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How my chastity continued

How my chastity continued

She would tease me relentlessly at work, giving me sneak peaks up her skirt, shoe dangling in the break room, coming over to my cubicle to "talk" but more like to bend over so I could look down her blouse at her breasts. Sometimes when no one else was around she would play with my caged penis. She genuinely enjoyed teasing the heck out of me knowing there was nothing I could do about it.

She got me to admit that I used to masturbate and fantasize about her before we started going out.

And at first I had a real difficult time adjusting to the chastity. The first week she had me come over each day to inspect it and to check for redness or sores. A few times she tied my hands behind my back and unlock me to give me an orgasm, only to lock me back up be for untying me. She did her best to assure me that it really was no big deal and that I would still be permitted to cum three or four times a week, heck I was used to doing it myself every day, some times twice a day. So to go a few days in a row, especially with her office torments was hard. No pun intended.

It did not take long at all for me to notice that by having to wait a few days, and with the way she would tease me before hand that my orgasms were much more intense and the sensation lasted longer.

If memory serves it was somewhere along the second or third week that they started lasting for two to three minutes. I had always been envious of women that could have an orgasm that lasted several minutes long as the typical male orgasm itself only lasts a brief time from actual start to finish.

This increased pleasure, and the bonding that was happening between the two of us had me wanting this lifestyle more and more.

And she would use logic and reason against me. Things like "its not hurting you, and your actually enjoying it so whats the big deal?" "If you want me to stop doing this and let you out permanently we cant be friends anymore, AT ALL, you don't want that do you?" And reminding me about her boyfriend that cheated on her and telling me things such as "look right now were in the getting to know each other stage of our relationship, you do want to have sex with me some day don't you..."

Guys, you know the kind of things that women say that make you reply in the affirmative even though you don't really like it.

This went on for about six weeks and she convinced me we would save more money if we got a place together. Should have heard the sound of the "cell door closing". But she had me so filled with lust... That and I was starting to fall for her. Real love, love like I had never known before, or even heard of. The kind women fantasize about when they are watching those romantic movies.

At first living with her was great! Seeing her getting dressed in the morning, or undressed in the evening was a serious turn on and made my lust after her even more. Little did I know it was pushing me further down the path she was so brilliantly orchestrating. At first the frequency of my orgasms increased to most days of the week.

Then She talked to me about me going to sleep with my hands chained in cuffs to the head of the bead, the chains were long enough I could sleep comfortably but not long enough to touch my penis unless I really scrunched up to the head of the bed. She said this way she could unlock me before bed each morning, because she wanted to give me head first thing "because guys cocks are soooo hard in the morning"

Well yes that logic was sound, and she was putting blow jobs on the table. Up to that point they had only been hand jobs.

So now I am going to sleep in bondage and getting bj's in the morning. Then one morning she was "to tired" and took me to the toilet to relieve myself, then locked back on the bed until it went soft so she could lock me back up.

This progressed to fewer and fewer orgasms again. But I was still being locked to the head of the bed each night.

Up until that point the longest she had made me wait for an orgasm was about four days.

The next step. Wait, during the time she was also "teaching" me how she liked things done around the house, the usual stuff, put the toilet seat down, take out the trash, don't put my dirty clothes on the floor, that type of thing.

Then one day she told me it was time for me to go longer. It was just after giving me an orgasm on a Saturday. She told me I was not going to cum until the following Saturday.

I started to register my complaint right there that this had gone on long enough and I went on a bit of bitchy bit. She listened patiently, and when I was done she informed me that since this was the first time I had done that she was going to forgive it

THIS TIME. However if it happened again she would instantly DOUBLE the amount of time she sentenced me.

By Tuesday I was begging to cum, could not think of waiting till Saturday. I think that's where she wanted me.

On Thursday she said she would let me have an orgasm on the very next Saturday that I was completely clean shaven from the waist down. She said she wanted me shaved and it was going to happen sooner or later. Either it would happen by this Saturday, or the next, or the next or when ever. But the rule was clear no orgasm until I was shaved.

By Saturday I caved and agreed.

She tied me to the bed, put a garter belt on me, rolled stockings up my legs and put high heels on my feet.

Then she gave me three orgasms that day, all the time rubbing her hands and long nails up and down my stocking legs telling me how sexy my legs looked in hose and heels and how much it turned her on.

Its kind of a foggy blur of a memory but some short time after that she got me to agree to try on a pair of panty hose, and she had purchased a pair of black patent pumps with a five inch heel that actually fit my feet. Don't remember the details of how exactly she talked me into that, what I DO remember was the look in her eyes one day after giving me several AMAZING orgasms when she looked me in the eyes, her hand still playing with me and uttered those fateful words.

"You will never, NEVER, have an orgasm again unless your wearing hose and heels."

And locked me back up.

She then gave me two more of heels identical black patent with heel heights of three inches and four inches. She told me when I get home from work everyday I will put on my (she called them my) pantyhose and the low heels, the three inches ones and wear them around the apartment until bed time, but only after standing by the table so I can hold on to it the four inch heels for 15 minutes, so my feet will get used to being in high heels.

After I learned to walk in the three inch heels she would reward me with an orgasm. Then stand in the five inch heels and wear the four inch ones, then put a board under the five inch heels and stand in them, then wear them until bedtime. In this manner she trained me to walk in five inch heels.
Published by debbielynn
9 years ago
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11
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skibumhi
so damn sexy
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awesome
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Great story, I hope you will continue. I can see her dressing you up completely, then taking you out!
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this is getting really good. more chapters?
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So love this story of your training, just so jealous wishing it was me in your shoes, or should I say heels!
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jgg64
Would love to read more, very sexy
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KCUM
You are a very lucky man. 'Cell door closing' indeed! Count yourself incredibly fortunate that this gorgeous woman wanted you as her property.
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Here's wishing you are training me that way.
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azspike
Is she still training you???
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I really am enjoying this story, it's got a lot going on . Thanks for sharing
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Amazing story
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