My name is John, and this is my dream. I am 18 years old, I have dressed before but never seriously, and down the street from me lives a woman named Sarah. She is the mother of a very wealthy family and just radiates control and success. Ever since I had seen her, this story has played over and over again in my mind. So here it is.

I woke up and the weather couldn't have been nicer. The sun was shining and so I decided to put on my favorite pink lace thong under my normal clothes before going for a nice morning walk. As I walked by her house I got lost in thought of her. Her long blonde hair, slim figure with ample breasts, her beautiful blue eyes and plum lips.... What else could I ask for?

Just then, a voice interrupted my day dream, and to my surprise, it was hers!

"Hey, John, I see you are up early as well!" she said while walking towards me in the tightest sports bra and booty shorts.

"Well, yes, but I see I haven't quite dressed up as well as you have."

She came close then, she reached around me and I felt her pull at my thong!

"I don't think that is completely true, now is it?"

I blushed, "I... Umm... Well..."

"Don't worry I've known for a long time. Why don't you come inside for a while?"

She took my hand and led me inside. I couldn't do anything but what she said, I was in shock.

We got inside and she brought me downstairs to a couch in the middle of an empty room.

"Now if you'll just wait here, I'll be back in a second with a little gift for you!"

She quickly ran out of the room and left me there with my head full of thoughts. 

How did she know? How long has she known? What is this gift? And before I knew it, she was back with a bag in her hand.

"This is all for you, try it on and tell me what you think!"

Inside the bag was a school girl's outfit, made up of a short pleated skirt that couldn't cover more than half of my ass, a white blouse, and of course a crimson red thong with a matching bra with huge inserts. To top it all off there was a pair of red heels that must have been at least 6in and a pair of furry handcuffs. I froze.

"I see you like it, go ahead and try them on! I have to go get changed as well. Don't take too long... Okay?"

All I could make out in reply was, "O.K."

As I undressed, I could feel my hear racing. I slipped the thong on and it covered my sissy boy clit perfectly and felt like heaven in between my cheeks. Next came the bra, it fit perfectly and once the inserts were in, I truly felt like a woman. I finished up the outfit with the blouse, skirt and heels and couldn't help but giggle at how good it all felt. I was so high on pleasure that I didn't realize that Sarah was standing in the door frame. My jaw dropped.

"Oh don't you look all pretty, you little slut. Do you like what I have put on for you?"

She was sporting a full latex jumper that had holes for her breasts so they sat in the open looking perfect. As my eyes kept looking, I saw something that made my heart skip a beat. Attached to her crotch was a 7in black dildo...

That is all for now, Let me know if I should continue this story. I'm open to all comments!