Billy’s Play Date 1

By Fred

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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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The girls and Billy were messing around on a Saturday. The two sisters Kathy (13) and Becky (15) were teasing their bare naked big brother Billy, who was 17 years old, and the subject of endless sexual teasing and humiliation at the hands of his little sisters and his mommy.

“Hey, you know what we should do next Saturday”, Becky said, in an excited tone. “We should arrange a play date for Billy, wouldn’t that be fun?”

As if Billy wasn’t even there, Kathy said, “but who shall it be, how about Chrissy”, she asked.

“Nah, Chrissy has already been with Billy when he has ejaculated three times now…although the last time was in his pants!”, both girls roared with laughter, Billy hung his head in shame, and looked at the tip of his very erect peenie.

“Hey, what about Chrissy’s older brother, Johnny, he is your age, he’s 15”, Kathy said to Becky.

“A guy?”, Becky said…”Hey, why not, that might be fun to see”.

“Hey, come on sisters, don’t I have a say in this”, Billy complained.

“Well, actually no you don’t”, Becky said. “Why would you?”

Just then Billy’s Mommy came in the room and Kathy and Becky told her of their plan for his play date. “That sounds like a lot of fun girls, but does Johnny like boys, especially boys like Billy….sissy boys?”, Mommy asked.

“Well, Chrissy said she has caught him look at boy on boy porn quite a bit”, said Becky.

“It sounds perfect”, said his Mother.

“Mom, but he’s a boy, do I have to have a play date with a boy, can’t I see a girl”, Billy was whining a bit.

“Young sissy boy, unless you want your bottom and peenie spanked, you will be happy and thank your sisters for arranging a date for you. For sure, you can never get a date on your own”, his Mother admonished him.

“But Mommy, please”, he continued to whine.

“Okay, that’s it, Kathy get me the wooden spoon”, she said.
“Okay okay Mommy, I am sorry, I will have a play date with Johnny”, he begged,

“Of course you will, but that doesn’t mean that you can talk back”, she said sternly.

“You know what to do, pull your stiffy down from your belly, so that I can hit the top of it”.

Billy did as he was told. He knew better than to complain now. Mommy gave him 5 hard whacks with the wooden spoon right on the topside of his little boner. It hurt like heck, the girls were laughing, he was yelping. His peenie started to deflate with the stinging…

“Okay, girls you talk to Chrissy, and see if you can arrange for Johnny to sleep over here next Saturday night. I will talk to his Mother as well. I am sure she will be all for it”.

The week had passed normally. Billy doing all the chores, being teased somewhat by his Sisters, masturbating himself whenever he got the free time, looking at his pornography, but being careful as always not to squirt. Unauthorized ejaculations were about the worst thing he could do.

“I talked to Johnny’s Mom, and she is all for it. She says that Johnny definitely likes boys best, and she is very anxious for him to have some experience with another boy. I told her that Billy is just the right choice. Very polite, quiet, accommodating. I told her that you girls would be there as well, and she said great, she would bring Chrissy as well”, the Mother told the girls, and Billy could hear.

Oh great, Billy thought. He was in love with Chrissy, the 13 year old friend of his little sister, and now she was going to watch him play bare naked with another boy. She would never want him for her boyfriend now, after she saw that. But for some reason, that made his peenie feel good, and as he laid in bed that night, he played with himself and imagined Chrissy watching him play with her brother as both boys were bare naked. The idea made him throb…

Saturday morning arrived, and Billy did the house chores as usual. Cleaning the house, making up his Sisters and Mothers bedrooms, doing the laundry. He was up for a couple of hours before anyone else, dutifully working bare naked as always, as Billy was not allowed to wear clothing in the house. After the chores were done, and his Sisters were up, his Mother told the girls to take Billy to the bathroom, and give him a complete body shave to get him ready for his date. Billy laid, kneeled and stood in the tub as his Sisters ran the shaver over his entire body, with special attention to this peenie area. Once they were done, they called their Mom to inspect him.

His Mother had a look everywhere, had him bend over and spread his cheeks, and announced that the girls had done a very good job.

“Paint his finger and toenails as well girls, I think Johnny will like that”, their Mother instructed.

Billy knew what to do. He laid on the floor in the living room, and the girls painted his fingernails first, and then his toes. Kathy mentioned that his peenie was really really hard and leaking. “Johnny is gonna love you”, she giggled.

Johnny, his Mother and his little sister Chrissy all showed up together around mid day. Billy’s mother answered the door and made some small talk with Johnny’s mother. They had been talking on the phone during the week, and had met for coffee, so that they were both completely aware of what their kids would be up to, and they both totally approved.

“Billy, they are here, come down please”, his Mother called out to him.

Billy had been upstairs and was masturbating to sissy porn, and his penis was red and hard and leaking. He knew better than to keep Mommy waiting, so he went downstairs immediately, and was a bit shy to be naked in front of Johnny and his Mother. Chrissy had seen him before….

“Oh hi Billy”, Johnny’s Mother said. “You look like you are raring to go”, she laughed.

“Hi Billy”, Johnny introduced himself to Billy.

“Hi Johnny, nice to meet you”, Billy replied.

“I like your toenails and fingernails” Johnny told him.

“Oh thanks…my Sisters did that for me”, Billy replied.

“As I said, Billy has to remain naked in the house at all times”, his Mother explained.

“Johnny, Billy has to be bare naked, but would you like to take your clothes off too”, Johnny’s mother asked.

“Yes please Mommy”, he said, as he eyed Billy’s naked and smooth body. Johnny had shaved his whole body smooth that morning too, and was anxious to show Billy and the girls and ladies what he looked like.

Billy stared at Johnny’s naked body. His peenie was about the same size as Billy’s. A bit on the small side, and hard already. He noticed that Johnny was completely hairless, like him.

“Go on Billy, touch his peenie and give him a welcome kiss”, Kathy said.

“Yes, come on you two, get to know each other”, Chrissy and Becky chimed in.

Billy was a bit embarrassed to do it, but he knew better than to disobey a command from his Sisters, or any Female for that matter, so he stepped towards Johnny, and fondled Johnny’s penis and gave me him a peck on the cheek. Johnny reciprocated and both boys were cheek to cheek and touching each others penises…and moaning a bit.

Billy’s Mother suggested that the boys go up to Billy’s room to get acquainted with each other. The girls went to the TV room to watch a movie and Johnny’s mother said goodbye to Johnny and to everyone else, thanking them for taking Johnny for the weekend.

Up in the room, Billy was a bit shy, because he had never been naked in his room, with a boy before. He asked if Johnny wanted to watch some porn with him.

“Sounds great” he said.

So, the boys laid on the bed together and started watching some porn, some boy on boy, as well as forced bi, and sissy porn, and touching each others penises, and even french kissing a bit. All this, while their Sisters were downstairs watching a regular movie on the TV.

“I’m not allowed to ejaculate without permission, so if I ask you to stop, please stop, okay, or else I will be in big trouble”, Billy asked.

“Sure, yes, Chrissy told me about that”, Johnny said.

“Can you cum whenever you want to”, Billy asked.

“Yeah I can, but Mom told me about you, and how I have to be careful with you. And she told me that I cannot ejaculate without permission in this house, either”, Johnny told him.

“Okay great, we will be careful with each other then. I have never been with a boy before, have you”, Billy asked.

“Yeah, I play with my two boy cousins quite often”, Johnny said.

“I like you a lot”, Billy said, as he leaned over to kiss Johnny on the mouth. His penis was throbbing in Johnny’s hand.

“I like you too Billy”.

The boys didn’t realize that Mommy had been standing at the door way, and watching.
“Well, am so glad you two like each other so much”, she laughed at them.

“Listen, the girls and I are going out for a few hours. You two stay here in the room…do not leave the room, and continue to play with each other. Enjoy your play date.....we will be back about 6 PM or so, be good boys”.

“Yes Mommy”, Billy said

“Yes Maam”, said Johnny.

So for the next few hours, the boys played and played and watched horny videos, and got each other very close, but were careful not to go to far. Their hard, pink, penises in each others hands, french kissing. They played games where they would make each other have 10 edges, and then it would be the other ones turn. Whoever got the 10 edges fastest, got to go first again. Billy kept winning that game.

Time passed so quickly and before they knew it, they could hear the girls returning, and Becky telling them to go downstairs. They went downstairs, holding hands, with their little boners sticking straight out and up (in Billys case).

“How is the play date going”, asked Chrissy. “Looks like you two really like each other”.

Now, Billy wasn’t worried whether Chrissy would like him any more for playing with her brother. He wanted to show Chrissy how horny her brother made him.

“We are having a lot of fun, Chrissy, thank you”, said Billy.

“Yes, a lot of fun” said Johnny with a smile.

“Okay, we are gonna play a game”, said Mommy.

“We will mark out two boxes on the floor, about one meter by one meter. You two will stand in your own box, and you cannot step outside of it for any reason. You will also have your hands tied behind your back. You have to keep your boner hard all the time. So, the only way you can make sure that happens is for the two of you to rub your peenies together. But, you cannot squirt!”.

Mommy went on to explain to the girls…”You see the beauty of this is that if one of them starts to get even a little bit soft, he has to rub harder against the other, and if the other is too close, he will want to back off, but he cannot step outside the box”

“Oh, this sounds fun”, exclaimed Becky.

“And the winner of the game is the one who stays hardest. We will touch the boys penises after two hours, and whoever is hardest will win. The girls will make the winner squirt with their hands, and the loser will have to lie on his back, put his legs up over his head, and make himself squirt in his own face. How does that sound”, Mother asked.

“Yes Yes Yes”, the girls all said in unison. The boys were quiet, but excited.

“Okay, while you boys are playing your little box game, the girls and I will be watching TV, and just hanging around. We will check on you from time to time”.

The boys had their hands tied behind their backs, the boxes were marked on the kitchen floor, and they began. For the first half hour or so, they both managed to rub penises together and remain very hard, without having to pull back too often. They were both looking down at their rubbing penises, and Billy (and Johnny) saw Billy’s painted toenails at all times. This, combined with everything else, was having an effect on Billy, and he was having to pull back his penis a couple of times a minute. Johnny seemed disappointed every time that Billy had to do it. He seemed to be in better control. Both boys remained rock hard, but Billy was so determined to be the hardest when the girls checked..he so wanted Chrissy (and his Sisters) to make him squirt with their hands. That thought made him pull back his penis every time.

As time went on, Johnny was now having to pull his penis back, due to the excitement. He pulled his penis back for longer periods than Billy did, maybe 30 seconds or more. His penis remained very hard, but during these long breaks Billy felt like his penis would be less stiff. Not noticeably so, but he could feel it. This worried him, and he made every effort to rub penises for as long as he could take it. The boys had no idea when the girls would do the checking, and they both wanted to masturbated by the girls so bad!

Finally, the girls and Mommy showed up in the kitchen. Both boys groaned when they saw the girls.

Chrissy was wearing a baby doll nightie, very short, and very cute, with her wonderful bare legs and bare feet, with painted toes. The very sight made Billy shoot out a little squirt of clear precum, which Chrissy noticed.

Kathy, who is Chrissy’s age, was wearing a very short pair of boy shorts. So short that her buttocks seemed to be mainly exposed. She wore a short tshirt that exposed a little bit of her bare belly.

Becky had on a tshirt that went down to the top of her thighs. The boys could not tell if she was wearing panties or not. Johnny stared and stared at Becky while dutifully rubbing his peenie against his friend.

Mommy was also present, for the checking.

“Okay, apart you two, let’s see who wins”, Mommy said.

Mommy grabbed each boy’s peenie, one in each hand. She was checking for stiffness, even though both boys appeared to be rock hard. The boys were clearly enjoying this attention, and both were uttering thank you, thank you.

“Well, I have to say that Johnny is the hardest. Congratulations Johnny”, Mommy announced.

A horny smile developed on Johnny’s face, and Billy had the look of disappointment.

“Too bad for you Billy”, Chrissy told him. “But at least you get to squirt, you just have to do it yourself”. The girls all laughed at him.

“Okay, down on the floor, both of you, on your backs”, Mommy ordered. “Billy, Johnny will squirt first as he is the guest. You may play with yourself in preparation, but do not squirt until told to”, she ordered again.

Billy watched with envy, as the girls knelt beside Johnny. He watched as each girl gave his penis a few loving strokes.

“Who do you want to make you squirt, Johnny”, Mommy asked.

“Whomever you think should, Maam”, Johnny dutifully replied.

But Johnny was staring at his sister. Mother could tell that he wanted his own little sister to make him cum all over himself.

“Okay, Chrissy, will you please do the honors..Kathy and Becky you play with his testicles and touch his belly while Chrissy makes him squirt”, She instructed.

Within seconds, Johnny let out a long moan, and said “I am cumming Chrissy”. The squirts were powerful, landing on his neck and chest, and there were so many of them. Becky was counting them out loud, and stopped at 12. Johnny just laid there, legs spread wide open, covered in his own semen..and muttering thank you to all the Females.

“Okay Billy, your turn”, Mommy said. “Put your legs up against the wall and point your peenie at your face”, she ordered.

Billy did as told, and the girls all kneeled around him to get a good view.

“Make it a good one Billy”, Chrissy said lustfully.

As was always the case with Billy when he first started to orgasm, his semen came out like pee, in a solid stream, not in squirts. He managed to get most of the solid stream of semen into his mouth. Then the squirt started, one after the other, some landing in his mouth, some on his face, and some were landing on the floor and his shoulders. His ejaculation finally subsided…

“Swallow all of it” Mommy ordered him.

Billy did as told.

“Now, go over to Johnny and lick all of his up, and swallow it as well, and also lick up any of your mess that got on the floor”, she ordered.

Billy did as told, as there were no other choices. His life was completely dominated by Mommy and the girls.

(End of File)