You'd never believe that my job could be tough. In fact, when I try to
tell people that it is, they generally laugh. You see, I'm the
Headmaster at a girl's boarding school. But there are aspects of the job
that call for service well above and beyond. Take what happened with
Amy, for example. She was in her senior year, only a few months away
Our school is mainly patronized by parents of high school girls who want
their daughters to 1) meet eligible young men, and 2) graduate virgins.
In fact, they'd prefer if their daughters married as virgins. Better
yet, they should go their entire lives, marry, give their parents
grandchildren, and die virgins. No one said parents were rational, at
least not ours, anyway. In fact, our founders came up with some rather
bizarre rules regarding the girls' conduct, and the boards since have
never made them more rational. When they have made changes, they've
generally made things even more bizarre.
So, when I heard, one Sunday night, that Amy had been found with a man,
or more accurately, her boyfriend in her room, and had been caught
beginning the act itself, I knew I was not facing a pleasant Monday. I
wasn't looking forward to what would be coming, but the rules of the
school were clear. At precisely nine o'clock, Amy was brought into my
office. She was wearing a pink top, and a short, pleated skirt. As I
found out as soon as she sat down and crossed her legs, she was also
wearing pink silk underwear: a matching set of panties and garters with
stockings, as well as bra (I didn't find out about the bra till later)..
I told her what she'd been accused of, and to my relief, she didn't deny
it. She just hung her head, let her skirt ride a little higher up her
thigh, and gave a little sob.
"I don't know what I was thinking of, Doctor," she said, tearfully.
"I've never done anything like that with a boy, before. I guess I was so
much in love that I lost my head."
I explained that, under school policy, her reasons, past record, and
mitigating circumstances counted not at all, and she would have to take
her punishment, as dictated by school policy. I explained that it was
either that, or we would notify her parents, and demand they remove her
from school immediately. She begged me not to do that, saying that any
punishment would be preferable, and that she'd be glad to endure it if
it meant that we kept her secret.
"There's a policy of secrecy about these punishments, Amy," I told her.
"Once you decide on this course, there's no turning back, no changing
your mind. You will get the punishment, exactly per the rules. Do you
understand that? Once I tell you what I'm going to do, I must do it,
even if you decide you'd rather face your parents."
She looked at me with a look that tried to combine tears and gratitude.
"Oh, Doctor, I know that nothing you'd do to me would be that bad. I'd
rather face anything you did to me than my parents," she vowed.
"Well, then, I'll tell you what I have to do," I began, "if you're
She insisted she was, and uncrossed her legs, which is how I learned
that her panties matched the garters. I should mention, I had found her
extremely attractive since the first day she arrived at school. As
Headmaster, of course, I'd never have dreamed on acting on those
feelings, with her or any student, but she was special. Not that she was
the most gorgeous girl in the school: others had better features, better
legs, better asses, better... Well, you get the idea. But somehow, the
combination she had made her the most beautiful woman I'd ever seen,
and, coming from a Headmaster at a girls' school, that means a lot. Of
course, one can never overestimate the aid youth gives to anyone's
appearance, but she would have been gorgeous without it. I certainly
didn't want to do what the regulations insisted I must, but my duty was
my duty, and we WASP's always take duty much too seriously. I picked up
the phone, and had the school nurse come in.
"Well, Amy," I began, "now we start your punishment. Miss Preen is here
to serve propriety, and to make sure that no medical harm comes to you,
however remote the chances of that. Your punishment begins with you
removing all your clothing."
Her eyes grew wide at my command, her mouth dropped open, and she stared
at me in disbelief. "You're kidding me, aren't you?" she asked. "You
don't mean that?"
I assured her that I meant exactly that. "I'm certainly not going to
punish you for sexual activity by engaging in it with you, but your
punishment is your punishment. And it starts by removing all your
She looked at Miss Preen for support, found none, and looked back at me.
"Not really? Not all of them?"
"Really. And every stitch." I was immovable. She stood up, shaking her
head as if stunned, and began unbuttoning her blouse. (That's when I
learned about the bra.) She stepped out of her high heels, undid the
clasp on her skirt, and let it fall to the floor. Standing in front of
us, in bra, panties, garters, and stockings, she melted my heart. She
was divine. Her breasts were exactly the size I'd have made them, if
anyone had asked, and the bra was the type where you could see her
nipples and make out the aureole. Her tummy swelled gracefully over the
top of her panties, and her thighs were divine columns of young, smooth
flesh. I've always preferred women who didn't trim their pussy hair, and
Amy fulfilled my fondest dreams. Her lips showed through the panties,
full, young, and ripe. Reaching back to undo her bra, she gave me a look
at the loveliest ass I'd ever seen. It more than met my expectations for
being round, and delicious. Next came the garter belt, the stockings,
and finally, shivering more from fear than cold, she took off her
"All right, Doctor," Miss Preen intoned. "You've got to do the
examination now. I'll check it out with you."
"What does she mean, examination?" Amy questioned, her voice shaking.
I forced myself to look right into her eyes, and tell her forcefully,
"Turn away from us and bend at the waist, as far over as you can. Touch
your toes, in fact," I added, feeling stronger as I spoke. She hesitated
a moment, so I barked at her "Now!" She complied, and the nurse and bent
over, examining her ass, particularly the hole.
"No problems there," Miss Preen informed me. "She'll be able to take the
large size easily, although I must say she does seem to be a virgin,
back here at least."
I had Amy straighten up and then gestured for her and Miss Preen to be
seated, as I went back behind my desk, and emulated them. "Now Amy, I'm
going to explain the next phase of your punishment to you. Do you know
what an enema is?"
She could only look at me in horror, mouth open. I spoke more sharply,
and repeated the question. She nodded her head slowly. "You're going to
come with me, next door, into the conference room. The table has been
covered with padding, a pillow in the center, and a towel covering the
pillow. You're going to lie on the table, with your hips on the pillow,
and I will give you your enema there. I should warn you, seated around
the table are the entire male faculty and staff, as well as four of your
girl friends. At the head of the table, the end you'll be facing, is
your young man from last night. He's here under threat of criminal
prosecution, not because he wanted to be. None of them will speak to
you, but they'll all see the process, from beginning to end."
"You don't mean they'll see me, I mean, in the bathroom..." she began.
"No, but they will be there while you take the enema, and for the full
time you hold it in. Miss Preen will get the bag ready, and the
solution, while you and I go in there, and I get you ready."
Now, the reasoning behind this method of discipline is obvious:
humiliate a girl beyond bearing, and she's not likely to repeat the
offense. I've always had my doubts about that, but the few times I'd
done it up till then, it had always worked. That's as far as we knew,
anyway. I had to take her arm to get her off the chair, and she walked
towards the door, as if in a trance. When I opened it, and stepped back
for her to precede me, and she stood naked in the doorway, she froze in
horror. Everyone in the room was staring at her, as who wouldn't, and I
had to help her into the room, and onto the table. She tried to bury her
face in her hands, but I informed her very sharply, that she had to keep
her eyes open, and be making eye contact with someone at all times. I
felt sorry for her, she had no idea where to look.
As I pulled on a rubber glove, and began smearing KY Jelly onto it, I
did begin to feel quite powerful. I suppressed the feeling, and
explained that I was about to lubricate her ass. Of course, I said it
more genteelly. I used my free hand to pull one buttock away from the
other, and smeared the jelly on her hole. Then, I gently circled it with
my finger, probing gently. Gradually, I probed more forcefully, pushing
my finger in a little, letting her muscle push it out, then back in a
little further, then out again, and so on, until I finally achieved
penetration, pushed past the muscle, and moved my finger in and out of
that marvelous ass, getting her nicely greased up. She gave a very low,
soft moan at this point, and I got dizzy with the power of it all. The
moan changed to a cry of horror as Miss Preen reentered, carrying in the
The bag was the hospital type, clear plastic, closed top, with a long
hose. It held three quarts of very warm water, and was positively
bulging. At the bottom of the hose were a clamp, and then a large douche
nozzle, the type normally seen on feminine syringes, rather than the
smaller, regular douche nozzle. It was a full nine inches long, and at
its thickest, about twice as thick as a large man's finger. It glistened
with KY Jelly. She began to sob, and beg me not to make her take the
enema, but I coldly reminded her that she'd preferred anything to her
parents' wrath. I gave her ass a few more strokes with my finger, and
then took the nozzle from the nurse.
"This will go into you much more easily if you try to relax," I said,
knowing it was useless. No one, least of all a girl her age, could have
relaxed in that situation. "You wanted a man to put things into you, and
inject liquids last night, didn't you?" I demanded.
She whimpered that it hadn't been like this.
"No, but this is a punishment, and you will take it!" I ordered. "I want
you looking right into your young man's eyes, now. Good. Now keep doing
that until I tell you to look around." I was surprising myself, getting
an unexpected pleasure at her helplessness.
I probed at her with the nozzle, and could see her ass tightening up.
Ordering the nurse to pull her buttocks apart, I placed the nozzle
against her hole, and held it firm. "Lift up your hips," I commanded.
"Show us all what you did last night!" She squealed a little, but
obeyed. Slowly, her tight little hole expanded, and began to take in the
nozzle. I pushed it against her, and commanded her to relax. As the
thickest part of the nozzle inched past the muscle, her tightening
pulled more of the nozzle into her. I got it in further the same way I
had my finger, in a little, out a little, back in some more, etc. It
took a few minutes, but finally the entire nine-inch nozzle had
disappeared into her ass. I made her lift her head and turn around to
look at me, as I held up the bag.
"Now, Amy, you know what the alternative to taking this enema is, don't
you?" She could barely squeak out a yes. Her whole body was trembling.
"So, considering the alternative, you actually want this enema, don't
you?" She nodded, but I ordered her to say it out loud.
"Yes, Doctor," she whispered in compliance, "I want you to give me my
I ordered her to repeat to everyone in the room, making eye contact with
each one as she said it, "I want the Doctor to give me my enema."
I ordered her to look at her young man, and then opened the clamp. The
sudden rush of the water, filling up her ass, unnerved her, and made her
cry out. Unheeding, I held the bag as high as I could. As the water
flowed into her, I made her look at everyone in turn, and tell each one
it felt good.
"You are enjoying this, aren't you?" I taunted. "Maybe you should wiggle
a little, and squirm those hips like you did last night." She did as I
told her, and actually began grinding against the pillow. When she had
taken about a quart of her enema, I noticed that her pussy was beginning
to leak a little juice.
"Did you like it when he did this to you?" I asked, and began to slide
the nozzle in and out of her, fucking her ass with it. She could only
moan in reply, and grind faster and harder. The juice was flowing out of
her pussy by now, and she had to clench her ass ever tighter, as more
water filled her up.
"Oh my God," she exclaimed, "it's too much now, the pressure is too
much," she complained. But she never stopped pushing against the nozzle.
I told her she had one quart to go, and said she wanted to show us all
that she could take it, didn't she.
"Yes, I do want to take it. All of it. Please go on," she begged. She
was writhing so hard, and moaning so loud, and towel was soaked with her
juices. Finally, she had the entire bag in her ass, and I closed the
clamp, and concentrated on fucking that ass for all I was worth.
After a few moments of this, her whole body tensed, she shuddered
several times from head to toe, and came so hard that a rush of pee
gushed out of her pussy. Trembling, she relaxed and lay still, in a
puddle of her own fluids. Of course, now that the distraction of sex was
gone, she felt the full effect of three quarts of water in her, and the
pressures that came with them. I told her that she had to hold it in for
fifteen minutes, no matter what, and that if she lost the enema, she
cleaned it up.
I ordered her to make eye contact again, with each person in the room,
and thank them all for watching her take her enema. The shame started
returning, and I had to give her ass a hard smack to get her to do it.
She was blushing furiously, and we could all see each spasm of pressure,
as the enema went to work, trying to do its job. She began asking for
the bathroom after five minutes, pleading after ten, and might have lost
the enema, if she hadn't had the nozzle for her sore, tired hole to grip
onto. Finally, time was up. She was so full, and having such trouble
holding in her enema, that Miss Preen and I had to help her off the
table, and lead her out of the room, one of us holding her arm on each
She might have stayed there forever if she'd known the next part of her
ordeal: with the nozzle still disappearing up her ass, and the bag over
her shoulder, she had to walk between us, naked, with her belly bloated
from the enema, all the way to a bathroom on the other side of the
school. As she met each person, she had to explain that she was holding
in her enema, and needed to get to the bathroom as quickly as possible.
Within an hour, everyone in school knew what had been done to her.
For the rest of her time at school, Amy had a lot of trouble making eye
contact with me, knowing I'd been the instrument of her shame. She
definitely couldn't look at me without remembering what I'd done to her,
no more than I could look at her without remembering how she'd looked.
When she graduated, with honors, I thought I'd seen the last of her.
A few nights later, however, she showed up at my door, and I invited her
in. She came right to the point. "I've done it again," she began. "I had
sex last night, with that same guy."
"Well," I said, "You're over eighteen now, and can do what you want
"No I can't," she lamented. "I wanted to take an enema before we did it,
and he flat out refused. He told me I was sick! You know better than
that, don't you?"
I certainly couldn't say no to her. Thank God I'd saved that bag!