Then he turned me over and started sucking my dick. He briefly stopped and said, “I’m going to show you something amazing.” He had me lift my ...nees then lubed his finger and as he sucked my dick, he ran his finger around my anus. I thought this was fantastic. After several minutes I was getting closer and started thrusting up into his mouth. He pulled back and said, “Here it comes.” Then he thrust his lubed finger into my ass and stroked my prostate. Oh my God! I came harder than I ever had. It was hard to believe that it could squirt like a fountain. Contessa pulled me upstairs to her room. As soon as we were in there, she laid on the bed and spread her legs wide and said, "It's time you actually win this contest, Mason." Her pussy opened a little revealing the soft pink plushness where so many men had already been. The wetness began to actually leak out of it. My cock began to throb hard. I knew Contessa could see it pulse wildly. "Mmm, Mason, you are so fucking hard. Plunge it. I pounded away at her pussy as hard as I could, holding onto her hips and as I did she moaned with pleasure; my god she was loud and she was clearly loving my young cock. As I thrashed away I considered when the last time someone had been inside her was-it felt like it must have been recently. Eventually she wriggled free and lay on her back, legs spread wide open. I lay beside her and rubbed her wet pussy with my hand, my cock stood completely upright as hard as it could possibly be. She. 00 or even $20.00 for a few hours work, and answered without thinking."Yes ma'am. I would," I said excitedly. "Good. Come see me next Saturday morning, and we'll talk," she said grasping my hand softly, then retreating inside and closing the door. I didn't even think about the implications of her hiring "Sylvia" at first. The very first thing I thought of was how soft her skin was to the touch, even at her age. And how gentle it was. More like someone wrapping your hand with a big cotton ball.