Mommy's Pajama Sissy -- Part 9

Tammy never shared with me all the details of his date with Steve. But it was very clear to me that Tammy had had an amazingly romantic and passionate evening.

But now Steve was gone, having moved to New York, and I could tell My Little Princess missed him, even though they had only been together on one exciting date.  But the last day of school was fast approaching and that was something good to look forward to.

At Tommy's high school, they have a fun tradition where the graduating seniors -- of which Tommy was one -- come to school in their pajamas on the last day of school.  Of course Tommy had never been one to get very involved in school activities.  He never went to football games or pep rallies or things like that. So I wasn't sure if he would even want to participate in Senior PJ Day, as they call it.

Well, he DID want to participate. And he wanted to participate in a very special way.

"Mother," he said to me. "I've been hiding all my girlish feelings from everyone for so long, always pretending to be someone that I'm not.  Well, tomorrow is PJ Day -- and it's the last day of school forever. So I want to go to PJ Day as Tammy.  The real me.  In a nightgown.  And if people don't like it, well fuck 'em!"

Tammy had never used language like that in front of me before.  It showed how strongly he felt about what he wanted to do.  So I gave him my full support.

Senior PJ Day arrived and we both got up extra early.  We took extra time getting Tammy ready for "her" very first appearance at Tommy's high school.  I warned Tammy that people would be shocked and that he would probably get some pretty strong reactions from people.  But Tammy was determined.

We hadn't discussed it before, so I asked Tammy, "So what exactly are you going to wear today.  Which nightgown have you chosen?"

Tammy replied.  "I have a favor to ask. Can I borrow your white night gown and robe set?"                                                                                  "You mean the one with the eyelet and lace trim? And the buttons down the front?  I haven't worn that one in years.  Well, I guess you can borrow it.  But, it's a bit...grown up and...romantic to wear to school."                                                                                                    "I understand. But it's what I want to do." And with that, I dug out the nightgown set from deep in my lingerie drawer.                                                                                           Tammy put it on and he looked absolutely stunning.                                                                               Ten minutes later I was driving him to school.  His hair and make-up were perfect. He wore just a bit of perfume.  As we pulled up to the front of the school, I asked one more time, "Are you sure you want to do this?"                                                                                             

 "I've never been more sure of anything." And off he went to the entrance of the school.

All morning I worried about My Little Princess being at school looking like a bride on her wedding night.  I kept me cell phone with me in case I got a call and needed to rush to school.  But no call ever came.  At 1:00, I drove back to the school to pick up Tammy, as the last day always ended early.

"How did it go?!?!" I asked excitedly as Tammy climbed into the car.

"It was great!" Tammy said with a smile.  And he proceeded to tell me all about his day.