Natalie’s sissy training

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Natalie finds courage

    Natalie rear was sore for several days after her last session.  She found herself admiring the WW bruise and felt proud it was there.  It gave her pleasure that Mistress Windy’s mark was there.  In her head she was contemplating being sassy or something else that might warrant punishment again.  It saddened her as it faded but alas she knew who she belonged to.  

    As I’ve noted in recent submission, Natalie weekly tasking have become fairly routine.  More of maintenance tasking and this is the part of Natalie’s timeline that She has begun documenting her journey with this blog.  Hoping to show others that even though everyone’s journey is different we are not alone as proceed through it.   Even though I am Natalie, I learn more about her everyday and this blog helps me understand and vocalize the feeling that both I and her have.  We are 2 sides to the same coin.  Natalie’s persona is more and more on my mind, even though I go through everyday life as a male, my feminine side Natalie is ever present.  

  As the days progress Natalie keeps thinking about things from previous sessions with Mistress Windy.  So far Natalie has been lucky Mistress has allowed a release at the end of each session, but fed Natalie her cum.  The last couple of sessions Mistress has asked Natalie to perform a pineapple experiment. She wants to know if the stories are true if pineapple sweetens the taste.  Natalie has taken this task on and for the 2 weeks in between sessions she has eaten diced pineapples at least once a day. 

   The day approaches for the next session, and Mistress is pushing the envelope on how brave Natalie can be.  Mistress wants Slutty Natalie to drive to the session. This will be as for out as Natalie has gone in public.  She is nervous but excited at the same time.  She does her normal session prep then puts on a very sexy and short red dress with a black garter and stockings.  Then she attempts make up, this is not Natalie’s strong suit, but she makes the attempt.  She then proceeds to the car and drives to the dungeon.  Natalie is careful not to make eye contact with other drivers.   When she arrives Mistress Windy is amazed at how sexy Natalie is.  They take some pictures prior to the session.  

   The session is amazing as usual, but there is a twist this time.  In the previous 2 weeks Natalie  disobeyed Mistress and had a release without permission.  For this transgression. Natalie will be denied anything at the end of this session.  Mistress assures Natalie that she must learn a lesson that her releases are only to happen with Mistresses permission.  Natalie understands, but regrets that she won’t be able to complete the taste experiment this time.  None the less it was still an amazing session as usual.  Until next time Natalie will continue her pineapple diet in hopes that she is allowed a release. Until the next post stay positive.  

Natalie is a BAD sissie

     Natalie has grown significantly in my psyche over the past few months.  With weekly taskings to learn to embrace my for feminine side.  The weekly taskings have become more routine, no longer does Natalie have to be told to wear panties and stockings everyday.  She only needs to be told when the instructions differ i.e. colored feminine socks instead of stockings.  Her exercise routine is more routine now.  Even though it is routine Natalie anxiously awaits her weekly list in Sundays.  This has become a part of her routine as well.  Each week Natalie is tasked with at least two photo shoots to show off on her social media.   Sometimes Natalie struggles with these.  It is not the taking of the pics, that actually excites her.  Where Natalie struggles is the creativity of what outfit, pose or content that will match the theme she has been given.   Natalie takes the pics and posts them to twitter and fetlife hoping that they bring enjoyment to others.  

     Another aspect of Natalie’s presence on social media that pleases Mistress Windy is her positive attitude.   Every morning Natalie posts a positive inspirational comment on Twitter.  With so much negativity in the world she wants to try and lift the spirits of those around her.  If just one person finds joy in the posts then it is worth the effort.  Natalie wants everyone to be their best selves.  

   This week Mistress Windy had special plans for their outing. They were going to meet at the dungeon first and go to a special place that Mistress had in mind.  So when Natalie arrives in her man clothes black slacks and a pink polo, just for Mistress Natalie always tries to wear Mistresses favorite color on the outings.   Mistress comments that that might be too nice for where they are going, but it will be ok.  Natalie had a thought of where they might be going, but just waited for the surprise. After lunch it is time to go to the secret location.  Natalie drives them to a local adult theater to visit the glory holes and porn theaters.  Mistress assures Natalie that this is just a scouting expedition.   When they arrive Natalie pays and they go in.  Instantly they are followed by several men undoubtedly due to Mistress Windy’s exceptional presence.   They enter one of the glory holes so Natalie can put her remote control plug in.   Mistress Windy wants to play.  Next they go to one of the large rooms and sit on the couch, but alas the plug doesn’t seem to be working.  Mistress Windy instructs Natalie to drop her pants right there.  Not wanting to disappoint she does as instructed.  As they guessed the plug was off.  Mistress turns it back on now she wants to play but feel the vibration too.  She instructs Natalie to sit on her lap while she plays with the plug.  Natalie sits on her lap, but not having body awareness she accidentally elbows Mistress in the eye.  Natalie apologies profusely, they both laugh and continue on.  During all of this several other men have come into the room and one on the couch next to us begins to masturbate.   Mistress and Natalie just laugh and make funny comments on the porn.  They sit there for a little while longer while Mistress continues to play with the plug seeming to enjoy herself.  It comes time to leave and they go back to the dungeon.   Natalie goes and removes the plug and the talk for a few minutes and then part ways.  Now later that evening Natalie gets a text saying she is in trouble.  The next text is a picture of Mistresses black eye.  This was a first for Mistress and punishment was coming at the next session.  Natalie understood and told Mistress that she would accept whatever punishment that she deemed fit.  

   The week goes on and Natalie continues her tasks.  Mistress decides to let her and Natalie’s followers decide her punishment.  The top 2 vote the  getters the whole pole were spankings or needles in her clitty.  It was a neck and neck race and Natalie was getting nervous, she didn’t want the needles.she felt much better when spankings barely won, she only hoped that Mistress wouldn’t exercise her overriding vote.  Luckily she went with the winner and allowed the spankings.  She warned Natalie that this wouldn’t be pleasant even though one of Natalie’s hard limits was no lasting marks , but this was deserved and she would leave marks that lasted for at least 2 days.   Natalie agreed to the terms, she knew she deserved it. As the session began Mistress was right that the spankings were not pleasant, but she made it through.   Mistress ensured that her initials WW remained,  she was good it lasted for 3 days.  It was painful but deserved Mistress accepted her apology and lessons were learned.  Until next time Natalie’s journey continues.   

Natalie coming into her own

  Now that Natalie has a bra she needs something in them.  In her first session Mistress Windy had put breast forms in her bra, this felt odd at first but exciting at the same time.  Now it was time for Natalie to get her own “boobs”.  She was excited she got to go to her favorite website Amazon, and with Mistress’ permission even.  She looked around and found some she thought would work.  They looked nice and the reviews were good so she sent the link for approval,  Mistress Windy told her to get c/d cup, those would be good for her.  

   The forms came in a lot faster than Natalie thought they would, she was excited now in her photo shoots she would look more like a woman.  This made Natalie want to shop even more.  She needed more clothes and not the “grandma” clothes.  She needed sexy and seductive, Natalie needed to boost her esteem.  She clearly doesn’t have the sexy curves of a woman, but wanted to be desirable to look at.  So she went to old faithful Amazon.    Natalie looked and looked, found a couple promising dresses, but alas she couldn’t buy without approval.   As she found a dress she would promptly send Mistress a screen shot of the dress.  To Natalie’s delight Mistress approved of a couple, she particularly liked Natalie in red.  A beaming Natalie quickly purchased a sexy red number that was approved.  She also went out on a limb and purchased a couple of bras (now that she new her size).  These item came in quickly and Natalie was so anxious to try them on and show Mistress Windy, who once she saw the pictures while heartedly approved.  She was proud of how far Natalie had grown in such a short time.  

      As the time between sessions passes Natalie continues her taskings and enjoys them immensely.   Mistress and Natalie agreed to (when time allowed) would meet for lunch, a shopping trip, or a mani/pedi really just what ever Mistress wanted to do at the time.  The first outing was just a lunch where they chatted, learned more about each other.  The more connection they had the more intense the sessions would be.  Mistress tells Natalie that she really appreciates how Natalie’s submission is full and complete, it makes the session more enjoyable for both of us which is the ultimate desire.  Mistress Windy’s absolutely loves what she does and when there is an intense connection it makes it even better.  Natalie is extremely grateful to Mistress Windy for her lessons with a firm but kind hand.   

     The time for the session finally arrives.  Mistress plans to push Natalie a little further.  Her instructions were for Natalieto drive to the session with her breast forms and bra on.  Nervous, but not wanting to disappoint she does as instructed.  It wasn’t as bad as she thought.   The session was as expected.  Mistress Windy knows how to design a session to put her sub of whatever fetish in complete surrender and sub space.   When the sad time for the session to end comes Mistress gives Natalie some water and they chat for a few minutes before Natalie must clean up and leave.  Natalie’s story will continue, as Mistress says Natalie isn’t going anywhere. 

Natalie grows stronger

     Natalie is now further apart if my being, and her relationship with Mistress Windy grows.  Mistress Windy and Natalie develop a strong Domme/sub bond.  This is important for Natalie connection is really important to her.   She asks Mistress Windy if they can go on outings, Mistress Windy agreed.  The first one will be after their next session so Natalie takes the day off of work to be able to devote the proper amount of time to spend on both a session and an outing.  Over th next couple of weeks Natalie is very excited but nervous, she has no idea what Mistress has planned only that she knows it will be lunch and some sort of shopping.  

   As the time until the session drags painfully slow in Natalie’s head.  She continues her daily tasks exercises, videos and phallic foods.  Mistress Windy decides she wants to have some more fun with Natalie.  She instructs her to purchase a blue tooth anal plug as well as pink rechargeable  vibrator.  As usual Natalie promptly did as instructed after all it meant she was able to shop.  The plug and vibrator came in very quickly.  So from now on Natalie was only able to masturbate using the vibrator and either her plug or dildo,but she is no longer allowed to use her hand.  That didn’t really matter she had only had a release once outside of the sessions with Mistress Windy, and that one Mistress Windy allowed. The first time she used the plug and vibrator it was intense and it wasn’t long before she had to quit or else she would be a bad sissy and mess her panties without permission.  Natalie was able to control herself but just barely. She didn’t dare try that again for a while.  

      Mistress Windy however had other ideas for the remote control plug but it would have to be tested first.  During there next conversation there would have to be a set up and test of the plug.  At our next chat she was instructed to have the plug in and powered up.  It took a little back and forth to get Mistress Windy’s app set up, but once it was set up you can hear the joy in her voice as she plays with me from afar.  We chat for a while as she continues to modulate the vibrations bringing both of us joy.  

     Finally one of the Natalie’s favorite days arrives and this is an even better day.  Mistress Windy and Natalie (albeit in boy mode) will have an outing after the session.  Natalie can hardly contain her excitement as she prepares for her session. She still doesn’t know what Mistress has planned, but her heart is in a flutter of anticipation.  She is greeted at the dungeon as usual by an impeccably adorned Mistress Windy who in her heels is taller than Natalie, but that doesn’t bother her it just makes it more exciting.  This time Natalie had her own dress and shoes for the session.  It was a short blue dress black thigh highs accompanied by 3 1/5 inch heels.  The practice had paid off she was much more comfortable walking in heels now.  After Natalie is dressed and her make up is applied.  Mistress Windy and Queen Kat prep Natalie by spanking her ass.  Mistress Windy is visibly impressed as she tells Natalie that obviously she has been putting in the work,  her ass is very firm and obviously her best asset, but Mistress will still be taking that asset as her own.  The session continues an usual Natalie is in heaven amongst these two beautiful strong women.  

    As the session ends Mistress Windy, Queen Kat and Natalie head to lunch.  When the arrive at the restaurant Natalie is instructed to go to the bathroom and insert her plug, Mistress Windy wants some amusement.  Natalie returns to the table a short time later, as she walks to the table Mistress Windy smiles as she begins to vibrate her playtoy’s butt.  All through lunch Mistress Windy modulates the plug, she gets such enjoyment out of this.   Lunch progresses they talk about Natalie’s progress and how proud they are of her.   Finally it has come time for the surprise Mistress Windy informs Natalie it is time she got her own bra and we were going to get sized for one today.  Mistress Windy new this was a huge step for Natalie, and promised she would make sure she got through it.  The next stop was the store as they walked in.  Mistress Windy told the clerk that Natalie needed to be sized for her first bra.  Now Natalie is in full outward appearance a male (she still was wearing panties and stockings though). The clerk showed them how to size her, Natalie is a 46 A, but when we look around we look for c/d cups, Mistress Windy obviously has plans.  This turns out to be a difficult size to find, we find a couple and go to the dressing room.  Mistress wants the clerks opinion.  She is happy to oblige she is super fond of inclusion and is happy Natalie came in it made her day.  Natalie made her purchase, and you could just see how pleased Mistress Windy was. She told Natalie she was proud of her for taking this next big step, Queen Kat agreed this was a big step and they were both extremely proud.  Natalie is growing fast and is getting hard to contain.  Mistress Windy is up to the task and is proud of her work with Natalie.  Until the next time when we follow Natalie through her journey.