On one visit when I was 14, I had no sooner arrived when my aunt grabbed me and took me into the kitchen to discuss something “very important.”  She said that a close friend and neighbor in town had written a play that was going to be produced in the town playhouse on this coming Saturday night.  In one of the scenes, a teenage boy is forced to dress like a girl, including girl’s underwear and a frilly dress with a full skirt and petticoats.  A girl in the play then pulls up his skirt revealing his frilly panties.  The boy who was scheduled to play that part had just backed out because he was afraid of the ribbing he would get from his classmates in the local high school.  Her friend was beside herself because this was an important part of the play, although the character did not have a speaking role and only appeared in two scenes, one dressed like a boy and then dressed like a girl.  She said her friend had run out of possibilities.  No boy in the town or neighboring towns would agree to play the role.  She said, “I know it’s asking a lot, but would you be willing to do it?  You don’t live out here and no one will know who you are.  She’s a really close friend and critics from New York will be here to review the play.  Please do it for me.”

She saw me flushing with embarrassment, but waited.  She was always extremely nice to me, especially after my mother died, so I could hardly refuse.  She was looking at me with such concern on her face that I took a deep breath and finally said, “It sounds pretty stupid to me, but I will do it for you, but you can’t give her my real name.”  She grabbed me and gave me a big hug and kiss and went to the phone to call her friend. 

Just before dialing, she said, “What name should I use?”  I thought for a moment and said, “Tom Duggan.” 

My cousin Sheila, who had witnessed the scene came over to me and said,   “Thanks for agreeing to do it.  My mother has been sick with worry about her friend.  You’re a life saver.  But why not tell her friend your real name?” 

I answered quickly, “I don’t want to be listed in the cast in the Playbill.” 

When my aunt got off the phone, she said, ”Come with me.  We have to get you your costume.”  With that, my aunt, Sheila and I got into the car and drove into town to a girls' shop that was closed, but there were people inside who let us in. 

A very pretty girl about my age came over to me, all excited, and gave me a big hug and kiss, saying,   “You’re saving my mother’s life.” She then introduced herself.  “I’m Ginny,” she said.  She said “Hi” to Sheila, who was a good friend of hers.  Besides my aunt, there were three other women, all pretty and all wearing pretty dresses with full skirts.  “This is my mother,” Ginny said. 

The woman had tears in her eyes as she said.  “Thanks so much for doing this, Tom.  I can’t tell you how much it means to me.  This is my sister and that is the woman who owns the shop.”   Then she turned to my aunt and said, “You never told me how handsome he is.  He’ll be perfect.” 

The owner the said, “I’d like to get home before midnight, so come with me, young man.”  I went with her into a dressing room and she said “Take off all your clothes and put these on,” pointing to clothes laid out on a table.  There were very pretty pink nylon panties with plenty of lace, nylon stockings, a garter belt and, hanging up, were a pretty pink dress with a full skirt and a very full frothy white petticoat.  “Put on the panties first, then put the garter belt around your waist like this,” demonstrating.  “You’ll never get the stockings on without getting runs in them unless I help, so knock on the door when you have the panties on.”  

She left, and I was frozen for a few minutes and finally bit the bullet and took off all my clothes. I put the panties on and immediately got an erection.  I then put on the garter belt, but, panic stricken, I put on the petticoat to hide it.  The petticoat was gorgeous.  It was chiffon and caressed my legs.

I went to the door and knocked.  She came in and said, “Sit on that stool.”  I did as she directed and she promptly pulled up my petticoat and started to put on the stockings.  She couldn’t help but notice my bulging panties, but only said, “Don’t be embarrassed.  It’s perfectly natural.  Those panties are so silky, there’d be something wrong with you if you didn’t have that reaction.”  My face must have been crimson, but I said nothing.  When she had the nylons on, she brought over a bra whose cups were filled with foam rubber and put it on.  She then slid the dress over my head and pulled it down.  “Look in the mirror,” she said, “You actually look good in a dress.  Let’s go outside.”  She led me outside and my aunt, her friend, her friend’s sister and daughter, and Sheila were looking expectantly.

The two girls giggled and my aunt’s friend told them to be quiet.  “All right, now spin around,” said the playwright.  I did what she asked and I could feel the skirt and petticoat billowing up around me.  “The skirt’s too long,” said the playwright. 

The owner said, “I have a similar dress with a shorter skirt,” and she pulled me back to the dressing room.  She put that one on and went back out.  To make a long story short, I tried on five dresses until the playwright was satisfied. 

The playwright then said to her daughter, “Pull up his skirt.”  Ginny came over bent down and pulled the skirt and petticoat way over my waist.  (By that time my erection had subsided.) 

Sheila said “Oh la la,” and all the women laughed. 

The playwright said, “The color of the panties are wrong.  Do you have baby blue ones with a lot of lace?” 

Back into the dressing room and she handed me the blue panties.  “Take off the garter belt first and then see if you can get the pink panties off without taking the stockings off.  Put on the blue panties and the garter belt and knock on the door.  I did as told and knocked and she came in and hooked up my nylons.  My erection was back and she said, “Don’t worry.  Enjoy the feeling.  By the way, since I can’t sell used panties, you can have the pink ones as a memento.” She walked over to my clothes and stuck the panties in my pants pocket.  “They’re much prettier and feel a lot nicer than your boxer shorts.”  We went back out and I spun as told.  The chiffon petticoat was very silky and caressed my legs as it settled from spinning. 

“Sheila’s turn,” said the playwright, as Sheila came over with a devilish grin on her face and yanked my skirt and petticoat way over my head and said,  “Pretty panties!”  The women all glowed with enjoyment and none could fail to see how my erection was tenting out the panties. 

“That’s perfect,” said the playwright.  “You’re very handsome and look fabulous in that dress.  Every women in the audience will want to pull up your skirt and they will be thrilled to see how pretty your panties are.” 

When I regained some semblance of composure, I said, “Can I get dressed now?” 

“Sure.  There’s a dress rehearsal on Friday night, too.  The slacks and shirt you were wearing will be fine for the first scene you are in.” 

After changing, we got into my aunt’s car, with the dress and petticoat hanging from a hook on the back door; I got in the back of the car, Ginny on one side of me and Sheila on the other.  My aunt was driving and her friend was on the passenger side.  We went to my aunt’s house and Sheila brought me down to the basement with Ginny and said, “I’ll get some refreshments” and left. 

“You’ve been a great sport about this,” said Ginny and she put her arms around me and pressed herself against me.  “You deserve a little reward.  She then gave me long passionate kiss.  I had an enormous erection.  “I can tell you want to kiss me back so don’t be shy.  Sheila will take her time.”  I did start to kiss her back very tenderly.  “Wow, you’re not only handsome, but you really know how to kiss.” 

Holding up a bag, she said, “In case you were wondering, your nylons, panties, bra and garter belt are in here.  The amazing thing to me is that, even all dolled up in that stuff, you still looked like a handsome boy.  You looked amazing.”   

Anyway, on Friday night, we went down to the town playhouse and went through the dress rehearsal.  The girl, Alice, who pulled up my skirt was about 15 and very pretty.  For some strange reason the director had us do the skirt-lifting scene about five times.  There was a lot of giggling.   After the rehearsal, Alice came over to me, put her arms around me kissed me and whispered, “I really enjoyed pulling your skirt up.  You have got a great butt.”   I was speechless.

 *     *     *     *     *

Then came the big night.  In the first scene, dressed as a boy, I walk on stage; walk over to a fireplace; take one of the pictures on the mantel; look at it; put it back; turn around and walk off the stage on the other side.  All the while other characters on stage are talking.  I still have no idea about the plot.  Did I lose a bet?  Am I being punished?  I have no idea.

In my big scene, I walk on stage, turning briefly to the audience so they can recognize me from the prior scene.  I am not wearing a wig or makeup.  Alice slips in behind me and I feel my skirt and petticoat being lifted way over my waist.  The feeling was electric, and I think that the audience felt it.  There was murmurings, giggling, gasps, deep intakes of breath and other human sounds that don’t have names.  When the scene was over, I ran to the dressing room and got changed as quickly as possible.  There was thunderous applause when the play was over and the director told us all to get back on stage for a curtain call.  Alice came over to me and said, “You should have kept the dress on for the curtain call.” 

I responded, “Yeah, so you could pull my skirt up again.”  

With a mischievous grin on her face, she said, “Absolutely.  You were the highlight of the show, and I am sure the audience would have appreciated another peek at your petticoat and panties.”

 *     *     *     *     *

My aunt, Sheila, Denise and I went out for pizza afterwards.  They were all still very excited.  “You were great,” my aunt said. 

“The audience went crazy when Alice pulled your skirt up,” said Sheila. 

Denise said, “That petticoat was to die for, and those panties you were wearing were beautiful, too.  You looked terrific in them.” 

I was drained and when we got to my aunt’s house, I crashed and went right to sleep.

  *     *     *     *     *

The next morning, my aunt’s friend called.  My aunt was smiling as she listened, so I assumed that the reviews were good.  When my aunt got off the phone, she excitedly told us that the critics loved it and that one producer wants to have it open off-Broadway.  

In one review, the critic said, “The look on the boy’s face when the girl lifts his skirt is priceless and worth the cost of admission.” 

My aunt then said, “There’s only one catch.  The producer insists that he will only produce the play if you are in the cast.” 

PART TWO