The Winston Family Adventures Pt. 03

Michael and Jerry found that in addition to their Dad’s orders to report for active duty, their sister Madison and her four best girlfriends had taken over the family swimming pool. Madison and her friends would spend every day working on their tans and swimming. Jerry would try to stay out of their way, but Michael would spend his time spying on them. Since losing his virginity to Mrs. Glover, he was now looking at Madison in a different way. He was still very fascinated with her tits, but now he wanted to fuck her and lick her pussy. He was also looking at his mother and fantasizing about fucking her. He kept a perpetual hard-on, and it got worse when watching Madison’s girlfriends prance around the pool in their scanty bathing suits. Rena sometimes wore a white bikini and when it was wet showed the outline of her nipples and her little dark patch of pubic hair. Michael was very fascinated with their young developing breast. He was secretly lusting for each of them, but they mostly treated him only as Madison’s annoying twin brother. None of them ever considered returning his attention without Madison’s permission. And so far she hadn’t given it.

Their Dad’s military pay will not be enough to cover household expenses and the small pay supplement from the national pharmacy chain will still leave them in the red each month. Mom had to accept a promotion to a full time night supervisor’s position at the hospital to make up for the difference. A night time position would allow her to see the children off to school in the morning and be there when they returned in the afternoon. The extra pay would help, but they would need to hire a full time nanny to stay with the children at night while Mom is at work.

Ben’s mother volunteered to come for a visit and help Catherine and the children while Ben was away on deployment. Grandmother Winston is a widowed woman in her sixties, but she is still in very good health. She is a good cook and loves the children. She can cook and do light general housekeeping in addition to babysitting the children at night. It was understood that Madison will assist her with the household chores and Michael will be responsible for his younger brother. Grandmother Winston asked the children to call her Nana instead of Grandmother. She moved into Jerry’s room and he had to share a room and bed with his older brother Michael.

Their father hadn’t been deployed a week before Jerry began wetting the bed. Jerry and Michael share a queen-size bed. When Jerry wet the bed during the night, there was such a large puddle you couldn’t tell who actually wet the bed, or if perhaps both had wet the bed. Michael denied it was him and Jerry is such a sound sleeper he doesn’t know for sure if it was him or his big brother.

Catherine bought a water repellent mattress cover and asked Nana to make sure Jerry went to the bathroom before going to sleep. She also suggested Nana wake him up during the night to empty his bladder again. Catherine also suggested that she do the same for Michael just to be on the safe side. Both boys are extremely heavy sleepers and Nana wondered how she would ever be able to get them to and from the bathroom without help.

That first night Nana managed to walk an extremely sleepy Jerry to the bathroom and really struggled to hold him up while he relieved his bladder. He was so out of it he didn’t even wakeup during the process. Nana struggled to hold him and he ended up pissing all over the toilet and floor. Nana cleaned the mess, and then she went to get Michael. He was too big and heavy for her to lift, so she reluctantly awakened Madison and asked her to assist with her twin brother. Michael doesn’t sleep in a shirt, only boxer short so there was nothing but bare skin from the waist up; no clothing to grip to steady him. All went well until a very sleepy Michael also began missing the toilet.

“Madison…grab it. Grab his thing and direct the flow into the toilet,” Nana urgently shouted.

Madison glanced up at Nana with a shocked expression and said, “Yuk…I’m not going to touch my brother’s thing; besides, he’s too old for me to be touching like that.”

“Damn it…just do it”, Nana shouted in an abrupt agitated tone of voice. “Just take it and point it so it goes in the toilet and not all over the damn floor.”

Nana’s abruptness startled Madison, and it stirred Michael out of his grogginess. He became vaguely aware of Madison as she grudgingly took his penis between her thumb and index and directed his flow into the toilet bowl. Madison refused to look at her brother’s penis while she assisted Nana with relieving his extremely full bladder. She was so embarrassed and felt like she was going to be sick, but she did as her Nana had ordered. Michael’s cock began to respond to his sister’s touch and he started to develop an erection. She felt the difference, but said nothing. After they returned him to his bed and clean the mess he made in the bathroom, Nana escorted Madison back to her bed. Madison was very quiet because her feels were hurt and Nana felt dreadful about being so brusque with her.

“Honey…I’m sorry for snapping at you like that, but we needed to act quickly before we had a bigger mess on our hands.” Nana tucked Madison in her bed then sat on the edge.

She patted her granddaughter on the leg and said, “I hate to be the one to tell you this, but you and I were born female. And you will soon find, as I did, that the better part of your life will be spent cleaning up after men.”

“Why?”

“That’s just the way it is, Sweetheart. I know you found it uncomfortable to touch your twin brother’s you know what, but you will have to just get use to touching those things. It’s something that you will be called upon to do more and more as you grow older.”

“Why?”

Nana chuckled and said, “I use to ask myself that same question when I was younger, but believe me; when you get older those things won’t seem as unpleasant as it did tonight.”

“What do you mean, Nana?”

Nana had to be careful how she answered the question. She still saw Madison as a naive young teenager. She wasn’t even dating yet, so Nana didn’t want to go into the ‘birds and bees’ discussion. She decided to approach it from the motherhood point of view.

“Someday, Honey….uh…you may be a young mother and maybe have a couple boys like your two brothers. You will find that it takes a lot of patience to raise boys. For one thing, you will be constantly picking up after them. You will be washing their little wee-wee, their little balls and their nasty stinky little butts. Boys just require more care than girls, and they expect you to do everything for them. They get even worse after they become men.”

“Why does it get worse as they become men?”

“I’m not sure I have a satisfactory answer for you, but I can assure you that somewhere down the road there are some rewards for doing all that.”

“What kind of rewards?”

Nana laughed and said, “You are too young to learn about stuff like that right now, but I can tell you for sure a man’s brain is in his penis and if you control his penis, you control the man.”

“What do you mean….control the man?”

At that moment Nana’s mind flashed back to the first time she touched her brother’s cock. It all started with a game of Truth and Dare. She had dared him to show her his cock. From there it led to touching it, then sucking it. Over the next few weeks they fucked and sucked each other in every position of the Kama Sutra. Sometimes, late at night, she can still recollect the feel of her brother’s big cock sliding in and out of her neglected pussy.

“Honey….let’s save that discussion for when you are a bit older. Right now you need to get back to sleep because in a couple of hours it will be time to get up and go to school.”

Nana turned out the light and trudged back to her room. Madison tossed and turned trying to make sense of what her grandmother had just told her about men and what was expected of a woman. Nana seems to have generated more questions than answers.

Morning came entirely too soon to suit Madison. When she went down for breakfast, she was still embarrassed from having to touch her twin brother’s private area. Michael and Jerry both seem oblivious to the fact they were escorted to the bathroom during the middle of the night. Catherine arrived home from work just as everyone was trying to get ready for school and Nana was busy in the kitchen preparing breakfast. The place was in a general turmoil, but eventually it all fell routinely into its usual daily schedule.

Michael and Madison arrived at school just as the bell was ringing for them to report to home room for roll call. Michael joined a couple of his friends and they headed off to their assigned homeroom. Madison spotted Becky and Rena down the hall at their lockers and shouted for them to meet in the cafeteria at noontime. Becky gave her the thumbs up and both rushed off to class. Catherine ate a light breakfast then took her much needed shower and went to bed. Nana did some routine housework and then watched her favorite soap opera before lying down for a brief nap.

When the lunch bell finally rang, Madison rushed to the cafeteria to find her friends. She was bursting with excitement. She couldn’t wait to discuss what she had learned from her Nana with Becky, Susanne, Rena and Sally. She enthusiastically related the events of the preceding night.

Madison leaned in close to her friends and whispered, “My Nana told me that boys have their brains in their dicks and they think with their dicks most of the time.