Babysitting (c) 1997 Master Chris
Story #80 in the Master Chris Collection
It started when I was about 9 or 10 years old. We moved, you see, and all
of a sudden, life changed. Dad wasn't around anymore and Mom and I lived in
a completely new town. I would see may father not at all for almost 20
years before he got hold of his life and tracked me down. In the meantime,
it was Mom and me.
I suppose it all started with the first time Mom had to find a babysitter
for me. Julie was her name and she was almost 5 years my senior. Julie
lived just a few doors down and when she came in to our new home for the
first time I thought she was the prettiest girl I'd ever seen. It was puppy
love I suppose, a young boy infatuated with an older woman.
Julie became my regular babysitter almost immediately. In fact, she would
mind me until I was in my late teens.
The first few times Julie baby-sat were completely uneventful. She was lots
of fun to be around and very attentive. I was a little nervous the first
time she gave me a bath and got me dressed for bed but after the first time,
I didn't give it much thought. It was perhaps the third or fourth time
Julie baby-sat that things changed.
I guess I'd been a real handful that day. When Julie came over, I'd already
been across Mom's knee once. Mom was a believer in corporate discipline and
it was rare that I would go a week without my bare bottom upended over her
knee. Spankings from Mom were pretty straightforward in those days. She'd
get to the breaking point then, before I quite knew what was happening, I'd
be over her lap and my pants would be around my knees and she'd warm my bum
with her hand until I cried and settled down.
That day, when Mom left, she said to Julie, "Keep an eye on him tonight
Julie. He's been naughty all day. And if he doesn't mind you, don't
hesitate to swat his bum." I jumped at hearing this. No one but Mom had
ever spanked me and I sure didn't want Julie to be the first.
I tried to be good, I'm sure I did but it was only perhaps an hour before I
got into trouble. Julie was insisting that I go upstairs and get ready for
a bath and I was refusing. She tried to grab me but I scampered out of the
way. A couple of games of this and finally, Julie had had enough.
Her face changed and she stopped and stared at me. "Bobby", she said, "This
is your last chance. Get up those stairs now or I'm going to give you a
spanking."
I stuck my tongue out at her and tried to run by again. This time, her arm
shot out and grabbed me. "You asked for it." She said.
Unlike Mom who would have just spanked me instantly, Julie took firm hold of
my arm and led me upstairs to the master bedroom. "Bobby, you've got this
spanking coming. If you don't do as I say it'll get worse."
She sounded so serious I didn't dare move as she reached out and pulled down
my sweatpants. A moment later my underpants were down too and I was showing
everything.
"Step out of them." She said and I did. Now Julie grabbed the bottom of my
t-shirt and pulled it over my head leaving me bare naked.
"You're going to get this spanking in two parts." She said. "Over my lap
now for the first part."
She gently pulled me over her lap. Julie was wearing shorts and a t-shirt
that day. I remember it like it was yesterday. As I was pulled over her
lap, my small cock lay against her warm legs and then dropped between them.
It was a remarkable sensation.
With a firm hand at the small of my back to hold me in place, Julie lay a
quick peppering of spanks on my bottom, heating it up instantly much like
Mom. In a couple of minutes I was sniffling and finally, my body stopped
resisting and I lay limp over her lap.
The spanking stopped and for a moment, I felt Julie's hand rubbing gently
around my bottom and up the backs of my thighs. It was as though she was
thinking about what to do next.
"Up you get", she said.
I stood up and my hands dropped naturally to cover my genitals.
"Oh no Bobby. You don't cover up in front of me. You'll start to do as I
say from now on. Put those hands on your head."
I blushed as I followed her instructions. Julie looked me carefully up and
down, her eyes settling on my tiny hairless cock which had decided on its
own to come to attention.
Julie stood up and took me again by the arm. She led me over to a
coffee-sized table in the room and made me get up on it.
"You'll stay here until I tell you to get down" she said. Julie made me
spread my legs and continue to hold my hands clasped behind my head. It was
embarrassing, like being on display in a shop but I did as I was told.
After all, there was still another part of the punishment to go.
Julie left the room, admonishing me not to move if I knew what was good for
me.
She returned a few minutes later. "Down off there young man", she said. In
another moment, I was back over her lap.
"I wonder at your naughtiness today Bobby. Are you feeling ill? I shook my
head, not knowing what to say. Julie was fiddling with something she had
brought into the room with her.
"I think we'll double check", she said. A moment later I felt her fingers
pulling my buttocks open then wide apart. She held them like that for a
moment, just taking in the view of my juvenile anus. Then I felt the cold
glass of a thermometer tickling the center of my crinkled hole. It had
been covered in Vaseline and the cold gooey feeling made me squirm. "Uh
uh!" I said. A quick smack to one buttock made me think twice about
complaining. The glass thermometer slid in easily but Julie never let it
sit still. With the fingers of one hand keeping my buttocks parted, the
other hand was free to tease the thermometer in and out, twirl and twist it
and generally keep my attention for several minutes.
When she finally pulled it out I thought we were done. Not so. Now I felt
the warm tip of her finger at my rear opening. It teased in a tiny bit,
opening the entrance to my rectum then slid in and in and in. It felt like
it was all the way up to my belly button. Julie teased and twisted the
finger in me, making me squirm helplessly. The finger left to be replaced
by something cold again. Something cold and unyielding was pressed through
my crinkled muscle and held there for a moment.
"You need a reminder to be good", said Julie and slid the object in slowly
but even deeper than her finger had gone. It was a carrot I would figure
out later. When it was firmly rooted deep in my bottom, she stood me up.
"Back on the table, young man", she said.
This time I was made to stand facing away from the entrance with my legs
wide apart and my hands behind my head. I could feel the cold object deep
in my bowels and part of it sticking out of my bum and between my cheeks. I
felt ridiculous which I think it what Julie wanted.
Julie walked all around me slapping the back of a hairbrush against one
palm. "Well you don't look so clever now do you?' she asked. At one point,
I could feel her looking at me from behind. As I went to turn around to
look at her she barked, 'Eyes front young man" I was quick to obey.
Suddenly I felt a tapping sensation deep in my bowels. Julie was gently
smacking the end of the carrot was the flat end of the brush. I had never
felt anything like this in my life. Each tiny smack of the brush against
the object was translated to an effect all the way inside my body. The
tapping had another effect also. Each tap it seemed caused my tiny cock to
bob uncontrollably in front of me. I didn't know what to do.
Julie tapped for a while then continued walking around me. When she saw my
hard little cock, she smiled. Reaching over with the cool flat part of the
brush, she stroked the bottom of it from bottom towards the tip. "This is
designed to please women Bobby. You should always remember that when you
get older."
Julie had me get down on my hands and knees. She told me to fold my hands
and rest my head on them leaving my bottom way up in the air with the silly
carrot still sticking from it. "Don't move" she said and finished the
second part of my punishment with a quick hairbrush spanking. Each few
smacks, she'd give a light tap to the cold vegetable buried deep into me.
The punishment was over and, after pulling the carrot slowly from me, she
made me wait while she cleaned herself up. Only then could I get up from
this most exposing of positions to come to the bathroom to get cleaned up
and ready for bed.
I went to bed quietly. When I got up in the morning, Mom mentioned the
incident at breakfast. "I understand Julie had to put you over her knee
last night Bobby" she said.
I nodded glumly into my cereal. This probably meant another spanking from
Mom.
"I'd give you another spanking but Julie told me she gave you a good solid
punishment last night so I'm going to let it go." She told me. "You should
know though, that I've told Julie to feel free to punish you whenever she
sees fit in the future.
My eyes widened a little wondering if Mom knew everything that had happened
but I certainly didn't have the nerve to bring it up.
I'm sure my submissive tendencies started that day. Certainly each time
Julie came over, there would be some opportunity for her to punish me. If I
had been good, it might be a light spank or two along with the humiliating
table display which seemed to be part of the routine virtually every time
she babysat.
I had already started developing by the age of 10 but the punishments didn't
seem to stop as I got older. It was when I was around 14 and Julie was 19
that my Mom was, without a doubt, apprised of exactly how I was punished.
Julie had me on the table, as usual with my head down, my tail up and my
knees spread wide leaving everything completely exposed. We had long since
graduated from kitchen vegetables for objects destined for my bum. Julie
had a tiny rubber object she called a 'plug' which was narrow at the end,
then got much thicker then got narrow again before flaring out to a 'T'
shape. This plug was buried deep in my rectum, the narrow neck holding my
anus wide apart despite the involuntary reactions of my sphincter to expel
it or close.
My bottom was red I was sure because Julie had just given me a hairbrush
spanking. I couldn't see my bottom, of course. Not just because it was
behind me but also because Julie now often made me wear a blindfold during
my punishment. It took away from my sense of sight but, strangely, my sense
of touch and my sense of hearing were all that more acute.
Julie was behind me, not spanking at the moment, she was lecturing. She had
a particular way of doing that. She'd turn the brush over, and gently drag
the bristles along my just spanked bottom or anywhere else she pleased. At
the moment, the sharp bristles were being gently dragged across my well
exposed balls. She'd pull the brush up slowly between my legs with the
bristle side up then when it was clear, she'd give a little tap on the end
of the plug with the flat side. Needless to say, the exercise had my
complete and undivided attention. With each stroke she'd say something like
"And will I catch you doing that again?" or, "will you be good from now
own?"
It must have had Julie's undivided attention too because suddenly we both
started when we heard Mom at the doorway clearing her throat. "I see
Bobby's been naughty", she said. I started to get up but immediately felt
Mom's hand on my back. "No, don't you move just yet young man".
I was mortified. It was one thing for Julie to see me like this with a plug
in my bottom and my cock rock hard hanging from between my spread legs but
Mom had never seen me like this.
"You can just stay there for a few minutes Bobby", Mom said. Julie and I
are going to go discuss some things.
I was left in the embarrassing position for what seemed ages. It was
perhaps 15 minutes or so. I could just hear Mom and Julie murmuring in the
kitchen. Every once in awhile I heard Mom giggle which made me more
embarrassed. When I next heard footsteps into the bedroom I didn't know
what to think. The bristles of the hair brush made one long pass down my
right buttock then up between my legs again before giving a sharp tap on the
plug in my bottom. The plug moved again as it was pulled slowly and
teasingly, with lots of twisting from my body.
"Ok Bobby, get up" It was Mom!
I shot up and pulled the blindfold from my eyes with one hand while my other
hand made a vain attempt to cover my nakedness.
"Hands behind your head" barked my Mom.
I didn't even think. The next instant, my hands were locked behind my head.
"Hmmm, she's right", said Mom. "You are submissively inclined. "Ok, Bobby,
it's off to bed with you. I think it's safe to say however, that things are
going to change a little around here.
Mom wasn't kidding. A few days later Julie came over again. This time Mom
didn't leave. That didn't stop Julie from putting me through my paces
though. Mom observed while Julie stripped me naked and put me into a number
of the numerous submissive poses she had taught me. I was hard the whole
time.
Mom would reach over sometimes to see how hot my bottom was after a paddling
or to jiggle a plug that was in my bottom. She watched with rapt attention
as Julie gave my cock and balls a brush-stroking, leaving me panting and
excited.
Finally Julie looked up. My bottom was hot, I was in the position Julie
liked best for me, on the table on all fours with my head down and tail up.
My tail was hot and red and my bottom was full with the plug Julie had put
there several times.
Finally Mom seemed to take charge. "Up on your knees Bobby, facing us." I
turned around and sat back on my heels. "No, I mean up, she said, tapping
my bottom with her brush to emphasize her point. My bottom was hot enough
that the small tap got me up with my thighs vertical.
"Hands behind your head."
Julie, I noticed was watching closely but the eyes of both women seemed to
be drawn down towards my treacherous cock. It hadn't gone soft in the
entire time I'd been "punished" by Julie.
Mom pulled up a chair and sat down on my left and motioned to Julie to do
the same on my right. With me kneeling on the table, this brought my cock
to eye level. I couldn't help it. It seemed to be ticking up and down to
the pace of my racing heartbeat. Mom reached over with the brush to tap it
lightly making me gasp.
"So Bobby, this sort of treatment excites you?"
I didn't know what to say.
Mom took the edge of the brush and stroked slowly along the bottom of my
cock. It made me tremble all over.
"Do you play with this often Bobby?"
I'm sure my face turned as red as my behind. How could Mom possibly know
about that? Julie's eyebrows raised.
Mom turned to Julie. "If you're going to get him this excited, then you'll
get much better control over him by letting him get his final release. You
can do it yourself with your hand of course, but in the state he's in,
probably just the least teasing with a gentle touch right on the head of the
penis will have him perform for you. Of course, you can always use the
method I'm about to here", she said with a small smile on her face.
Both Julie and I had wide eyes wondering what would come next.
"Alright Bobby, if you're this excited, I'm sure it won't take you long,
make it squirt for us."
"Pardon?", I squeaked.
Mom's voice got firm. I knew that voice. "Do it Bobby. Now."
Slowly, I reached down with my right hand to hold my cock.
"Well?", said Mom.
I started to pull it, first slowly then hard. It only took a few seconds. I
was so close to the edge already that I was pretty much ready.
After that I was left to clean up and get dressed. It was the first session
where two women observed my performance, but by no means the last.
Within a few weeks, Julie sprung yet another surprise on me. I had been
over her knee as usual and was waiting with my blindfold, kneeling upright.
"Open your mouth', she said. I was confused for a moment but did as I was
told.
"Now stick out your tongue as far as you can."
I stuck it out, feeling silly at the spectacle I must have made. I heard
her moving around then she came very close to me. All of a sudden my tongue
came in contact with warm flesh. It was Julie, of course. Moreover it was
a part of Julie I'd never seen. Julie's breast and hard nipple were now
resting on my outstretched tongue.
She taught me how to lick it, how to tease it erect. Even though I couldn't
see it, it was incredibly exciting. Her nipple seemed to swell up in my
mouth, becoming over half an inch long and awfully thick. It was wonderful.
For the first time, I knew I was giving Julie pleasure as she moaned at my
efforts.
Finally she pulled away from me. I knew I was hooked.
As a special reward that night, she brought me off herself with her hand.
Over the coming months, Julie trained me to use my tongue extensively,
providing her pleasure whenever she wanted.
Punishments continued of course. In fact, several other women, mostly
friends of my Mom now knew I was spanked and punished in other ways. I was
sixteen by then but there was never any talk of being allowed to cover up.
The first 'outsider' to know I was spanked was my mother's friend Sara. She
showed up one day while I was buck naked, with my nose in the corner of the
living room. Mom had spanked me for backtalking to her. The doorbell rang
and Sara just walked in. She was over often. I didn't even have a chance
to beg Mom to let me go to another room before she was in it.
"Oh Hi Sara", my Mom said.
"What's this Sue?" Sara asked.
"Bobby was naughty and I had to remind his backside not to be rude is all"
my Mom replied. It's how he's punished in this house.
I was dying of embarrassment.
Mom and Sara left me in the corner of the living room to go into the kitchen
and chat. I heard quite a bit of laughter from there which I'm sure was
about me.
Sara would see me again only a few weeks later. This time I was on the
table with my bottom up (and filled of course) and nose down. Mom brought
her over to see me and I felt her jiggle the plug in my bottom. "Such an
obedient little boy" was her only comment.
A couple of months later after coming home late and not calling, Mom
actually sent me over to Sara's to get punished. She called first and I
heard her asking if she'd like to. Then I was sent over there holding the
hairbrush and the plug. I was mortified. Sara had a daughter that was only
a year older than myself. I was praying that she wouldn't be there. To my
relief, Sara seemed to be at home alone when I arrived.
Sara was obviously no stranger to this kind of activity. In no time I was
stripped and examined by her. She didn't bother using the plug in my
bottom. Instead she slide a rather large vibrator up there and then put me
into the corner of her living room.
"If it falls out Bobby, your bottom will be in for a surprise you might not
like."
Once she'd turned it on, needless to say, it became impossible to hold
inside. Not that I didn't try but it was less than 10 minutes before I felt
it slide out despite efforts to squeeze my sphincter as hard as I could.
"Uh oh", I heard behind me.
Alright young man, come with me.
Sara led me downstairs where there was a large table in the RecRoom. I had
to lay on my back on the table with my legs hanging over the side.
"Pull your legs up to your chest", Sara instructed.
>From a side drawer she pulled a number of nylon straps; the kind of things
that you often see on car roof racks holding down extra luggage. In a few
short moments, she had looped a strap around each bent knee and pulled it up
the level of my thighs and ankles. The straps had a one-way tightener, just
like a seatbelt and with a short tug, my upper thighs were welded to my
ankles.
Additional straps around my wrists were pulled to the head of the table and
fastened there. I was securely fastened but Sara was just getting started.
Addition straps now tied to the ones around my thighs and pulled them
downwards and sideways to keep my fastened down to the table and two final
straps were fastened to my knees and pulled wide open. I couldn't think of
ever having been this exposed.
Sara took one of her long fingernails and ran it slowly down the inside of
my thigh. My cock, with a mind of its own as usual, twitched erect.
"As I promised, I've got a surprise for you that you might not like too
much."
Sara pulled on a pair of latex gloves just like a doctor uses. She made
sure to do so where I could see her clearly. I was trembling. What did she
mean?
Sara held up a small foil packet and tore it open. I didn't understand what
came out. It looked like a really large capsule except that it was moist,
jelly like. It was perhaps two inches long and about a half inch wide.
"This is used on horses sometimes", she said. "It helps them 'present'
better. We'll see how well it helps you to present.
Sara reached down and touched the tip of the capsule to the center of my
already greased anus. It felt cold and gooey. She twirled the tip around
for a moment or two then slid the whole thing inside me. With the tip of
her long finger, she worried the gelatin capsule as deep as she could reach.
I didn't think this would be much trouble. After all, I'd just had a
rather large vibrator stuck deep up inside me.
Sara's finger slid out slowly, twisting as it came. She reached up and
patted my cock with a smile. "Don't be too smug young man. You don't know
what you're in for.
She took the gloves off and tidied up. All of a sudden, I felt a tickling
sensation in my bum. It started at the entrance, like a feather was
circling my anus. Then I could also feel it further inside. It was like an
itch that didn't go away, in fact, it got more intense by the second.
"Ah, I see you've noticed the ginger", she smiled. I'll be back down in a
few minutes. We'll see if you're ready to be a good boy by the time I'm
back.
As she walked up the stairs, the itching got hot. Second by second, it
seemed to get hotter until I though I was burning. I whimpered then tears
started down my cheeks. There was really nothing I could do.
Sara left me for about 15 minutes by which time I was a mess. My body kept
on trying to leap off the table and I was straining at every one of the
straps that held me down.
It was with tremendous relief that I heard the door to the basement opening
and the footsteps coming back down. I looked up ready to beg Sara to take
whatever it was out of me when I realized that it wasn't Sara at all, it was
Keri, Sara's daughter.
"She gave you the suppository huh?" said Keri.
I nodded miserably. I didn't trust my voice to speak without breaking into
sobs.
"I know, it's awful. She gives it to me sometimes. You're probably in for
more spanks and a cleanout before the burning stops."
If I had not been so uncomfortable, I'd have been quite interested in this
news but as it was I could barely concentrate on what she was saying.
More footsteps heralded the arrival of Sara and my Mom, an audience of three
to watch me squirm.
"Well Sara, this looks like it's pretty effective," said my Mom.
Sara smiled. It's worked wonders on Keri. Sara had my hairbrush in hand
and came up between my legs so she could look me in the eye. "Have I got
your full attention young man?" she asked. I nodded, "Yes Ma'am".
Ok, time for the second part of your spanking then. She dragged the
bristles down my cock and balls all the way along my hypersensitive anus
bringing a new moan from my lips then quickly reversed the brush and
peppered my behind with a hard and hot spanking that took my breath away.
For the few short moments that the spanking itself lasted I didn't even
notice the burning inside my bottom. It didn't take long for the tears to
come and the spanking then soon stopped.
"Now then young man. Can I count on some improved behavior between yourself
and your mother?" I was a model of obedience. I promised never again to
get into trouble if only she would make it stop hurting.
"Very well, we'll have to clean that hot juice out of you then."
Sara wheeled up a stand with a large rubber bag on it and a hose attached.
At the bottom of the hose was a strange device with what looked like the
kind of balloons that blood-pressure cuffs have. Sara pulled on new gloves
and under the interested eye of my mom lubricated my bottom again, but this
time with cold cream. The relief was almost immediate in the area right
around my anus.
The thick nozzle of the hose was slide up my rather willing bottom. In
fact, I don't think my bottom was capable of clenching to resist.
With a quick squeeze, the nozzle seemed to grow inside of me until I gasped
again. This nozzle wasn't leaving until Sara decided it should.
"It's called a ," said Sara. Very effective in preventing accidents.
With a turn of the clamp, I felt cool liquid rush down the hose and deep
into my body. There wasn't much I could do to prevent it. My belly swelled
up slowly until it felt tight and I was sure the water was going to come
gushing up my stomach.
It didn't of course. Once the bag was empty, Sara disconnected it. I hoped
we were done and that the straps would now come off. It was not to be.
Sara pulled out a bedpan confirming my worst fears. With a turn of the
clamp however, there was no way I could hold back. The nozzle was pulled
from me and the water followed instantly. Sara waited as everyone watched
me cry from the embarrassment.
Now it seemed my punishment was over.
Sara cleaned up and she and my mom started up the stairs.
"Keri, you finish off taking care of Bobby. You know what to do," said her
mother.
Oh no, I thought. There can't be more punishment.
All of a sudden Keri and I were alone. She looked hesitant. "Don't worry,"
she said. "Punishment's over."
Keri pulled out the cold cream and dipped her finger all the way into it.
"If you don't coat your rectum with this, the hot ginger will continue to
burn you for hours," she explained.
That being said, I felt her delicate finger rubbing it all around my anus
and then dipping into me. She ran her finger all the way in then out then,
with more cold cream in again. She was twisting it deep in me and all of a
sudden, I was so horny I thought I 'd split in two! Keri couldn't help
noticing.
"Don't worry, it happens to me too. I don' t know what it is about being
punished that makes me so hot."
With her finger deep inside my body, Keri reached over and took my hard cock
in her hand. She pulled it up slightly then bent down to give it a long
lick from bottom to top.
Wow! I had never felt anything like that before. She looked up and smiled
at me and then, as her finger twisted in and out, she licked it again, a
long, slow lick. That was all it took. I came in long spurts, over and
over and over.
Keri giggled. "I've never seen a boy come" she said. Looks like fun.
Keri took the straps off and handed me my shorts and t-shirt so I could get
dressed. We went upstairs together.
It was the first time Keri and I were in the same room for punishment but
not the last. I had occasion only a few weeks later to see Keri get just
the same treatment I'd gotten and saw, for the first time, a completely
naked girl. I had hair on my genitals but I saw that Keri had none. She
told me later that her mom made her keep it bare with hair remover.
Keri cried just like I did and I got to stick around and bring her to
completion when she was finished. It was great.
I'm 20 now and, while I don't live at home anymore, spankings haven't
stopped. Keri and I live together and you'd think that with our experience
the punishments would be a thing of the past. Not so. Julie still visits
us and when she does, both Keri and I are in for corner time and time with
our heads down and bottoms up. It turns out that Julie used to babysit Keri
too and, just like me, Keri was often punished by her.
Lately Julie has taken to bringing friends around when it's time for us to
get punished. Last week it was two girlfriends to took great delight in
giving us very long, very complete exams and "cleanouts" before Julie gave
us our spankings.
Tonight Julie has promised to bring over a girlfriend and her boyfriend who
can give Keri extra attention.
I suppose we should hate it but there's no doubt that when we're being
punished it's the hottest thing that you can image. Keri and I both come
like gangbusters and, as soon as everyone leaves, we're all over each other
like two alleycats using our tongues, finger, toys and whatever comes to
hand to bring us off again and again until we fall asleep together, curled
up like spoons.
All in all, it's not a bad life.
