The Bet
I remember when I was 14 and my sister was 17 and we lived
with our folks in one of the southern states. My sister
was extremely smart but I had made up my mind to beat her
in grades. One night I came into my sisters room. She was
sitting at her deske dressed in pajamas, yeah even the
pants too.
“Whats up?” She asked
“Well, we have exams coming and report cards will be coming
out.” I proudly said.
“So? You afraid?”
“Nope. Just thought I would say that my card will be
better than yours.”
“Oh? Is that so?” She laughed.
“Bet mine is better.” I challenged.
“I heard you little brother but mine, of course, will be
better.”
“Bet me.” I said
“What do YOU have to bet with silly?”
“Well, I’ll tell you what. If mine is better, you be my
slave and bring me cokes and do all my chores.”
“And if I win?”
“I’ll be your slave to do whatever you want.” I nodded my
head in satisfaction. Jan, My sister turned and thought
about this proposal.
“You have a deal.” She said, then went back to her
studies.With that confirmation I left and went back to my
room as I knew that I was getting all “A’s” this time
because i had spoken with the counselor already. Victory
was in hand as I laid back on the bed dreaming what a good
slave she would be. The whole family was bound to their
word and she had to do it as it was family honor. Heh heh.
Time came and went. Cards came out. All A’s except one
and that was an A- but no big deal she could beat that. I
ran home and greeted Mom and showed her my card and told
her of the bet too.
“A slave? She has to do everything you say?”
“Thats right.” I folded my arms across my chest proudly.
“Well you father and I are leaving for the weekend but I
sure would like to see this!” Mom said just as Jan walked
in and gave mom her card. I stood there grinning ear to
ear.
“Get me a coke.” I demanded Jan. She didn’t move. Mother
looked at me and shook her head.
“Hey I won and we done a bet!” I stammered. Mom gave me
the card.
“Not so fast young man.”
“What?” I looked at Jans card. All friggin A’s. My face
dropped. Damn.
“And what would you like your brother to do?” Asked mom
looking at Jan.
“Oh nothing right now, but I’ll think of something.” Jan
winked at me and left the room. I had to brace myself.
Beaten by a stupid minus sign. Crap.
Friday evening came and both of us were informed that our
folks were leaving and wouldn’t be back until Sunday night.
Apparently Dad heard of the bet. He told me I had to do
everything that Jan asked me to do and if I didn’t Jan was
to tell him and I would get my butt warmed but good. I
promised I would be her slave for the weekend. With that
note, Mom kissed us both, went out to the car and left.
Damn, here I was. Beaten and had to serve my sister.
“Ok, what can I do for you?” I sheepidly asked. She
grinned and was about to say something, then seemed to
change her mine.
“Come with me little brother.” She said as she led me to
her room. She sat on the chair as I was standing. “Take
off your clothes.” She demanded.
“Uh uh I ain’t gonna do that.” I protested. Hell I didn’t
want my sister to see me…naked.
“Oh you WILL do that or I’ll tell Dad you didn’t come
through with your end of the bet.” She scolded.
“But I’ll be naked.” I whispered. But i knew if Dad found
out that I didn’t do what Jan said I would get a good one
on the butt with the belt when he got home. I unbuttoned
my shirt, kicked off my shoes, took off my socks and let my
levis drop. Here I was standing in my jockys.
“Those too.” Jan pointed.
My face turned very red and I slid my underwear down and
off. Darn jan just sat there looking at her naked brother.
She got up and went to the chest of drawers and brought out
a pair of pale blue panties.
“Put these on.” She demanded. This was crazy but hell no
one was gonna see and I had to cover myself so I put them
on. I felt stupid. Jan went to her closet and brought
back and training bra. She helped me get into this nutty
harness. My hair was naturally long and here I was
standing before her in a bra and panties. She went to her
closet again and brought out a frilly blouse which i put
on, then she brought out a small mini skirt which I also
put on. The hose, yeah panty hose. She even had some
flats for me to put on. Then she led me to the mirror and,
Oh Gawd, she was putting lipstick on me and other sorts of
makeup. I just closed my eyes wanting this to end.
“Ok, Danny, look at yourself.” She commanded. I stood at
the full length mirror. Shit I was a girl! I had to look
twice. Was that really me in the mirror???
“Can I take this stuff off now?” I pleaded.
“No way Jose, we are going out tonight and you are going to
play the role and do as i say, is that clear?”
“C’mon Jan. I can’t go out like…like this.”
“You will go out and you will do as i say or Dad might find
out that…you understand?”
“Please?” I pleaded, but it didn’t do any good. Maybe I
wouldn’t be recognized because it was dark anyway. I
crossed my fingers.
We walked to the park where Jan saw some of her friends and
called them over. Damn this was embarrassing. She
introduced me as her cousin from St Louis, Amanda. We
greeted each other and i was playing the role. Then some
guys came over and I was introduced to them. They were all
Juniors in High School.
“Hey Guys, Amanda said she’d like to suck your cocks.” I
sunk. One of the guys came over.
“Amanda, you wanna suck me off huh?” I looked over to Jan
pleading with my eyes and she just waved a finger at me. I
nodded my head at the big guy. He unzipped his levis and
brought a dick out that was…I know 7 inches long. He
stroked it a couple times. “Well, what are you waiting
for?” He asked me. Again I looked at Jan for hope. There
wasn’t none and all the guys and the girls watched. I got
down on my knees and the guy came close and put his hard
dick against my lips. I hesitated but finally opened my
mouth with closed eyes. The dick went in my mouth. “Well?
Suck it.” He commanded. Damn, right in front of everyone.
I sucked. Then he grabbed the back of my head and started
fucking my mouth while the others ohhhh’d. Soon he shot
his cum and I was swollowing out of impulse. Finally he
pulled out. “Damn, she sucks a means dick.” He said, then
he turned to the other guys, “Who’s next?”
I sucked off 4 guys and drank what they offered me. The
last guy spoke up.
“The hell with getting a blow job, I want some pussy!” He
demanded. Shit what do I do now? Jan spoke up.
“Well, shes still a virgin, but I tell you what, you can do
her in the butt and she wouldn’t mind a bit, would you
Amanda?” Jan asked me with a smirk.
“No I would mind at all.” I stammered. Jan pulled up my
skirt and peeled down my hose and panties and had me bend
over. She took the guys dick and guided it to my butt.
Thank God he was only about 5 inches. Instead of easing it
it–he hammered me while the others clapped their hands.
He fucked for a few minutes and then grunted as I knew he
was cumming. Then he just pulled out with a plop.
“Nice tight ass there Amanda.” He said with a smile.
“Thank you.” I said as Jan pulled up my panties and hose.
Damn my butt was sore.
We walked back home and went up to Jans room.
“I will say that you did everything I asked. Now strip
outta of those clothes.”
I hurried and threw the clothes off and stood there.
“Danny you been so good. Thank you, now its your turn.”
I didn’t know what she meant until she fell to her knees
and put my dick in her mouth all 3 inches of it and started
to suck. Man I was in heaven. I shuttered and was
experiancing my very first orgasm. Jan drank all i had to
give her, then she stood up.
“Would you like to do this again tomorrow night? This
isn’t a command.”
“Yes.” I said without a thought.
“Good. We’ll get you dressed up again and go back to the
park and maybe the guys will be there and maybe they will
have their friends. When we come back, I’ll let you fuck
me.” Fucking my own sister? You bet I would. i couldn’t
wait until tomorrow night!!! I woke early and damn my butt
was sore. I hobbled to the bathroom and then went back to
my room. Jan must have heard me and in a few minutes she
came in.
“Whats wrong?” She asked concerned.
“MY butt hole hurts.” I meekly said.
“Lets have a look.” She commanded
“It’ll be ok.” I said shyly.
“This is Saturday and this is still slave day, now strip.”
Jan said as I stood up and got out of my pajamas. I stood
before her naked. She had me lie down on the bed on my
belly and spread my legs. I felt something cool across my
butt. That was nice! Then I felt her finger at my hole
and she smeared this cool liquid all over, then she
inserted a finger and finger fucked me for awhile. That
sure felt good. She had me rest all day saying we were
STILL going to the park tonight and I didn’t protest as if
Dad heard about me saying no I would surely get a belt
across my butt and it was bad enough now!
I don’t know how long I slept but Jan woke me and it was
getting dark outside and ordered me up and get dressed as
she pointed to the same clothes I had on last night. I
didn’t want to agrue so I just got up and got dressed in
these girls clothes. In a few minutes, Jan had painted my
face and I looked like a little tramp.
“We can find some guys and you can do your thing, and if
you do what they want, I might have a surprise for you
later.” Jan said. Oh boy I get to fuck my sister I
thought.
By the time we got to the park it was dark. There were a
few people there and finally Jan saw her girl friend Becky
and waved her over. Becky was here last night. We smiled
at each other and the two girls started to talk saying I
had to have a dick in my mouth or my butt. They both
giggled and Becky said she would like to see this again.
Becky was a fox. Whereever she went, she had a crowd of
guys with her always trying to get her affections. Tonight
was not any different. First guy was Tony. After I was
introduced and we talked awhile Jan spoke.
“Hey Tony, you wanna blow job?” Jan asked. Tony came to
Jan and she just pushed him away, “Not me, Amanda here.”
She said with her hands on my shoulders.
“You know how to suck a dick little girl?” Tony asked.
“y..y..yes” I replied. He stood there for a minute and
then asked jan if it was for real and Jan just giggled and
said it was. The two girls stood on either side of Tony as
I got on my my knees and unzipped his pants. GAWD! His
dick was very thick and long! I bet he supported 11 inches
and i bet it was 4 inches wide!!! The girls groaned in
approval. I licked the whole shaft then took it in my
mouth, but I could only take his head and an inch more and
I started to suck. The smell was really bad this time like
he hadn’t had a bath for a month!! Damn he stunk. My
sucking went faster and faster. He finally shook and
started to cum in my mouth. Even the taste of his cum was
bitter but I swollowed every drop. He withdrew from his
pants came out from the edge of the bushes and called his
friend over who was blacker than the blackest night. Yep I
sucked HIM off too. There wasn’t anymore guys around so
Jan invited Becky to come back to the house with us and she
agreed saying she was about to go home anyway.
We got home and went into Jans room. Jan spoke first.
“Amanda, you want to eat my pussy?” She said as I got up
from the floor. Becky eyes grew large. Jan took off her
skirt and panties. “Hop to it.: Jan said as I crawled
between her legs and started licking her. “Becky when
Amandas done she can do you if you want.”
“Sure.” Said Becky and I was licking like a mad man
savoring the taste of my sisters pussy. I used my fingers
in her hole and massaged her clit and finally she had an
orgasm so powerful that her legs held my head in a hard
grip, but soon she relaxed. Jan motioned Becky over where
we were. Becky got her levis and panties off and laid
down. It took me a millie second and I was licking her
pussy like there was no tomorrow. Becky just laid there
and groaned. And with each groan I licked harder. Finally
she came but not as powerful as Jan.
“Amanda, stand right there.” Pointing to a place near the
bed. Both girls sat naked from the waist down on the edge
of the bed. “Ok, take off your clothes.” Commanded Jan.
I stripped. Beckys eyes grew huge as she was finding out
that I wasn’t a guy but a guy! Her eyes were fixed on my
hard dick, not very big but forbidding. I stood there
naked before both girls.
“How did you get him to do that?” Becky said as the last
of my make up coming off and she recognized who I was. Jan
told her of the bet and Becky started to laugh.
“You can fuck him if ya want too.” Said Jan
“I’ve never done it with anyone yet.” Becky said.
“Oh don’t worry, you’ll love it.” Jan said as she helped
Becky lay down and spread her legs. “C’mere <Amanda>” She
commanded. I was guided between Beckys legs and Jan guided
my dick to Beckys wet pussy. I didn’t wait for the green
flag and just rammed Becky with all I had and she yelped as
I stole her cherry. I fucked her like crazy and told Jan I
was going to cum so she made me get out of Becky and Jack
off while both girls watched. Both girls said “wow” as I
spurt my cum all over the place.
“Ok go to your room and get dressed.” Jan laughed. I left
the room hearing both girls laugh up a storm and giggled.
Later after Becky left and went home, I asked Jan how come
i couldn’t fuck her and guess what? She told me she was
saving herself for marriage!!
The next day the folks came home and mom asked if I was a
good little “slave” and Jan said yes, that I had done
everything she asked. Mom kissed me on the forehead and
dad thanked me for keeping my word. I smiled back at Jan.
I just wonder if we could bet again and I wonder if I could
lose on purpose??”