I Win the Lottery

Mom shifted above me slightly so that she could make her other nipple available for me. I lightly nibbled it before sucking it completely into my mouth. I couldn't see past my mom but I could hear the slurping sound of my sister licking and sucking my cock. It was a very enjoyable feeling in my boner, made more so by my guzzling of mom's teats.

I knew that my situation was one that most other eighteen-year-old boys would envy. I suppose some might have called me greedy, having both my forty two year-old mom and twenty four year-old sister as my cum sluts, but I didn't care. I thought back happily to when it all started, which was when I won the lottery.

A month previously

The reporter was half smiling as she asked me the question, "Can you believe how lucky you are to be the youngest big lottery winner this state has ever had?"

I smiled back, "Well I guess as I bought the ticket on my eighteenth birthday, I was always going to be the youngest. As to the amount, you're right, I couldn't believe it when I saw the win was over thirty million."

"How are you going to spend it honey?" She seemed to think that it was going to be a problem for me, which it wasn't.

I looked over at my mom and sister, Sophie, who were being interviewed twenty yards away by a reporter from another news station. My sister looked gorgeous, brown hair, a beautiful face and a stacked body. She looked like a lingerie model for the fuller breasted woman. My beautiful brown haired mom was a similar height with a figure that was an exaggeration of my sister's. My sister's tits were big; my mom's were even bigger. My sister's ass was a well formed round butt; my mom's was like two footballs, with a shelf.

Both women had dressed up for the reporters, busting their credit card limits. They were telling the reporters what a close-knit family we were, which I supposed was true to a degree. Neither woman had seemed that interested in me until they had found out that I had won the lottery. Before that point they had both seemed to find me sweet and amusing but neither went out of their way to talk to me. I'd bought the ticket on the first day of my summer school break and I hadn't been expecting to see much of my family during the holidays.

Neither of them had been into work since learning of my win, although I had made plain to them that I had no intention of allowing them to build up huge credit card bills and expecting me to pay them. Dad had left home about the same time as my sister moved out when she was twenty, leaving my mom as the sole payer of the mortgage. However, my sister had to move back in two months ago as she had split from her partner, leaving my sister with debts. Now the two of them obviously thought all financially would be well.

But I was not going to make life easy for them. They had always been spendthrifts. To be fair to them, they were pretty free and easy with me, leaving me alone to play porn to my heart's content in my room. There had been an embarrassing moment a couple of weeks previously when mom decided to tidy my room. She had found a stack of DVDs in my drawers including 'Big sisters and little brothers' and 'Big breasts and stockings'. She had been looking at them with my sister when I came home and caught them laughing. Mom was just showing Sophie the cover of 'Moms ride boys', which pictured a voluptuous older woman, very much like mom, straddling and fucking a teenage boy. I quickly snatched that DVD and all the other embarrassing DVDs off them, pushed them both out of the room and slammed my bedroom door shut.

The male reporter was trying to ask mom and Sophie questions, but seemed unable to drag his eyes away from mom's chest. I could appreciate his problem. I wondered sometimes if mom was aware how much I was staring at her breasts when she wasn't looking.

"So you're looking to spend money on fine wines, Mrs. Gibson. Which of France's wine regions do you think is breast?" he spluttered, "I mean best."

Mom didn't seem to notice his word mix-up and started droning on about the Bordeaux region, which I suspected she'd just read about.

The reporter interviewing me saw me staring at my mom and sister and misread my thoughts, "I can see you're thinking of your family. Jimmy you're a very generous young man," she gushed.

I looked across again at my mom and sister and just replied with a smile, "I certainly intend to share an appropriate amount of my new wealth with them."

However, what I deemed appropriate I knew would seem insufficient to them.

As the reporters and technicians drifted off, mom, sis and I began to walk back to the house. My sister smiled at me.

"Jimmy, I've left our credit card bills on the table in your room. Be a darling and pay them for us will you?"

I frowned, "I'll think about it, but I may not pay them. I warned you and mom that you can't just spend what you want now."

I walked faster away from them and heard them muttering behind me. I guessed they were discussing how to get around me, but I was feeling quite hard-nosed.

It was in the afternoon that I was standing in the bathroom trying to find something in the cabinet on the wall, when I was suddenly aware that my sister had walked in and was standing close behind me. She started whispering in my ear.

"My credit card bill is a lot less than mom's. You could just pay mine off."

I didn't turn round to face her. "I don't think so," I whispered back.

Suddenly she put her arms around my waist and hugged me.

She carried on whispering, "I think that you really want to be kind to your sister."

I was so shocked I didn't know what to say. She had never hugged me that way before and I was very aware of the feel of her breasts in my back.

Suddenly she lowered both her hands and gripped my cock through my pants. I gasped, stunned at her action.

She giggled and whispered, "C'mon Jimmy, we both know what you want me to do now," and started unbuckling my belt.

I was transfixed, my hands at my sides, waiting frozen for what she would do next.

She didn't hesitate but, as soon as my belt was undone, started unzipping my pants. She was acting quickly now, perhaps nervous that I might attempt to stop her. Thrusting two hands down into the front of my boxers, she pulled out my cock and squeezed it in her fingers. It was rock hard in an instant and, as she gripped it in both hands, I could feel her relax as she felt more confident.

She giggled again and whispered, "Do you like your sister's fingers around your cock, Jimmy?"

This was my fantasy come true, "Oh yes," I groaned as she rubbed her fingertips over my helmet.

"The credit card bill?" she whispered as she slowly jacked me off.

"No problem," I gasped.

"Good boy," whispered Sophie as her magical fingers caressed me more firmly.

I was worried she was going to rush it, but I needn't have been concerned. She jacked me steadily and I began panting hard.

"I can't believe how big you are, Jimmy," she whispered, with another giggle.

I groaned loudly and she laughed delightedly as my jizz shot out between her fingers, splattering the bathroom wall. Kissing me on the back of my neck, she let my cock go and left me standing there.

I couldn't believe what had just happened. The experience had been fantastic. In fact it had been so good that I decided I would pay off mom's credit card bill as well. I resolved to tell mom as we had lunch together the following day.

The next day I felt somewhat in a daze. My sister had disappeared out early, no doubt to do some more shopping. Mom was in the kitchen as I entered it. She had her back to me, cutting something up. She seemed to have a T-shirt on which was so old I'd forgotten she owned it.

I moved towards the kitchen window and was staring abstractedly out of it, when suddenly I felt mom press into me from behind with her arms coming around my waist as my sister's had done the previous day. Mom's breasts felt even more substantial in my back than my sister's had done.

Mom's hands were already unbuckling my belt as she whispered, "I hear you enjoyed your sister's hands around your cock yesterday."

By the time I'd gulped and was about to respond, she'd already pulled my pants and boxers down to my knees and had grasped my cock. It sprung to a hard erection in her fingers.

She cooed in my ear. "How do you like mommy's fingers round your cock Jimmy?"

My response was just a groan as she pulled me around to face her. Her T-shirt was very low cut, her big breasts pushing out the top. I stared at those two wonderful globes, her cleavage plunging down the center.

She was smiling at me as she gently gripped my mushroom head. Pre-cum had already started emerging from my tip and she tenderly smoothed it over my helmet with her thumb. I was in heaven as she whispered, "my credit card bill?"

I was incapable of speech and could only groan and nod my head.

"I'll take that as a yes," she whispered.

She started a steady jacking movement with her right fist and tenderly cradled my balls in her left hand.

"Sophie said that you had a big cock, but I never imagined that you would be as blessed as you are," she murmured admiringly with a mother's pride in her voice.

As she worked the head of my boner, I couldn't take my eyes off her jiggling big breasts. They were jostling in time with her hand movements, which was certainly what she intended when she'd dressed, squeezing herself into that T-shirt.

"I always knew you would turn out to be a big tits man," she whispered. "I've seen you staring at my large breasts when you thought I wasn't looking."

She whispered in an even quieter voice, "I bet you've been masturbating in bed fantasizing about what you'd like to do to mommy's big breasts."

This was all too much for me and I knew I couldn't hold myself back any longer. Although in my excitement my throat was so constrained that it was difficult for me to speak, I managed to warn her.

"Mom I'm cu-"

Mom knew what I was going to say and quickly interrupted me.

"Don't worry honey. This is an old T-shirt. I want you to shoot your semen all over it."

My groan, as I shot my cum all over her front, was nearly a shout. I was almost sobbing from the pleasure as my hot cum spurted onto her T-shirt and the part of her breasts that were showing. Eventually the torrent stopped and I just stood there breathing very heavily.

Mom looked down at herself clearly pleased with what she'd extracted from me. She smiled at me, blew me a kiss and left the kitchen to go up to her room to change her T-shirt.

After that nothing happened for a few days. I guessed that the next opportunity for handjobs from my sister or my mom would be when they next needed their credit card bills paid. However, things happened quicker than I had anticipated.

I knew that mom and Sophie were going somewhere high class, when I saw them in their most glamorous outfits one evening being picked up from the house in a taxi. I learnt afterwards that they had been to a fashion show, as the next morning my sister walked into my room and stood facing me, a piece of folded paper in her hand.

She smiled confidently, "Jimmy, you know yesterday evening mom and I went to the Versace Evening at the Ritz Hotel, well we've both chosen dresses we would like. Mine's quite expensive and I need your help in paying for it."

Considering that she and mom had been to a fashion show the previous evening, Sophie was very casually dressed. She was wearing tight fitting jeans that showed her ass off nicely and a tightish top which pushed her tits out even more than usual. I could feel my boner hardening as I looked at her as I was feeling certain that another handjob was imminent.

"Don't worry sis," I said reassuringly, "I'll pay off the credit card if you're as nice to me as last time."

Sis smiled coyly, "I'm afraid this time it's a little over my credit limit Jimmy," and handed me the piece of paper.

Unfolding it I could see that it was a photo of a black dress with a price printed underneath it. I took a deep breath. It was not a little over her credit limit, it was way over her credit limit. Dammit, this was ridiculous. I could see the money that the women in my family were spending spiraling higher and higher. It had to stop.

I looked at her with a stern face, "No way. I'll pay off your credit card bill but you will not go over it."

I thought she'd be angry but she just smiled and pouted, "But surely you want me to be nice to you."

As she said the words, she stepped towards me, putting her hands down and squeezing my boner through my pants.

I knew I had to be sensible. Even if I did not agree to the dress, Sophie would spend up to her credit limit and I would get my handjob anyway.

"The answer's No," I said firmly.

I couldn't understand why Sophie was still smiling until she got on her knees and started unzipping me saying, "Not even if your big sister gave you a blowjob."

My mouth was dry as she withdrew my hard cock from my pants. Her mouth was only a couple of inches away from it when she whispered, "shall I suck it?"

My groan was the only answer she needed.

I sat there staring at her as my boner swayed in front of her eyes. She grasped my shaft and bent her head towards it, then put out her tongue, giving the head of my cock a lick, and I groaned again.

She then carried on slowly licking the mushroom head, clearly not rushing to take it in her mouth.

In between licks, she whispered, "I might not suck you after all."

Her licks were getting me frantic and angry.

"If you want me to pay for your dress you will suck me now, you fucking slut!" I shouted.

She was grinning now as she continued her teasing licking. Impetuously I grasped her head and pushed it down, forcing her mouth to open and engulf my helmet. She immediately started sucking it hard and I realized that it had always been her intention to goad me into this action, knowing it would raise the level of my excitement.

I now loved the game we were playing, "Suck me you bitch," I shouted as I still held her head in position.

She started sucking my mushroom head fiercely, moving her head up and down. I kept my hands on her head following her nodding. The feeling was delicious and the sight of her head bobbing up and down on my cock was the realization of one of my favorite fantasies.

I was now groaning loudly as I began to push her head lower forcing my cock down her throat. Oh boy, this was fab. Was there anything better for a teenage boy in this world than having his cock being sucked by his older sister? I was really throat fucking her with long strokes as I felt my cum erupting. I pulled back at the last second so that my helmet was in her mouth and she could continue sucking, extracting my cum and swallowing it.

"That was amazing!" I said with a deep breath as she stood up.

Sophie smiled, "My pleasure, brother."

As she got to the door, she turned back with a smile and said, "Oh, by the way, mom's dress is over her credit limit as well," and left me staring at the door.

I went out for the day and didn't return until late afternoon. There was no sign of either my sister or my mom as I went to my room to have a shower. On my bed was a similar piece of paper to the one my sister had shown me earlier, except this time it was a picture of a red dress rather than a black one. The price showing at the bottom of the page was a similar amount to Sophie's dress.

I smiled grimly to myself as I walked into the shower, thinking how much my family seemed to be costing me. But, as I was washing myself, my cock thickened quickly at the thought that my mom could well be offering the same kind of payment as Sophie had done.

When I went downstairs for my meal, I learnt that Sophie was out and wouldn't be back until late. Mom acted as if everything was normal and didn't mention her dress, so neither did I. It was only after dinner when I was seated on the couch that she approached the subject.

Standing in front of me, she got down slowly on her knees, her hands going forwards to my belt buckle.

Mom had a slight smile playing on her lips in front of me as she said, "So, did you enjoy having your cock in your sister's mouth this morning?"

I wanted to say something but my mouth was so dry I could only breathe heavily as she continued undoing my pants and tugging them off me. She grasped my legs and pulled me forward so that my cock was tantalizingly in front of her face.

She whispered, "Every boy wants to have his cock in his sister's mouth, but it's really only his mommy who knows how best to suck her son's cock to give him the greatest pleasure."

With that statement, her head went down and she slid her lips over my helmet and halfway down the shaft, bringing it up again immediately to repeat the movement. She then continued the steady bobbing of her head, going deeper each time.

I, at last, managed to groan something out, "Oh mom, you suck so great!"

I didn't need to hold her head as I'd done with my sister as my cock was now gliding smoothly through mom's lips and mouth and on to the back of her throat. At the same time, mom was grasping my balls.

The feeling in my cock was exquisite. Mom moved her head in steady even movements, knowing that any increase in speed would have me cumming too quickly.

I waited as long as I could, but soon found that I was spurting jizz. Mom pulled my helmet back from her throat into her mouth and she sucked the knob end with the determination of a child sucking a lollipop.

As mom got off her knees, there was no mention of the money for the dress, but I guess that was taken for granted. She walked back into the kitchen, leaving me to zip my pants up.

As I sat there, staring ahead of me, my mind was racing. First my sister and now my mom had now raised the sex level from handjob to blowjob. There would be no going back. For every cent they would want to spend from now on I would require to be sucked off. I sat there luxuriating in what I saw as my hot fellatio future. My only concern was that they always seemed to be in control of any sex session. I never felt that I was in charge. Still, I smiled as I thought that I could put up with them managing each situation as long as I got sucked off by them. I presumed that the next time I would benefit from their need for cash would be when their credit card bills came due, but things happened a lot quicker than I expected.

It was only two days later that they both went out for the evening again; this time wearing their new dresses. As they put on their coats, I thought they both looked stunningly sexy.

It was near midnight that I heard them both come in. I was lying on my bed in my bathrobe, having just showered, when my sister walked into my room. I thought again how sexy she looked in her black dress, her dark nylons and stilettos completing her sensual outfit.

Sophie smiled at me. "I knew you were up," she said sweetly, "because your light was still on."

It was the beguiling way she was looking at me that told me that there was another money issue coming up. My boner started hardening at the thought of having my cock again in her hot mouth.

Sophie sweetly said, "I know that you will think this outrageous, but mom and I promise that this will be the last big spend that you will need to do for us, not counting our usual monthly credit card bills of course."

I waited nervously for what was coming.

"You see the designer who designed our dresses has recommended a beautiful pendant for each dress, just to finish off the complete outfit. Mom's is obviously a ruby pendant and mine will be a modest diamond pendant."

Sophie then said the cost of the items, making me stunned.

This was ridiculous. Sophie could see the incredulity in my eyes.

"As I said Jimmy, these pendants will be the last big items you will need to buy for us," she looked pleadingly.