Penny's Worth - Chapter 5 - Sex Stories

Penny's Worth - Chapter 5

... new clothes for several minutes. Finally, she blurted out, “Do I have to do anal?” Without taking my eyes off the road, I replied, “No. You don’t have to do anything you aren’t comfortable with. You can suggest something else, if that’s what a potential client wants. But, it is a popular request.” He face contorted into an Ewww expression. “So you do it?” “Sure. I learned to like it with my husband.” “But it hurts. I didn’t like it at all.” “You have to make sure the man inserts his cock in the right way. It can be very pleasurable.” “Can you teach me?” She was coming around. An eagerness to learn and grow was a good sign. “Come to the penthouse after your first client. I’ll work you over with a dildo so you can get used to it.” Ivory wiggled her ass a bit uncomfortably in the car seat but beamed at the knowledge I was willing to instruct her. You might just make a good partner after all, I thought to myself. ~ ~ ~ The Hand Full “OMG! OMG! You cannot believe the John I just did. It was so fucking hot and weird.” Ivory exuberantly bounced into the room the instant the elevator door opened. “He was the oldest guy I’ve ever done. He must have been at least forty. I got him hard with a BJ, and then he insisted on a sixty nine. I came so hard I squirted his face, and he was so into it.” “Slow down. You’re wearing me out; just hearing you talk about it.” I hoped I wouldn’t get every detail of all her upcoming sexcapades. “No. Here’s the buzz. He keeps asking my age. And I keep ...

... saying I’m nineteen, but I’m not going to show him my ID. I’m not buying booze. He’s just fucking me.” I waved my hand in the air. “The point, please.” “Oh, yeah, right. He said he wanted to see me again. But he wants me to do like this whole naughty school girl routine. You know, pleated plaid skirt, knee socks - the works. And he tipped me two hundred. Can you believe it?” “Sure. Johns request all kinds of things. We don’t judge a man’s interests.” “So, here’s the deal. I could do a cheerleader thing, too. I bet these old guys would eat it up.” “Fine. Just arrange for them to meet in your room. The hotel can’t have a parochial-school tart hanging out in the bar. Just calm down.” “Sorry, I know I’m excited. I just love working here.” She caught her breath. “So, you’re going to ass fuck me, right?” I had a collection of dildos on the table. One with a rubber suction cup in the base was ready for her oral training. It was a full nine inches long, and five in circumference. “Before we start, I want to see you perform fellatio.” “Do what?” “Give it a blowjob.” “Oh, polish the knob.” She inserted it into her mouth as her wavy raven hair cascaded onto the imitation scrotum. She struggled to intake as much as possible. Her mouth was smaller than mine and she began to gag as it pushed farther toward her tonsils. “You’re working too hard.” For the next fifteen minutes I instructed her on the best way to provide oral pleasure, the same techniques Quinn had provided to me. It was as if the ...