Tricks

Some people have some great and romantic reason for running away.
They were being beaten up, raped and just plain told to leave. I have none of those th, ju, just an incredible urge at 16 to take off and be on my own.
Nothing was insanely wrong at home. Sure I had all the normal angst that goes along with being a teenager and living at home, fight and stuff over the stupid things my parents would say and do. Not being able to use the phone after 10 pm, having to be quiet in morning when my mom had worked late the night before, even running water setting her off. I just really needed some breathing space.
So that’s how I ended up that night on a street corner downtown, my last 15 dollars feeling very light in my pocket. I had long ago used up all the friends that I could go to and spend the night. My only friends were the kinds who still lived at home and didn’t really feel comfortable taking in run away, even if they are friends of their kids.
Luckily it was warm night. I leaned against a wall watching the prostitutes hanging on the corners, smoking their cigarettes and trying to look sexy doing it when what they really were either bored or anxious. I think the last emotion they felt was sexy.
I stood there for about an hour watching cars stop and a girl go up and do that hooker lean over into the open window, inevitably getting in and driving away.
I was so fucking jealous! I wish it could be that easy for me, just have some woman drive up and ask me my price for the evening. The only thing I would get is some old queer asking me that.
So imagine my surprise when a car stopped in front of me and the window rolled down to show a rather attractive older woman looking out at me. It was pretty easy to see that she was nervous even though she tried not to show it. She kept cutting her eyes up and down the street, trying to see if anybody she knew was passing. And I could see how she would. She was driving a black BMW with a leather interior. Her hair had what looked like an expensive salon cut with blond highlights in the natural brown.
“Hi,” she said, a very cultured voice that sounded more sure then her eyes. “Are you working tonight?” I was still taken aback by all this but I found myself saying that I was.
“How much?” was the simple question that nearly made my mind freeze. How much? What did hookers charge? Was it different if you were a guy?
I tossed a mental die and said “20 dollars an hour and 100 for the night.” I nearly kicked myself for quoting such a high price for the whole night! Why didn’t I say 50? Then I would at least have a chance and not sleeping on a grate!
The woman looked at me and just when I thought that she was going to drive off she said to get in. I quickly picked up my knapsack and walked around to the other side of the car and sled into the seat. She shot away from the curve and headed off to god knew where!
As we drove in silence I looked at her out of the corner of my eye and tried to peg her age. She could have been anywhere from 35-55. Who knew what kind of plastic surgery she could have had or afford. I suddenly thought of my mom who was always worrying about what working nights was doing to her and trying every knew wrinkle fad that came out.
The woman interrupted my thought by asking my name, I told her and she said that her’s was Grace. Some how I thought that she had been spending the time trying to think up a phony name. I started groping for things to say as the silence spun out, me staring straight ahead of me and her stiffly driving. I hope she was having second thoughts and wanted to kick me out of the car. Maybe while it was still moving!
“So how long have you been…working?” she asked, not sure on the word she should use. I sympathized!
“A couple of weeks now,” I lied. Even as a gigolo I had to lie about how much experience I had. The thought almost made me life right out loud.
Then it hit me! I didn’t have any kind of protection. Did she? Who was supposed to be the one to supply the contraceptives? Was there a system to this?
I was sooo over my fucking head!
“Um….”I started embarrassed. “Do you have anything? Protection I mean?”
I saw her stiffen even more if that was possible and then give a good-natured laugh. “Uh, no. I don’t. I didn’t know I was supposed to be the one to supply it.” She glanced over at me and I could see both her cheeks were flaming red. “This is my first time…doing something like this.”
“Hey, there a first time for everything!” I said lamely and we both laughed. It was that or face the fact that we were lost.
She pulled into the parking lot of a shopper’s drug mart and she went for her purse.
“ No,” I said. “Its okay. I\'ve got it.” She smiled and watched me get out of the car with my bag and head inside.
I immediately started to case the joint. Looking around at the counters, seeing who was up front, what their line of sight was, if there were cameras and if so what were the blind spots. Even before I had run I h I had been a chronic shoplifter. It kept me sane in a way. I always had this hole right through the middle of me. I always knew that I wanted something but I just never knew for what. Sometimes the hole would grow a voice and it would get so loud that I would have to find a way to make it go quiet. Stealing helped. It didn’t so much make it go quiet but was just louder then the hole.
I headed down three aisles before I found the condoms and was taken aback.
Exactly when did all these different kinds come out? There were long and slims, magnums, lubricated, studded, flavored, colored. Exactly when did picking a condom became like ordering coffee?
Yes, I would like a long grande, strawberry flavored with water based lubricant on the side.
“I am so in over my head here,” I said out loud. I mean what exactly would this woman want? Hadn’t a read somewhere that some people were allergic to latex? What if I killed her?
And just what size was my dick anyway? The only girl I had ever had sex with had been a virgin and on the pill so no condom was used on the dozen or so occasion that we had screwed. I reached out and pulled out a box of regulars lubed and unlubed. I was going on faith that I wasn’t small and I wasn’t egotistical enough to even touch the magnums. I flipped a coin in my head and put the lubed ones back. I headed back up to the front and picked up some tic-tacs as well and tossed five in my mouth as I went out.
She was still waiting, seeming a little more relaxed. I wondeif sif she had given herself a little pep talk.
“Got what you need?” she asked with new confidence. I said that I did. When she shifted to drive and turned the wheel, I looked at her hand. No wedding ring. But I had been looking beyond the obvious for years and saw the indent and paler skin circling around her left ring finger.
So she was married. nderndered if her husband had a gun.
The drive to her house was silent but a little more relaxed. She had turned on the radio to a soft rock station and began singing softly along to Celine Dion and Madonna. Was I really about to fuck this woman for money?
The house was huge, with its own road leading up to the house. I sat stunned as she opened the garage with a remote and drove in. when she got out I followed and we entered the house. She flipped a switch and the room was brightly lit. It was definitely rich. Persian rugs and paintings everywhere. I could even recognize some of them.
She led me away from all this and up stairs with the fanciest banister ever and into a bedroom about the size of a small gym. More art and rugs and wooden furniture. She disappeared into the bathroom and I looked around. One a bedside table I saw the picture of Grace and a man who must have been her husband. They looked pretty happy.
When Grace came back out she wore a long, white robe. Looking nervous all over again.
It occurred to be that it was my job to make her unnervous.
Okay, I can do this! Girls on the strip do this all the time!
Yeah right…
“Uh, why don’t you come over here to the bed,” I said, dropping my bag on the floor. She slowly made her way across the room, one hand clutching the front of her robe closed. She looked ready to run to Paraguay in a second.
Think fast!
I looked at the dressing table and saw many oils and lotions.
“Okay, okay,” I said more to myself then to her. “Why don’t you lie down on your stomach and take off that robe.” She slowly did as I said, showing me that she was naked underneath. No matter what her age was she had a nice tight ass and slim figure with a bought tan. I removed my coat and all my other clothes. I didn’t mind being naked, hell, it might help her a bit. I got one of the bottles of oils and sniffed it. Didn’t smell nice. What the hell was it for. Got another one and smelled. It smelled like strawberries.
I nodded in satisfaction and came back to the bed and straddled her thighs. She was as stiff as a board under me. I poured some of the oil along her spine, thinking this might be sexy. When she jumped a bit and looked back I stammered that I was sorry.
She smiled that reassuring smile again and said, “Its okay, just a little cold is all.”
I smile back and put some on my hands as well and begin spreading the oil around, up to her shoulders where I began to massage her. Along her neck, shoulders and down her back, pressing into her spine and slowly, very slowly I felt her muscles loosen under my hands.
So far so good.
When I got down to her ass, I hesitated for a moment along her hips and then took the plunge, spreading more oil onto the cheeks and spreading it with my hands. I grew bolder as my “what the fuck” feeling came on that I liked when I was about to do something bold or stupid. I rubbed it all in, even tracing my fingers along the crack and a little inside. When her ass began to clench I thought I had gone to too far until I saw that her cheeks were clenching then releasing, clench, release.
I went to one leg and massaged it, getting my hand between the thighs to rub the inside. My finger skimmed across her pussy and I felt her hips buck a little.
So I did it again.
Pretty soon I was rubbing my entire hand along her pussy, forcing the legs apart re mre my hand. My middle finger went between the lips and into her and I finger fucked her. Really I didn’t know what the hell I was doing but since she seemed to like it so I went with it. Her breathing was deeper, her face was buried in the pillow, her ass kept clenching and I felt her pussy tighten around me. When she came it was so sudden. Again for about the thousandth time I had no idea what was happening till I heard her moan and felt her shudder and tighten ad myd my fingers.
When she relaxed she rolled over and I saw al of her for the first time. She was really pretty actually. Her breasts only had the tiniest sag to them, something you would even see in really big chested girls my age sometimes. Her stomach was flat and pussy trimmed. Her face was very red but she was smiling.
“Well, that hasn’t happened in a while,” she breathed out.
“What about your husband?” I asked like a complete and fucking moron!
“We haven’t had sex in almost a year,” she answered, totally calm.
“Why?” I found myself asking, wishing I could just shut up. I was sure this woman didn’t want to be thinking of the man she was cheating on.
She answered anyway, pulling a cigarette from a bedside table drawer. “He has become impotent and he’s too proud to go see a doctor about it. He thinks it’ll just fix itself” she added with a small laugh, smoke puffing with it.
“So why a year?”
“I don’t know,” she admitted. “ I suppose I looked at the calendar and thought ‘a year ago today I wasn’t thinking about using my electric toothbrush as a sex toy.”
I broke up over that and she joined me, a nice comfortable moment.
“So it got that bad?”
“Yes!” she emphasized. “So bad that I actually started masturbating. Even when I was your age I never did. Never saw the point…”
“Why do it yourself when you can get someone else to?” I finished for her.
She looked at at me surprised and said yes, exactly.
I smiled cause this was going pretty good. Maybe she would let me stay the night after all. “Was he a good lover before?” I asked.
“Well, it wasn’t like explosion or anything you read in one of those trash novels but it was good.” she sighed and added. “He used to go down in me very well though.”
Seeing that as an invitation I bent myself down and slid my head between her legs. I opened my mouth and took her whole pussy in my mouth, licking it all over. This was about my third time doing this. She didn’t taste anything like Cindy, the girl I had screwed but it was still good. I stuck my tongue inside of her and her thighs closed around my head. When my lips touched her clit they tightened. I sucked on her clit and licked it up and down, her hips moving little circles. It took me awhile to realize that she liked it that way anrclercled her clit with my tongue. She began to moan and gasp, rocking her mouth against me. When she came it was hard, her thighs squeezing my head, I rode her out, until she pushed me away.
She saw my worried look and said she just got really sensitive after.
We talked some more, for maybe an hour about her family, her husband, his job that took him away so often and…just her life.
We finally actually used the condoms, which fit perfectly thank god. I was on top fucking her when she began to cry, now this scared the shit out of me but she said that she always cried, though she didn’t say why. But being sixteen I still fucked her and came when she did, clenching on to me.
I stayed that night with hnd snd she gave me 150. She said that she liked that way I listened to her as she kissed me and sent me off to my cab that took be back downtown.
Ten years later I still think about her a lot. She became a regular until she just stopped coming one day and I never found out why. Maybe her husband finally got it back up and I’m no competition for that. No matter how many times I made her cum, she loved him.
Women are funny that way.
But she taught me that it was two organs you needed to satisfy a woman.
The ear as well as the dick.