Pleasing Bill: A Crossdressing Story #2

“That’s what i like to hear. Now at 12AM tomorrow i want you to be at our house dressed up in the sexiest outfit that you can get your hands on. I’ll text you our address.”
“I can’t. My family are still at home by 12.” I pleaded.
“That’s not my concern. Now this is your first task i’m telling you to do. Are you going to fail me already? Because you be here at 12 o’clock on the dot or you can forget about ever seeing me again.” Bill said annoyed.
I couldn’t disappoint him. I need to prove i’m going to worth his time.
“I understand, Sir. I will be there.”
“That’s a good little whore. See you then.” He hung up. How the hell am i going to get out of here ,dressed up like a slut, and be there at 12? I kept some of my sister’s clothes she was going to give away, and didn’t notice were missing, in my room. So i know what i am going to wear but how do i leave the house with anyone seeing me. I never even left my house dressed like a whore. I can leave before they wake up but i’ll have to kill time before i get to Bill’s.
I went to sleep with my alarm set to 9AM knowing my family is a bunch of late sleepers and wouldn’t be up until 10 or 11. I should be able to leave without notice.

The next morning i was up and dressed with in 10 minutes of waking up. For the outfit i decided that a black short skirt with a white shoulder length top. I Put on the only girly shoes i had and applied some extra make up than normal. I decided to use the same wig from yesterday hoping Bill liked it and would want to see me in it again. I wasn’t sure he even knew i was wearing one. After i was satisfied with my appearance, i put my ear up against my bedroom door to listen for any activity from my family.

I was positive i didn’t hear anything and slowly opened my door. I was so nervous i was shaking. It felt taboo walking in my house like this and i could feel myself rock hard under my skirt. I made my way down the stairs and to the garage door, where i parked my car, i was about to open it when. I heard someone opening my parents door across the room behind me. Quicker than any door i had ever open, i was in and out in a flash. I hit the button to open the garage door and ran to get into my car. My heart was racing as I started the ignition and pulled out and drove out of my driveway fast as i could. I made it, i couldn’t believe i made it. Once i was out of the neighborhood i lived in, i heard my phone was ringing from the purse i brought with me. An old one my sister was going to get rid of before i snached it. I looked to see my Dad calling me. I’m sure he was just calling to see where i went. There is no way he saw me so just calm down I told myself.
“Hello?” i answered his call sounding calm as possible.
“Jacob? Did you just leave through the garage?” He asked
“Uh yeah. I’m going down to get breakfast with a friend this morning. I told you about it last night.” I said acting causally as possible.
“Yeah now i remember. I just swear i thought i saw your sister leave through the garage door.”
Shit, he must of barely saw me. Just play it cool i kept telling myself while also trying to concentrate on the road.
“No? It was just me. Were you wearing your glasses?” I asked
“No. Anyway have fun. When will you get back.”
“Probably not till later tonight. I gotta go. Bye.” i said trying to get back to driving. He hung up and a wave of relief washed upon me. Now that i was free i need to kill some time before i get to Bill’s.

2 1/2 later

I arrived at Bill’s a few minutes before 12. House wasn’t far from mine. It was alot smaller then my parents house but it still looked nice. One floor with maybe a basement. I hadn’t gotten out of my car since i left i. I drove to a parking lot in front of a old department store that was going out of business and waited while browsing my phone. It was weird to be out in public looking this was. It took me awhile for my bonnar to go down but anytime i stop to think about what i’m doing i almost immediately felt my panties got tighter. I parked on the side of the road in front of his house and got out. My heart was racing again as i forced myself to act casual and walk up to the front door. I rang the doorbell and wait what felt like an eternity. Jake answered the door.
“Hey there. Come on in.” He said with a grin.
I walked in the front door to their living room that was decorated well with a couch dair and a flat screen TV. The kitchen was off to the right with dinning table on tiled floor.
“Hey dad, he’s here!” Jake called down the hallway. Moments later Bill walked up stairs leading from a basement to great me.
“You’re right on time and you look good too. You passed the test.” Bill said. It felt nice but i was confused about how easy it was.
“That was the test? I thought yesterday would have been the test.”
“No. Yesterday was us having fun. Now i got something for you to where today. Follow me” Bill commanded. I did even though i was a little disappointed that i wouldn’t be wearing what i came here wearing after picking it out last night. I entered a bedroom i assumed was his and there was a silver and black corset with ruffle pants panty hose and garter belt. A pair of black high heels were on the floor next to them.
“Now but this on and then start making us some lunch. Me and the boy haven’t eaten yet.” Bill told me.
“Yes Sir” i responded
“No. Now that i know you’re committed you are going to call me daddy from now on. Got it?”
“Yes daddy” I said and smiled. I’m calling him daddy now that makes this so much better.
“Good slut.” He said and left the room. I changed outfits and left my old stuff on the bed. Along with my purse with my change of boy clothes. After i was done i walked to the living room where the were waiting while watching tv.
“Wow, you look fucking good.” Jake said staring at my body.
“Thank you” I said with a grin, Bill got up with something in his hand.
“Now you’re almost done. Put this collar on and i’m going to lock it into place.” He held up a black and pink collar with a lock on the back and a chain lick on the front. In pick it said Daddy’s Slut on it.
“Oh ok. Why the collar, daddy?” i asked wondering what the point of it was.
“ Because i want you to remember that you’re owned by me and you remember what you are.” He said locking the collar into place. It was tight enough to be firm but not enough to discomfort me. After i had the collar on i looked through their kitchen looking for something to make. I ended up making them mac and cheese. They ate in the living room while chatting and watching TV. I cleaned the kitchen and started a load of their landry and was getting ready to put another one in the wash when i heard them call me; or what i was known by.
“Hey, Slut!” Bill yelled. I quickly made my way to the living room.
“Yes?” i said as i turned the corner. I saw Jake with his cock out lightly jerking himself and Bill getting ready to leave.
“I’m going out to run a few arends. Got a few things i need to pick up for you. Stay here with Jake untill i get back.”
As soon as Bill left i felt Jake pull me down to the small couch where he was sitting. He started to touch my thighs by rubbing them then massaging my ass through my short pants. I was getting ready to lean over his lap to suck his cock when he stopped me and pulled me into a passionate kiss.

Neither of them kissed me yesterday, i assumed that they preferred to use my mouth for pleasure then passion. I sat in Jake’s lap vigorously making out with him while our tongues battled for dominance but he started to pull at my ruffle panties and work them down to my ankles. He moved away from my mouth and stripped down. I didn’t notice it yesterday but Jake’s body was magnificent. He had clearly had the body of an athlete even though Bill had the body off a retired one. He knelt down infront of me and began to eat out my ass. I had never felt anything like this before. He pushed and pulled his tongue in me until i was dripping from my hole. He then positioned himself on top of me missionary style with my legs in the air. He looked down at me and gave me another kiss, this one much shorter, then positioned himself in me and began to push his way in.

I moaned out as he put his whole cock inside me. He let it rest in me a while and began to kiss me again. I loved having this passionate sex , it was so much more personal this way and he was doing everything to pleasure me instead of himself. He began to start thrusting into me as we stopped kissing. He almost pulled his entire cock out before he quickly thrusted back into me.
“Ohhhh fuck yes! Fuck me harder!” I moaned out without being able to control myself.

Jake started fucking my ass full force making loud claps go through the house. After a few minutes of Jake fucking my boipussy and me screaming and moaning from it, Jake moaned out that he was about to cum.
“Cum in me baby!” I yelled. Soon after i felt hot warm liquid start to fill my insides. Jake pulled out of me and climbed over me to put his softening cock out in front of me. I realized he wanted to go for round 2 and needed me to get him ready. I eagerly started to suck him and clean up the remaining cum. I could even taste my ass on the shaft of his cock. While he began to grow hard again in my mouth, i began to feel his cum leaking out of my gaping ass.
He was hard again in a few moments and moved back to fuck me in the same position as before, except there was a small pool of cum around where my asshole was sitting. Jake didn’t even seem to notice as he thrust hard back into me causing me to scream out again in pain and pleasure. He was fucking me using his cum from before as lube. Jake began to stroke my hard small cock with one of his free hands which caused me to moan out so loud i was afraid the neighbors might hear us.
“Fuck, Jake! I’m going to fucking cum!” I yelled loudly while he continued to pleasure me. I lasted just a minute before i shot my cum all over my corset and Jake’s chest. Jake continued to fuck me while my limp dick was resting on me. I was motionless, in a trance, after the incredible orgasm that left me temporarily brain dead. He shot a second load in me filling me up even more than i thought i could have been. He pulled out of me and embraced me in one last kiss. He got up to leave for a moment and i fell asleep from exhaustion.
I woke later to the sound of Bill coming in the front door.
“Well it looks like you two were busy.” Bill said. I got up and put on my ruffle pants not sure what to say.
“So what’s for dinner?” Bill asked
“Uhh i haven’t planned out anything yet” i said cautiously
“If Jake needs to fuck you, then let him fuck you. But you’re also supposed to be doing the cooking and cleaning in this house! Now you better get started!” Bill yelled angrily. I turned to walk towards the kitchen as Bill slapped my ass hard causing me to yelp. I saw it left a large red handprint that was their the rest of the day. I cooked generic hamburger helper while Bill sternly talk to Jake about something out of earshot. They went to the guest bedroom with the stuff Bill got to set something up for later. When i was finished with dinner they came into eat.
“Good girl. Me and the boy are going to eat on the couch but since you decided to sleep most of the day away you can eat on the floor.”
“I’m sorry daddy. I won’t fall asleep while i’m here again.” I said trying to sooth Bill’s anger towards me.
“No you won’t. Now let’s eat.” Bill sat with Jake on the couch and i started to sit cross legged on the floor with my plate.
“Excuse me but that’s not what i meant! When i said eat on the floor i meant you put your food in a fucking dish and eat it on your hands and knees.” Bill yelled with a grin.
“Yes daddy. I’m sorry daddy” i said as i got a dog dish Bill had left out. I put my food in the bowl and placed it on the floor.
“Not yet! Let me fix that.” Bill said. He took the bowl and with a black marker wrote DUMB SLUT across the bowl.
“Now you may eat.” Bill said as he put the dish on the floor. He was standing above me as I was on my hands and knees trying to eat the food i cooked. Bill sat down with Jake and started to eat too.
“Good girl. Isn’t she just a dipshit huh, Jake?” Bill asked. I looked over to Jake and could tell this was upsetting him. It hit me that Bill was doing this to me because of Jake, not my own actions. Jake might have grown attached to me and Bill was trying to remind him i was their whrore.
“Yeah she is dad.” Jake murmured.
“Thats right she is.” Bill said. We finished our meals and when i was done i gathered the dishes and cleaned up dinner. It was getting close to 9 and Bill motioned for me to come over when i was done.
“Now J. Your first day here is up. I want you to stripp off your out fit but leave your wig on.”
I did as Bill said and put the clothes in the laundry room. I went to get my purse that had my other
change of clothes in it but couldn’t seem to find it.
“What are you looking for” Jake asked
“ My purse. It had my other clothes in it” I said
“Oh you won’t be needin those. You’re going to keep them here and i threw out those boy’s clothes you brought” Bill said looking hard faced.
“Wh-why?” i asked as panic shot through me.
“I don’t want you bringing boy’s clothes here with you. I never want to see you in your boy clothes.”

“But how am i going to get home? I needed those to walk in the front door.” i pleaded
“ That’s not my concern. Now go on and head home. Be here the same time tomorrow” Bill said and pointed at the door.
“But i can’t go home yet i still have the collar on and i completly naked!”
“I don’t want you to take off the collar and you don’t get to go home dressed for bring your boy clothes to my house.” Bill was punishing me for my mistakes today and i could tell it was getting him off because of the hard long shape in his pants. I accepted my fate and walked to the door where Bill opened it for me.
“See you tomorrow, daddy’s little slut.” Bill said as he closed the door.

I was completely naked when i walked out the door. It was dark out and the neighborhood that they lived in seemed to be quiet. I was shivering as i made my short walk across their lawn to my car. When I was safe in my car i began to drive my way home. On my drive home i was extra careful to take the back roads home to avoid as much traffic as possible. I pulled into my driveway with my lights off and parked outside the garage. I had to get into my house without being seen, which makes this morning seem easy by comparison. My best bet was to use the key hidden under a rock to go through the front door instead of the garage where i was sure to be seen and heard. I made my naked ass to the front door, while shivering on the way there from the night air. I got the key and looked through the window and saw nobody in the main hall or near the stairs. I tried my best to open the door as quietly as possible. I walked to the stairs, where my room was located above, while my heart pounded through my chest as i heard someone call out
“Whose home?” It was my mom’s voice. I called back
“It’s me. Just got back from a friend’s house.” I made my way up the stairs trying to not sound suspicious.
“ You’ve been gone al-” my mom stopped as she rounded the corner and saw her son completely naked wearing make up, a blonde wig, and a collar that said Daddy’s Slut on it. I was frozen in fear and felt like i was about to throw up. Her eyes were wide open and she stared at me for what felt like forever. She eventually said
“Uhh honey, next time you go out tell us what time you’ll be back.” she said sounding like she could barely find words for what to say. I nodded Then she replied
“And please feel free to talk about your…new friends to me if you want. Now get to bed.” she said as she slowly walked towards my parents bedroom. I heard my Dad ask who was it. She covered for me by saying that i was tired and had been hanging out with friends. My mom knew. She knew i was a crossdresser. She actually was okay with it and even covered for me. My legs were shaking as i made my way to my room to shower and clean myself up. I still had the collar on when i got into bed. I was, exhausted and shocked from this long day. My mom knowing would make things alot easier with Bill….