Chapter 3

My sister’s husband was banging me fairly steady now and using my rear-end for his more perverted needs. I didn’t mind the humiliation, because I knew it was because my prim and proper sister was too religious-minded to take it up the ass. I didn’t see any reason to hold that against her, because I had come into liking getting it up the Hershey highway more by accident than by intention. It was my brother-in-law with his nasty buggering obsession that got me into the habit and I did my best to hide it from friends and relatives. I had managed to do it thus far by limiting my bum humping partners to absolute strangers, other than the demanding Harry.

The Brazilian couple I worked for had worked my rear end over hard enough to insure it was in tip-top shape for any anal antics that came my way. I had discovered that most of the married men I came in contact with were all hot for slipping it between my cheeks than just normal old sex the missionary way or a bit of oral exercises. The girls in my graduating class had bragged about their ability to take it “back there”, but I was wise to their lying ways and figured they all had made up the stories to sound like they were tough and ready for anything. I know that the first time Harry bent me over; I was hooked on getting it that way and would never go back to normal sex again.

I had started a daytime job at a local pawnshop and worked under a huge black man from Jamaica called Doc Deep-six. I knew it was not his real name, but just a nickname he had from the time he had left the islands. I believe his real name was Oscar Waddington and I could understand why he preferred his alias working in an industry where any sign of weakness was a sure way to invite getting scammed.

My mom warned me that a proper church-going white girl shouldn’t be working under a black man no matter how handsome he looked and how romantic his accent was when he opened his mouth. In all honesty, I acted like it was all the same to me and men were men no matter what color their skin was. Actually, that was a bit of a lie, because I was afraid of Doc Deep-six. The girls at the shop had spread the rumor he had to leave the islands because he had impregnated too many white girls of high society and he was an embarrassment to too many influential rich people with daughters possessing total lack of morals. Poor Doc was a quiet man and from my observation not inclined to pressure any female for favors like the rowdy lads down at the sports bar.

I have to confess that most of my sexual experience up to this point was from married men and I was a lot more comfortable bending over for an experienced man with a wife and kids and lots of experience in doing almost every kind of kink imaginable. I generally just put my hands up in a submissive sign of complete surrender and let them show me what they wanted. I was mostly frightened of my boss because he was a huge man towering over me and I feared his weight on top of me in some sort of coupling experiment with me on the bottom. I had also been treated to several exaggerated stories of the size of his member that the other girls swore was big enough to be mistaken for a horse dick or even worse. Of course, I had no idea what a horse dick looked like never having ridden a horse in my entire life. I was a city girl through and through and life on a farm was not in my plans for the future.

Ever since my silly sister had gotten pregnant again by sheer carelessness, my brother-in-law was giving me the business up my backside early in the morning before he went to work. My sister generally stayed in bed and Harry could pound my teenage bottom happily as we showered together in the hot water and copious suds from my sister’s bubble bath. I have to admit it was an addictive thing now and I looked forward to it like my morning coffee and a bit of toast and jam. I sort of pitied my sister missing out on draining that vibrant cock in the early morning hours but she had her own agenda and her own way of doing things. In fact, I half suspected her of giving it up to the milkman after we left in the morning, because he had a spring in his step coming up the walkway every time I saw him whistling past me with a tip of his cap. He looked like the sort of fellow that would lick pussy to get what he wanted and I knew my sister demanded that kind of foreplay before she spread her knees.

The job in the pawn shop was not high paying, but it gave me the benefits I needed for the other perks of being in the labor force. I didn’t get any of them in the babysitting business other than the opportunity to get outrageous tips for being submissive to my employer’s other needs. It was more an adventure than a business venture and I never knew what to expect from the horny husbands in the middle of the night. I got to know the ins and outs of giving head in tight quarters inside a motor car and bending over for anal games hiding my face in my elbow like a silly schoolgirl. I found that the more I pretended to be inexperienced and downright shy, the bigger the tip for “optional” services at the end.

On Fridays, I began to accompany my boss to the bank for the payroll briefcase and he would sign documents whilst I double-checked the amounts in each envelope. My sister’s best friend Amy worked at the bank as a clerk and she always offered me tea while we were waiting. I enjoyed the break away from the routine in the shop but I was somewhat nervous about driving around here and there in town sitting next to a huge black man with hands that dwarfed the steering wheel. I think part of it was a form of prejudice because I generally stayed away from black boys with their reputations of getting white girls pregnant and just walking away without a care in the world. Then, there was such a difference in our heights and size that we looked like an adult with a little girl that was obviously not his.