Enjoying My Sister and My Stepmom

So there it was. I was a boy, just turned eighteen, without a father.

Dad, who had been very ill for a few months, had died two weeks earlier and it could not have come at a worse time. Relationships with my stepmom and with my sister were at an all-time low and I was now on my own.

I had just finished school and was doing part-time summer work until my University course started in September. My stepmom couldn't wait for me to leave home.

After Mom's death, when I was an infant, Dad had eventually remarried, getting wed to a woman twenty years his junior. I came to understand why he did it. She was an auburn haired beauty.

Dad was wealthy at the time of his second marriage and, because he had heard stories of younger women marrying for money, insisted on a prenuptial agreement. In the event my stepmom behaved well enough for the marriage to last and at one point Dad was more in love than ever. However, towards the end I am sure he had his misgivings, although being ill he could do nothing about it.

To ensure I understood the new relationship, she had insisted I called her "Mommy" from the start and continued on that insistence right through my schooling. She also insisted as well that Dad referred to her as "Mommy" when he spoke to me.

I don't know why she disliked me. I had a sister who was two years older than me and the two of them seemed to hit it off from the start. My stepmom paid for Cynthia to have the nicest dresses for the school dances. Anything Cynthia wanted to do, from horse riding lessons to ballet classes, was immediately agreed.

I, on the other hand, rarely had things agreed. It was only when my Dad stepped in, to insist on Billy having his share, that my stepmom would grudgingly agree.

Unfortunately, Cynthia had the same selfish attitudes as her stepmom, which is probably why they got on so well.

I sat sadly at Dad's funeral a week after he died. He and I had always got on well. When I was younger we enjoyed fishing together and I helped him with jobs around the house. I only wished I'd done more with him before he became ill. I'd seen the signs that he was not as healthy as he should have been, but I was very tied up with final exams.

Cynthia was at the funeral of course, dressed in a coat that hid her figure. At twenty, she looked gorgeous, a lot like the pictures I had seen of my mom before she died.

Cynthia was a tall busty blonde beauty, at five feet nine she was only two inches less than me. We didn't look much alike except for our thick earlobes which seemed to run on my dad's side of the family. She had been the schoolgirl most boys in the neighborhood fantasized about as they jacked off, including me.

She had just come back from a two year gap trip round Europe, paid for by my family. At the end of the summer, she was to start at New York University, also paid for by my family. She wouldn't be sharing student accommodation of course, but renting an apartment in Lower Manhattan near her campus.

Now she was back in town for the summer, she was staying with some girlfriends while apparently doing nothing but swimming and sunbathing.

At the funeral my stepmom looked as beautiful as ever. At thirty-seven years of age, she was a Christina Hendricks lookalike and deliberately dressed to enhance all her attributes. When she first arrived in our house, she used to hug me to her bosom to emphasize she was my new Mommy. I hated it at first but, when I hit my teens, she gradually realized how much I enjoyed snuggling hard against her big breasts and immediately ceased any kind of physical affection with me.

Directly after the funeral, my stepmom took me aside and told me that in his Will, Dad had left me nothing. She had been left the house and all the cash and investments. She said that my father had asked her to look after Cynthia, but that I was to look after myself.

Charitably, she said that I could stay in the house for two weeks to sort out my room and my things in the garage, but after that she never wanted to see me again.

I was devastated. Not because my father had not left me anything in his Will, but at the thought that he hadn't cared for me.

I knew I would be able to survive. To get through college, I would have to use my small amount of savings, obtain a loan and find a job to pay for my day to day expenses. Somehow I would get by and it cheered me up a bit to think that at least Dad believed I would survive on my own.

I was still feeling very down, when two days later I was coming back from my summer job and saw a well-dressed business man waiting by our front door.

"Billy Smith?" he asked.

When I gave an assent, he presented me with a large envelope and explained that he had been told to give it to me personally. He then disappeared, leaving me puzzled.

I wearily went in the house and straight to the kitchen to put together the quick meal I had purchased. My stepmom had been ignoring my existence, clearly impatient for me to be out of the house, so made no greeting as I passed her.

The weather was warm. It seemed even hotter than usual for the time of year. After I'd eaten, I showered and lay on my bed to relax and read the contents of the envelope.

When I opened it, I realized that it was a letter from my father. My hands were trembling with emotion as I started reading my father's document, hoping that it would convey some of the love which I'd believed he had felt for me.

I gave a sigh of relief when it started with a loving greeting and a sincere wish that he had seen more of me.

He then went on to talk about "Mommy". It was interesting reading:

"Mommy and I agreed that I would make a Will leaving everything to her. However, it was clearly understood that in the event of me predeceasing her, which seemed likely given our respective ages, she would allow you to share the house with her and give you a financial settlement which would fund you through University. I knew Mommy would see that your sister would be OK. The two of them are as thick as thieves and only seem to care about each other.

Your Mommy promised me that you would always be welcome to stay with her and that your financial settlement would be generous. However, I never fully trusted her, nor sadly my daughter.

Towards the end I suspected that Mommy was having affairs with other men. Looking like Christina Hendricks, it was only natural that they would be attracted to her like flies. I tried to keep her sexually satisfied. Over the years I'd found the little kinky things which could turn her on, but in the end she lost interest in me.

I found that I was losing my trust in her and was worried that, when I died, she might decide not to stick with my wishes, especially as she seemed not to care about you at all and was only interested in your sister.

I therefore resolved to protect you and make a later Will leaving everything to you. This Will is lodged at the attorney's address listed at the end of this letter.

If my wife has abided by what we agreed, then I know you will take no action. If, however, as I fear, she has no intention of you living with her or, if her financial settlement to you is less than generous, please activate the later Will immediately. She will want to challenge it, but will have difficulties."

I smiled ruefully. Being given nothing is certainly less than generous.

In the package was another envelope marked, "Addendum - To be opened if you activate the later Will."

I opened it immediately. It read as follows;

"Actioning the second Will will mean that you will have everything, whilst Mommy and Cynthia will have nothing. This will give you immense power over Mommy. I know that you have lusted after her since your first boner. I have come to hate her so much that I want you to feel free to take whatever you want. However, think of her as a present to be slowly unwrapped and enjoyed. Take a step at a time.

P.S There are some notes at the end of this to help your enjoyment.

P.P.S I have never received the least bit of love from my daughter, your sister, so make sure you receive whatever you desire in recompense from her if you end up funding any of her college expenses."

I glanced at the notes he referred to, but decided to read them at length on a future occasion.

Reading this addendum to his main letter made me realize that he must have come to hate my stepmom. He clearly had no problem with me taking sexual advantage of her and almost seemed to relish it. He had also implied that he had no problems with an incestuous relationship between his son and daughter.

He had enclosed a copy of the second Will and I slept with it under my pillow, dreaming very happy thoughts.

The next morning I threw a copy of the later Will on to the table where she was having breakfast and shouted, "Read that Mommy," as I walked back upstairs to take my shower.

She'd looked up startled, not I think from the thud of paper, but from my use of that maternal endearment which she knew I hated.

Half an hour later I heard the front door slam as "Mommy" (I was beginning to enjoy that word) left the house and drove off. She obviously wanted to know as soon as possible if the new Will was legitimate or a fabrication.

I phoned work to tell them I would be delayed. I was paid by the hour and they wouldn't be too bothered.

Following my phone-call I went into Mommy's room and turned on her computer. It didn't take me long to work out her passwords which were either the name "Cynthia" or Cynthia's date of birth. Her emails were interesting. Apart from lunch appointments with friends or bookings at her clubs, the bulk of her correspondence was with Cynthia or someone called Julian.

Cynthia had obviously been giving Mommy a running commentary throughout her European trip, including her amorous encounters. However, in the later emails the two of them had been discussing the financing of Cynthia's New York studies and Mommy's proposed visits to The Big Apple.

Although I could see evidence of other men in earlier emails, Julian was obviously the latest lover and the guy I think my father had suspected. He was an artist and, looking him up in the local news, not very successful. He was clearly fascinated by the sixties and his paintings were of celebrities of that period. Also included were pictures from the television series Mad Men with men in tight-fitted gray suits and the women dressed to thrill. No wonder he liked my stepmom. It must have been his life-long ambition to have Christina Hendricks in his bed.

However, it didn't look as if they had been able to consummate their relationship. He had been away for a few weeks and when he was back it was difficult for her to leave my sick father without it arousing suspicion.

They were due to meet this coming Saturday. He was pretty crude, writing that he was "looking forward to fucking Christina Hendricks". Although my stepmom's response was not so unsophisticated, reading between the lines, it sounded like she hadn't had sex for a very long time and was gagging for it.

Returning to my room, I sent an email to the attorney, informing him that I intended to activate the later Will and made an appointment to see him on Wednesday, the next day.

When I returned home from work later in the day, my stepmom was not yet in. In fact it was quite late before she made an appearance. She looked ashen faced as she barged passed me and slammed the room of her bedroom door behind her.

The next day I called on Dad's attorney. He made clear that the later Will was completely legitimate. Apparently my stepmom had called on him the previous day to say that she had been advised by her attorney that she had strong grounds for challenging it. However, Dad's attorney had pointed out that the prenuptial agreement, which she had signed before her wedding to my father, prevented her from benefitting from his death, unless there were statements in his Will to say otherwise.

My father's estate was far larger than I had thought. The attorney said that my father believed that, despite their treatment of me, I would be generous to my stepmom and my sister.

Grudgingly, I admitted to myself that I could afford to be generous even to the point of continuing to fund my stepmom in her current lifestyle and to pay for Cynthia's expensive New York University course. However, they would both have a price to pay.

It was still warm as I walked in the front door to see a salad with prawns on a plate at the table. I assumed it was for my stepmom, until I saw her coming through the kitchen door with an obviously forced smile on her face.

Even with an apron on, she looked gorgeous, more like Christina Hendricks than Christina Hendricks did herself. Her breasts pushed out her blouse above the top of the apron. Her shortish auburn hair hung with a light fringe above her big blue eyes which were set in her beautiful lightly freckled face with its glossy red lipstick.

She had clearly tried all the legal advice she could get but it had only confirmed her worst fears.

She smiled again benignly. "Billy, I want you to know that this change in your father's estate is a relief to me. I never wanted all the responsibility. I'm so glad that you're now in charge. I know I can rely on you to treat your mommy fairly."

I smiled to myself and said, "Don't worry Mommy, I'll treat you entirely as you deserve."

She didn't know what to make of this and looked uncomfortable as she continued, "As you probably guessed, I was going to give you a generous financial settlement. It would have been a lump sum which would have funded you through University and made you quite comfortable afterwards."

It astonished me that she could make that statement so brazenly. I continued to feel amused as she carried on, "I know you will wish to do something similar for me. To help you calculate how much the lump sum should be, I have made a list of all my regular requirements."

Following her explanation, she passed me two sheets of paper listing all her memberships, subscriptions and regular payments as well as daily spending money. I took it from her and, as I started eating my salad and prawns, promised to consider everything she'd put down.

She would obviously have loved to press me for a timescale, but clearly thought better of it.

Having enjoyed my meal I said, "Thank you for the meal. I would like a meal ready for me every evening."

"Of course sweetheart," she replied.

"Also," I added, "at the end of the day I'll be tired, whether it's from being at work or from working on my finances in Dad's study. From tomorrow, I'll need help relaxing."

She immediately understood what I meant. "You can rely on me." she said sweetly, walking back into the kitchen.

I smiled, watching her ass as she walked out, her globes moving seductively under her dress. I would start my games with her the following evening.

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Dad had converted a downstairs room into an office, where I worked on analyzing Dad's investments all of the following day, with a brief exception. When my stepmom went out for a lunch appointment, I crept to her room and looked at the latest emails.

My stepmom had patently given a very clear description of the position to my sister, who was very unhappy. Cynthia had firstly assumed that her stepmom would still somehow pay for her New York studies. When it was made clear that was impossible and furthermore my sister would have to somehow get the funding from me, Cynthia was unmistakably distraught.

The communication finished with my stepmom saying that she was worried she herself would not get enough funding. Furthermore, if Cynthia wanted any money at all then she would have to come here and beg me.

As I returned to my office, I considered how the stepmom/daughter relationship appeared to be fracturing and was amused at the tetchy tone of Mommy's comments.

At the end of the afternoon, I put aside my paperwork and went in the dining room to eat. As soon as I saw my stepmom, I had an immediate boner. She had prepared another salad dish which nearly looked as edible as she did.

As I ate my meal, she innocently enquired, "Have you considered what financial settlement you will make to me?"

I looked thoughtful as I replied, "It's taking a while."

She continued, trying to hide her worry, "Have you crossed anything through?"

"Some items look a bit unnecessary," I said slightly pessimistically, "but I'll look at them again," I added, seeing her look of concern.

"Right," I said getting up from the table, "I'm going to have a shower. I want you to join me, to help me relax."

I left the room directly, not even glancing at her. This was it. Would she fall in line, or not? My mouth went dry as I desperately hoped she would follow me.

I went upstairs, stripped off and stepped in the shower. As I let the water cascade down my face, I heard a sound behind me and, glancing backwards, I saw my stepmom demurely dressed in a full fitting swim suit. She must have been thinking about this situation all day and planning how she could ameliorate the embarrassment.

I smiled to myself and thought, as dad would have wished, that I was unwrapping my present slowly.

She came up behind me, pushing her cotton clad breasts into my back and put her arms around me, stroking my chest.

"Is this what you want Mommy to do?" she whispered in my ear.

I said nothing, just breathing in the smell of her perfume, which was enhanced by the heat of the shower.

She slid her fingers further down my torso and let the fingertips of each hand rest either side of my groin.

She again used a whispering voice, "Are you going to make Mommy do dirty things to you, you naughty boy?"

I still didn't reply, but I loved her erotic talk. If she thought she could get away every time with a handjob, she was sadly mistaken, but I was happy for her to have the misunderstanding.

Finally, her left hand slid further down and lightly grasped my testicles. I tensed in response. She jiggled them like a pair of dice, and then scratched them with her fingernails, before finally grasping and squeezing them.

Oh boy! I couldn't wait for what her other hand was going to do.

I interlocked my fingers behind my head, pushing out my pelvis, an action that begged her to grasp my boner.

"Oh, you naughty boy!" she breathed, finally grasping the base of my shaft in her right hand.

As her hand closed around it, in a loud whisper she said, "Oooh Billy, you are a big boy!"

Her tone was jocular, but I had distinctly heard a sharp intake of breath as her fingers tried to reach around my hard teenage salami.

She slid her fingers along and around my hot love lolly. She was teasing me but also, I was sure, assessing its length and weight.

I was frantically moving my hips, urging her to move her fingers up to the top of my shaft.

At last she whispered huskily, "You've always fantasized about your Mommy doing this to you, haven't you?" and slid her fingers all the way up, grasping my throbbing mushroom head.

I groaned as she squeezed the end of my knob and jacked it steadily.

She kept up the slow steady rhythm and seemed to press her breasts into my back in time with the movements of her hand.

She jiggled my balls in her left hand as she continued the delightful slow rhythmic stroking of my helmet with the fingers of her right hand.

The slowness of the teasing working of her fingers round the end of my knob was exquisite agony. She playfully held my cock under the main gush of the shower spray so that I felt the pricks of water on the tender skin of the glans.

Using her fingertip, she gently rubbed my tender glans on the underside of my helmet. I wanted it to go on forever.

She whispered in my ear, "You love Mommy's fingers round your cock, don't you!"