Summer School & After School: The Ponygirl Omnibus Edition Read online

  “Well, if they wanted to enforce this paragraph,” her lawyer father mused. “Yes, I suppose forever. But that’s a long, long time and I have no intention of sending them any more money after the summer is over, so I doubt they’d keep you there gratis. Just remember that during the next twelve weeks.” Neither of them knew that in a few weeks, Dori would be in fact, literally owned by the school.

  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.

  “If this is what we wear for dinner, how do we eat?” Dori cried, by now totally frustrated by the new apparel and wondering what was going on.

  “You don’t have to worry about that, Dori,” said Winnie, smiling. “I’ve got a few other things here that will complete your outfit and later on we’ll talk about equestrian things, okay?”

  “Yeah. Sure. My knees hurt, I can’t use my hands, my tits are stuffed into teacups and my shoulders are killing me. What else are you going to do to make my first day as memorable as you promised?”

  “Well, shortly, you’ll get to meet the rest of the class and Miss Wright will greet you all.”

  “Oh boy,” Dori said sarcastically. “I can hardly wait.”

  “Sarcasm,” said Winnie pointedly, “is not appreciated here. I’d avoid that kind of remark, if I were you. When you are permitted to speak, it should be positive, not negative. Do you understand?”

  “Yes. I guess so,” Dori trailed off, trying to find a comfortable position for her aching arms and legs. She was still kneeling on the hooked rug and the position was becoming untenable.

  All of this gave Dori more than second thoughts. What was happening here? The breeches were odd enough and the shirt was close to some sort of straight jacket. She was now kneeling in a bedroom of a farm house, hundreds of miles from home, while a woman she had never met before secured her into attire that she knew she wasn’t possibly going to get out of without some help. It was almost erotically stimulating, but there was also an element of fear. Winnie was extremely dominant and Dori had felt this since they first met. Now the other girl fussed about her head with pins and rubber bands, pulling back Dori’s long dark hair into a ponytail and securing it with a braid. When she finished, the braid was more of a topknot and stuck up from the top of her head, slightly back of the center of the skull.

  “How’s that?” Winnie asked, proud of her quick work. “Do you usually ride with a braid?”

  “Yesss… Sometimes,” Dori said slowly, uncertainly.

  “Well,” said Winnie. “You will ride with one here.”

  Chapter Four

  Standing Welcome

  Dori knelt in the brightly-lit room. She could see the spotlights mounted in the ceiling and the bright whitewashed walls reflecting the light. She could see the tops of the heads of her classmates and the instructors as they busied themselves with their charges, but she could not see much else because her head was held back with her face pointing at the ceiling. As soon as she finished with Dori’s hair, Winnie fitted her with a heavy leather bridle and bit, among other things, before bringing her downstairs to the pre-dinner meeting of the class. Her new
classmates were staring upwards just as Dori was and they all looked quite astonished and somewhat unhappy about their state. Instructors and grooms, male and female, hustled about, tightening straps and adjusting head harnesses on the class. One or two of the girls were crying and their instructors ignored the whines and pleas that came from behind drawn back lips, the rubber plug gags and bridle-distorted faces.

  Dori wore the bridle Winnie had fitted to her head after the two had at first argued over the arrangement. Winnie had tried to persuade the younger girl to wear the leather and steel device without any struggle.

  “If you just go with this, I will make it easier for you. Fight me and it will get done anyway. But it will hurt. I can always get a couple of male grooms to come in and help, you know.”

  “Yes. I know. But I really, really don’t want this. I’m tired. I hurt. My legs are killing me and my tits are being crushed. This sleeve is yanking my arms out of the shoulder sockets or whatever they’re attached to. Come on, Winnie. This isn’t fun or funny and I paid a lot of money to come here to ride, not to be abused.”

  “Humm,” mused the riding instructor, stepping back and surveying her charge. “I see. You want to go home now?”

  “No. Not home. Just to bed. I’m really tired and this isn’t my thing. I had a boyfriend in high school who tied me up once or twice and it was okay, but this is too much and it’s too tight, damn it.”

  “Okay,” said Winnie. “We’ll do it my way.” She was behind Dori and as she spoke, she pulled down on the girl’s new braid and bent Dori’s head back almost painfully until the girl stared at the wooden wagon wheel chandelier over the bed. Dori yelped from the sudden strain and as she did, Winnie jammed a rubber plug and metal bit into the open mouth.

  “Mummph, ounnhph uuuuoh,” came the instant response.

  Winnie forced the plug all the way into Dori’s howling mouth and brought the steel bit back until Dori’s cheeks were distended and pulled firmly back, baring her fine white teeth and the black rubber plug that filled the inside of her mouth.