This story is true ,it happened about 50 years ago.
It takes a while to lead up but it tells what really happened my first
My first time with my baby-sitter
It all started when my parents bought a bar on the far side of town. Every night they
would go to tend the bar and my sister would sit me. There is about 8 years between me
and my sister. She graduated high school and started college. I was 9 turning 10 mom
and dad said the people they were buying the bar from had a daughter and that she could
sit me. I protested saying I was old enough to stay home by my self. But they would not
hear of it. So it went that I had to got to pervious owners home which was right next door
to bar. The first night I was there Cleo and Alma were home but their daughter was
staying at friends that night. It was actually Alma’s daughter and Cleo’s step daughter.
But anyway It wasn’t till the next day that I met Diane, she was about 15 at the time. She
was average looking but had big tits like her mom. She wasn’t ugly but had reddish
shoulder length hair, freckled face, about 5’6” tall and a little heavy set. Not fat just full
bodied. I’d guess her to have weighed 140 -150 lbs. with I’d have to say a D cup tits.
The first time we met she was not happy with me going to screw up her life by being
there every night. Not to mention she had to watch me. She said that it was unfair and that
she didn’t want to do it. her mom said it would do her good to have some responsablity
and she could earn some extra cash. Then I said I did not want to be there either but my
parents did not give me any choice. She just looked at me and said sure spoiled rich kid.
I didn’t understand my parents were not rich by any means, my dad bought the bar with
his life savings from working at a factory 50-60 hrs a week. We were not poor but far
from rich. Diane’s mom and step dad were heavy drinkers and had to give up the bar due
to the fact they drank and gave away more than it earned. It was the only way to keep
from loosing their home. I think Diane knew that was true but did not want to accept it.
I was raised Catholic even went to catholic school. The nuns were very strict and of
course sex was never spoken of. At home or at school, if it was brought up at school it
was said to be a sin unless you were married and then only to bear children. So I was very
ignorant about sex and anything to do with it.
Diane on the other hand was Protestant and had liberal knowledge of sex through other
kids. Her parents were always going at it, they had sex the first night I was there. They
left me in the front room and told to watch TV and they would be back soon. I could hear
them in the bedroom the bed squeaking and her moands. I had heard the same kinds of
noise from my mom & dads bedroom just not so loud. after a little while they came back
into the room , she got him and her a beer and sat and watched tv for a while. Then Cleo
said he was going to the bar and see my dad. Alma wanted to know if I wanted anything I
said no I was OK. We sat there till mom showed up and said it time to go home. I need to
get a bath taken and get ready for school. Alma said I could bathe there but mom Said no
I did not have night clothes with me. She told mom to bring them next time and there
would be no need to take me home till the bar closed. Mom reluctantly said OK , next
tomorrow I’ll bring his Pj’s.
The next evening Diane was home, we sat there watching TV for quite a while. Then she
said mom said to make sue you take a bath. I said it’s still early and I was not ready to
take one. So she said OK I’ll take one first and you can use my water when I’m done. OK
I said, as long as it’s still warm. I’ll make sure it’s not cold and warm it up when I’m
She went into her bed room and then into the bathroom. I could hear the water running
an could hear the sound of her bathing . It was and older house and the bath was just off
the dining room. The living room and dining room were joined by a large archway. I
could heard her getting out then a few minutes later she came out and said your turn. She
was just wrapped in a towel I never really paid attention I just got my Pj’s and went the
bath. I had just climbed into the tub when I heard a knock on bathroom door. Diane said
she had forgotten her underwear. I said I was in the tub could she get another pair from
her room. She Said no they were the matching bottoms for the top of her nightgown. I
said wait till I get through and then get them. She what’s the matter was I afraid she
would see me naked. I said yes it was not right for a girl to see a boy naked. She just
laughed and said who said that. I told her the nuns had said it’s a sin and I could go to hell
for sinning. She laughed again and said as if she ever want to see my skinny naked ass.
That made me mad and I said I’ll get your bottoms and hand them out to you. OK then
she said just hurry up. I got out of the tub and got her bottoms off the clothes hamper.
They were silky and I had never touched anything like them before. The were pink and
even smelled like perfume or something. I smelled them and rubbed them on my cheek,
oh how soft and smelled so good. I took them to the door and opened enough to had them
to her around the edge of the door. She took them and I went back to finish my bath. It
was then I noticed the bath water even smelled kind of the same scent. I finished and got
my PJ’s on.
I went back into the living room and sat down on the end of the couch away from Diane.
I noticed the night gown she wore was all the same material. I couldn’t help but wonder
how it felt to wear such silky things. She noticed me looking at her and said what is it.
Shy as I was I was surpprised when I blurted out how silky her Pj’s were. She just
laughed and said that’s what girls wear. I knew my sister never wore such undies or
nighties. Oh , OK I said but I did not understand why I said it. Then she said girls are
suppose to wear sexy things. Sexy ? I was lost as I did not comprehend the idea of sex as I
had almost no knowledge of it. I must have looked stupid as she said you no clue about
sex do you. I said just what the bible says it is for married couples to bear children. Other
wise it’s a sin and you can go to hell for doing it. With that she almost died laughing.
Boy do you have a lot to learn about life. I just looked at her puzzled. Then I said and
you know so much. I’d say I know a whole lot more about it than you. As far as it being
bad if it’s bad and can go to hell for doing it , I’ll go to hell a 100 times over. You’ll
understand someday little boy.
Over the next month or so she had her boyfriends come over after her mom left for the
bar. Most ever night they were there till it closed. When her boyfriends showed up she
would tell me to watch TV, then she and he would go out back and get in back seat of his
car. I would ocassionaly look out the rear window to see if I could see her. I could
sometimes see them kissing and then disappear into the back seat. I could se the car move
with a rocking rhythm. Shortly there after she and he would get out and he would walk
her to the house. The whole time kissing, I could not help but wonder what they were
doing while in the back of the car. Then kissing to me was not something I really did
either. I kissed my mom goodnight and my sister and cousins goodbye. But watching her
do it was different. I watched as they walked and stopped to kiss, I could see his hand on
her ass and she had her hands on his . I could tell she liked it and seemed to push her
upper body into his. When she came e into the house I would be in the front room acting
like I was watching TV the whole time. I like to watch her afterwards because she
seemed to be different. She would look at me and say things, like you do like girls don’t
you. I’d say how do you mean? I mean you like to look at girls , not boys. I said yes I like
girls and have girl friends. But I also have boy friends. She just looked at me and laughed
, you so nieve. I looked at her puzzled. She says oh you would kiss you boy friends like
you would kiss a girl. NO I said I don’t kiss either one. What you have never kissed a
girl? Sure I said , my mom ,sister & cousins. Again she almost laughed so hard she cried.
I looked at her angry and said so what I’m only 9. She said when I was 9, I was kissing a
lot of boys. My dad taught me when I was 7 how to kiss a boy right. He also taught me
how to take care of a mans needs. Your dad must have been a very bad man I said. She
said hell no he loved me and mom , that how he showed me he loved me. Ever since I
was little. Mom and I were devastated when he died in Vietnam. Till mom met Cleo and
he made things for mom better, but he never treated me like dad nor did want him to. He
has tried a couple of times to kiss me but I refused to let him touch me. He’s nothing like
my real dad and only cares about him self. I have real boy friends who kiss and take care
of my needs now. I didn’t know anything about a girls needs or wants. I said what kind of
needs? You know sexual needs. No I don’t know I said. She just says stupid boy and tells
me to go get ready for a bath. I went and got my PJ’s and started my bath. The whole time
wondering what she was talking about sexual needs. I ‘m going to take my bath now I
yelled , OK let me know when you done I’ll check and make sure you got your neck ears
clean. I no more then got into the tub and she was knocking on the door. I have to go. I
said I just got in can’t you wait. No hearing to water run made have to go. Unlock the
door and let me in I won’t look. Why would I want to see you skinny ass naked. I got up
and unlocked the door and got back into the tub. OK I said you can come in. She came in
and says close your eyes while I go. I pretended to cover my eyes and peeked between my
fingers enough to see her pull her skirt up and her panties down. Her panties were blue ,
the stool was right beside the tub. I could hear her peeing . When she was done and stood
up I got glimpse of her ass and almost her pussy. I felt a tingle in my cock and it started
to get hard. I was about 4-5” at the time. She said you missed washing your neck. I said I
just got started I didn’t have time to wash anything. She reached out took the wash cloth
and said give me the soap. If you can’t do it right I guess I’ll have to. I Gave her the soap
after some protesting. She said lean forward and started to wash my neck and back. She
took the shampoo and a glass and poured water over my head and started soaping my
hair. II had soap in my eyes and could not open them . She hit cock with the glass and her
hand while rinsing my hair. I tried not to move afraid of what she might do if I reacted
from her brush with my dick. When she finished rinsing my hair, she started washing my
ears and face. Then my chest coming within inches of my dick. Then she told me to stand
up. No I said ,knowing my dick was hard as a rock. She said get up or I’ll make you.
Slowly I stood up and my cock emerged from the water. She kind of smirked started to
wash my back side and ass. I think all the time looking at my dick. then she washed my
legs and worked her way back up to my groin. Almost the instant she touched my balls
and cock. I shot a small load of cum into the tub. She giggled and said it was loaded. She
continued to wash my cock and balls it seemed like for ever and then she was done. Then
it seemed like it lasted on 2 seconds. She hands me the towel and says get dressed and
left. I was both freaked out by what just happened and turned on. I was afraid if my dad
found out he would punish me , I was sure I ‘d get the belt or worse. I tried to act normal
when I returned to the front room. Diane said she was going to take a bath and get ready
for bed. When I heard the water running I snuck into her bed room and found her drawer
with panties in it. I checked out all the colors and different one she had. Without warning
she appeared in the door way. She saw me in her drawer and said like girls panties. I
didn’t know what to say I just froze. She came over and pulled out a couple of pair and
said take you bottoms off. I was so scared I did as she demanded. She held out 2 pair
and said pick a pair and put them on. What I blurted out. You heard me in a mad voice. I
pulled down my Pj’s and stepped out of them. Pick a pair she demanded again. I took the
red pair she held out in her right hand. Put em on I said. I did as she commanded. My but
doesn’t she look cute she said. Now wear them the rest of the night she demanded . I
went to the front room and tried to cover up. She then came out of the bath room with her
night clothes in hand and just a towel around her. Turn around and watch out the window
she said. I did a s I was told. But I realized the front picture window was like a big mirror
and I could see her as she removed the towel and bared her self to me in the reflection. I
was mesmerized by her tits and the hairy bush between her legs. I watched as she slowly
put on the top and then slid the bottoms up her legs. It was the first time I ever saw a real
girl in the nude even if it was in a reflection. I could feel my self getting hard again. Oh
no, I though how am I going to hide it. OK you can turn around now she said, I kind of
jumped and landed sitting and my hands at my crotch trying to cover up my obvious
erection. She must have seen it because she kind of grinned and sat next to me. It
became clear to me she was liking this too, because her nipples were pushing out
through the thin material showing like never before. She looked at me and said so how’s
my little girl doing. Then she pulled my hand from my crotch and smiled . You like to
wear my undies don’t you? But their kind of big for you huh. Pulling the top band and
letting my cock slip out. Oh looks like its primed ready for another load. Let see she said
and touched the head with her finger. It jerked and I kind of groaned ,Humm you liked
that! I just looked at her wanting to say touch it again. Then she wrapped her hand around
it and started stroking up and down. Immediately shot a small load almost a foot in the
air and landed on her bare leg. She laughed again and that things dangerous you never
know when it will go off. Then I could not believe what she did next she took her hand
from my dick and with her fingers wiped up the cum. Then she licked her fingers clean. I
was shocked and mesmerized again. Mummm good stuff she said . Got any more in you?
I didn’t know what to say but I was still hard. Hold still she said. Then she slid over and
leaned her head down to my lap and took the head into her mouth. She began to suck the
head with in seconds I cum again. My she said, as she pulled her mouth off my cock that
was fast. Licking her lips. I was in heaven and knew I was going to hell ,but I didn’t care.
If this was sex I wanted all I could get. Then she said your turn I just looked at her in
daze and said huh. With that she pulled her top off reveling her D tits , the nipples stuck
out a good 1/2”. Would you like to touch them she said. I in Daze shook my head yes.
Then she took one of my hands and placed it on her breast and massaged it with her own .
Take the nipple between you fingers and squeeze it. I did but to hard she cried out not so
hard. I tried to be gentle and do as she told me , she moaned with delight when I did it
right. Mummm that’s it just like that. After a couple of minutes she said suck on it.
Moved to allow my lips to engulf her nipple and she moaned again. A suck little harder
and lightly bite down on the nipple. As I did she kind of shivered and led out a small cry.
I let go but she pulled my head back to her breast. I continued to suck and nibble for what
seemed a long time. Then I felt her hand on my cock again. I almost immediately came to
full erection. She pulled my head from her tit and stood up and removed her bottoms .
She laid back onto the couch and said come here and lay on top of me. I immediately did
as she requested. I felt her reach between us and aim dick at her awaiting cunt. I did not
know this then but as soon as the tip of my cock touched her hole I came again. She
raised up to push my cock into her waiting hole. As I felt her hot cunt swallow me up and
she began to fuck me from the bottom . She said fuck me I started to move with her and
she kept raising her ass to meet my groin. My small balls and dick worked for what
seemed an hour. Then I shot another load into her and she shivered again and went limp.
She looked down at me and said think you’ll go to hell for that. I said Oh God I hope so.
She then told me I could remove her panties as now I was a man. I said but I like the feel
of the material on my skin. She laughed and said ok keep them , but don’t let you mom or
dad find them. I then put my PJ on over them and wore them home.
After that I could not wait to go to her house.
To be continued