About my blog...

A collection of stories, pictures, thoughts ideas and more that are of interest to feminine and sissy males. I am open to submissions and guests posts on the blog. to email me just see my profile. Hugs...sissy terrie

Wednesday, February 24, 2021

Sissy Boarding School

Today's post is courtesy of Kevin (aka Karen) whose wife just recently officially made him/her a sissy cuckold.  Karen wrote the very first post for this blog at my request.  We had corresponded a few times and when I told her I was thinking of starting a blog and described what themes I wanted to feature, she volunteered to write a short story for me.  I hadn't heard much from her after that until two days ago when she sent me this little vignette, complete with pictures!   I hope you enjoy and I hope Karen continues to contribute when she can.

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    "First year students get the most basic of our rooms.  They're comfortable but simple.  If you get through your freshman year, next year's room will have more amenities" the dean of students said to Karen.  Her name was Ms. Smith.  She had a very pleasant smile but with an authoritative way about her.  "As you would expect gurls in their junior and senior years have the nicest rooms."

    Kevin's mother had decided upon this particular boarding school when she grew tired of catching Kevin rummaging through her things as well as his older sisters too many times.  As a single parent with a full time job, Kevin was becoming a little too much to handle. 

    "Get yourself settled.  Ms. Johnson will be stopping by later to issue you your uniform for class tomorrow and something for you to wear for dinner tonight" Ms. Smith said.  "Any questions?"

    "No ma'am" Karen said.  Ms. Smith just smiled, turned away and walked out of the room.

    The room was certainly not what Karen was used to.  Very tidy, feminine and totally void of any "maleness" like his room back home.  Though Karen had an affinity for girly things his room had all the markings of fourteen year old boy, with pictures of his favorite sports heroes on the wall and other boy things scattered about.  

    Everything in this room seemed so feminine with shades of pink everywhere and all types of little dainty things.  The twin bed in the middle of the room looked comfortable but Karen had a hard time imagining living here for four years.


    Despite its simplicity the room had a lovely view of the school's beautiful grounds.  Karen's room overlooked a lovely flower garden with brick pathways, grassy areas, bird baths and nice looking garden furniture.  It all seemed very peaceful and serene.  In the distance were lots of trees, fields and rolling hills.  "Kevin" was going to miss baseball and other sports.  There didn't seem to be any athletic fields in sight at all.

    Karen walked around the room.  At least there was a private bathroom even though it was pretty small.  She noticed it didn't have a shower and sitting on top of the toilet was a little tent card with the reminder: "Remember to take your seat!"   "There will be no standing to pee.  Ever." she remembered Ms. Smith saying downstairs in the large common living room of the dorm just after Karen kissed her mom goodbye earlier that afternoon.  It was all starting to be a bit overwhelming.

    Karen would make the best of it she thought as she put her small bag of personal belongings on the bed.  New students had received specific instructions of what to bring with them.  Other than the clothes on they wore when they arrived, the only other clothing items they were to bring were three pairs of simple white cotton panties.  Everything else was to be provided by the school.

    As she sat on the bed Karen looked around and decided to take a look inside the closet in the corner of the room.  It was wider that the one she had at home, with two doors that opened away from each other.  She opened the doors to discover the most beautiful collection of feminine finery in pretty pastels that she had ever seen.

    She couldn't believe what she saw.  How in the world was a school like this going to help her break what her mom called "this nasty habit of yours"????  As she ran her hands across the collection of pretty dresses, gowns and petticoats she couldn't help but feel the stirring in her loins...

To be continued.

Karen

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4 comments:

  1. Replies
    1. Don't they? Though my mom never directly supported my dressing, i think she must have known.

      xox

      sissy terrie

      Delete
  2. I was lucky. My Mummy used to let me dress in her underwear. After she caught me in my bedroom wearing her underwear and embarrassingly masturbating. I covered my thing and blushed bright red.
    My Mummy walked over and in a nice gentle voice told me not be embarrassed. As she reached me, she gently pulled my hands away and said it's perfectly natural to want to wear her underwear and she was flattered that I could get hard and masturbate while thinking about her.

    ReplyDelete

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