Capítulo 3955: 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!"As she said those sexy words, she didn't accelerate jacking me off, but gripped her fingers tighter round my tender flesh over the end of my dome.
"Oh Mommy!" I groaned as my spasming ejaculations sent great gobs of cum splashing against the shower wall.
She squeezed my balls in time with the pulsing jets of jizz.
As I leant exhausted against the shower door, she kissed me lightly on the shoulder and left.
I stood there for a while in the warm shower spray musing over what had happened. She had been able to tell that, whereas previously I hated the "mommy" language, now I found it a real turn-on. I certainly wanted it to be continued.
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The following morning and afternoon were mostly a repeat of Thursday. I worked all day in my father's study apart from a brief interlude when Mommy went out. Again I used the opportunity to see the latest emails. It appeared that Cynthia would be coming on Monday and staying three nights. She would be using that time to work on me to agree her New York funding. I licked my lips. That was fine by me.
For the first time, I now read the sex tips and observations that Dad had appended in his notes to me. It was fascinating in terms of suggestions and I was particularly interested in the section on "Mommy's Blowjobs."
Late that afternoon, when I'd had my meal, I again went off to the shower and told Mommy I'd be waiting for her. This time though I showered quickly so that when she walked in my room, she saw me sitting naked on the side of the bed waiting for her. She had expected to join me in the shower and was wearing her full piece swim suit again. She hesitated as she entered and I thought her eyes seemed to widen a little as they rested on my big boner.
I had a better look at her than the previous occasion when she was behind me. Having the same 38DD-26-34 figure as Christina Hendricks, I was reminded of the description of her as "built like a B52".
She smiled gently as she walked towards me and kneeled in front. She stretched her hands forward and grasped my boner but then looked me in the eye and said purposefully, "Mommy would like to know about her financial settlement."
"I'm still working on it," I said.
She smiled gently again, slowly jacking my hot meat, "Mommy's getting impatient."
I put my hand behind her head, lightly pulling it down towards my hot helmet. "Mommy can help Billy decide more quickly," I whispered.
She held back, obviously not expecting me to be so forward and clearly reluctant to do what I was suggesting.
After thinking things through for a moment she stuck her tongue out and licked the tip. A shock of electricity crackled down my hard penis.
She knew she was in a strengthening position when she whispered, "If Mommy was to suck you, when will you give her an answer?"
Though I was finding it difficult to concentrate, I told her through my quickening breathing, "Through tomorrow and Sunday I'll be working on your list and I'll definitely have an answer to what I can agree and how it would translate into a lump sum, by the end of the weekend."
She smiled, obviously satisfied for the moment, and licked me again and breathed, "You've always been fantasizing about Mommy sucking you off, haven't you?"
I stayed quiet.
Another lick. "Shoot your cum in Mommy's mouth baby," she huskily whispered.
After hearing that erotic suggestion, I groaned and Mommy's lips slid over my helmet, my burning boner moving in and out her hot moist mouth.
After a minute of this, I pulled out. She looked up at me in surprise.
"Just use your tongue Mommy," I pleaded.
She would have had no reason to suspect where I had got the idea from but Dad's advice proved excellent. Her tongue went to work. She licked the red eye, then drew a line with the tip of her tongue down the outside of my glans to the frenulum at the base of the knob where it connects to the shaft. Moving sideways she slipped the tip of her tongue under my rim, moving it around the mushroom head until it was back on the frenulum. She then licked the back of the penis hard, rasping the tender underside.
Having given me that treat, she went back to steady sucking, but I wanted more. "Hold my balls, Mommy," I gasped.
As her hand obediently went forward to tweak my balls as she sucked me, my hands grasped her auburn hair as she bobbed her head.
Following Dad's instructions, every time she bobbed her head, I eased my hot hard meat further to the back of her mouth. Pretty soon I was entering her throat and the feeling in my cock as it slid deep in her throat and out again was exquisite. No wonder Dad loved Mommy's blowjobs.
Using the grip of my fingers in her hair, I stopped her head bobbing and held her head steady as I fucked her throat. She'd obviously been in this position with dad, as she was able to take the whole of my cock without choking, her nose buried in my pubic hair.
Suddenly I gasped, "Mommy I'm cumming!"
She grasped my balls tighter as I slipped my boner out of her throat to her mouth where she could concentrate on strongly sucking my tender mushroom head.
"Oooh Mommy!" I groaned as my pulsing spasms sent thick ropes of jizz splashing in her mouth.
She carried on sucking and squeezing my balls until I was finally drained.
She left me again with just a peck on the cheek, without saying a word
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On Saturday, the following day, neither of us made any mention of what had happened the previous day. She told me in the morning that she had an early evening Ladies dinner, but wouldn't be back until late.
After we both had a light lunch, she went upstairs to shower and change. I went into the office, ostensibly to work on her wish list, but in reality to arrange the couch as per Dad's instruction manual.
She'd given herself a good two hours for her preparation and when she came downstairs it had obviously been worth it.
Knowing Julian wanted to fuck Christina Hendricks, Mommy had done her utmost in making his dream come true. She was Joan Harris in Madmen. Her auburn hair was carefully coiffured. She was a red-headed bombshell, the gorgeous sixties office manager. She was wearing a low cut satin green dress, showing a flash of her delicious cleavage. From those lush breasts, her torso narrowed to a wasp waist.
Her dress clung to her hips and tapered down her legs to end just below the knees.
Gray seamed stockings, which could be glimpsed encasing her lower legs beneath her hem, led down to green high heels with pointed toes.
She had a large matching green handbag, which didn't look sixties era to me. However, I couldn't see it mattered that much as I had no doubt that Julian would have been tossing it to one side and ripping her clothes off before she could sit down.
She was heading towards the door when, in a commanding voice, I said, "STOP!"
Looking towards me with a frown she said determinedly in a clipped voice, "I am going out."
Turning away from her nonchalantly, I said, "I've just finished page one of your list and I have a mind to agree everything."
She hesitated, "Everything?" she queried, a slight tremor in her voice and a gleam of excitement in her eyes.
"Everything," I confirmed. "Even your donations to both the Republican Party and the Democratic Party."
"They both do excellent fund raising lunches," she explained with an apologetic smile.
She looked questioning, "Is that why you asked me to stop? So you could tell me that before I went out."
I looked straight at her, not smiling. "No, I've told you that I am willing to agree your first list. I may even agree the whole of your second list. I can then translate your ongoing requirements into a lump sum payment."
Her eyes widened in hope, I continued, "But you will need to please me this evening and tomorrow."
She looked at me with a half-smile on her face. She must have always realized it would come to this.
For her, comparing Julian's artist's studio with my offer of financial security was no contest. She was expecting me to hand her a huge check, after which she could tell me to go to hell. She was to be disappointed as I intended to pay her by monthly allowance, but I wasn't going to tell her that too soon.
She put her bag down and nodded, following me meekly as I led my Christina Hendricks gently into the office. She didn't know what to expect and was surprised when I put my arms around her, kissed her and pushing my tongue between her red glossy lips.
She hadn't expected being kissed, but responded as she thought I would like by opening her mouth and letting our tongues explore each other.
My boner was nearly bursting out of my trousers as my hands grasped her ass, pulling her against me. I drew deep breaths through my nose, inhaling her perfume.
I moved my hands up to the top of her satin green dress at the back, unclipped the hooks and slid the zipper right down to the small of her back.
She broke off our kiss to whisper quickly with a half-smile, "You naughty boy!"
We carried on kissing until I stepped back and pulled the dress forwards. She let her arms hang by her side so that the dress fell, pooling on the floor.
Oh fuck! She looked like a sexual fantasy. She was to all intents and purposes Christina Hendricks, standing there in her luxury underwear.
Poor old Julian would have had a seizure. Her lacy brassiere, panties and garter belt were all matching green satin. Straps from her garter belt were clipped to the tops of her gray seamed stockings. The green of her high heeled shoes matched the green of her satin underwear.
I quickly stripped off my clothes. Then guiding her to the couch I sat down and said, "Right, you've been a naughty mommy and I'm going to spank you. Bend over my knee."
She froze as she realized that what I wanted us to do was what she had done with Dad many times.
I guessed with apprehension that she now realized that Dad had left me instructions, so I was relieved at what she said next.
She took a deep breath and said in a surprised and rather disapproving voice. "Why, you must have spied on your father and me when you were younger." Then, with a shrug and a slight smile she said, "At least you should know what to do," as she placed herself carefully across my knees.
I was trembling as I put my hands firmly on her thighs. The nylon of her stockings prickled the skin on my thighs as I maneuvered her so that she was balanced over my knees. Her ass was sticking up nicely in the middle.
Dad had described her getting excited in this position and I could tell how right he was as I brought a hand down with a slap on her panty-clad right buttock. She squirmed deliciously on my lap, rubbing against my boner and in short breaths she gasped, "Oh you brute! You've got your mommy at your mercy."
This sexy language was too much for me. I ripped her panties down her legs and over her heels so that her ass was fully exposed.
In my lust, I spanked her harder than I intended on her left buttock, causing her to deliciously squirm even more. This time, however, I left my hand on her buttock and slid it under her garter straps and round the milky flesh above her stocking tops. Both of my hands were then grasping her buttocks, pushing hard against the sinews and muscles with my fingertips.
Her wriggling was getting more and more intense as I eventually slid my fingers down the crack of her ass. They slid over her sphincter and down between her legs.
I'd gathered from her emails that she was desperate for sex and I grinned to myself as Mommy parted her legs, the action eagerly inviting the fingers of her teenage stepson to access her hot pussy.
My enthusiastic fingers slipped under her, parting her labia lips and sliding on to massage an engorged juicy clitoris.
"How do you like what my fingers are doing Mommy?" I said with a chuckle. She made whimpering noises in reply as I carried on working her genitals, rubbing her clitoris and slipping two fingers in and out of her vagina.
I intended to just bring her to the brink of an orgasm so she would be ripe for me to fuck. As her twisting and wriggling became more frantic I stopped.
My fingers were sopping wet as, having completed Dad's stage one, I pulled her up and onto my lap facing me.
I lifted her up and aimed my boner at her entrance. I knew I'd got her desperate to fuck, but she sank herself carefully on my big boner. She lowered herself a bit at a time, taking an inch or two before pausing until she was fully impaled.
She sat astride me breathing heavily, not moving but just enjoying being packed full of my hard man meat, which was sublimely gripped in that juicy vaginal sheath.
She was looking more composed and ready for some serious fucking when I gasped the command, "Take your bra off!"
She smiled slyly. She was a lot more comfortable when she felt she was in control, where she could use her "mommy" language to greatest effect.
She reached behind her and undid the clips of her bra, letting it fall off her shoulders, but holding it loosely against her breasts at the front like a stripper.
"Are you ready for Mommy's big breasts?" she asked teasingly.
In answer I ripped the bra away, exposing those 38DD Christina Hendrick's breasts.
Feeling that she had now secured her financial settlement she gurgled through a laugh, "Enjoy Mommy's big tits baby,"
Making no attempt to cover them, she linked her fingers behind her neck, arching her back and pushing those magnificent jugs out in front. Her hips began pumping.
I groaned, grasping those marvelous melons, mauling and squeezing them before hungrily opening my lips around her teats and sucking as much nipple and areola in my mouth as possible.
All the time she was sat erect on top of me, my boner was sliding in and out of her tight juicy cunt. She had the stare of a woman enjoying the pleasure of sex, but her beautiful face also had a half smile clearly thinking of the money she had secured.
She started moving her torso like a belly dancer, the undulations starting above her stomach and finishing with her loins grinding her pubes backwards and forwards. She was a mature woman who was clearly intent on giving this lucky boy the fuck of his life.
After a time, as I knew she would, she pushed me back and grabbed the back of the couch, enabling her to raise and lower herself on my hard teenage tube.
This was where, following Dad's advice, I benefitted from my rearrangement of the cushions on the couch. The angle was perfect.
As she lifted herself up and down, her big tits swayed in front of my face, enabling my mouth to catch her nipple flesh. At the same time, my hands could grasp her ass, my fingers slipping now and again to snap a garter strap or intertwine with the elastic at the top of those delicious stockings.
The fact that I'd contrived the perfect fuck position was not lost on her. "So you naughty boy, you've got Mommy just where you want her," she whispered breathlessly, as she lifted herself to the tip of my penis, then impaled herself hard, raking down my tender man meat.
I could tell by her hard movements that she was loving being filled by a far larger cock than she'd ever previously encountered
"You've always wanted Mommy to fuck you, haven't you!" She used the back of the couch to lever her body up and down.
"You've always wanted Mommy to ride you with her tits in your face, haven't you, you dirty horny little bastard."
The "mommy" talk affected both of us and with that last accurate statement, her lovely face contorted into a snarl as she started to orgasm. Her cunt muscles gripped my tender love stick as she moved up and down and I felt my orgasm commence.
She didn't hold back. As she orgasmed, she began riding me frantically, harder and harder.
I cried aloud "FUCK ME MOMMY!" and sucked frantically on her teats, as I sent pulsing spasms of spurting cum inside her. She didn't let up, as my orgasm continued, she rode my love stick even harder as both our bodies shuddered together.
As we finished, she lightly kissed me on the cheek before grabbing her skirt and underwear and going upstairs to her room. In her hurry to leave me, she had left her bag in the hall. I strolled over to it and opened it. Inside I found two emerald green velvet cords. They could have been for her to tie Julian's wrists to the bedrail, but I knew from Dad's notes that the intention was the other way around. Removing them, I hurried upstairs to my own room to bed.
-------------
On Sunday morning I waited for Mommy to have her shower. When she stepped back into the bedroom with a large bath towel wrapped around her, she found me waiting for her.
Even without makeup, with her hair wet and tousled, she looked lovely.
I was standing there completely naked, which appeared to cause her no surprise. I suppose she would have felt that any barriers between us were removed the previous evening with our physical activity.
When I stepped up to her and unwrapped the towel, she knew I was going to kiss her and opened her mouth invitingly.
As we kissed, I maneuvered her to the bed and pushed her back. She was accepting of this until I started tying her left wrist to the bedrail.
"WHAT THE FUCK ARE YOU DOING!" she screamed.
"Now, now Mommy," I murmured reassuringly, "you know you want me to do this. That is why you left the cords in your handbag for me to find."
"STOP IT NOW, YOU LITTLE BASTARD! she shrieked, as I finished tying her other wrist to the bedrail.
She was writhing frantically underneath me as I grabbed and sucked her tits. My boner was hard as a rock, stimulated by the frenzied movements of this mommy in bondage.
"I demand you untie me now," she said in a calmer but shaky voice, while at the same time continuing to wriggle and trying to throw me off her.
I slipped my hand between her legs and massaged a clitoris that I could feel was sopping wet. Although her voice was saying, "NO," her enslaved body was shouting, "FUCK ME NOW!"
I'd intended to loosen her up with some oral ministration, but I decided to postpone the pussy licking until later in the day, as I couldn't wait to fuck her.
Spreading her legs, I thrust my hot meaty organ deep into her. It entered her like a hot knife into butter. Mommy responded by thrusting hard back at me.
I couldn't believe it. Dad's notes had advised me that bondage would turn Mommy into a nymphomaniac, but I never expected her to be like a sexual animal.
I greedily guzzled her teats, squeezing her big breasts which caused her to thrust up at me even more.
I leaned forward and kissed her. She sucked my tongue into her mouth and then voraciously thrust her tongue into mine. All the time we were fucking hard and fast.
When she came it was too much for me. Her cunt gripped my shaft, detonating my orgasm. My cum blasted into her as her breathing deteriorated into orgasmic heaves of breath. Her vagina refused to let me go, milking every last drop of my jizz.
When I untied her, we both lay there exhausted in silence until Mommy said, "That was great!"
After that we had breakfast together and chatted in a more relaxed and friendly way than we had done for years. After breakfast we returned to her bedroom and lay naked on the bed together.
Although it was difficult, I decided that now was probably the best time to tell her that she would be receiving a monthly allowance, rather than a lump sum.
It went a lot better then I'd feared. She said, "I had a feeling that it would be difficult for you to release so much capital at once."
I breathed a sigh of relief at the good news and then felt even better when she said, "And I suppose you'll be staying here and fucking Mommy whenever you want, with your magnificent phallus."
The way she said it indicated to me that the continuation of our sexual relations would not be unwelcome to her. After all those tough years growing up with her, it was still hard for me to like her, but it was difficult to hate a female who has just complimented me on the size of my penis.We discussed many things, including Cynthia, who would be coming to stay the following day. Mommy was complaining bitterly about her.
Apparently, all had changed when Cynthia realized that Mommy wouldn't have much money. Their everlasting friendship seemed to end overnight and now Mommy hated the idea of having to see Cynthia at all. "I now realize she had no intention of inviting me to New York," she said resentfully.
Then, suddenly brightening up, she said, "I hope you're going to get sexual payments from her, as you're now getting from me. I know you've always had the hots for her." As she said that last telling phrase, her fingers of one hand started lightly playing with my member.
I was embarrassed by the suggestion that I fancied my sister, but only said, "I would never be able to get her to agree to anything."
"Your sister used to tell me everything. She is not as experienced as you think," said Mommy and went on to explain:
"Even when Cynthia was at school, her breasts were big for her age. However, her nipples were even larger than you'd expect for breasts that size. More than that, all nipples are erogenous zones, but Cynthia's are ultra-sensitive.
She discovered it the first time she allowed a boy to get his hands under her bra. She couldn't control herself and found she was trying to rip his pants off when your dad came home earlier than expected and Cynthia and the boy had to pull themselves together. She never allowed a boy passed what she called "first base" again."
"She's not a virgin now of course. She lost her virginity to an old rich guy in Paris. She said it was a half-hearted affair. He didn't even take her bra off so intent was he in fucking her. I don't think the sex was up to much and she hasn't had sex since. She says she's saving herself for some unmarried rich New York stock broker. She must be sex-starved at the moment."
Her idle fingers playing with my penis had caused it to thicken up again.
"I'll tell you what," she said conspiratorially, "I'll persuade her the first day that she can get some of what she wants by giving you a handjob."
She continued, "The second day I'll up the ante to a blowjob."
"The third and final day we'll get her to give you a blowjob, but naked. It'll be up to you then to get her to a fuck position. Once she wriggling underneath you, impaled on your big boner, she'll be begging for mercy. Do you agree with the plan?"
I groaned as my ejaculation sent a jet of cum in the air. The combined effect of Mommy's gentle finger ministrations and the thought of fucking my sister had been too much for me.
"Guess that's a "Yes" then," said Mommy smiling.
In the evening, to show my appreciation for the plan, I decided that it was time I gave something to Mommy. She lay back on the bed, smiling with her legs open, as I went to work with some oral pleasing.
With my nose buried in her light curly ginger pubic hair, licking her clitoris and sucking the little organ, I soon had her juices running.
I slurped happily as I attacked her genitalia with my tongue. Moving her labia lips aside with my lips, my tongue rasped her clitoris hard and I forced my tongue into her vagina.
Soon Mommy was mashing her sex organs against my mouth and I felt a sense of unselfishness as her orgasm engulfed her.
However, her sexual moaning had had the effect of re-engorging my penis.
Reaching again for the cords, I tied her hands to the bedrail, this time with no objection. I had her in a doggie position with her ass in the air and she expected normal sex, but then realized my other intentions as I began working her sphincter with my oiled fingers.
Mommy cried out, "Oh no, you're going to fuck Mommy in the ass you teenage brute!"
I thought this was a bit over-melodramatic even for her. I knew from Dad's notes that she was no anal virgin and pretty soon I was fucking her in between her buttocks.
"FUCK MOMMY IN THE ASS YOU HORNY BASTARD!" she cried as she relished my hard thrusting into her anal sheath.
She was loving it, thrusting back at me. I grabbed her auburn hair and pulled it back painfully which made her thrust back even more.
In the end I stopped moving my hips. I just held her hair as she impaled her asshole back onto my boner until I could stand it no longer and my cum exploded sending jizz spurting up her ass.
She was orgasming as I finished and I reached around her to squeeze a nipple and massage her clitoris as she shuddered to her climax.
-------------
The following day, Cynthia arrived. She looked more gorgeous than ever.
She was dressed in jeans that emphasized her great ass and a loose-fitting t-shirt that failed to hide her breasts that had clearly grown even bigger over the last two years. Her blonde hair was cut short which allowed her big blue eyes to dazzle.
"Hi Billy," she said with a half-smile. "I really just want to check that everything is OK for my University studies."
She had hit the key point immediately and I took a deep breath before I gave her my answer.
"Yes and no," I said ambiguously. She looked concerned.
"You're my sister and I certainly intend that you must go to University. However, I haven't quite worked out the finances yet and I think you'll need to work for a year first. I'm pretty certain I can afford to pay for all your University fees at that point. Of course, it will have to be a local cheap University so that the fees are manageable."
"WHAT!" She looked daggers at me. If looks could kill my death would have been immediate and painful.
"YOU FUCKING MISER!" she screamed at me, then stormed out of the room.
Mommy winked at me and followed her.
Two hours later, I had pretended to leave the house, but in reality had sneaked round the back, as arranged, so I could hear their conversation through an open window.
Cynthia had obviously been largely calmed down.
"Alright Mommy," I could hear her saying, "so what do I need to do?"
"Look," said Mommy, "you know your brother has always had the hots for you."
"I know nothing of the kind," said Cynthia indignantly.
Mommy laughed. "Well I remember poor Billy refusing to get out of the pool. You were standing in a bikini between the pool and the picnic lunch. You and I both knew that he had a big erection that he was scared we'd see. Your dad couldn't understand why Billy wasn't hungry, but you knew you were causing it and you continued to stand there."
Cynthia laughed, "We'll I suppose I knew."
I seethed. I remembered clearly that humiliation and the fact I was starving of hunger. What I hadn't realized was that Cynthia had done it on purpose.
Mommy continued, "Just use your brains. A little handjob will take you a long way."
Cynthia was aghast at the thought of giving me a handjob, having to touch my cock, but Mommy continued to work on her. After another half an hour I knew what to expect.
That night I was in my room just in my boxers. It was another warm night and I was about to open the window a little wider when Cynthia knocked on the door.
As I said, "Come in," Cynthia opened the door and walked in, carrying a box of tissues. She had on a blue baby doll nightie that immediate sent my cock into full boner mode.
"Billy," she said in a low voice, "I'm so sorry I shouted at you. I know that managing the finances is not easy, but I do so want to go to University this autumn. Is there anything I can do to help you reconsider?"
I knew from my overheard conversation that this was a speech worked out between the two women. I was also expecting her next action which was to place her hand against the bulge in my boxers.
I decided to play the daft boy. Gulping in feigned surprise I whispered, "I don't know what you mean."
Cynthia looked gorgeous as she bit her lip in annoyance, grasped my boner harder in my boxers and said, "My fingers can be nice to you if you're nice about my University start date."
I looked at her and gasped, "OK!"
Pulling down my boxers, I stepped out of them as she said, "but don't touch me."
As she brought her hands around my boner she gasped and stared in surprise at its size. She didn't say anything, but just started jacking me off.
Her cool fingers felt delicious round my hot man meat as she said reassuringly, "Just relax, you're going to enjoy this."
I had the impression she'd never done this before and was relieved that Mommy had at least told her about the importance of the helmet, otherwise I think we would have been there all night.
She started making comments in a way that suggested further coaching by Mommy. "You like your sister's fingers round your cock, don't you Billy?"
"Oh yes!" I groaned.
"I bet you've always fantasized about your sister jacking you off, haven't you Billy?"
After a couple of minutes she found that by concentrating solely on my helmet, she had me groaning continually. She was getting good at this, so much so that my orgasm erupted with hot jets of cum spurting all down the front of her baby doll nightie.
She shouted, "Uuuurgh!" and tried to hold my cock away but only succeeded in receiving a gob of cum in her face.
Jumping back, she staggered out into the bathroom.
Ten minutes later Cynthia reappeared round my door wearing a clean pink baby doll nightie and a very tight smile. "Why didn't you tell me you were cumming?" she asked through clenched teeth.
"I didn't know I was supposed to." I explained looking very naïve.
"OK," she said with a heavy sigh, "Good night Billy," and grabbing the unused box of tissues she walked back to her room.
-------------
The following morning at breakfast, with the three of us sat around the table, I said to Cynthia in a voice which I hoped conveyed that I had spent a lot of time considering the matter, "A University start date of this September is fine."
She looked pleased until I added, "at a local University of course."
There was silence round the table until Mommy winked at Cynthia, then put her hand on Cynthia's and said, "I want to talk to you about a few things later, Cynthia."
Cynthia looked mollified by this and we carried on in silence until I walked out.
An hour later, I had again pretended to leave the house, but in reality had sneaked round the back to listen in.
Mommy was sounding very reassuring, "So, that's great, last night you were obviously very persuasive, but clearly you will need to go further for New York. It has to be a blowjob."
"WHAT! YUK!" Cynthia was clearly not impressed with the suggestion. "He might cum in my mouth."
I could imagine the look of disgust on poor Cynthia's face.
"Nonsense," said Mommy, "you just need to be more careful than last night and tell him to tell you when he's cumming."
"Anyway," said Cynthia, with desperation in her voice, "he's huge. It's not natural."
"Do you mean he's got a big cock?" said Mommy with a half-laugh.
"No," said Cynthia in a loud voice, "he's got a very, very big cock."
"Alright, calm down," said Mommy soothingly, "you don't have to swallow his whole cock. Just concentrate on the knob bit at the end. It's really the only part that matters."
The conversation continued with Cynthia raising objections and Mommy encouraging her to think about it, until it finished with Cynthia saying, "Ok, I'll give it a go."
That evening was a repeat of the previous evening with Cynthia knocking on my door, then entering. She was wearing the pink baby doll nightie that she had changed into after I had ruined the blue one. She was again carrying a box of tissues.
As she approached me she said in a low voice, "I really want to go to New York. Please consider it."
As she said it, she put her hands down to grasp my cock again through my boxers, but this time I took a step back and held my hands up.
"No, Cynthia," I said in a voice that I hope conveyed reluctance, "I know what you're offering to do, but the New York course is just too expensive."
Cynthia stepped forward after me and firmly grasped my boner. "What if I were to use my mouth," she hissed.
I looked astonished and flummoxed as I responded, "Gosh, well I don't know."
I then took a deep breath and said, "Well I suppose I could look at the figures."
Cynthia smiled as she lowered my boxers, but said in a slightly steely voice, "Good, but remember, you mustn't touch me and for God's sake this time tell me when you are cumming."
She pushed me until I was sitting at the end of the bed and knelt in front of me.
"I certainly will," I gasped, as her melting mouth opened and sucked in my helmet.
Oh fuck, this was heaven. She didn't have Mommy's subtleties of using her tongue, or of grasping my balls, but to have achieved a lifelong ambition of being sucked off by my sister was ecstasy.
Following Mommy's instructions, she concentrated on the mushroom head. Her lips slid backwards and forwards over the head to the rim and back to the red eye at the very tip.
She may not have done a blowjob before but she learnt very quickly. The rhythm was just the right pace, not too fast and not too slow. The pressure of her lip sucking was perfect.
My boner seemed to grow in her mouth as her sensational sucking of my glans was bringing me to a higher and higher peak.
I had to fight hard to stop myself from grabbing her head and fucking her mouth fiercely.
Suddenly I could hold back no longer. I felt my jizz surging up my cock and into her mouth. Unaware, she carried on sucking me as spurt after spurt jetted out.
After about the third spurt I groaned, "Sister, I'm cumming!"
Too late, she dragged my cock out of her lips. A rope of cum spurted onto her face as she exclaimed,"Aaargh, that's disgusting!"
I could see her clean nightie covered with cum stains as she rushed to the bathroom and I could hear her retching in the sink as she frantically washed my cum out of her mouth.
Half an hour later a clearly annoyed Cynthia stepped back into my room, with yet another clean baby doll nightie, this time green, trying to preserve a half-friendly face. "You never told me you were cumming!" she spat out.
"But I did," I said, with a hurt demeanor, "when I was cumming I told you I was."
"You were supposed to say it before you were cumming." she hissed, trying not to lose her temper. She didn't want to upset me after what she'd been through to gain my approval to New York.
"Well, you didn't say that," I said, with a hurt look.
We both said "goodnight" as she closed my door carrying the box of tissues.
-------------
The next morning I was just finishing my breakfast when Cynthia joined me. She looked at me expectantly with a questioning expression on her face.
"Look Cynthia," I said in a serious tone, "New York is very expensive."
"You promised to look at it," she said with a hard tone.
"I have," I said, "but I could only afford to pay for you in New York if I sacrificed other important things."
I was hoping she wouldn't ask me what important things I was referring to, and she didn't.
"Does what I did for you count for nothing," she said, contriving to sound hurt. "You know I did it because I love you."
"If you loved me," I said directly at her, "you would be naked when you sucked me. We would also kiss each other lovingly beforehand, like other boys and girls do."
She looked quizzically at me and asked in a hard tone, "Would you agree to New York if I was to do that?"
"It would certainly make my sacrifices more worthwhile if I can come to your room tonight on that basis," I said as I walked out of the room.
An hour later I was listening to Mommy and Cynthia again.
"What if he tried to touch my breasts?" Cynthia was asking.
I could hear Mommy's response, "You could keep your hands over them while you blow him. When you're kissing, you could hold them then as well. If he's like most men, his hands will be grabbing your ass."
"He could go berserk," Cynthia said with a worried tone.
"You're joking," said Mommy, "Billy wouldn't have the nerve. Anyway, your room is next to mine. At the first hint of trouble that you can't handle, all you need to do is call for me and I'll burst straight in."
"That's true," said Cynthia reassured. Then with a laugh in her voice she said, "Hey, it looks like I'm going to New York after all."
"And I'll be able to visit you," said Mommy.
Cynthia suddenly sounded reluctant, "Well not in the first semester of course, but after that who knows."
Although I couldn't see her face, I could feel Mommy seething.
Later in evening I prepared myself. I put on my boxers, then applied oil to the front of my legs. Not enough so that they glistened, but sufficiently to give them a slippery quality.
Leaving my room, I was on my way to my sister's bedroom, when Mommy stepped out of her room, put a hand on my arm and whispered, "She's still a bitch. I want to hear her screaming."
I knocked on my sister's bedroom door to hear a confident command of "Come in."
As I entered, I could see the underused box of tissues on the side of the bed. Cynthia was standing there looking at me. She had on the clean green baby doll nightie from the end of the previous night. She clearly intended that it would stay clean as she said, "Promise me that you will not cum in my mouth."
"I swear I will not cum in your mouth," I said in the formal voice of a courtroom witness, knowing my intention was to cum in another orifice entirely.
She was looking gorgeous. Her blonde hair fringe was just above her big baby blue eyes. Her luscious lips were slightly pursed as if she was about to do something that was necessary but slightly distasteful.
She turned to face the other way as she lifted the nightie up over her head, just leaving herself in a pair of matching green satin panties. My mouth went dry as she carefully peeled these down exposing her magnificent bubble butt.
She turned round with her hands covering her breasts. Even so the sides of her full breasts peeped out around her hands. She had a light covering of blonde pubic hair that drew the eye at the top of her long legs. As she slowly walked towards me I backed away, as if very shy, until my back was against a set of drawers.
She stopped in front of me and, still clutching her breasts, awkwardly leaned forward to execute the kiss we'd agreed on.
I whispered, "Congratulations, you're going to New York", then reached my hands around and grasped her delicious bubble butt, pulling her into me. My oiled left leg slipped between her legs, separating them and I could feel her genitalia on my leg.
She gasped, feeling mixed emotions. She must have been feeling elation at my words of confirmation of New York but concern at her position on my leg. She would have thought that it was the warm evening that had caused my leg to slip between hers. Having now secured her success she would not want to rock the boat by complaining about our kissing position.
Because she was holding her breasts, it created a space between us so that my boner was not pressing against her. This, combined with the fact that at this stage I was careful not to try and rub her sex, persuaded her to continue to join in our kiss.
If she hadn't had much experience of blowjobs, she was certainly experienced in kissing. Her wriggling tongue explored my mouth, licking the sensitive areas. She sucked my tongue into her mouth and teased it with her own tongue.
She was concentrating so much on fulfilling my oral requirements that she didn't notice as I began to pull her buttocks backwards and forwards. Slowly but surely I felt a gradual moistening of her sex, until with a start she came to and pulled back from me.
With stage one over; we walked together towards the bed. She was still grasping her breasts and I wondered if she'd considered how she was going to manage the tissues when I ejaculated with the blowjob. In the event I would never know, as instead of sitting on the bed I pushed her down on it and fell on top of her.
"One more kiss sister, please one more kiss," I begged as she lay stunned underneath me.
Thinking that I just wanted another kiss, struggling to get up she turned her mouth away and said in a steady voice, "No Billy, let's move on."
What she hadn't noticed was that as we collapsed on the bed, both my legs had slipped between hers. However, as I went quiet she suddenly realized that her legs were either side of mine. She reacted immediately gripping her legs and knees together as tightly as possible.
Then with horror she began to realize that I was wriggling and moving on top of her, not to try and kiss her, but to maneuver my pelvis.
At first, thinking it was an unthinking action of a normal boy, she started gasping, "No Billy."
Then she could feel my boner inching towards her opening. She started crying, "NO! NO! NO!"
Her hands left her chest and started to push me hard to force me off. "MOMMY!" she screamed.
Her big full tits were now exposed to me for the first time. Her areolae were like large pink fruits at the end of her melons. Her nipples were not outlined, but I was certainly going to find them. Her tits wobbled and jiggled as she wrestled to free herself.
The feel of the tip of my boner touching the edge of her pussy lips was electric, both to her and me. She squeezed her legs tighter and tighter as she screamed again,"MOMMY!"
Although her legs were gripping me as tight as they could, they were fairly powerless to stop my oiled legs pushing them slightly further apart as my burning helmet nudged at the opening.
Every breath now was a scream of "MOMMY!"
Her pussy, which was already moist from my leg massage, was being excited from the heat of my glans and began unwillingly seeping juices..
"NOOOOO!" a cry of horror came from her as I pushed forward piercing her entrance.
Her legs were still gripping me, impeding my movement, but with each push I gradually was able to nudge another inch of my hard man meat inside her tight juicy cunt.
She was staring fixedly ahead. Her look was aghast as she must have been wondering where the hell Mommy was.
As I kept inching further inside her I whispered, "Remember my cock is not big, it's very, very big."
Her big blue eyes went even wider in horror as she realized I was repeating her own words and then she screamed again as I bent my head down to her right tit.
Her thrusting arms had become weaker as they had struggled and I was able to thrust them aside as I used my fingers to help push her areola into my mouth. Her nipple immediate burst into an inch of chewy rubbery flesh. I sucked and guzzled it, then transferred my mouth to her other tit, slobbering over the teat with the same enthusiasm.
Cynthia had been groaning loudly as I'd ravished her breasts. The juices in her genitals had started flowing freely and, as I'd been suckling her teats, my boner had slid further up her vagina so that it was now fully in to the hilt.
I pulled it back and thrust it in deep as hard as I could. Cynthia blew her breath out with an "Ooooh!"
With that hard thrust, her legs, which had been gradually loosening their grip, now relaxed completely. I pushed them back, opening up her pussy to the utmost.
Cynthia groaned as she realized I could now ride her as hard as I liked.
I started a steady fuck rhythm, "Thock - Thock - Thock - Thock."
She was starting to whimper as I enjoyed the grip of her tight juicy cunt as I thumped my hard hot meaty salami into her.
Letting go her legs, I squeezed a tit in each hand as I continued my pumping. Now her legs were free, she could move her pelvis which she started to push up in time with my thrusts.
Mocking her I said, "Glad to see you're enjoying it, Sister,"
I could see the utter dismay in her eyes that her body was betraying her.
"YOU BASTARD!" she groaned, pumping her hips, horrified that she could not stop her body responding to her horny little brother, who's organ was tightly packing her vagina.
Pretty soon her thrusts up were becoming frantic as she started orgasming.
Her eyes were watering with frustration as her vagina muscles gripped my boner in her spasms.
This was too soon for me. I gripped her legs again and pushed them even wider as I speeded up and began to really hammer into her, "ThockaThockaThocka".
I was fucking my sister with venom as I ejaculated and sent strong spurts of cum deep into her. Finally I collapsed on top of her.
However, my sister was still unfinished and as I lay there I could feel her cunt automatically still squeezing my member. I hadn't deflated and soon I was I fully firm again and we were both fucking each other hard. In fact now my sister seemed to be more desperate than ever.
Utilizing her cock craving, I pulled her over so that she was now impaled on top of me. While she was momentarily bewildered, I leant forward and grabbed a buttock in each hand. I had only moved her backwards and forwards once when she took up the rhythm, forcibly grinding her pubes into mine.
Soon she decided this was not enough and began lifting herself up and down.
I slipped a hand under each buttock and as she lifted herself up I held her there. I was preventing her from impaling herself. Although with her weight she could push down a bit, I lowered my pelvis each time she did.
"You like brother's boner in you sister, don't you," I taunted. She just moaned with closed eyes.
"What do you like?" I teased. As I asked the question I tormented her with little movements of my cock at the edge of her pussy lips.
"BROTHER'S BONER!" she screamed.
As I let go her ass, she rammed her vagina down onto my hard young cock.
She leant forward and grasped the bedhead to give herself leverage, then began savagely sawing herself up and down my rigid love lolly. As she was fucking me, her eyes were watering with shame and hatred.
I linked my hands behind my head to emphasize to her that she was doing all the fucking, knowing there was no way she could stop.
I could see she was heading for an even bigger orgasm than her first one and as she slammed down on me she shrieked, "I HATE YOU, YOU FUCKING BASTARD!"
Just to make her feel even more mortified, I gasped "I am going to shoot all my cum inside you, Cynthia!"
I then started gobbling her teats which seemed to push her over the edge as she crashed down on my hard root for the last time and began spasming.
My orgasm seemed my strongest yet as my big boner sent strong pulses of cum jetting inside her. Her cunt was milking me, sucking my hard tender meat.
We both lay there for a minute exhausted, before I pushed her off and returned to my room.
-------------
The next morning I went down to breakfast to hear the two women arguing.
"I'm sorry Cynthia," Mommy was saying, "I must have taken two sleeping pills by accident."
As I entered, they both stopped talking and looked at me. Cynthia must have been fearful that everything was a con and that there would be no New York.
"OK Cynthia," I said in my best businesslike manner. "I've agreed with your University to pay for the Fall semester. I've also agreed rental terms with your New York apartment agent based on a month's notice.
Cynthia looked stunned. "But the University requires the Fall and Spring semesters to be paid up front and the apartment was a year's rent in advance.
"I fixed it all up before you arrived Cynthia," I explained. "The University was sympathetic over Dad's death and, in the circumstances, agreed to payment for just the one semester. And the apartment agent was looking to set up a real estate business in Boston. Well Dad had some connections in Boston, which I was able to use for the agent's benefit, hence the one month's notice."
Cynthia clearly didn't know what to think. She was pleased she was going to University where she wanted. She was pleased that she had the apartment she wanted. She now understood that I'd agreed it even before she'd arrived and that I'd just been tormenting her to enable me to have sex with her. But why the funding was effectively only for the first semester she didn't understand until I made it clear.
"You will come back here for the Christmas holidays of course. And we will have to see how you behave before I make my decision in terms of funding for the Spring semester and continuing the rent for the apartment."
Cynthia left the house quickly and quietly. Mommy explained that she was in a rush to obtain the "Morning After" pill and it made me think that I'd better get the contraception sorted as soon as she came home for Christmas.
Mommy wanted to know all the details of the previous night. She told me that she had been masturbating furiously as she listened to my sister's screams.
Later in the afternoon, Mommy and I were having a session in the office. Mommy was in full Christina Hendricks mode and I had her on the shiny desk. She was stripped except for her garter belt and her stockinged legs which were over my shoulders.
I had a hand grasping each thigh above her stocking tops with her garter straps biting into the backs of my fingers. I was pulling her towards me as I thrust into her and started planning my Christmas present to myself which I'd decided to be my sister's anal cherry.
With these thoughts of a wonderful family Christmas, I orgasmed happily spurting my cum inside my beautiful Mommy.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.
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 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 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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