Pleasing Bill: A Crossdressing Story #1

One very long boring day in the middle of summer, i was home all alone, my parents were at work and my siblings out somewhere. I decided it would be a good day to dress up and have fun while i was home alone. I went to my secret stash of clothes i keep in my closet and picked out my purple lingerie. It consisted of a purple and black lace bra with matching thong and garter belt with black stockings. I put it on then went to get my cute blonde shoulder length wig, it fitted nicely as i applied my make up.

Once i looked like a sexy girly slut i went to go and take some of my sisters perfume and spray some on myself, i always loved smelling like a girl along with looking like one. When i was in my sister’s room i used her best perfume and even used some of her good make up. I was looking at myself in the mirror when i heard the front door open.

I freaked out because no one was supposed to be home, quickly, i locked my sisters room and listened at the door. It sounded like two men with some kind of equipment, they were acting like they were supposed to be here. I quickly texted my dad to see if anyone was supposed to be here. After what felt like the longest minute of my life he replied and said that they were here to work on painting the walls of my parent’s room. I was relieved but also still scared because i couldn’t get to my room to change back into my clothes, and i couldn’t stay in the room because my family would be home and find me like this. I had left my boy clothes in my room, I had no choice but to put on my sister’s clothes and makeup to look as passable as possible, so they wouldn’t notice i was cross dressing and say something to my parents. Once i had put on a blue sundress, and enough makeup so my own mother wouldn’t recognize me, i opened the door to walk to my room, which was downstairs and wait there until they left. I got down the stairs when they noticed me.
There were two of them and it looked like one was in his early 20’s and the other one in his 50’s. They sounded like they were from a rural area and possibly from out of state. Both were wearing painting jumpsuits with many years of use.
“Wow! We didn’t know anyone was home, especially someone as sexy as you.” one of them said.
“Sorry, i was in my sister’s room looking for my phone charger.” I tried to say in my best feminine voice. I made my way down the stairs to my room and could feel them looking at me as ii descended. They could tell i was walking towards my bedroom door when one of them blocked my path.
“Hey, no need to get in a rush, baby. You can stay and chat for awhile, we rarely get a hot young girl to chat with.” The oldest one said. I backed up and sat down next to my parents bedroom doorframe, where they were setting up to paint it. The younger one kept by the door frame while the older planted himself next to me.

“So how old are you, darling? 16? 17?” The older man asked. I wasn’t sure why it mattered so i answer honestly.
“I’m 18 actually.” I replied. I was so nervous I had to keep my arms from shaking. I just wanted to go but the younger of the two moved in front of me.
“18 huh? Must of got yourself a boyfriend right?” the younger man asked. I noticed the older man had placed his arm around my shoulder.
“No, not at the moment.” I replied realizing they had taken a fancy to me. I must have done my job too well by passing for a girl. I knew they wanted something but i can’t let them mention anything to my parents.
“Well that doesn’t seem right, someone as beautiful as yourself not having a man to please. You know we’ve got plenty of time before we have to get to work on the walls.” The younger one said.
“Maybe we can get to work on you?”

“Sorry but i can’t do this! I need to leave!” I yelled as I started to push myself off of the couch. The man in front of me forcefully but not violently push me back down be i could get up.
“We’ve spent plenty of time with woman who were home while we worked and they all loved it. So do yourself a favor and relax. Jake, help me make the young lady comfortable.” The older man said as he started rubbing my thigh. Jake, the younger man, got down and began massaging my shoulders and back. I couldn’t do anything to stop them but i didn’t want to. I was getting so turned on but i can’t let them see my cock. After a minute of escalating sexual tension, the older man by the name of Bill, stopped touching me and took off his painter’s suit with his underwear untill he was naked with a hard 8 inch cock in front of me.
“The look on your face. You’re a virgin aren’t you?” Bill said as he sat back down. I couldn’t stop staring at it. I’ve never seen one in person before.
“Yes. I never done anything like this” I said.
Well get off the couch and let Jake sit then you can learn a few things.” I did what he said not wanting to disobey such a strong man. Jake sat with His cock out and it was thinner but longer than the other one. It must have been around 9 inches. I felt bad about mine not being even half of his.

“Now undress for us. Down to your panties.” He commanded.
“But-” I tried to say no, knowing they would see my cock if i did.
“No buts!. Now undress.” He said sternly. I had to. I wanted to. I pulled the dress off me over my head when they reacted.
“Well now this changes things. We have ourselves a sissy boy.” Jake said. I had a hard on easily visible through my lacy purple panties.
“Please don’t say anything to my family. They don’t know and would hate me if they did.” Begged still sounding like a girl.
“We won’t but you better please us because if you don’t i’ll show your family how much of a sissy fag you are in person. Now get down and suck our cocks.” He said with no humor in his voice. I got down to my knees and sat in between them. I took Bill’s cock in my mouth and Jake’s in my left hand. It was huge and i could barely get my mouth around the tip of his cock, but i still sucked ass hard as i could, while also lovingly jerking Jake’s.

“Now give me some love too” Jake said. I switched and started pumping Bill’s cock with my right hand, which was too thick to get my fingers around, and took Jake’s in my mouth. i could take more of past the tip but it was so damn long i had to arch my back upwards to get a position on it. I couldn’t help but love this. The way it felt and how Bill commanded me to suck the other cock every half minute. I was getting so much pleasure by having these manly cocks in my mouth.
“Alright little faggot, stop and get on all four on your parents bed. You knew this was coming” Bill said. I did know, they were going to fuck me and i was more then ready for it. I got up and did what he said. It felt so taboo to be on my parents bed like this but i loved it too. Jake put me facing away from the head board so he was standing in front of me. I was eye level with his cock and Bill applied lube he found in my parents drawer to get me ready.

“Normally i would loosen a sissy with my fingers first, before i fucked them. But i can tell you’re the type who can take the pain.” Bill said. He pulled down my panties and saw my asshole spread wide and ready to be used. Underneath he saw my cock hard and pointed out under me.
“ Know wonder you’re a fag. Your cock is so small it’s not made to fuck anyone. Now spread your legs a little more. You’re going to be used for what you were made for” Bill said. I did and i felt his head press through the ring of my asshole with his shaft quickly following after. I moaned like a bitch and Jake took the opportunity to shove his cock in my mouth. Bill started out at what felt like a fast pace and i had never felt so good in my life. I could feel an orgasm building in my cock by just having his enter and leave me over and over. I moaned with every stroke he took, but they were muffled by Jake’s cock that i was sucking on like it was for my life. I was using my tongue to try and pleasure Jake while bobbing my head as fast as Bill was fucking me.

Jake eventually started to take more control. He grabbed onto the sides of my head and He began to face fuck me and all i could do was stay on all fours and let these men use me to their heart’s content.
“Your faggot ass is so fucking good! I’m gonna fill it up with my cum so you know how you’re supposed to feel.” Bill moaned as he quickened his pace. He really started going much faster and it hurt even more but it only added to the pleasure. I was coming close to blowing my load with how good they made me feel.
“Ugh, fuck yes!.” I felt my insides grow warm and thick. Having his cum made me feel complete, like it was something i was trying to feel all my life and it finally was there. Bill pulled out of me and made me feel empty and aching in the best way possible. “Jake, if you want sloppy seconds on this girly ass, here’s your chance.” Bill offered.
“Yes sir. I think i will.” Jake replied. He pulled his cock out of my mouth and flipped me over on my back. He put me in missionary and entered my sore and cum filled asshole. He spent no time getting up to speed, within a few stroke he was pounding me and having me moan. His cock was getting deeper in me and hitting just the right spot where i needed it.

“Look me in the eyes while i fuck you. I wanna see the last part of your masculinity go out when you cum.” I looked him in his deep blue eyes and bucked my hips in rhythm with his thrusts.
“I’m..i’m about to cum. Yes! Please keep fucking my boipussy!” I moaned right before the orgasm of a lifetime hit me. My cum landed all over my chest covering the bra i was wearing and getting a little bit on my chin.
“You’re an official sissy slut now!” Bill said watching us, now fully dressed, Jake then fired off his cum load into me. I was completely full now with cum leaking out of me when Jake pulled out. “Now pack up, boy. We got other stuff to do before the day is over.” Bill said
“Alright dad let me get dressed first.” Dad? They were father and son? I guess i really help their family bonding.
“Now slut, we’re already done with the painting and we are leaving, but here’s our number. If you ever want this to become a full time thing, being dominated and serving us, you call and tell me. You can come over to or house and be ours for a few hours a day. We could use someone like you around the house.” I was kinda out of it after the orgasm so i just shook my head yes.
“Ok, here you go. We’ll be waiting slut, now clean up, you don’t want your parents to see you like this.” Bill and his son left. i slowly got around and clean my parent’s room and picked up the scattered clothing. I went to my room and took a long shower and let to cum drizzle out of my very sore ass.
Later that night after dinner i laid in bed thinking about how quickly my day had escalated and how good it all felt. Even now the euphoria was still lingering. I could never go without something like that now. I picked up my phone and dialed the phone number Bill gave me…

End of Chapter 1
This took me forever to get around to completing but i do want to make another chapter. It might take awhile but hold tight and enjoy.