Caught In the Middle of the Night

                First, read my story in "When I First Crossdressed"

    It had been hot - and we did not have A/C or a fan to move cool air through the house.  Nevertheless I didn't let that stop me.  I had been setting a small alarm clock for 2 or 3 A.M. to wake me so I could get dressed without my parents knowing.   Unfortunately that night they were not resting comfortably and were restless.

    When My alarm went off, my father was sitting on the stool in the bathroom, smoking a cigarette.  I doused the alarm, and slipped into my closet with my flashlight.  Pulling out the suitcase hidden in the back of the closet, I opened it and started to remove the things I would wear (my mother's nylons and corset, my aunts blouse and skirt, my sister's slip, and fur jacket, and a pair of opera length gloves she had bought, and finally a pair of high heels and a pillbox style hat I had bought from a consignment shop.

    I heard my father flush the toilet, and I quickly shut off my flashlight.  I heard him padding to his bedroom and a brief bit of talking with my mother.  Waiting until they quieted down, I again turned on the flashlight and began to dress.

    First, the black nylons, then the corset, and attaching the nylons to the corset straps.   I looked at my image in the long mirror on the back of the closet door and knew I was going to enjoy this.  Next, I pulled on my sister's slip, and then the blouse and skirt.   Slipping my feet into a pair of high heels I had bought at a consignment shop came next.  I loved the feel of being dressed, rubbing the silk slip against the black nylons gave me quite a thrill.  Finally, I added the fur jacket and a pillbox style hat with a veil from the consignment shop.  Gazing at myself in the mirror I added a coat of red lipstick to my lips and then opened the box of soft white perfumed powder I had bought the previous day.  I coated my face heavily with the powder since I had no other makeup.  So I was now dressed up and very very hott!  Admiring myself in the mirror for several minutes, I again rubbed my skirt and slip against my nylons...loving the feeling.

    Now I turned off the flashlight and opened the door, listening carefully to see if my parents were awake.   No sound at all!   Now, carrying the box of perfumed powder, I walked quietly over to my bed and got in,  lying full length with my head on the pillow.  Grasping the powder puff, I covered my face in powder, emptying the box on myself.   I lay there glorying in the feeling of being dressed up and powdered heavily.  I added another coat of red lipstick to my lips by feel and then lay there quietly fantasizing about being with my three aunts.  Pulling up my skirt, I began to ********** while dreaming of the erotic scenes we enjoyed together.

    Well, I must have made some noise in the process because I heard my mother say,"I'll just go check on him" and heard her bed creak as she got up.  Panicking, I pulled up the covers to cover myself hoping to hide my clothing.  She came in and asked, "Are you allright?  I answered yes. and she saw the covers over me, and grasped them pulling them down saying, "Its too hot to be covered...all you need is a sheet, if that!"  Unfortunately, her hand brushed the fur jacket I was wearing and that was followed by, "What are you doing?"  Now the lights came on and I was fully exposed as a heavily perfumed/powdered girl!  

    I ran into the closet and began pulling things off, throwing all but the jacket into the suitcase, then pulling out one of her dresses I had not chosen to wear.  I frantically rubbed the powder and the lipstick off before I emerged chastised and embarrassed...she didn't know I liked dressing up with my aunts on weekends (see the story in "When I first Crossdressed").  

    My sister was woken up thy the noise and she in turn asked, "Whats happening?"  My mother answered, "nothing, go back to sleep."   I hesitatingly asked my mother not to tell my father, and she said I will think about it, now go back to bed and to sleep.

    She didn't tell my father, but my sister had not gone back to sleep, peeping around the corner of her doorway to see my all dressed up.   Later that day she "blackmailed me" into dressing up for her when my parents were not home.  She had a boyfriend who was, I think, Gay, and he had told her he liked to dress up too.   So, the next time my parents were out for an extended period of time, She "made me" dress up and powder up and then opened the door for her boyfriend to enter, and got him dressed up too.  She put makeup on both of us but we didn't do anything but sit around talking ...I wasn't sure at that point what i would have done anyway.   She did make us kiss each other before we went back to boy mode though.

   Several other times, I had to dress up for her, but only one other time with her boyfriend...who later moved away with his family.

    The weekend visits with my aunts continued for me, along with the dressing up with and for them and the oral sex - both ways.   We never did tell my mother about that!






SuzanneLebizarre SuzanneLebizarre
70+, M
1 Response Aug 9, 2009

I too was blackmailed by my sister and then dressed by mom and sis as I grew up from 8 yrs old. My sister gave me all her hand me down dresses and I wore them everyday. I still dress 24/7 in lingerie and wear dresses everyday as I'm 0ver 50 now and still love to be sissified.