Tuesday, May 10, 2022

Mommy's Pajama Sissy -- Part 4

 As a cold winter gave way to spring, I knew it was time to start putting away our pretty flannel nightgowns. Although we had both enjoyed the coziness of our beautiful and feminine flannel gowns -- and the instant sensation of a slumber party that they evoked each time we put them on -- the nights were becoming warmer and it was time for a change.


Just in time for Tommy/Tammy's birthday in late March, I bought him two very pretty, very feminine lightweight nightgowns, one with little cap sleeves and another that was sleeveless.  And of course I bought the same spring nighties for me.

I thought my little Tammy was going to faint when he unwrapped first one and then the other. He held the soft fabric up to his cheek and positively beamed.

He took the cap sleeve nightgown upstairs and changed into it. He no longer needed my help doing his hair and make-up.  I had even put a small vanity table with a mirror and chair in his room so he would have a special place to make himself look pretty and to store his make-up and brushes and perfumes.

I thought he looked like a little princess in his pretty new nighties. I even started calling him "My Little Princess" when he was all dolled up.  I think he really liked it when I said that.


Something else happened that spring. In his pretty spring nightgowns, my little Tammy looked so grown up, so ladylike. I thought I might try exploring a new topic with My Little Princess...men.  I started very slowly and carefully. We started watching TV shows with more mature themes. These shows would often feature steamy love scenes -- and very handsome leading men. I would say things like "Ooh, isn't he handsome?" or "Look how strong and muscular he is," or "Mmmm, I think he's very exciting," as we watched our evening TV shows. 

After a little while I managed to get Tammy to engage me in conversation on the topic. He was, at least at first, a bit reluctant about voicing an opinion. But with a little bit of time and a bit of prompting from me, he was able to loosen up a bit and managed to admit to admiring the hunky men on the screen -- and sensing the thrill of the women that were in their arms. The more we watched and the more we talked, the more Tammy was able to imagine himself as the soft, feminine object of the male characters' desires. 

I knew that it caused Tammy some embarrassment to admit to identifying with the female characters in these romantic situations. But I explained to Tammy that it was perfectly natural for a young lady like him to have these feelings of excitement and desire for such masculine men. I explained to him that all girls want to be pursued by, and ultimately submit to, a real man.

I think my explanation confused and embarrassed my poor, sweet, little Tammy even more than he already was.  Oh well.  Maybe a few more pretty spring nighties would cheer him up, don't you think?

Tuesday, May 3, 2022

Mommy's Pajama Sissy -- Part 3


By the time Christmas arrived, Tommy and I had been sharing my collection of pretty ladies pajamas for several weeks.  He had wore every set I own at least a few times.  I thought Tommy would enjoy something new.

On Christmas Eve, it is our tradition to open one gift each, saving the rest for Christmas morning.  This year, I had picked out a very special Christmas Eve gift for Tommy to open.

When Tommy opened his gift, he was almost overcome with joy.  Inside was a pretty blue flannel nightgown of his very own.  "Oh Mommy!  I love it!  Can I put it on now?"

"Of course sweetheart," I replied.  And when Tommy returned downstairs in his pretty new nightie, he had a second surprise.  I was wearing the exact same nightie.  "Surprise, sweetheart!  Now we're twins!"  Tommy ran up and hugged me.  He told me he loved me.

I fixed his hair and put a little lipstick and blush on him.  I added just a spritz of the flowery perfume he liked so much.  He was simply lovely in his pretty new nightgown.

We spent all Christmas Eve -- and most of Christmas Day together wearing our matching nightgowns.  And we had a wonderful on Christmas afternoon snuggled up together on the couch under a warm quilt watching chick flicks on TV.  My sweet Tommy cried during "The Notebook."

Over the next few weeks I bought Tommy -- or as I was now calling him -- Tammy -- and me several more pretty matching nightgowns to get us through the cold winter together.