Just when I thought things were starting to look up, my luck turned rotten. After two resoundingly bad marriages and the slow financial death of double whammy alimony, I had managed to score a tender young thing with an ass that promised paradise on earth. It was entirely accidental meeting Jill at the car wash because I usually washed my ten year old Chevy right in the driveway. She brought the happy back into my life with her submissive attitude and willingness to try anything at least once to see if she liked it.

Jill was not what one would call "beautiful" and in fact perhaps even "pretty" was not the proper title. What she had was a whole lot of super exciting sex appeal that started down on her shocking red toenails and went all the way up to her shimmering golden blonde hair that invited you to grab it and pull until she cried "Uncle!"

The first time I was fortunate enough to navigate up Jill's vaginal channel until I grounded hard on her giving cervix, I understood what the word "tight" actually meant. The base of my happy dick was being squeezed so hard by her seldom opened lips that my ejaculation came much quicker than I wanted. I drained into her with regret knowing that she had not achieved any semblance of a happy ending and I was just robbed of precious minutes of "being on top" time. We were like sparring partners in the bedroom and in all honesty it seemed like we were destined to only engage in fifteen round events.

Even the downtime with my new-found love juicy Jill was productive because she was trying to perfect her oral skills after years of regretted abstinence. Seemed she had been caught up into one of these "cult" type programs that preached oral sex was a mortal sin. It seemed so backward in a time when most high schools were training grounds for young pussies to learn the ins and outs of mouth manipulation. I had to admit that neither one of my ex-spouses had shown any talent for the mouth to cock resuscitation program but I was the one at fault for picking them out as partners. No point crying over spilt milk as my mom would often say.

This was the week of the big race and I was really looking forward to a long session out at the track. I sure hoped it would stay bright and sunny because I was crap when it came to picking the right nags to run in the mud. I was probably just as bad as picking a wife to journey with me through the stresses of everyday life.

My Jill was the best at taking care of me with her mouth and she was a real winner when it came to giving up her "secret garden" and even her "back there" place that made her always groan with appreciation when we were going at it real hard and heavy. I had absolutely no complaints with Jill on that score but when it came to matters of luck and good fortune, it was another story entirely.

The first time I took Jill to the track it was a complete disaster.

Not only did I lose my entire day's stake on horses that should have won going away, but it seemed every time I tried to give my much-valued advice to friends and associates, they lost their shirts as well. Bye the end of the day, I had no followers around looking for scraps of inside dope.

I tried to put it all down to just an "off" day but the seed of suspicion flowered like a stink weed when the same thing happened the next time she accompanied me to the race track for an all-day affair figuring the odds. As an experiment, I sent her to the cashier booth out in the grandstand area to cash some winning tickets from the previous week that were burning a hole in my pocket. I knew it would take her at least half an hour to accomplish that mission and it gave me time to bet a bundle on a seven for two over-lay that the pari-mutuel hounds missed entirely they were so hot to trot for an inconsistent favorite. The sweet thing came in under the wire paying $9.20 on a two dollar ticket. I had two large on the nag and scored a payoff of $9,200 that made up for all my losses on the two days at the track with Jill at my side. She came back with the winnings from another day and asked me,

"Did I miss anything?"

I didn't have the heart to tell her she was an out and out Jinx and not an appropriate sidekick for a professional gambler. I just made up a story about not finding a good horse in that last race and we went back to the apartment with her wearing a big smile on her face thinking I was happy to have her with me at the track.

Later that night, I remembered her bad vibes and gave her a mean-spirited spanking that made me lick and kiss her ass all over from a guilty conscience. She practiced her oral techniques and I told her she was "the best". I wasn't lying when I told her that because she really was the best mouth fuck that I had ever come across.

Now I was faced with a real conundrum.

I certainly did not want to lose the best thing that had ever happened to me in the world of sexual interaction but I feared the damage she could do to my gambling reputation if she remained at my side in sporting events. I decided I would keep her with me but told her that it would be better if she didn't go to the track anymore because it was a bad influence on her moral values. I don't think she fully bought the silly reasoning but when I gave her cash for a nice shopping expedition she lost all interest in the horses and the shady characters that always surrounded my box.

That weekend I scored big time on a trifecta and we celebrated by having a fetish orgy behind the locked bedroom door. I convinced her to wear the tiny jockey saddle and I mounted her wearing only my riding boots and colorful jockey cap that looked a bit like a rainbow. Somehow, we wound up with my dick in her ass and she wailed out her appreciation so loud that I was sure old Mrs. Prendergast who lived next door could hear every happy thrust up Jill's willing backside and she probably had her ear to the wall so as not to miss a single beat. If she were a bit younger, I would have given her a ride just to keep her mollified but I was afraid to chance it since she was old enough to be my mother just like I was old enough to be Jill's father. On the other hand, if she gave me any more than a polite smile, I probably would have boned her standing up just to show her she still had a nice looking ass.