Warning! Sexually explicit material follows.
"A DATE WITH JUDY"
In my senior year at high school I joined the drama club and tried out for a school play called "A Date With Judy." I got the part of Oogie Pringle, Judy's boyfriend. It was a play about teenagers in the 1950's. It was a very exciting time for me. There were several other guys in the cast, but it was mostly girls. I also doubled as the stage hand and wardrobe manager. Rehearsal was every night at 7 to 9 in the school auditorium. One night after a rehearsal, I stayed later than the rest of the cast to put away the costumes. In the dressing room was a cute pleated plaid skirt that just looked divine. Removing my trousers ever so gently, I slipped into the skirt and strutted around the room. The short skirt came to my knees as it tickled the front and back of my legs. I simply loved how the pleats kicked out as I walked around. From the prop room, I tried on a long black pageboy wig. On the dressing room table was all the makeup I needed to transform my self into "Judy," the star of our play. Out on the stage, I twirled around and stopped in Judy's marks, saying her lines from a few different scenes. Then I practiced bowing and curtsying to my invisible audience. I even flipped my pleated skirt for all the audience to see my pretend panties.
From the back of the theater came the sound of a lone applause. It was my drama coach, Miss Boyd and she loved my performance! Slowly, she came forward into the light and told me how beautifully I portrayed the character Judy and what a great little actress I was. She told me to get dressed and we would have a long talk. As we walked back to her apartment, she asked me if I liked dressing as a girl and how often I did it. I lied and told her it was the first time I had ever tried it. Miss Boyd invited me in for a Coke. We sat on her couch and talked some more about the play, school and hopes for the future. Then I said my good night and went home. In bed that night I thought about her all night long and how gentle she was with my femininity.
The next night after rehearsal, Miss Boyd asked me to stay after and walk her home. Back at her apartment, she had laid out an entire ensemble of pretty things, in my size, to try on. She instructed me to use her bedroom and take as long as I needed. I really didn't know where to begin, so I looked over everything she gave me. The soft feel and touch of the lacy undergarments caused a swelling in my pants. First, I took a shower and powdered myself with a sweet smelling strawberry powder. Standing naked in her room, I first slipped on her baby blue panties. Wow! What a sensation that was! I creamed a bit and felt an afterglow all over. The satiny bra was very small in the cup size, so I stuffed it with pink panties from her drawer. Just as I was about to attempt to put on the nylons, she stepped in the room.
Miss Boyd was beautifully dressed in a short white halter dress made of a soft silky flowing material. Under the skirt was a single little net petticoat, just enough to lift her skirt way from her scrumptious legs. Covering those legs were a pair of real silk stockings with a shocking black seam up the back. The halter was all that held her small perfect pear-shaped breasts in place. Through the thin white silk of her halter, I could see her areola and pointy nipples. Her hair was put in a long ponytail with a little upswept curl at the end. On her feet, she wore a four-inch pair of clear crystal high heels. Her long fingernails were painted a shocking pink. The lipstick on her luscious lips was of a matching color.
She lifted her short sweet skirt and showed me beautiful her underpinnings. Miss Boyd's divine ruffled satin bridal panties were set off by the lacy design of her garter belt. The net crinoline had a soft satin underskirt that swished as she walked. Then she turned her back to me and asked me if her stocking seams were straight. "Humina humina humina," I replied. The she kissed me on the cheek and called me a dear sweet boy. I almost passed out right there on her bed. I had dreams of her taking me sexually in her bed. In my dream, there we were the two of us dressed like visions in a sailor's dream, making love to each other dressed as women. Our skirts and petticoats were flipping in the breeze as we passionately screamed out each other name. This excited me beyond control as I ejaculated in my panties.
Tenderly, she sat beside me on the bed, where she showed me how to delicately roll up my pretty nylons and slip them over my pointed toe, over my foot and gently wiggle and slide the nylons up my legs. Once in place, she attached the tendrils of my cute silky garter belt, showing me how to attach the lacy tops of the nylons into the clasp. It was then she noticed I had soiled her panties. She asked me to remove them, wipe myself dry and handed me a fresh pair of satin panties that were just as smooth and silky on the inside as the outside. Double satin panties! I almost fainted.
After that, she handed me a pair of three-inch high heels to try on. She commanded me to stand up and walk around the room. All this time I began getting hard again as my hot poker bulged inside my panties. From the pile of lingerie, she picked up an ivory-colored full slip and slid it over my head. Softly, she pulled it down my slender frame over my hardness and to my knees. When she asked how it felt, all I could do was stammer and stutter. From her closet she handed me a soft full petticoat of dotted Swiss netting. Along the tiers were placed pretty red, pink, green and blue silk ribbons. She took me to her vanity and began the makeover of my face. First, she applied a liquid foundation makeup, gently massaging it into my skin. Then a dash of face powder. Applying the lipstick took some doing, as I wouldn't sit still due to the dull aching bulge in my panties. The softness of my pretty undies, slip and crinoline were driving me crazy! Appliclation of the eye makeup was done with a minimum effort, just a touch of mascara, eyeliner and drawing the extension of my eyebrows were all that was needed. I delicately painted my toenails with a delicious red polish and did the same to my fingernails nails. The final touch was a dash of intoxicating perfume. Boy did I smell good!
From a mannequin on her dresser she picked up a cute short blond wig. Before she helped me put it on, she smoothed my crewcut flat upon my head. After combing the wig, spraying it and adjusting the curl, she made me look in the mirror. I was gorgeous! The appearance of myself standing there in ladies' underwear with a pretty wig on caused me to feel weak in the knees. I was in love with that chick in the mirror.
Miss Boyd picked out a very pretty floral dress from her closet for me to wear. It had a light blue background color with darker blue, pink and beige tiny buttercups printed on it. The skirt was full and gathered causing many folds of the soft sensuous chiffon outer skirt. The lining was made of a satin taffeta in a light blue color. As I walked around the room, the swishing sound excited me more and more. Over my shoulders, she draped a delicious white cashmere cardigan, and for my hands she gave me a pair of soft white cotton gloves with a fine lace edging. She said we were going out that night as sisters. Before we left the house she had me twirl in circles, making my skirts billow out aloft, all the while showing off my lacy stockings and panties. She said my slip wasn't showing enough and adjusted it so just a glimpse of pretty delicate lace could be seen peeking out from under my full skirt. Then she taught me how to properly smooth my hands under my skirt, gathering the beautiful material, before I sat down. I was instructed to put one foot directly in front of the other as I walked. This caused my skirts to sway gently back and forth as I walked, showing the fine lace trim of my slip underneath. As we climbed into her "T Bird " convertible she gave me a white silk scarf to place on my head to hold my hairdo in place as we cruised through the night.
She drove us down the coast to a town where neither of us was at all known. At a small roadhouse on the highway we stopped and stepped out of the car then walked to a supper-club on the waterfront. In the soft warm night air we dined on freshly caught seafood and white wine. I was feeling very giddy.
Later, we strolled along the beach in our stocking feet, as the cool ocean night air rushed soft gusts of sea air up our skirts. She told me that, while she had many men friends, she had no girl friends and longed to confide in another sister. She asked me if I would mind being her sweet little sister and we could go out together once or twice a week. It meant I could dress up in her lovely things. She made it clear she did not want sex with me, as I was her student. Together, we spent the whole school year and following summer going out to dinner, the movies or just for a ride. Once she took me to the amusement park on the Palisades, where we rode the roller coaster, as out skirts flew up in our faces we laughed gaily. I'll never forget that summer and all that she taught me.
I went off to college the following autumn and we lost touch with one another.
A year later, she fell in love with the
man of her dreams and moved away. The week after her
wedding she sent me a large package. It contained all the
beautiful things she let me wear on our sissy dates. To
this day I think of her fondly and wonder how she is
tonight. I walk the beach alone dressed in all my
wonderful sexy silky attire, remembering that first hot
summer night when we bonded as soul mates.
Good night Miss Boyd wherever you are. I hope you read this and think of me fondly too. I'll always wear my silk panties forever!
Oh yes, the play. It was an instant
hit. The girl who played Judy had an attack of acute
appendicitis the afternoon before our opening show. Her
understudy got stage fright and couldn't go on as Judy.
Miss Boyd asked me to play the part of Judy. My part was
played as a dual role by one of the other boys in the
cast. As Judy, I was an instant hit of the show, my
comedic drag attire lending a new flare to the show. When
the curtain came down, someone from the audience
presented me with a bouquet of flowers. I cried with all
my heart as Miss Boyd hugged me in front of the entire
school. For an extra thrill, I attended the cast party
that night in full regalia of feminine attire, ruffles
silk panties, bra, silk stockings, dress and makeup.
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