My Story of Degradation Ch. 03

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I go to Mistress's home and get put into chastity.
2.4k words
4.27
21.6k
9

Part 3 of the 3 part series

Updated 06/09/2023
Created 08/24/2018
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This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please.

*****

"Yes." Was all I replied.

I saw her nod to Cindy and felt Cindy behind me and the cold steel of the handcuffs go back on my wrists, Cindy shut them, and I heard the ratchets go as she tightened them as much as she could.

She then stood in front of me and at another nod from Mistress she turned and knelt before me taking my hardness in her hand and slowly licking the tip of my cock. My cock immediately started to twitch and get to full hardness as Cindy used her tongue to lick the drops of juice I was producing before opening her mouth and taking me in.

She was very professional, and I watched her head bobbing up and down and she took me in and out again, her tongue all the time stimulating me, and despite Mistress watching us and smiling, I felt as hard and horny as I had ever been and knew I would not be able to hold back for very long.

I just wished I had my hands free to grab the back of her head and force my cock into her throat, at least that's what went through my brain, despite Cindy taking me balls deep on her inward movement.

I groaned as the pressure built then closed my eyes and jerked my hips forward, exploding in Cindy's mouth, my cock pulsing five times or more before I stopped filling her with my cum, Cindy for her part was sucking hard and swallowing, she did not spill a drop, she was very well practised at taking a load.

Once she felt me soften, she withdrew and licked her lips making sure nothing was spilt, then picked up a ring from a tray beside her, I didn't remember it being put there, and pushed the ring over my now soft cock and pulled my empty balls through the ring as well. She then licked my cock and circled it get it nice and slippery before slipping on a plastic cage.

I was watching in awe at how easily I slipped into it when I noticed Mistress standing beside us, she had a simple lock in her hand which she pushed into the top of the cage, then turned the key, and pulled it out leaving me locked away.

Cindy stood and moved to my side as Mistress went back to her chair. "Good that's the first part done, it will be a long time before you cum again, I hope you liked Cindy, she is a very good cocksucker which suits her station in life, let's hope you become as good."

As she spoke my head was spinning, not only had I had a young girl suck me off, I was now locked in chastity and Mistress had the key, and what did she mean by 'a long time before I cum again', it took a while but then it dawned on me I was hers and she would be dictating how my life was led from now, no more one night stands, unless it was under her supervision.

"From now on you are to think only about pleasuring others, you will learn that life is not about you and your cock, but about giving pleasure to your superiors without demanding pleasure for yourself, prolonged chastity will help you to learn this."

"Now be a good boy and go with Cindy, she will show you how to dress and then we will meet in the kitchen, you will be Mary the Maid when I next see you." She giggled as she watched Cindy take my arm and lead me out of the room shutting the door behind her.

I chatted to Cindy as we went upstairs, she told me her history how at 18 she decided to leave home and become the woman that she knew she should be, that she had found Mistress after a while on the streets and that Mistress had initially taken her in, given her a home, got her onto hormones and generally treated her well. Now she had moved into her own place on her own, had a job but came back here to help Mistress whenever she could, this weekend was such a time.

Cindy stopped at a door and opened it and ushered me in. "This is the servant's room." She explained, "and this is where we will be sleeping until we leave Sunday night or Monday morning". I looked around the room, there was a super king size bed, so I assumed I would be sleeping with Cindy, then I realised as my cock tried to get hard, that a lot of good it would do me caged as I was.

Cindy pulled on my arm and led me to the bathroom, it was bright and spacious and had a wonderful vanity unit, very handy as she explained when you need to do your make up. Cindy then undid my handcuffs and I rubbed my wrists, then I gave her a hug, thanking her for the blow job. She waived it off saying it was what she was here to do, please Mistress.

I tried to kiss her, but she pulled away from me, saying we did not have time and that like me she was caged, and it was unfair to get us both excited. She went to a drawer and got out a bra and some falsies, then a panty girdle.

She came over to me and helped me step into the panty girdle, then she showed me how to push my testicles up into my groin, then tuck myself between my legs before pulling the panty girdle up, it was very tight and obviously too small but it did hold me well tucked and when it was finally up I was very smooth almost like I had no cock, it was then that I noticed it had no back, my ass was bare to the world.

I then sat down on the chair and she stood behind me and looking in the mirror she placed the false breasts over my own nipples, I realised they had some sort of adhesive on them, and she then told me to hold them in place as the glue dried and so she could get a bra on me.

Like the girdle the bra was a size too small, but it was nice and pretty, white lace, and it held my falsies close to my chest as the glue went off. Cindy then pulled the bra away from my breasts so that she could slip false nipple in them, making me look like my nipples were excited and proud.

She then gave me some very sheer stockings, black holdups, seamed at the back and I carefully put them on making sure with Cindy's help that the seams were straight at the back. Then she put my feet into some black high heels, four inches, as far as I could tell, with a small ankle strap, and a padlock for each which Cindy snapped shut trapping me in them.

"You will once you have got used to them progress to six inch heels, that's the standard for this house." Cindy stated in her manner of fact voice.

She then grabbed some make up and went to work on my face. I watched intently as she applied foundation first, I didn't really have any shadow, I was lucky I only needed as a male to shave a couple of times a week.

Once she had applied the foundation, she added a little colour to my cheeks before getting to work on my eyelids, they were subtle but not too vibrant, as she said they were to suit a maid not a working girl, and she followed the eye shadow with an eye liner and mascara, which I noticed was a very good brand and really did bulk up my eyelashes making them long and thick.

I then stood and followed her back into the bedroom. She went to a drawer and pulled out a corset which she showed to me then wrapped it around my middle, it was an under cup one so didn't interfere with my boobs, and she then told me to lean on the door and brace myself.

I had often worn corsets at home and put them on myself and pulled them as tight as I could, but Cindy was stronger than she looked, and this corset was a genuine bone one, so by the time she had pulled it in my waist had shrunk by a good five inches and I was struggling to breath properly. It also had the effect of straightening my back and forcing my chest out making me seem larger than I was.

Then it was time for my maids' uniform. Cindy took it from the wardrobe and held it up to me saying "It should fit, it's an interesting one has some 'different' features, which you will learn to enjoy."

She held it down low allowing me to step into it, and she then wriggled it up my body, it was cut low at the front showing off my cleavage, had holes at the top of the sleeves to make it look off the shoulder, and was long sleeved. The skirt was flaired and was also very short barely below my bottom.

As she zipped me up the back I heard another click. "That is one of the features, you are now locked into it, and this is the other." She moved round and fastened my sleeve cuffs, which could also be padlocked and had a d ring with a clip attached. Then she fastened and locked the cuffs before pulling my hands behind me fastening the clips together.

Then she took a wide posture collar and fitted that to my neck, it forced me to look straight ahead, and was stiff enough to prevent me looking down at my feet, once on again I heard the click behind me of a padlock.

Finally she got a blond wig from the hanger in the wardrobe and having put some adhesive on my nearly bald head she placed the wig on top, pulling and straightening it till she was satisfied, then she sat me down in front of the dressing table and combed it out, I was amazed how still it sat on my head, the glue must have been fast acting.

She then put the final touches to my lips, a bit of gloss followed by a deep red lipstick. She made me stand up and turn around for her, then said "I hope Mistress is pleased otherwise I am in for a beating, please do try to please her, please."

"Cindy of course I will, I will please her and then we can sleep together, I am looking forward to that even if I am locked away, I have always adored MtF girls, even from afar, to sleep with one even in these circumstances is a dream come true."

I watched as Cindy visibly blushed and giggled and then opened the door for us to go downstairs.

I tottered downstairs, still trying to get used to the heels and the fact that now I could not look at my feet.

When we got to the kitchen Cindy pushed me through the doorway and said "Mistress may I present the new maid Mary."

Mistress had her back to us but turned slowly and a bright smile lit up her face. "Cindy haven't you done wonders to her." She approached me, walking round me, lifted my skirt front and back to check my chastity, and spanked my ass, proving to me how vulnerable I was.

"Cindy I am more than pleased with you, she looks so attractive as a Maid, so I will give you a treat, you will sleep in my bed tonight, and Mary can sleep in the barn once she has finished her chores and pleasured the two guests I have invited to dinner this evening."

She then turned to me and said, "Tonight Mary you will start to learn that your place in life is only to please others, your own pleasure is of no significance although one day you will get as much pleasure from serving and pleasing as you used to from emptying your balls into some poor girl, your journey stats tonight."

For myself I was very sad that I would not be spending the night with Cindy, and why was I to sleep in the barn?

"Cindy darling show Mary how to lay the table, you will eat with me and my guests, Mary will serve us, and she really should be wearing a leash."

I turned and Cindy attached a leash to my collar then she led me into the dining room, and showed me how to lay the table for a three course meal. Once the table was laid Cindy showed me how I was to serve the guests. It all seemed straightforward although I was having trouble with the posture collar when it came to putting plates down without spilling anything, but after a bit of practice I was getting used to it so Cindy and I returned to the kitchen.

Mistress told Cindy to go and change, that there was a new outfit laid out on Mistress's bed and that Cindy was to wear that and do her make up to suit, I didn't understand what Mistress meant and Cindy looked a little puzzled but she departed to Mistress's room to get ready.

I was, despite my outfit and looking so real as a girl and maid, very nervous at the thought of being in the presence of strangers dressed like this, I very much wanted to please Mistress so that she would keep me on, and I also suspected that if I did displease her she would make me suffer for it.

Then suddenly the door bell rung. Mistress turned to me and said "Our guests have arrived, go and open the front door and welcome then in, if they ask your are the new maid on probation, take their coats and settle them in the lounge, do whatever they ask of you, understand."

"Yes Mistress."

"Then go, don't keep them waiting outside, stupid girl."

I scurried as best my heels would allow and got to the front door, and pulled it open.

To be continued ...

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4Leather4Leather22 days ago

Please next chapter. Mistress

WailAndGnashWailAndGnashabout 1 month ago

Not a great deal of degradation so far.

Lapper69Lapper6912 months ago

Eager to read more.

AnonymousAnonymousabout 3 years ago
Shit!

Too short of a story.

mrwidehorizonsmrwidehorizonsover 5 years ago
Nice!

Love where this is headed!

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