Desperate Measures: The Driver

"Oh fuck! Fuck! Fuck! Fuck! Oh, it hurts. Stop! I can't do it. Stop! Please!"

"Relax, Mr. Lowery, it's almost all the way in. You're doing well. You can do it. I believe in you."

"Slow down! Slower! Please! Oh god, that shit hurts!"

"We're almost there. Almost. Just a little more."

"Ohhhhhhhh! Unhhhhh!" A tear streamed down Tom's cheek.

"It's in. I'll wait a minute so that you can become more comfortable with the feeling."

"Unhhhhh!" More water leaked out of Tom's eyes. He looked up at the counter, and saw that thirteen minutes remained.

"Have you ever sodomized a woman before, Mr. Lowery?"

"Yes," Tom whimpered.

"Did you enjoy it?"

"Yes–very much."

"Did she enjoy it?"

"I...think so."

"Did she enjoy it as much as you did?"

"I think...she did," he moaned. "I mean...probably...maybe...I... don't...know."

"You didn't bother to find out, did you?"

"I guess...not."

"I'm not doing this to punish you. I'm testing your limits. I'm testing your devotion. Are you devoted to me, Mr. Lowery?"

"Yes," Tom whispered.

"Good. Hearing that makes me feel better. Now prove it."

Gwendolyn drew her hips back, pulling several inches of her vinyl cock out of Tom's asshole.

"Oooooo shit!"

"Relax, Mr. Lowery. Just relax and enjoy it."

Tom looked up at the monitor: Eleven minutes remained.

Gwendolyn pushed her cock back into Tom's ass, burying all eight inches in his bowels. As soon as her harness grazed Tom's butt cheeks, she pulled back until only two inches remained. Tom's moans filled the room.

"Would it help, Mr. Lowery, if Ms. Webber came in to give you hand?"

"Yes," Tom panted. "Please."

Gwendolyn reached for the phone and pushed a key.

"Ms. Webber? Your assistance is required."

The door opened and Cynthia entered the room.

"Mr. Lowery is struggling. Please give him some assistance."

Cynthia gave Tom a sympathetic look, kicked off her shoes, and disappeared under the desk. She wrapped a hand around Tom's cock and started stroking. Tom looked up at the monitor: Nine minutes to go.

Gwendolyn increased her pace. She rocked her hips back and forth, sawing the vinyl cock in and out of Tom's ass. She varied the depth of her thrusts, pushing it all the way in for a several seconds and then followed with only the tip. She picked up the tube and squeezed more lube onto the shaft, then resumed her full-length thrusts.

Sitting on the floor beneath the desk, Gwendolyn stroked Tom's cock with one hand and squeezed his balls with the other. His cock responded almost immediately. Within seconds his shaft was swollen and fully erect.

Cynthia's firm strokes on his cock and gentle squeezing of his balls distracted Tom from the pain in his ass. The burning diminished in magnitude from inferno to minor discomfort. With considerable effort he managed to block out the firm presence sliding in and out of his anus, and concentrated on the soft hands manipulating his groin.

Cynthia's expert hands coaxed Tom's erection to a full tingle. The tingling spread from his cock to his balls and sphincter, and then throughout his entire body. The presence in his ass was no longer painful. Pain gave way to desire. Tom started feeling that he could cum again. He looked up at the timer: Five minutes remaining.

"Fuck me. Make me cum. Fuck me."

Tom rocked his hips against the desk. He tried to concentrate on Cynthia's soft hand stroking his cock, but the sense of urgency produced by the vinyl shaft in his ass overwhelmed even that feeling. He felt electricity tingling over every inch of his skin. He had cum countless times in the past, but never before had an impending orgasm consumed his entire body. He felt as though he were about to be run over by a train, and there was nothing he could do to get out of the way.

"One more minute, Mr. Lowery." Gwendolyn's voice originated from somewhere over his shoulder. "You're doing well."

Tom no longer cared about the time. He was waiting on the train that he knew would crumple his body. He wanted to cum.

"Harder! Fuck me harder! Make me cum! Make me cum!"

Tom thrust his ass back and forth against Gwendolyn's vinyl shaft. Cynthia sensed his urgency, and paused to lick the head of his cock. She felt it twitch in her hand, and then resumed stroking with increased velocity. Her hand was a blur on Tom's shaft as she stroked his cock back and forth from beneath the desk.

Tom felt his body shake. His legs stiffened and his ass cheeks contracted. He felt his balls tighten, and then an explosion of semen erupted from his cock, splashing all over Cynthia's face.

She tried to duck out of the way, but the ensuing spurts caught her hair and ear.

"Unh! Ahhhhhh! Unh! That's...unh! I'm...unh! Cumming! Unh!

Tom's legs crumpled. He collapsed on the desk as the vinyl cock slid out of his ass.

"Congratulations, Mr. Lowery, you passed the test. Welcome to your new home."

Cynthia crawled out from under the desk. Tom's semen glazed the side of her face. She leaned over and gave Tom a kiss on the cheek. Tom didn't stir.

"You did well," Cynthia said, patting his butt cheek. "I'm happy for you. You're going to love it here."

"Thank you," Tom gasped. "Thank you. When do I start?"

"You can start right now," Gwendolyn answered. "Get yourself cleaned up and join us for dinner. Tomorrow, you can take Wilson and Max–the pool boy–and start moving your things over. I'll have my attorney settle up with your landlord, and then you can drive me to the office on Thursday."

"I'll show you to your room," Cynthia added. "You can wash my hair for me, since it's coated in your semen."

"Go easy with him," Gwendolyn chided. "He's taking care of me tomorrow night. I want him at full strength."

"I won't be as hard on him as you were."

"You better not be. Don't forget who pays the salaries around here."

I want to give special thanks to my beta reader, Etaski, whose ideas and suggestions were of tremendous assistance.