Billy 5: Billy Gets a Babysitter

By Fred

Copyright 2016 by Fred, all rights reserved

fredfrancis2015@outlook.com

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Chapter 1

 
Billy was at home alone again. Three times a week, his little Sisters had after school activities, and his Mom was still at work. Of course billy did not have any after school activities, not like the other kids.
 
But billy enjoyed his time alone in the afternoon after school. He was home alone, naked, and he made sure his chores were done, and his homework done and on display for Mommy to check when She got home. But often, he could complete all of that in an hour or so, which meant he had another hour and a half to enjoy himself.
 
That was the case today. Of course, he had been naked since he got home, but now he could relax and enjoy playing with his penis. He watched some of his favourite porn, and then got an overwhelming urge to wear girls’ panties. He found himself going up to Kathy’s room, his youngest sister. Although, he was allowed to go to her room to clean it, he was not allowed in there for any other reason. So, he was breaking a very strong rule by doing this, but the urge to play with his 13 year old sister’s panties was too much to resist. He soon found himself laying on her bed, with a few pairs of her pretty panties laying around him, and he was even using a pair wrapped around his throbbing penis as he masturbated. Oh, the bliss…He was trying on other pair’s of her panties, occasionally looking at the clock to make sure he had enough time to tidy up before anyone came home. He was lost in his world of lust, his penis throbbing with pleasure. He had a pair of Kathy’s sexiest panties, blue shiny and tiny on. He pulled them down to his knees and laid back on the bed and used another pair to wrap around his hairless peenie.
 
“What the hell”, was what billy heard next. He looked up and there was Kathy and Becky, both standing there, looking at him in disbelief. He couldn’t do anything to hide what he was doing. It was plain to see.
 
“Oh my god look at him”, Becky said to Kathy. “And look at the mess he has made of your panty drawer!”, she exclaimed.
 
Billy didn’t know what to do, he just laid there on his back with the panties at his knees, and the other pair in his hand, wrapped around his now wilting penis.
 
‘I’m sorry”, was all he could muster.
 
“Sorry??, that’s it?”, cried out Kathy. “You are in so much trouble when Mom gets home”.
 
“For now, you stay exactly like that, do not pick up any panties, do not take those ones off that you have half on, keep that other pair around your stupid peenie, and keep playing with yourself. Get yourself rock hard and leaking, and you had better be that way when Mom gets home. I want her to see you exactly as we found you”, Becky told him.
“Yes, Becky, I am sorry, Kathy”, he muttered.
 
“Whatever”, they said in unison, as they left him like that to go downstairs.
 
Billy kept playing, as he knew he had better be hard and leaking when Mom came home, and because he had lost track of time, she was due any moment. The girls had come home at their usual time, but Billy was so lost in lust that he didn’t read the clock correctly. Stupid, stupid, stupid Billy.
 
A half an hour later, Mommy, Kathy and Becky were all standing at the door.
 
“This is exactly how we found him Mom”, Kathy said. “He was all hard and leaking, just like he is right now”.
 
“So, you are having fun when all by yourself, huh Billy”, Mommy said without a smile.
 
“I am so sorry Mommy, I will clean up everything and wash her panties and put them back, and promise never to do this again”, Billy said, as he continued to play with his penis.
 
“Of course you will billy, but it is too late to put this back in the bottle”, as Mommy looked around.
 
“Okay, keep those panties half on, pull them up to your upper thighs so that they don’t come off. But keep your peenie fully exposed. And then clean up these panties, and hand wash them all, and hang them to dry . God knows how much precum you might have got on them. After that is done, report downstairs for your punishment”, Mommy told him.
 
“What will the punishment be Mommy”, he asked, fearfully.
 
“You will find out”, Mommy said.
 
Billy made sure he did a good job of washing the panties, as he knew he had spilt precum on some of them. He carefully hung them to dry, and then looked around her room again, smoothed out her bed, and then went downstairs. Still, with the shiny blue, tight panties pulled down to his thighs.
 
“I am finished cleaning up Mommy” , he said as he entered the family room.
 
“Go check everything girls, make sure you are happy with it, and then come back down”, Mommy ordered.
 
“What are we going to with you billy”, his Mommy said. “No matter how hard we try and train you, you disappoint us”.
 
“I am so sorry”, billy said, as he was nearly in tears. His peenie was not completely soft and only about 2 inches long.
 
The girls came back downstairs.
 
“Looks okay Mom”, Kathy said.
 
“Okay, well billy, you are going to get 10 whacks with the wooden spoon on your peenie for starters. Step up to the dining room table, and try and lay your little peenie on the table.
 
Billy did as he was told, although his penis was very short, and did not lay on the table easily. He had to just his hips forward to try and keep his penis exposed on the table top.
 
“That will do. Kathy, please get the wooden spoon”. Kathy smiled at her Mom and Becky and retrieved the dreaded instrument from the kitchen.
 
“Count them out and say “sorry Kathy”, after each one”. Mommy ordered.
 
“Yes Mommy”, billy said, with real fear in his voice.
 
“1, sorry Kathy”, “2, sorry Kathy”….it continued until 10. He was yelping with each hit after the second one.
 
When they were over, Mommy told him to back away from the table, and the three Females watched, as his peenie turned purple and swollen. Billy looked down in horror, at his hurt penis. It was going to be so difficult to get and stay hard now, and he just knew that his Mommy would insist on it.
 
He thought it was over, but no….”Okay Kathy, you give him 20 whacks on his bare bum, 10 on each cheek. Again, billy count them out and say sorry to Kathy after each one”, Mommy ordered.
 
With the shiny blue panties still at his mid thigh, he stood as Kathy administered the blows, being sure to say exactly what Mommy ordered him too. He made eye contact with Becky, almost pleading with Her, but She was just smiling.
 
“Okay, that’s it. Take those panties off, wash and hang them, and then go to bed with no supper. We will figure out the best way forward in the morning”, Mommy told him.
 
With that, billy went up stairs, washed the panties and went to bed, naked. He touched his sore penis, and actually did manage to get himself hard, even though it stung. He loved playing with his penis so much.
 
 


Chapter Two


 
The next morning, things were as usual at the house. billy got up early, and went downstairs, naked and tidied up the kitchen and family room from the night before. He waited for his Sisters and Mommy to come downstairs and then went to Their rooms to make Their beds and tidy up. And then, he went back downstairs and cleaned up their breakfast dishes and made himself breakfast, cleaned up his dishes, and then upstairs to shower, shave his body, and get ready for school. Mommy never said a word to him and his Sisters just snickered about his purple and swollen penis.
 
That afternoon, the Girls were not at extra curricular activities, so all three of them took the bus home together. Kathy was telling billy that Mommy was really mad at him, and that She was talking about getting a babysitter for him.
 
Once home, billy got naked, and did his homework at the kitchen table. Becky and Kathy got changed into their after school clothes, which very often meant tshirts and panties only, which is what They wore today. billy liked looking at Them in their tshirt and panties, and the Girls noticed that his peenie got hard, even though it was quite bruised. They did love to tease him, so part way through his homework, They both stood beside him, at the table, and lifted Their tshirts, so that he could see Their panties, and They told him to play with himself. Which he did of course….billy was staring and drooling and leaking…the Girls were laughing at him. He had quite a bit of homework to do, and the Girls were purposefully trying to make it so his homework wouldn’t be done when Mommy got home. But, They finally stopped Their teasing, and billy finished his homework once his peenie got soft again.
 
Mommy arrived home, and sat at the table with naked billy and Kathy and Becky.
 
“Okay, I have decided that you need a babysitter, billy”, She told him.
 
“But Mommy, I am 17 years old…”, he started. But Mommy cut him off.
 
“You may be 17, but you act like a 10 year old”, She told him.
 
“I spoke to Chrissy’s Mom about it, but Chrissy has after school activities as well.” Billy was disappointed to hear that, because if he had to have a babysitter, it would have been wonderful to have Chrissy do it. He was so in lust and love with Her still.
 
But I did speak to Mrs. Adams and Tiffany will be able to do it for us.
 
“Really Mom?”, Kathy said. “She is a year younger than me, I think she just turned 12”.
 
“Yes, She is available, and I have been friends with Her Mom for a long time. Mrs. Adams knows all about billy and his perversions and his lifestyle, and She thought it would be a great idea for Tiffany to babysit billy”, Mommy told them.
 
“Billy, do you know Her”, Mommy asked.
 
“I am not sure, sounds like She is in Grade six”, Billy asked.
 
“Yes billy, you know Her, she is the really cute blonde Girl in the grade below me. She just started middle school this year. She is always coming to school in really short pants and short skirts…I am sure you have noticed Her. She has an older brother, Tommy, in grade 9”, said Kathy.
 
“Oh yeah, I think so”, billy muttered. He did know who she was. She was just a kid, but billy had seen Her at the school, and definitely noticed how cute She is.
 
“I am sure it is more than you think so”, said Becky. “I am sure you have masturbated and thought about Her, haven’t you”, She asked.
 
“Maybe, not sure..Mommy please, does She have to? I am 17, She is 12, I promise to be a good boy”, he pleaded.
 
“No billy. On the days that Kathy and Becky stay after school, you will take the bus to Tiffany’s house, and I will come and pick you up on my way home from work”, Mommy explained,
 
“I have to go to Her house Mommy?”, billy asked. “Really”? he asked again, pleading.
 
“Yes, She cannot come over here, so you will go to Her house. She has an older brother, Tommy, and Her Mother is home at the same time. And the same rules will be in effect, as they are here. You will get naked immediately upon getting inside the house, you will do your homework, and you will follow any instructions that anyone in their family has for you, while you are a naked guest there. Do you understand”, Mommy said sternly.
 
“Yes Mommy”, billy said. But, he was panicking. Except for Chrissy’s birthday party, he had never been naked in front of others. And he had never been naked in front of others without at least his Sisters or Mommy being there. Tiffany was very cute and hot, so he was kind of thinking about Her, but Tommy Her brother was a bit of an athletic type, and was with the “in crowd” at school. So different than billy. This was going to be so humiliating…
 


Chapter Three

 
The very next day was the first day that billy was going to be babysitting. His Mommy told him to meet Tiffany at the bus area after school, and She would take him to Her house. Billy was full of dread during the day. He was scared of girls in general, and even more scared of Tiffany right now, but there was nothing he could do about it. He just hoped that She would be nice to him.
 
He went to the bus area after class, and immediately noticed Her. She was wearing a very short plaid, school girl skirt, with Her Bare legs showing and sandals showing her bare toes. Billy couldn’t help but notice. He felt a stirring in his peenie. It had been almost six weeks since Mommy had let him spurt, and he was constantly aroused. And the sight of this cute middle school hottie, wasn’t making it any easier.
 
“Hi billy, I am Tiffany”, she said.
 
“Oh hi”, billy said.
 
“Well, this is my bus, let’s get on. You sit beside me”, She ordered.
 
Once on the bus, some of Her friends were asking who the high schooler was. She told them that She was babysitting him.
 
“What!”, they said. “He is a senior in high school”, one of them exclaimed.
 
“I know”, Tiffany told them. “But his Mom said he is a very naughty boy when he is alone in the house”. And with that She made the cock jerking motion with Her right hand. All the girls laughed out loud. Billy wanted to disappear in to the bus seat.
 
Once inside the house, Tiffany’s Mom was there, and introduced Herself to Billy.
 
“Okay, off with all of your clothes please”, She said.
 
There was no choice now, he had to. Billy stripped off everything, and stood in front of Tiffany, the sixth grader, and Her Mommy, completely naked and hairless, with his peenie still slightly bruised.
 
“Wow, your toenails are painted red, like a girls”, said Tiffany.
 
“Um yeah, my Sisters like to do that”, billy explained.
 
“They are very cute billy”, Mrs. Adams said.
 
“I see your penis is still a bit sore”, Mrs. Adams said. “Tiffany, billy here, had to have a spanking on his penis after his Mommy caught him playing with Kathy’s panties without permission”, she told Tiffany.
 
“Oh, he likes panties. Can I show him mine Mommy”, she asked.
 
“Yes, but not until he has done his homework”, her Mother replied.
 
Billy’s penis erected at the thought of seeing Tiffany’s panties.
 
“It looks like billy wants to see your panties too”, Mrs. Adams laughed.
 
So, billy and Tiffany sat at the kitchen table and did their homework. Once billy said he was done, Tiffany checked to make sure he had completed it.
 
“Okay, let’s go to the family room for TV time”, She told him.
 
“You sit right there on the couch, I am gonna change in to my after school clothes”, Tiffany told him, as She went upstairs to Her room.
 
Billy found this new situation he was in, both scary and exciting. Being in someone else’s home, completely naked, being babysat by a 12 year old. It made him want to touch his penis, but he was not sure if it was allowed or not. His Mommy had told him that the rules in the Adam’s house, and his house were the same, so he decided that it would be okay, and started to slowly masturbate with thumb and forefinger.
 
He had closed his eyes and was thinking about Tiffany’s legs, when he heard Her say, “Oh, yeah, my Mom told me that you do that a lot, and that it is okay”.
 
He opened his eyes and was startled and excited to see that She had changed into a tshirt and panties. Well, he assumed panties, as the tshirt came to the top of Her thighs, and covered Her panties. He let out a little moan, and was slightly more vigorous with his stroking, at the sight of Her.
 
“Mommy also said, that you are not allowed to shoot your stuff out”, She said.
 
“I have seen my brothers shoot out, and also my dad’s”, she told him. “Too bad you aren’t allowed to shoot it, because they really love to”, she continued.
 
Billy’s head was reeling a bit. Did She just say her brother AND her dad?? What kind of family was this, he wondered. Was this house even more sexual than his own?
 
“I know you think that my brother, Tommy, is a jock, and I guess he is at school, but in this house my Mommy makes sure that the girls rule!”, She explained to him.
 
“Anyway, you will see someday, maybe”, She went on. She was now seated on the other end of the couch from him, with Her bare legs folded under Her. Billy was staring at her perfect little feet and legs and he then got a glimpse of her white panties. His thumb and forefinger were making short, quick, urgent strokes on his straining penis.
 
“Be careful, the last thing I need is you shooting your stuff all over the place on the first time I babysit you!”, Tiffany scolded him.
 
“Your Mommy is paying me nicely for this, and I want to make sure that when She picks you up, She will see your homework done, that you are nice and clean, and that you are very horny. So, let’s go upstairs and give you a bath”, She told him.
 
“Oh, okay, I like getting baths”, he said. “Sometimes my Sisters help me bath”, he told Her.
 
“That’s nice of Them, do They get in the tub with you?”, She asked.
 
“No, i have never seen my sisters bare naked”, he explained.
 
“Well, you certainly won’t be seeing me bare naked either, but I will sit on the edge of the tub and make sure you make yourself squeaky clean, and smooth. I have a shaver to give you. And you can play with your penis for a while after you have made yourself all clean and smooth. How does that sound”, She asked.
 
“It sounds wonderful Tiffany, thank You so much”, he said, while looking at Her toes again.
 
“Wow, you really do like my bare feet. That’s funny. Maybe someday if you are a good boy, you can paint my toenails for me. Would you like that?
 
“Oh yes Tiffany, very much so”, he said with a shaky voice.
 
She laughed.
 
Upstairs, Tiffany showed him around.
 
“That’s my Mom’s bedroom. The door has to be closed all the time”
 
“That’s Tommy’s room. Mom doesn’t let him have a door on his room, because you know what you guys get up to all the time”, She said with a smile. Tommy’s room was rather normal teenage boy room with some posters, a computer, some sport trophies.
 
“This is my room. I get to have a door, but I am not gonna show you my room, just yet”, She explained.
 
“And this is my dad’s room”. The room was not much bigger than a closet, and had nothing in it except a small, singled bed, small desk and computer. No door.
 
“Mom doesn’t let dad have a door either. He doesn’t have many privileges around the house. Mom is pretty strict with him”, Tiffany explained.
 
“Anyway, and this is the bathroom that Mom and I and Tommy use. You can have your bath in here. Let me run the bathwater”.
 
As the tub filled, Tiffany ordered him to hop in.
 
“Okay, clean yourself well, then run this razor over yourself, and then you can play with your penis for a while in the tub”, She instructed him.
 
Billy did as told, and felt so much like a kid being babysat. Naked in the tub, while this middle school hottie sat on the edge of the tub supervising his every move.
 
After cleaning and smoothing, She told him he could play with his penis for 15 minutes in the tub. He started using his thumb and forefinger and staring at Her legs. With that, Tiffany got up, and said she would be back in 15 minutes. She left him alone with this throbbing penis….
 
“Okay, out of the tub. I will dry you off”, She said.
 
Billy stood beside the tub, his little penis sticking straight up. But Tiffany did not touch his penis at all with the towel. She dried every other part, except that one. He was so hoping…against hope.
 
“Okay, clean the tub, hang the towels and come back downstairs”, She ordered him.
 
When he got back downstairs, his Mommy and Mrs. Adams were sitting in the living room, along with Tiffany.
 
“Was he a good boy Tiffany”, his Mommy asked.
 
“Yes he was, he did as told. I let him play with his penis for the last 15 minutes in the tub, I hope that’s okay”, Tiffany asked.
 
“No, that’s fine sweetie, he spends hours each day doing just that”.
 
“He really seems to like my bare feet a lot. He was staring at them all the time.”
 
“Yes, he has a very strong foot fetish, the poor thing. Barefeet make his peenie throb so bad, don’t they hun”, She asked billy.
 
“Yes Mommy, they do”, he replied.
 
“I am sure if you are a good boy, Tiffany will show you her bare feet a lot, won’t you Tiffany?”
 
“Oh yes I enjoy seeing his ‘peenie’ all stiff and sticking out that like that”, Tiffany answered.
 
“Well, I am glad the first day worked out so well. I think tomorrow, the girls are staying after school again, so can you please bring billy home with you again Tiffany”, billy’s Mommy asked.
 
“Yes of course”
 
“Oh, I don’t see Tommy or Mr. Adams here”, she said to Mrs. Adams.
 
“They will be here tomorrow afternoon. Tiffany and I can introduce billy to them. I am sure they will have fun together”.
 
All the girls laughed.
 
“Okay billy, get your clothes on, thank Miss Tiffany, we are going home now”.
 
“Thank you Miss Tiffany”, billy said, as he put his clothes on.
 
 
Chapter Four


 
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 dad..er…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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