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Surely I couldn’t be the loser? Dorothea didn’t count, but stroked me, a bit faster than in my previous test, one stroke per word. “You impressed me, boy. I won’t go easy on you, but I want you to win.” She then let go of my penis. I stood there panting, waiting for yet another raging desire to cum to pass. As it finally did, I gasped, “Thank you, Mistress, thank you.” I felt weak, though my cock, now twitching, remained fully erect and my sore balls throbbed. I accepted the water Dorothea offered. “Lie on your back with your knees up, boy,” Dorothea commanded. I was glad it was a clean, shag carpet. I looked up, knowing I’d see way up Dorothea’s skirt if she stood. To my surprise and delight, she straddled me, right over my face. She wasn’t wearing any panties! I saw my first pussy, all wet with some fluid evident on her upper thighs. Her round ass jutted beautifully. She lowered herself, leaning forward to put her arms under my knees. Pressing my thighs against her, she rocked. The topic at hand was obviously Jeff’s savings account downtown. Apparentl his dad had looted his college fund. Apparently there was now no money to finance school.Mom was right Even with the lucrative (for a seventeen-year-old) job he had held as a caddy at a country club with very wealthy members, he would never be able to save enough. Even if he also took back his former restaurant job, which Mathon would give him in a second. It wasn’t as if he had many options. His dad was right, too. With his mediocre grades, he was lucky to have been accepted at any college. It was probably his high scores on IQ (171) and SAT (2100) that got him in. He was a loser. And it seemed he would remain a loser, would not get his chance to break out. He was trained only as busboy, dish washer, cook, and caddy. The money from caddying was very good and could get a lot better with time and luck, but it was strictly seasonal. He could not now break the cycle as easily as he had thought. Now it seemed his.
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