Author: The Naughty Gaffer brndtag at mcn.net.
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Title: Milton School – The Pajama Game  
Keywords: F/ffff, spank, petting
Summary: Boarding school girls continue several traditions.

Mrs. Brown has been at the Milton School forever, I guess. I know she was a student here because I saw her diploma the first time she took me to her office for a scolding. She seems even prouder of her Milton diploma than her Vassar diploma. I don’t think she has ever been married. I know that she has been the resident teacher for a long time, the teacher who lives in the apartment in the main building. Mrs. Brown roams around the grounds whenever school is out. Most of the time she’s just helpful, like a sorority house mom in the books I’ve read about college. She does a lot of help with homework and school projects. Sometimes she gets into our soccer and hockey games too.
A big part of her job, though, is discipline. Milton School doesn’t really have chores for girls to do since it’s a ritzy school and all the drudge work is done by the staff, but sometimes Mrs. Brown will give us a really nasty job. Sometimes Mrs. Brown will have us do lines or she’ll give us a scolding. Sometimes she makes us sit in the Quiet Room for an hour or so. If you get in big trouble, you wind up over her lap with a bare fanny getting warmed good. Really big problems get you a night in the Spare Room, where you get a special spanking and you spend the night in a kind of closet. Then you get another spanking in the morning before you go back to your own room. I haven’t been to the Spare Room yet but my roommate, Melissa, had to go there when she stayed too long on a town visit. Mrs. Brown found her in a store and brought her back. Melissa showed me her bottom the next morning and I decided I’d be on time from now on.
And we all know about the rules and the Spare Room before we start at the school. Part of the process is a visit to the school during your sixth-grade year. My mom had gone to Milton and so had her Mom. They had both been spanked a few times and Mom said nearly all the girls got spankings a couple of times each school year. She told me that Mrs. Brown was a new teacher when Mom started at Milton School and the resident teacher had been Mrs. Delaney (I guess she was a widow). Mrs. Brown became the resident teacher during my Mom’s last year at Milton. I guess Mrs. Brown must be getting close to retirement, but I’ll say one thing. I made the mistake of using bad language in front of my history teacher once and she sent me to Mrs. Brown’s room. Mrs. Brown warmed up my panties but good in just a few swats but I was lucky. She didn’t pull my panties down that time. I was going to try to be sure she never did.
Mom had told me a lot of stories about Milton before I ever went, mostly good stories but a couple of them were warnings about doing my work well and being cooperative (we don’t like the word “obedient” at Milton). When I was about to go back for my third year, she told me about a game that goes on at the school but it’s forbidden. It’s called the Pajama Game and Mom laughed about how she had played it sometimes. “Every year some girls think they’re inventing the Pajama Game,” Mom said and giggled. “But it’s been around a long time. I think maybe even Mrs. Brown played it.” Then she told me a little about the game and I could hardly believe Mom had played it, let alone Mrs. Brown.
It was in the winter of my fifth year at Milton that I found out. Melissa and I had just gotten ready for bed on a cold Friday night. The dorm leader had done room check to be sure everyone was in her room and I turned out the light. A little while later, there was a soft tapping on the door. I wasn’t sure I heard it until I heard Tabitha whispering, “Melissa! Melissa!”. Melissa opened the door a crack and Tabitha was there in her pajamas. “Come on,” Tabitha said. “We’re having a little party in my room.”
“Tabitha,” Melissa whispered, “it’s after lights out. If we get caught, we’ll all have to go to the Spare Room.”
“Naw, we can’t all fit. Besides, Mrs. Brown’s light has been out for half an hour. I’ve got some chips and some pop and stuff.” Now Tabitha was a problem girl and she was our year’s most frequent visitor to the Spare Room, so I should have known this was a bad idea. But it sounded like fun, so we sneaked out of our room and followed Tabitha. She got Marissa and Jody from their room and we went as quietly as we could back to Tabitha’s room. Her roommate Belinda was waiting for us, sitting cross-legged on the floor.
We sat on the floor with a couple of flashlights to see by and we passed the chips and the pop around. I don’t think even Tabitha would have had the nerve to bring booze or pot into the Milton School and I know I wouldn’t have stayed if she had. But it was Friday and Christmas vacation was starting the next week and we were ready to get pretty giggly even on soda pop. We were talking about teachers and boys and teachers and other girls and trying to keep whispering even when we were giggling so hard we almost wet our panties. After a while Tabitha stopped talking and put her finger on her lips so she could listen. She even opened her door a crack and looked out in the hallway. Then she sat down on the floor with us and waved her hands so we put our heads close together.
“My mom told me about a game that girls here play sometimes,” Tabitha whispered. “Older girls, you know. Our age.” Our age – we were fifteen and sixteen! “It’s called the Pajama Game.”
My heart jumped in my chest and I felt a strong pull in my stomach. I hadn’t quite believed Mom about the Pajama Game, but here was someone else who had heard about it. Heard about it and … she knew the rules!
“We can play it a lot of different ways, but we have to be real quiet because we don’t want to get caught.” I’ll say! My Mom had gotten caught once and she told me all about what had happened. “My mom said this was the way to start. We all stand up and we take off our pajamas and our panties. We throw them in a big pile on the floor and then I’ll say go. Then we see who can get her clothes back on first and who gets her clothes back on last. The last one with her pajamas back on has to do a forfeit and the first one gets to say what it is.”
“So it’s like Truth or Dare?” said Melissa.
“That’s right,” said Tabitha. “Game on, guys?”
If there had only been two of us, maybe I would have chickened out. But it was easier to swallow hard and feel the pulling in my tummy than to say I wasn’t going to do it. I wanted to try it anyway because my Mom had said it was really fun. So I nodded and the other girls did too. We got up and Tabitha was the first to take off her pajama top. She dropped it on the floor between the two beds and I looked at her for a minute. She had pretty big breasts with dark nipples. Her skin was really pale in the light and the shadows from the flashlights. I took my top off and the cool air in the room flowed over my bare breasts. They’re pretty small and my nipples are little pink things but I had learned to play with them in bed and I liked how I felt when I would rub them or pull on them. I put my shirt in the pile with Tabitha’s and made sure I watched where it was. I didn’t want to be last one dressed.
Melissa’s shirt was next. She has breasts about like mine, pretty small and really pink nipples. I knew that she liked her nipples too because I had heard her in bed when she played with them. Right then, I suddenly thought that she had probably heard me when I played with my nipples because I made little noises, too, even though I tried to stay really quiet.
The other girls took off their tops and dropped them into the pile and Tabitha was already taking off her pajama pants. I was wearing volleyball shorts for pajama pants and I was wondering if they would be hard to get back on in a hurry even as I untied the string and pulled them down. All of us looked very pale now in the flashlight beams and we had an interesting crop of panties on. I had plain white bikini panties, Melissa had black panties. Tabitha’s panties – the first ones on the pile again – had little hearts on them. Belinda had a pair of white panties a lot like mine but she’s bigger than I am. I saw Marissa taking off a pair of purple satin panties and Jody’s were leopard print. We were a little slow taking them off. I felt really funny when I pulled my white panties down in front of the other girls, even though we did it all the time in the locker rooms. But that was different. We all stood there, pale and naked and a little cold, and Tabitha raised her hand. “When I drop my hand,” she whispered, “get your pajamas back on as fast as you can.”
She kept her hand up a long time and I think she was looking at all the other girls. I know I was. I had seen Melissa naked a hundred times in our room but I was just now seeing that she was a very pretty girl. She had a slim waist and a cute belly button. She had just a little fringe of hair … down there, you know. I had a lot of hair, at least I had the most of the girls who were standing there waiting for Tabitha to drop her hand.
Tabitha dropped her hand and we all dove into the pile. Bare behinds were flashing in the flashlight beams and we were trying to giggle and whisper at the same time while we grabbed our own pajamas. Renee tossed Melissa’s panties out of the pile and Melissa called her a bitch as she scrambled naked on the floor to get them. I had been watching how the clothes fell on the floor when I wasn’t looking at Melissa or Jody (Jody’s breasts were the biggest in the room) and I knew just where to get my stuff. My shorts were a little hard to get into, but I didn’t want to be the first girl to have to do the forfeit. Belinda was even faster. I was starting to button my top when Belinda sat on the bed to show she was done. Jody and Melissa had gotten each other’s pants and had to swap them back. But it was Tabitha – she had been so brave about throwing her clothes in the pile first – who lost the first turn. Her top was at the bottom of the pile and it got pushed around a lot before she got a grip on it, so she had just put her arms in it when Jody sat on the bed, leaving Tabitha as the last girl standing.
“Darn,” she whispered and giggled. “I lost my own game.”
Belinda pulled her over to the bed. “And I won,” Belinda said. “So I’m going to be Mrs. Brown.” Tabitha took a second to realize what Belinda meant and then she lay down over Belinda’s lap. “Just be sure you keep it quiet,” Tabitha whispered. Belinda pulled Tabitha’s pajamas down, showing the little hearts on her panties, and she gave Tabitha about five soft spanks. I think she would have made them harder but she knew we couldn’t be heard. Tabitha wiggled and pretended to squeal and then she got up and pulled her pants back up.
“That was good,” Jody said. “Let’s do another round.”
It seemed easier to take our clothes off this time, but Melissa at least was still a little show when she took off her panties. Jody was the first one naked and I saw that her clothes might be hard to get to. When we were all standing naked in a circle again, Belinda said, “I won last time, so I get to say go.”
“Don’t wait too long, “ I said. “It’s kind of cold.” My nipples were standing very hard up and so were all the other nipples in the room.
“I’m going to add a rule,” Belinda said. “The last two girls have to do the forfeit.” I wondered what she meant by that but it turned out I was about to learn. We dove into the pile again. I grabbed my panties and wiggled them on, but I had a hard time getting my shorts. I finally got them and pulled them on, but when I looked up I could see Belinda had won again. I jumped up and started buttoning my top when I realized that Jody had just sat down and I was last.
I wasn’t sure about this. I didn’t really want Belinda to play Mrs. Brown on me. Or did I? When I thought about her swatting my panties, I felt excited and my nipples pushed up, but not because of the cold air. Besides, two of us were going to have to do the forfeit. What did Belinda want us to do?
“Okay,” Belinda said. “Jody and Heather, you have to take off your tops. And kneel facing each other.” I unbuttoned my shirt and took it off and Jody did too. We got on our knees on the floor, facing each other and with our hands on our knees, and waited. Then Belinda said, “Heather has to kiss Jody twice.”
I put my hands on Jody’s bare shoulders and leaned my face toward hers and then I heard Belinda say, “Once on each nipple.”
Where? I couldn’t help smiling a little even though I was a little scared. Jody raised her shoulders and her breasts and I put my face lower. I kissed her left nipple and then her right, but Belinda said, “A real kiss. That was a grandma kiss.”
So I had to do it again. Jody’s nipple was a little cool in my mouth at first, but I put my lips around it and touched it with my tongue. She made a little noise and I felt her nipple stand up more. Then I moved to the left nipple again and kissed it hard. Jody whispered in my ear, “That was good. Maybe I’ll lose on purpose next time.”
“Now Jody has to kiss Heather the same way,” Belinda said.
I liked touching my nipples and Jody had liked when I kissed hers, so I thought this could be pretty cool. And it was. Jody went for it on the first try, putting her mouth all over my left tit and even licking my nipple – I had just touched hers, not really a lick. I didn’t quite realize when she let go of my left breast and she kissed all over my right breast too.
“I like this,” said Melissa. She had been watching with big eyes. “Are we going to do it again?”
“Right now,” said Belinda. When she said “Go”, our clothes went flying. We tried hard not to giggle too loud when we took our clothes off this time. I was watching Belinda as she peeled off her pajamas and pulled her panties down. She had a really nice looking bottom, I thought. It was round and cute.
Somehow I got Belinda’s panties this time and she got mine. I was just taking hers back off when I knew they were too big, but she had some trouble getting out of my panties because they were small for her and she had put them on so fast she didn’t even know it. We were both still naked, trying to figure out our panties, when Melissa sat on the bed and we were the last ones standing. Tabitha had won that time and when I started to put my panties on, she said “No, you two stay naked.”
We stood side by side, naked, in front of the other girls while Tabitha bit her lip, thinking. Then she said, “I’m going to tie you together and you have to get loose.”
Tabitha got a bathrobe sash and pulled Belinda and me together, belly to belly. It was strange and it felt good at the same time, feeling our breasts and our tummies pushed together. When Tabitha tied us around the arms and the waist, she made sure to tie around our bottoms too so we had our hips tight together.
Our arms were by our sides and the knot on the sash was about at my belly button. We had to wiggle around to raise the sash until we could reach the knot and untie it. I liked feeling Belinda wiggling her bare skin against mine and I had a hard time concentrating on getting free, but we finally got loose again. By then the other girls were staring at us, but as soon as I got the sash free, Tabitha started pulling off her clothes again. Soon we were all standing naked, waiting for her to drop her hand.
This time I wound up being dressed first. Melissa and Tabitha were the last ones and I thought they did that on purpose. When I was sitting on the bed, it looked like they were waiting for the others before they really tried to get their pants and their shirts on.
“I get to say the forfeit,” I said. I didn’t really have any ideas and I couldn’t remember the ones my Mom had talked about, but I got an idea. “You two have to get naked again,” I said. They looked at each other and they took their pajamas and their panties back off. “Now kneel here over the bed, side by side,” I said. They knelt down with their bottoms out and I pushed them close together. I had liked the feeling of a naked girl so much that I wanted them to get to feel it too.
“Now, everybody else, kneel behind them,” I said. When everyone was ready, I leaned forward and I tickled Melissa’s feet. I knew she was really ticklish. The other girls started helping right away and we tickled our naked friends for about two minutes. They had to put their faces into the blanket to smother the sound of their laughing and I saw they kept pushing their bare sides against each other, especially their bottoms.
I had just quit tickling Melissa and Tabitha and they were buttoning their tops when the door opened and the light came on. Mrs. Brown stood in the doorway and my heart sank like the Titanic. We all sort of froze where we were and I know my mouth was gaping like a fish.
“Well, yes, the Pajama Game,” Mrs. Brown said. “I’m quite sure you all know what this means.” She motioned for all of us to stand up and she sat on Tabitha’s bed.
Mrs. Brown lined us up by age, which made me next to last and Tabitha was first. She pulled Tabitha over her lap and pulled down her pajamas and her panties with one motion. Twenty spanks later, Tabitha’s bare bottom was a light pink and she was kneeling on the floor. Belinda followed too fast and it was my turn.
I had only had a panty-warming before, but this was a lot more sincere. Mrs. Brown pulled my pajamas and panties down like the other girls and I was surprised to find out I was more excited than scared. She gave me twenty spanks too and it stung, but each time I felt her spank my bare bottom I felt a rush too. She had me kneel on the floor and I watched as she pulled Melissa’s panties down and warmed her bare bottom too.
Back in our rooms, we put a little cold cream on the pink spots (of each other) and got into bed. After I had played with my nipples a while, I put my hand under my panties for the first time and I played there too. It felt really good and I fell asleep happy, even though my bottom still knew the admission price to the Pajama Game.