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 was not enough to cover household expenses and the small pay supplement from the national pharmacy chain would still leave them in the red each month. His 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 was 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 would 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 was such a sound sleeper he didn'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 didn'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 cleaned the mess he made in the bathroom, Nana accompanied Madison back to her bed. Madison was very quiet because her feelings 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."

"Yuk...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. Their bedroom will smell like a men's locker room. You will be washing their little wee-wee, their little balls and their nasty stinky little butts until they are almost teenagers. Boys just require more care than girls, and they expect you to do everything for them. They get even worse after they become men and get married."

"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 or 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 recall the feel of her brother's big cock sliding in and out of her neglected pussy.

"Was my Dad that hard to take care of and was his brain in his cock?" Nana gasped as she thought back to the time when she gave Ben his first hand job, his first blowjob and his first intercourse with a female. It all started innocently when she tried to give him the usual birds and bees talk. One thing led to another and when she realized that her son had such a large hard cock she had to have it. It started with a simple hand job, and then a passionate blowjob. She got so wet and aroused she straddled him and fucked him most of the night until his cock wouldn't stay hard any longer. He was young and able to last about four extremely long rounds.

"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. Nana returned to her room and masturbated for a full hour before falling back to sleep.

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. And she said that we can control boys by simply controlling their dicks."

Becky had a baffled expression on her face and asked, "What did she mean by that? And it's called a cock; not a dick."

"She also said that girls will always be tasked with taking care of boys because they can't take care of themselves." Madison confidently said before adding. "And we as young mothers will be handling dicks, and balls, and washing dirty butts the rest of our lives."

Madison was in such a hurry to tell what she learned from Nana, she began to get ahead of herself and leave out important information. The girls were not following her and became quite confused.

"Madison....slow down; you aren't really making any sense. Why would your Nana tell you that?" Rena asked.

"What brought that subject matter up?" Susanne asked. "Why would your Nana be talking to you about a boy's private parts anyway?"

Madison took a deep breath; looked around to make sure no unwelcomed ears were close enough to eavesdrop on their conversation.

"It started as an apology from her for shouting at me when I hesitated to touch my brother's dick; I mean cock. Nana caught me off guard when she shouted for me to grab it."

"Wait just a minute." Sally interrupted, "Are you telling us that your Grandmother told you to grab your brother's cock and she got mad and shouted at you when you didn't want to grab it?"

"No...No...it really wasn't like that...I mean it was, but there is more to it than that. I need to start over, because I am getting confused and I know I am confusing all of you."

"Duh!" Rena chimed in, "So far it sounds like either a prank story, or a weird dream you had."

Madison motioned for them to huddle closer to each other so no one outside their circle could hear what she was about to disclose. "Listen everything I am about to tell you is true and each of you have to promise on your mother's grave that you will never tell another living soul."

Madison looked around the table getting the assurance from each of her four friends. They all nodded their pledge to keep the secret. Madison recounted the facts that her Dad left on deployment, their Grandmother came to live with them and Michael and Jerry have to share a queen size bed in the same bedroom. She went on to say that Jerry started bed-wetting because of the stress created by their Dad's deployment. She explained how she and Nana had to wake him up in the middle of the night and take him to the bathroom and wait for him to pee.

"Why did Nana want you to touch Jerry's cock?" They asked in unison.

"No...not Jerry's dick, or cock; she shouted for me to grab Michael's cock before he pissed all over the bathroom floor."

Madison's astonished friends hit her with a series of questions in rapid succession.

"Oh my God; you got touch your twin brother's cock?" Becky said.

"What did it feel like?" Susanne asked.

"How big is it?" Sally asked.

"Well...I wouldn't mind touching Michael's cock. I think he is cute," Rena remarked.

Everyone looked at Rena with a surprised expression.

"Well...I wouldn't. I know he is Madison's brother, but I think he is kind of sexy," She added.

"Hello! The key WORD here is that he is MY brother you are talking about, Rena!"

"Okay...okay, I'm sorry I said anything. I'm just saying that I noticed him gawking at me in my bikini all summer and I would like to at least get a chance to check out HIS assets."

Their conversation was abruptly interrupted when the school bell rang signaling the end of the lunch period. The girls gathered their notebooks and personal things and then proceeded to their afternoon classes. The topic of their lunchroom chitchat was tabled until they could all gather in a quieter place more suitable for their discussion.

The second night, Madison and Nana had developed a routine. They took each brother one at a time to the bathroom, starting with Jerry first. Madison took him by the arm, sliding her right arm under Jerry's left arm pit and Nana took his other arm, sliding her left arm under Jerry's right armpits and slowly maneuvered him to the bathroom. Once in the bathroom they steadied him over the toilet. Nana pulled his boxer shorts down to his knees and they held him balanced over the toilet while he urinated. Once he was through Madison pulled his shorts up from her side and Nana pulled them up from her side. Both brothers slept in boxer shorts, so the same process was followed with Michael. Madison was sleepy and disinterested in Jerry's cock; she dozed off and accidentally allowed him to miss the toilet again. Nana had to nudge her with her foot to keep her awake and alert.

"Madison...Honey, I can't see what's going on down there because of the position I have be in to hold your brothers steady. That's why it is so important for you to stay awake and help me hold them steady. Otherwise they may miss the toilet, and I won't know that they are missing the toilet until I feel the splatter of their urine on my feet."

Madison peered through sleepy eyes and saw that Nana's view was indeed blocked by her brother's limp body. She rebalanced her brother and said, "Sorry, Nana...I will be more careful from now on."

When they returned Jerry to his bed, Nana was exhausted from holding his limp weight. He slipped from her grasp and bounced when he hit the bed. It jarred Michael out of his deep sleep, but did not wake him completely. Madison and Nana wrestled him out of bed and slow walked him through the same routine. Once in the bathroom Nana suggested they position Michael differently since he was so big and heavy. Nana slid her arms under Michael's armpits clasping him tightly to her upper body while interlacing her fingers and locking her hands across his upper chest. She leaned back and held him steady in that position. She instructed Madison to pull his boxer shorts down and then take his penis in her hand while carefully directing his flow in the proper direction.

Unlike before Madison was anxious to get answers to take back to her girlfriends. She recalled what Nana had said earlier about not being able to see what was going on down there and decided to check and see if she really couldn't see. While holding Michael's penis in her right hand, she stealthily brought her left hand up and gently fondled his balls. Michael was half asleep and half awake. He was vaguely aware of a slight tingling in his crotch. His initial impression was he is dreaming someone is tickling his balls. Michael carefully squinted through one eye and couldn't believe he saw his twin sister playing with his balls. He realized he was not dreaming; his sister really was playing with his balls. He closed his eyes tightly, took a slow breath as his cock began to grow and harden into its full six and a half inches.

Madison felt the change in his cock and panicked, pulling her hand away. Michael's hard cock pointed straight up into the air and sprayed piss like a broken water main. She promptly recovered and grabbed his cock, redirecting the flow back into the toilet. Nana became aware of the errant flow and screamed, "Madison...what the hell? Did you fall asleep again?"

"Yes, Nana...I am sorry. It won't happen again," she embarrassingly answered.

They hauled the supposedly sleeping Michael back to his bed before returning to the bathroom to clean up the mess. Nana and Madison returned to their bedrooms and a now wide awake Michael quietly masturbated while thinking about his sister's hand on his cock. He had fantasized many nights about touching Madison's tits and licking her pussy, but had never given much thought to her touching him. At breakfast Madison blushed each time she looked at her brother and recalled the bathroom fiasco. Michael acted as if he was unaware of the event. Madison was relieved that he did not wake up and discover her holding his cock.

The school cafeteria was buzzing with the usual chatter as Madison gathered with her four best friends at their usual table. Her friends could see she was busting with excitement and her face was a crimson red.

"What are you so delighted about?" Becky inquired.

Madison motioned them in close and looked around in all directions to make sure no one was within ear shot of what she was about to disclose.

"Last night I touched Michael's....you know...private stuff."

The girls look at her blankly and Sally said, "So? You've been touching his private stuff for a couple of nights now. What's so different about touching it last night?"

She told them about her Nana saying she could not see what was going on down there because of the way she had to steady him; her view was completely blocked.

"Nana has to hold Michael steady while I direct his flow, and last night she told me her view was totally blocked because of the way she has to hold him. Well...it started me to really thinking. If she can't see what I am doing...and my brother is asleep; why not explore a little bit and get the answers to some of the questions you have been asking me about my brother's private parts."

"Oh, my God...what did you do?" Rena asked.

"Don't keep us in suspense," Susanne added.

Madison looked around the lunchroom again, and then said, "I was holding Michael's cock in my right hand, directing his flow into the toilet, and I looked up to see if Nana really couldn't see what's going on...and I suddenly got brave."

"Oh my, God...what did you do?" Becky interrupted.