My first assignment

[shyoldguy]

My mistress has ordered me to write about my cross-dressing. I decided the best way to do this is to start at the beginning of my experiences and bring you up to my current predicament. When I was a youngster, I was the oldest child in a home with three women - my mom and 2 younger sisters. My dad was busy working and going to school and most of the time so contact with him was mostly for discipline, brought about by devious sisters who constantly plotted ways to get me punished.
At some point I must have figured that if I wore their clothes, they would accept me as a 'sister' and the punishments would stop. I was wrong, it got worse. When I was home, alone, I would take their clothes from the laundry basket and try them on. A first it was just a pair of Mom's panties, what I didn't expect was how they felt. So soft and silky, I had a difficult time taking them off, I liked it.
It wasn't long before I graduated to sneaking into my mom's and sister's panty drawers almost on a daily basis. I'd guess I kept doing this for a year or so and was always careful to leave the drawers exactly as I found them when I put their panties back. Then I began to try on other garments. The bra was tricky and I almost got caught a couple of times when I couldn't undo the clasp. During those early times I hadn't figured out it's best to fasten it in front and then turn it around and put your arms in. I was always reaching around behind, after I had my arms in - not easy to do when your just learning. Add to that your standing in your sister bedroom with her bra and panties on. Inevitably it happened. I'm standing there and I hear the backdoor slam shut. I had no choice, I grabbed my clothes and ran to my room, locked the door behind me, I can still remember talking to myself 'fuck, fuck, fucking bra won't unclip fuck fuck...' I gave up and put my pants and a t-shirt on. Still trying to get the bra off, and there's a knock on the door - my sister's voice. "You better open this door or I'm telling Dad you were messing around in my room". That wasn't an idle threat, and I didn't want the dreaded 'Dad punishment'. I'll skip the brother sister banter and go right to the money shot. "Are you wearing my bra? Take it off. right now you asshole." She was pulling on the bra through the t-shirt. What could I do, "I took off the t-shirt and turned around "I can't get the clasp to open, help me get it off!" That's when she started to laugh. "You know you’re going to whatever I say from now on, right? Otherwise Dad and everyone you know are gonna find out about this"
I sighed "yes. yes. Just get this bra off of me! I'll do whatever you want".
That was the beginning of 10 years of doing errands for her and a lot of 'dress up' as she called it. Eventually I had bought a closet full of clothes for her and what seemed like a matching everything for me, in my size, conveniently stored in her closet.
Fast forward to this year, it's my first year away from home - far away, she's in California and I'm in school in Boston. My first week at school I get a call from my sister. No how's it going, nothing like that, just "Put on what I packed for you and send me a picture when your dressed." Luckily, my roommate hadn't been assigned yet and I had the entire room to myself.
I locked the dorm door and took out the black lace corset w/garter straps, stocking, matching panties, and of course a bra, that my sister had so thoughtfully packed for me, and put them on. Click - and the picture was done, another click, and it was sent. The message I got in return "Good girl! BTW, you'll be getting a message from a friend of mine that lives in Boston. I met her in a chat room a while ago and she agreed to keep an eye on you for me. Just so you know, I sent her your picture. Have fun at school! I'll be reading all about it, I bet.".
I read that and knew this was going to be an interesting school year. I took off my 'dress up' clothes and hid them under the t-shirts in my drawer. A few minutes passed and my phone beeped - subject: 'Your sister asked me to look after you'.
I opened the text and a hot looking woman's picture appeared. She looked about the same age as me but said she was 3 years older. It didn't take long but I agreed to meet her at a local coffee shop. That's where she showed my ‘dress up’ picture and told me what was going to happen. I was now her 'boy toy' and would be given assignments which I must complete. If I didn't there would be punishments that I wouldn't like. My first assignment was to write this story and send it to her. She would then get it on the Web someplace and depending on what or if people commented on it - tell me what my next assignment would be.
Now I'm somewhat excited, worried, and waiting.

Note: I'm posting this as a favor to a friend - she assures me there will be more.