Sweet Gwendoline Ch. 09

The security guards weren't nearly as conflicted or curious as I was about my handler's orders. One of them just placed her foot between my thighs and nudged at my inner-thighs firmly until my knees were lewdly apart. I felt like my pubic lips were indecently on display.

Eventually my handler finished up her work on her computer and she stood up, towering over my kneeling, naked form.

"Gwendoline Schön," she said to me, and she said my name like it was an accusation, "You have been the source of a great deal of stress for some of the staff here."

I was caught totally by surprise at her accusation. I didn't have my watch with me, but I could've sworn I hadn't been at the Vineyard for more than an hour and I thought I had been very obedient and well-behaved during that entire time. I didn't think I had done anything wrong, however, I felt a sense of panic as she towered over me.

"I'm sorry, Mistress," I said as contritely as I could, "I didn't realize I'd done anything wrong."

There was an irrational part of my brain that wanted me to scream, "I'm a bad girl! Punish me! I deserve it," but I overrode that part of my brain, and waited to see what my handler said next.

The angry lines on her face smoothed out somewhat and she stood up straighter. She looked rather poised and self-assured after I apologized to her and then she frowned and said, "It normally takes about twenty days for a new applicant to become a member here. There's the official application. There are interviews. There's at least one physical examination, sometimes two. Photographs are taken. Medical records are obtained, and we sometimes have a private detective look into your past, just to make sure you're the right sort of person for membership, however, Ruth Taylor insisted that we rush your application and get it all approved in less than twenty-four hours."

I hadn't been told any of this previously. Yesterday I didn't even know that the Vineyard existed, and then suddenly Christina was driving me to their headquarters and introducing me to their staff.

"I had no idea, Mistress," I told my handler, timidly, "I didn't even know that the Vineyard existed until about an hour ago."

My handler walked out from behind her desk. I was kneeling and she was standing, so I didn't get a good look at her, except for her legs. She had nice legs. I'm guessing that she was a dancer at some point, as her legs looked incredible.

"You shall address me as Doctor Riemen," she said to me, coldly, "I have a doctorate in psychology from Brynn Mawr college, and I expect you to acknowledge that accomplishment every time you address me. Obtaining a doctorate isn't easy. Only two of the people who work here have one. If you ever address me without acknowledging my accomplishment, you will be punished. Do you understand?"

My mind was awash with personality conflicts. My handler had a grudge against somebody, perhaps a large number of somebodies. I didn't know the whole story behind her hostilities, but she was angry at somebody. I decided that I would bring up her doctorate whenever I could, and always address her as Doctor Riemen. It seemed to be a way to get on her good side.

"I'm sorry, Doctor Riemen," I said, timidly, "I understand."

Then she squatted down in front of me, pinched one of my nipples painfully and whispered, "I am very good at my job, dear, however, Ruth Taylor seems to take great joy in making my job more difficult. I cannot do anything about that, however, if you make my job more difficult, I can punish you in ways that you will absolutely hate. Do you understand what I am saying, Gwendoline?"

The pain in my maltreated nipple meant that I was very focused on Doctor Riemen's words. I wanted the pain to stop, and it wouldn't stop until Doctor Riemen felt that her words had had the proper effect on me. I felt a strong inclination to make certain that I did exactly what Doctor Riemen wanted me to do.

"I understand, Doctor Riemen," I said, my voice sounding strained as she painfully twisted my tender, pink nub, "I won't do anything to make your job more difficult."

"Splendid, Dear," Doctor Riemen said, finally releasing my poor, abused nipple, "I'm delighted to hear it. I'm so glad we understand each other."

Doctor Riemen rose to her full height and took a step back. Being naked and kneeling, while she was fully clothed and towering above me really emphasized the stark difference between her status and mine. I'm pretty certain that was deliberate.

"Earlier I addressed you as Gwendoline," Doctor Riemen said, "It's your name and you respond to it, however, you are also Inmate number 1101. If I address you as Inmate Number 1101 and you don't immediately respond, you will be punished. Security guards, office staff, medical staff and other Vineyard employees may also address you as Inmate 1101. If that happens, you had better respond. Failure to respond will be viewed as a lack of respect on your part, and will merit punishment."

For a moment my heart beat too fast, and I knew fear, a delicious fear. I had an inmate number? I could be punished for forgetting what it was? This place was so cold and unforgiving. It was exactly the sort of place that an evil stepmother would send a naked step-daughter to humble her, punish her and break her spirit.

Doctor Riemen continued and said, "You have two overseers, Ruth Taylor and her niece. It's highly unusual for an inmate to have two overseers. It means sharing ownership and authority over you. Most dominants don't like to share, however, Ruth Taylor and her niece seem to have a very unconventional relationship."

There was a long pause, and I responded, "Yes, Doctor Riemen," as it seemed she was waiting for some sort of verbal response from me.

"Ruth Taylor has paid for your membership here," Doctor Riemen informed me, "However; as your handler; I have more authority over you than she does. While you are here, I decide what sort of training you will receive. I decide who you will interact with. I will control if, when and how you will have orgasms. I will decide when and how you will be punished. As your handler, I will control your every move whenever you're here."

Her words were so cold and authoritarian. I felt a soft, wet pulse between my widespread legs at those words. Ever since I was a young girl I'd dreamed of having a cold, authoritarian woman to punish me, chastise me, subjugate me, humiliate me and keep me naked. A feverish heat took hold of me as Doctor Riemen seemed to be telling me that she would become all of those things.

"Now, both Ruth Taylor and her niece have told me that you work as a stripper, and that bruises and long-lasting marks on your skin would cause you to miss work. This means that punishing you with bullwhips, dogwhips, buggy whips, snake whips and riding crops cannot be permitted. If I were new at my job, this might present a problem, however, I have worked at the Vineyard for seven years, and I know how to punish naked submissives without leaving any lasting marks. I merely must be more creative than an amateur dominant. You may not like some of the things that I do to you, however, you will survive."

"Yes, Doctor Riemen," I replied timidly when she paused and looked intently at me, seeming to want a response.

"Now, you will be given a safe word," Doctor Riemen informed me, "The safe word is not to be used lightly. I'm very good at my job and generally know when a slave is reaching his or her limits, however, if there is a true emergency you can use your safe word, and I shall immediately cease punishing you. We have medical staff on retainer and they can be summoned if you are truly injured."

"Yes, Doctor Riemen," I said somewhat hesitantly. Christina and I had never used safe words. I had always surrendered to her completely and trusted that she would never do any permanent damage to me.

"Your safe word will be 'elaborate'," Doctor Riemen informed me, "However, I advise you to use it sparingly. Inmates that use their safe word repeatedly don't last long here. They're considered to be a nuisance and sooner or later their membership is revoked and they're banned from ever returning. Ruth Taylor paid a lot of money to get you in here. She would be quite irate if you were to be thrown out for being too delicate and panicky."

No doubt both Christina and her Aunt Ruth would be quite upset if I used my safe word too much. Doctor Riemen would be upset too, I could tell. I was sure she had a degree of contempt for submissives that were soft and couldn't handle pain and discipline. I didn't want to disappoint any of these women, so I resolved not to use my safe word, unless a real emergency came along.

There was a knock at the door and Doctor Riemen's assistant got up and opened the door. Christina and her Aunt Ruth were admitted into the office once the door was open.

"Miss Ward, Miss Taylor," Doctor Riemen greeted my mistresses. Her voice was flat and utterly lacking in emotion.

"Beverly," Ruth responded, "How is our naked slave-girl coming along?"

I saw Doctor Riemen's shoulders tense slightly at Ruth's words. I think perhaps she felt slighted that Aunt Ruth addressed her by her first name instead of by her title, however, she seemed to quickly shrug it off.

"I had just finished giving Gwendoline her orientation speech," Doctor Riemen replied, stiffly, "She appears to be taking her role seriously, however, it's too early to make a proper evaluation of all of her strengths and weaknesses."

"Well, don't let me stop you from evaluating her," Aunt Ruth said in a warm and charming tone of voice, "Just pretend that my niece and I aren't even here. We'll just blend into the woodwork, while you work your magic with her."

Christina and her Aunt Ruth were seated in chairs near Doctor Riemen's desk.

"Alright, Gwendoline," Doctor Riemen said, looking intently into my eyes, "These guards are going to give you a body-cavity search. I expect you to give them your complete cooperation and do everything they say. If you're uncooperative, or slow to obey, I will be very disappointed in you."

The way Doctor Riemen pronounced the word "disappointed", she made it sound like the worst obscenity she could think of. I was certain painful punishments would follow if I disappointed Doctor Riemen, so I resolved to quickly and completely comply with all instructions that the security guards gave me.

My wrists were unlocked from their stainless-steel bondage and one of the uniformed security guards snapped an order at me, "Stand at attention!"

I had naturally assumed that her order had meant that I should stand at the military attention position. As a result, I hastily rose to my feet and stood upright and rigid with my chin up, feet together, hands at my sides, chest out, shoulders back and my stomach sucked in.

"No!" the security guard admonished me and smacked both of my breasts with her unforgiving hand, "When an agent of the Vineyard tells you to stand at attention, you are to stand with hands at the back of your neck and spread your legs!"

The domineering woman's voice was harsh and brooked no disagreement. Hastily my hands flew to the back of my neck and I spread my legs about twenty inches apart. I kept my chin raised up and tried not to make eye contact with the woman who had just spanked my breasts. I had no reason to know what she had meant by "stand at attention" but I felt guilty for getting it wrong anyway.

"Now open your mouth wide and tilt your head back," she added, "I'm going to start by inspecting your mouth."

I opened my mouth painfully wide, as if I were at the dentist and I felt fingers in my mouth, pressing down on my tongue, sliding methodically across my teeth and gums and finally her fingers probed mercilessly deep. I struggled to relax my throat and keep from gagging, but it was a difficult feat. I felt the tips of her demanding fingers fill my throat, my eyes welled up with tears, but I somehow managed not to gag or bite on the woman's fingers.

My jaw ached and I gasped and panted after she removed her fingers from my mouth. The security guard then told Doctor Riemen that my mouth was clean of any contraband, and then I was ordered to go stand against the north wall, place my hands flat against the wall and spread my legs.

I had no idea which wall was the north wall and got my naked buttocks smacked when I ended up standing against the east wall instead. When I made it to the north wall, I nervously placed my hands flat against it, staring at the plain, white surface and spreading my legs.

Hands up higher," "the guard snapped at me, "Legs farther apart and stick your butt out further, towards me!"

I obeyed her terse commands heard a sharp sound behind me as the security guard snapped on a latex glove. I felt a thrilling pulse of fear and anticipation as I guessed what was coming next. The uniformed woman seemed so tall and powerful, standing close behind me as two of her fingers entered my wet vagina, probed, explored and made me squirm.

"Hold still," the stern woman barked as her fingers impaled my sex and caused my loins to resonate with wave after wave of agonizing desire. My breathing became ragged and labored, but I did my best not to squirm or tremble as she put her fingers up me, way up, unnaturally deep.

The cold, pitiless woman removed her demanding fingers from my vagina and there was a brief interval to recover while she removed the glove with my vaginal secretions and then she snapped on a fresh one.

I felt a glob of something cold and wet smeared into the furrow between my buttocks and then I felt a finger pushing against the soft pink flesh of my exposed anus. The finger wiggled and pushed, forcing my tight barrier of my sphincter to open. Then a second finger pushed in and brutally forced my anus to open wider.

I gasped and felt a sense of panic. My legs trembled as the fingers twisted around inside of me. It wasn't excruciatingly painful to have my anus forced open by this unfeeling woman, however, it filled me with an appalling sense of helplessness for her fingers to impale my tight, pink little anus. It was so utterly different from being vaginally penetrated. Something about this woman stabbing her fingers into my anal orifice seemed so much more humiliating and harmful than when she thrust her fingers into my vagina.

My eyes welled up with tears and I vainly attempted to stifle a whimper. The trembling in my legs became worse and then I heard Doctor Riemen say, "What's the matter, Gwendoline? Why all those lovely tears?"

My throat was tight and I couldn't seem to answer at first. The fingers impaling my asshole left me with an appalling sense of helplessness that I hadn't anticipated.

"It just feels so wrong," I attempted to explain to Doctor Riemen, "Nobody has ever put a-anything in my anus before! It feels so unnatural! It makes me feel so terribly helpless and violated!!"

Tears were now flowing unreservedly down my face. I had no idea that being anally penetrated would be so traumatic for me, however, I felt on the verge of a panic attack, this was so distressing. I desperately wanted the female security guard to stop violating my virgin asshole.

"Fascinating," Doctor Riemen said, her tone of voice utterly lacing in concern for my distress, "It's usually the male submissives that agonize the most over having their pretty little assholes pried open. The females typically handle it with less distress than you're currently exhibiting. Do you wish to use your safe word, Dear?"

I squeezed my eyes shut tightly and gritted my teeth. I briefly considered the possibility of shouting out "elaborate" and ending this violation of my tiny, virgin asshole, however, that would mean showing weakness in front of Doctor Riemen, Christina and her Aunt Ruth. I wanted all three of these women to be proud of me, and using my safe word within fifteen minutes of being given it, would be humiliating.

I swallowed hard and said, "No, Doctor Riemen."

"Very good, Dear," Doctor Riemen said, "I'm proud of you."

Then Doctor Riemen snapped on a latex glove and disappeared behind me and told the security guard to step away from me.

I felt my sphincter muscle close as the security guard's fingers withdrew from my anus, and then Doctor Riemen said, "Now keep those legs wide, Dear. You and I are going to have a little chat while my fingers are inside of you."

More cold lubricant was smeared onto my anus and then I felt Doctor Riemen's fingers pushing into me, prying me open. I groaned as she stretched open my asshole and then she said, "Now Gwendoline, I am going to ask you some questions, and you are going to be very honest with all of your answers."