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AUTHOR’S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories first. Enjoy.
*****
HALLOWEEN
It was October and the leaves had changed color and fallen. It took me a day to rake them all up and get the yard ready for winter.
The pool was covered but Daddy and I still enjoyed the hot tub.
I packed up my cute summer clothes and Daddy bought me some really adorable winter ensembles. I even got a pair of those footie pajamas with the trap door in the back. The fleece footies were white, zippered up the front and the hood had a rainbow unicorn horn on it.
The trap door has come in handy a few times. I especially like when Daddy comes up behind me, unsnaps it and plays with my bottom before he slides his big, beautiful black cock into me. When I wear my footie I seldom wear panties underneath. If I do, I try to coordinate and wear my cotton panties with the rainbows and unicorns on them.
Halloween was fast approaching. We hung some cobwebs on the porch and lit the Jack O’Lantern every night. I couldn’t wait to pass out candy to the kiddies.
When I asked Daddy what our plans were, he told me we were going to a big party at a club owned by a friend of his.
I loved going out and got excited. Upon learning it was a Halloween costume party, I got even more excited. In case you don’t know, Halloween for sissies is like Christmas for everyone else. I mean I love Christmas too! Halloween was a chance to dress up though.
Yes. I realize I dress up every day. This was different though.
The club was called The Pink Boy and catered to men like Daddy who liked panty-boys, sissies and femboys. It was hard to imagine there were so many men and bois like me they needed a large club to hold their party. Knowing I would be partying with pretty bois in pretty panties made the whole thing even more exciting to me.
Daddy said he knew the owner and we’d have a private booth. For helping promote the club, the owner told Daddy some of our bar tab would be on the house.
Daddy promised it was going to be a wild night. I had no doubts. Any night with Daddy is wild and we didn’t even need to leave the house.
He actually had me at ‘we’re going out.”
Then Daddy told me we would be meeting another couple at the club. Lonnie was a friend he’d met the gym. Seemed Lonnie had a pretty pantyboy all his own. His boi’s name was Kylie.
Daddy showed me some photos of the two.
Yum. Kylie was a real cutie! He had a very pretty face and a killer body. It looked he had boobies and a great butt. It was hard to believe he was really a boi. Then again, I could say the same about myself.
Kylie’s daddy was a big, strong black man just like mine. I couldn’t wait to meet them both.
Then I started thinking: WHAT would I go as? WHAT would I wear? My mind was racing with possibilities.
I began looking at websites for ideas. Unfortunately I started getting all the wrong ideas. Looking at the photos of those sexy models in skimpy little costumes got me wondering how I would look dressed up as a sexy nurse, sexy superhero or a sexy barmaid.
Then I started to think about how Daddy would react to seeing my dressed as a naughty girl scout or sexy version of a Disney princess.
Thinking about Daddy got me thinking about his big, black cock and, well, thinking about that got my panties wet. I closed my eyes and reached my hand into the front of my panties and started rubbing myself. I saw myself as the sexy little devil sucking his cock, making him good and wet and hard and ready to fuck me. Then I saw myself on my back, knees by my face and biting the tip of my red, devil tail. Daddy was thrusting into me, grunting like a bear.
I had a freehand so I reached into the nightstand next to my princess bed. When Daddy walked in I had one of my toys in my bottom and was rubbing my clitty furiously.
He poked his head in my doorway, laughed and said, “I thought you were looking at costumes.”
I just smiled and say “Oopsie.”
He walked over and stood at the end of the bed. Seeing me there, naked from the waist down, pumping a toy in and out of my boipussy, my clit glazed from rubbing myself, got him hard and aching for release.
He unzipped his pants and let them fall. As he stepped out of them he slid down his boxer briefs. His erection fell out and hung heavy between his powerful legs.
Daddy grabbed my ankles and pulled me to the edge of the bed. My top slid up exposing my hard nipples. Daddy put my ankles of his broad shoulders. I reached down and pulled my toy from my bottom.
Seeing I was already slick and aching to be filled again, Daddy slipped right inside me to his balls. He picked up my toy and offered gaziantep escort it to me. I slid it past my lips and sucked on it as his balls slapped gently against my bottom. Daddy came after thrusting into me for a solid five minutes.
I don’t know how he lasted so long. He’s a beast!
After a hot shower and a snack, Daddy and I talked about Halloween again. I confided I was having a hard time deciding what to go as.
I was relieved to learn Daddy had already decided on our costumes.
“Silly sissy boy,” he said, “You know Daddy makes the decisions like that.”
He was right. He did.
I was excited to hear about what costumes he’d selected but was told I had to wait.
A whole day passed and nothing. I was dying of curiosity!
When I begged Daddy to tell me he just laughed. When I stuck my bottom lip out he told me I was cute. When I stamped my foot on the floor defiantly he told me I was seconds away from a spanking.
I almost stamped my foot again.
On the second day I devised a new strategy. I waited til I heard the shower and snuck into our master bathroom. I waited quietly for Daddy to walk out of the shower.
I was there, on my knees, wearing only blue boy short panties and a smile. He stepped out and grabbed a towel, towering over me and smiling his million dollar smile. His body glistened and his cock hung between his legs smelling fresh and clean.
I asked Daddy again what we were going as for Halloween and he smiled and he said it was going to be a surprise.
When I slid the first three inches of Daddy’s cock down my throat, my hands on his ass pulling him into me, he told me. He came first then he told me. Sissies have their ways you know.
Daddy told me we were going to the party dressed as Little Red Riding Hood and the Big Bad Wolf.
He said our costumes would be delivered in three days.
I was like a little kid waiting for Christmas. Every day I ran to the door to see if there was a truck in the driveway. Every day I’d be disappointed. One day passed. Two days passed. It was getting close to party day and still nothing.
I awoke on the third day to cool air on my bottom.
I figured my sleeping shirt had ridden up at some point during the night. I didn’t wear panties to bed. Well, not when I was going to sleep anyway. Even then they usually wound up on the other side of the room. Besides, who wants to sleep in moist panties?
I was just waking, seeing shafts of light coming through the blinds, when I felt warm breath on my bottom. Then I felt the gentlest bite on each cheek. I lie there waiting for what was to come next. Hopefully it would be me.
A warm, wet sensation tickled the line between my two round globes.
My ass was so round and bouncy now. I loved how it looked in all the panties I now wore 24/7. I loved how the weight of it swayed when I walked. Most of all I loved how Daddy loved it. He worshipped it the same way I cherished and craved the black beauty hanging between his muscular legs.
And now he was licking along my crack, sliding further down with each pass. His hands separated my cheeks and cool air rushed in between them. Suddenly there was a kiss directly on my pink pucker. It lingered there for a second. The tingling in my clit intensified. The tip of his talented tongue swirled around it.
Then the tongue slipped inside me.
Oh my.
I don’t need to tell you I started to leak out onto the bed. The tongue pushed further and I felt beard stubble rubbing against my tender inner cheeks.
Daddy could eat boipussy for hours but he had to go to work. He tongued me long enough to make me wet for him. He gathered his spit and let it pour from his mouth and onto the lips of my boipussy. Then he licked me again, pushing his natural lube into me.
Then he lifted me by the hips and slid a pillow under me. I put the tip of my thumb in my mouth. My heart was racing. I braced myself.
Daddy repositioned himself, his knees on either side of me and inched closer. The head of his cock slipped into me and with one push he was balls deep. I pushed back into his thrusts, grinding my clitty into the pillow, rubbing myself in a rhythm with the cock inside me.
I love a good fucking and that morning the fucking was very good and for a minute I forgot about Halloween, costumes, my name and what numbers came between 6 and 9.
After we showered. I swallowed Daddy’s cock and he filled my belly with the first of two protein drinks I’d have that morning. I put on some pj’s and went down to the kitchen to fix my man some steak and eggs for breakfast. I had my second protein drink (the one made in the blender this time) my special vitamins and a piece of wheat toast.
Daddy dressed and left for work. He gave me a long kiss and a playful spank before heading out the door.
As I watched him drive away a truck pulled up to the front of the house. I saw a man exiting the truck, konya escort gather four garment bags and start walking towards the front door.
I was still in my lounge around the house pajamas. I didn’t have much cleaning to do but there were two loads of laundry I needed to fold and a movie I’d been dying to watch. It was called Daddy’s Girl Now.
You can probably guess what it was about.
I was wearing pink, white and purple shortie bottoms and a matching, long-sleeved crop top which showed just a little belly.
When I answered to door the delivery driver thought he’d hit the jailbait lottery. A pretty little thing all alone in ‘her’ big house in just ‘her’ pajamas?
He asked me where I wanted the garment bags to go and I told him my DADDY wanted them hung in the back room. I also told him I liked well hung things too. I’m so bad.
The twenty something year old swallowed hard.
I walked him to the back of the house and showed them where he could hang the costumes. I could feel eyes on me as we walked through the house. Some cheek was showing from my shortie bottoms, and, as I mentioned, my walk had a definite swish to it now.
No mere mortal man can resist looking at a good butt and, all modesty aside, I had a good butt.
I stopped at one point to bend over to pick up a magazine. I heard a sharp inhale behind me. I didn’t know what to do once I had the magazine so I just carried it with me.
I think my new admirer started to wonder about me. Maybe it was my voice. Although I’d been practicing, I still had my boy voice.
I noticed he had a look on his face I’d seen before. He was trying to decide if I was a girl or a boy.
My top was tight. I don’t have boobs but my nipples and areola are more defined now. Even though I’m flat chested (as far as most girls are concerned) I do have more shape there than most boys.
My hair is short but it has a definite feminine style to it. From bellybutton up I was androgynous. From my waist down, I was all girl, save my cute little clitty, that is. Which I don’t think he could see through my bloomer-style bottoms.
I did catch him staring at my smooth legs and bouncy bottom, trying to figure me out.
The poor guy was confused but definitely enjoying the show. I flirted unabashedly and he kept his clipboard lowered over his crotch. Pantyboys like me love that kind of attention.
Being naughty I asked if he had any more packages for me. He swallowed hard and said, “Uhhh…no…Miss.” There was just a hint of a question in his tone.
He hung up the garment bags in a closet in a spare room and asked if they looked okay.
I smiled coyly and said, “Yes. Very well hung.” I couldn’t resist.
He tripped three times heading back to the front door. I signed the forms he gave me, smiled and waved to him as he drove off.
Then I ran back to look at my costume. I actually squealed and clapped my hands when I unzipped the first bag.
When I first saw my costume my heart raced and there was a stirring in my panties. It was adorable and sexy all at the same time!
It was a flirty, sissy, adult version of the classic idea of Red Riding Hood. I had seen something like it when I was looking online.
I laid out each item on the spare bed.
Oh my! The panties were scrumptious. They were scarlet red, ruffled boy-short style panties. The ruffles were black and red. I’m not sure if Red Riding Hood wore panties like that but this one was going to be.
The top was a scarlet red bustier. There was a scarlet satins skirt and three stiff petticoats. The cloud of tulle was a sharp contrast to the black and red of the rest of the costume.
The costume came with a short red cape which had a hood.
To complete my ensemble, I’d wear red thigh high stockings and black MaryJanes with a two inch heel.
I couldn’t wait to try everything on!
I slipped my hand inside the bag containing Daddy’s costume and felt fur. I couldn’t wait to see him dressed up!
That evening we had dinner, watched the movie I never got around to watching and then headed out to relax in the hot tub. Neither of us were very relaxed though. The movie was very hot. It was about a trucker who picks up a hitchhiker and over the course of two days turns him into a pretty little sissy. Before the movie even ended I was on Daddy’s lap, facing the tv and bouncing on his cock, his strong hands on my nipples.
The boi on the screen, looking and acting so girly now, was lying back in the passenger seat of his daddy’s big rig. His pretty green panties were down around his knees and his daddy’s hand was rubbing his little clitty. He moaned. I moaned. He came. I came.
Daddy came inside me a second or two later.
One fucking is never enough for my man and sitting there in the hot tub we both knew the other was thinking about the movie.
Daddy gave me the look. I slid my hand under the water and felt his hard cock kayseri escort and gave it a squeeze. We slipped into the pool house. I got onto the big couch and watched as he walked towards me, his huge cock swinging.
We lay in the 69 position and pleasured each other before Daddy couldn’t wait any longer. He got me on all fours and fucked me from behind. I love a good soak in a hot tub. Don’t you?
***************
The afternoon of the party, Daddy invited Miss Marguerite over to help me get ready. The first thing she did was fawn over my costume, telling me she couldn’t wait to see me in it. Then she ran me a hot bath.
As I soaked in a luxurious bubble bath, Miss Marguerite walked in sipping a glass of wine.
The flowery fragrance and bath salts relaxed me. We laughed and talked like old girlfriends.
Miss Marguerite asked me if I liked my costume and I squealed that I did indeed.
When I had soaked enough and my skin was baby soft and smelling sweet and girly, I stepped out of the tub.
Miss Marguerite tenderly dried me with a big, soft towel like I was a child. She commented on how smooth and soft my skin was. Then she powdered me, all over, with a big puff of talc. It smelled of baby powder and something else. I loved it and asked her where she got it. She told me I could have the bottle. And the puff!
After I was powdered, Marguerite had me bend over the end of the tub. I felt her hands on my bottom and she told me to relax. She told me Daddy had requested something special as a part of my costume for the evening.
I felt a cold, slippery finger enter me and circle around. Then I felt another. Miss Marguerite then pulled her fingers out and gently replaced them with something harder, something made of silicone.
It was a plug. A short bubblegum pink one to be exact. After it was nestled inside me, Miss Marguerite held open my first pair of panties.
The panty was brief style and had a triple pad in the crotch. It wasn’t the sexiest thing in the world. It looked like training panties and my heart sank a little. Miss Marguerite explained the pad was there to keep me from soaking my pretty panties as I partied and did other fun things.
“Sissies dressed like you’re going to be dressed,” she explained, “Often wet their panties because they felt so scrumptious and girly. With all the attention you’re going to be getting from all sorts of handsome men,” she continued, “You are going to get excited. Trust me.”
I did. Besides, I didn’t want to party in wet panties all night.
And then…oh my goodness! The next pair of panties she held open for me were the ruffled panties I’d been dying to wear since I first saw them.
They were rhumba style panties and immediately reminded me of the kind Billy was wearing that Halloween so many years earlier when I was another person.
I stepped inside the satiny panties and let Marguerite slide them up my waist. She pulled them up and over my bellybutton. Despite the first pair I was wearing, my second pair of panties did feel divine. I couldn’t resist running my fingers through all the ruffles on my butt.
Miss Marguerite said I looked like Little Miss Tuffet and when I corrected her and told her I was Little Red Riding Hood, she spanked my bottom.
Then she looked at me with an almost sad look in her eyes.
I asked her what was wrong and she nothing. After a minute, still staring at me in my frilly panties, she sighed.
“All little boys,” she said, “Should have a chance to wear panties…panties like this…with ruffles, lace and bows…at some point growing up,” she said.
Her hand rested on my bottom, playing with the five rows of lace.
“And wearing such pretty panties would certainly calm their wild spirits.”
It had certainly calmed mine.
Then she added, “Sugar and spice and all kinds of nice, you know.”
She blew a kiss on my belly and I laughed.
Then I got serious and told her about Billy and how he had dressed as a pretty little girl for Halloween.
“Did he look pretty?” she asked.
“Yes,” I said, remembering him spinning in his party dress with its lacy pinafore, flashing his rhumba panties, “He looked like a fairy princess.”
As she fussed with the ruffles on my panties, she asked, “And how did that make you feel, Precious?”
She always called me Precious, or Baby or Baby Gurl.
“I made him cry. I told him I didn’t want to go trick or treating with him because he was dressed like a girl.”
“Oh, my, that wasn’t nice,” Miss Marguerite said, giving me a gentle slap on my thigh.
“I know. I felt horrible about it.”
“What was the real reason you didn’t want to go though, Baby Gurl?”she asked, spinning me so we were eye to eye, almost.
“I was jealous. I hated that he had on such a pretty princess dress and panties and shiny black buckle shoes and I was dressed as a dumb vampire.”
“See? You were a sissy even back then. Did you ever get to dress?”
“Once,” I said, “Later on. Billy and I had made up and he invited me over for a sleepover. I saw the dress in a closet. He asked if I wanted to put it on and I said ‘yes.’ He put the whole outfit on me. His two older sisters even helped. They dressed us both up, did our hair and even put makeup on us.”
“How did you look?”
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