Summer School & After School: The Ponygirl Omnibus Edition (2 page)

Chapter Three

Dressing for Someone Else’s
Pleasure

“I’ll help you
get ready. I don’t think you’ll be doing this alone or walking downstairs in
these,” said Winnie, a cute five-foot tall blond in riding attire, who stood in
the half open bathroom door.

She arrived in
the room while Dori was in the bathtub, making her presence known by knocking
on the door and unabashedly peering into the bathroom to find Dori partly
submerged in the tub full of hot water and bubble bath.

“Hi Dori. I’m
Winnie and I’m your keeper,” she began, “unless you want a guy as your
chaperone,” she added with a grin.

“My what?” Dori
sputtered as she decided not to sit up in the tub, seeking the poor visual
security of the few soap bubbles and washcloth.

“I’m your
escort, guide, proctor, whatever.” Winnie grinned back, surveying the soaking
body and the pink nipples poking up through the cloudy bath water. “I’m here,
as they say in the IRS, to help…That’s a joke. My Dad works for the IRS.”

“Oh. Okay,” said
Dori, pulling the washcloth up over her floating chest. “I’m about to get out
of here. Would you pass me that robe, please?”

“Sure,” Winnie
said and she picked up the white terry robe lying on the small stool near the
door and walked out of the bathroom with it.

“Hey. That’s my
robe.”

“No, it’s not.
It’s school property. Come out here and get it…after you dry off,” chuckled
Winnie, and she sat down on the bed.

“What’s the
idea?’ Dori called through the door, hoisting herself out of the tub and drying
off with one of the many fluffy white cotton towels on the racks.

“Oh, don’t
worry. I’m just kidding around. You want me to leave? I’ve brought up your new
riding outfit. It’s all here in the Filene’s bag.”

“No. Don’t
leave. Wait a minute. I’ll be right out,” Dori said. “What’s a Filenes?” she
added.

“Filenes,
stupid,” Winnie simpered in a sing-song little voice, mimicking Dori, “is a
giant rummage sale in the heart of downtown Boston. We go down there and shop
when we’re really bored.”

“Oh,” was Dori’s
muted reply as she hurried to dry herself.

A moment later,
wrapped in the towel, Dori came out of the bathroom and stopped by the bed,
giving Winnie a close inspection. Winnie was a pert, athletic blond of medium
height, with a small round face, large china blue eyes, more than ample breasts
and long legs that seemed to end up around her shoulders. She wore a tight,
white, short sleeve T-shirt, tighter jeans and black, custom riding boots.
Probably Hermes
, thought Dori, admiring
the boots and the rest of the custom body that filled the casual outfit. Dori
had already decided that Winnie had bucks, probably plenty of them, judging
from the immaculate, yet casual, hair style; the perfectly manicured nails and
the sparse, but expensive jewelry. She was pretty sure that the watch on
Winnie’s left wrist was a real Cartier, as was the heavy gold bangle bracelet
on her right wrist. The bracelet had two small rings attached and a tiny
padlock that seemed to be really functional. It was clearly a costly little
item from Cardin or Hermes. She also noticed that there was a duplicate bracelet
next to the watch on Winnie’s left wrist.

Winnie got up
and went to the large shopping bag on the floor and started sorting through the
contents. “Put these on first,” she said. She handed Dori a pair of what
appeared to be tan riding breeches and matching brown boots.

“What? What do
you mean? I’m not ready yet. I need to do my hair and make-up and all sorts of
stuff. I just drove up here from Virginia,” Dori said with a bit of a whine in
her voice. She looked first at the tan material and at the dark brown,
well-polished boots Winnie held out to her. The breeches had very short, wide
legs with a leather belt at the top. The belt too was wide, nearly six inches,
and seemed terribly small, even for Dori’s tiny waist.

“Yeah, yeah. So
has everyone else. Lots of people just got here for the summer session. I’m
here year ‘round,” she added. “But try these on so that if they don’t fit, we
can make changes before dinner. You don’t want to be late for dinner on the
first night and I must tell you, you absolutely, positively do NOT want to be
out of uniform tonight.”

“Out of uniform?
These look pretty strange,” said Dori, half to herself and half to Winnie.

“You bet they
are. Here, I’ll help you now so we can get started.” She led Dori into the
dressing area and waited with her hands on narrow hips for the younger woman to
strip out of her towel.

Dori complied.
She really had no problem undressing in front of other women. She knew most of
them would find her figure as good as or better than their own. As she took off
the towel, she saw Winnie’s eyes following her admiringly, but with perhaps
more interest than Dori expected. Winnie’s light blue eyes fastened first on
the large, high, stargazer breasts with soft pink nipples, then moved quickly
away to lock onto Dori’s closely trimmed bikini thatch of light brown hair. Her
eyes stayed there a very long time, which made Dori a bit self-conscious,
before they moved on.

“What about
underwear? Is there any in the bag? I brought some, but it’s in my car and the
car is down the road about three miles.”

As Dori looked
for a way to get into the strange-looking breeches, Winnie said: “Oh, what the
hell, skip the panties. You won’t need them. Put these knee-highs on and next
the boots, then the pants.”

“Huh? No panties
under the breeches?”

“Nope. You’ll
see in a minute. We are most particular about what we wear to ride,” Winnie
explained.

“Okay, but I get
pretty sweaty riding without some sort of underwear and I do not like thongs.”

“I agree. No
thongs,” said Winnie.

“So, how do these
things go on…why…why there’s no crotch in these! What the hell!” sputtered Dori
as she inspected the breeches closely.

“That’s right.
You’ll see. Here, let’s get these boots on first. I’ll show you how to put the
breeches on.”

Boots first, THEN breeches
? Dori thought.
This is really weird!
She sat down on
the large colorful hooked rug and pulled on a thin pair of tan, knee-high
stockings and then pulled on the boots. They were tight and came up a little
shorter than she was used to, but they fit fine. The leather was soft and
smooth, and the boots almost felt as if they had been broken in for her.
Bending her legs, the top of the boots came right up behind her knee, although
they didn’t cut into the skin or press so as to stop the circulation. She saw quickly
that they had been cut correctly for her legs.
Well, there’s where a good five or six hundred bucks of tuition went,
she mused, smoothing the boots out over her calves.

“Beautiful!”
Dori exclaimed. She took the breeches and tried to step into the wide legs.

“Wait a minute,
let me show you how this is done,” Winnie said. “You kneel on the rug and put
your knee into the left leg, like this.” Winnie helped Dori place her bent left
knee into the tight, Lycra and spandex-based breeches. The fabric gripped the
bent limb tightly, but Dori’s small, well-muscled leg slowly inched into the
short leg of the breeches. As her knee reached the bottom of the pant leg, the
top of the leg fit exactly at the top of her thigh and only her small, booted
foot remained outside the legging. Winnie fastened a strap that went around the
ankle and the top of the thigh, pulling Dori’s booted heel tightly and closely
against her smooth, Lycra-rounded butt. Another small strap at the bottom of
the leg slipped under the heel of her boot and kept the breeches leg tight
against the ankle. Dori was mystified about this garment, but also fascinated
enough to continue. She balanced herself on the bent left knee and forced the
right one into the other pant leg, getting needed support from Winnie as she
did so.

In another
minute, Dori knelt on the hooked rug, both legs encased in the skin-tight
breeches with her ankles strapped back against her buttocks and her boot toes
digging into the rug for support. Her entire crotch was bared, from behind to
just below her navel. Her closely clipped pubic hair was centered in the middle
of the open crotch of the breeches. Above her crotch, covering her navel and up
to her waist, the breeches were conventional with a brass zipper fly and
buttons at the waist. The belt was mercilessly tight, cinching in her 23-inch
waist to something closer to 20 inches. Dori gasped as Winnie tightened the
buckle. She was surprised to see that it had a small lock and this was closed
and locked once the belt had been tightened.

“Hey, why the
lock?” Dori asked.

“So you don’t
take them off, Honey. Isn’t that obvious?”

“Yeah, but…”
Dori stopped. “How long will I have them on? They’re really tight and I don’t
see myself going to dinner this way.”

“Oh, everyone
manages, sooner or later,” Winnie said cheerfully. “It takes a while. Anyway,
we’ve got a top for you in the bag. Let me show you.”

Winnie pulled
out a white turtleneck shirt. At least it looked a little bit like a regular
turtleneck until she brought it closer to Dori and started to fit it over the
her head. The shirt had several additional accessories like no turtleneck shirt
Dori had ever seen. It had two short white nylon zippers on the chest and one
long, heavy-duty nylon zipper in the back. The small zippers ran vertically up
both sides of the chest. Behind the zippers, a built-in bra had been stitched
into the shirt, the straps hanging loose and unfastened from inside. The shirt
had no sleeves in the conventional places, but there was one large, single
sleeve in the back and the large zipper was stitched into this sleeve.

“Put it on,”
Winnie insisted, pulling the collar over Dori’s head. Dori gathered her hair in
one hand, closed her eyes and stuck her head through the hole in the collar,
noting the zippers in the front, the built-in bra inside and the single sleeve,
which seemed to be in the wrong place for either arm.

“It’s got
zippers and a bra in it,” Dori said as she was trying to poke her head through
the neck of the shirt.

“That’s it. An
‘all in one.’ You’ll see.”

“What’s with the
zippers?”

“You’ll see.”

“Great. What a
goofy shirt!”

Dori’s head
popped out the top of the shirt, the rest of the fabric resting on top of her
shoulders.

“Bring your
hands together behind you,” Winnie said.

“What? Why? This
isn’t going to work, Winnie. I don’t think I want to do this,” she started to
whine.

“DO IT. DON’T
COMPLAIN OR YOU’LL BE SENT HOME,” the other girl shouted, her face getting red
and her eyes almost popping out of their sockets.

Astonished and a
little frightened by this older girl who had walked in on her in the bath, Dori
forced herself into an outfit that would obviously leave her quite helpless.
“Okay. I’ll try, but this hurts,” she moaned as she brought her small hands
behind her and felt the other girl grasp both wrists in one hand and pull the
shirt down and away from the collar. The shirt was a mixture of Spandex and
pure Lycra fabric and it stretched easily. Struggling a bit to pull the back of
the shirt down and over Dori’s limbs, Winnie placed both of Dori’s hands in the
cuff of the single sleeve and pulled the stretchy fabric slowly up around the
her arms. As Winnie did this, she closed the large zipper, pulling it upward
towards the collar, Dori’s forearms came together inside the sleeve and her
elbows were pulled together as well. Her shoulders, pulled back and strained
with the position, forced her breasts out and into the bra cups inside the
shirt.

Winnie pulled
the shirt down over Dori’s large chest, further fitted the built-in bra over
the full breasts and extended the sides of the interior bra straps around
behind Dori’s back, fastening the three metal clips. They weren’t exactly
standard bra-type
clips, and Dori couldn’t see what Winnie
fastened behind her back, but she heard the three separate snaps of small
locking devices. The bra tightened even more firmly around her chest and forced
a bit of breath from her lungs. It was very, very tight and when Dori tried to
take a full breath she found that it was almost impossible, for although the
bra stretched a little bit, it had almost no give to it! It was far from
comfortable.

“Winnie,”
breathed Dori. “I’m really afraid this is far too tight. Don’t you have a
bigger size?”

“Humm,” mused
the older girl. “You are a 38-D, aren’t you?”

“Well yes. I
usually am. But you know, sometimes I need more room…” She stopped, still
wondering why she was allowing herself to be dressed in this weird outfit.
Clearly, now she couldn’t even stand up in this gear, let alone go riding.

“This bra feels
like it’s about a thirty two or less and the cups are just too small for me,”
she said breathlessly to Winnie. “I wish I was smaller, but this thing isn’t
helping at all.”

The cups of the
bra were made from a stiff, molded material stitched into the shirt and they
gripped the girl’s breasts with extreme closeness, powerfully pushing her
entire mass of breast tissue together, upwards and towards Dori’s neck. Her
nipples felt like they were being crushed in some sort of vice and the entire
shirt was becoming hot and uncomfortable.