Aunt Mary's Dress Shoppe Pt. 02

What A thrilling time I was having at Aunt Mary's place. On my very first day she caught me wearing a maids dress while pretending to suck off one of her sewing dummies and for my trouble, I got her strapon straight up my ass. I also got to wear any dress she had laying around that seemed to fit me as well as any other female clothing.

I was in a wonderland I hardly even knew existed.

I worked for Aunt Mary cleaning up her house and attached dress shoppe (They were one and the same) doing house chores and boxing up the multitude of girly things she had just laying around. I got to pick out and keep what I liked.

And of coarse my aunt took a keen interest in my bottom, especially when it was pantied. I did have my own clothes but as the first week wore on I found myself more and more in some sort of dress, either because I wanted to or at Aunt Mary's suggestion.

The very act of working in a dress doing house work made my little dick/clit hard all the time. That usually led to Aunt Mary plowing my ass with one of her strapons. She had increased the size once and the sensation was almost electric.

It was on about the tenth day after I had arrived when I got my first taste of a real cock. I had rather easily fallen into a nice routine of getting up and immediately putting on whatever dress Aunt Mary had laid out for me. Then after breakfast I did the dishes and began to do house chores. I had chosen to hide when one of her customers came in and she seemed not to mind this.

Until now.

"Oh Cammy dear, can you come down here sweetie?" she yelled up the stairs.

It wasn't at all unusual for her to summon me for some chore but this was the first time she did when she had company. I went downstairs to see what she needed when I suddenly came face to face with a man in his thirties. With him was another man in his early twenties.

"Oh Cammy dear, Mr Blanchard here wants to buy a pretty gown for his friend here but wants to see what it looks like before commiting. I have one that might fit you, would you be a dear and try it on for them?" she asked me handing me the gown. It was white and could easily be taken for a wedding gown.

"Sure." I said taking the gown from her and heading up to my room to change when she said, "Oh no need for that, you can change right here. Mr Blanchard can help with the buttons in the back."

I was embarrassed but excited as well so I carefully took off the pink ballerina's dress I had been wearing and pulled the gown over my head allowing the skirts to fall all over my body. The dress was just a tad bit big for me and walking proved quite difficult. Most of the dresses my aunt had me wear were short things that showed off my panties, but not this one. It came down to the floor and some.

"Here dear, try putting thes one while Mr Blanchard does you up." she said handing me a pair of four inch heels to step into. To my surprise, the shoes fit and by the time I was all done up, it fit nice except the skirt was way to full.

"The skirt is in the way of everything." I complained.

"I've got just the thing for that. Here, step into this sweetie." she said holding what I knew to be a hoop skirt. Right away I fell in love with the whole outfit. The way the hoop skirt held out the skirts and allowed me to move and swish around. I was in heaven even though I was being watched by a man.

"Well princess, would you like to get married in something like that?" Mr Blanchard said to the younger man with him.

"It's so pretty. I could get married in that but can you buy me one in pink to play in too?" the younger man asked.

"Sure, we'll call it a wedding present." Mr Blanchard said.

"Excellent, now I have to go and order some more fabric if you want two dresses. Why dont I leave you to get acquainted with my niece here. Her name is Cammy." she said and then to me, "Sweetheart, why don't you show them to your room so they can see what it looks like in a bedroom?"

I knew right then and there that my aunt wanted me to have sex with one of them. We had talked about what a real man would be like when she pegged me and now here it was.

Delicately, ever so delicately, I managed to walk up the stairs in the wonderful bridal gown and led the two men into my bedroom for what I hoped would be my deflowering.

Yes I know, a week and a half in a dress regularly getting pegged in the ass is making me a total sissy but so what. Aunt Mary always says better to be happy and I was for the first time in my life, happy.

I walked into my room and was worried when both men saw some of the sewing forms wearing strapons I had been using to practice on.

"Perhaps you'd like to see how the dress looks on me when I am in bed?" I said suggestively.

"Yeah, we'd like that." the younger one, the one who was to be the bride, said.

I carefully managed my skirts and got up on the bed and then laid back and said, "Want a closer look?"

I was practically whoring myself but I wanted it bad even though I had no real idea what it would be like other than the peggings I got from Aunt Mary.

The dominant one stripped naked and got on the bed and I instinctively spread my legs for him in an open invitation.

"Are you ready to see what I'm gonna do to you on our wedding night princess?" Mr Blanchard asked his friend.

"Yes, daddy, show me please." the kid responded.

He grabbed my legs and quite brutally ripped my panties down and in one solid thrust, plowed inside me balls deep.

"Ahhhhhhhh, Help, your too big. Oh fuck it hurts. Please stop." I screamed and even as I did, my own clitty betrayed me by bursting forth with a gush of cum into my skirts ruining the dress.

"Damn sissy that's a tight pussy you have there." he said as the pain of the initial violation subsided.

On my back with him holding my legs up with my panties around my ankles he proceeded to fuck me hard and soon I was rocking in tune with him. He fucked me while his so called fiance watched.

"Damn girl, if you ever wanna make some money, I know lots of guys willing to pay for a sweet whore like you." He said as his sperm left his manhood to swim around my insides.

When he was done he dismounted and before they both left, I asked, "What about him." The only answer I got was when Mr Blanchard pulled the younger man's pants and panties down showing me he was wearing a chastity cage.

"Bummer." I said as they left leaving me on my bed.

After a little time to get over the feeling of getting my first cock up my ass, I got myself together and gingerly walked back downstairs being careful not to trip in the high heels and massive skirts.

"Well, how was it?" my aunt asked.

"Wonderful but a little brutal at the beginning. He called me a sissy and said I could make a lot of money as a whore. I'm afraid I ruined another dress." I said.

"No matter, that was an older one and it was used so I could never sell it anyway." she replied.

"Aunt Mary, can I really be a sissy whore?" I asked sincerely considering the possibility of making money by getting fucked.

"Your well on your way but a whore and a sissy are two very different things. You are already a maid and a good one and were a crossdresser till you had sex and became officially gay which makes you a drag queen and anybody can be a whore by selling themselves but a sissy, that's a different matter entirely." she explained.

"What do you mean?" I asked genuinely confused and added, "I thought wearing a pretty dress all day made me a sissy."

"Not even close dear, a sissy is neither a man or a woman but like I said, something else entirely. You see a sissy is property not a person. All sissies are happy being sissies but none are ever allowed to be independant. Many sissies are kept in servitude their entire lives, made to wear a dress all the time no matter what, have sex when they're told, not when they want to and many are even kept diapered all the time to prove they are useless at anything but as a sex toy. But in exchange for being a sissy they are coddled and pampered their entire lives wanting nothing except to please her master or mistress." She explained.

"Can I be a sissy and whore at the same time?" I asked excited by the prospect of being coddled and pampered all my life.

"It's possible but you would need to find a master you trust because you will almost certainly be kept in bondage for a long time to make sure you do not escape." she said.

"Well, couldn't I stay here as your sissy and you could sell me as a whore. I'd still be able to do housework." I offered.

"Are you sure? A sissy is property like I said and I would own you. I might even sell you to someone down the line and there would be nothing you could do about it." she asked.

I like sissy things and I like you and the way you treat me and I love getting fucked.

"We'll see dear. For now I need a few things from the store. Take the car and pick up my order from Joann-Fabrics. It should be ready by now." she asked.

"Okay, just give me a few minutes to get dressed and I'll go. Should I do anything else while I'm out." I asked.

"No dear, you dont understand. Go dressed as you are. Sissies always do as they are told and live for their mistresses." she said.

Maybe I was moving a bit too fast. Getting fucked in my ass had been a thrill but...

I decided to go.