Chapter 1

My best friend Tommy was a sort of guy that never spreads a rumor and usually keeps his mouth shut if he doesn’t have the answer to a question that all of us consider essential to smooth sailing on the sea of love. Tommy was a stand-up guy; he would be there to do the right thing because loyalty to him was the most important ingredient in any relationship. I had seen him get fucked-over by more than one girl taking advantage of his romantic inclinations and I had to bit my tongue to stay out of his doomed-to-fail love affairs that tended to be disgracefully one-sided and not in his favor at all. His last fling was with fucking Marsha Simpson. She was a bitch of a female troublemaker always ready to stab someone in the back providing she got something out of the deal that made things easier for her and not concerned at all with the impact on guys like Tommy that worshipped at her nasty feet. I knew he was far too trusting to put two and two together and question why she was still out in the wastelands of the sticks and not a player in the game of thrones back in capitol city.

I had to admit Marsha was a real hot number with her pert unfettered boobs and her sweet ass that looked like a heart-shaped invitation to unconventional warfare behind enemy lines. I knew for a fact that Tommy was not the kind of guy to be dipping into that honeypot without some crash course in anal amusements. He would too afraid of messing up and getting laughed at for making some mistake like a silly schoolboy with no idea of how to go about defeating a nubile female’s sphincter. In a way, it was probably the best thing that could have happened to him because eventually Marsha would betray him with some young lad with an impressive cock and brag about how the new guy really know how to slap the salami to her with a vengeance. It would just serve to make him feel less self-confident and that was not in his best interest at all.

I had no right to talk because my love life was a total disaster the past year. My supposed steady Heather was suddenly all hot and bothered about getting “closer” to her fellow cheerleaders and I suspected she had fallen prey to the ego-building spider’s web of beautiful girl loves beautiful girl blues. I found that it made me jealous to watch Heather and her new heartthrob Carmela playing “spin the bottle” in the back seat of my father’s old car. They considered me an “insider” to their sexy game of girl on girl relationships. I wondered how my Heather could get along without my eight inches to keep things on an even keel when things got down and dirty. I guess those two beautiful girls could find other distractions to keep them busy when they got hot and heavy under the quilted spread we used because the car didn’t have a heater. Every now and then, Heather would throw me a “bone” and let me take her from behind providing I only used her rear door and not take any chances with having a family before the right time. I have to confess I loved those moments when she just pushed her ass back at me and tell me,

“OK, Harry, do me quick. Make me take it and don’t stop until you get a good tingle.”

She sounded so much like a martyr that I fully expected her to say the rosary when I was pounding her with maximum enthusiasm. I knew she loved it from the way she was grunting each time I bottomed out and she clung to my arm so tightly that I thought she would cut off my circulation.

One time, Carmela caught us humping like that she was not at all amused.

I guess in her mind, she was the one that really loved Heather and that I was just another hard dick with no conscience when it came to free pussy. In a way, she was right on the money, but I did have sincere feelings for Heather. Of course, they were based more from comfortable familiarity than from any unbridled passion for her personality or some pretense that she was my one and only “soul-mate” forever and a day.

I knew when Heather wanted it hard and dirty from behind and I knew when she needed it nice and gentle with lots of kissing and tongue action buried to the hilt in the wet and wonderful wide-open world of Heather pussy-land.

She was sort of conflicted in that regard and I suspected it was an indication of her confusion over the simple choice of desires for a male or a female to fill the role of a full-time permanent lover. Looking at it from my genitalia focused point of view, I failed to appreciate her fickle nature about her urges to spread her knees in any direction other than my own and shamefully considered any dalliance with the same sex as a one-time experimentation to expand her sexual IQ. I was as surprised as everyone else when she finally declared her loyalty to the other side and left me out in the cold with a hard-on and nowhere to go.

In a way, I guess I was being unfair to Heather because she was terribly gorgeous and I hated to lose to a woman. If she had bent over for a hulking he-man with a two or three inch advantage over me, I could accept defeat gracefully. It didn’t seem fair that my competition was another equally beautiful female with huge boobs and an ass that could wear any flag decorated pair of bottoms with the respect it so richly deserved.

That was the sad story of my current status of frustration driven to the sin of self-gratification with dated issues of “Playboy” spread out before me like a line-up in a house of ill repute. Unfortunately, that scene was played out whilst on a sleep-over at my best friend Tommy’s house after a long night of beer and illicit video tapes. Tommy had already left for his part-time job at Luigi’s pizza palace where he was famous for his pizza tossing skills that thrilled the girls rubbing their little twats on the hard surface wooden benches. I suspected they were more interested in watching his bulging muscles on heavily tattooed arms than in the delicious orbs spinning just below the raised ceiling in front of the ovens.

I was gratified that Tommy had left me on my own because it gave me an opportunity to put his dirty magazines and my frustrated cock together for a real fun time. I thought I was all alone in the apartment because his mom was supposed to be working a double shift at the hospital where she worked in the Intensive Care Unit on a swing shift. I always felt a little nervous around Connie because she was unexpectedly attractive for a woman in her forties and had a gravity defying backside that one would expect on a teenaged cheerleader. It was all I could do to keep my eyes off her happy haunches when she was dishing out our dinner and I hoped that Tommy did not suspect I had a thing for his mom.