Chapter 5
by
bobjohnson12
Did Jake win the bet?
No, and he’s still a virgin
As soon as the timer started Emma got to work. She violently grabbed his erection and spat all over it. She jerked him hard, grasping his dick in a **** grip as if she was holding onto it for dear life. She used her other hand to gently caress his balls.
Jake didn’t expect this. In fact, he knew he was going to lose the bet, but he figured getting laid was worth it. He never figured she would start with just a handjob. Jake started to sit up and wriggle free from his sister.
Emma squeezed his balls and gave his dick a flick with her finger. “Don’t you dare move” she said. She spat on her hand for more lube and went back to furiously beating his dick off.
Jake knew he was doomed. He could feel an orgasm arriving, but he tried his best to stave it off.
Emma also knew that Jake was close. She was a professional after all. She gently left go of his balls with her left hand and quickly shoved her pinky finger up Jake’s ass. The new sensations were way too much for Jake. He moaned in defeat.
Emma could tell Jake was past the point of no return. She aimed his cock back towards him just as the ropes started flying. The powerful orgasm first hit his chest, then the second rope splashed against his cheek. The last few shots pooled on his stomach.
Emma reached for Jake’s phone and stopped the timer. She showed Jake the result. “58 seconds. That’s just sad.” She said. Jake was still coming down from his orgasm to really wrap his mind around what just happened.
Emma traced her index finger along the semen trail across Jake’s chest. She stared at her finger for a second, before quickly shoving it in Jake’s mouth. This brought Jake back to normal and off of his recent high. “Get dressed loser, it’s time to go home so you can pay me.”
What happens next?
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The Price is Right
Sometimes, you get what you pay for
Sick of still being a virgin, Jake spends his hard earned money on a hotel room and an escort. Possibly with unintended consequences.
Updated on May 31, 2026
by darkmagi2
Created on Mar 10, 2026
by bobjohnson12
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