Getting a blow job on the highway had almost caused me to lose control of the car. Mrs. Green – Joanne - had me so hot that when I came in her mouth, I stupidly took my hands off the steering wheel for just a split second as I forced her to swallow every drop by grabbing her head and holding it in place. Fortunately, as the car started to swerve out of control I had enough time to steer it back into my lane before the truck to my left smashed into us. "Wow that was close! " I thought. "Wouldn't that have made a great headline – Woman Causes Car Crash While Giving Head To Teenage Lover?"
The rest of the trip back to my house was (forgive the pun) anti-climatic.
We stopped around the corner from my house and kissed good-bye. My hand pressed against Mrs. Green's ( Joanne's ) tits and tweaked the nipples as I jumped out of the car. "Call me!" I ordered.
"Oh I will, Lover!" and with a wink and that mischievous smile she drove away. I stood there wondering how I had been so lucky to nail such a gorgeous woman but, at the same time, was plotting my next move. I'd have to keep away from Bobby and my mother mustn't know but with some guile we could do it even if it meant sneaking around. That, in itself, was strangely arousing.
The next day when the phone rang, I hurried to answer it, knowing it had to be her and I was right. "I don't understand the control you have over me. You're a handsome young stud and I'm an old broad but if you're interested I'm sitting in my car fingering myself thinking about you lover, "she offered breathlessly. "Can you get away?"
I had stayed home from school hoping she would call. "What are you wearing?" I asked.
"Just a simple t-shirt and jeans, " she responded.
Here was my chance to test Mrs. Green and fulfill a fantasy of mine. I had always wanted to have sex with a hooker but had never had the nerve to try to pick one up. I was just too shy and gutless. " Go home and change. Put on the shortest, tightest skirt you have along with a tank top but no bra and no panties. Wear your stiletto pumps but you must wear dark stockings and a garter belt. Do you have a garter belt?"
" What have you got in mind baby? Sounds dirty! I'm getting wetter just thinking about it. I haven't worn one of those in years but I can stop and pick up a couple of things at Lynda's Love and Lace erotic store on my way. Be around the corner in half an hour and I'll pick you up. "
"No, meet me down at the corner of Jarvis and Dundas, "I countered. "Park your car and I'll pick you up. "
"But Dennis that's Hooker's Alley!"
"Exactly, we're going to do a little role playing. Unless you're reneging on 'any time, any place, any how'. You're not are you, Mrs…ah…Joanne?" I knew I had her. She figured out what I was after and decided to play along.
When I got to Prostitute's Alley there were only a couple of girls working as it was early afternoon. This area would be crawling with hookers, prospective johns, pimps and cops after dark tonight. Then I spotted her. She looked like a real hooker. She had obviously taken the role seriously. She had on black net stockings, a red micro-mini skirt that just barely covered her ass, a bare midruff, and a red tank top that hardly concealed her breasts. Instead of her high heels she was wearing these high heeled black leather boots that went all the way up to her mid-thigh. Wow! They were better than her come-fuck-me pumps! The makeup was plastered on and her pouting lips glistened with the bright red lipstick which matched her top and skirt. Shining with perfection was her long blonde hair. It was easy to distinguish her from the other girls as they all looked like teenagers. This was no kid. This was a REAL WOMAN and my cock started to swell just from looking at her. Even if I hadn't known her I would have had to stop my car and proposition her.
As I pulled up, some guy was trying to get her to climb into his car but she kept shaking her head while nervously looking around for me. I heard the guy offer her 50 bucks. When she turned him down, he yelled at her that even though she looked good for her age she was just a little long in the tooth to attract the afternoon johns. After all he said the only ones interested in older whores were young guys looking to lose they're cherries and they only came around after dark.
I rolled down my window and yelled at her, "Hey, babe, I want to party! What will a hundred bucks get me?"
The first thing I got was a reproachful look and then a look of relief when she recognized me. She followed the look with the statement, "Sugar you just bought yourself a whole afternoon of party favours. " With a deliberate wiggle in her walk Mrs. Green shook her booty at the guy and climbed in. The dumbfounded look on the guy's face was priceless as we took off.
Mrs. Green sounded like my mother as she started to berate me for making her stand on the street corner dressed like that. She said the other girls had threatened her for being on their turf and 2 other Johns had propositioned her. I apologized and promised to make it up to her. "Where are you taking me, Dennis?" she asked.
"You don't know me remember! I'm just some young trick to you. "
"Ok sugar. I get it. ……Well aren't you some sweet young meat, honey? What have you got in mind? Have you got some green for momma and what do you expect to get in return?"
"I've got $100 and I need you to pop my cherry, "I answered. "The guys are constantly ragging on me about being a virgin and I'm fed up. " With that I started to maul her chest.