Silky, Jay, Me, and More Part 3

There was a knock at the door and I got up to answer. He opened the door and Sidney was there. I invited him in and closed the door. He told me that he really appreciates what I am doing. I poured us some wine.
We sat on couch and drank our wine. Sidney seemed very quiet. I started the conversation by telling him that I am open to whatever he wants to do. I told him that I am submissive to his needs and will honor his requests. He told me that he is really at ease and appreciates again what I am doing for him. We finished our wine and I poured another glass for us. When I sat back on the couch, I told S that we should start by kissing. He agreed and took me in his arms and gently kissed my lips. He smiled and said that was nice. He kissed me several times with the last kiss being very passionate, wet and his tongue was totally in my mouth. When our lips released, S told me that I am a good kisser. He told me that he wants to undress me and kiss my toes through my stockings. I told S that he can do whatever he wants. He took our wine over to the bedroom, sat down, and finished our wine. He told me that he was so nervous when he first saw me. I told me to relax and whatever he wants now is his command and my desire to satisfy him. He kissed me and I moved his hand to my knee. I could see that he was more relaxed. He asked me to kneel in front of him and I did. He was becoming a take charge man. I pulled his pants and underwear down and out popped his penis. S told me that he really like my long red hair. It is real sexy and is a complete turn on for him. I took the tip of my tongue and touched the hole in his penis. His tool became so large that his expansion was immediately. My mouth covered his penis and he pulled my head flush to his penis. S started to cum and I swallowed all of his cum into my mouth. I told him that he has a nice cock and kissed his balls and penis. He unbuttoned his shirt and took off. His pants and underwear fell to the floor and he kicked them away. I took off his shoes and socks. Now he was naked. We were both back on the bed and he told me that he wants to do some things to me before he takes off my dress and get me naked. I told him that I am here for him. He began by kissing and massaging my legs. I told Sidney that I like his touch, especially when his hands and lips are touching my inner thighs, penis, and balls. It felt great. Slowly, his hand pulled my body onto his lap. We kissed for a while; then his hand wandered down my legs. He told me that my high heels will come off, so that he can kiss my toes. My high heels will then be put back on my feet for sex. S said that I will be fucked three times; after the first fucking that my heels will come off; after the second fucking, my nylons will come off; then, my last fucking will be done with me totally naked as he secretes his cum once again onto my private parts. I asked S what happens if he cannot do the three fucking as planned. He said that he would be my bitch for as long as I want. If he does this fucking three times, then I will be his bitch for as long as he wants. I agreed. He then moved his hand up to my thighs and into my private parts under my skirt and into my panties, while we kissed. I told him that I like a man, who knows what he wants. He massaged my balls and penis under my panties as we kissed. S knelt in front of me and took off left high heel and started kissing and licking my toes. It actually felt good. He did the same to my other foot, taking off heel and kissing toes and feet. Then, he put my heels back on my feet.

He looked at me and said that it is time for me to become naked. I told S that I want to be naked with you. He unzipped my dress and moved it down my legs and off my body. He kissed my lips and put his hand into my panties. I told him that I like his hands down my panties touching my privates. I asked him if he ever put his hand down the panties of a woman or man before. He said no. I told him that it felt very good. It seemed like he did not want to let go of my balls and penis. For a few more minutes, we kissed and he massaged my lower parts. S unclipped my bra and threw it on the floor. He kissed my nipples for a few minutes. He moved my panties down my thighs, legs to my ankles and off. S told me that I have a great body to fuck. I said thank you and that it is your responsibility to fuck my body. He asked me if I enjoy wearing women’s clothes and underwear. I said that I do and that I am going to change my private parts to a woman’s. He thought for a minute and told me that he could fuck me as a guy and then as woman. If he fucks me three times now, then he wants to fuck me into the future and no excuses. I agreed, figuring that he probably would not be able to fuck me three times. I continued to sit on his lap. S massaged my privates as we kissed. Then, he stopped and said to me that it is time for the first fucking. I moved to the middle of the bed, and told S that I am ready, willing for a drilling, and very fuckable. He joined me and inserted his left leg between my two legs, massaged my balls, kissed me, and exploded a wade of cum on my penis. The feeling was intense. After we stopped kissing, S took my hand and we went into the bathroom. He cleaned me up and said that he will do all the work. He told me that he likes playing with my penis and balls. I told him that he should play away with my privates. He smiled. We walked back to the bed hand in hand. I felt like I was a teenager again. I know as I got older that my need for sex was more a deep craving each day. I had to have it. We got to the bed; he smiled and asked me if I knew what would happen next. I told him that my high heels must come off before I can be fucked again. S smiled again and told me to sit on the edge of the bed and extend my right leg to him. This I did. He took off my right high heel and placed it on the floor. He kissed my toes. I then extended my other leg and he removed my shoe. He kissed my toes again very passionately. He pointed to the middle of the bed and I laid down waiting for his fucking. Again, he moved his left leg between my two legs for position and we started to kiss. Before I knew it, S was cumming all over my privates. The cumming and kissing intensified as his cum pour over my private parts. As we stopped kissing, he hugged me. We then got off the bed and went to the bathroom. Sidney cleaned me up and we went hand in hand back to the bed. We kissed and he said you know what is next. I said that the nylons must come off. He smiled and touched my thigh and moved my right nylon down leg to my ankle, and off. He did the same to the other leg. Now, both nylons were off, I was totally naked with him, and I loved his touch. I went to the middle of the bed for my third fucking. I told him that I am willing and ready to be fucked. This time he struggled and could not get his penis up for a cumming of my private parts. He struggled for quite a while. Then, he stopped and I kissed him. S said that he was sorry but he could not fuck me. I told him to relax. He said that he really wanted to do it. I told him that I am going to lie on my stomach and he needs to take his penis and run it between all my toes until it is hard. When hard, I told him to spray my ass, my feet, or legs. I told Sidney that it was his choice. S smiled and said yes. I told him that there is some oil on the table and he can put it on my feet and his dick. It should get him ready for his last fucking. S oiled his dick and my feet until they were totally lubricated. He ran his dick through my toes time after time. It felt great. Then, his dick got larger until I next felt his penis spray hot cum over my feet. When we went to the bathroom and cleaned up, I told him that we are not done yet. He said to me that he loves the oil and wants to lubricate my privates next. I said okay. I stood up as he oiled up penis and balls. Once, I was oiled, we laid down face to face kissing on the bed. He massaged my privates. His hand was on my penis and balls really and turned me on. As the kissing intensified. Our organs began to get bigger. Time passed quickly as we kissed and our feeling intensified for each other. I told Sidney that I need to feel him inside me. He said ok, but did not think he could get his dick up for it. I told him that I would take care of it. I got some more oil and lubed up his penis with my hands. As the oil and my hands created a nice sensation on his dick, I told him to get his dick inside my ass hole. I turned over on my side and raised my left leg into the air. He moved his penis to buy ass hole and with his hand and inserted his penis into my rear hole. It went in nice and easy moving very deep inside me. Once, his Dick was inside me, his penis cummed inside me hard and fast. When done, I turned back over and kissed him passionately. I thanked him for a job well done. I told him that even if I make a change to women parts that I still need his penis in my ass. I told Sidney that I enjoy that feeling of the penis fucking my ass. We kissed a little bit longer. Then, we took a bath together. We kissed some more and had more sex, while we were in the bath tub. When we finished our bath, we went back to the bedroom. As we walked toward the bedroom, J. and silky her sitting on the couch drinking wine. They asked me to sit between them. Sydney excused himself, got dressed, and left.

J. and silky told me that I have two more things to do before the operation. Silky told me that I can still change my mind and everything will still be okay with them. I told them that if they want me to change from a man to a woman, I would still do so. I asked both of them what my next assignment would be. Silky said that I would dress up in another feminine outfit, but I would have to make this 18-year-old girl a woman on her birthday. I would have to sell myself on the idea that having sex the first time with someone older is much better to initiate her into womanhood. The following day, my day would be spent with silky and having sex with her all day as promised. The following day is the operation if I decide to go ahead with surgery. She told me that J. will not take me to the bedroom and dress me and then I can live. J. started me into the bedroom and there was a new gray dress, gray 5 inch high heels, nude nylons, gray bra and panties. Silky came into the bedroom shortly thereafter to watch Jay put these clothes. I sat on the bed, while J. got a new pair of nylons for me. Jay positioned himself, spread my legs, and stared at my private parts. Jay’s eyes were fixed at my penis. I told J. that he can suck my stick if you want. He smiled and thanks. He started sucking on my penis and in hardened and started secreting cum into his mouth. He continued to suck after my penis subsided in size. J. kissed my loins very passionately. It felt good and it turned me on. I told J. that I enjoy him working my inner thighs and private parts like no one can. He smiled. He put the first nylon of my right to those and moved them up my legs to my thighs. His touch was great. He did the same thing to my left leg putting my nylons are left leg all the way to my thigh. He stopped a minute and kissed my lips. It was a hard physical kiss. He got the gray panties and place them at my feet and move them up my legs to cover my privates. He put my bra on next and fastened it onto my chest. He then told me to stand up and I stepped into the gray dress. He put my arms into the sleeves of the dress. Then, Jay zipped up the back of my dress. All I needed now was my high heels on my feet. J. retrieved my shoes. He knelt down and held my left foot kissing my toes. Holding my left foot, Jay slid my toes into the 5 inch gray high heel shoe. He then took my right foot and kissed each toe. He then put my toes first into the high heel and I was completely dressed. I walked around the room in my new outfit. Jay said that I look like 1 million bucks. Silky confirmed the same. As we walked out to the main door, J. kissed me hard on the lips. Silky PULLED me toward her and planted a great big kiss on my lips. She told me that if everything goes good with the 18-year-old virgin, I could have sex with silky the rest of the day. I blushed and was very happy to know that by long time fantasy with silky would become a reality. I then left.
—————–End of part three————————-