Boot Ch. 06

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Further into the hands of Mistress.
2.7k words
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Part 6 of the 7 part series

Updated 09/05/2023
Created 04/10/2021
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Shame245
Shame245
11 Followers

Hi reader, welcome to the sixth part of the story.

If you haven't read the previous parts then I recommend that you do. If you don't want to follow that recommendation it is entirely up to you. I think this works on its own 'ish.

Either way enjoy.

I'm kneeling naked, but for a contraption around my member. I'm on the tiled floor of a brightly lit, clean white basement. Tight behind me, the woman I now know as Mistress, is pressing her knees into my shoulders while her hands hold my head facing forward. I'm looking directly at the crotch of the woman? sitting just in front of me. Cindy is a big blond with big hair. Her dark lidded eyes look down at me over a long slim nose and a wide smiling, purple painted full lipped mouth. Her dress covers a full bust but its hem has been pulled up to reveal wide spread, thick strong thighs and a delicate pair of pale blue lace panties. The surprise is that those panties struggle to cover what appears to be 7 inches of swollen manhood.

Mistress holds my head still. "Give me your hands boy."

As I raise them Mistress releases my head to hold each wrist. She examines the raw marks created by the recently removed metal hand cuffs.

"Hmmm. You did make a bit of a mess. I don't think I should use the metal ones on you for a while." With that she lifts my arms up and pushes them towards Cindy. "You'd better hold them dear."

Cindy reaches forward and wraps each wrist in her large strong hands and pulls me forward.

Mistresses hands again hold my head and she guides me in. With my arms held high I'm coming down on Cindy's crotch.

"Give her a nuzzle boy. Rub your nose in there for a bit."

My nose meets the soft cotton of the lace and pushes down the right side of the cock infront of me. I smell lavender and musk it isn't unpleasant but it's definitely a warm hardening cock under there. I close my eyes as I start to face plant into the crotch but I also don't want to register what I'm actually doing. Mistress starts to guide my head up and down.

"Ooh look it's weeping it's so happy." Mistress lifts my head up a little. "Look at it boy."

I can't look. This is wrong. This is not what I like or want. I'm a boot boy. Why is she making me do this? I try to resist and stop my head moving.

"Don't you want to thank Cindy for helping you. Are you failing to do what I tell you? Are you that selfish?"

"No Mistress."

Mistress leans my head back and I open my eyes.

"No. You don't want to thank Cindy. Why you ungrateful thing."

"B...boots. L...leather." is all I can stammer out.

"No, this is a punishment if you had forgotten. You didn't complete the clean up I requested. You then came without my permission. Because of this that is a cock that needs some attention from you. It's not getting any from me and Cindy needs some relief."

I try to pull away but there is no where to go. Cindy's grip is tight and Mistress is pressing into my back.

Then the pressure behind me is released. Mistress must have taken a step back.

"Hold him there Cindy. I think he needs some persuasion."

With Cindy's strong grip on my wrists I'm still going nowhere. I hear the click of Mistresses heels as she moves around the room. I try to move my head around to see but Cindy lifts my arms so they bracket my head. Looking at her she just carries on grinning.

The next thing I know is that I can feel multiple laces? moving up my back.

"This might be a good enough incentive, boy." Mistress almost gloats as the bundled of laces are pulled away just before reaching my shoulder blades. Then a slight whooshing sound starts. It sounds like Mistress is spinning them. The tips of the laces lightly but quickly brush my back. I feel a tingling along their short path. The whirling/whooshing sound continues. Another series of lines light up the nerves on my back. The tingling increases as the strokes keep coming. It's starting to sting after the 8th stroke in the same place. The pain is building. I try to wriggle out of Cindy's grasp but there is no joy there. The strokes are getting harder and Mistress is making sure a large part of my upper back is covered.

"Once you get the wrist action right you can keep this up for hours." I can hear a smile in Mistresses voice. "With the tips just brushing you I hardly loose any momentum but the stining just keeps building, I'm told."

As the sting builds Mistress expands the area being hit. Lightly over my lower back but harder on the top of my buttocks.

Cindy's grip remains firm and as I start to try to writhe around to get away from the torment, she closes her thighs hard into my sides.

"Hold still and take your punishment like a man......sorry. Keep going like the light weight boy you are."

Mistressess strokes start to get harder and longer. There is a bit more thud as the bundled laces hit. It feels less harsh at the initial contact but the tips flick harder and bring on more sting. It's definitely building.

Mistress keeps going. I first start to whimper then start begging her to stop. Tears are starting to run down my face.

"Stop whining, I'm just getting warmed up."

Mistress seems relentless. It stings and bites so much. I feel like I must be bleeding. Oh god this has got to stop.

"Mistress p...pl.... please." Some part of my brain warns me not to beg her to stop. If I try to tell her to do anything it is going to get worse. I can't take that. I can't take this even.

Just as I think I can't take more it just stops.

Mistress breathes right by my left ear. "Now boy, you have a choice; either provide the relief Cindy needs or take another 10 minutes of the flogger."

Kneeling, sobing with my arms raised high, I stare down at Cindy's crotch. I hear a click of Mistresses heels as she steps back. I can't take any more. Can I do this. I start to lower my head. I strain to get my nose next to Cindy again. She sense what I 'm doing and pulls my wrists toward herself allowing me better access.

"Good boy," says Mistress. "Just a nuzzle to start."

Without Mistress guiding my head I rub my nose firstly down the right and then the left of the cock infront of me.

With one hand Mistress pulls my head back. With the other she applies a pair of scissors to the right side of Cindy's panties. Swapping hands takes a moment before she attacks the left side of the panties. Once bothe sides are free the front of the panties fall clear revealing a purple topped, circumcised, veiny, hard male member pulsing slightly back and forward.

"Give it a lick boy, treat it like one of my boots." Mistress guides my head back into the crotch and I tentatively stick out the tip of my tongue. It hits warm soft skin. I'm immediately reminded of the soft kidd skin over the heel of my kitten heeled boots. This is a good deal bigger though. I start to lick in long strokes. Mistresses hand no longer needs to guide my head. The skin feels like soft leather, the veins almost feel like the ripple of toes in the front of a delicate shoe. I can do this.

"Good boy." I feel Mistress stroking my hair. "Now stop locking, open your mouth and take it in. No teeth though."

I do as ordered. As the head enters the spongey flesh bumps into my lips. No boot heel that soft could support a lady. This brings me out of my imaginings a into the realisation of the reality I'm trying to hide from myself. This is a cock and I'very just taken it in.

Mistress pushes my head down and Cindy moans. "Keep licking boy. Swirl that tongue."

As the head pushed further in I try to follow Mistresses command. Apart from the head the hard but soft nature does remind me of a leather clad heel. I am just licking it clean. This is what I wanted.

The head hits the top of my mouth then starts to move to the tip of my throat. I start to gag and cough. Mistress pulls my head up slightly.

"Relax, try to swallow it down."

What, Mistress can't mean it. Then I realise she does as she pushes firmly down.

I gag, cough and start to struggle again. Mistress releases the pressure for a little then pushes again. This repeats five or six times, I loose count. The repeated struggling coughing and even retching as I try to clear my throat. Tears are again rolling down my cheaks. I hate being sick, retching and feeling like this but Mistress continues. The cock isn't going away if anything its getting harder. Something in me gives and I find I've started to swallow. Its like a big mouthful of food. It goes down a bit further.

"Well done. Good boy, you can do it." Mistresses hand doesn't push down but it doesn't let me up either.

I realise I can't breath the cock is complete blocking my airways. I pull back and take a gasping breath. Then I feel Cindy push hard into me again. I swallow, it's definitely easier this time. Her pubes push into and tickle my nose. Oh god it's all in me. I swallow in surprise which gets another moan from Cindy. My arms are released and I feel strong hands grip my head. Cindy starts riding my head. Its hard but if I tome it right I can get a couple of breathes in. A few strokes later everything stops, the cock seems to swell slightly and I feel something going down my throat. I'm held for about 5 seconds before I realise what little air I've managed to get isn't enough. With my hands free I can struggle more forcefully and manage to push myself off and back into Mistress.

I'm dazed, gulping for air, huddled in a ball on the floor. Mistresses arms embrace me. "Well done, good boy. You did well for a first time." As she gently strokes my shoulders she looks up at Cindy. "Clean yourself up girl. Make yourself presentable."

From the corner if my eye I see Cindy gather her ruined panties wipe my saliver off her member then straighten up her dress and with difficulty get out of the hair and stand straight beside Mistress.

"Help me get him settled." Mistress states as she begins to stand.

"Up you get boy. Have a seat to recover. Your punishment is now over." Mistresses hand strokes my cheek as I start to move up to the chair seat.

I try to relax into the chair. As I lean back I feel the stinging of my back reawakened by the contact. It is manageable. I can relax as long as I don't try to move too much.

Mistress steps in, gives me a quick hug thenas her hands come back round she clips a seat belt across my lap.

Mistress steps back, waves at Cindy to stand up. What was she doing on her knees? They both turn and leave the room. The lights dim but don't go out.

I sit looking into space as I try to understand what has happened since I entered this house today. It doesn't want to straighten itself out. The office, the mistake, Cindy, the punishment. Oh my.

I'm not sure how long I stay there staring at not much but eventually I start to take note of my surroundings.

Directly to my left is a small stainless steel sink with white glass fronted cabinets above it and white cupboards below. Then moving round the wall there is what looks like a shower but the head is too small, round and bullet like rather than a spray head. In front of me is a large glass fronted cabinet with what looks like medical implements on the top shelf, leather items on the lower shelf and various black and skin toned plastic? and rubber? items on the middle shelves. One of the items is a black pile of laces with a glass handle. The flogger? I think Mistress was using on me. To my right is the plain white door Mistress left through. Beside that are a couple of IV stands. One has what looks like a hot water bottle hanging from it.

When I finally take notice of the chair I'm on l realise that beside the chrome and black leather look it is quite complicated. My ankles are actually strapped in to individual leg rests. I tentatively lean forward to try to release them but the straps are locked. My back starts to sting a little again. After a quick check I see that the end of the waist belt is also locked with some form of solid hasp.

As I check out the rest of the chair trying to move my back as little as possible, I see straps at the sides and back. I can also see a number of levers, all but one are out of reach. Unfortunately curiosity gets the better of me and I try to move it. When I do my ankles start to be forced apart taking my knees as well then the cushion I'm sitting on starts to move apart. No matter what I do to the lever the pressure is always outward. I'm left with my legs spread, the cage on my member hanging free, my thighs supporting most of my weight, my backside hanging over fresh air and my hands firmly gripping the arm rests to take the rest of my weight and my back aching as I force it into the padding. My heart is now racing.

It feels like i'm balanced like this for 5 or 10 minutes until I can relax and let the chair actually take all my weight. It isn't uncomfortable it was just surprising. I feel very exposed now.

A while later Mistress walks I to the room as the lights turn up to full brightness. She is wearing my black kitten heels again. As my eyes travel up she appears to be wearing a white doctors coat. It's buttoned up tightly from her knees to her neck. In one pocket is something black with laces but I can't make out what. Midtress doesn't appear to be wearing any make up but she still looks beautiful. Placing a hand on each arm of the chair she looks straight into my eyes. I see strength, happiness and a little puzzlement their. She slowly looks down to my exposed crotch then back up into my eyes. Her face is stern her lips are a thin line.

"You surprised me boy. I think you actually liked part of your punishment. Cindy was most happy in the outcome."

She steps back then walks over to the sink. "In fact I'm not sure it was actually a punishment for you. I've been thinking I would like to try something further."

She bends down to open the cupboard under the sink. I can now see that under the doctors coat she is wearing stocking with suspenders holding them up. She retrieves a tissue box with black tissues? sticking out. It's only when she pulls one out that I realise they are rubber gloves not tissues.

Putting the box down she takes another and then begins to put them on. A couple of snaps indicate they are in place. I can hear the slight crinkling and small escapes of air as she make two fists then relaxes her hands and smiles at me.

"You seem to derive pleasure with your mouth. I've been thinking I may have to use another opening. But you will need to be leaned first."

I sit dumb in the chair. My mouth starts to open and close but much though I want to say something, my brain just refuses to work. I can't think of anything else to say to that.

Mistress reaches over and gently rubs my cheek. Oh you poor dear. You really haven't lived have you.

Shame245
Shame245
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READ MORE OF THIS SERIES

Boot Ch. 07 Next Part
Boot Ch. 05 Previous Part
Boot Series Info

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