Wednesday, June 29, 2022

Mommy's Pajama Sissy -- Part 5

Well, I imagine you could already guess what might happen next. I couldn't stand having My Little Princess with me only when we were home alone and wearing our nightgowns. In early May I went out and bought Tammy some pretty dresses and shoes that he could wear out in public! 

There was a bit of nervousness at first, as you might expect. But the thrill of going out in public in a pretty dress was more than enough to motivate Tammy to summon enough courage to join me on some real-life adventures.                                                                                                                                           After several days of planning, we were all set for an exciting weekend together. Friday afternoon was very warm, so I dressed Tammy in a gauzy turquoise dress -- he looked simply lovely! Our Friday adventure started with a visit to the nail salon, where Tammy got his first mani-pedi. He was so nervous at first that his hands were shaking. But he settled down and his pretty soft pink nails looked divine. Then I took him to the mall where I let him pick out -- and try on -- several more new dresses and shoes and handbags. We went to three different department stores and must have been there for two hours! And of course I needed to buy him some bras and panties -- today he was borrowing my under garments but needed a collection of his own. Then we had dinner together at a restaurant where Tammy realized that he was getting some serious attention from our waiter!  Tammy handled it well and we had a simply wonderful time.

I had a busy Saturday planned for us. I dressed Tammy in an elegant royal blue silk dress. He looked stunning -- and so grown up! We had lunch together at an intimate cafe downtown that is very popular with ladies out for the day together. Then a matinee of a play at the Civic Auditorium. And finally, the highpoint of our day, we went to a fundraiser reception at the art museum.  Since alcohol would be served, the event was restricted to guests 21 and older -- which Tammy wasn't.  But I was so confident in his ability to appear like a grown-up lady and I knew this wouldn't be a problem. When the ticket taker asked the two of us for our IDs when we entered, I simply said to him "thanks for the compliment" and the two of us walked right on in to the event.  It was magical.  The museum was beautiful, the guests were all dressed up, there was a string quartet playing -- it was heaven! And I could see that My Little Princess was in heaven too.

Waiters passed glasses of champagne and little hors d'oeurves. About 45 minutes into the event we found ourselves near one of the bars where a young gentleman was chatting with a bartender.  I struck up a conversation with the handsome young man whose name was Steve. Steve looked very dapper in an expensive suit and tie. He seemed happy to have someone to talk to. He told us that he had recently finished business school and was home visiting his parent before starting a new job in New York with a big bank. He explained that his parents had bought tickets to the event, but were suddenly called out of town for the next few days. He was attending the event alone and didn't know anyone else there. Of course I introduced my lovely young Tammy to the handsome young Steve. Tammy had had several glasses of champagne by this time and was starting to loosen up a bit. It didn't take long for Steve to start flirting with his pretty new acquaintance. And it didn't take long for Tammy to play along and join in!

At one point Steve excused himself to use the restroom. "What a catch!" I said to Tammy. "Oh stop, Mother!" he replied. ""Don't be silly."

"I'm not being silly," I answered. "He's obviously smitten with you and I can tell you like him too." Tammy turned bright red when I said this. "Why not see where this goes. He's only in town for another two days. Then he's off to New York. Why not see what can happen before he leaves town..."

Tammy was initially dumbstruck by my suggestion.  But his internal feminine needs -- and the champagne -- pushed him to be bold enough to surrender to his urges.

"Alright, mother," Tammy said. "Let's see where this goes."

1 comment:

Lee said...

Wonderful, Tammy is finally getting out and interacting with people. Perhaps her Mother can help with her social skills.