A few minutes passed before Lindy heard footsteps approaching. She shut her eyes tight against the embarrassment of the moment when Jackson would first lay eyes on her naked form. What would he think of her generously proportioned breasts and hips? She had tried to lose weight recently, to make herself look more like those girls in magazines but with money in short supply, chocolate had been the last indulgence she could afford and on long, lonely days she’d really gone to town on the peanut butter cups. She hoped that when he saw her, Jackson would not be disappointed.
“Well, I guess she did as she was told, but it’s not a very welcoming sight.” Jackson’s voice seemed to tease rather than scold as he walked into the room to find Lindy hunched over in a defensive posture, the tension vibrating off her in waves. “What do you think, Dr. Gilbert?”
“I think that the young lady has a lot to learn and that there’s nobody better qualified to teach her than you, Jackson. Now, let’s get on with it, shall we?”
The doctor’s tone was brisk and Lindy tried to decide if that was some comfort. If the woman was all business, as she seemed to be, then perhaps this first trial would be over with quickly.
“Open your eyes, Belinda,” Jackson commanded. Reluctantly, Lindy obeyed and found him standing over her, watching her closely. “Now, stand up and move to the center of the room.”
Blushing deeply and excruciatingly conscious of her nakedness, she got up from the bed and took the couple of steps required to reach the middle of this very small room. Glancing surreptitiously at the tall, friendly-looking brunette in the velvet evening gown, she surmised that this was the doctor. It felt strange to be standing here with not a stitch on when the other two people in the room were not just fully clothed but decked out in their finery. Her instinct was to run but under the weight of Jackson’s approval, she just stood there and waited. She might not have done anything remotely like this before but she was aware that it was best not to move until given express permission to do so.
Jackson stalked slowly, deliberately around her, his eyes running up and down the length of her body, taking in each minute detail. Fighting the urge to try to cover herself, she wondered what he was thinking but, as usual, his face gave nothing away. As he positioned himself behind her, she shuddered in anticipation. He was close enough that she could feel his breath on her skin and it made her hair stand on end. Shivers danced down her spine as she moved closer, still not touching her.
“Hands behind your back and keep them there.”
Lindy obeyed immediately, placing her hands behind her and interlinking her slender fingers to make it easier to hold the position that, she noticed to her mortification, made her breasts thrust out in front of her. She had little time to worry about the blatantly sexual stance as, suddenly, Jackson’s hands were on her. They were light at first as they began their exploration of the mounds of silken flesh. His fingers teased the taut peaks of her rosy nipples and she could not prevent a startled gasp from escaping her as his foot moved to part her legs, spreading them wide.
“Beautiful,” he murmured as he continued to run his hands over her quivering body. “Don’t you agree, Kristin?”
“Yes, she is very beautiful but you were right to be concerned. She is too thin.” Lindy’s impulse to protest that she was anything but underweight was quelled as Dr. Gilbert smiled at her with what appeared to be genuine warmth, making her feel as though the woman could, perhaps, be trusted. “Now, I need to ask if there are any medical issues we need to be aware of?”
The question caught Lindy off guard. She had thought the examination was just part of a game, not a genuine means of ensuring she was healthy.
“Diabetes, blood pressure, anything like that?” the doctor prompted when Lindy did not respond.
“Uh, no, nothing. I’m never sick.”
“That’s good, and what about contraception?”
“I get shots for that.”
She emitted a moan as Jackson’s grip tightened around her breasts as though in reprimand for not revealing that information earlier when he had asked whether she had birth control pills.
“Okay,” Dr. Gilbert continued. “When was your last shot?”
“About two weeks ago.”
“Good. So, what about sex? When did you last have intercourse?”
Lindy shifted from one foot to the other, concerned that her answer was going to make her seem like some sort of freak compared with other women her age.
“About three years ago. Maybe more.”
She hung her head as the doctor raised a surprised eyebrow, no doubt wondering why a woman with such a woeful sex life needed to use contraception, but an unexpected grunt of approval from Jackson told her there was no need to feel embarrassed.
“Okay, then, we can proceed. Jackson, please examine Belinda’s breasts while I check her responses.”
Jackson’s large, rough hands cupped Lindy’s breasts, holding them almost with reverence as he tested their weight. She wondered if he noticed, as she had, that they were the perfect fit for his palms. He began to caress her breasts, applying increasing pressure as he examined every inch of them. She moaned as his touch became firmer, the squeezing of her flesh a little more insistent. Taking first one nipple and then the other between his thumb and forefinger, he pinched hard. Even as she gasped in pain, intense pleasure coursed through her to reach the most intimate part of her body. She groaned and squirmed helplessly in his unyielding embrace, lost in the moment as wetness began to pool between her gaping thighs.
As she continued to writhe in Jackson’s arms, a movement on the other side of the room alerted her to the fact that the doctor was slipping on a pair of latex gloves. Dr. Gilbert approached her, smiling at Lindy’s wide-eyed stare and, without warning, thrust two long, elegant fingers between the young woman’s legs to find her drenched in feminine juices. A jolt of electricity shot straight to Lindy’s womb, which clenched tightly as Jackson tugged her nipples hard. If he had not had his arms around her, she would surely have crumpled to the floor.
“She responds well to breast stimulation.” The doctor held her hand up to show Jackson the moisture glistening on her gloved fingers. “I imagine she would enjoy having those pretty little nipples clamped, perhaps a light flogging.”
Lindy almost melted with desire at those words. She groaned and squirmed in Jackson’s arms. Her face flushed as the doctor threw back her head and laughed.
“Guess I was right about that. Now, let’s see how she does with the rest of the examination. Help her onto the bed, please, Jackson.”
As he began to steer her toward the bed, Lindy felt a sudden surge of panic. Now back on the other side of the room, the doctor was rummaging through her medical bag. Lindy’s eyes stood out on stalks as she watched the glamorous older woman retrieving a sterile package, which she placed at the end of the bed. Lindy could not see what it contained but as Dr. Gilbert took a tube of lubricant from the bag, she just knew it meant more humiliation was in store for her.
She began to struggle to free herself from Jackson’s hold but it was useless as he held her with ease. A couple of harsh slaps to her right thigh lit up her flesh, stunning her and causing tears to pool at the corners of her eyes.
“Please,” she begged. “I don’t want to do this.” She started to cry, swamped with emotion at the enormity of what was happening. She’d imagined this scenario a hundred times before as she lay in bed, her own fingers probing the warm wet folds of her pussy before thrusting in and out of her needy cunt. Thinking about this had brought her to a shattering climax every time. Her fantasies had only intensified after she’d first set eyes on Jackson Davies but the reality was overwhelming. Already she felt exposed and she had a feeling things were about to be ramped up a notch.
Jackson spun her around and held her at arm’s length, leaning forward to study her face as he spoke.
“This is what you agreed to.”
“I know,” she sobbed. “But I’ve changed my mind. I can’t see any point in this examination.”
“The point is to ensure that you are fit and healthy because I don’t want to risk harming you in the next few weeks.”
It sounded reasonable enough but, right now, Lindy was barely capable of rational thought. She had opened herself up more than she ever believed she could. Did Jackson realize just how big a deal it was for her to be naked in front of strangers? This was all so confusing. Never before had she felt so turned on and yet so ashamed all at once. Even as she relished the thought of having her body explored so intimately, her mind chastised her for it. Surely this was not what normal women craved? There must be something wrong with her.
She knew that they had barely gotten started but she wasn’t sure she could expose herself to more. Was the promise of experiencing the sensations her body yearned for enough to override her fretful mind? Perhaps things were just happening too fast.
“I realize that, but…”
“But nothing, young lady. You do not get to pick and choose what we do here. What do you imagine it would be like if you had been sent to prison?”
Lindy shrugged her shoulders, tears falling in earnest now to prevent her from responding verbally.
“They would strip search you to make sure you hadn’t smuggled anything in for a start. They would examine you inside and out with no thought to your feelings. You’d just be one more lowlife for them to deal with and they wouldn’t care if you were okay afterwards.” His tone was brutal and it emphasized to Lindy how badly he wanted to get through to her. “Now, if you’re telling me that you’d prefer to have someone who doesn’t give a damn about you as a person putting their hands all over you in some grubby prison cell than have Dr. Gilbert do it here with me looking out for you, then I’ll drive you to the police station and you can turn yourself in.”
She blinked the tears from her big blue eyes and looked up into his face to see that he was deadly serious.
“Or,” apparently understanding the confusion she felt, he softened his tone, “you can do what you promised and give me your total obedience, knowing that I have your best interests at heart.”
For the first time, as she stared up at him, she saw something other than indifference on his face. There was concern for her and a flicker of some deeper emotion she couldn’t quite read. Whatever it was, she understood that, no matter what happened, how unpleasant any punishments he dished out might be, he would not allow any harm to come to her.
“Okay,” Lindy sniffed. “I’m sorry I panicked. It’s just that…”
She gestured toward the doctor who was watching their exchange with great interest.
“I know it isn’t easy for you but it’s not meant to be. Now, am I going to have to tie you to the bed for this next part?”
Lindy almost answered yes. Being bound and unable to free herself would absolve her of any responsibility for what was happening. If she was tethered to the bed, she could tell herself that she had not really consented to any of this but she knew, deep down, that it was too late for that. There was no backing out now, not if she had any hope of truly making amends for what she had done. She shook her head and allowed Jackson to settle her on the bed.
“Pull your feet up toward your bottom and let your knees fall to the sides.” The doctor gave Lindy an instruction she had heard before during more run of the mill medical exams, before shattering the illusion that this was just a simple clinical process by adding, “I want you as wide open as possible so we get a nice view of your sweet little pussy.”
Despite the feelings of trepidation that still lingered, Lindy did as she was told, adopting the intensely vulnerable position. The most intimate areas of her body, which she was now glad she kept shaved, were completely on display as she lay there with her legs spread wide and she knew that she would not be able to hide a thing. Her reward for obeying the command came in a nod of approval from Jackson who sat down on the bed next to her.
“Now, let’s see if we can get you nice and wet again,” the doctor said as Jackson moved his hand between Lindy’s legs. Running a finger along her slit, he explored between the plump, tender lips, mapping out every inch of the moist pink flesh within. As he found the sensitive bud of her clitoris, Lindy tensed and, without thinking, slapped her hand over his, to still his movements.
Shaking her head, the doctor clucked her tongue in annoyance.
“We don’t have time for these pointless displays of modesty,” she scolded. “I think you ought to tie her hands.”
A searing look from Jackson halted any protest Lindy might have made and she knew that she had blown her opportunity to show she could comply as he quickly unknotted the vibrant blue tie he was wearing and began to wrap it around her wrists. Then he pulled her arms up over her head and tied the other end of the long, thin strip of fabric around one of the iron bars in the bed frame, making sure she was completely secure.
Helpless to interfere in what would happen next, Lindy felt an unexpected shiver of arousal coursing through her. Jackson turned his attention back to her clitoris, flicking his finger gently over the swollen nub and making it throb wildly. As the first unmistakable waves of pleasure began to wash over her, he took the pulsating bud between his fingers and pinched hard, sending her screaming into orgasm.
“That was a beautiful climax, my dear. You’re very sensitive.” Dr. Gilbert grinned widely and Lindy basked in the praise as her mind slowly drifted back to earth. The other woman stood next to her and pressed her fingers against the side of Lindy’s neck, her head cocked in concentration as she checked her pulse. “And it certainly got your heart rate up.”
The doctor moved to the bottom of the bed and took a seat. Mortified as the other woman stared at her dripping wet pussy, Lindy snapped her legs shut. Immediately she was rewarded for her disobedience with a hard slap across the thigh. She barely had time to register the burning sensation in her flesh before the doctor took hold of her raised knees and parted her legs forcefully.
“Now, keep them wide apart or I will have Jackson hold them while I give that plump little clit of yours a thorough spanking.”
Panic flared in Lindy’s eyes and, knowing that she was not yet ready to face such a sensual ordeal, she did as she was told. Humiliating as this was, it might get a whole lot worse if she continued to allow her mind to overrule her body like this.
“Now, I just need to check that everything is alright internally.”
She pressed a hand firmly down on Lindy’s abdomen as she pushed first one, and then two long, slender fingers deep into her vagina. As Lindy flinched at the intimate invasion, Jackson moved unexpectedly to take her mouth with his. There was nothing tender about his kiss. It was an assertion of dominance that set every part of her ablaze. His tongue swept in and out of her mouth, matching the rhythm of the female fingers that probed inside her seeking, and finding, that magical spot on the wall of her soaking wet cunt. As the doctor pumped her fingers in and out of Lindy’s body, Jackson massaged her breasts, his thumb circling the pretty pink areola with a teasingly light touch.
It was all too much and yet not enough. Lindy writhed on the bed in a fit of helpless passion, whatever anxieties she might have felt about being touched so intimately by another woman shattering as she was hurled into the most intense orgasm she had ever experienced. Her hips bucked violently off the bed, her wrists straining in their bonds as she shrieked out her pleasure.
As she regained her awareness of the room around her, she saw the approving expressions on the faces of her two sensual tormentors and for a moment she basked in the glow of having passed a major test.
“Excellent responses,” Dr. Gilbert said. “And everything appears to be healthy. So now we just need to take your temperature.” She looked to Jackson now. “How do you want to do this?”
Already he was untying her from the bed. He unwound the tie from around her wrists and rubbed them gently to help her get the feeling back, confusing Lindy once more with his ability to be tender.
“On all fours.” It was an instruction as much as a response to the question.
“What?” Lindy sat forward, clasping her hands around her knees as she realized the sterile package the doctor was now opening contained an oversized rectal thermometer. “No, please, you can’t.”
“Anal virgin?” The doctor addressed Jackson rather than Lindy.
“Well, this is how we’re going to play it, Belinda,” the older woman told her in a stern voice that brooked no argument. “I have been asked to perform a thorough examination and that is precisely what I will do. I am sure Mr. Davies here intends to enjoy this lovely little bottom of yours regularly and I am going to make certain he will have no problems in doing so. If you do not cooperate, we will have no choice but to lie you on your back and hold your legs in a diaper position. Is that what you want?”
Lindy’s hesitation lasted only a second before she turned over onto her belly and raised herself up onto her hands and knees. It was a position that left her bottom completely exposed but she had no doubt it was less humiliating than the alternative. She tensed, half-expecting the instrument to be thrust straight into the puckered opening at any moment.
“So, have you ever had your ass fucked?” Jackson’s question sounded casual but she could hear the interest in his voice.
Lindy shook her head, painfully aware that the movement made her breasts sway temptingly beneath her. Never before had she put her body so blatantly on display.
“Sorry, I didn’t catch that.”
“No, I’ve never had my ass fucked.” The words sounded odd coming from her mouth. She was no prude, that much was becoming clearer with every passing moment but, being a teacher, she was always very careful about the language she used. “Nobody’s ever touched me there before.”
Jackson nodded, his eyes gleaming with the promise that he would soon rectify that and Lindy shuddered with a mixture of dread and delight. Anxiety over her conflicting emotions mounting, she blinked to keep tears from falling. She was doing well and didn’t want to wreck that now.
“Just relax, sweetheart,” Jackson said softly, his mouth close to her ear. “If you don’t, this is going to hurt.”
Did it mean something that he’d called her sweetheart? Clinging to the hope that it did, Lindy tried to let go of her fear. She had never experienced any kind of anal penetration before and although her cousin Abby spoke with real exuberance about having her husband fuck her that way, Lindy could not imagine how she could gain pleasure from it. But, she wanted to please Jackson and show him that she could be good.
She jerked in surprise as her butt cheeks were parted and a lubricated finger worked its way carefully inside her. There was something arousing about being touched by the gloved hands and Lindy sighed as her clit began to tingle once more. Dr. Gilbert was gentle as she probed the anal cavity, twisting her finger around as she checked for any abnormalities. It was an odd sensation but not unpleasant. In fact, Lindy was starting to think she’d been making a fuss about nothing. All that changed as a second finger was pushed into the tight little hole, causing her to blow out a sharp breath.
“Oh, fuck, it’s too much.” She tried to move forward, to escape this shameful intrusion into that forbidden part of her body but Jackson held her in place. “Please, I can’t take it.”
“You can and you will,” Jackson said sternly. “Very soon you’re going to accept my cock there and I can tell you it’s a great deal bigger than the good doctor’s fingers, so you’d better start getting used to the idea.”
As the fingers continued to move in and out, fucking her bottom hole with increasing vigor, Lindy found that she was, indeed, starting to become accustomed to this new and strange feeling. She could even feel the wetness pooling at the apex of her thighs.
Breaths coming in short pants now, Lindy pushed back shamelessly against the other woman’s hands, desperate for closer contact, trying to draw her fingers deeper inside. Before she could achieve any kind of satisfaction, Dr. Gilbert withdrew, leaving her bereft. The feeling of emptiness was not to last as, seconds later, the oversized thermometer was carefully inserted. Lindy moaned in pain or pleasure—she could no longer tell which—as it was pressed deeper inside her.
“Good girl. You’re doing great,” Jackson told her.
Breasts dangling beneath her, legs spread apart, and with a thick rod of plastic sticking out of her bottom, she imagined she made an obscenely erotic sight.
“Have you any idea how incredible you look right now?” Jackson continued. “Do you have any idea how hard it’s making me to see you like this?”
Knowing that she was affecting him so deeply thrilled Lindy, making her even more desperate for his touch. She longed to feel his hands on her, needed his expert fingers to work her clit until an orgasm burst from her but he just sat close to her on the bed, unmoving. After a few moments, the thermometer was pulled slowly out of her and Jackson ran his hand, almost affectionately, over her buttocks. She couldn’t help but groan in disappointment as it dawned on her that she was going to be left unfulfilled.
“Don’t be greedy now,” Jackson responded to her unwitting pout in a gently mocking tone. “You’ve had enough for one night. You can get into bed now.”
Recognizing that it was not merely a suggestion, Lindy scrambled to get under the covers.
“Temperature’s fine,” the doctor announced. “And everything seems to be in good working order. I’m very pleased with your responses. I believe you’ll do well, young lady.”
She took off the latex gloves she had worn throughout the whole process and tossed them into the wastebasket in the corner of the room. She picked up her bag from the table and headed for the door.
“It was a pleasure to meet you, Belinda.” Dr. Gilbert appeared to mean what she said. She looked to Jackson. “See you downstairs?”
“In a minute,” he confirmed as she left the room and then turned back to Lindy. “You did good, little one.” The praise seemed to be offered grudgingly, as though it did not come naturally to him. “Better than I expected.”
Lindy’s eyes glowed in response. “So what happens now?”
“Well, it’s two a.m.,” he checked the expensive-looking timepiece on his wrist, “and you need to be up early so what happens now is that you get some sleep. Tomorrow is going to be a busy day.”
He pulled the covers up around her, placed an unexpected kiss on her forehead, and got to his feet. Looking down at her, he grinned mischievously. “Oh, and Belinda, no touching. Any pleasure you experience while you are here will come from me. Is that understood?”
Lindy nodded but he was already walking from the room, clearly expecting that she would follow his edict. As the door shut behind him, she heard the locks clicking ominously into place and it suddenly occurred to her that she needed to use the bathroom. Closing her eyes, she buried her face in the thin pillow that had been provided for her and groaned. She did not want to use the chamber pot but there seemed to be little choice.
Struggling out from under the covers, she got up and reached under the bed and retrieved what was actually a very prettily decorated antique chamber pot. Sighing deeply, she dropped down into an inelegant squat and positioned the porcelain vessel beneath her. She felt ridiculous, like a child going to the potty and hoped that there was not a camera hidden somewhere in this room because the idea that Jackson might be watching was more than she could bear. Almost as though her thoughts had been heard, the lights abruptly went off and she found herself hunched down in the darkness.
“Well, that’s just great,” she complained out loud as the sudden lack of light threw her off balance. Quickly righting herself, she tried once more to relieve the pressure in her bladder but still nothing came. She tried to just relax and let her waters flow but her mind was racing too hard. Again, she let out a plaintive sigh. It was going to be a long night.
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