My Father, The Maid Ch. 02

By the time I got back it was about 9:30, as I got out of the car I took a few steps towards the trunk to start unloading my stuff, but then a little voice in the back of my head said, "let the maid take care of that," and up to the front door I went. I rang the doorbell as I had yesterday when I first come into this crazy world I was now living. After a short time the door opened, and before me stood my father, wearing nothing except his wig, a bra containing his large fake breasts, an underbust corset with garters which were attached to stockings, and black high heels. His pink chastity device was on full display and it was obvious he didn't have a hair on his body below his eyebrows. He cordially invited me in welcoming me back and saying that Claire would be with me in a minute. He also asked if I had eaten or if he should make me something real, which I of course declined having just eaten.

As I made my way to the living room I glanced down the hallway I saw Claire coming out of her bedroom, she was dressed exactly as she was earlier in the day with one exception. As she came down the hall I saw something extruding from her crotch area that looked like a large stiff penis. When she stood before me I could see it was a large dildo, I'd say about seven inches in length, held in place by some kind of harness.

"Welcome back Oliver, I hope you had an easy journey." Claire said with a smile.

"Yeah, it wasn't bad." I said. After a brief awkward pause I decided to address the elephant in the room and said, "um, what's up with that thing?" I said pointing to the phallic plastic protruding from her pelvis.

"Oh this" Claire said with a chuckle, "this is my strapon. I bring it out every Saturday as a reward for the sissy if she has been good. You see since her little pee pee is locked up in that cage the only way she can have sex is to be anally penetrated. I am a loving wife and know my sissy needs sex, so I use this to provide her with the pleasure she needs."

"Um, okay." I said not knowing what to think about what I just heard. "Well, before you do that, would the sissy be able to go get my things from my car for me?" I said, trying to change the subject.

"Of course." She said. "Sissy, quickly put on a pair of panties so your indecent bits aren't exposed to the neighbors and go fetch Mister Oliver's possessions from the car."

"Yes Miss" said my father before heading down the hall to his room. He quickly returned donning a pair of white satin panties with the word sissy written in bright pink on the back. He walked out into the cold and carefully and diligently brought in all of my luggage and took it to my room where Claire ordered him to unpack all of my clothes into the dresser and closet.

Once this was done Claire asked me a rather unexpected question. "Now that the sissy is done with that it is time for her weekly fucking. Would you like to watch Oliver? I know this is your father, and you may feel a bit weird knowing about his sex life, but I figured I would offer."

I thought about this for a moment, while I did I looked over at my father and I remembered something. I remembered the reason Claire had asked me to stay here, which was most likely the reason she had asked me this, to humiliate my sissy father. I could see in his eyes that he wanted me to say no, that he really didn't want me to see him like that, and that is when I decided my answer.

"Sure, sounds interesting." I said to Claire.

"Excellent!" Claire said gleefully. "Sissy go take those panties off and get the lube ready."

"Yes Miss." My father said before leaving the room.

Claire then led me into her bedroom, which looked very comfortable yet also elegant, with exquisite furniture and an adjoining walk in closet which was slightly open. She motioned towards a wooden armchair with leather cushions in the corner and told me I could sit there and watch. My father returned to the room once again bottomless and carrying a small bottle of lube. As soon as he entered Claire ordered him to get on his knees. Once there she stood directly in front of him and said the word "open" to which my father opened his mouth and as soon as he did my step mother rammed the strapon all the way in until the plastic balls were against his chin.

After thrusting a few times she pulled it out and said "lube it now, quickly." My father poured some lube out of the bottle and into his hand, he then started rubbing it all over the dildo making sure to coat it well. After a few strokes it was well covered, Claire said "stand up and bend over the bed, now." My father obeyed, as he bent over I noticed he was no longer sporting the butt plug he was wearing earlier. Claire positioned herself behind him and slowly pushed the tip into his anus and continued pushing in down most of the length of the dildo, as she did my father vocalized a long moan of pleasure. Claire continued to thrust her strapon in and out, getting a little faster and a little deeper each time. At one point she started slowing down a little, but as she did my father yelled "fuck me harder, I want it deeper!" This caused Claire to go even faster than she had before for a moment, then she slowly slid it until was almost all the way out and then suddenly rammed it all the way in balls deep for the first time which elicited a yelp of pleasure from my father.

I will admit this was weird, watching my father get fucked by his wife with a strapon, but for some reason it kinda turned me on, I could feel my cock start to grow hard in my pants. I figured Claire wouldn't mind, so I pulled down my pants and started stroking it a bit, all while still watching. Soon after I started stroking my growing cock Claire looked over at a clock that just happened to be on the table next to me, before looking back she gave me a little wink. "You have thirty seconds before I stop sissy." she said as she once again thrusted in balls deep. This caused a definite response from my father, it seemed as though he was backing into her dildo as she was thrusting. I would say about fifteen seconds after she had set a time limit for him my father shouted, "may I cum Miss please?" Upon hearing this Claire thrusted in deep, pulled his torso up so he was in a standing position, grabbed his locked up cock and balls, and whispered the word no into his ear. As soon as she said that she released his torso causing him to double over again and then she pushed him off of the strapon causing him to fall to the ground. After taking a moment to catch his breath my father got onto his knees and looked up at Claire and said "thank you for fucking me Miss" after which he kissed both of her feet. Seeing that they were done, I tried to covertly pull my pants up, feeling awkward that I had been pleasuring myself. Claire then turned to me and said, "I could see you were enjoying the show Oliver.Don't worry, we do this every Saturday and you are always free to watch." She then turned to my father and sharply said "sissy I have grown tired, prepare me for bed."

My father rose to his feet and started undressing my stepmother, beginning by removing the strapon. Seeing this I stood and excused myself, feeling as though I was intruding. Claire told me I didn't have to go, but I said I was tired from the long day and made my way to bed.

I slept quite well that night and actually ended up sleeping in a bit the next morning. As I left my room I heard the bell ring from Claire's bedroom and saw my father enter without a tray leading me to believe she was just finishing breakfast. I made my way to the kitchen and poured myself a cup of coffee. I sat at the table flipping through my phone and sipping my coffee, after a few minutes Claire walked in, she was wearing jeans and a red blouse with half sleeves, her hair was up in a bun much as it was yesterday. She smiled as she sat across from me at the table and said, "good morning Oliver, how did you sleep?"

"Very well thank you, having some of my stuff in there made it feel more like home." I said with a bit of a yawn.

"I'm glad to hear that! Shall I call the sissy to make you breakfast?" She asked reaching for her bell.

"No, I have to go do a bit of shopping, get a few things I couldn't bring from home, I'll grab something while I'm out." I said before she could ring the bell.

"Nonsense, don't waste your money, she can cook you something while you get ready. And we would be happy to go with you, everything you need will be paid for by the sissy." She said before ringing the bell. My father entered wearing another pink dress, this one was longer, coming to about the knee, but it came out from his body quite a bit due to the petticoat he wore. He also had on white tights and pink shoes with a smaller heel than usual. His face and head were unadorned by wig or makeup. As he entered he curtsied to each of us, before he could say anything Claire said "Mister Oliver would like breakfast, and after you have prepared it get read to go shopping, Oliver needs some things."

"Yes Miss. What would you like Mister Oliver?" He said.

"French toast would be great." I replied.

"Excellent choice, the sissy makes great french toast, but it does take a while, why don't you go shower and get dressed that way we can get going as soon as you are done." Claire said.

I agreed and went off to the bathroom. After I finished my ablutions I went to the kitchen where the maid was just finishing my food, I sat down to eat it and he went off to get ready to go out. I ate my breakfast while creating a mental list of everything I needed. As I finished my father walked into the room, for the first time since I got here on Friday he looked somewhat male, wearing a blue and white striped shirt and black pants. Although upon a second look I realized the shirt buttoned on the opposite side of a regular men's shirt letting me know it was a woman's blouse, and I realized his pants didn't have pockets and the zipper wasn't in the front, but on the side, despite looking like a man, he was still wearing women's clothes. To top it all off if you looked you could see the outline of a bra fairly clearly through his shirt. Claire inspected him for a moment, and said "very good sissy, but how are you going to carry money to buy us things, go get a purse." He said a quick yes Miss, and quickly left the room to do as he was told. As we stood there waiting Claire asked me, "so, what do you need to get?"

"Well I'd like to have a tv for my bedroom, some kind of desk for my computer, maybe a chair for in there. Also some different bedding would be great, I'm used to softer sheets. Oh, and you don't have any men's soap or toiletries here." I said.

Claire laughed and said "why would we? Until you came along no men lived here, just me and the sissy. We can definitely get all that, I actually have some things to pick up too. We should be able to get everything we need at the local shopping center."

By that time my father returned to the room carrying a small black leather purse. I looked down at his feet as we left, he was wearing normal unisex shoes, but I noticed that his pants were a bit shorter than most men's pants, and around his ankle was a small gold chain, which had the word sissy hanging from it.

We all went out to the car, as we approached my father opened the front passenger side door and Claire got in, he then opened the passenger side rear door and motioned for me to get in, which I did. He got into the driver seat and off we went. The journey was pretty uneventful, Claire and I had a conversation without acknowledging my father at all. Soon we were at the shopping center, Claire instructed her sissy to first pull up to the Best Buy where she made him buy me a 56 inch high definition tv. After that was over to Ashley HomeStore where we purchased a large computer desk, an office chair, a luxurious armchair all of which they would deliver the next day, and 800 thread count egyptian cotton sheets. After this we went into the mall proper, by this point we were all fairly hungry, so we decided on a quick lunch at the food court. Claire and I both sat down at a table and sent my father off to get our orders. Lunch went by without any incident, for a moment it even seemed as Claire allowed my father to her equal as we all had a conversation about some incident from a few years ago at Christmas. After lunch Claire handed me my father's credit card and pointed me towards a specialty men's grooming shop to purchase my toiletries while her and my father went to take care of something else, saying they would come find me when they were done. I spent a bit of time in the shop looking at the various soaps and scrubs, I ended up walking out with everything I needed to be completely comfortable in my new home. As I left the shop I could see Claire and my father walking towards me, as we walked towards each other I noticed something peculiar, my father was hanging his head a bit, as if in shame or out of submission.

When we reached each other Claire asked "did you get everything you need?"

"Yeah, thanks. Did you two take care of what you needed to take care of?" I asked.

"Yes we did. I decided to get your father a little gift. Show your son what I got you dear." She said. At that my father slightly turned his head, and I saw it. In each ear was a small butterfly earring stuck in the middle of each lobe. As he showed them off to me a group of young girls were passing by, I could hear them softly giggle at the sight. "Those will have to stay in for at least four weeks until they are healed, but after that he can wear whatever he wants."

With that we decided we had gotten everything we needed and we should be on our way home. On the drive back Claire and I were once again having a conversation, when she was distracted by a text message she received. She read it over and replied, and after receiving a reply turned to my father and said, "well that's a shame, looks like Mark isn't going to be able to come by tonight, isn't that disappointing sissy?"

"Yes Miss, very disappointing." My father said, in a way that sounded both disappointed yet also relieved.

As soon as this brief exchange concluded Claire jumped right back in wherever our conversation left off. Not long after we pulled into the driveway. Claire ordered my father as soon as we parked to "take in all of Oliver's things, then change into your dress to make dinner." Claire and I continued to talk in the living room and watched tv until dinner was ready. The maid called us in and we had another amazing meal cooked by him. After dinner I excused myself to go set up my new tv and Claire said she was going to her bedroom to relax a bit. I was able to easily get the tv hooked up to my PS4, but would have to call the cable company to get actual tv channels. Once I got it set up I went to the living room to watch some tv before bed.

As I was sitting there watching tv Claire walked into the room behind me and said, "Oliver I have a bit of a problem and I was hoping you could help me with it."

"Yeah, what's up?" I said as I turned around. Standing there before me was Claire wearing nothing but a red lace bra and a matching thong.

She walked up really close to me, to the point where her boobs were resting against my chest. She looked up into my eyes and said, "you remember while we were driving home from the mall I said something about someone named Mark, well he is one of my boyfriends. Since your father is such a small dick loser I have to go to other people to satisfy my urges. You are a sexy young man, and I saw how big your dick is while I was fucking the sissy last night, to be honest I have been thinking about it all day." By that point she had reached a hand down and was carressing my cock through my pants. "Please Oliver, I need you to fuck me like a real man."

I won't lie, my stepmother is a gorgeous woman, and I have always thought about what it would be like to go to bed with her, but she was my father's wife. I took a step away and said, "I can't, this isn't right. You're married to my father."

"That doesn't matter, she knows I need sex, and she wants me to be happy. In fact don't take my word for it, ask her for yourself," she said as she rang her little bell. My father walked into the room in the same dress he was wearing earlier today, he curtsied to each of us then asked what he could do for us. Claire said, "sissy, tell Mister Oliver that you are okay with me fucking real men and that you want him to fuck me."

My father then got down on his knees in front of me and looking up to me said "please Mister Oliver, fuck Mistress Claire since I am not able or worthy of doing so myself."

I looked over at Claire, she was damn sexy and I just couldn't hold myself back. I looked down at my father and said, "remove my belt so I can fuck your wife." He did as he was told and soon my pants were on the ground. Claire led me to her bedroom, with my dad following. Once in the room she commanded my father to strip her naked, he did as he was told and removed her lingerie and neatly folded it. He started to walk away, but I stopped him and made him also strip me completely naked. I then got into the bed with Claire, who told my father to stay in the room, so he could see how his son, a real man, satisfies a woman.

We proceeded to have the most amazing sex I had ever experienced, Claire was amazing and despite her age and having been with quite a few men she was really tight. We fucked for what seemed like hours, it was amazing. Eventually I could feel it, I was about to cum Claire said through her moans that she was too and she wanted me to finish inside her. I errupted in a within her in one of the best orgasms I had ever had as she orgasmed too. I laid back, exhausted from the act of desire I had just finished, Claire also laid back, but she said three words, "sissy, clean me." When she said this my father rose from the corner he had been kneeling in, came to the foot of thre bed where his wife laid, and climed up. Soon his face was directly in her crotch licking up all the fluids produced by our orgasms. Once she was finished she kicked him off the bed and said she was going to bed and he was dismissed, he left the room with a customary "yes Miss." I started to get up to head to my own room, but Claire stopped me, saying "you can stay here tonight, and any other night you want," with a little wink. And with that, we both drifted off to sleep.

END OF CHAPTER TWO.

Hello all, I hope you enjoyed part two of my story. The feedback I got from part one was completely overwhelming and I want to thank every person who took the time to tell me what you thought. As always please leave a review so I know what you thought and if you want more. If you didn't like it also leave a review so I know what to fix.

If you don't feel like leaving a review here feel free to send it as an email or you can message me on kik, I love talking to my readers, so please message me.

Also in an unrelated note I am looking for a Mistress to serve, so if you know one let me know!

Thanks XOXO

Sissy Oona.