Alex in Wonderland Ch. 10 by Entreri1791,Entreri1791

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.

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