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  1. Pleasing Bill: A Crossdressing Story #1
  2. Pleasing Bill: A Crossdressing Story #2
  3. Pleasing Bill: A Crossdressing Story #3

Pleasing Bill: A Crossdressing Story #3

Categories Dark Fantasy, Anal, Blowjob, Discipline

Author: JessRider

Published: 16 February 2017

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[b]Chapter 3: Mom’s Talk
[/b]I woke up early the morning after my first day of being Bill’s live in slut. I got up to listen and hear my dad and siblings leaving for work around 7. I was going to wait for all of them to leave before I dress and go back to Bill’s at 12. I went to lie back down but before I could, I heard my mom call me.
“James, honey. Can you come down here?” I didn’t know what to say a first. She probably wants to talk about how she saw me last night. I guess there was nothing else I could do but go down there. I was in my pajama pants and a white tank top on with the black and pink Daddy’s slut colr on. I made my way down the stairs and to my mother who was drinking coffee on the kitchen table reading something on her phone. My mom looked fairly young for someone her age. Shoulder length reddish brown hair with sharp features and she had on a black business dress. She looked up to greet me and asked me to sit with her.
“Hi.” I said sheepishly.
“Good morning. So I wanted to talk. I figured it was better to do it after your father has left. But apparently you have a different “daddy” now.” Mom said referring to the collar.
“Uhhh yeah, I guess I do.” I didn’t know how to respond.


“So would please explain to me where you were yesterday and why you have that on?” she demanded. I guess I don’t have anything left to hide now so might as well be honest. I went on to explain that I began to try on my sister’s clothes while nobody was here. And that I did it for years before I was caught by the painters who came over the other day. Then I got to the really awkward part. I tried to explain in the least detailed way that I let them have their way with me and they convinced me to go over to their house every day to be their worker who they can fuck anytime. As I was telling my mom the story I realized that I was hard as a rock. Was it because I was recounting the events or recounting them to my Mother?
“So you’ve become this man’s willing sex slave?” She asked when the story was over.
“Yes. And I’m sorry. It was a dumb idea. I’ll stop all of this now as long as you don’t tell dad.” I begged.
“No, James. I’m not going to make you stop, you clearly enjoy this. But if your father finds out he’s not going to be happy about it and I won’t be able to stop him from kicking you out.” She said. I was overjoyed that she wasn’t going to tell my father or stop me from going to Bill’s.
“Thanks mom. You’re the best.”
“I can be even better if you want some help getting ready?” I couldn’t believe this. My mom was okay with me being a sissy slut and was even going to help me do it. We went to my parent’s bathroom and she got some clothes and make up for me to use today.
“This man Bill wants you to be a slut so regular clothes is where you went wrong yesterday. You need to dress the part and sound that part. Try these on.” My mom gave me a bright green g string, a blue mini skirt and a black spandex tube top that ended above my belly button. I was going to change into it, but, I was waiting for my mom to leave. But I saw she wasn’t planning on leaving.
“What? You scared to change in front of your mom?”
“Well it’s a little awkward.” I said.
“Your sister and I have changed in front of each other. It’s not that big a thing between girls. If you really want to be one.” Mom said daring me. I guess she was right, I took off my shirt and pulled down my pants my cock sprang to life again. I tried to cover it but it was no use.
“Well you’re really enjoying this. Is it because you’re changing into girls clothes or because I’m here.” She asked coyly. My face was on fire with embarrassment. And I stayed silent.
I changed into the outfit and but my penis was still hard and lifting up the skirt.
“It sometimes takes a while for it to go down when I dress up.” I explained
“Well if you want to go out in public you can’t afford to wait. Anyway stand in front of our mirror and let your mother do your makeup.” I did and she began. It took much longer than I usually take but I saw why when she was finished. I looked gorgeous and had on way more makeup then I would usually, making me look really sluty.
“Wow…” I said in admiring myself.
“Glad you like it. I hope this Bill appreciates my work. Now go get the wig you were wearing.” I did what she said and came back down with it on. She helped comb it out and make it look new. After that I was ready to go see Bill. It was almost noon and he would be expecting me.


Chapter 4: Livestream
“Thank you so much mom. For everything.”
“You’re welcome. Just please be safe.” She said as I was getting in my car and leaving the garage to drive to Bill’s. As I drove I felt my cock pressing against the cloth of my thong, throbbing. Being seen in public even while in a car was exciting but I don’t think anyone would get a good enough look at me. I got their right on time and knocked on the door. Bill answered and let me in.
“Good to see you on time, slut. And damn don’t you look fucking good, still got the collar on too?” He said impressed.
“Yes daddy, did just what you said.”
“Did your family see what you looked like when you got home?” Bill asked with a smile. I hesitated to replied and said.
“Yeah…my mom saw me.”
“She did? What did she have to say?” He asked
“She asked what I was doing and I told her about what happened. She said she was going to let it continue and she even help me do my make up.”


“Well isn’t that the best. I wanted at least someone in your family to know because this will get hard not having anyone cover for you. I think I’ll try to get in contact with her sometime. But now it’s time for you to get to work.” Bill motioned me to follow him I did and we went to the back room where he was setting things up yesterday. In the room were just a bed, a computer desk and a tripod with a camera on it. Just looking at the setup I could guess what he would want me to do.


“I figured you and I can have some fun and also make some money at the same time. Sound good?” Bill asked. He wanted to do a webcam show where people pay to watch you do dirty things.
“Of course daddy anything you say” I said with a smile. I was getting excited thinking about it.
“That’s a good slut. Now before I forget you need to take this home with you. Take one twice a day.” Bill handed me a large pill bottle.
“Uhhh what are they?” I asked
“Estrogen pills. They’re going to help you become more feminine. You’re going to look even more passable.” Bill concluded. I couldn’t believe I was going to start taking these but I had always wanted to try taking some. I opened up the bottle and took a pill and wash it down with some water Bill had for me.
“Good. Now get ready for the show because it’s going to start soon.” Bill said. I made sure my hair still looked good and lubed up my hole. Bill told me to get on the bed and said the camera was live. There were already a dozen people in the chat room when we started.Bill said to lay on the bed and look sexy and requests will start coming in before the real show began. The first one only took a minute.
“Anonymous550 has a question for you. He wanted to ask how many cocks have you sucked?” Bill said with a grin.
“I’ve only sucked two” I replied with a sexy smile into the camera.” Almost right after that another ping came up. This time giving 5$ to show off my ass. I got on all fours and showed my ass up though my short skirt to the camera, shaking and pulling down my G-string to show my spread cheeks. When Bill said that was enough I stopped and pulled it back up.
“You’re doing good slut girl. Now we got another one here for you.” He tossed me a string of large sized anal beads.
“Put them in your asspussy and keep them there” he commanded. I took off the G-string but not the skirt and started with the first one. It was wider than anything I’ve had before, but I still managed to get it in. The second one was harder. After all five were in Bill told me to lie on my back and jerk off.
“Mmm yes daddy.” I replied feeling good with my ass filled. Pointing towards the camera I started to jerk off my little cock. I was only half as hard as I could be but my guess was the e-pill was kicking in. While I was doing it I heard a bunch of pings go off. Bill came over and pulled all of the beads out of me in one motion. I screamed out in pleasure and immediately started shooting cum on my stomach.
“Hahaha I can’t believe you came so quickly. Well you’re probably going to a few more times before this is over. Now clean yourself up you dumb bimbo” Bill said I scoped up all of my cum off my stomach and swallow it without hesitating. More pings went off.
“Well now we have a real audience. 200 people.” 200 people! I didn't expect that many to be watching me. I was getting turned on again already.
“Now we got a big donation. Get on your knees slut.” Bill commanded. I got up and got on my knees in front of my master. He removed the camera from the tripod, and held it pointing down at me from his perspective.
“I don’t need to tell you sissy.” He didn’t and I undid his pants and pulled down his boxers. His cock was at half mast, I hadn’t seen it since we first meet the other day. I missed it and took the real man’s member in my mouth.
“That’s right slut, you need to feel a real man’s cock in you to feel happy. Keep looking into the camera. That’s right. You’re my whore now; I can see it in your eyes.” Bill said while I bobbed and sucked up and down his 8 inch cock. My body felt warm while i pleasured him. I went down on his cock over and over again. I gagged myself several times trying to deepthroat him. At one point i tried to do it again and Bill pushed my head into him getting me to gag even more and forcing me to take almost all of his cock in my mouth. I could taste his sweet precum running around in my throat. After a few more minutes Bill said to stop.
“Get that thong off and get on all fours on the bed. You know the position.” I did as he said, i needed to feel him in me. Bill put the camera on the tripod and moved it so I was taking up most of the shot.
“We’re up to 315 watchers now. You like being that popular slut?” I never would have dreamed that many people wanted to watch me like this. Bill got behind me and got his cock to my entrance. Bill started to push into me and he got it in with little resistance, within the first few strokes he was already completely in me. I push back into him with his thrust needing to feel his cock rub against my walls. I began moaning as he was getting into the rhythm of his thrusts.


“Yeah that’s right, you’re my whore. Who am i? And who are you? Tell it to the camera.” Bill commanded as he gripped my ass hard and fucked me like an animal. I looked into the camera knowing hundreds of people, even people who might know me, were watching.
“He’s my master and I’m his property. I’m his sissy slut to do whatever he wants with.” I told the camera between moans. More pings came from the computer. I was getting off knowing all the people watching me, and probably jerking off to me too. Bill continued to fuck me and my pleasure reminded me why i love this. Feeling my ass spread apart and filled over and over was causing me to cum soon.
“Good girl keep talking” Bill commanded. I felt so good i couldn't help what i said.
“I’m his dumb girly slut. He found me at my home cross dressing and fucked me, convinced me to be his sex slave, and do whatever he wants with me. I said yes because I know that I’m not a real man and should be used my real men.” I said while Bill was fucking my ass so hard i could tell he was about to cum.
“That’s just what you are baby! Now get on your back quick!.” said Bill pulling out of me and flipping me on my back. He grabbed the camera and pulled it close to my face.
“Say ahhh bitch.” He commanded
“Ahhhhhhh” I said open mouth and smiling having the time of my life. Bill jerked his cock over my face until he came. Ribbons of cum flung themselves over me covering my face chin to eyebrows. A good amount made it into my mouth too. I layed there grinning and giggling feeling like his slutty princess.
“You really like that cum, slut? You want some more?” he asked
“Yes daddy i need more” i said in a girly voice not even meaning too.
“Start jerking your over sized cilt and aim for your face bitch.” Bill grabbed my legs and put them in the air so my cock was over my face. I started to jerk myself off and within seconds my cum came raining down on me. This time none made it into my mouth and i covered my face even more than before. I was so much it ran down my face into my chest. I was shaking a little the orgasum was so huge.
“Don't waste any of that slut. Swallow it all. Tell me how you taste.” I did and it was amazing to try my own cum. I should have done it before.
“It’s soo good daddy. I wish i had more.” I couldn't help how i sounded or said.
“You will bitch but it’s time to say goodbye to our audience.” I looked into the camera.
“Thanks for watching everybody” I said and winked. Bill cut the feed and said that almost 400 people were watching.
“Wow, how much did they donate?” I asked curious.
“None. It was a free stream.” None? I did all that and anyone who clicked could watch me? It was freaky but i also felt good.
“I thought you wanted to make some money, sir?” i asked
“I do. I post the stream afterwords on pornsites and make money off the views.” My heart skipped a beat. Anyone could have a video of me doing all of that. It will be on the internet forever. I loved it. Bill got me to clean up and put on my outfit from earlier. The stream was only about an hour long so Bill had me just do some house work and cook the rest of the day. Around evening BIll told me to leave and be ready to this again tomorrow. He planned out a live stream schedule. I remembered to take the pills bill gave me, so i could become more girly. Right before i left bill stopped me
“Now after your first few days i think you know where you stand, right?”
“Yes daddy i’m yours to own” I said without hesitation.
““Ha! I like that, now let's get the collar off you.” Bill took it off but i could still feel it around my neck. I was kind of sad to take it off. But i couldn't have it on all the time. Still, I knew i was all his now…

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Pleasing Bill: A Crossdressing Story #3

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