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Mom & Aunt both Want to Win

123

The conversation on the Sunday night eventually turned to sex. What else would you expect from a dormitory full of twelve horny eighteen year-old schoolboys. But before that inevitable change, I had introduced the topic of voluntary work. The Head of School, Mr. Preston, had asked for volunteers at the morning assembly to help in painting and renovating a Day Care Services Center for a day and I had suggested to the guys that it was something we could all do together. That suggestion fell extremely flat so, giving up, I joined in the usual discussions about the women at the school.

As the Galton Faith Academy was an all-boys private school, the women were few, but there were two used for fantasy jacking off. These were the school nurse, who happened to be my aunt and who used to be the partner of Mr. Preston, and his personal secretary, who was his new partner.

My aunt was a voluptuous forty year-old with big tits projecting forward and a nicely rounded athletic ass sticking out behind her. Her surprisingly slim waist accentuated her curves. Her facial features were attractive and exposed by her light brown hair being pinned back in a French bun.

Although my aunt was attractive, she did not have the saucy enticing smile of the young lithe personal secretary, whom Mr. Preston couldn't resist. Consequently my aunt had moved out of the family home into an apartment near the school. Both women had all of us boys continually jacking off, but it was my aunt who was my favorite.

"I'd love to fuck her in the ass!" I groaned.

At that all the boys moaned in agreement and Patrick, my best friend, said with a laugh, "Well if you manage to fuck Nurse Hudson in the ass, we'll all spend a day painting that Day Care Services Center."

Even I laughed at that offer.

I was friends with all the boys in the dormitory. Unlike me, they were all from military families with either a single parent or both parents in the military. Most boys in similar positions had gone to a Military Academy, but these guys had chosen a non-military education. They mostly aspired to be bankers. We had all been at the preparatory school for three years. Now we were all eighteen, haven't finished our twelfth grades and were just killing time until we went to university. We would all be gone within a couple of weeks. I would be one of the first to leave as I would be returning home the following Saturday to stay with my mom, while I did my three-year degree at the local university. The other guys were all leaving the following Saturday. We had all done well in our exams but it was despite the school, not because of it.

On the Monday, the following morning, I was due to see dad's lawyer, Mr. Phipps, who had also been dad's financial adviser. Dad had died four years ago and had arranged for me to attend Galton Faith Academy as a boarder when one of his old friends was the Head of School. Unfortunately the friend died soon after dad and the prepaid arrangement couldn't be undone. I would now be seeing Mr. Phipps to see what financial arrangements had been made for my university education.

The next morning I was welcomed by Mr. Phipps into his office. He made sure I was comfortable before he started explaining the position.

"Well Jack, as you know your father paid a considerable sum to the Galton Faith Academy for your fees and accommodation, far more than he had to. No doubt they passed some of the excess to you while you were there?"

"Not a cent." I replied with a shrug. Mom had been my only source of pocket money all the time I'd been there.

"Oh!" he looked surprised, but carried on explaining.

"For your university years, apart from providing for your fees etc., your father set up an investment fund which, I have to say, has been invested miraculously profitably. The total stands at half a million dollars. The fund will be paid to whoever you nominate as the provider of your accommodation. Strangely, the money is to be paid up front as soon as you have signed the contract. This means that in theory the provider could renege on what they have promised to you and provide very little. I guess that because your father assumed that you would be choosing to stay with your mother, he had no need to place any conditions on the money.

"I will of course be staying with my mom," I said.

Mr. Phipps beamed, "I knew you would be saying that. After all, with you going to Seattle U, First Hill is not far from your home. I know your mother is looking forward to you returning home. I have already told her about this money and she intends to give practically all of it to your father's foundation. I have here the papers now for you to sign in her favor if you wish."

He pushed a paper for signature towards me and I scribbled my autograph across it immediately. As soon as Mr. Phipps had mentioned the money, I had felt sure that mom would be giving it to dad's foundation. It was the charitable organization that I intended to take a lead part in myself, when I had finished university.

Mr. Phipps suddenly looked serious. "I'd better tell you that, because of the initial way your father set things up, your Head of School, Mr. Preston, also has electronic copies of these papers and is aware of the value of the fund. A silly idea did occur to me that, given the sums involved, he might even try to persuade you to stay on at the school premises, but now you've signed this, that is the end of the matter."

Mr. Phipps relaxed back in his chair with a smile. "I'll just let your mother know you've signed the papers. I know she'll be pleased."

"No," I replied. "I'd like to tell her myself when I visit her next Saturday, which will now be my effective returning home day."

"Of course," Mr. Phipps nodded his head in acceptance.

As I started my walk back towards the school, I thought about my mom and my aunt, her sister. They had both been in competition for dad when they were teenagers. My mom had won and my aunt had hated her ever since. At thirty eight, my mom was two years younger than my aunt. They both had the same light brown hair color. My aunt was attractive but my mom was beautiful with a figure that if anything was more curved and voluptuous than my aunt's.

I had really been looking forward to moving back in with mom and had stayed with her a few weekends in the past year. She was very affectionate and was always hugging me and telling me how she loved me. Each time I met her I would be eager to tell her my news, but as soon as we stepped up to each other she would say "kiss me" and I had to give her a peck on the lips before I was allowed to continue.

One time, however, I had made a terrible mistake. As I lay in my bed at mom's I had some pages from a porn magazine that I kept in an unobtrusive folder. Inside were my three favorite porn pages. The first was a picture of an older woman in her white underwear, which consisted of the traditional porn clothing of bra, bikini panties and garter belt. The straps of the garter belt were attached to tan stockings, and high heels completed the outfit. In the picture was a nude young guy, who looked like a teenage boy, lying back on a bed. The woman was between his legs fellating him. Above the picture I had written the caption in bold letters 'Naughty boy forces mommy to suck him off'. On the next page the bra and panties were gone and the woman was clad only in stockings, garter belt and high heels. On this page she was straddling the young man, fucking him. Her beautiful big juggs, which had not been so obvious on the first page, were on full display. The caption I had written read 'Naughty boy makes mommy ride him'. On the last page the woman was kneeling on the bed holding the handrail while the boy's penis was clearly in her ass. My caption read 'Naughty boy punishes mommy'. There were a number of my cum stains on the pages but not enough to spoil my viewing.

I had placed the folder in my bedroom drawer but unfortunately forgot to pack it in my bag to take it back to school. I thought nothing of my mistake as I knew mom would not be going into my drawers. The next time I was home, mom greeted me as usual expecting me to give her a kiss before we talked. However, when I went into my bedroom I realized with horror that the drawers had been replaced. My folder was in the new drawers, which meant that mom would have had to move it.

My mouth was dry as I went down to the lounge, but mom just smiled and hugged me again. I realized with relief that clearly she had not looked in the folder and I sat down trying with difficulty to compose myself.

As I arrived back at the school from my trip to dad's lawyer, I was greeted by Mr. Preston who, smilingly, guided me into his office.

"Hello Jack, I just wanted a chat about your next move."

As I entered his office, I noticed that my aunt was seated there waiting for me.

"Now Jack," he said as he continued smiling. "I know you've just been updated by your father's lawyer on your options and you're probably planning to live with your mother, but I just wanted you to consider staying on here. Your aunt would obviously be delighted with that arrangement."

He'd raised a hand towards my aunt as if pointing her out to me. I smiled inwardly as I knew that she hated me.

He continued, "You know about the money, a considerable sum. That would be embarrassing for us given our current very profitable situation, but fortunately it would be mostly used by the school's charitable trust. Clearly you won't be in a dormitory, but from now on will be in here."

As he had been speaking he had led me outside his office to the next room and gently pushed me through the doorway. The room looked expensively furnished. There was a large 3d television screen on one wall. In the corner was a small fridge. A laptop, which I knew to be top of the range, sat on the desk. It must have all cost a fortune. Then on the bed I saw the Intermec cell phone. I knew it had a range of features including great video recording.

"You will have free access to all our library facilities as well. We'll keep the fridge stocked with beer of course. Please don't make a decision now," Mr. Preston said quickly. "You will need to have your 'end of school' medical by Nurse Hudson," he smiled, "your aunt, this afternoon, so I hope to hear your decision after that."

He turned abruptly and went back into his office. My aunt just said to me with a taut smile before she followed him, "Come to my surgery at three o'clock."

As she closed the door I sat down on the bed bewildered. I hadn't dared to tell them that I had already signed the papers in favor of mom. I decided to leave the laptop alone, but I was eager to register my Intermec cell phone, which I quickly did. I tried taking a video in the room. The picture quality was superb. I was feeling warm and was about to open a window when I saw an air vent in the wall. I opened it up, but instead of a blast of fresh air I felt nothing. It was only then that I realized it was not an outside wall, but the wall separating Mr. Preston's office and my room. I could see that the vent was shut his side. I could not see into his room but I could clearly hear all the conversation.

Mr. Preston was evidently addressing my aunt. "This has got to work," he hissed. "We have to have the money to cover our current deficit. We've made huge losses this year."

My aunt sounded sarcastic in her reply, "Well you shouldn't have spent so much money on your floozy."

Mr. Preston ignored her comment as she continued, "and the cost of the equipment you've provided for Jack is ludicrous."

"It's all on loan," he replied, "It's going back in a couple of weeks, when he's signed the papers. Anyway, remember you'll be getting fifty thousand dollars for your role in this. Your medical checkup had better be good. I need to go away for a few days and when I'm back I'll expect him to have signed the papers in our favor."

"Don't worry about me dear," aunt replied sarcastically, "although I hate the little smug bastard, I'll bring him round."

I was extremely puzzled by all this. Although I enjoyed playing with the Intermec cell phone, I had no intention of permanently using any of the equipment. Mr. Preston and auntie were clearly crooks and I felt relieved that I'd already legally committed myself to mom, but how the medical was going to help them I had no idea. I decided that I had to stop this going any further. I wouldn't tell my aunt that I'd already signed in mom's favor, but I would tell her that I'd made up my mind.

At three o'clock I entered Nurse Hudson's surgery. My aunt looked up briefly from her desk and told me to take off my clothes and lie on the couch. As I slowly unbuttoned my shirt I looked around. A bed was made up on one side ready for a possible emergency. In the middle of the room was a massage table on which she evidently intended to examine me. Next to it were various bottles of oils and lotions.

I had taken everything off except my boxers and was moving towards the couch when my aunt stopped my forward movement with, "All of it! I'm a nurse. I've seen it all before you know."

Sheepishly I took off my boxers and tried to stroll confidently to the table. As I walked towards it I said. "Auntie, I need to tell you that I have decided to regretfully decline Mr. Preston's invitation to stay here."

"I see," she said slowly, "well let's get on with your examination."

She was wearing her usual white tunic covering her down to her stockinged legs just below the knee. I was feeling exposed but started to relax more as she went through the usual routine examination of looking at my tongue, looking at my ear drums etc. Everything seemed fine until she started examining the glands at the side of my neck. Pressing in with her fingers she made a sound which conveyed a little concern. I can't say I was worried as I hadn't noticed anything amiss myself, but she continued prodding.

Standing back she asked me to open my legs so that she could examine the glands in my groin. Obediently I opened them slightly, but she prized them further apart. Putting her hand on the lower part of my stomach she slowly slid her fingers down my right groin, easing them between my balls and my leg. Embarrassingly I could feel the heat rising in my cock as it began to thicken. When she then repeated the maneuver down my left groin my cock inflated into a hard erect phallus.

I was flush with embarrassment, but auntie seemed to ignore my problem just saying the glands in my groin seemed OK. She then told me that she needed to check my testicular glands and gently squeezed my balls. My state of excitement was increasing exponentially.

As she squeezed my balls she whispered in a confidential tone, "Your testicles seem heavier than they should be. Do you masturbate regularly?"

"About twice a week," I lied. It was at least four times a day, but I couldn't tell her that.

"Well that's identified your problem then dear," she diagnosed in her continuing confidential whisper, "you need to relieve yourself more often."

I couldn't believe what I was hearing, especially as she suddenly gripped my cock round the base and held it as if measuring its girth.

"I suppose I could help you," she whispered, "but I can't see why I should, when you don't wish to stay with us."

I was getting desperate now for her to continue. "I suppose I could reconsider," I gasped.

Her hand had moved up my cock nearer to my helmet as she smiled and said in a louder voice, "Why that would be wonderful."

Not letting go of my cock in her right hand, she reached out with her left hand for a bottle of lotion and splashed a generous amount over my cock and balls. She then started slowly jacking me, her fingers caressing the mushroom head as her left hand cradled my balls.

"You're very well endowed Jack," she said with a smile and despite the fact that I felt I couldn't trust a word she said, I did believe by her admiring tone that she meant it.

Her fingers felt heavenly as they danced up and down my boner. Whenever I jacked off I had always done it frenetically, but now I could feel the benefit of a slow steady hand.

As she stroked me, auntie had returned to her whispering tone, "You like that Jack, don't you. I bet you've dreamed of me doing this to you. Well if you stayed with the school I would need to give you a medical every week to ensure that your testicles were regularly drained.

"Oooh!" I moaned. I didn't believe she meant a word of what she was promising, but the pleasure she was giving me was indescribable, She hadn't increased the speed of her stroking but she was concentrating now solely on the crown and squeezing it a bit more firmly. I was gripping the table covering with both hands.

I could feel the buildup in my cradled balls as I groaned aloud, "OOoooh I'm cumming Auntie!"

The jizz spurted out through her fingers as she gently squeezed my balls and held my boner. Her fingers had intercepted the cum jetting out too far and the white cream was now covering my stomach. She cleaned me up in silence, but as I dressed she said, "I'll see you for another medical at the same time on Wednesday when you can confirm that you're staying here."

I nodded my acquiescence and walked out to my new room next to Mr. Preston's office.

On Tuesday I fought all day with a troubled conscience and eventually decided that I needed to be mainly honest with my aunt and tell her that I was going home to my mom, even if that meant foregoing a delightful handjob. Consequently, on the Wednesday, as soon as I entered her surgery, I looked my aunt in the eye and said that I would not be staying.

After looking at me seriously, auntie told me to strip off anyway, so she could check me out. This time her fingers went straight to my groin and my boner reacted accordingly. She gently squeezed my balls with her right hand and felt the glands in my neck with her left hand. As she touched me she said in a pained voice. "It's a pity you're not staying. I'd intended to drain you again, but this time holding your testicular glands with my right hand as I felt the glands in your neck with my left hand."

I didn't understand what she was saying. Was she going to put a machine on my erect cock? Then it was clear.

"Of course that would only have left me my mouth to stimulate your penis to orgasm." she said with a voice conveying regret for what might have been.

At that moment I wanted nothing more than for auntie to give me a blowjob and I found myself crying out, "OK then I'll stay here at the school."

Auntie smiled and whispered, "Good boy, I'll print off the papers for you to sign at your next medical on Friday and remember I'll be sucking you off on a weekly basis from now on."

With that promise she closed her luscious red lips around my crown and pushed them down my boner, sliding the mushroom head into her mouth. Her tongue was busy lashing my helmet, pushing into the red eye and licking the rim. Her pretense of touching my neck had gone and the fingers of both her hands were either cradling my balls or gripping the base of my boner. The technique of her wet mouth and tongue were amazing and I found it incredible that Mr. Preston had ditched her for a younger less experienced model.

I was groaning ecstatically, "Oooh that's fucking great auntie."

This time I was not gripping the table as my hands had reached out and were gripping her hair, holding her head as it bobbed determinedly up and down. She started going lower on the downstroke, pushing my helmet down her throat and breathing noisily through her nostrils. Each sliding movement of my boner in her throat sent a spasm of pleasure through my genitals.

Pretty soon I was screaming, "I'mmm cumming!!" as my jets of cum filled her throat and mouth. At that point she concentrated on sucking my helmet hard in her mouth and squeezing my balls in time with my orgasmic spasms. She swallowed every drop and stood back with a triumphant look.

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