The Winston Family Adventures – Chapter 3

“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. 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 having 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 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 dead 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 elated 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.

“I took my left hand and started squeezing and fondling his balls.”

“You didn’t,” Becky gasped.

Madison smugly shook her head yes.

“What did they feel like?” Rena asked.

“Do they have hair on them?” Susanne asked.

“How big is his cock?” Sally wanted to know.

The girls peppered her with a half dozen questions; one right after the other. The questions came so fast and furious, she couldn’t possibly answer them all and for some questions she had no answer to give. It’s Friday, so she suggested they give her a list of questions and she would try to get the answers over the weekend. The school bell rang signaling the end of the lunch period. The girls gathered their notebooks and personal things and then headed off to their afternoon classes; each girl promising to get their list of question to Madison before the end of the day.

Michael still couldn’t believe he wasn’t dreaming and that his sister had really been squeezing his balls the night before. He was vaguely aware that his Nana got him up every night and took him to the bathroom and up until last night he was vaguely aware that his sister Madison often helped Nana lift him. He was generally a heavy sleeper and had always been so sleepy and groggy at the time, nothing was ever clear about what had really taken place. He decided to set his alarm so he would be awake tonight when they take him to the bathroom.