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Stephanie's Chastity Chapter 1
By Stephanie

His hands sweated and his pulse quickened as he gripped the steering wheel. He couldn’t believe he was actually going to be transformed.  But things were coming together in ways he hadn’t  thought were possible.  It all started with a woman from his office interrupting his surfing the web.  He thought that she hadn’t seen the website that he was on, but apparently she had, because the next morning he saw an e-mail in his inbox with the website as a heading.  He opened it, expecting to find some kind of smart-ass comment like he’d seen before, but was surprised by the content of the e-mail.  It was a well written by Christine, who complemented him on his willingness to explore his feminine side.  She asked him to fill out a questionnaire that she had attached and return it to him as soon as possible, so that she could determine what level of commitment he was at.  She said that while she appreciated men like him she didn’t have time for game players, and this questionnaire would determine if he was really interested or just a gamer.

He printed out a copy of the questionnaire and began to fill it in.  It asked his name, where he lived, age, what he wanted from being feminized.  It also inquired about his experience in being feminized, what his limits were, and how soon he wanted to meet.  Finally it asked if he would be willing to spend at least one week of his life being totally committed to this transformation, in other words would he be willing to spend 24/7 in being trained.  He carefully thought through the questionnaire, answering as honestly as possible, then he went to the computer and filled out the questionnaire online and attached it to his reply.  Again there was trepidation in his thoughts that she would run it through the office and he’d be the brunt of jokes for years to come.

It took a few days but he finally received a response to his questionnaire.  Christine, announced that she had reviewed his questionnaire and found him to be a worthy candidate for exploring his feminine side.  She also said the plus was that he lived close to where she did so that not only could she rain him for the week she could help him on weekends as well.  She said that from here on she would refer to him as Stephanie and he was to call her Mistress Christine.  She asked him to provide her a phone number so that she could contact him when she wanted outside of the office and she wanted to start training as soon as possible.  Finally she asked if this was acceptable to him and if it was that he should comply with her basic instructions.  He was taken aback by this but responded that it was absolutely fine and he provided her his cellphone number and signed the e-mail sincerely, Stephanie.

That evening while he was driving home from work his cellphone rang.  He picked it up and a silky voice on the other end asked for Stephanie.  He responded that it was.  “Good, this is Mistress Christine, I hope you’re able to talk freely.” She replied.  “I can.” He replied.  “Good, Now Stephanie, what is it about being feminized attracts you?” she asked.  He thought for a moment and said, “I’m not sure, I’ve never really thought about it.  I just like the way women’s clothes are.  Also I guess I’m submissive in nature and like aggressive women.”  “Interesting, and how do you feel about being trained by me to be as feminine as possible?” “Well, I guess excited and nervous at the same time.” He responded honestly.  “Don’t worry, I’ll lead you through the transformation, and will put your mind at ease through the whole process. Nobody likes a nervous gurl.”  She replied.  “Well that’s good to know, I’ll be the first to admit I’m really nervous, but really want this.”  “Good, well the next thing will be for you to prepare for our meeting, because I don’t want to have to waste any time with your training getting you ready. Call it studying for your test.”  She laughed.  He laughed nervously, but said “Ok, I’m ready.”  “Well then the first thing you need to do is to go and get some panties and start wearing them.”  She said.

“Ok, what kind should I get?” He asked.  “You choose what you want, after all you’ll be the one wearing them, not me.”  She responded.  “Where do you recommend I get them from?”  He asked.  “That’s up to you, I can’t make all the decisions for you.  Also look at nylons and shoes.”  She replied.  “I’ll call you again tomorrow at this time to see if you have been successful.”  She said and hung up before he could ask another question.  He nervously went to a store and bought a couple of pairs of panties in black and red.  He also bought three pairs of thigh high nylons in black.  And then he went to a shoe store and found a pair of black heels that he thought might fit and went to the check out.  He nervously paid for the shoes and said he was buying them for his girlfriend, the woman behind the counter smiled at him, like she knew and as he left he felt her eyes following him out the door.

The next morning Christine was at his desk, she handed him a file, which was business related, but slipped inside was a note from her asking if he was wearing his panties and nylons.  He nervously looked over to where she sat and saw her looking at him with an amused smile on her face.  He nodded yes and quickly pocketed the noted so that he could dispose of it later.  Throughout the rest of the day he was conscious of her watching him.  He felt a nervous and his stomach was in knots.  He couldn’t focus on work but tried hard to look like he was busy.  Finally it was time to leave and as he headed toward the parking lot he heard footsteps coming up to him.  Then he heard Christine say, “Nice panty lines Stephanie” as she passed him and made her way to her car.  He didn’t know what to say, but quickly looked around to see if anybody else had heard her comment.  Obviously nobody had, so he quickly got in his car and headed towards home. 

That night Mistress Christine called and advised him that he needed to shave his legs and be ready to take the next step soon.  That night he carefully shaved his legs and also trimmed his pubic hair, even though he hadn’t been directed to do so.  He went to sleep that night and dreamt about what was going to happen next. 

The next day at work, while he was at the copy machine, Mistress Christine came up behind him and whispered, ’Are your legs silky smooth?”  He whispered back, “Yes, I shaved my legs.”  She smiled and said, “You’re making good progress I think we need to schedule a week off where you and I can help you realize your feminine dream.”  “You’re right, I need to do this before a chicken out.”  He replied quietly.  “Good, I’ll e-mail you the dates and you get the time off.”  She responded and quickly left.

He went back to his desk and constantly was checking his e-mail to see if she had sent the dates she wanted him to take off.  He finally got her e-mail and saw the week she wanted was two weeks from that day.  He quickly looked at his calendar and saw that he didn’t have any projects so he quickly sent a vacation request to his boss which was approved.  He then e-mailed Mistress Christine and told her that he had the time off and was looking forward to being taught about the feminine ways by her.

Continued...