An Ongoing story I wrote
December 13, 2007
Diaper Dare
December 13, 2007
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Nanny Sylvia

       Ms. Lylan carefully unlocked her door and let her friend in, in front of her. “It won’t take me anytime to get ready Sylvia, why don’t you just have a seat I’ll get you a drink.” She said as she motioned for Sylvia to go in. The sound of four heels clicking on the hardwood floors filled the house.  

     Sylvia followed Ms.Lylan into the kitchen as the talked about the week ahead.  The ladies stopped, and grew silent.  There at the doorway to the kitchen and hallway was Jake, Ms. Lylan’s nineteen-year-old son who was home for college for the holiday.  His presence wasn’t the shocker. However he was dressed in a shiny satin white bra, a white satin thong and matching stockings. His face turned beet red as his eyes met his mother’s.  He started to walk off

.       “No no no Jake, you just come right in here!” his mother told him. “Sylvia, this is my son Jake,” she said. Sylvia stood there stunned. Jake had tears forming in his eyes and he could feel his pulse thumping rapidly in his temples. His erection clearly standing out beneath the panties and there was no way to hide it. He stood and the moments the women spent examining him seemed to be hours.       “Well he is looking very pretty.” Sylvia finally said breaking the silence.  Jake felt a lump in his throat. The stranger walked over to him with his mother behind her. Their hands moved over the bra and panties, feeling how smooth the fabric was. “This is certainly a big surprise for me, I had no idea you had a sissy boy at your home.” She said smiling at her friend.  

     “Neither did I Sylvia. Neither did I.” Ms.Lylan said. Jake wanted time to stop, or to rewind or speed up, or anything so as to stop this from happening to him. In spite of being humiliated and terrified of what was to come he stood ever so tall beneath the satin panties.   

    Finally he had to say something. He had to try and end this embarrassment. “Mom, can I go to change please?” he asked. She stared at him and smiled. “Please Mother!” he pleaded.

      “What do you think Sylvia?” she asked turning away from him. “Have you any ideas at all in your head?” The women laughed and laughed as tears started falling down Jake’s face. “Why you are just a pansy little sissy aren’t you?” his mother asked him.    

    Jake said nothing.  Instead he turned around and started to walk upstairs. Sylvia caught him by the wrist.  “I don’t believe you were dismissed Missy” she said to him sternly. Sylvia walked him into the living room with his mother behind him.  “Your mother invited me here, and she had a feeling you would be found this way today.” She told him.  

    Jake looked confused. “ I noticed every time you come home for Holiday I end up missing some sort of undergarments. See it used to happen more often, but it stopped around the same time you started college. “Ms.Lylan told him. Jake hung his head, lowering his eyes.” I also found your blue box,” she said.       Jake jumped up and started to grab his coat as Sylvia and his mother got him. Sylvia pulled out some soft suede wrist restraints and buckled them to his wrists behind his back. Then she carefully latched them together. “You aren’t going anywhere!” she said.   

   Ms.Lylan smiled “as I was saying Jakey, I found your blue box in your closet. I know that in addition to dressing in my panties and bras that you have been wearing cloth diapers and plastic pants as well. I saw all the bibs, bottles, the powder, and everything.” She started Jake in the face as she said this. His eyes were wide as could be.  

    She went on “I’m not mad at you Jake, quite the opposite. I do have to work in the day though and cannot stay home to care for a baby girl.” Jake looked at her strangely and over at Sylvia “that is where Ms.Sylvia comes in. She is going to help me care for you.  Sylvia has a few years of experience with sissy babies like you. “     “Mom, I, really, I…”Jake tried to stammer out an excuse. Sylvia put a finger to his lips. 

    “Shhhhh sweetheart, it’s all right.” She said calmingly “Nanny Sylvia is here and between your mother and I you will be one cared for baby girl.” 

    “But I’m not, really, I…” he tried again and the ladies just laughed.      

 “Oh but you are sissy baby Jake oh but you are. “ Sylvia said as she rubbed his shoulders. “Now time for me to show you where you will be staying from now on.” She said 

to be continued.


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