Jumping off the deep end, admitting everything and seeing what I could look like.

Gathering up the sheets and all the discarded clothing from the room, I stopped and looked at the clothes in the basket. Gone were any kind of male undergarments, the only clothes inside the basket were discarded female clothes. I looked at all the discarded bras and panties and felt my cock harden. Not seeing any male underwear excited me and made it seem like the house was filled with only women. Knowing that now I was one of the women in the house filled me with a sense of pride. I was slowly getting to live out one of my deepest fantasies all thanks to the best girlfriend on the planet. How many men had a girl who would agree to do anything and then find out that their boyfriend wanted to become a shemale MILF with huge breasts. Any other woman would have left me in an instant, but not Carrie. She was pushing me and helping transform me into what I had always fantasized about. I could not wait till my next appointment to help sculpt my face and body to match the image I had in my mind.

Taking the dirty items, I went to the utility room and sorted out the clothes before starting a load of laundry. All the time I had been studying how to be a proper housewife for Carrie had left me almost subconsciously wanting to cook and clean. I knew my cooking skills were not the best yet, but I was still learning, and I hoped that soon I would be able to cook proper meals like a good housewife should. Going back to the bedroom I got new sheets then made up the bed and cleaned up the leftover mess from last night's activities. After I was satisfied with how the room was properly cleaned and made up I walked into the bathroom to clean myself up. I wanted to look pretty for Carrie, even though my features had only softened a little from all the treatments and hormones I had been on. Looking in the mirror I pictured what I would look like soon enough, a womanly angular face with thin eyebrows and thicker lips. Not like those online bimbos who were obsessed with overinflated dick-sucking lips though. I wanted to still look like a respectable MILF most of the time.

Feeling the hot water on my sensitive skin kept my cock hard and I wondered if it was the hormones that made my skin this sensitive or if all women had skin like this. Cupping my breasts, I felt how the pressure had built up over the night while I was cleaning. I slowly started to squeeze them like Emily had last night. Milk started to spray out in all directions from my large nipples, it was quite erotic and I found myself bringing one of my breasts to my mouth so I could taste my milk. It tasted a little funny compared to cow’s milk, though it was not unpleasant. As I continued to milk myself and suck some of my milk out of my breast my mind wondered what happened to the milk collection bottles from the pump. I had not seen them or the pump while cleaning up the room. Had Emily or Carrie done something with it, probably just dumped it down the drain. After Drinking a decent amount of milk from each of my breasts I continued to work them till the pressure subsided. Once satisfied it would take some time before the pressure returned, I lathered up and washed my now longer hair. I had not gotten used to having longer hair yet, I wanted to have at least shoulder-length hair. This was not something that we had discussed yet but I wondered if Carrie had a preference for hair length.

Drying myself off I was glad that my cock had calmed down enough to not make a tent in my panties as I pulled them on. It was nice that the hormones had not affected my ability to get hard yet, the doctor had warned me though that this would soon be an issue. I hoped that when that happened Carrie would be ok with my diminished performance that would no doubt bring on. She did seem to enjoy fucking me a lot more recently. The addition of Emily to our bed as well had given her more outlets for pleasure. How this had changed my relationship with my sister was still something I was trying to wrap my head around. With her wanting to help turn me into a perfect sister, how she would whisper things to Carrie who would then look at me and grin. I wondered just what she had planned for me beyond my desires.

Now dressed I walked out to join Carrie and Emily; I was wearing a pair of skinny jeans that hugged my now larger hips and ass. My top was stretched tight against my large breasts leaving the outline of my bra visible. When I entered the kitchen, I saw both the girls sitting at the bar laughing at something. Carrie smiled at me, and Emily giggled while looking away to hide her face for some reason.

“Ummm, did I miss something?” I asked, my tone thick with concern.

“Oh, don’t worry your pretty little head, Trista.” Emily said while still trying to suppress her giggles.

I moved closer and sat down next to Carrie who kissed me on the cheek before taking my hand in hers. It was warm and made me feel more comfortable, I still had no clue what they were discussing before I walked in. Emily, who had always been very mischievous, seemed to be even more so since finding out my secret.

“You are getting a lot better at dressing yourself Trista, I’m proud of all the effort you have been putting in. I heard you start the laundry just like a good housewife should.” She winked at Emily who could no longer contain herself and her giggles turned into full-blown laughter.

“Who would have thought, my big brother always dreamed of being a submissive housewife. I still can’t believe you hid this for so long. Don’t get me wrong, I love it and I’m going to help Carrie with your transformation every step of the way. You are going to be the best little sister ever when we are done with you. Carrie and I have been discussing so many things we want for you.” Emily looked me up and down with a hungry look that no sister should ever give her sibling. “Oh! I almost forgot! You have an appointment with Dr. Williams, he specializes in transitional surgery and has agreed to see you today for the next part of your transformation.”

Emily stood up and walked to the fridge where I saw the collection bottles from the night before. I watched as she poured a glass of milk and brought it to me. Grinning, she set the cup down in front of me. She expected me to drink the glass of milk, did she know I watched her pour the milk from the bottles that had been used to collect my milk the night before I wondered. Slowly I took the cup and smiled at her.

“Drink up silly, you need to drink as much milk as you can to help you grow into a delicious woman.”

The stress she put on the word delicious made me a little concerned. Picking up the glass I took a small drink tasting the milk. This confirmed that it was indeed the milk from last night, I liked the taste of it cold a little better than directly from my breasts. As I drank Emily giggled once more then looked over at Carrie who nodded back at her.

“Well, Trista, it would seem that we are going to be saving a lot of money on milk from now on. You seem to like your own brand.” This statement caused both Emily and Carrie to laugh before Carrie continued. “I was a little worried that you would not like breast milk, I guess that was unwarranted though. I had some of it for breakfast and I can say honestly that I also like the taste of it. So, seeing as Emily here has seen fit to turn your soon-to-be colossal breasts into milk factories we might as well put it to good use.”

Hearing Carrie explain that I was going to be the family cow from now on providing the household with milk for some reason turned me on. I felt my nipples harden and poke through my bra and shirt, my hands went to my lap to adjust and hide my growing erection. I hoped it was not that obvious how this was turning me on till Carrie reached out and brushed one of my hard nipples.

“What’s wrong Trista, the thought of being our family dairy provider turns you on. Should I get you a cow print bikini, a cow tail plug, and some small little horns for you to wear? Would you like that baby? Would you Moo for us while one of us milks your huge udders?” Carrie continued to tease my nipple through my bra causing me to let out a soft moan.

Doing my best to contain myself I pulled away from Carrie's hand, what I didn’t notice was Emily had moved around behind me and was now groping my breasts. She started to tease my nipples when she saw my hands in my lap.

“Looks like Trista does like the thought of becoming our little Holstein cowgirl. Though we should probably stop teasing her. She looks so nice, and she even picked this outfit out herself. I’m so proud of you Tris! We should go so we are not late for your appointment; Dr. Williams is a very busy man, and you don’t want to know what I had to do to get seen so soon.” She laughs while miming giving a blowjob.

Both Carrie and Emily got up and walked to the door before looking back at me. “Make sure you clean up here honey, then meet us in the car. We don’t want to be late for your next round of changes. Who knows what Dr. Williams will want you to do for him if you miss your appointment.” Carrie winked and then blew me a kiss before walking out the door with Emily close on her heels.

I quickly gathered up the dishes, loaded up the dishwasher, and cleaned the bar top before adjusting my shirt and bra then followed them to the car. I noticed that Emily was in the front seat with Carrie, so I got in the back. As we drove to the doctor's office Emily turned the radio and tuned it to a station she liked. As the music was playing, I sat in silence as both she and Carrie started to sing along with whatever the female artist was singing. Not knowing the artist or the name of the song made me feel a little ashamed. I wished I could sing along with the girls, though I knew my voice was still in flux with all the hormones. I probably would sound like a dying cat if I tried to sing along with them. After a while, we finally pulled into a clinic and we all got out, heading inside I noticed how nice and expensive the entryway was. Emily spoke to the receptionist behind the counter, the man behind the counter was the embodiment of an alpha male. It looked like his muscles had muscles and I saw both Carrie and Emily looking at him with a look all too familiar.

Carrie instructed me to sit down in one of the chairs while she and Emily chatted with the receptionist. I could hear them giggling at something but could not make out the conversation. I knew this should anger me, but it didn’t, I felt jealous that she would exclude me from something. He was handsome and what a man should look like I thought, I was not attracted to him in any way. I knew I was not gay but being left out made me feel like a third wheel. My mind started to drift to what would happen if Carrie wanted to bring another man into our bed if I no longer function due to all my treatments. Would she make me join them, make me suck a real cock instead of one of her strap-ons? Was that something I was willing to do to keep her happy, I knew a good MILF housewife would do anything for her spouse. This was something that I would have to think about more and do some deep soul-searching when I got home. I did love it when I sucked off Carrie before she fucked me with larger and larger strap-ons. Would it be that much different if instead of a strap-on it was a real cock? I mean I was going to be a full-on shemale MILF when I was done changing myself.

Looking around I picked up several of the magazines noticing that they were either fashion or ones geared to women. I picked up one that had the headline "How to please your man and keep him wanting more". I figured this was as good a time as any with the way my mind was still spinning with my thoughts of what would happen if Carrie wanted to bring in another man to our bed. Reading through the article I was surprised at all the suggestions that were given for a woman to please a man. Having never looked at a woman’s magazine before I wondered if all of them were like this. Was this what women had in comparison to the old Playboy or Hustler magazines for men? I did know men were more visually triggered than women. Maybe this was why women read dirty novels where men had pictures of naked women to get off to.

While continuing to read about how to please your man and all the techniques to use, I was off in my own little world. It took Carrie calling my new name a few times before I answered her. Looking up I saw Emily giggling and covering her mouth as she looked at the magazine I was reading.

“I’ve filled out all your paperwork Trista, you just need to sign them. Then Jason will take you to meet Dr. Williams, and you can tell him all about what you want done. Now come over here honey and next time we see you will look like a different person. I’m going to miss you while you are in recovery lover.” Carrie kissed me on the cheek as I signed the papers.

“Don’t worry Trista, I will make sure Carrie is occupied while you are gone. I’m sure I can find someone to help fill our time away from you.” Emily grinned as she almost taunted me with the way she stressed her words.

Before I could protest or even say anything the receptionist took hold of my hand and smiled at me. “This way miss, if you follow me, I will take you to see Dr. Williams.” The way he was looking at both Carrie and Emily had me a little worried. Was this the person who would fill their time while I was in recovery?

I followed him down a few hallways till he motioned me to enter a nice-looking office. Behind a large desk was an older man who smiled at me while looking me up and down. The look he gave me was one of admiration for the work I had gone through thus far. He waited for me to sit down in the chair across from his large antique desk before speaking to me. I tried to compose myself and not look as awkward as I felt.

“So, Trista, is it? Your fiancé and sister have been talking about you for a while now. By the looks of it, you are well into your transition. I am very impressed with your changes so far; your breasts look amazing. From what Carrie has told me they are all natural. I must talk to whoever has done your hormone treatments. I know many of my clients while not wanting to go as large as what Carrie has told me you want to go. They would love to have large natural-looking breasts without the need for implants. Enough of that though, tell me about what you want for yourself. The girls have told me what they want, it’s not up to them though. So, please take your time and be as descriptive as you can. The better picture I have of what you want the happier you will be with the result.” Dr. Williams smiled at me waiting for me to reply.

I collected myself as I thought about all the things I wanted to change; all the things I imagined my perfect MILF face would look like. I wondered if he could also help me get a womanlier body structure as well. I felt so awkward being so tall and having such wide shoulders, I knew it was going to require a lot of work. I just wanted it all done now so I could be the hot huge breasted MILF that I had fantasized about all my life. This is an important step to becoming the woman I imagined myself for so long.

As I talked about everything, I wanted my face to look like the doctor shook his head and was typing away at his computer. Nothing I seemed to say phased the doctor as I continued to go over what I wanted my new face to be. Even when I told him that I wanted to look like a middle-aged woman he just smiled and nodded to me. I felt my hands get sweaty and I felt so nervous as I let out all of my fantasies to this man. Emily had said he specialized in this kind of thing; would he think I was just a normal case like any other? Or would he think I was just some strange freak wanting all this done to myself. What kind of sane man who had a beautiful girl willing to do anything for him, wanted to instead transform himself?

More and more I described everything I had imagined over the years. I talked about how I wanted to have a smaller womanlier frame. How the only thing I wanted left of my manhood was my penis. Dr. Williams continued to take notes and only offered a few suggestions before smiling when I had finished going over everything I wanted. I was terrified of what he would think or what he would say after hearing my laundry list of items that I wanted. He continued to type for a little longer before stopping and looking up at me smiling.

“Well, Trista, you do have a lot of things you want done. Most of them I can help you with though, it will take many surgeries and will have long recovery times. As far as making you shorter, I would have to bring in a colleague who specializes in that kind of procedure. I can tell you though, it requires a good deal of recovery to shorten someone’s major skeletal structure. If this is indeed something that you are looking to have done, I can set up a consultation with you, Carrie, and her. She is quite good at what she does. Would you like to see what your face would look like from how you described it to me?” The doctor smiled and waited for me to respond.

I looked at him a little shocked and just nodded my head not even realizing that he was doing something to model what my face would look like. Was that what he was typing away on the computer, entering in the parameters as I described my face. Seeing me nod, Dr. Williams, still smiling, slowly turned his monitor around so I could see the image on his screen. The image I saw took my breath away, I just stared at it and slowly brought my hands up to my face imagining looking in a mirror.

“You could make me look like her? That…. She is beautiful, it’s just as I imagined it in my head.” I felt tears forming and quickly wiped my eyes clearing them.

“I’m glad I was able to capture everything you had in mind; I pride myself on being as detailed as I can. When I’m done with you Trista, no one will ever think you were a man. I will even do some work on your vocal cords to help give you a womanlier voice. When you come to me for a transition, I will make sure you are completely satisfied. If you have no other questions or things you want to add we can start the procedure now. You will have to stay here for the entirety of your recovery. I require this because it will be rather invasive and require constant monitoring of your progress to recovery.” Still smiling he waited for me to reply.

“No, I don’t have any more things to add or any concerns. I’m just nervous to be waking up as the woman in that picture.” I point to the monitor still amazed at the thought of looking like that when I wake up.

“Well then, if you would follow me, we will get you prepped for your transformation. I’m sure Carrie and Emily will be happy with your changes.” Dr. Williams stood up and motioned for me to follow him. As I meekly followed him, he handed me off to a very attractive nurse who instructed me to get undressed and put on a hospital gown. While disrobing I felt the cold air against my nipples making them harden. My excitement of looking like a woman when this procedure was done had my cock start to harden. The nurse let out a little laugh as she watched me try and hide my cock.

“It’s ok honey, I’ve seen plenty, and don’t worry. The doctor is the best around, you can’t even tell I’ve had some work done. He helped make me this pretty as a bonus for working for him.” She flashed me a smile before instructing me to lie down on the table. I watched as the doctor walked in now in scrubs with his face covered in a mask.

“Don’t worry Trista, this is a very normal procedure for me, and we will have you all done soon. Now just count back from ten while I give you a special cocktail of mine.” The doctor looked down and slowly injected me with a syringe.

As I started to count back, I felt the world around me start to go dark. I had only gotten to six before I was out like a light. As I lay there on the operating table the doctor went to work, giving me the face he had shown me on his computer. As I lay there asleep in my ****-induced slumber I dreamt of being fully transformed into the perfect busty housewife for Carrie. I saw myself looking in the mirror as I did my makeup. The face looking back at me was the one that the doctor had shown me. My dream shifted to me cleaning and cooking for both Emily and Carrie, I was dressed in a nice dress and had my hair done up. Next, I was on my knees eating Carrie while Emily was fucking me from behind with a large strap-on. My dreams continued to progress with more and more lewd scenarios as the doctor continued to work.