Sissy Son Taken to Costume Party

I was making my way to my moms and dads house to house sit for them as they were going to a party that night and I had agreed to be there to watch the house and hand out candy. I was going to be alone in the house. I loved being all alone as it gave me a chance to partake in my fetish of dressing up in girls clothes. My sister still lived there and she had some of the best lingerie anyone could ask for. So I gladly accepted watching the house almost as soon as mom asked me to over the phone last week.

I made sure to grab an overnight bag as mom said I could sleep there and head home in the morning. My old room had been converted into an office for my dad so they said I could just sleep in my sister's room as she would be out as well and wasn't expected back for a couple days.

I knocked and was greeted by my dad and we went in. Dad showed me the candy bowl which was more than half gone and asked how I was doing and how my job was going. I told it is the usual bump and grind and mom came into the hallway and hugged me and asked if I had everything and would be ok. I said I was all set and that their costumes looked great.

Mom and Dad were going to a costume party so mom was dressed as a French maid and dad was dressed like a pirate. Mom skirt was pretty short and when she bent over to pick up her feather duster I saw a glimpse of her black satin panties. I had always tried to get a glimpse of her panties while growing up as I loved the way women looked in panties.

Mom and dad said their goodbyes and they grabbed their coats and headed out the door. I watched them get into their car and head off. I grabbed the candy bowl and stole a piece or two and plopped in front of the TV waiting for anyone to come to the door. It was kind of late so traffic was slow so I gave up and headed to my sisters room. I immediately stripped and headed to her dresser.

Inside I found some new panties as well as some I had seen before. I picked up a black and white pinstriped pair and looked in her other drawer for the bra. I and my sister were roughly the same size so most of her stuff fit me. I found the matching bra and threw them on the bed. I went to her closet and found an outfit that I had been itching to wear. The outfit is better seen rather than talked about so here it is.

My sister had worn it last year for Halloween and I only knew because I had seen it a few days before Halloween last year while visiting. My sister wanted to fix her computer and I found the outfit laying on the other side of her bed still in its original packaging. I grabbed it off one of her hangers and threw it the bed as well. I found the wig along with the stockings in a bag and the heels in a box on a shelf as well. I grabbed my bag and headed to the bathroom where I shaved and showered making sure to apply a mix of baby oil and a cherry scented lotion to my skin.

I dried off and headed back to my sisters bedroom. I plugged in my iPod and started playing Britney Spears' "oops I did it again" I pulled the satin panties up and felt the exhilaration as they wrapped my butt and penis in their smooth embrace. I wrapped the bra around my waist backwards as I had seen women do before and turn it around and the straps over my shoulders.

Then I pulled the stocking up my legs. I grabbed the top of the costume and pulled that over my head and on. I grabbed some fake tits I had brought with me and inserted them into the cups. I grabbed the skirt and pulled that on along with the ruffled petticoat. I slipped my feet into the heels and started walking around.

I hadn't heard a car drove up so when the door opened and my mom stepped in I was in near shock. I couldn't say anything but mom with a surprise said what are you doing? I stuttered out a sorry and my mom's face softened and I thought I even saw a devilish smile start to appear. "Well then since you like to dress up I think you should come with us to the party. Let's fix the wig and do your makeup."

I was starting to calm down but still couldn't speak very well and just stood there. Mom told me to sit and the table while she went to talk with dad. A new fear gripped me as I sat at the table. I feared what dad would say and I just waited as Britney's song started again, barely registering with me.

Mom walked back in and said dad is waiting downstairs for his girls. She said that she had forgotten the head piece to her costume and they had come back to get it. She applied the wig and put some makeup on and I could start to see that I was looking more girly then I ever thought I could be. Mom told me to stand up and come down to her bedroom.

She had me come in and she grabbed something from her nightstand. She told me to turn around and bend over and lift my skirt up. I hesitated and she said "honey don't worry I just need to get you more ready for the party."

She unveiled the butt plug which she had grabbed and told me that this party was an adult sex party and that I would be expected to be a good girl and obey mommy and daddy. She asked me if I had ever stuck anything in my bum before and I said that I hadn't. She said that I needed to be ready to take a cock in my bum. She said this would help loosen it up so it wouldn't hurt.

I grabbed my skirt and pulled it up to reveal my cock was rising even though I was still very nervous. I turned around and bent over the bed. Mom grabbed the butt plug and applied some lube to it and then pulled my panties to the side while telling me to just relax and push out like as if I was going to the bathroom. She placed it at the entrance and teased my butthole with it for a minute and then started to push it in slowly telling me to just relax and let it in. It finally got passed what she told me was my O ring and kept pushing till it was all the way in. I felt some pain but was mostly filled with sexual excitement to finally be seen and apparently accepted.

My mom pulled my panties back with a light swat to my butt. I was taken aback by this but stood up and smoothed down my skirt. She told me the panties would help hold it in but that I may have to clench some as my bum starts to get looser. "Now let's go down and meet your dad."

I was very nervous but mom assured me dad wouldn't be mad. We descended the stairs and saw my dad waiting in the foyer. He had a smile and said that I was very pretty. He came up and gave me a kiss on the lips which made me shudder as he wrapped his arms around me. He hugged me and let his hand slide down to cup my ass. Mom told me to let him see my panties so I hiked up my skirt as he backed up to take a look. "Well, well, someone is getting very excited in her pretty panties. But we have to get going so let's get in the car.

We made our way to the still running car grabbing my coat on the way out. I saw a figure in the backset and as we got closer and to my surprise I saw that it was my sister. I got in the back and my sister spoke up "Hi sis you look very pretty."

"What are you doing here I thought you were going to a party?"

"Well sis I am just that it is the same one you are going to."

"I didn't see you when I got here?"

"I was already hiding in the car with my head down so that you wouldn't see me or what I was wearing. But I do love what you are wearing."

"You mean you're not mad at me?"

"No silly I was just shocked when dad told me and was just waiting here with excitement to see what you were going to be wearing. And you wear just as well as I did last year."

I blushed and told her thank you. Dad as dad got going he told my sister that I was getting excited and need to be calmed down. My sister seemed to know exactly what to do as she grabbed my skirt and lifted it up and released my cock by sliding the panties to the side. She lowered her head and she took my penis into her mouth before I could even say anything. "Um uhhhh, what are you doing sis."

Mom spoke up and told me to just go with it as we don't want you tenting your panties when we get to the party. She swirled her tongue around my dick and all I could do was moan. She seemed to be an expert at this as I was in heaven. It didn't take long as I exploded into her mouth. She managed to not let any spill out as she took her mouth off my dick and came up to kiss me. I let my lips part and she pushed my cum into my mouth.

I was a bit shocked but with everything that had gone on so far I just went with it and accepted it. My mom told me to swallow and I did, as my sister went back to clean up down there and pull my panties back into place.

My mom went on to tell me to remember that as I was expected to be a good girl and would be giving some blowjobs at the party and she wanted me to be as good as possible at it. We continued on and my sister kept giving me tips on how to give a bj and other things. My anticipation grew as we drove.

To be continued...