Enjoying My Sister and My Stepmom Ch. 02

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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 nişantaşı escort 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.

I made notes on all the charities Dad had listed and then thought about my cousin Lucy.

I’d forgotten about Lucy Chang and her mother Chunhua. Chunhua apparently means Spring Flower in Chinese, but it was obviously decided that the less exotic name “Lucy” was more appropriate for her American daughter.

The last time I had seen Lucy was as a little girl. I remembered her as a small plain child who was entirely spoilt and who gave me a hard time similarly to the way my stepmom and sister treated me. There was a sizeable Chinese community in our town. I had many good friends at school, boys and girls, who were Chinese, but my cousin was the only child of Chinese heritage that gave me a hard time.

Dad obviously felt that she could need financial help and, as it was important to him, I accepted that I would probably need to do something to make enquiries. In the event, I didn’t need to initiate anything as I was phoned by Auntie Chunhua. She’d heard about my father’s death through a friend.

“Billy, I am so sorry about Eric,” were her first words after our introductory hellos.

She sounded genuine and so did I responding, “Thank you Auntie. I’ll pass on your condolences to Mommy.”

She still sounded genuine when she added, “It’s a great pity that we haven’t seen you in ages, so you must come and visit us if you get the opportunity. I’ve emailed you some photos of our family which I thought you’d like to see.”

Interested, I opened my email inbox and clicked on the images in her email. They were dated fairly recently and I could see that one was of Lucy’s eighteenth birthday. Auntie Chunhua was looking a lot older than I remembered her. Also very changed was the plain child I remembered. In her place was a gorgeous innocent-looking petite young woman.

Lucy had strong traits of her Chinese ancestry with short dark hair, big round very dark brown eyes and high cheek bones, but this was combined with sensuous luscious lips that reminded me of my sister. Her thick earlobes, which were certainly inherited from our side of the family being common to my sister and myself, did nothing to detract from summing up her face as beautiful. She was small, about five feet I judged, but her slim body looked perfectly proportioned.

Standing with Lucy in most of the photos was a smart-suited young man who looked like he wasn’t short of dollars.

Having thanked her for the photos, I then listened politely to Auntie Chunhua giving me the detailed story of the last ten years of family life. However, unfortunately her tale changed suddenly to her telling me that Lucy needed money and that Auntie and Lucy both expected me to provide it. I was a little taken aback by her assumption ortaköy escort and asked rather curtly for more of an explanation.

Auntie then went into a long account. Apparently, Lucy had been engaged to the guy in the photos. His family was rich and, when Lucy was to marry, the intention was for her to be a lady of leisure. Unfortunately, her fiancé’s father lost all his investments in a stock crash, leaving the family in debt. Lucy then ditched her fiancé immediately. She was now intending to go to University and needed funds. Lucy had been offered a University place. It was a modular course so she could start in the Spring term and catch up on what she’d missed later on. As they knew I had funds they expected me to contribute.

I gathered that “contribute” meant “pay it all”.

In her telling of the story, Auntie also gave me her old fashioned views on the immorality of young people sharing a room together on holiday before they were married, so I gathered that young Lucy was not as virginal as she looked.

Although, in his notes, Dad had suggested that I might help Lucy financially, I was feeling peeved that Auntie and Lucy should have seen me as such an easy touch. It was with some coolness then that I said to her, “The course looks expensive, I’m not sure I can help. I’ll have to think about it. I think I have to say No.”

I could hear Auntie breathing heavily as her brain worked hard to stop me giving a negative finality before we closed the conversation. Eventually Auntie said, “Look, Lucy will be near your home just before Christmas. If she could stay with you and your mother say on the twenty second of December for a couple of nights she could show you the course literature and explain why she wants to do it.”

“Well OK then,” I said with feigned reluctance, “but it will be difficult to persuade me.”

As we finished the conversation with that planned visit, I looked at Lucy’s luscious lips in the photos and rubbed my boner through my pants as I thought about how her persuasion could be fashioned. She would certainly come under Dad’s “Small and Slim” category.

I could see that the timing of Lucy’s visit could work very well. My sister, Cynthia, was not due to arrive until Christmas Eve, so as my luscious cousin departed so my sexy sister would be arriving.

In respect of communication, at the end of November I had received nothing from Mommy or Cynthia, despite friendly emails from me asking them how they were doing. Then, on the first day of December, I received an unexpected but welcome email from Cynthia.

Surprisingly, it began with no animosity, but a general enquiry as to how well my course was going. It then went on to say that she was working hard and enjoying her studies. Then came the most surprising part of all. She explained how her university liked to support a local charity each year and that this year it was a Mental Health charity. She knew that this was an important charitable cause to Dad and wondered if as a family we could help support a specific local project for the Mental Health Support Team (MHST).

She had donated all she could spare from her allowance and pressed friends for donations but the MHST were still two thousand dollars short. She wondered if I could help and if I could then send a check made out to MHST to the university. She said that, anticipating my generosity, she had mentioned it to the university, so if I could mention her name they would know what it related to.

I was staggered. I now realized that there was more depth to Cynthia than I had thought and wrote back immediately to her saying I would of course do as she asked and that Dad would have been proud of her.

I started writing out a check to the MHST for two thousand dollars but then changed it to three thousand dollars as I wanted to show Cynthia the extent of my support. I added a note saying that it related to the payment mentioned by Miss C. Biggs-Smith.

As I posted the envelope the next day I resolved that at Christmas I would not be putting pressure on Cynthia on the sexual front. If she was willing, fair enough, but I resolved not to give the new charitable Cynthia a hard time.

It was a few days later that I began to receive some unwelcome news on the Mommy front. According to my attorney, he had heard that she was up to her old tricks and was questioning the legitimacy of the second Will that left everything to me. In particular she was saying that at the time the second Will was signed, Eric was acting strangely, suspicious of everything she did and perhaps was mentally unbalanced.

This was news to me. Dad was one of the sanest people I had ever met and it annoyed me that she should raise this question mark over him. Nevertheless, I thought the issue would peter out and put it out of my mind.

However, it was brought to the front of my mind with a bang two weeks later when I had another email from my attorney. This one was a lot more serious.

It appeared that Mommy had been in touch with a young pendik escort bayan new attorney in town called Mr. Lock, whom my attorney clearly disapproved of. Although my attorney hadn’t seen it, it seemed that Mr. Lock had come by a document that showed that Mr. E. Biggs-Smith was being treated at the Melbeck Mental Institute and was seen by a psychiatrist two days before and two days after he had signed the second Will.

I could see that with evidence that my father was under a course of mental health treatment at the time he signed his second Will, Mr. Lock would be in a strong position to say that Dad was not of sound mind and that the second Will was invalid.

This was serious. I had no doubt that Mommy, with full financial control, would revert to giving me precisely nothing. This was verified a few days later when I read an email from Mommy to Mr. Lock.

In the email she thanked him for all his work and said that she would be giving me nothing. She would like him to tell me when I arrived home on the twenty second of December, as she would stay out of the house until I’d left. In the meantime she looked forward to meeting Mr. Lock on the twenty first of December for lunch and then afterwards in his apartment where she would reward him as she had promised.

I knew damn well what that reward would be. Knowing Mommy she would be leaving her clitoral vibrator alone from now until she saw Mr. Lock, when she would be craving to be fucked and juicy as hell.

I resolved to go home a day early. On her calendar I could see that she had ordered her taxi to take her to the lunch at midday, so I planned to get to the house just before.

I drove home on the twentieth, battling some thick snow drifts, and booked into a hotel on Main Street a couple of miles from my house. In the morning, as I soaped myself in the shower, I wondered how Mommy would look and found myself washing a large erection as I visualized her.

Just before midday I drove over to our house. Although there was a light flurry of snow, the roads in town had been kept clear. I quietly let myself in the front door. Taking off my jacket, shoes and socks I crept up the stairs. I could hear Mommy humming a tune, obviously very contented with life, but she stopped as I perfectly timed my entrance to her bedroom.

Her dress was laid out on the bed so as not to get creased. She was standing in front of her full length mirror making the final adjustments to her earrings, wearing her bra and panties, garter belt, seamed stockings and heels.

She gasped and turned around with a start as, with a loud cheerful voice, I said, “SURPRISE!”

Fuck! She was as gorgeous and stunning as I remembered. Her brassiere, panties and garter belt were all white satin. Her lacy brassiere struggled to hold her bounteous breasts, showing a deep cleavage, Her panties clung to her full round buttocks. Straps from her garter belt were clipped to the tops of her tan stockings. She had adjusted her stockings so that the seams went straight down the back of her legs to the black stiletto heels.

She was staring stunned as if she had seen a ghost as I swept towards her, taking my shirt off, and putting my arms around her in a big hug.

She was still speechless, clearly not knowing what to do, as I whispered in her ear, “It’s wonderful to hold you again Mommy.”

I didn’t give her time to think as I continued to babble on as if I was too excited to see her to slow down. “We’re going to have a wonderful Christmas Mommy. We’ve got Cynthia coming home Christmas Eve, but before that we’ve got my cousin coming tomorrow for two nights. Sorry it’s such short notice. You remember Lucy, Mommy, we haven’t seen her for ten years but I’m sure we’ll like her.”

As I was gabbling, I was undoing my pants and removing them and my boxers.

I was rattling on so fast that Mommy had no chance of getting a word in edgeways as I continued to hold her and talk in her ear.

“We never saw much of Lucy’s father of course, Dad’s brother Ted. You probably remember that he suffered a lot from mental health issues. In fact Dad was paying for him to be treated at the Melbeck Mental Institute a few months before Dad died. Then tragically, Ted died himself shortly after.”

My speech had slowed and my tone had become suitably somber as I had talked of Ted, but I now lightened it up again. “Hey, enough of this sad talk. It’s Christmas and I know you can’t wait to give me a good time.”

With that I held her face up and kissed her open mouthed. Although her tongue was moving mechanically against mine, I could feel that her body was in a sense of shock. She had enough brains to work out that the patient she thought was her husband was in fact Mr. Edward Biggs-Smith and that she was back to square one. However, the way I’d imparted the news was such that she would be thinking that I had no knowledge of her shenanigans.

Although she stood there rigid, it didn’t stop me enjoying myself. My hands stroked over her stocking tops and pink thighs as my fingers slipped under the elastic of her panties, playing with her garter straps and gripping her plush round buttocks. As my fingers gripped her ass, I enjoyed the long kiss, switching between sucking her lips and her tongue and using my tongue to explore the warm membranes inside her mouth. Her mouth tasted of a light expensive mouthwash intended for the benefit of Mr. Lock.

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