A Sissy Fantasy

One day my girl decided she was in the mood but wanted me to shower first. As I procceded to head to the bathroom she told me to wait & came up behind me to hand me a bottle of nair, she said "I want to see what it's like with you bare and I mean everywhere". I took the nair without asking any questions, despite my confusion in her unusual request. As I am actually getting in I hear her add, "clean yourself out too, I want to use some toys". I had never used nair everywhere before but had always been curious and wanted too just to see of I could pass while crossdressed but hadn't the courage before. Once I was sure there was no body hair anywhere and I was clean inside I got out and headed to the bedroom. I was surprised to see my girl with some bondage gear and several hancuffs, she told me to lie down and placed a blindfold over my eyes. She continued by handcuffing my wrists to the bed, she then told me to lift my legs and I felt her stick something under me before strapping my thighs into something that kept my knees up towards my chest and spread apart. It had been quite a while since she was willing to do anything kinky and I felt like I was in a dream, but the kinkiness didn't end there. She told me to open my mouth and relax to which I complied only to realize she was putting around a 7inch dildo down my throat followed by being fastened behind my head like a gag. I had to relax and focus on my breathing so I didn't notice when she placed something on my chest. Next thing I noticed, drawing my attention from the phallus shaped toy blocking my airway, was that what she apparently placed on my chest were cups to a breast pump as she turns it on and it begins trying to milk me. Then I felt a set of head phones go over my ears, I hear her say "I love you now just relax". She turns whatever she has plugged into the headphones on and it sounds like soothing noises for sleep, it blocks out the noise of the breast pump and everything else, even my thoughts it seemed. She rubbed something on my genitals then pulled her hands away, it began to tingle then after a minute or so I felt nothing down there like I was numb. I could sense she was doing something again based on the movement on the bed but couldn't feel anything until I felt her lubbing up my asshole. I could faintly tell that I was getting aroused yet it felt as though something was preventing it, I wondered for a moment if perhaps she had placed a chastity device on me. Not another thought entered my head as something entered me, opening me up and pausing my mind for a couple minutes before it was pulled out. Suddenly the audio changed and I slowly came to the conclusion it was a bunch of random male grunts, moans, and dirty talk directed to women, I didn't notice at first but something bigger began to enter me. I have used plenty of toys in the past and even some decently big ones but none felt the way this did. The weight on me and the bed suggested to me my girl was using a strapon but I couldn't shake the feeling it might not be a strapon. Regardless my mind went blank as I began to get fucked, without any thought I was feeling things I hadn't felt before. A warmth inside my ass grew as I lay there bound and gagged listening to the sound of men getting pleasure or calling 'me' names, feeling myself tighten around this feeling, becoming lost in it. It felt like something was released inside and I felt more slick inside with what felt like slight sudden vibrations were turned on to push me over. I felt it, what I dreamed of but mever achieved before, an orgasm from getting penatrated alone, granted everything else going on but in my silent mind I could only picture myself getting fucked. My hips quivered a bit as I felt this new found euphoria followed by a sudden feeling of emptyness quickly resolved by what had to be a dildo shaped plug. The audio returned to ocean waves or other nature noises. I lay there not thinking still feeling like I was in a dream, no comprehension of time at all. When my mind came back I could feel the headphones being removed, I noticed the breast pump must have already been turned off and removed. My legs were freed, then my wrists, followed by the gag which I had practically forgotten about until it left my throat. I removed my blindfold to find my girl standing over me beside the bed with a smile lile she had been pleased beyond any of our other bouts of sex. As I sat up I noticed the way my chest looked pumped up, followed by the memory in the back of my head that she had somehow confined me but I never felt it removed same as the breast pump. I look down and am surprised as I don't see a chastity device, nor my appendage. I look up at her in shock and she reaches her arm out to calm me as she sits beside me. "Don't worry it isn't gone completely, I just used a bit of medical glue and made you look better suited for the role you played tonight. It should wear off in a few days or so but I think we both liked it so much maybe I'll just have to fix it as soon as it wears off, what do you say"? Still in disbelief of everything that had just occured, I nodded in agreeance. Little did I know exactly what I had agreed to as I had to form the habbit of sitting while I used the bathroom and whiping instead of just shaking. I had to keep up with my hair removal and she told me to grow my hair out now. Granted I enjoyed it all very much, but it was a bit to get used to with no idea ahead of time. As time went on this became increasingly more frequent of a thing, at first at least once a week, then twice, thrice, and so forth until it was daily by the fourth month of it all. I had grown accustomed to my grooming and sitting in the restroom, the only time I actually had my genitals hang out was to clean them then my girl would put them right back in place, I hadn't even been able to get hard in all this time. The other thing new to me was it seemed the breast pump has taken effect on me as my chest had gotten a tiny bit bigger & more sensitive, especially my nipples. Anyway after all this realization after that night when things were done and I was plugged and freed of all the bondage she gave me a gift bag and told me to open it. I caught off guard even with everything else to pull out a set of lingere while she whispered "I want you to put it on for me". She helped me get everything on, it was a cute yet sexy red and black set complete with a corset, push up bra, panties, garter, and stockings. When we were done she grabbed my hand & pulled me to the bathroom where she had all her makeup out & a chair. She sat me down & without a word began to work as I sat stunned. After some time she said she was done but before I could look in the mirror she pulled out a box that looked like another makeup kit or something. It ended up being a mani pedi kit & she got to work on me. She made my hands look amazing & painted my nails to go along with the lingere, next she removed my stockings to do my feet. When she was done instead of letting me look in the mirror she a VR set on my head with a headset as well. She turned everything on and suddenly I was at the beach listening to the waves once again. In this VR world that looked so real a handsome shirtless guy walked up to me and without a word lost in it all I descended to my knees as he pulled out his big cock. I grasped it gently noticing my hands with the fresh manicure and nails as I begun to stroke. I leaned in to breathe in his smell, I felt like I could really smell a man's musk and could actually feel the skin on his member along with the twitches at my touch, I chalked it up to post sex euphoria from me and my girl as I stuck my tongue out in tike to catch a bead of precum leaking out the tip. As soon as I tasted it I was lost in my actions, I took the soft head in my mouth and gave my first actual suck on the tip leading to more of a reward. I eagerly began sucking as an even tempo while my hands dropped to my thighs, to this he stuck his hand on the back of my head suddenly applying pressure to encourage me to go down further. I opened up my throat and with astonishing ease had my lips anound the base of his cock, my chin pushed into his scrotum and my nove shoved into his abdomen. Now he was no longer inclined to hold back as he held my head in place and he noticed I could actually still manage to get a breath with him shoved down my throat. He said something but I can't remember as the waves drowned him out, then he began to buck his hips like a stallion in heat, pulling out to the tip before plunging back in. I felt his nuts swinging into me and warmth build up inside me once again. I don't remember him ever giving me a break as he pounded away, all I do remember is when I was woken from my state of bliss to him pulling all but the tip out as he filled my mouth. My lips wrapped tightly around his cock head as I sucked enticingly for every last drop. He pulled away from me and I heard what sounded like my girl's voice say "good girl, now why don't you hold that till he walks away then swallow it all down". I watched as he pulled his shorts back up walked off into the distance. I swallowed his seed and abruptly had an orgasm. Immediately after I stopped shaking from my orgasmic bliss the headset and VR were removed and I found myself sitting in the chair in the bathroom once again. My girl asks if I'm happy with her work, without a thought I nod thinking about the VR trip but then she says "good, I'm glad, now I want you to keep your feet like that too and go ahead and put your stockings back on". I was pulled from my happy daze realizing we were on different pages but looking down at my feet with matching polish to my fingernails I was releieved I agreed on something haphazardly that I was still enthuzed by. She finally let me look in a mirror and I was shocked by the beauty staring back at me, I almost thought I was still weqring the headset. My girl spoke, "If you like it then I will teach you and you can do it whenever, I will even buy you your own kit, but this will be something before sex ok"? I couldn't hold back as a hugged her tightly and agreed, profoundly grateful thanking her about a million times. She said it was great I was happy and that she had one more thing to add when I was done in the bathroom. As she left I couldn't stop admiring myself a little longer in the mirror when I noted the taste of cum in my mouth. It seemed odd as it was just a video, maybe the audio had something to do with it. I came out and she put a workout video on on the tv, it was all women and focused on yhe glutes, she said "time to get that plump booty into a fine ass". And worked me like a sled dog before showing me a diet plan to end our night. Now fast forward to the end of the sixth month of the start of all this. I can definitely tell that I have developed breasts to an extent and that my nipples were much larger than the start. I kept up with my grooming but found less hair growing in as well as it taking longer to come back. I felt different mentally too but it was a good different. I had painted toenails at all times and if I didn't work my nails woukd be done up too. My butt was getting into great shape and filled any of my now numerous pairs of panties as I no longer wore boxers, it just felt right anymore. It had been a long time since my girl got in the shower with me but she told me she wanted to today before sex time. The medical glue had worn off and my genitals were out and she pointed out that I was noticeably smaller now. I was surprised when she got on her knees and started trying to get me hard, but I was more surprised that even though I felt I was beginning to be aroused that I remained limp. She got up and shrugged before getting out of the shower. After drying off I did my own makeup as she had taught me then put on a new lingere set. This set was basically *** same as the first except the ass was open and so was the bust. She handcuffed me and blindfolded me but when she went to place the gag I noticed ut was a bigger dildo than usual, it still slid in with ease but reached greater depths requiring me to focus as much as I did that first night. She placed my legs in the bondage, now very well spread and further back than at the start, placed the pump on my breasts and turned it on. Next was the headset and audio but before she turned it on she warned "you may feel a pinch before you go numb tonight sweetie but don't worry". Then the waves began. Instead of a rub of the numbing gel, which was no longer necessary to prevent an erection anyway it seemed, I felt the pinch she warned of. I probably would have second guessed it if I didn't have the headset on, taking me away. I have no idea how long it was before she removed my plug but all the same I was excited when she did, only to be surprised when she placed it back in. Then she removed the blindfold in order to put the VR device on me. The waves stopped and suddenly alot of things began to make sense. On the VR screen I saw our room and our bed, followed by her leading me in that first night. Everything went how I understood it to until the part where she lubed me up for the dildo. I could make out that someone else had entered the room but I couldn't see them yet. After my girl used the dildo I saw her get up, then the figure came into view. It was the guy from the beach in the VR set, he was naked and climbing onto the bed over me. Now I know why it felt so different when my girl used the new strapon, it was this guy's dick inside me these past 6 months not a toy. Even though I was shocked I enjoyed the show anyway. When he stopped and got off I could tell he filled me with his cum and I felt happy to know this. Then my girl held 2 things up so the camera could see. One was the buttplug, the other was estrogen suppositories, she pulled one out and stuck it on my hole before sending it home with the plug, no wonder she kept me bound for so long after "our" sex. The screen changed to our bathroom with me stting there with makeup and the lingere set and the VR on me. My girl moved to the side as the guy walked in infront of me, shortly there after I could tell I got down on my knees and did everything I remembered, straight down to sucking every drop of cum out before he walks out. I see myself swallow before sitting on the chair again and then the screen goes dark. "Now for the shocker" I hear my girl say as the screen turns back on to this very night. She just finished everything before warning me of the pinch, the guy walks in with a needle and injects something into me. My girls pulls up a light and metal tray as the guy puts gloves on, the scene was the biggest shock of all. The guy grabbed a scalpel and cut my scrotum open, he worked until I saw him pull one of my testicles out, followed my the other, I could barely watch at this point but I do as he sews me back up and walks off. The screen goes black again and my girls removes everything. "Be careful not to move too fast or you may open up your incision. I slowly get up in sheer disbelief as I look down at my shrunken little clit of a dick and empty package. Then I hear a man's voice say, "don't worrt baby I'm a doctor, I know what I was doing and will finish the job when you are ready, also I'm sorry but no sex for a bit okay? But you can make it up to me with a blowjob". I can't tell you how or why or what I was thinking but right now I'm on my knees with him fucking my throat, trying to get his third load down my throat and I couldn't be any happier.