Miss Jacquline's Challenge

Charles has been coming to see me for a few years now, he is a nice boy. a fun plaything. I really enjoy giving him massages and energy work. Most of the time he becomes putty in my hands. I can control him a bit, he likes it and I do as well. I give him some challenges. Edging, chastity, even some self-prostate play. He is very eager to please me and I him. In my own way. I have kind of devilish idea that will put him to the test for sure.

I call him. "I have instructions for you. Come over right away." I know will be here shortly. About 15 or so minutes later there is a knock at the door. I open up. I give him a nice warm comforting hug, "Hello my dear boy, please come in." I have some tea made for us and a light snack. Charles is so very attentive. He pulls my chair out and helps me get settled before he does. And in favour, I will not touch anything until he is seated.

We have a little small talk, how are things, the weather etc. But he knows something is coming. I put down my teacup, and look him straight in the eye. "I have your next task ready.. Will you comply? Good boy. This is what will happen. I will give you 2 days to prepare, then the challenge starts. You will edge for 19 days. NO orgasm. your edging time will be minimum 1 hour per day. If you go longer that is a good thing. But no less. You will be in chastity the rest of the days. You will have minimum 3 nights spent locked. There will be minimum communication between us. All I require is one daily communication with what you have done for me. On the 19th day you will come back to see me and I will decide at that point to extend longer or not. Oh... and one more thing. Bring that little plastic prostate toy you are always going on about."

Two days later I send him a reminder. It starts today. NO orgasm for 19 days. Do you understand? The reply back was immediate, "Yes Miss Jacqueline, I understand. I will contact you tomorrow. -Good boy".

Every day I received a message with what Charles has been doing. I did not respond to all of them, but when i did there were slight further instructions. Either, edge longer or make sure you sleep in the cage tonight. I did not ask for pictures; his word is his bond. and I trust him. On day 16, I contacted Charles. " On day 19, you will come to my studio at 2 pm sharp. DO NOT BE LATE."

reply was "Yes Miss, 2 PM I will be there. Thank you." On the 19th day, 1.55 in the afternoon, there was a knock at the door. It's raining and cold. I did not answer. He is 5 minutes early. 2 o'clock. Another knock. This time I open the door. "I did say 2 o'clock did I not? I know it's raining can cold, but my instructions were for 2 PM. The next time I will send you away." Charles kind of put his head down a bit, I took his hand, "Please come in. The rain may have taught you a lesson. Please go to the foyer. "How long have you been edging? 19 days is that right? -"Have you had an orgasm?"

-"No? good. I did forbid it. And you edged every day? How is the chastity cage feel now? a little tight and heavy I assume. -"How many nights have you slept with it on?" - "4? Good, that is 1 more than I had instructed. Good boy. Very well done. I am so pleased with you. Time for your massage. please go to the room remove all your clothing and hang it up.

Charles goes to the massage room as directed. I have some scents of lavender in the room it's very soothing for my clients. I have to admit, i enjoy the scent as well. I wait a minute until i can hear him settle on the table. I give a light knock. "Are you ready? may I come in? I hear a low yes. I am sure he is ready. I walk in the room now; Charles is lying face down ready to go. I love my work; it can be so very rewarding. I know my clients are in some kind of discomfort, and with my massage and energy healing, I can help. I begin with some good intentions, and then proceed. Charles can be very energy sensitive. I have brought that out within him, some slight touches in the right areas. can be electric, for both of us.

I begin by asking, is it your intention to have a heathy body, mind and spirit? -Yes Miss. it is. he says humbly.

Very well. Take a few deep to the belly breaths. He is so ready. I can feel him sink into the sheets almost. I start on his back, nice light rubs to get a feel of how he is handling his stress. I have worked on him on a few occasions and he has been so stiff and sore that his back feels like a gravel road. Just full of knots and tension. I work a little deeper and he is starting to release some of his pains. Moving down to his legs, hamstrings and calves. He is on his feet a lot all day. His legs are heavy and tired. Moving up to his neck, working out his tensions. his shoulders down his arms a bit... he is turning to jelly on the table. we have very little talk; he lets out little moans. and i can feel him wince in pain if i find a sore spot....

I lean in to his ear... "My little cub, it's time to turn over". -Yes Miss. Now is the time where I can really shine. I can make him feel good. I I know he feels safe with me. I look at him and he is at peace. I start back down at his feet. the top of the foot this time. Right even between the toes. It's amazing how soft the skin can be there, and very sensitive. He is falling deeper in relaxation. Up the sides of his calves. More tender areas. Inner thigh, I like to get close, but not too close to his genitals. He knows it and so do I. Each arm, high shoulders, forearms and wrists, and his hands. He does manual type of work, and kneading his hands and stretching his fingers, one by one. it's kind of funny, that the hands can give all kinds of stimulation, but can also be receivers of stimulation. He sighs deeply the stress and strains of everyday life, sometimes are buried in the hands. I take my time there. More and more he is sinking out of consciousness. last part of my massage is the scalp and face areas. The crown chakra is wonderful. I feel so much energy from him here. this is where we really connect on a spiritual level. I start at the base of the skull at the hair line, kind of scratching my fingers in little circles behind his ears. Charles breathing really changes now, very short breaths in and out. I can see his feet starting to move a bit, the energies in the room are changing now, getting very deep. I continue to massage his head, now around the ears, to the top of his head, His toes are curling, he is panting, they say some people don't let themselves go enough, but my little pet will. he gives me control, let's me heal him. Let's me balance him. It's a very comforting feeling. His feet are really going now, tightening up, spreading open his hands are clasped together. I am working on his sinus and forehead. Across his eyebrows, over his nose. It is very soothing. I know he is lost in sensations. He almost sounds orgasmic, his body is moving uncontrollably, lots of twitches and little spasms. "Ok my little cub, shhhhh... " I start to bring him back to earth... "ssshhhhhh.... it's ok.. I have you... I walk over to his feet to ground him.. "I have you, come on down now.". he starts to slow down and relax.. "There you go. Very nice. Are you ok?" -"Yes Miss I will be. Thank you." "Good boy. Take a minute to rest. I will come back in shortly. Sit up when you can." "ok.". it was very faint. A few minutes later, I knock on the door, "Are you all set?" - "Yes I am sitting." I walk in the room, there is a feeling of peace and wonder. I am carrying a box with a little something extra as a treat. He has no idea what is about to happen. " My dear little cub, I have 2 more little tasks for you today, something a little fun for you to earn your freedom from the cage, and perhaps even orgasm. Charles' face lit up, then got a bit of a worried look.

You enjoy your nudity do you not? He has a little sheepish grin, "I will take that as a yes. You get to spend the afternoon naked looking after a few details I need done here. " "Very well." I open the box. "I have restraints here. 2 for the wrists and 2 for the ankles. You complete 1 task you get one set. the next you get the 2nd. Come with me. " Chalres follows me to the living room. "Time for a little cleaning. You will vacuum this area spotless. and I will follow you to be sure it's done right."

The vacuum is in the closet there, and Charles gets right at it, there is a section of hardwood and some area rugs. All the attachments are there and he is being quite careful and cautious taking his time to make sure all is done to the standards I expect.

I start to inspect the room. Charles turns off the machine, I point at an area, close to the window, there was a bit of dust left. I pointed...."Look here!" I said quite abruptly. There is some dust left right there, by the window. I walked right over to it, and moved the blinds open, swiped my finger though it.... RIGHT HERE. He hesitated to get closer. "Are you a bit afraid someone will see you? It's up to you to finish your task." My pet takes a little studder step forward... "you are so close to your reward." "Yes Miss." he brings the vacuum around to get the final spot. He asks. "Is this sufficient?" I go to the window area, "Much better. Looks very good. You have earned your ankle restraints. Put the machine away, and come stand here. Charles complies. He walks over to me. "Spread your feet please." One by one I put on the leather ankle restraints. He looks down at them.

"Next task is dishes. Hand wash only." "Yes Miss. My pleasure". he said. We go to the kitchen and I show him the dish pile from the night before. I had a few friends over for a lovely meal. "Can you handle this?" -- "I am sure I can Miss." but with a little worry in the tone. I grab his balls, hard. I look him right in the eyes. "Miss who?" "Miss Jacqueline. I am so sorry." He begins. Warm water to rinse, then fill the sink. One by one the plates, glasses cutlery is cleaned and dried. If there was one that did not make it past inspection, it was handed right back. Of all the dishes that he cleaned only 3 were given back. Charles changed the water 3 times. As he dried the dishes, I put them away. As a bonus, he cleaned off the counter and got the sink spotless. "Very nice my boy," I grabbed him again, this time not as hard. His knees went a bit wobbly. -"Thank you, Miss., I really did my best."

"That you did. Now you have earned the other 2 restraints. Put your hands in front of you." My little cub complied. First the left wrist, then the right. This time he really stopped and starred at the cuffs. My plan was working. He was not standing as tall as he was a few minutes ago. the dynamic was changing as bit. His shoulders were starting to slump a bit.

"Go to the massage room and wait there. There is a folded blanket on the floor. Kneel on it and face my chair." "Yess Miss." I follow him down the hallway then I make a turn to my room. I stop for a second to make sure my pet does as told. It's quite the sight, watching him kneel unsure of what is to happen. I get into full mode now. My plan is set. I get changed quickly, High boots. a bit of a heel not much. Thigh high stockings, Garter and corset. I walk out with meaning, make sure my pet knows I am on my way in the room now. Charles glances to the side, not looking up at me. I move the chair closer to my little cub and sit. He is looking down. I pull up his chin to look right in his eyes. "Hey, are you there?" "I am." he replies. "You tell me that you can orgasm hands free? We have chatted a few times about this I know. He tells me "I can miss Jacqueline; I have only done it with my toy inserted." "Is that right? I must be witness to this. Where is the toy now? You did bring it with you? I did tell you to. He nods yes. "Very well. I walk over to his bag and spot the prostate massager. I take it out of the bag, and hold it so he can see it. "Is this it?" He nods yes again. "Did you bring lube?" "Yes Miss J, it's in the plastic bag there." "Ah, there it is." I open a drawer and get my latex gloves. "Lean forward my boy, and get on your elbows." He does as I demand. I go behind him and I lightly feel the softness of his ass. The fun starts now. I spread his ass a bit in a teasing way, then down the side of his legs, to his knees, turn my hands inside, and make my way back up. I cup his balls with one hand, and pull on the cage with the other. I hear am small moan. His back arches slightly. "Well, don't you feel a bit full here". He is leaking precum quite a bit. "I bet I could make you cum just by pulling a bit more on the cage." He is reeling now. I get a bit of a firmer grip. "But you will not. NOT YET. Do you understand" "Yes Miss". I can hear the fear in his voice now.

I pull the cage with a bit of power and go right up to his ear. "Yes MISS WHO?" "Yes Miss Jacqueline" He is feeling weak now. I can feel it. He wants to cum but does not want to. His mind is racing. "Do you want to cum today? DO YOU?" He nods yes. and his body shakes a bit. "No, you don't. do not move please." He is so, so mine now. He is ready to collapse. "Good boy. That's my good boy."

I stop what I am doing to him, the poor little cub, It's time for more fun. I take the lube out and put on my gloves on. I drop some on his ass as well. He jumps a bit. "You should not leave your lube in a cool area for long." with a bit of a giggle I said. I gently massage his ass for a moment. It can be a sensitive area, once I am sure there is enough there, " You will feel a finger entering your ass". Nice and easy i slip a finger inside. One knuckle at a time. Making sure i have enough lube on my glove. I begin to work my finger in and out slowly. Finding an area that he is familiar with. The prostate. I turn my finger downwards. Making little circles. and i feel it. The little firm spot inside there. He sighs. hard. "Oh, what's this here? I know this spot. He starts to move his hips, swaying a bit. "Ah, you like this?" I hear a lot muffled moan. "Would you like another finger?" He is in ecstasy. I will take that as a yes. I slide another finger in. Charles is almost whimpering. If I know one thing, when my G spot is stimulated just right, I can start to shake and squirm. Charles is lost completely lost in pleasure; he is leaking so much precum. Hips are swaying moving back and forth, side to side. I am letting him enjoy this, but only for a moment,... then.. I say. "Do not move". He stops right away.

"All you have waited for in the past 19 days, culminated to now my sweet boy. Do not move." I get more lube. Pick up the toy, I admire it just for a moment. I wonder to myself, this little toy. Hmmmm... I lube it up. "I will insert the toy now." There is a moment where we have both longed for all day. I touch the skin of his ass, there was a slight twitch..."Ah, no moving." I guide the toy slowly. I place my thumb and index finger either side of his little hole, make little circles around the entrance slightly pushing it in. It's not a big toy by any means. Just a little longer than my fingers. I push it in right to the base. He flexes his ass a bit. I give his butt just a tap. "No. Not yet. Off your elbows. Hands behind your back please." he sits up. Hands hesitantly behind his back. I click the clasps for his wrists together. I straighten him up a bit more. Then his ankles. I pause for a moment to admire what I have just accomplished.

I stood up, walked over to my chair, my one finger siding right up his back and over his head. I can see the shivers shooting through him. His head is still down, unsure of what I will command next. I can see him moving his hips again, getting the toy to set in place right inside. Slight humping motion, a little back and forth. His head is still down. I can see his expression he is loving the feeling of what is inside him. He is a bit helpless, can't use his hands at all. His breathing is starting to change a bit. His prostate is now awakened. Shorter breaths. Moans, twitches. Charles is still looking down. I am so amazed how this is developing. He is a world of his own. Almost slipping out of reality. I lift up his chin. "Hey there, are you with me?" He nods. "Flex your toy in for me." He does, A full body shiver takes him over. "Impressive." He is in total bliss now. "Take all the time you need my little cub." I really want you to enjoy this, and me be a part of it." I am not even sure he heard me. He is way out on another wavelength now. Eyes are rolling back in his head. I have heard stories of guys absolutely losing themselves during prostate play, and I want to see it for myself. HIs hands are clenching behind him, his back is tensing, knees are shaking from side to side. He is really panting hard.

"Come on my boy, cum for me. I know you can do it. His eyes open. He is looking at me but I don't think he sees me. I have a diecious idea. I slide my hand down his chin, over his chest, right to his nipple. He shutters hard.. I knew it.. this will work. I have actually caught him once or twice flicking his nipples during a massage. He throws his head back. "Yes, my little cub, you can do it. Cum for me. I am pinching his nipple ever so slightly. Rolling it between my fingers, He is close.. real close now. Almost sounds like he is in pain, but he is not. not a chance. Full body shakes now. He is going to cum right here, right now.

"Look at me boy.. LOOK at me. "

Have you even seen anyone cum and cum really hard? It is truly a sight.

Charles opens his eyes and looks at me, he starts to smile. "Yes, my boy... let it all go". He starts to cum...he is moaning uncontrollably, its taking all I have to hold on to him. He is really letting it all go. It is truly a wonderful sight. My little cub getting his reward after all he has done. Orgasm is an amazing sight to behold. We all feel it a little differently. I love being a part of this. He is really cumming, right in front of me. There is a look on his face. A mix of pleasure and a bit of pain.... the wonderful kind. His body so stiff now. Right at the tipping point.

The cum is starting to pump out. I counted, 5 streams of cum. Pumping out. The cock in that metal cage is trying to bust out of its lock. That is a lot cum.

Charles is starting to ease now. The orgasm is subsiding. I take his head onto my lap, "Good boy, that's my good boy. Shhhhh. " He is panting, so out of breath, all the tense muscles are relaxing now. " I have you, you are safe in my lap. Shhhh" He is still twitching a bit. But not as much now. He is coming back to reality. I hear, "Thank you, Miss Jacqueline, thank you." He is done, spent. I am sure that if I let him, he could sleep right here on my lap. "I am so proud of you." I stroke his hair. "I am going to stand up, please for now put your head on the chair". I place a small rolled up towel on the seat of the chair. I stand up and walk behind him, and gently release the restraints one by one. "Lean forward please, and relax a bit, I am going to remove the toy. Ever so gingerly, I ease out the toy. "It's amazing to believe that this little plastic wonder can give so much pleasure. Do you think you can stand?"

I help my little cub stand. He gets a little unstable. "Oopsie. Are you ok?" He nods yes, and winks. "You are going to love this." I shuffle him back over to the table. I help him lay down. I cup his chin, "Such a good boy. This is your time now; you have earned it." One by one, the restrains are taken off and I place his limbs back on the table. "Now, where did I put that key?" I playfully feel around my waist and fake pockets, feel my way up to my breasts. "Oh yes, here it is." I reach in and take out the key to his cage. We looked at each other and I winked at him. I hold the device and insert the key. It clicks. It was like an immense weight was lifted off. Very slowly I slide off the cage. I could almost feel his cock breathe. Then I open the base ring, Charles was totally free. "There you go. Well-earned freedom. Please just close your eyes, and relax."