Billy Gets a Babysitter – Chapter Four

Billy Gets a Babysitter


Chapter 4

When billy and his Mommy got home, Kathy and Becky were full of questions on how it went with his new babysitter. Billy told them that they did their homework together (with billy naked), and then afterwards they watched TV and then it was his bathtime.

“Did Tiffany play with your peenie in the bathtub”, Kathy asked, with a big smile.

“No, but She let me play with myself and She left me alone in the tub to do that for a while”, billy told Them.

“You must have been so excited billy”, Becky said. “What was Tiffany wearing”, She asked.

‘Oh, just a tshirt and panties, Her legs and feet were bare”, he replied.

Both girls smiled and Mommy said, “you must have been beside yourself with horniness, you poor thing. Did Tiffany dry you off”, Mommy asked. 

“Well She dried me off, but She didn’t touch my peenie”, Billy told Them.

“Good” his Mommy said. “If She would have rubbed your peenie, I am sure you would have sprayed a big mess all over their bathroom floor”.

“He sure would have”, both Sisters said in unison.

“Anyway, it’s been quite a day for you billy. You can go to your room now and play with yourself and think about Tiffany….and Your Sisters and Me, don’t forget about us!”, She said.

“And be careful billy, I can see that you are extremely excited” as She looked at his pink and bobbing penis. “When the girls go to bed, they will tie your hands to the bed posts just to make sure you don’t do something in the night”.

“Yes Mommy, thank You”, he said.

Billy went upstairs and laid naked on top of the bedsheets, not even bothering with his computer. He wanted to think about Tiffany….he laid there for almost two hours, having edge after edge after edge with thoughts of Tiffany’s voice, legs, feet and face in his head.

Kathy and Becky walked in the room. “Oh yeah”, he had a good time today alright”, Becky said. “Just look at him”, said Kathy.

“Go take a pee”, said Becky. “Because you wont be able to get up in the night to take one”.

They tied his arms loosely to his bed posts. Not too tight, but tight enough that there was no way he could touch his penis. As they pulled the blanket over his straining, pink penis, Kathy said, “I think he will try and hump the bedsheet. We should maybe put some panties on him, so that he can’t rub the sheet so easily”, She added.

She called out to Her Mom…”Mom, can we put panties on billy, we think he will try and rub his peenie against the bedsheets tonight”.

“Good idea Girls, please do”, Mommy responded.

With that, Kathy pulled on a pair of cute cotton panties, ever so carefully over his penis.

“Are you okay?”, She asked. “The panties aren’t gonna make you squirt are they”.

“No, I am okay, thank You”, billy said.

Both Girls gave his penis a light pat through the panties and then pulled the bedsheet up over him.

“Pleasant dreams”, they laughed as they walked out of the room.

Billy laid there, still thinking of Tiffany, and looking forward to the next day. Because tomorrow was another babysitting day.

Billy met with Tiffany at the bus stop again.

“Hi billy, did you have a good night and day at school”, She asked.

“Yes Miss, thank You”, he replied.

“Good, here is our bus, let’s go”, She said. “You sit beside me again”, She instructed him.

Again, the middle school girls gathered around to ask more questions about the babysitting.

“Was billy a good boy”, one cute grade sixer asked.

“Oh, he was very good”, said Tiffany, “even in the bathtub”, She added.

“You gave him a bath??”, two girls asked in unison.

“Yes of course I am his babysitter after all”, said Tiffany.

“Was he bare naked?” one of the girls asked.

“Oh, he was very very naked, weren’t you billy”, Tiffany asked him.

“Yes Miss”, he replied.

“He calls you Miss now”, said one girl. “That is so cute”

There were more comments and questions on the way about his nakedness, and did he have a boner, and did he touch himself, and did Tiffany touch him…Tiffany answered all of the questions truthfully. Billy had a throbbing peenie in his pants the whole way.

Finally they got to Tiffany’s house, and once inside, billy couldn’t wait to take his clothes off, which he did right away.

Tiffany’s Mom came to the door, but billy was already naked.

“Oh naked already billy, kind of anxious today are you”, She laughed.

“Yes Maam”, he replied.

“Well, you will have fun later, but for now it’s homework time. Tiffany go get changed and sit with billy at the table to do your homework”, She told Tiffany.

Tiffany came back down after changing, and she had on a tshirt and panties again, but this time the tshirt barely covered Her nipples. He bare belly was showing completely. She had on very cute, tight, and small cotton panties. Tiffany didn’t have any breasts yet, but billy was thrilled to see how sexily She covered up Her nipples. Instinctively, his hand went to his penis.

Tiffany grabbed his arm…”not now billy, we have to do homework”, as She removed his hand from his aching penis.

After homework was done, Tiffany’s Mom told billy to come and sit in the front room with Her.

Tiffany and billy sat on the couch together. Billy was very conscious of his throbbing penis. He could not keep his eyes off of Tiffany, and her incredibly sexiness.

“I see that you like the way that Tiffany is dressed”, She said as all three of them glanced at his penis.

“Yes Maam”, he replied, rather shyly.

“That’s okay, we understand, because in our house billy, we live differently than most others, but we live much like you do in your house”, She said.

“Does that mean that Tommy has to be naked all the time Maam”, billy said, referring to Tiffany’s older brother.

“No, not quite”, She stated.

“But Tiffany’s stepfather has to. You see, the kids don’t refer to him as dad or father. What do you call him, Tiffany?”, her Mother asked.

“We call him shithead”, Tiffany said with a laugh. Her Mom laughed too.

“He is a disgusting pervert, who cannot keep his hands off his penis, and so we make him stay naked and smooth at all times. He must follow the instructions and orders of any of us, including Tommy, without question. Sort of like you, in your house, right Billy”, She stated.

“Yes Maam, I guess so”, billy said quietly. “Does Tommy order his…shithead around too”, billy asked.

“Yes, we all do”, She answered. “Anyone that visits our house can order him around, except you billy, because after all him and you are sort of the same”. She added.

“Get in here shithead”, She called out.

With that, shithead or Mr. Adams, came into the living room. He was a small man, completely naked, completely smooth, with a very small penis. Billy stared at him, realizing that they did not look that much different at the moment, except that billy’s penis was still almost hard, but his was limp.

“Look at Tiffany and get your penis hard”, She said. “Its okay billy, you are already stiff, I am talking to shithead”, She added.

With that, Tiffany opened her legs a bit, and shithead stared and masturbated himself. He was completely erect within a minute or so.

“Go put your penises together, I want to see who is smaller”, She said.

Billy got up nervously, and went to shithead and they put their erections side by side. Billy’s was marginally bigger.

“Just as I thought”, said Tiffany’s Mom.

“Okay go to your room shithead, we don’t want you in here now”, She ordered.

With that, he left the room. Billy felt a bit bewildered by what was happening.

“Okay that’s not quite all billy”, She went on. You see Tommy, is a jock at school, but at home, he likes to be a girl. We call him Tammy at home”.

“Tammy come here”, She called out.

With that, Tommy or now Tammy came downstairs dressed in a very very short skirt, with a shirt tied up just under his nipples, exposing his smooth belly. He was bare legged and bare foot, with painted nails.

“Now billy, because you don’t have a girlfriend, and Tammy doesn’t have a boyfriend, we though you two would be a perfect pair”.

Tiffany looked on with a glazed look on her face, taking this in.
“Tammy, sit between billy and your Sister and introduce yourself”, She told him.

“Hi, I am Tammy”, Tammy said to billy.

“Hi”, was all billy could muster.

They sat on the couch together, naked billy, Tammy and his little Sister.

“Mom, can you tell them to make out, please, I want to see them do it”, Tiffany said rather urgently. She had opened Her legs a bit more.

“Sure sweetie…okay, you two, get to know each other, here on the couch. You can kiss and touch. Tammy be careful. You can touch his peenie, but don’t make him squirt. He is not allowed to, unless his Mother and Sisters are watching, and they will be over in a while”, She said.

The scene was so sexual, that billy was actually afraid of shooting off without touching, but Tammy started to kiss him, and then french kiss, and then lightly play with his penis. Billy responded by putting his hand on Tammy’s thighs, and inching up to her panties.

Tiffany, can you be a dear, and go fetch a pair of little panties for billy”, She asked. “I am afraid that if we leave him bare naked, he might spray by accident.”

“Sure Mom”, and she returned with a cute pair of Her panties.

“Stand up please billy”, She said.

She pulled them up his legs, and whene She pulled them over the top of his penis, billy gasped, and jerked backwards.

“Oh gosh, be careful sweetie”, She said to Tiffany. “He is really really close”.

With that, Tiffany pulled the elastic far back as to avoid any contact with his peenie until the panties were all the way up. Then she slowly released the elastic until the panties were fully on.

“You okay billy?”, Tiffany asked.

“Yes thank You Miss”, he replied.

With that, billy and Tammy returned to their make out session. But this time, Tammy only fondled billy’s peenie through the panties, which was much safer.

Tiffany was kneeling at the end of the couch, with Her own hand on the outside of Her panties.

“This is so great Mom”, Tiffany cooed.

“I am glad you enjoy it dear”, Her Mom answered.

Just then the doorbell rang, and in came billy’s Mom along with Kathy and Becky.

“Whoah, look at Tommy”, said Becky. He is gorgeous.

“We call her Tammy”, Tiffany said.

“So cool” chimed in Kathy.

“As your Mom and I talked about, billy doesn’t have a girlfriend and Tammy doesn’t have a boyfriend, so we thought that they were perfect for each other”, Tiffany’s Mom said.

“Oh they are”, said Kathy.

“My, you look so lovely Tiffany”, said billy’s Mom. “billy said he was really excited by you, and I can see why”, She said.

“But looks like billy has a new girlfriend now”.

Everyone laughed, except billy and Tammy who were still engrossed in their make out session, petting and panting and kissing and licking.

“Why don’t we let billy and Tammy alone and all of us girls go out for something to eat”, billy’s Mom said.

“Where is your husband”, billy’s Mom asked.

“He is masturbating in his room. He won’t bother anyone”.

“Okay, you two lovebirds have fun, we will be back later. Billy, don’t take your panties off please. You two have fun with your panties on”, billy’s Mother instructed.

“Yes Mommy”, billy said.

“Can Tammy get naked”, billy’s Mother asked Tammy’s mother.

“Sure, if she wants to, but Tammy I don’t want you to make cummies until we get back, is that understood”, She asked sternly.

“Yes Mommy”, Tammy answered.

With that, all the girls got ready, and left the house, leaving billy and Tammy to explore each other. The two sex crazed teens did everything except go all the way, and did as much as they could with billy keeping his panties on. Tammy wanted to get naked after a while, so soon, they were on the floor, Tammy completely naked, billy with his panties on, still going at it.

The ladies returned and found billy and Tammy naked on the floor, both of them completely erect and leaking. The front of billy’s panties had a wet spot on them.

“Mom, can we watch them cum, please”. Tiffany asked Her Mom.

“What do you think girls, should they”, She looked at billy’s Mother.

“I guess so…it’s been weeks for billy”, She replied.

“Okay, Tammy you go first, billy will make you spurt”, Tammy’s mother instructed. All the girls knelt around the boys, and the two Mommies sat on the couch.

Billy started to pump Tammy’s erect penis, and within a few seconds, Tammy groaned loudly, and heavy, copious spurts started shooting out of his girly penis. Billy continued the stroking until they ceased, and even after. The shots landed all over Tammy’s naked body, and the floor.

“Say thank you to billy”, his Mother instructed.

“Thanks billy”, Tammy said.

“That was so hot”, said Kathy.

“Okay, billy, your turn….and how should it happen”, his Mother asked, the question going to the room.

“How about Kathy and I make him shoot” said Tiffany.

Billy moaned with this, and hoped so much his Mommy would agree.

“Okay”, she said much to billy’s delight.

“Lay on the floor billy, and the girls will both touch your peenie, and make you squirt all over yourself…you are so lucky”, his Mommy told him.

The girls kneeled either side and both put their hands on this little, hairless penis and started to rub. Within seconds, he cried out that he was going to squirt. And as always it started to come out like pee, in a solid stream. This delighted Tammy, and then the squirts started..many of them, shooting up past his head, on to his face his neck chest and belly.

“Okay, billy will lick up all of his and Tammy’s sperm..thats what he does”, his Mommy announced.

With that, billy started licking the cum off of Tammy and from the floor around Her, and then scooped his own cum up and licked the floor where he had shot on to it.



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