Author's note
This is the second installment in this story and needs to be read after the first, "Enjoying My Sister and My Stepmom".
*****
My name is Billy Smith. Well to be precise my name is William Biggs-Smith. I can't remember when my first name changed, but I shortened the surname in all my unofficial dealings when I was eighteen. The surname had been created by the family a few generations back from Schmidt. Biggs was a small town in Butte County, where the family was staying at the time and Smith sounded like an all-American name. However, I preferred plain Smith to the double barreled version.
My life changed dramatically a few months ago. When my father had died earlier in the year, it was initially thought that he had left all of his money to his wife, my stepmom. However, a later Will, which turned up in the summer, left everything to me. This meant that my stepmom and my sister were financially dependent on me. Had either of the women been of a kind disposition, I would have financed their requirements without a complaint. However, when it was believed that my stepmom would be the sole beneficiary of the Will, she made it plain to me that I would receive nothing.
With the wicked stepmother on one hand, and a sister, Cynthia, who had been equally unpleasant to me on the other, I took full advantage of my newfound power to get what I wanted from both of them. For a horny eighteen-year old, what I wanted was some sexual gratification.
Cynthia, at twenty, was a tall long-legged busty blonde beauty with big blue eyes. My stepmom, or Mommy as I called her, at thirty-seven, looked like Joan Harris in Madmen. Her auburn hair was always carefully coiffured. She was a red-headed bombshell with a 34DDD-30-39 figure. Her habitual three inch stilettos increased her five feet seven inches to a tall imperious five feet ten.
My stepmom was a woman of the world. When she had realized what I required of her in order for her to maintain her lavish lifestyle, she had no problem giving in to me. Her insistence on me calling her Mommy was irritating for my early life, but now with her sexually available I found it a real turn-on.
My sister had been a very reluctant sexual conquest, but in the end I had her begging for mercy as I pounded into her. In return I had agreed to finance her University place in New York, paying the tuition fees and the rent for her Manhattan apartment. She was required to come back home for Christmas, when I would be looking for some more sexual repayment.
However, time had now moved on. Cynthia was in her Fall term in New York. Mommy was at home living the luxury life and I had moved to a local University. I say local, but in reality it was over five hundred miles from home. The course would make me a Bachelor of Business Administration in Management. I was specializing in Financial Management and using that knowledge to participate in my father's businesses, which I now owned or in which I had a share. Given my enthusiasm for the course and the appearance of a work ethic that I previously had no notion I possessed, I found it impossible to return home during term time to enjoy Mommy's sexual favors that were awaiting me there. On the other hand, I was finding that I was good at financial management and was already achieving early success.
I had some concerns leaving Mommy to her own devices. I'd told her that I wouldn't tolerate her seeing other men for anything but social occasions. She knew I didn't trust her, especially when I said that I would be having her watched. I liked the idea that she would be looking over her shoulder all the time. I'd installed Spy Software on her computer of course, but eventually decided not to take it further and install Cell Phone Spy Software.
It wasn't so much that I was jealous; it was more that I wanted her desperate for sex when I got home. I knew the small clitoral vibrator she kept in her bedroom drawer would not be enough to keep her satisfied. She had experienced the size of my boner and I wanted her to have that always in her mind.
When I had a spare minute I would look at her email correspondence. There didn't seem to be anything there to concern me. She'd received emails from Cynthia in New York. Not inviting her there as Mommy hoped, but telling her about her love life.
Cynthia realized that to escape financial dependence on me she needed to marry someone with money as soon as possible. She had started dating an older man whom she felt was going to propose. Cynthia had dated older men previously. She seemed to find them less sexually intimidating and this latest one seemed no exception. She confided intimate details to Mommy to an extent that surprised me, going as far as to tell her that she was taking the birth control pill even though Henry couldn't get an erection every time. Apparently, instead of full sexual intercourse, Henry preferred Cynthia to administer oral sex in the back of his luxurious limousine. Cynthia went into full details on car's chic qualities with champagne in the fridge, velvet seating and gold handles.
I knew I'd be very disappointed if Cynthia managed to free herself from my financial grip, especially if she was improving her blowjob skills, but consoled myself that at least I'd be saving money.
Despite my financial success and the assertive role that I had eventually assumed at home with Mommy and Cynthia, I was still shy of girls generally. After a few tentative approaches I gave up trying to date the girls at my university. I therefore had to rely on masturbation for sexual relief when I would be fantasizing about giving Cynthia the pleasure of her brother's boner or of my big breasted mommy.
In my mind Mommy would be in her usual sexual lingerie of stockings and garter belt. I guessed I had a fetish about nylons, not so bad that I wanted to wrap a stocking around my boner to jack off, but enough for my mouth to go dry when I thought about the tops of Mommy's stockings with the flash of pink thigh flesh and the gripping erotic garter straps.
When not working or masturbating, I read through notes that Dad had left me on Mommy and women in general, but there were also some suggestions about charities he liked to support and a particular suggestion about his niece Lucy, my cousin.
One section of Dad's notes which I particularly kept re-reading were about sexual positions.
"Billy, it's great to fuck women in as many positions as possible," he explained, "but different women are a better fuck in some positions than others."
"In respect of women with huge melons, you want them on top at some point. On top they can ride your boner and thrust out their hooters. Often you may start with her underneath you, seeing her tits wobble as you thrust, but you need to finish with her on top so you have unfettered access to her breasts. There's nothing more pleasurable than having a big breasted woman riding you as you cum."
"Now smaller and slim women you want underneath. That way you can control them as you thrust your boner into them. You will also be more aware of them wriggling and squirming under you impaled on your erection."
I could imagine the category Dad would place Mommy. On Cynthia I was less sure, but her breasts were certainly growing to quite a handful.
