Grandma's Diary

By NAMB

modestnot@gmail.com

Copyright 2022 by NAMB all rights reserved

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This story is intended for adults only. It contains depictions of forced nudity, spanking, and/or sexual activity of preteen and young teen children. This is fantasy, and the author in no way endorses or practices these things on real life. If you are not of legal age in your community to read or view such material, please leave now. 
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Grandma’s Diary

I was really said when grandma was killed by a drunk driver. It felt funny going through her house after the funeral. It both reminded me of her which made me happy, but it also reminded me that she was gone.

Most of her possessions were either distributed among family members or donated to charity. My aunts and mother and older cousins seemed to get most of her jewelry. I got some earrings and a bracelet.

The real treasure was in the attic. She had a stack of old magazines that we sold to a bookstore for a bit of money. They were from the 1960’s and featured articles on the first man in space, JFK’s assassination, the Beatles, the Vietnam War, Peace Marches, Civil Rights “Freedom Rides.” Woodstock, the moon landings – all told as they were happening.

At the bottom of the pile was a diary. It was agreed that I should have it by default. As the youngest member of extended the family, there wasn’t much else left to trickle down to me. But it was hers and that’s all that mattered. It had a lock on it, and I had to work diligently with a paper clip to pick it.

The first entry was

----- Diary Begin -----

August 18, 1961 (Friday)

Dear Diary,

B – My name is Barbara.

Hello and Happy Birthday to me. I’m 11 years old today! You’re the first gift I opened.

Mom tells me that I have to wait for my party tomorrow to get the rest of my presents. However, dad surprised me. Mom held her hands over my eyes while daddy led me slowly and carefully down the stairs to the basement. When mom uncovered my eyes, there it was! A new bicycle: pink and everything. So that’s why I didn’t get to you until bedtime. I just had to ride it and show my friends Judy and Carol.

-----Diary End ---

This was interesting. I just turned 11 myself so it’s like grandma and I can compare notes. Her words at my age bonded us together. I am so glad I found her book.

I decided that I would follow in her footsteps and since she wrote it one day at a time, I would read it one day at a time. Furthermore, I decided to put it down for about a week so I can read it on the same day she wrote it 60 years ago. I had to “offset” it by a couple days so I was reading it on the same day of the week that she wrote it.

----- Diary Begin -----

August 19, 1961 (Saturday)

Dear Diary, today was my official party. We had it over Aunt Mary and Uncle Carl’s house. They aren’t really my aunt and uncle, but my parents and them all grew up on the same block on the Lower East Side of New York during the depression and my dad and Mr. Miller served in the same unit during the war.

We had the party there because they have a pool. It’s a big round thing about three feet deep. I don’t know how many of us kids we managed to fit in there, but it was nearly empty by the time we all got out with all the splashing we did.

I suppose I should introduce you to Raymond. Raymond is 13, he’s always sort has been a big brother to us, but not always a nice big brother. Up until just before summer started, I was going through a “fat” phase and I had pimples everywhere. Raymond and his friends made fun of me and it really hurt my feelings.

I think Aunt Mary got after him for it. He doesn’t pick on me as much now which is kind of good because he’s really cute.

I don’t know why I should bother. He won’t be going to Saint Ann’s anymore, he’s going to high school in a couple of weeks so I probably won’t seem him a lot and I don’t think he’d even look at a little girl like me especially with so many teenager girls that he’ll be going to school with.

You also need to meet Betty who is Raymond’s big sister. She’s already 17 and will be going into her Senior Year in high school. I like Betty a lot. She’s babysat for me a couple of times. She’s really nice. She is definitely like a big sister to me. I want to be like her when I grow up.

We kids were in the pool for almost the whole party. I got to see the O’Donnell twins: Billy and Jimmy naked. They’re only 5 and haven’t even started school. Their mom changed them right out in the open and they didn’t even seem to mind. I would have been so embarrassed.

I guess things are different if you are a boy. Their pee-pees seemed very small. I was too far away to get a good look, but I don’t know what the big deal is.

We only got out of the pool when it was time to eat and then have my cake and then I got some more presents.

In addition to you, and by bicycle, I also got other books too. One of them in a Nancy Drew mystery, another is a Joke book and Aunt Marion gave me a Romance Novel!

I like Aunt Marion, she’s the youngest of my aunts by a lot and is more like an older cousin or maybe an older sister than an aunt. She doesn’t treat me like a baby.

I also got a couple of skirts, a couple of sweaters and a very pretty blouse.

I got to go. It was a really busy day and it’s late and mom is telling me I have to go to bed.

-----Diary End ---

Raymond? So grandma had a crush? I’m beginning to notice boys differently too. It’s really tough to think of grandma as anything other than an old lady. Yet I’m beginning to relate to her as if she were a girl like me. I wondered that if she were 11 now, if we’d be friends.

I read several more chapters of grandma’s life. It was mostly about starting school, hanging out with her friends, going to church, a fire in the neighborhood and a trip to the movies.

Things got racy when I got to September.

----- Diary Begin -----

September 8, 1961 (Friday)

Dear Diary, I GOT TO SEE RAYMOND NAKED! I wish I had time now to tell you all about it but I’m too jumbled up inside and anyway it’s almost midnight and mom is insisting on me going to bed. I don’t know if I can sleep.

-----Diary End ---

Although I could look ahead, I resisted the temptation. Like grandma, I had a tough time sleeping that night.

----- Diary Begin -----

September 9, 1961 (Saturday)

Dear Diary, Last night was amazing! It all started when I went over to the Miller’s for the evening. My parents and Aunt Mary and Uncle Carl go bowling on Friday nights, so my parents drop me off and Betty “babysits” Raymond and me.

I’d hardly call it babysitting. Raymond doesn’t like being looked after by his older sister, but to me it’s almost like a pajama party except without the pajamas and actually sleeping over – as if me and my friends ever actually slept at a pajama party.

Pizza was the mainstay, of course. What else do good Catholic families eat on Friday? There’s also a lot of other snack food to eat.

Raymond usually commandeered the TV while us girls would sit in the kitchen and gossip.

Tonight it started out that way, but I found it odd that Betty ordered Raymond to go into the TV room and stay there until she called for him.

Then she turned to me. I could tell by the look on her face that she had something serious to talk to me about.

She asked me if she could ask me some private questions and made me promise that I would keep them a secret and that she would keep my answers a secret.

Her first question was if I knew what boys looked like. Of course I did, we all saw the O’Donnell boys at my party.

She said that she meant older boys. I swore her to secrecy but Judy and Carol and me made Tommy Nash make pee for us when we were in the first grade. That was 4 years ago.

She kept pressing and asked me if I saw older boys. I told her no. I was wondering where she was going with these questions.

Then she asked if I knew what an erection was. I didn’t then she asked me if I knew what a hard-on was. I heard of the word and I knew it was something to do with boys and their things, but I didn’t have a clue.

So she explained to me how boys penises – that’s what she called them – got hard and big sometimes.

I asked her why they did that and she told me that it had something to do with ejaculation.

I asked her what ejaculation was and she said it was when semen comes out of a boy’s penis.

Then she asked me if I had a talk with my mom about how babies are made. I said that I didn’t.

She said that I would probably learn about this in school this year anyway and told me that when a man likes a woman a lot, his penis gets big and hard and he puts it in the woman’s vagina and rubs it around and then the sperm comes out or ejaculates into the woman and makes it way to the egg and fertilizes it and that makes the baby which grows inside the mother until it is born.

It all sounded kind of gross to me, but she said that it’s fun for the boy and if he does it right, it’s fun for the girl too.

I still felt funny. I can’t imagine something as big as a penis going into my vagina, much less a baby coming out.

Got to go. Mom is calling me for something.

-----Diary End ---

Fortunately, the next entry was for the same day, so I could keep on reading.

----- Diary Begin -----

September 9, 1961 (Saturday)

Mom wanted to know if I wanted to go shopping with her later today.

Now where was I, Dear Diary?

Betty was telling me about stuff about boys that I never knew. It made me feel funny, but it also made me feel good. I’m glad I know all this stuff.

I told her that I couldn’t wait to tell my friends about this but she reminded me that I promised to keep it a secret. Then she changed her mind and told me that I could tell them everything she told me up until then. The parts about how babies are made.

She said that all girls needed to know about this stuff but to be careful who I told.

For the next part, she made me double-promise to keep it a secret.

She asked me if I knew what queer was. Again, I had heard the word, but I really didn’t know what it meant. She told me that it’s another word for homosexual. That was another new word for my vocabulary.

She told me that queer means boys who like boys. She also told me that it also means girls who like girls.

I wondered where she was going with this and asked her why she was telling me this.

She took a deep breath and swore me to secrecy again.

“It’s about Raymond,” she started.

She told me how she planned to take the train to Manhattan and go to the museum with her friend Alice for a school project they were working on but when she got to Alice’s house, Alice was sick so Betty stayed with her for while and then went home.

She said that she must have been gone about an hour. When she got home, she found Raymond in bed with Alex Manchester. Both of the boys were naked and both had hard-ons.

She made Alex get dressed and sent him home. She made Raymond keep his clothes off.

Raymond was in tears begging her not to tell their mom and dad.

After Alex left, she had a talk with Raymond.

She told him that she loved him and that she wanted to help him be normal but he had to do everything she told him to do.

She told me that she thought it would be a good idea for him to be naked in front of girls and have the girls do things with him to make him feel good about them.

Then she dropped the bombshell. She asked me if I would like to be the first girl (besides her) to see Raymond naked. She said she might show him to some of their cousins, but that would take some time to arrange.

I didn’t know what to say. So she said, we can start right now and that all we will do is make him take his clothes off for now. She told me she had other ideas for him but had to think about them.

So we went into the TV room and she told Raymond to turn off the TV and then take off his clothes.

He said he didn’t want to because I was there.

Betty told him that I was “mature.” That made me feel good.

She threatened him saying that she would tell their parents if he didn’t do it.

So he got undressed. I could see EVERYTHING!

She made him stay naked until just before our folks came home from bowling.

When mom and dad came to pick me up they asked if I had a good time. I sure did. I can’t wait until next Friday night.

-----Diary End ---

Way to go, grandma! Since I am taking this one day at a time, I’m going to have to wait until next Friday too.

I can’t believe that grandma didn’t know about how babies were made. My mom told me about that a long time ago.

Also, I knew what boys looked like since as long as I can remember. My mom gave be a boy-doll when I was a little girl and it had “all the parts.” Also I had seen some of my friends little brothers running around naked.

----- Diary Begin -----

September 10, 1961 (Sunday)

Dear Diary, Mom and I went shopping yesterday. I got a sweater and a new pair of Keds.

Today was Sunday and we went to mass. We passed by the Millers as we made our way to the pew. Betty smiled at me and winked. Raymond just blushed and looked down. I don’t think he can look me in the eye after I’ve seen him naked.

Mom wanted to know if I felt sick because I did not go up to receive communion. I told her a little bit. I can’t tell her that I couldn’t receive because I committed a mortal sin by seeing a naked boy.

I mean, it’s ok if the boy is little and doesn’t know any better. That got me thinking, what age does a boy have to be so that when a girl looks at him, it becomes a sin and then is there an age when it goes from being a venial sin to a mortal sin?

I even felt funny looking at the O’Donnel boys and they’re little. Besides their mother made them do it, so I guess that makes it OK.

Religion is a very complex thing. The Baltimore Catechism doesn’t address this issue and neither do the nuns at school.

I better make sure I go to Confession next Saturday. I’ll try for Father Ryan, he gives the easiest penances.

Dad took us to see Aunt Clara on Long Island after church. We didn’t get back until almost dark.

-----Diary End ---

My very Catholic grandmother. She did bring up a good question. I don’t think looking a naked boys or naked anyone is a sin as long as everyone including the naked person is OK with it

I mean, if some dirty old man flashed me, that would not be my fault.

So I wondered about Betty. I am not sure how OK Raymond is with being naked.

Betty was 17 years old and almost an adult. Her position as “babysitter” conferred her with a certain degree of authority. She was using her authority and blackmail to make her brother do something he didn’t want to do. Was she committing a sin?

I also wondered about Raymond. Normally a 13-year-old boy would know better than to expose himself to girls and one of them a younger girl. I suppose he could be forgiven since he was being forced into doing it. I think he was really scared of his sister and was afraid to stand up to her.

That left grandma. Was it a sin for her? How much control did she have? Betty had almost as much control over her as she did Raymond. The peer pressure must have been tremendous. Of course, being “forced” to look at Raymond naked probably absolves her of blame.

I wonder what I would have done in her place? Could I resist seeing a naked 13-year-old boy, especially when he’s being served up on a patter and I’m being urged to see him? At no time did Betty ask grandma if she wanted to see Raymond. She just assumed grandma wanted to see him. The only thing she did was swear her to secrecy.

----- Diary Begin -----

September 11, 1961 (Monday)

Dear Diary, it’s Monday. I really didn’t feel like going to school today, but a girl does what a girl must do.

On my way to school, I saw Raymond waiting for the bus to take him to school. I waved at him and said hello. He just mumbled a hello back and did his best not to look at me.

I felt a little bad for him. I know I wouldn’t want him looking at me after he saw me naked, so it must be very uncomfortable for him. I decided I would play it cool. I would never say anything to him about it outside of Friday evenings.

I met Judy and Carol at school. I wanted to tell them everything, but I decided to tell them nothing until after school. They would pester me to no end if they thought I had some secret to tell them and didn’t.

The day went by very slowly for me and I had a difficult time paying attention in class

I dropped the bomb on them as we walked back from school. I told them that Betty told me a lot of stuff about boys and how babies got here.

It was difficult to tell the story because they kept interrupting me but if they paid this much attention in class, they would be A students.

None of us girls was naive enough to believe in the stork theory but we did have misconceptions about conception. We vowed that we would do our best to tell other girls so they would know, too. This is something all us girls need to know.

I wanted so much to tell them all about Raymond, but I promised Betty. Besides I didn’t want them to think of me as “that kind of girl.”

-----Diary End ---

I was really sympathizing with grandma. I felt like I was in her shoes (or Keds – did girls really wear them back then?) I don’t know if I have the same will power that she had at my age. She always seemed to be a wise woman, but that was the older grandma, the one who was mother to my mother.

When I think about my best friends, Emily and Patsy, I don’t think I could keep such a big secret from them. I don’t know how grandma kept a lid on it. She was playing it so cool. I decided if she can do it, I can do it.

The rest of the week revealed more routine stuff about school. It seems like grandma disliked tests as much as I do. One more way in which we bonded. I had to wait until the following Saturday so she could fill me in on what she and Betty did the night before. I soon caught on to the fact that she was picked up rather late on Friday nights and sent to bed as soon as she got home.

----- Diary Begin -----

September 16, 1961 (Saturday)

Dear Diary, I you thought last Friday night was exciting, wait until you hear what Betty and I made Raymond do last night.

Well, I didn’t make him do anything. Betty is the one who is in control of him, but I got to watch. She says she thinks it’s a good idea for him to be naked in front of me. She says it will help “Turn him around” to have experiences with girls.

I asked her about these “experiences with girls” and she said that she and Raymond have an older cousin, Louise who is a nurse.

Betty told me about Louise. When she and her fellow students were in nursing school, they went through the various wards in the hospital. One of them was urology or as the nurses called it “the Penis Palace.” I giggled when she told me that.

Betty said that Louise told her that it wasn’t all that great, because most of them were old men, but every now and then they’d get men in their 20’s or 30’s. The nursing students learned a lot from their instructors on men’s parts and how they work and what could go wrong with them.

They also learned a lot more from the older nurses who had been working on the ward for a number of years. Those women probably saw more penises in their lifetime than anyone else and they taught the students a few things not in the official course of instruction for the nursing program.

She says Louise told her about a thing called masturbation or jerking off.

I didn’t know what she meant by either of these things, but I do recall hearing one boy accuse another of jerking off and the other boy got mad at him.

Fiddlesticks! Mom’s calling me again. Every time I have something to tell you she seems to know about it and interrupts me. Stay tuned to this station, dear diary, I’ll be back.

-----Diary End ---

This passage was an eye-opener for me. First of all that even Betty didn’t know about masturbation. It’s something I learned about last year in Human Development Class. I guess they didn’t teach that stuff in Catholic School back then.

The other thing was attempting to get Raymond to “turn around” his homosexuality. We also learned that homosexual is something you either are or aren’t. Also, having a homosexual experience, especially in the teen years, doesn’t make one a homosexual for life.

It makes me wonder about myself. I feel a physical attraction for some of the girls in my class. I have no problem hugging and kissing my friends. Even though it feels good when I do these things, I don’t think I want to do anything sexual with them.

I think this is one advantage us girls have over boys. We can show physical affection for one another more easily and people don’t look at us funny when we do.

----- Diary Begin -----

September 16, 1961 (again)

Dear Diary,

Mom told me that Aunt Mary is coming over to measure me this afternoon. It seems that I have grown out of my school uniform and that the skirt is now too short for the nuns at St. Ann’s. So she’s going to let the hem down before I get in trouble for giving boys “impure thoughts.” I envy girls in the public school who can wear their skirts shorter.

So where was I? Oh yes, Betty was telling me about masturbation.

Last week she told me about how babies were made. The man has to put his penis in her vagina and deposit his sperm. Apparently, the man has to make his penis hard so it will go in and then he has to rub it around inside the woman to make the sperm come out.

I’m not sure I like that idea, but if I want to be a mom and have children of my own, I’m going to have to go through it.

-----Diary End ---

I am glad that grandma got over her reluctance to intercourse or I wouldn’t be here. I don’t know who had a tougher time with the thought of intercourse: grandma because she had to do it with a boy or me because I know she did it with grandpa. Knowing that your grandparents and parents “did it” is not a thing that any kid wants to think of. I feel a little better about grandma. Through her diary, she’s more like a friend separated from me by 60 years.

----- Diary Begin -----

Betty says that this feels good for the man. But boys Raymond’s age don’t have wives so they can’t do it. Instead they do masturbation.

She told me that they use their hands to play with their penis to make it hard and then make the semen come out.

She tried to explain it to me, and I had all kinds of weird ideas in my head about what this might look like. After a short while, she could see that I wasn’t getting it and gave up and said, “I put this off too long. Why don’t we just have Raymond show us?”

“Raymond, get undressed and show Barbara and me how you jerk off.”

Raymond knew that it was futile to resist his sister, so he simply complied without complaint.

It was nice to see him naked again. I don’t think I could ever see him again without the image of him being naked again popping into my head. Given the way he looked away and blushed all last week when I saw him, I think he knows this too.

He started to walk towards the kitchen.

Betty asked him where he was going and he told her that he was going to the bathroom.

She asked him if he had to pee and if we could watch him do it. He said no, but the bathroom is where he usually went to “jack off” as he put it.

Betty complained that the bathroom was too small for all of us to watch comfortably. He said that he sometimes did it in his bedroom.

With that negotiation over, we followed him to his bedroom. I liked looking at his backside. It’s so muscular.

When we got there, he sat down on the bed and asked if we wanted to see him do it wet or dry.

Betty asked him what the difference was.

He explained that to do it wet he needed baby oil or hand lotion or something slippery and the dry can be done at any time anywhere.

Betty and I took a vote and we decided on dry and have him do wet next time. We didn’t want to take the time out to get something slippery for him.

He wrapped his hand around the shaft of the organ and pulled the skin up so it went over the top and then pulled it all the way back. He did this over and over picking up speed as he went on.

Whatever he was doing, he was making it grow. It looked like it was getting bigger. Betty caught on and made him stop.

She told me to look too. She said that must be an erection. I came in for a closer look. His penis was bigger and it was stiff enough to stand up all on its own.

Betty nodded to him and told him to keep going and he started pumping again.

He was at it for a while and then he started breathing funny. His body got stiffer and he seemed to shake. He started to pant, then held his breath. His entire body got rigid and then he let out a loud moan.

I was concerned. I thought he was getting sick.

Then this jet of white stuff shot out of his pee hole. At first it surprised me but then he did it again and again and again for about a minute.

Raymond collapsed. He laid on the bed like a rag doll.

“Is that sperm?” I asked.

Betty said that it must be.

From what I heard, I expected that it would come out like pee. I didn’t think would come out in spurts.

Betty was curious about it. She told me that it would probably be safe for us to touch it with our fingers and that we wouldn’t get pregnant by doing it.

It looked dirty and slimy to me, but Betty went right for it wiping at a glob of it that was on his stomach. She brought it up to her nose and sniffed at it.

She put her finger to my face and asked me to smell it, too. I really didn’t want to get that close to it, but I didn’t want her to think I was chicken so I took a sniff.

I expected it to smell like pee. Instead, It had a faint odor and smelled sort of like raw egg. I told this to Betty.

She rolled the droplet around with her fingertips and said that it sort of felt like raw egg: slippery and sticky at the same time.”

Raymond lay there for a while and after a while cleaned himself up with some Kleenex. Betty and I both watched as he took a shower to clean off. We kept him naked for the rest of the evening.

-----Diary End ---

OK, I’m wet. Wow, grandma! I heard about masturbation, but she actually saw one! I am so envious. I can’t wait until I can get some boy to do that for me. So that’s how boys do it. It kind of makes sense. They boy is using the skin on the shaft of his penis to simulate a vagina.

I wonder what the wet way is like. I guess I’ll have to wait until next week, too. Although my Human Development Class mentioned masturbation and even gave a definition of it: “stimulation of the sexual organs exclusive of intercourse,” it never got into details.

I wondered how boys “do it.” I still do. I wish they had smart phones back in grandma’s day then maybe she could have taken a picture. I think her verbal description is good enough so that if I ever saw a boy doing it, I’d know what he was doing.

If boys like doing it so much, then why don’t they let us girls watch?

I thought about that during the week.

I liked reading grandma’s diary every day. The Saturday morning (I presume) entries were the raciest. During the week she seldom mentioned Raymond, except to mention that she saw him playing stickball with some of the other boys or doing some other activity after school.

Mostly she talked about school and repeated some girl gossip such as one of her classmates telling her that her older sister started her period. Occasionally, there would be a mention of some girl she knew having a crush on some boy. She would also report about hearing a new song on the radio or seeing a movie.

Even these everyday entries gave me an insight into the way things were back in her day and I got to know her. There were some differences but through her diary I found out that girls back then pretty much talked about the same things that girls talk about now: clothes, music, movies, school, other girls and, of course, boys. I really believe that if I were alive back then or she was alive today and my age, that we would be best friends.

I kind of wish that I could go back in history so I could tell her a lot of things. I also wish I could hang out with her on Friday nights. I wish I had a friend as sexually adventurous as she was. I don’t think I have the nerve to be around a naked boy on my own. I’d need someone for moral support.

----- Diary Begin -----

September 23, 1961 (Saturday)

Betty already had Raymond naked when I got there. She had him hiding in his bedroom in case my parents came in. They normally just dropped me off at the door and Aunt Mary and Uncle Carl would pass me in the hallway.

Last night was special. Betty said that her dad had to work late and her mom was meeting him at the bowling alley to grab a bite to eat before the games started.

She told me that she couldn’t wait until I got there so we could get our games started. So we went to Raymond’s bedroom. She opened the door without even knocking.

She wasted little time. “Barbra and I want to see you masturbate again. This time we want you to show us how you do it the wet way.”

Of course I wanted to see it, but the way she phrased it, she made it sound like my idea.

“I need something slippery,” he replied.

“Like what?”

He told her that he used baby oil. He explained that it was so messy that he did it in the shower. He could wash everything off after he did it. He said that it was also convenient to do it there because the baby oil was in the cabinet under the sink.

He also mentioned that he was concerned because his supply was running low.

She told him that he could always buy more and he said that he didn’t know where to buy it and that he would be ashamed to buy it because somehow they would know the reason he was buying it.

“Stop being such a baby,” she told him.

She then asked him if there was something else he could use and he said “anything slippery.” She told him that he could use her hand lotion and she could keep him supplied with as much as he needed.

He asked if he could use it now and she went and got it.

We all crowded into the bathroom.

“So how do we do this?” she asked.

He held out his hand and had her squirt a large drop into his palm. He then told her to put some on the shaft and head of his penis,

-----Diary End ---

I was taking mental notes. Someday, I might have the opportunity to do this with a boy and I want to know how to do it.

----- Diary Begin -----

Raymond started pumping. He said that it was not as slippery as the baby oil, but felt really good he also added that it was not as greasy as the baby oil and would be easier to wash off when he was done.

Betty laughed and told him to leave it on because it would make his skin soft and smooth.

I tried to remember how he did it last week. Then the head of his penis would disappear under the skin of his shaft when his fist was fully forward. Now his hand slid up and over the head without skin in between.

This was probably more like the real thing. I doubt that the skin on a boy’s penis bunched up as he rubbed it inside a girl’s vagina. The penis probably makes direct contact with the girl’s skin in there. That thought made me feel funny inside. I was trying to imagine what that would feel like for the girl.

The wet way was also accompanied by a noise, a sort of “slicky-slicky” sound it sounded weird, but it also excited me.

I watched as his penis moved in and out of his fist. It seemed even bigger and harder than it did last week or maybe it was my imagination. It certainly was easier to see this way.

Just like last week, he stiffened up and stopped breathing and then his semen came out. He shot it all the way across the tub! I wondered how far that was and how much he shot. He seemed to shoot it faster this time

Maybe I’ll talk to Betty about this and we can figure out a way to measure how far he can shoot it and how fast he can shoot it. I think I can talk her into it.

He kept pumping until no more was coming out. He said that he didn’t think he needed to take a shower because the hand lotion was easier to wash off than the oil. We watched as he cleaned himself off with the washcloth.

OK Diary, I think that’s enough for today. I can’t wait to see what Betty will make him do next week. Watching her make him do things and being able to watch him made me feel so good to be a girl!

-----Diary End ---

Reading what grandma had to say made me glad to be a girl too! Wow. When this started, I felt that I knew more about sex than grandma did, now she’s in the lead. She and Betty were in charge of a boy! How I envied her!

----- Diary Begin -----

September 30, 1961 (Saturday)

Dear Diary, the days are getting shorter. It was almost dark when I got to the Brown’s house.

Betty made Raymond get naked for us again. I am getting more comfortable with looking at him like this. I think most of the excitement is that we girls got to keep our clothes on while he, the boy, had to take them off because we, the girls, told him to do it.

I think Sister Mary Angelica would like the way I conjugated that sentence. I like her, she’s nice and English is my best subject. But I don’t think I’ll let her read you.

We made Raymond jerk off for us again – he did it the dry way and then Betty wanted to talk to him.

She asked him how long he was playing with himself like that and he replied that he started when he was about 8 years old but did it by rubbing his penis against the mattress. He said that he didn’t squirt anything until he was about 12 and then it got too messy to do it that way.

He heard about jerking off but didn’t know what it was, but by experimenting by himself figured out how to do it.

“So tell me about you and Alex?” She asked.

“It all started when I stayed over his house about a year ago.” Raymond went on to explain how they got to talking about if they “did it” and eventually they confessed to each other that they did.

Raymond said that it was very difficult for them to admit that to each other. Boys don’t like talking to one another about it.

And now, he’s telling his sister and me!

He said that one thing led to another and pretty soon, they agreed to watch each other do it. He said that they managed to get together a couple of times since then to do it together but they never touched each other until the time Betty caught them.

“There’s no telling how far you would have gone if I hadn’t caught you. Have you done it with him since then?”

“NO!”

She told us that she had an idea. It was a tip that she learned from babysitting. If a kid didn’t want to go to bed when you told him. You told him OK but then you keep him up until he’s tired. You keep making him stay up until he begs you to go to bed. Then you can make him promise that he will go to bed when you tell him from now on.

I’ll have to keep that in mind when I get to be a babysitter.

She then went on to say that in order to cure Raymond of being queer that she would make him do queer things until he didn’t want to do them again.

She told him to tell Alex that she wanted to see him and that she would tell his parents what she caught them doing if he didn’t obey.

Tell his parents that he’s coming here so you can play games together and that there will be adult supervision – me.

I’m going to make you two do what I caught you doing and then I found out about this other queer thing I can make you do.

Raymond asked what the other thing was but Betty said that he would find out when the time came.

I could not believe it! I was going to see Alex naked too.

We watched some TV and played cards and then made Raymond jerk off again. As I watched him I wondered how Judy and Carol were spending their Friday nights. I wished there was a way I could have them here with me.

-----Diary End ---

I wish I could be so matter-of-fact about naked boys jerking off for me as Barbara was. By now and through her diary, I felt like she was one of my friends so from now on, I’ll call her Barbara even though in my mind she’ll be “Grandma Barbara.”

I was also beginning to feel like I was getting to know Raymond. I felt sorry for what he had to do, but it wasn’t all that bad. It wasn’t like Betty or Barbara were really hurting him. Sure, it was embarrassing but at least they were keeping it to themselves.

----- Diary Begin -----

October 7, 1961 (Saturday)

Dear Diary,

I GOT TO SEE MY SECOND NAKED BOY LAST NIGHT! I expected that all boys look alike and that if you’ve seen one, you’ve seen them all. It seemed like that with the O’Donnell boys – Jimmy’s little dinky looked just like Billy’s little dinky. But that doesn’t seem to be true with bigger boys. I can tell the difference between Alex and Raymond just looking at their penises. But I am getting ahead of myself.

Alex was already there when I arrived. Both boys were still dressed. Betty told me that she would wait for me. She said that it would do Alex some good to get undressed with two girls watching him.

I suppose she is right. I wondered how he would feel if I walked in on him while he was naked. But he should be used to that. Betty already caught both him and Raymond naked.

I guess Raymond or Betty must have explained to him what was going on because he didn’t seem to have any questions.

He was upset that I was there and didn’t want me seeing him naked. I don’t know why, Betty was going to see him naked, so what difference does one more girl matter?

-----Diary End ---

Sitting back all these years later and in a city halfway across the country, I think I can see Alex’s point. Being caught naked is very embarrassing, but being made to get naked as other people watch is makes the embarrassment that much stronger.

Also Betty was 17. She’s almost officially an adult. I am sure Alex realized that she was probably babysitting for several years already and probably had seen more than her share of naked little boys and their boy parts.

But Barbara was a younger girl. She had no right to see him naked under any condition.

----- Diary Begin -----

Betty made Raymond get naked first. I think that’s because he was beginning to get used to it. Also seeing another boy naked probably made it easier for Alex.

Anyway, after a bit of a delay, Betty and I had the pleasure of seeing two naked boys.

Betty wasted no time ordering Raymond to jerk off for us (dry again). I guess that was also for Alex’s benefit.

Then it was Alex’s turn. I expected him to do it the exact same way as Raymond, but it was all different. Well, it was basically the same. He used his right hand and a pumping action like Raymond, but he seemed to have gripped his penis closer to the head and he pumped more slowly. Also he worked his balls with the fingers on his free hand.

He also took longer to squirt his stuff but when he did it looked like there was more of it and he shot it further.

His body reacted differently than Raymond, but I could tell when he was ready to squirt.

We made the boys clean up their messes and we all went inside with the boys still being naked. Betty let them put on their sweatshirts since the apartment was cold.

I was expecting Betty to make the boys jerk off again at the end of the evening, but she had a surprise for all of us. She made the boys stand facing each other and grabbing each other’s penises. She then ordered them to jerk each other off.

She told the boys, that she caught them doing this, so they should already know how to do it.

Raymond told her that although she caught them touching each other, they never got as far as jerking each other off.

I don’t think either boy wanted to do it, but Betty insisted.

It was funny watching them touch each other. This time it took more time than even Alex took. Maybe because it was the second time for each boy. Raymond seemed to take more time the second time around. Or maybe it was because they were so used to doing it to themselves that they didn’t know how to do it to another boy or maybe because they weren’t really used to someone else touching them.

I also wondered if they could do it to each other then could Betty or I do it to them?

Watching two boys do it was more than twice the fun of watching one boy do it.

-----Diary End ---

Way to go, Barbara! I wondered if she ever told mom any of this. I don’t mean the details, but I’m wondering if these extreme feminist ideas were passed down to her daughter. I can’t see how it would not be. Mom was always open about sex with me and gave me all the information I need to deal with boys. She never told me that I should dominate boys, but she did tell me that boys were not better than me and that I should stand up for myself.

----- Diary Begin -----

October 14, 1961 (Saturday)

Dear Diary,

I got my wish to handle a boy’s penis – two boys. Betty made the boys get naked again. She ordered them to start masturbating and encouraged me to pay close attention. I didn’t need to be told that!

She said that I had to pay attention because I needed to learn how to do it because once Raymond got hard I would get to “jack him off” as he put it. While I was doing Raymond, she would be doing Alex.

Betty stopped the boys in mid-masturbation. Both their penises were standing out from their bodies and seemed to be pulsing with the beat of their hearts.

“I think they are ready,” she said and then invited me to step forward and take a hold of her brother’s penis.

I’ve been looking at Raymond’s penis for a couple of weeks now, but now I was actually going to touch it. My head was spinning and I felt just a little sick with the excitement.

I took a couple of deep breaths to calm me down and then took a close look at it. It looked the same, but it also looked different. I was noticing things I did not see before.

I noticed the veins on the shaft. I noticed the little bumps on the back of the head and wondered if there were nerve endings in there and how sensitive that would make it. I notice how the head would pulsate just before he made those wet drops. I also noticed, that as hard as it was, it would stiffen up a bit more when he did this. I noticed that it got redder the more I played with it.

I also noticed how much control over the rest of his body I had. Every now and then, he’d give a moan of pleasure and his whole body would flinch. I found that the more I played with him, the closer these seemed to get. I decided to rub faster to make them happen.

And then it happened. His body went stiff and did not relax. He stopped breathing but managed to grunt out, “Keep pumping! Keep pumping!” followed by some hoarse sounds that I could not make out.

But my attention was somewhere else. I could feel his penis get hot and hard in my hand. The head swelled out more than I saw it do before. There was a twitch and this white stuff squirted out like when he did it himself.

I kept pumping like I saw he did when he did it, and his body alternated between stiffening up and going limp keeping pace with the squirts.

The stuff felt so hot on my hands. Eventually he was hardly squirting and begged me to stop.

I did it! I made a boy ejaculate. All by myself. It made me feel so good especially for being a girl. Boys are so weak this way.

-----Diary End ---

HOLY SHIT! Barbara. How I wish I could have been there with her. Just watching would make my panties wet. I’m having a tough time imagining what it would actually be like to touch a penis, much less masturbate one. I’m going to read this again and then take a shower.

----- Diary Begin -----

October 21, 1961 (Saturday)

Dear Diary,

It has been one heck of a week. I got so wound up last Friday that I still haven’t come down. I want so much to let my friends in on this. Every time I see Judy and Carol I just want to blurt it all out. They know I know something and keep asking me what it is. I keep telling them that it’s none of their business and that it isn’t really that big anyway.

So when I went over to Betty’s last night I was already high on seeing boys naked.

What Betty made them do almost had me sick with the excitement.

She made them get naked again and then made them masturbate for a couple of minutes until they got hard.

Then she made Raymond get down on his knees and had Alex stand in front of him with his penis in Raymond’s face.

Then she told Alex to suck on her brother’s penis. I was in shock. He made pee there. That’s so dirty. Alex didn’t want to do it but Betty told him that she would tell his parents what she caught him doing.

Alex took it in his mouth and then spit it out. Betty told him to put it back in and keep sucking it until he made Raymond make sperm.

I tried to stick up for Alex and asked Betty not to force him to do it, but she told me that boys want girls to do this to them all the time. That sort of turned me around. If it’s OK for a girl to do it to a boy then a boy doing it to a boy as punishment should be OK too.

She told Alex that after he got done with Raymond that she would make Raymond do it back to him.

After she made them do each other, she asked them how they liked it. Both boys were not happy with it, but said it was OK especially being on the receiving end. I think Betty didn’t expect that. I think she expected the boys to hate it and by forcing them to do it, turn them away from their queer ways.

All I know is that it was fun watching the boys do it. This was something new but more than that it’s something the boys did not want to do but did it because a girl told them they had to do it.

-----Diary End ---

Oh Barbara, you were witness to probably the most embarrassing thing one boy can do to another: a blow job. I’m getting smart. I put off my shower on Saturday until after I read the diary. I also masturbate when I’m in there recalling the words recorded so long ago. I used to only jill off rarely when I was under great stress. The words in the diary put me under a different kind of great stress.

----- Diary Begin -----

October 28, 1961 (Saturday)

Dear Diary,

I made arrangements with Judy and Carol to go trick or treating on Tuesday. We’re going over to Judy’s house to decide what costumes we are going to wear and make them. We’ll probably be stuck with taking Judy’s little brother with us but he’s OK for a little kid.

I had fun at Betty’s last night. We did something new.

We made the boys get naked for us.

She stood them side by side and then spit on her fingers and put her thumbs on top of Alex’s penis and the next two fingers of each hand under the head and started to massage it. She told me to do the same to Raymond.

I remember how funny I felt the first time I touched a penis. I was so excited, I almost got sick. I think I got over my nervousness. I liked massaging Raymond’s penis. It felt good in my hands and I really liked how it grew and got hard.

I played with him for a couple more minutes before Betty told me to stop. She then told the boys to turn and face each other and then made them step forward until they were so close they almost touched each other.

She reached in and grabbed Alex by his penis just behind the head. I did not have to be told to do the same thing with Raymond.

“We’re going to play a new game,” she said. The way the game was played is that I was to rub the head of Raymond’s penis against the head of Alex’s penis while she did the same thing with Alex rubbing his penis against Raymond’s.

She took up a position to the side and slightly behind Alex and reached around to hold his penis. I did the same with Raymond. Each of us sort of half-hugged our boys.

She told me that we were going to keep rubbing them and that the girl who could make the other girl’s boy ejaculate first would be the winner.

This was such a fun game because we had to use each other’s “boy parts” to play it.

I know that if a girl rubs a boy’s penis enough with her hand, she can make him ejaculate. A boy can do this to himself too. But now the thing doing the rubbing is another penis. It’s using boy parts to make other boy parts shoot semen.

At first, it was kind of clumsy, but after a while we got the hang of it and even started taking turns. First I would swirl my penis around hers and then she would swirl hers around mine.

*Giggle* I just looked at what I wrote. “MY” penis and “HER” penis. It was like they were our toys that we could play with. I have a lot of toys, but this one is my favorite. I don’t like which I like better, making the boys play with them for us girls or playing with them myself. I think I like it better when I get to play with them.

When I think about it, it’s fantastic. Here are two girls, fully-clothed with two naked boys, both of whom are older than me and we are using their penises – the very thing that makes them boys as toys in a game. Every time I think about it, my stomach does flip-flops.

It’s really fun to see their penises and to play with them, but to have girls in charge of boys like this makes me feel doubly proud to be a girl.

Anyway, Betty and I must have played with the boys like this for an hour. It certainly seemed like we were at it forever. One thing I did notice is that we didn’t need to keep spitting on the boys’ penises to keep them slippery. Both of them would leak some stuff as we played with them.

Then I could feel it. It was the same feeling I felt when I jerked the boys off before. First there was the hardening, then the twitching in the penis. I could feel Raymond’s body tense up and he gave out a grunt and then he did it. He squirted his sperm all over Alex’s penis. I could feel his body buckle and I held him up so he didn’t fall. Finally, he stopped squirting and regained control.

Betty won the game.

She made Raymond get down and suck Alex’s penis clean and all the way until Alex made sperm too.

-----Diary End ---

Oh, this is so hot. I don’t even have to touch myself to make my juices flow. I always thought that the 1950’s was so strict and conservative. Now I know that there was probably a lot going on between boys and girls in private.

I could not wait until next Saturday to find out what was happening. About the only significant event recorded otherwise was that while the girls were out trick or treating, Judy’s little brother, Jimmy, had to make pee, so the girls took him into an alleyway where they watched him do it. Judy was unphased, since she’s seen her brother do this countless times and Barbara feigned interest, but compared to Raymond and Alex, Jimmy’s six-year-old dinky was really dinky. Carol didn’t have a brother, so she always enjoyed little boys making pee even though it was a common sight in the neighborhood.

----- Diary Begin -----

November 4, 1961 (Saturday)

Dear Diary,

It was another good night at Betty’s we played the penis swirling game again and had the loser suck off the winner. We must be getting better. It didn’t take as long to make one of them ejaculate. Betty won again but this time she was handling her brother’s penis. I think we are going to have to keep score.

We made the boys jerk off for us at the end of the evening. I don’t know which I like more: when they do it separately so I can pay attention to each one or when they do it together. It’s nice seeing two boys do it at the same time.

-----Diary End ---

The entries that followed had less and less detailed descriptions of what Barbara and Betty did with the boys. It was like having naked boys to play with was a natural part of Barbara’s life.

There was a mention of Betty’s female cousin being there on one of the evenings but other than that, she almost made it all seem routine.

I kept reading Barbara’s diary to the end. It lasted until she turned 12. She managed to fill up the almost the entire book in a year. This is her last entry.

----- Diary Begin -----

August 18, 1962 (Saturday)

Dear Diary,

I can’t believe it. It’s been a whole year! I’m now 12.

It’s been a great year and I am glad I shared it with you. We’ve been through so much together. You were there when I turned 11. You were there when I saw my first naked big boy. You were there when Betty and I played with and learned about big boys. You were there when I got my first training bra.

There will be more to tell, but not for you. You can see for yourself how few blank pages are left in you.

Mom noticed how much I wrote in you and she gave me a new diary: one for the new year of my life.

I wish you could be here for when I get my first period. I can feel it coming on already.

I am really getting interested in boys and some of them are getting interested in me. You won’t be witness to my first kiss.

I’ve recorded all my memories in you. You cannot forget me. I will not forget you. As I close you for the last time, I will put you in a safe place. I will keep you and cherish you.

Someday when I am older, I will come back. I will open you again, not to record history but to remember it. We’ve had such great times together. Someday, I may also have a daughter and I will make sure when she turns 11, she will have a diary just like you. And when she has daughters of her own, I will encourage her to pass the tradition on.

So, Dear Diary and dear friend, the time has come to say goodbye. I will move on and you will not, but do not weep for I will keep you in my heart always.

-----Diary End ---


Maybe Dear Diary did not weep, but I did. I felt like I was losing a friend, too. I had gotten to know Barbara over the past year. She was real to me. As real as any of my other friends. Though her diary, my grandmother came to life again as an 11-year-old girl if only for a year. I miss her now more than when I lost her for the first time. However, this time, with her diary in my safekeeping I can always go back and visit her.












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