Founded Sep 19, 2012
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smooth sissy lover
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The voice at the other end of the phone brought a smile to my face. Very few knew my secret, it wasn’t something that came up in polite conversation. Luckily one of those who did know favored a facet of the scene which drew me in like a moth to a flame. As I answered the phone, I heard Lisa say, “Hey, I think I might have something that you would find of interest. Mind if I come over tonight and discuss it with you?”

I was always happy to see Lisa. She was a curvaceous blonde, with sparkling blue eyes who embraced life to the fullest. She came in the door, a wide smile on her face as she took my hand, leading me to the couch where we sat down.

“Mistress Candy asked me about you today.” I couldn’t help it, my eyes opening wide as she laughed saying, “She’s thinking about throwing a party next weekend and wants some specialized toys for her guests. She asked me if I might know anyone and your name happened to come up.”

Lisa’s Mistress was very well known amongst the darker side of BDSM. Her parties were the story of legend but she had never shown any interest in someone like me to my knowledge. I tried to keep my voice level as I asked, “May I ask what you spoke of Lisa?”

I could see the look in her eyes, the mischievousness, as she toyed with me saying, “I’m not sure my Mistress would like me divulging our conversations with a slave such as yourself, hun. I’m not sure that would be in good form.” The look on my face must have resembled a puppy who had been swatted with a rolled up newspaper and she couldn’t help but laugh when she said, “I told her you’re a CD, a submissive sissy maid who enjoys her role very much.”

I couldn’t help it, I felt myself blushing like a schoolgirl as she grinned, my eyes instinctively lowering. I almost jumped out of my seat when the phone rang for a second time that night. Lisa looked at me innocently saying, “Now, I wonder who that could be?” My eyes must have grown as round as saucers. I was frozen to the spot knowing she was up to something. She shook her head, getting up and answered it. “Samuels residence, who may I say is calling?”

It was like watching a light switch being turned on, her eyes immediately cast downward, her voice turning softer saying “Yes Mistress, he, I mean she is here”, as she handed me the phone and I picked it up like it might possibly bite me.

“Hello?” My voice actually quivering when I heard an unfamiliar voice on the other end begin to speak.

“I believe you know to whom you are speaking gurl, so I suggest that you not only mind your manners but remember your place.” It didn’t sound like a reply was necessary as she continued, “I will be holding a get together of quite a few people who will be joining me for an evening of, shall we say, debauchery a week from tonight. The girl who is there with you now told me of you, and on her word I am inviting you to come and serve as a maid for that evening. If what she has told me about you is found to be untrue, the circumstances shall prove to be costly not only to you to, but to her as well. Do I make myself clear?”

I tried to speak, I truly did but the words wouldn’t pass my lips. “The proper response is either Yes Miss or Yes M’lady. You do not wear my collar as that little slut sitting next to you does. You do not have the right to call me Mistress…yet.” With that the phone went dead and I turned to Lisa, a look of horror tinged with fear in my eyes.

As funny as it sounds, I put my head between my legs, finding it very difficult to breath. I felt a cold compress on my neck. Lisa was standing over me, her voice no longer as playful as before. “What did she say to you?”

I managed to gain my composure and repeated the conversation. Lisa’s smile turned into a nervous frown as she said, “That means if you fail I fail and we both will be…” the answer hanging in the air when I finally found my voice.

“Perhaps it would be best if I were to call her, to thank her for the opportunity and say that I’m not able to attend?”

“No! You do that and not only will you never have a chance like this again, I’ll find myself down in the catacombs.” She paused, her face turning pale. “I went there once, I never want to go there again.” Lisa was visibly shaking, my mind running wild with the thought of what she had once experienced.

She looked at me, her voice a bit urgent as she said, “Do you trust me?” I must have looked confused as she repeated “Do you trust me Jonathan to do what I think is best for you?” I nodded and watched as she picked up the phone, dialing a number before walking into the next room. I could only hear a muted conversation and wondered what precisely was taking place.

When she returned, she was pacing, her eyes deep in thought. I went into the kitchen to open a bottle of wine. As I began to pour two glasses I heard a knock on the door and heard Lisa calling out she would get it. Lisa’s question still on my mind I went to see who it was. To my surprise a dark haired beauty walked in, hand in hand with my blonde friend. “Jessica this is Jonathan, my friend I spoke to you about on the phone.”

I held my hand out to the green eyed woman but she simply stood there, looking me over, her eyes taking me in as my hand slowly fell. I couldn’t help it, my eyes did the same. With that she walked over, moving in close, her mouth directly next to my ear, her breath warm and I shivered as she said, “I am a switch. Do you know what that means?” I nodded. “You are a sissy, correct?”

I looked at Lisa, knowing she had to have told my secret. Jessica took me by the throat, squeezing hard, getting my attention, her voice cold and strong. “When a better asks you a question you will answer, now answer me boy.”

She let go of my throat, my voice choking, sputtering forth, “Yes Miss.”

With that I got a smile, Jessica lifting my chin saying softly, “That’s what you need to do when a dominant asks you a question. You answer quickly, you speak succinctly and most importantly, you speak with respect.”

“Yes Miss.“ I turned with shaking hands offering the two wine glasses to each of the ladies. Jessica smiling at Lisa, shaking her head slowly.

“We have a lot of work to do.” Jessica handed her glass to Lisa, motioning toward the living room as the blonde obeyed immediately and without a word spoken. Then, the stranger in my home once again turned her attention to me.

“Lisa would not have called me if this were just a game. From what I’ve heard you’ve been simply playing to this point at being what you desire to be. This is real. You have to show me you know what you are doing, why you are doing it, what the consequences are.”

I felt my face flush with anger but she simply ignored me saying, “You have a choice. You can do one of three things. You can refuse the offer you’ve been given and in doing so doom yourself and poor Lisa will suffer dearly if you do so. Secondly you can present yourself as you currently are, fail miserably and once again Lisa will suffer though I’m sure you will feel Madame Candy’s wrath as well.”

With that she moved in close, standing directly in front of me, her eyes staring deeply into mine as I stood with fists clenched. “Or third, you can accept the fact that Lisa here obviously cares about you and wants you to succeed. She knows that I’m the one person who, given only one weeks time, can turn you into that which is required for the party and”, she paused, lowering her voice, “what you desire, most of all.”

I closed my eyes, my body shaking. “It’s okay to be who you are Jonathan“, she whispered, “the shame is in not being true to yourself. I can help you but you have to ask, you have to want this. Not Lisa, not me, you…have to want this.”

Sighing, I opened my eyes, looking at the dark haired woman whose face was kind, not judgmental, simply accepting. I fought to keep my voice straight, “Will you help me Jessica, please?”

The smile on her face lit up the room as she said in a mock stern voice, “That’s Mistress Jessica to you sissy”, as I lowered my eyes. She broke out in laughter and I couldn’t help but smile. She took my hand in hers, pulling me into the living room where Lisa was waiting.

“Okay, as I said, we have a lot of work ahead of us. Now you need to show Lisa and I what you have.” I must have blushed a bright shade of red because she said “No Jonathan, what you have to wear.” I ran up the stairs, once again their laughter following me and I wondered what I had gotten myself into.

It was a week later that I found myself in a car with the two women, sandwiched between them like a prisoner on the way to his, I guess I should say “her” execution. Both of them were dressed beautifully, though scantily as their Mistress had demanded of them. As for me, I was dressed as I normally did, a bit confused but neither girl was willing to discuss the matter, having said it was out of their hands.

We arrived early. Mistress Candy had issued a command that all of her slaves must pass muster by appearing before her. As we got out of the car, I garnered a few curious looks, dressed in a simple shirt and slacks, certainly out of style based on the others I saw. I felt Jessica take my left hand, Lisa my right pulling me up the stairs. Lisa whispered in my ear, “Take a deep breath Jonathan. Relax and remember your lessons. Jessica has trained you well, you’ll be fine.”

I wish I had her confidence. I certainly didn’t feel like I would be fine, disaster seemed to be right around the corner as we stepped into the main entryway. Before us was a long staircase. At the top, looking down upon us was the grand lady herself. Once we were all in our place, she began descending towards us we all fell to our knees. It took every amount of courage I had not to get up and run. Instead, I remembered what I had been told. Their Mistress stopped before us her eyes on me as I made sure my eyes were cast downward. ” Stand up, boy!”

“What is your name?”

I kept my voice calm, but spoke softly saying “My name is Jonathan, Miss.”

I stood there, the seconds passing when I heard “Present yourself to me, boy.”

This was my first real test. I kneeled as fluidly as I could, certainly not anywhere near the style or grace of the women who were on each side of me but I allowed my knees to slightly part, my hands palm down on my thighs, my back remaining straight and as always keeping my eyes to the ground.

I was rewarded with a single word, “Adequate.“ I remembered that I had been told by Jessica that any compliment from the lips of Mistress Candy was one to be treasured.

“Lisa, Jessica, rise, now.” The women did so, still maintaining their submissive poses as she said, “Both of you, look at me.” The two stunning creatures obeyed, keeping their gaze respectful as I knelt, listening. “Lisa, you told me that this individual has a desire, one that you assured me could be beneficial to my service this night. Do you understand the consequences of failure whether by you or by your charge?”

“Yes Mistress Candy, I do.”

She nodded before turning her attention to the dark haired woman, “Jessica, I have heard you have been tutoring this boy in the ways of service. Are you aware of the possible ramifications if the service is found unacceptable? If my guests are displeased in anyway? Two will not suffer, the number will be three.”

For Jessica, she had been brought into this challenge by her friend. By choosing to help us she had put herself into a very difficult situation, the literal rock and a hard place. But all I heard was, “Yes Mistress Candy, I am aware of all of that and I gladly welcome the challenge.” My heart swelled and for the first time I felt confident. Both my friend and this relative stranger believed in me and I was beginning to believe in myself.

I didn’t see it, the flash in the red haired woman’s eyes and the smile that played on her lips as she stepped closer to Jessica, her eyes locked into hers. The woman who had worked so diligently with me didn’t turn away, returning the stare as I heard the Mistress say, “One day that switch side of yours is going to come out at a very inappropriate time and you will pay dearly child.” With that Jessica finally let her eyes slowly fall.

“Rise boy.” I did so as the three of us stood before her when she began to speak. “You have two hours to make this happen. By instructing you that he was to be brought here precisely as you have done I have not made it easy for you. Now, you will go to the third guestroom on the right. I have left another set of instructions for my two slaves based on the information you have provided me with. Two hours from now we will see if you three will sing…or scream. You are dismissed.” With that, she turned her back to us, walking away.

We stood still until she disappeared from view and then you would have thought there was a sale at Bloomindales as we scampered up the stairs, moving quickly toward our destination. When Jessica opened the door, all three of us saw the dozens of boxes and items on the bed, and a single envelope waiting to be opened. I stayed back, letting the two women move to open it. Holding it between them they began to read.

“I’m sure you know how much I enjoy a challenge, especially when it’s two of my girls who are put to the test. If you’ve gotten this far I admire the faith you have in your student but I’m not going to make it easy for you. You will say nothing of this to him, not a word until you are finished and I come to the room. I have purchased everything you will need for him, you will find it all in the boxes and in the bath. I do not want a simple maid, I want a submissive sissy fetish maid, with appropriate makeup and I promise based on the clothing I have had made specifically for this event, your “gurl” will look the part. The clock…is ticking.”

The two women looked at one another and it was like watching a finely trained pair of soldiers as Jessica said to Lisa, “I’ll take the boxes, you take the bathroom. Jonathan, strip. Now!”

It was obvious the dominant had returned and I did as I was instructed, hearing Lisa call out, “Get your ass in here Jonathan, now!” I almost tripped over a pants leg, sprawling to the floor as I looked into the bathroom, the blonde holding up a pink bottle as I pulled my final bit of clothing off and she said, “Arms out, legs wide” and I obeyed as it all began.

It can only be described as a blur, being moved from one activity to the next. Both women shushing me every time I tried to ask a question. They simply shook their heads and put their fingers to their lips to show they only needed my silence. I finally accepted the inevitable. Strings were tugged, makeup applied, hair styled as the minutes passed, both women intent on their task. We all jumped when there was a knock on the door and a voice announced, “Mistress will be joining you in five minutes.”

My two hand maidens used every second of it, not even allowing me a glance of myself,, there was no time. Soon we heard the sound of heels approaching and both women grabbed me by the hand, pulling me to my feet as I balanced precariously on the heels of the shoes Madame Candy had purchased. The ones I had practiced in were nothing like what adorned my feet now. Both Jessica and Lisa barely got to their knees in time, their project standing between them as the door opened. All three of us held our breaths.

I felt her presence and inhaled her scent. “What is your name gurl?”

Keeping in mind how Jessica had taught me, my voice softened as I replied, “My name is Gabrielle Miss.”

A second or two passing, “Look at me Gabrielle.”

I slowly lifted my gaze as I saw what I swore was a woman trying to suppress a smile as she said, “Have you seen yourself in the mirror gurl?

“No Miss, I was instructed that honor of bestowing that gift was allowed only by you.”

“As it should be. Close your eyes Gabrielle.” She took me by the shoulders, walking slowly. I took careful steps, the stiletto’s on my feet locked on, insuring they would not come off until the time was appropriate. She led me across the room to the mirror, her hands still on my shoulders when she said, “You may open your eyes gurl.”

I did so and for a brief moment I thought I was looking at a picture, not into a mirror. The woman whose reflection I saw had an hourglass waist, courtesy of the heavily boned corset I wore. The maids outfit had been specially made, patent leather and lace, the skirt, petticoat and ruffled panties all easily seen. The stockings allowed quite an expanse of smooth, white alabaster skin to show above them. Black lace fingerless gloves, a matching lace choker with the single initial C on it. I was not collared but marked for at least this night.

My makeup for my eyes had been done in smoky, almost gothic like colors of grey, black and purple and my lips were colored a matching purple, outlined in black. I saw the sparkle in the woman’s eyes as she stood behind me, her hands roaming over the material as I blushed. She laughed saying, “Delightful, you are delightful little one.”

“Lisa, Jessica come to me.” Both girls rose, moving quickly as I heard her say, “For you there are three challenges you have to meet for my approval. You have successfully passed the first one. I would never have known this…this…” her head shaking in amazement when I saw the look in Jessica’s eyes and I took a deep breath.

My voice soft, almost a whisper, “Miss, may I please have permission to speak?” It was a calculated move, one we had discussed but I felt it was appropriate and luckily I received a nod as I tried to turn as elegantly as I could, moving smoothly to kneel before her, presenting myself before speaking again.

“I wish to express my thanks to you for all of the wonderful gifts you have bestowed upon me this evening. You have honored me by allowing me this chance. I pray in turn, I honor you this night, in my actions, in my words and in my service.” At this point as I bent forward and placed a gentle kiss on each of her heels, making sure not to leave a smudge.

For a moment there was nothing but silence and I feared my actions had been a breach of protocol but instead I heard her laughter ring out, as she turned to my two companions saying, “You two are just full of surprises.” They both smiled as well, though keeping their eyes lowered as she took her leave, her parting words, “To the kitchen with this wench, her second challenge awaits her there.”

After she left, I felt both hands reach down, helping me to my feet. I must have surprised them both when I pulled them in close, my voice visibly trembling as I said, “I thanked her but in reality, I was thanking you, both of you. Please, please know that.” I was rewarded with hugs as well, Lisa with her brilliant smile and Jessica looking like she was the proud mother of the prom queen.

It was Jessica who spoke saying, “You did beautifully Gabrielle, you handled yourself with grace and presence, I could not have been prouder of you.” I must have blushed again as Lisa giggled and Jessica just rolled her eyes before saying, “Just remember, Mistress is well known for her “challenges” and we’ve only completed the first one. We still have two chances remaining. Let’s see what’s in the kitchen.”

With that we moved to the door at the back of the room, a lift taking us down to the kitchen. What we saw surprised us all. Everyone in the room was male, all with their skins glistening, oiled down, bowties and nothing else. All of them were servers and it dawned on me that I was the only maid.

One of the men walked up saying, “You must be Gabrielle” as he bowed, presenting me with an envelope with the single initial G on it. I shyly smiled at him as I opened up the envelope, two blue pills inside, a single envelope saying, “You will take these without question and you will await the sound of the bell. At that time you will enter the hall alone and bring me the glass that I will use to propose a toast to start the festivities.”

I showed the note to the two girls who read it, shaking their heads, knowing my presentation would be tested and they would not be allowed near for support or to assist. I walked over to the sink, poured a flute of champagne down the drain, filling it with water, knowing I needed a clear head. I quickly took the two pills and waited. It didn’t take long. The sound of the bell rang out and I tried not to freeze. The tray was presented to me, the door opened and I walked out of the kitchen and into the hall.

The word she had used was debauchery and it was not a word she had been used lightly. The people who milled about were in various stages of dress and in some cases undress. There was leather, there was lace. There were Dominants and submissives. There was literally something for everyone but it was the lady who stood in the middle of the room, ringing the bell that drew everyone’s attention. I strode toward her, hearing, “Ah, here comes my new toy with my libation.”

I heard soft murmurs and whispers as I remembered my training, going smoothly to my knees, holding the glass up high, making sure though I kept my voice as feminine as I possibly could while being insured it was heard. “I pray this offering is as pleasing to your palate as my service is to your eyes Miss.” I held the drink high while kneeling, my eyes lowered. She took it, taking a sip when I heard.

“Rise little one.” I did so, keeping my eyes cast downward as she announced, “This is this dear gurl’s coming out party. I present to you…Gabrielle.” I felt the flush rise to my face, once again simply me being me, her laughter ringing out as she leaned in close, her voice in my ear saying, “You will follow behind me and then you will kneel beside me after I have sat.” With that she turned and I followed like an obedient pet, waiting on her to rest on her throne, kneeling on her right side, presenting myself, my eyes as always remaining to the floor when she announced, “Let the festivities begin!”

People then began to come forth, greeting their hostess as I would hear snippets of conversations, comments made, some of them causing me to blush anew. Out of the corner of my eye I saw that Lisa and Jessica had been brought into the mix and it took all I had not to look their way and smile. Instead I remained in place, feeling the hand of their Mistress every once in awhile reach down, stroking my hair, touching my face while I made sure to remain still, accepting her touch as a gift she had bestowed upon me.

It was quite awhile later when I heard, “Gabrielle, look at me.” I raised my eyes, seeing the red haired beauty smile, her voice soft so that only I could hear her as she said, “If someone would have told me that such a transformation was possible I would have laughed at them. But I must admit, you and your friends have surprised me.” I didn’t hear a question, so I knew a response wasn’t necessary though I could not help but smile at the woman, the sincerity in her voice telling me that the words she spoke were true.

“The second challenge was met successfully. You served as well as many that have been in my care for more years than I can count. Now, the final challenge awaits and for it, we must reunite you with the two who have made this all possible for me and for you as well. You will rise, you will curtsey to me and you will join them. There is a final envelope awaiting the three of you which has just been delivered. Follow the instructions to the letter and this night will end well…for all of us.”

I had questions but I knew it would be useless to ask and it certainly would have been inappropriate. Instead, I rose as gracefully as I could, curtsied to the Lady and walked over to the staircase where Lisa and Jessica were waiting. Both of their faces showed a bit of confusion, Lisa holding the envelope that her Mistress had spoke of, whispering that she had been instructed that she was to be the only one to read it and that we should follow her lead or else the challenge would be considered a failure.

All three of us looked over at the red haired woman who sat regally, raising her glass our way. Lisa took a few steps up the staircase, opened the letter and began reading it. Both Jessica and I saw her face turn pale as her eyes opened wide, her fingers trembling causing the paper to flutter to the floor. Jessica started to speak but Lisa shook her head, her eyes pleading with her to remain quiet. The dark haired beauty curbed her tongue as we saw four men pull in a large, wrought iron four poster bed.

Once again you could hear the sound of the guests words slowly turn into quiet murmurs, wondering what might be about to transpire. I felt Lisa behind me, her voice quivering, below a whisper saying, “Trust me?” I didn’t allow my head to move, nor my lips to part as I felt her hand take mine, leading me out onto the floor. She tried to smile at me as she took me to the bed, her hand directing me to lie down. I did so carefully, moving so that my skirt remained in place. Two Madame Candy’s slaves attached shackles to my wrists, pulling them to the top two corners of the bed, the other two slaves shackled my ankles together.

With that Lisa turned, walking over to Jessica whose hand she took, my dark haired Trainer trying to keep her face neutral but I knew she was as lost as I was. She was brought out onto the floor, a soft gasp escaping her lips as a blindfold was placed over her eyes and then her hands were bound behind her as her scant costume was ripped from her body.

Lisa placed her hand between her companion’s legs. Another gasp, then a moan, her arousal already intense. It was then that her Mistress’s voice sounded out. “There is something you should all know about…Gabrielle.” I don’t know why but I knew what was coming, and I was afraid for Jessica it would prove to be a difficult, shall we say, “pill” to swallow.

She was forcibly lifted up, her legs forced apart. Lisa reached between my legs, the blue pills having worked their magic, my “clit” hard, swollen as I heard the level of conversation, the uproar begin as she was literally impaled on me. Her head snapped back as I filled her sex, mewling like a kitten as her body grew accustomed to the intrusion.

It was then that I saw two of the men advance upon Lisa, her eyes lowering as they blindfolded her. They bound her hands like her friends, her clothing soon lost as well as they lifted her over my face, forcing her to straddle me. I drank in her heavenly essence.

None of us was able to see as the two men took three sets of clamps, attaching them quickly to both of their nipples, their clits and most cruelly to each other. Whimpers and moans filled my ears as their bodies pulled against the torment, only tightening the clamps even more. Once we were set to her satisfaction Mistress announced, “Now, let the fun begin.“ She flipped a switch, the electrical current soaring through the silver chains and clamps, the two girls screaming as they began to frantically gyrate.

I was trying desperately to breath with Lisa’s sex pressed directly up against my mouth and nose. I feverishly began to try and give her pleasure to go along with the pain her body was enduring. I could feel Jessica moving up and down, seeking the same, knowing the drug that was in my body would insure the torment would not be short lived. Our dance was a macabre one, all of us puppets in the play that their Mistress had orchestrated and if we could have seen her, we would have seen the wicked smile on her face.

I felt it first. Jessica’s body gave in to the relentless desire which was coursing through her body, her scream animal like as her orgasm washed over her. It was only seconds later that I was given a choice to either drink or drown as Lisa joined her. Grinding down on my face, her delicious nectar flowing like a waterfall as these two amazing women provided those in attendance with quite a show, though it was not anywhere close to being over.

Screams of ecstasy were soon filled with cries of agony as one felt the flogger, the other the crop, their bodies being whipped harshly. The two men had been instructed that they would find themselves on the other end of those painful implements unless they forced the two helpless women to strain against their bonds, against the clamps, against their bodies even more. Both Lisa and Jessica would ride through one wave of an orgasm when another would begin and those in attendance watched in awe of the sexual frenzy on display before them.

Time lost all meaning, for all three of us as we were helpless pawns in the game, the crowning achievement to their wicked tormenters gala. Finally exhaustion took hold of the two women, their bodies slowly coming to a halt, their movements sluggish even as the lashes would fall almost unfeeling, their minds and bodies shutting down.

Mistress Candy signaled enough, switching off the current and the two men dropped their weapons. Our hostess strode onto the floor, first walking up to my dark haired Trainer, pulling the blindfold from her eyes. Eyes which had glazed over, the pain having taken her to places she had never been to before. “I told you that your switch tendencies would get you in trouble one day my dear”, as Jessica’s hands were freed, her body pulled over to rest pressed up against me.

From there she moved down to Lisa, the blindfold removed, the girls eyes bright, almost shining as Mistress smiled, knowing that Lisa was a pain slut and the gift she had been given was the greatest her owner could ever bestow. Her voice cracked as she whispered, “Thank you Mistress Candy, I am honored“, as her red haired owner put a finger to her lips, smiling at her as she too was freed, the two women now draped over me.

I felt a hand caress my cheek, my eyes looking up to see the woman who had made all this possible, the smile on her lips as she said, “Well, well Gabrielle, whatever shall you do for a encore little one?” I couldn’t help it, I did what I always did, I blushed as she laughed heartily and I wondered if this were the end…or simply the beginning.



Thank you for reading my tale. Please if you will take a minute to vote and possibly comment. I grow as a writer thanks to the encouragement and yes, even in the criticism I receive sometimes. Thanks again.




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  •  PansyAncelina: 

    If you "grow as a writer" then perhaps it would be best if you were encaged in a chastity device before you next put pen to paper (maybe that should be "put gloved fingers to keyboard")?Laughing

    Not sure that your story is about "forced feminization" though?  Jonathan appears to be quite a willing and enthusiastic participant in the proceedings. Wink


     2683 days ago 
    2 points