Confessions of a Boy Babysitter

[ bg, 1st, xdress, toys ]

philipspencer74@gmail.com

Published: 29-Jul-2013

Word Count:

show Author's Profile

show Story Summary
Disclaimer
This story was originally published in a slightly different form under the pseudonym 'dirtyteacher.' This story is copywritten by the author. This is a work of fiction, and any resemblence to real people or events is pure coincidence.

Chapter 1

"Mark, Mrs. Haley wants to speak to you," shouted my sister, Margie.

I walked to the kitchen where she was holding the phone. "Why does she want to speak to me?" I asked.

"She wanted me to babysit Saturday night for Dalon and Dara, but I can't because I'm going to sit for the Brandts," she explained. "I said maybe you could do it."

"I don't know anything about babysitting," I said.

"It's real easy," she replied. "The kids are real good, and they go to bed early. All you have to do is check them during the commercials, every hour or so. If there's an emergency, you call the parents, but there's never an emergency. And you get paid fifty cents an hour. Anyway, you've looked after Jim and Mary."

Jim and Mary were our younger brother and sister; this was the mid-sixties, so fifty cents an hour for a kid of twelve was a lot of money. My parents did not give me an allowance, so my only source of income was $1.53 per week from a one-afternoon per week paper route. I could easily make twice that in one evening.

I took the phone, and spoke to the woman. She asked me to be at their house at 7:30 p.m. that Saturday. And she told me that she and her husband expected to return about 2 a.m.

Mom made me take a shower after playing baseball all afternoon; I planned to go to the Haley's as soon as the Flintstones were finished. When the chorus finished the last, "Yabba-dabba-doo," I grabbed my copy of "The Hardy Boys at Skeleton Mountain," and rushed next door.

Mr. Haley, a robust, balding man in his early forties, opened the door. "I'm glad you could come, Mark," he said. "I'll show you around. Mrs. Haley will be ready in a few minutes."

While I had never been in their house before, two of my friends' families had the same exact model, so I was familiar with the layout. The door to the master bedroom was slightly ajar as we walked by, and I got a glance at Mrs. Haley's legs as she pulled on her panty hose. Without a word, her husband discretely closed the door and continued the tour.

At last he showed me the telephone and wrote down the number of the house where they were going. He told me they played bridge once a month with some other couples, so he would appreciate it if I left the first Saturday night of every month available. Already I felt as if I were replacing my sister, a thought that did not bother me at all. The man told me there was plenty of pop in the refrigerator, if I wanted any, and that I could help myself to potato chips. Then we went to the living room.

Eight-year-old Dalon and her younger sister Dara were lying on the floor watching television. Both girls were wearing pajamas, and I glimpsed Dalon's white underpants under her shortie PJs. Mr. Haley told them I would be babysitting, that they were to be in bed by 8:30, and that they were to listen to me.

"One other thing, Mark," he said. "Don't let Dara drink any water or pop - especially pop - before she goes to bed. Dalon's okay; she can have a glass if she wants. And make sure that Dara goes to the bathroom before she goes to bed."

I could smell Mrs. Haley's perfume before I saw or heard her enter the room. "Hi, Mark," she said. I turned around looked at her. She was extremely attractive in a red and cream, knee-length dress that made her blonde hair stand out. Not bad, I thought.

Both parents said good-night to their children and gave them a kiss; then they were on their way. The three of us kids watched TV. Dalon and I shared the Coke that was in the refrigerator, but I refused to give any to little Dara. I thought it was cute that both girls gave me a kiss before they dutifully went to bed at 8:30 sharp.

I was not interested in the TV movie, so I read a chapter about the amazing adventures of the boy detectives, Frank and Joe Hardy. Their adventures were not all that amazing, and I soon got bored. Seeing that the girls had left their Barbie dolls lying on the floor, I had an idea.

I grabbed one of the Barbie dolls and, rummaging through the clothes, I found her head. I put the head into place, and then I dressed her in one of the little outfits that was lying about. Next I grabbed the Ken doll, which not only had a head, but was actually dressed. "Ken" knocked on Barbie's door. In a high, feminine voice, I said, "Who is it?"

Using a deeper voice, I imitated the male doll. "It's Ken. May I come in?"

"Oh yes, Ken, let's kiss," I said in the Barbie voice, pushing the heads of the two dolls together.

"I love you, Barbie," declared my Ken. "Let's fuck."

With that, I walked both dolls to the miniature bed and took their clothes off. They tossed and turned for a minute or so before I sighed and got up to change from Carol Burnett to Lucille Ball.

Even to this day, I can take Lucy and Desi only for a short while, so I decided to explore the house. Neither the living room and nor the kitchen had nothing special to offer, so I headed for the master bedroom. I was sure I could find all kinds of treasure in that room; all I had to do was look for it. Being Protestants, they didn't even have a crucifix, let alone a special blessing of their marriage signed by Pope Pius XII like my parents did. I knew I would have to check the dressers.

I opened the top drawer of the chest, and cool! I found a pistol of some kind. Whether it was a .45, .38, or .22 I had no idea, since I had never held one in my hand before. I picked it up - and confident that I could handle it, placed both hands on the handle and pointed it at the mirror. I was a bit frightened that I might have an accident, so I carefully returned the gun to its place and checked out the next drawer.

Men's socks, underwear, and handkerchiefs. The next drawer brought sweaters, shirts, and some boring ties. None of the drawers revealed anything of interest, unless I really wanted to get nosey and read the papers I found in the last one. I decided that would be really wrong, so I decide moved to Mrs. Haley's dresser.

From the beginning this promised to be more promising. There was a box of costume jewelry on top of the dresser, which I opened first. I examined the various bracelets, earrings, and necklaces, and tried to imagine who would wear them. I did the same with the lipstick and mascara that were lying on the dresser. I sprayed a bit of perfume on my wrist as Margie had taught me when we bought Mom's birthday present, but after four sprays, I could not distinguish one from another.

Moving to the top drawer, I found some more make-up, some boring snapshots from Christmas, and a weird, plastic penis. I could not figure that one out, so I opened the next drawer.

This was much more interesting: bras, panties, and nylon panty hose. Sure, I'd seen Mom's and Margie's any number of times, but this was different. Both of them were overweight; Mom was past her prime, and Margie's face was full of ugly pimples besides. Moreover, incest was the furthest thing from my mind.

But Mrs. Haley - Dee Haley - she was something different. She was a real woman, made of flesh and blood, and she had a nice body. Not a great body, as Mrs. Merkel, my beloved third grade teacher, had had, but a nice body. My heart raced as I held a sexy, padded bra to my chest. I had to check all of these out!

I rushed to the closet, and finding Dee's side - I no longer thought of her as the unapproachable "Mrs. Haley,"- I looked through her things. I pulled out a white, silky slip, took it off the hanger, and laid it on the bed. Next I found a light green, sequined dress, which I laid next to the slip. Did I dare try these things on? The thought was perverse, yet I could feel a raging hard-on.

The television was still blaring away in the living room; the children were sound asleep, as Dee and Don were not expected for at least four hours. I slipped off my shoes and slipped my foot into one of the beige pumps I found in the closet. Like Cinderella, this was a perfect fit! I had to try on an entire outfit.

I removed my clothes, and naked, I examined Dee's panties. At last I chose a red pair, and I put them on. They did not fit well over my stiff prick, but I managed to get them into place. I was concerned that Dee might notice the precum stain the next time she wanted to use them, but it was too late to do anything about that.

Next I chose the black padded bra I had so lovingly examined before. It took me a few minutes to get the contraption in place, but I finally figured it out - snap it in front, then slide the thing around; pull up the straps last. I so admired what I saw in the mirror that I decided to check out the make-up. "You're so pretty," I commented to reflection after I painted my lips bright red.

It was time to put on the panty hose. I knew this was a delicate process - I did not want to cause a run, for that might lead to some unpleasant questions. Slowly I pulled the hose over my legs, as I had seen my mother do any number of times--indeed, as I had seen Dee do just a few hours earlier. I did not like the look, and, given my aroused state the panty was too tight, but the silky feel on my legs was wonderful.

"What are you doing in my mom's room?" asked Dalon.

Chapter 2

"What are you doing in my mom's room?" asked Dalon a second time.

"Nothing... why don't you go back to bed," I babbled.

"You're playing dress up, aren't you?" she asked. "Dara and I play that all the time, but I didn't think big boys played. Can I play with you?"

"Um..."

"I'm going to tell," she said.

"No, no! You can play... come in!" I said. "We can play anything you want, and I won't even tell your mom and dad that you stayed up past your bedtime, if you promise not to tell on me."

"Why are Mom's pantyhose sticking out like that?" she asked.

"Do you want to feel it?" I asked hopefully. "Come and sit next to me."

"First, tell me why it's sticking out like that."

"It just is," I said. "It's perfectly normal."

"No it isn't; it's your penis, isn't it?" Dalon asked. "I just know it is, but we went on a field trip to the art museum, and there are paintings with naked men, and their penises don't stick out like that."

"Okay, okay... the truth is that yes, it's my penis," I said. "You see, when a guy sees a pretty girl like you, or pretty underwear like your mom's, his penis gets big and hard. Come here and you can feel it."

"But why does it get hard?" she insisted.

I knew it had something to do with sex, but I was not exactly sure what the mechanics were. It had something to do with being naked in bed, hugging, kissing, caressing, and the like, but I was pretty sure there was something more.

"It just does," I declared impatiently. "Are we going to play or not?"

"Are we going to play dress up or something else?" she asked suspiciously. "I want to see you in Mom's dress!"

"Okay, but you have to dress up too," I countered. "Take off your nightgown."

She pulled her nightgown over her head and stood before me in her underpants. "Find a bra that you like, and I'll help you put it on," I suggested.

"It's too big!" she cried. "And Mom's panties are too big too. Dara and I don't ever try on the underwear, just the dresses and high heels. You said you were going to do that."

"Just forget the panties and put the dress on," I suggested.

Then I pulled the dress on, and Dalon pulled up the zipper. It was tight, and I felt silly, but I put the high heels on that I had tried earlier. Dalon put on a dress that reached to the floor. At Dalon's insistence, we walked all around the house, including Dara's bedroom, before returning to the master bedroom.

"Do you want to play something else?" I asked. "Another secret game?"

"What?" she asked eagerly.

I said, "You have to take all your clothes off."

"Okay, but only if you take yours off too," she agreed.

We took Dee's dresses off, and I carefully folded and put her bra and panties away. It took some extra coaching, but I managed to convince Dalon that she should get completely undressed too. I used to take baths with Margie, and I had seen my little sister, Mary, naked any number of times, but this was new, exciting. We sat on the bed, facing one another; her bald pussy was only inches from my erect member. Dalon placed her hands on my prick, and "Does it hurt when it gets stiff like this?"

"Well, it hurt a little bit when I was wearing your mother's things, but normally it doesn't hurt - it feels good," I said. "I think boys' clothes are made in a special way so that you can get a hard-on and it isn't too tight. But having your hand there - now that feels real good!"

I placed my over hers; together we jerked off until I shot several streams of cum onto her naked crotch. "Oooow, what's that stuff?" she asked.

Mom had explained wet dreams to me, even if there were other gaps in my sex education. "Those are the little seeds that a man gives to a woman so she can have a baby."

"I'm too young to have a baby," she said. "You can't have a baby until you have your periods."

"I know; my sister explained it all to me when she started having her periods," I said. "But we can still play, can't we?" I suggested.

"Yeah, sure," she laughed. "That stuff is kind of sticky. And look, you got it all over Mommy and Daddy's bedspread."

I grabbed her nightgown to wipe the goo off, and I suggested she help me put the remaining clothes away. I no longer felt comfortable in the master bedroom, and I wanted to get out of there as soon as possible. I thought Dalon might object, but instead she said, "Okay, but then I get to play with your penis in my room. How old are you, anyway?"

"Twelve," I said proudly. "I'll be thirteen in October."

"I'm eight," she replied. "My birthday was in May."

We put all Dee's things away and straightened out the bedspread. Dalon grabbed my hand to lead me to her room, and I bundled up my clothes in the other hand. Once in her bedroom, I dropped them in a pile on the floor and looked around.

I had not had much of a chance to look at Dalon's room before. She had a large, pink-canopied bed in the middle of the room. The walls and curtains were also pink. There was a small dresser and vanity along the wall opposite the window, and there was a record player on top of the dresser.

Dalon crept into bed, and I crawled next to her. Turning off the light, we hugged and kissed in the darkness for a while. I kissed the flatness of her breasts, and I tried to imagine how they would feel in a few years when they began to protrude.

She took my hand in hers and placed it between her legs. "You can touch me here," she declared.

With two sisters and a number of younger cousins, I had seen girls' slits before, although I had never actually touched one. It felt nice to feel the soft skin and the warmth inside, although I was taken by surprise when it started to feel moist. "I thought Dara was the one who went pee in bed at night," I said.

"It isn't pee," my young lover informed me. "Keep rubbing me like that."

I was able to stick my finger in Dalon's pussy a bit, but I found a barrier of some sort and did not try to push further. "I think you're supposed to do that with your penis," she giggled.

"Put my penis in your... um... vagina?" I asked.

"Sure," she answered, but did not make any moves toward me. "My mom said that when I'm bigger, I'm going to have a period for a few days every month, and the blood is going to come out my vagina. It's perfectly normal and it has to do with making babies..."

I had some idea of what she was talking about; my older sister Marge and I used to bathe together when we were younger, but we did not anymore, and she had told me that she would check the days off on her calendar to keep track of her periods.

"I figure if a baby comes out of the vagina, that must be the place where the seeds go in," Dalon stated, adding, "I'm too little to have a baby, but we can pretend, can't we?"

This made sense, too. At school, Sister Laurentia had explained about how the bees, and sometimes the birds, landed on top of one flower and brought the pollen to another, but she had never related it to human beings. Things were beginning to click. I pulled Dalon closer and poked at her vagina. "Ouch!" she cried.

"I can't get it in, but let me try again," I said. I thrust a second time. "That hurts!" she complained.

"I know it does honey, but like you said, we have to do it this way," I said, trying again.

Mercifully, on the fourth try, I finally penetrated her hymen. "Ooooow" she screamed. "You're killing me."

"I'm sorry, but they say the first time it always hurts," I said. "Oh, man, this is a really tight fit-let me try again."

I pulled out and thrust again, penetrating a bit deeper, but still causing Dalon pain. "Try not to make so much noise - you'll wake your sister up,"

We lay perfectly still for a minute or so. "I think you're supposed to move," she coaxed.

"Yeah, that sounds like a good idea," I agreed. "I've never done this before."

I pulled back but did not withdraw, and then I thrust one more time. I managed to penetrate deeper, and she moaned loudly. "Does it hurt?" I asked with worry.

"Not so much," she replied. "Do it again."

Once more I thrust, and again I penetrated more deeply. Dalon encouraged me to continue, but as soon as I started to pick up speed, I lost totally lost control and exploded in wave after wave inside her. "Dalon, Dalon, Dalon!" I cried in ectasy.

I put my full weight on the little girl and then rolled to my side. "You don't know how good that feels," I panted.

"Have you finished already?" she asked, admonishing, "Don't pull it out yet."

"I thought you said it hurt."

"Yes, but not so much," she said. "I'm kind of sore, but at the same time it feels good to have you inside. Let's just lie here for a while. It's too bad it didn't last longer."

We embraced tightly, and I decided to see if I could have another go at it. I pulled out, but my prick shriveled up and I was unable to penetrate again. I held Dalon some more, but she said, "I have to pee."

She stood up and walked to the bathroom. I wanted to watch, but something told me to stay where I was. No sooner did I see the light of the bathroom shining in the hall than I heard Dalon let out a shriek of horror. I ran to see what was wrong.

"I'm bleeding!" she cried. "Mark, what am I going to do?"

The girl's vagina was full of blood, and it was dripping down her leg.

"Can we stop it somehow?" I asked. I then added what may be the cruelest thing I've said in my life. "They're going to kill us!"

She grabbed a big wad of toilet paper and started dabbing at her cunt. "I think I stopped bleeding," she said. "I guess I'll be okay." Then she laughed. "You look so funny with your... uh, penis just hanging there!"

"And you look beautiful naked," I commented, and just then my prick began to harden again. "Are you sure you're okay?"

"Yeah, no thanks to you," she said. "What do we do now?"

"I don't know," I said. "I guess you'd better put your pajamas back on and go to sleep, and I'd better get dressed before your parents get home."

"I think I should take a bath," she said. "But you have to run the water. Mom never lets me do it alone."

"Then I get to take a bath with you!" I exclaimed.

The bath was fun, and I was ready to try sex again. "I... I don't... it still kind of hurts," stammered Dalon.

"Oh... okay," I said, disappointed. We wrapped one another in towels and walked back to the bedroom. "Uh, oh," I commented upon seeing the bloodied sheets. "We've got a big problem."

"No problem," Dalon said cheerily. "We can wash them. I help Mom do it all the time, because Dara still wets the bed, remember? First get dressed."

We got dressed, and then we changed the sheets. We put the soiled sheets into the washing machine, and we alternated between watching "I was a Teenage Werewolf" on the TV and making out while they washed. Next we stuck the sheets into the dryer. When they were finished, we folded them, and finally, Dalon went to bed.

Mr. and Mrs. Haley arrived home before the movie ended; they paid me $3.25, and Mr. Haley walked me home.

"Mark, telephone," said my mom three days later. "It's Mrs. Haley. She wants to know if you can baby-sit Saturday night, and she said that Dalon specifically asked for you. What should I tell her?"

END

R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s - R e v i e w s

this guy

A little more description would have been a plus, but overall a well thought-out well written story...

Adam

I read this story and I jizzed in my pants

kyle

I love it. Do you plan to write more like 'confessions'?

The reviewing period for this story has ended.