with a degree of smugness. "I told you I intend to have as much fun as possible with him."

Due to his distraction Alex went over the ten seconds and received two stinging blows to his ass yet again. He now knew this was Sam's intention all along and he had been set up to fail.. There was nothing he could do to stop the inevitable so he continued fucking Nathan slowly and as hard as possible.After seven minutes he felt his orgasm and threw his head back and began to wail into his dildo gag. Jennifer also knew he was about to cum, she reached between his legs from behind and grabbed his balls and pulled him away from Nathan's ass. She held his cock and pointed it in the air.

His cock began to eject large amounts of semen in large ropes. His first two spurts shot well over Nathan's head and landed several feet up on the mirror. The remaining eight spurts landed on Nathan's face, neck, chest, stomach and over his cock and balls. Alex wailed into his dildo gag for a good sixty seconds and stood on tiptoe until his long awaited orgasm diminished. After coming down from his high Alex looked down to see Jennifer firmly grasping his cock.

"Now it's time for the forfeit, boy!" She said with undisguised glee....."

Alex looked down at the sight before him. He had just fucked another man in the ass and shot his load all over his body. Nathan's entire upper torso, from his his face to his cock was covered in Alex's cum, an amount of semen that Alex didn't think he could possibly produce. I' m not homophobic Alex thought to himself and felt some revulsion at what he had just done, but the scene he was looking at had kept him turned on. It must have done, he thought, because his cock was still as hard as a rock, fully engorged with blood and aching for more.

In the lounge, on the other side of the mirror, Sam and Tam had been watching the performance that Alex and Nathan had just provided them. They sat in silence for a few moments until Sam turned to Tam.

"Now, are you going to tell me you're not impressed with that cumshot?" Sam asked.

Tam just shrugged and kept filming with her mobile, for she was impressed, and admitted to herself that what she just witnessed was fairly amazing. She glanced over at Sam as she touched a button on her mobile.

"That was a most impressive cumshot, Pet." Sam declared over the intercom. "But you know you came too early, so you must now take a forfeit and you will leave here tonight caged. Jennifer will decide what form your forfeit will take."

Alex, still breathing heavily, looked over at Jennifer, she was still standing right next to him with her hand firmly gripping his hard cock, She looked at him with disdain.

"If you were my pet you would be suffering greatly for cumming so early." She sneered. She released the leash from his collar that was attached to the ceiling hook.

"On your knees!" She snarled.

Alex did as he was told, which was difficult, with his hands cuffed behind his back and his feet spread. He winced as he jarred his knees on the platform floor. Jennifer helped Nathan to his knees on the wheeled gurney, she then positioned him so that his erect cock was hanging over the edge. Alex was now having serious misgivings abut what his forfeit was going to be but remained silent. Jennifer moved behind him and swatted his ass cheeks with the crop.

"Move to your left, boy!" She instructed. Alex shuffled as instructed and noticed that he was now at right angles to the viewing mirror.

"Now then, boy!" Jennifer said. "I promised my pet an orgasm if he helped get you off and he has earned his reward."

Alex looked out of the mirror and saw that Sam was watching with an expressionless look on her face.

"You came to early, Pet." She said." Now you must pay the price. If you don't give Nathan his reward I will have to give Jennifer control of you for two weeks. That was also part of our wager. Decide.."

Alex was momentarily at a loss. While he certainly didn't want to be under Jennifer's control for any longer than necessary, the idea of sucking another man's cock was abhorrent to him. Jennifer approached behind him and unbuckled the dildo gag, she then swatted his ass cheeks again.

"Decide, boy!" She snarled.

Alex leaned forward and shyly opened his mouth. He had never sucked a man's cock before and it showed. Jennifer stood close to his ear to instruct him.

"Concentrate on the head first, boy." She said. "You have had plenty of practise on the dildo, so get to it!"

Alex had seen plenty of porn movies of girls sucking cocks and tried to copy them. Aware that he was being recorded, he put his mouth around Nathan's cockhead as instructed and began sucking. His hollowing cheeks were proof of this as well as Nathan's groans of approval. He then moved back slightly and used his tongue to flick back and forth across his cockhead slit. Then he began using his tongue to cover his entire shaft with his saliva and again moved back and forth, using his mouth to masturbate him. He would then suck on Nathan's balls, determined to put on a good show for the women watching because he now knew what was expected of him.

"I told you he was a quick learner." Sam said to Tam, clearly enjoying the show. "I also think he is beginning to enjoy himself."

"Do you think he realises that you are making him, in effect, a porn star to make money?" Tam asked.

"A girl has to make a living." Sam shrugged.

Tan, as usual, conceded the point and remained silent as they continued to watch Alex give his first ever blowjob.

Alex was deepthroating Nathan's cock and deliberately gagging himself with, what he hoped, was obvious enthusiasm. He was also moaning himself as he continued to coat Nathan's cock with his saliva.

So it went on for several minutes, the head, balls and shaft until Nathan started to breathe heavily in between groans. It was clear that Nathan was about to cum. Jennifer, who was feeling somewhat redundant due to Alex's enthusiasm, now stepped forward and grabbed Alex by his hair.

"Open your mouth, boy!" She hissed in his ear.

Alex was now kneeling a few centimetres away from Nathan's cock as he started to cum. Nathan's semen ended up in his hair, on his face, in his open mouth and down his neck with some dribbling down onto his chest.

Throughout it all Alex's cock remained fully erect, what now he thought.....?