Natalie’s presence continues to grow within me, and wants to have more exploration in the outside world. To enable Natalie some freedom Mistress Windy continues to provide me with takings. I have at this point stopped wearing boy underwear all together and no longer wear man socks. I am only wearing panties and stockings or going commando occasionally with stockings. At this point I have begun to make some online purchases. My first significant purchase was as Mistress Windy called them stripper heels. She was utterly amazed that I purchased 6.5 inch heels. When I attempted to walk in them I was not steady at all, but this is all I had to practice my walk for the time being. Natalie continues to practice her walk and do “sissy squats” in her heels.
As the time in between sessions goes on Natalie begins to purchase make up as instructed. She goes into Ulta to purchase lipsticks, lip gloss and nail polish. Mistress Windy has plans. Natalie being the overzealous sissy that she is she purchases eyeliner and eye shadow as well. Mistress Windy understanding what Natalie needs for her nurturing continues to bring more of Natalie’s femininity to the surface. Along with wearing waist trainers to give her more of a feminine shape, she must learn to sit lady like by keeping her legs closed or crossed. In addition to this she must no longer stand to pee while tucking her little clitty so she looks more like a woman when she sends her pictures to Mistress Windy. Soon these actions just become natural for Natalie, she begins to feel normal and doesn’t feel comfortable standing to pee. Either to humiliate or further train Natalie she was instructed to purchase several large bananas, cucumbers, carrots and condoms and only those items.
The much anticipated week of Natalie’s next session has arrived, but the remote training continues. She must eat one of the phallic objects at each meal, practicing cocksucking on one of the at the meal of her choice. Natalie eagerly completes these tasks daily. As the session day come closer, a new task has been added, Natalie must use a cucumber, and a carrot to exercise her pussy. Natalie is nervous about this but compares and it wasn’t as bad as she thought. Mistress Windy continues to push Natalie’s boundaries one particularly task is to wear her clear lip gloss all day, anxious and scared, but not wanting to disappoint her Mistress she complies and is surprisingly comfortable with it.
Finally the best day of the week arrives. Natalie prepares herself as she normally does with a thorough flushing, but on this day Mistress Windy wants Natalie to wear lipstick to the session to further Natalie’s comfort level with her femininity. As Natalie drives to House of Whispers she doesn’t even worry about the fact she is wearing lipstick in her boy clothes. She is just so excited she gets to see her Mistress these days are Natalie’s most favorite times. She gets to be fully under the control of a strong powerful woman who knows what Natalie needs deep down and never fails to put her in a euphoric sub space. Today’s session did not disappoint Mistress Windy’s expert technique put Natalie at complete ease as she was transformed into who she is meant to be. For the next couple of hours Natalie can truly be herself without judgement. After the session reality sets in and Natalie must once again go back to the real world and transform back into her boy self, but Natalie remains on the inside even if the only outward appearance is her panties and stockings that she wears. Until the next installment Natalie’s journey continues.
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