Tracy’s Transition Chapter 1

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Tracy’s Transition Chapter 1It was Halloween morning and I awoke pleasantly surprised in my pink panties. Today was the day, I had spent the last 3 weeks meticulously picking the outfit out under the disguise of the holiday it finally now was. What started off as curiosity in high school of occasionally wearing panties, stockings, and tights morphed into an over whelming desire to completely transform myself into my newly developed alter ego. Unlike most of my friends I wasn’t in college, I had lost my job AND girlfriend two months before. Had I the ability to go to the bar and meet new people I’m sure I would of looking back, but at the moment there was little to do besides surf the internet, pleasure myself, and dive straight into figuring exactly how I was going to pull this off. I had lived with my Mom who was working hard and actively dating, so it wasn’t like she was around too much to get in the way of my adventures. I was also young enough to be able to almost flawlessly transform as well, however I still hadn’t quite had gotten the hang of a sort of style yet. I knew I had at least the next 3 days to myself easily too.I had never really kept any facial hair and my body was relatively smooth as well. Thanks to it turning into Autumn I was able to keep my legs nice and smooth without notice, however the weather enabled it to be quite comfortable out recently. The night before I had tried on various things I had picked up so everything was nicely hanging up around my bedroom. I wasn’t exactly sure however on what I would wear first. I had managed to put together 3 distinct outfits, and took pictures of myself wearing each of them in a variety of possess in advance to be prepared. The first was the typical pink plaid skirt, white blouse outfit that is essentially a school girl. I had thigh high bowed socks, black flats, and some of my ex-girlfriends things I could use to complete the look. The second outfit was the French maid outfit I had picked up from the Halloween store on the suggestion of the friends I had made online that also share my fantasies. The third outfit was a pink poofy princess dress also picked up at the Halloween store, and was kind of my favorite out of the three.I ended up choosing the princess dress, and realized while I had the satin gloves to go with it I had neglected to really get anything for my legs. The thigh high socks would have to do, they at least had pink bows on them. I don’t know why I bothered painting my nails, but I started there. I raided mother’s things and selected the essentials I’d need and brought them back to the regular bathroom. It only took me about an hour to do my make up thanks to practicing, but I still felt it wasn’t quite right. My eyes screamed slut for example, and I still was in the experimenting phase of things of course. The fake lashes were the hardest to put on, and I had opted for a pig tailed look for my hair for some reason so I could use ribbons.Now that I went to the big vanity mirror, and took a minute to look at myself I suddenly though wow. Starring back at me was a creature of beauty and wonder, I instantly snapped a few pictures before I remembered that I had something that would send this over the top. I ran back to my room and ruffled through the drawer until I found the pink collar and cuff set I had bought. I attached the cuffs to my wrists and ankles, making a note to remember to leave the chains and locks on the table before I forgot. I took a few more pictures in a variety of poses throughout the house before I realized my mind was made up, this is it.I had never used the casual encounters section before, and upon further researching got a mixed review of just how effective it actually was. One thing was for certain, it seemed like the quickest way to get a few bites and attract some attention. I hesitated after reading some of the ads, but realized what would be the worst that could happen, I get some responses that go no where?I proudly started filling it out, hiding the nervous excitement. The ad was rather simple and read “Curious femme boy princess seeks to host a stud who will help me be the slutty girl of my dreams. Will you help me satisfy my craving of becoming a cock loving whore?” and attached 4 of my best pictures. After confirming it, I started getting discouraged until finally I saw it listed.The responses started coming in, but I realized I was too chicken to actually call anyone which probably weeded out quite a few more than capable people. After a while a few had started to stick out, and one in particular was quite reassuring. He had made it a point to state he had experience with gurls like me, and genuinely seemed interested. I had impulsively told him my femme name was Tracy and that I had took the pictures today, and what you see is what you get. This started fueling his fires of desire, in addition to the confession that he’d be my first experience.Once the reality of what was inevitably going to happen I started feeling a mixture of feelings but couldn’t resist continuing our conversation on instant message. I took a special picture of me sucking on a dildo just to confirm I was indeed real, and ready. I gave him my address and told him to come and get it. He lived a few towns away, so I knew I had at least 20 minutes or so before I would have to worry about what to do when he finally got here. I triple checked everything, including what I had at my disposal for toys. There was the 6 inch or so dildo I had from before, a bigger blacker one, a paddle, tape, some lubes and condoms that I had organized on the coffee table. All of a sudden I heard the doorbell ring and my heart fluttered. I rushed to the door and the person on the other side looked exactly like the picture I had been sent, I realized I didn’t catch a name!I opened the door, smiled and said “hello sir.” He grinned back at me before reply “Please to meet you Tracy, may I come in?” I walked to the living room and motioned for him to follow me. During our conversation I had told him my fears of talking due to not sounding femme enough, but he had reassured me it was ok. He sat down on the couch and told me to walk around for him and show off how I looked. I started eyeing him up and down, he had to be at least double my age with a head of hair that was showing some white. He was manly without being hairy, and had to be at least 5 inches taller than I was. He had instructed me to refer to him as either Daddy or Sir, and started rubbing the growing bulge he had in his pants. He asked once more if I was sure I was ready for this, to which I instinctively licked my lips and nodded before saying yes daddy I’m more than sure.I sat next to him and he started feeling me up and down which only fueled my passion. I stroked the bulge a little before finally unzipping his pants, and for the first time in my life touching a cock that wasn’t my own. It was quite big and thick and I begin to get nervous if I could even suck on it, but curiousity got the best of me and the girl inside took over.I got down on my knees and looked up at him, before politely asking “Daddy can I please suck your cock?” he smiled and replied yes baby and grabbed the back of my head to push me closer. At first I licked canlı kaçak iddaa it, and then managed to get the head past my lips, it tasted surprisingly good. It was then I realized when I tried going up and down like the porn movies I watched that I realized I could maybe get 3 or 4 inches in before feeling my gag reflex, however this seemed to excite him. His gentle movements of my head begin to get more forceful, and I remembered the trick of breathing through your nose to not gag. I couldn’t yet deep throat but for sucking my first cock I felt rather proud of my innate abilities. After what seemed like quite a while, I stopped to catch my breath for a minute, and play with it in my hands again. He smiled and said I was a natural cock sucker, but to keep going, so I went at it like I had fantasized and sucked like the slut in heat I knew I was. He kept pushing my head farther and farther but I could only get so much down my throat, but it was more than half. Finally without warning I felt it twitch and a warm salty load of cum filled my mouth but I was too in the zone trying to suck more and more I happily swallowed before he pushed me away from him.He asked me if I liked sucking cock, to which I giddily told him yes daddy I did. He then said in the future to say thank you sir after he cums in my mouth, to which I smiled and nodded in agreement. I sat down next to him again and we began talking, for once I wasn’t quite so nervous and let the details flow. I told him I had secretly wore panties and things for years but this was my first attempt at going all the way, and that it really excited me. He asked if sucking his cock turned me on to which I confessed that I don’t think my own cock was ever as hard as it is right now, to which he started fondling through my dress. He asked me if I had ever played with my ass, to which I think it surprised him when I confessed I had for quite a while now. He quizzed me too on what kind of clothes I had, and fetishes, to which I told him about the other two outfits and that I had been interested in Bondage and kinky things for about as long as I had been wearing panties. He finally stopped me and told me to switch into the school girl outfit I had.I ran back to my room and changed as quickly as I could, and came back. He had turned on the tv and seemed delighted when I returned to show off the outfit. I didn’t notice but the coffee table was now completely cleared off, and he instructed me to get on my hands and knees on the table. I did as asked, and felt him lift up my skirt, revealing my pink panties. He inspected me once again, before asking if I was ready for the next lesson. I happily said yes daddy, I’m ready. He pulled my panties down and started caressing my butt, before finally taking them completely off. I felt a cool sensation before realizing he was lubing up my hole, and then a lubed finger entered. I had grunted and he asked if I was ok, to which I said yes I just never liked fingers not even my own. He said to relax and next time to address him properly. I said sorry sir, and tried to get use to the finger probing my asshole. I was already quite excited before, never completely losing my erection which now stood tall.A second finger slid its way in and he started pushing them in and out at a steady pace. It didn’t hurt at all to be surprised as I was already quite use to anal play. All of a sudden he stopped and took them out, before I realized he was lubing up the smaller of the two dildos. This happened to be the same one I had sent him a picture of sucking, and it quite easily slid in. He started fucking me with it at a steady pace and I moaned in pleasure. He told me I was a good girl and moving quite along with my training. I paid little attention because I realized now that I was hornier than I had ever been, and instinctively reached for my cock. I felt a slap on my ass, and a firm voice said “not so fast, I never told you to do that yet.” I moaned and tried to not say anything, but ended up saying if I can’t touch it could you? He spanked me again, before saying “eventually, you’ll learn how to cum from just being fucked.”He picked up the pace of the dildo, and I kept begging and pleading to touch my cock. I must of said the magic word, because after what seemed like forever of begging and pleading to do anything to touch it he finally agreed that I could. Within a few strokes I came hard and shot the biggest load of cum of my life all over the table. He spanked my ass a few times scolding me for not asking permission to cum. I didn’t care too much, I was in my post orgasmic bliss trying to adjust to the fact he hadn’t stopped a beat with the dildo pounding my hole, which begin to feel weird for a change. I finally said sorry daddy, can you please take the toy out of my bum? To which he said yes, but you’re going to have to get used to it eventually before slowly pulling it out with a pop. He sat down, and I motioned to get off the table but before I got very far he told me to lick up my mess. I had been used to the taste of my own cum, but licking it up like that isn’t quite easy either however I obliged. I did my best to do it as seductively as possible, like some of the videos I’ve seen featuring the act. He finally said I was done, and I got off the table and went to the kitchen to get a drink. I asked if he would like one and again forgot to say sir or daddy, to which he questioned if I had a beer. I told him I didn’t and started giving him a list of what I did have, before he just decided on water. I brought it to him, and sat next to him and realized that it was nearly 2 in the afternoon.We casually started talking again, and he started going off on his own history. He was divorced and owned his own business but didn’t explain what it was, and I finally asked why he was interested in girls like me. He hesitated before giving a response on how after the divorce he found most girls to not be the submissive types he was looking for, and that he had quite a high sex drive. He said he was still straight if the “boys” were dressed as and wanted to be girls. I had never thought of it liked that, but didn’t feel the need to comment either.The subject of kinks came up soon after, and he started quizzing me about ones I had done, and ones I would like to do. I admitted to experimenting with some bondage and kinky play in the past, but found rather than being the one giving it I had wanted to be the one receiving it. He smiled and said I noticed your collection before. He admitted to being quite involved with Bondage and being a Dom, even confessing that it fueled his sex drive. He took great detail to explain some of the things he has and has done, to which I caught myself curiously listening to every detail. We talked for almost an hour, before he caught me off guard and asked me when my parents would be home and if I was worried about being caught dressed. I confessed that my mother worked full time and had a serious relationship and it wasn’t unusual to not see her for days at a time. I asked him if he had any place that he had to be, and what his time line was. He at first simply said no, before saying that he usually schedules a few hours for an initial first encounter.He canlı kaçak bahis paused and explained that no two are ever the same, going on to give some details on how some would be too scared or others would simply just not want to really enjoy what he was looking for. He did admit that he had trained about a dozen or so of what he called girls like myself, and then began questioning me about what I was looking for out of doing this. I confessed I was a horny lonely boy and this had been stuck as one of my desires sense I lost my girlfriend, but beyond the initial experience how I hadn’t quite thought that far yet. He told me we’d talk more about that part later, but asked if I would like to do this again after today, to which I immediately without thinking said yes yes I would. He smiled but remained silent, before asking me to try and get a hold of my mother to make sure she wasn’t coming home anytime soon.I walked back to my room to get my cell phone, and surprisingly when I called she answered. She went on to tell me that she was at work until 5 and had made plans to go out with her boyfriend and would more than likely be staying there. She reminded me there was food in the fridge and told me to stop wasting my time watching porn all the time and actually go and do something. I tried my best to not laugh when she said that and told her I’d talk to her later and to have fun.When I was done with my phone call, Daddy said he had to check a few things but his phone was in the car. I didn’t pay any attention to it really, and didn’t quite notice until I snapped back into reality and noticed he wasn’t there. I looked outside and his truck was still here and he was sitting in it on the phone. I started to try and watch tv but my mind was wandering all over the place, until finally he came back in.He told me he was just making sure he wasn’t needed at work right now, and said he’d have to go somewhere at some point. We talked some more before he asked me if I was ready for my punishment. It shocked me, and I asked him what punishment? He reminded me I did a few things without permission, but admitted he’d go easy this one time. I didn’t quite realize that he had my paddle in his hand, but he told me I was to be spanked for my transgression. He grabbed me and positioned myself over his lap, and lifted up my skirt. He told me to count each one and say thank you daddy. I was to get ten, and the first one really caught me by surprise. After each one I’d groan a little, count the number it was, and reply thank you daddy. After the last one he asked me if I learned my lesson to which I had just nodded, holding back tears from the rather surprisingly painful spanking. I hadn’t quite noticed but apparently spanking me turned him on again.He asked me if I was ready to give him my virginity, and I immediately told him yes daddy, but my butt hurts after that spanking. He told me well next time don’t earn yourself a spanking. He started asking me about how many people I had slept with, and if I had any STDs. I didn’t, and admitted I had just figured he’d use a condom. Now that I would be his however, he told me there was no need. I asked him if he’d like to move to the bedroom, but he told me no. He handed me an enema and told me to make sure I was still clean. I rushed to the bathroom, and came out a few minutes later. He instructed me to get on the table again, except this time he was going to fasten my restraints. Stunned I asked him why, before he explained that sometimes the first few times can be difficult until properly trained. I got back on the table on my hands and knees and he fastened the restraints, including my collar to the table. It surprisingly turned me on, but I never expected my first time like this even if I also wanted this.He pulled his clothes off but I could see him directly, concentrating on the reflection of the picture window. Anybody walking by would be able to see but that surprisingly didn’t make me worried. He came around to where I could see him and told me simply to suck. I opened my mouth and he started pushing it in and out, causing me to gag a few times but not really fucking my face either. He returned to behind me, and lubed up both his cock and my asshole.His cock was quite a good size, with a slight curve up unlike my toys. I felt the tip of it on at the entrance to my hole, before he asked me if I was ready. I simply said yes sir, only to get asked a ready for what. I’m ready for you to fuck me daddy was my response, and he asked me again if I was sure. I said yes daddy, I’m sure please put your cock in me please I started to plead.He started pushing it in slowly, and finally it gave and slid in. I moaned and yelled oh fuck a few times, and he didn’t move. He slowly started moving it in and out and I kept repeating the oh fuck, surprised at to feel the stretching burning sensation once again. He told me to relax and that it was normal considering I was a virgin. He slowly picked up the pace and frequency of his thrusts in between telling me how tight I was. It started to feel good, and I started moaning more in pleasure rather than pain. He noticed this and asked me if I liked it, and I screamed yes. He asked what I liked, and I moaned that his hard cock felt good in my ass. He picked up the pace and was slamming into me, and I was moaning like a bitch in heat trying to egg him on. I kept telling him to fuck me harder, and he would keep telling me how good I looked with his cock in my ass and that I was being a good girl. He started pulling completely out, pausing and slamming it all the way back in. I noticed a strange sensation building inside me and kept moaning in a trance, it felt so good. Without warning, without touching I came burst after burst, almost exactly synced up with his thrusts in me, my whole body shook and I screamed and moaned oh god. This was exactly what he was looking for I think, because I felt him twitch and cum deep inside me.His cock pulled out with a pop, and I felt something leak out of me. I was in a trance, stunned and out of this world. He told me that was one of the best first fucks he had ever had and that I was a natural. He undid my restraints but I was still coming back to earth from cloud nine. Finally I said “that was amazing daddy” and he smiled and nodded. He told me sense it was my first time, to just put my panties back on. I did and sat down on the couch, while he dressed himself.He asked me if I enjoyed it, and I immediately said of course. He locked at the clock on the wall and noticed it was coming up on 6 now. He had a few errands and things to do, but said he’d be back before the night was over instructing me to wear only lingerie and stockings this time. I asked him how long he would be but he avoided answering, and started texting on his phone. We exchanged numbers and he leftI didn’t move in inch after he left, laying on the couch in a daze I had never yet felt. My mind couldn’t focus on a single thing besides replaying that moment. I wasn’t sure how long went by but then the doorbell rang. I expected it to be daddy so didn’t even check and opened it to find trick or treaters. Mortified I immediately closed the door and panic set in. I went back to my room bahis siteleri canlı and started talking online to some of the friends I made who had given me tips about all this to find they were both proud and glad I had such a wonderful time. My inbox was filled with people who wanted a piece of me, and for once I felt like I was truly worth something.I went into my mother’s room and picked out her white bridal lingerie. She was expecting to marry her boyfriend eventually and got it on sale. Little did she know I was about to borrow it, but it surprisingly fit and I looked pretty in it. I noticed it was getting quite late, and curiously flirted with some of my new found admirers. I wanted more of course, and was getting antsy waiting so I started the hunt on who could fulfill that need.All of a sudden I hear the door open, startled I run down the hall to check who it is not thinking what I was previously doing. Thankfully it was Daddy and he was pleasantly surprised with what I picked out. He told me I was a natural at this and surprised me when he asked if I would like to move to the bedroom. I didn’t think twice and showed him the way, and quickly got on the bed. He looked around the room a few times before undressing and laying down himself.I immediately started playing with his cock, and graciously started sucking him before he was hard. It didn’t take long for him to get erect from my efforts, and when he was nice and hard I stopped, looked him in the eye and asked him if I could ride him. He nodded and I got on top of him, and without using any lube besides my own spit and his previous cum started riding him. It felt good, and I moaned a few times, trying to act as slutty as I could. After a few minutes I started getting tired, and asked if we could try another position. He agreed and instructed me to get on my back he had a surprise for me. I layed on my back with my legs stretched towards my head like the movies I had seen, and he wasted no time getting back to business, fucking me slow and steady and hard and rough. He grabbed my rock hard cock through my panties and started rubbing it in the lacy fabric, fucking me harder and faster before finally I came. He didn’t stop and kept going and going before finally cumming himself once again inside me. He instructed me to push his cum out, and he collected it in his hand and fed it to me. I happily licked it off his fingers and thanked him. He pulled out something from his bag and showed me two things. One was a bag of clothes he wanted me to wear our next encounter, and the second was a chasity device for my cock. He told me now that I was his, he would control my pleasure. I lustfully agreed and let him put it on and lock me in it. He got up to leave after he tucked me into bed, and starred at the computer screen. He didn’t say a word but I know he saw what was on the screen, and shut the bedroom door and left. I drifted blissfully to sleep in a state of exhausted bliss in the once pristine lingerie, not really giving a damn about anything.The gravity of what had surprisingly actually happened didn’t hit me immediately upon waking up sometime late the next morning, in fact I could of sworn it was a dream until I realized my cock was locked away in its plastic cage, aching against its confinement. Slightly confused, I realized what I was wearing and immediately took it off and hid it in the back of my closet. I spent the morning frantically trying to hide any evidence that something out of the ordinary had happened, and quickly went back to my room. It was then I realized the bag of clothes laying on my bedroom floor but instead of opening it I went straight to my computer and did my best to decompress and pretend that everything was normal.Surprisingly as I reflected instead of being revolted I was a mixture of excitement and proud. I was strangely horny with no way of release, and wondered when I’d have my next encounter with my new Daddy. I remembered the clothes and decided to check em out and try them on. It was a wet black vinyl set, leggings, gloves, panty, bra and micro skirt with a buttplug and a letter inside. The letter was a Contract that was void unless signed by 5pm Sunday evening, it was Saturday around noon, that pretty much was what we had talked about the day before. It essentially was a Slave Training contract that gave him full control and permission over myself for feminization over the next 30 days. That’s when it hit me, we had yet talked about my own future and feelings regarding such.I tried calling him but it went to voicemail, and I hesitated before leaving him a message. I ended up checking my email, and seeing if I could get a hold of him online, considering we had arranged things at a similar time the day before but the day dragged one with no answers to the questions. Mother came home but I had managed to avoid her by faking a nap, and she had been rather brief in her layover before venturing back out. The messages of interested people wanting to know more from the ad she had posted yesterday kept flooding it, with nearly 100 sense I had last checked em. Out of pure curiousity and boredom, in an effort to re-examine the desires and see for myself just how seductive I could be I responded to many of them. Most were horny men looking for quick relief I noticed, some were fake, but none that had stook out like Daddy had. I ended up taking some pictures of the outfit, and in an effort to be bold sent them by phone. Surprisingly it was only a few moments later that the trickle of messages came back. He was mad about what he saw, not for the courage and desire, but for the fact I did it without asking if it was something I could do.He had changed his initial plans for the weekend, deciding to take on full advantage of the fact I was alone and at my house for the weekend, curiously exploring my girl sexuality for the very first time. Instead of bringing me to his house like he was going to, he decided he had an assignment for me. He made it very clear, unless he had told me not too, that I was to use a condom for every person I was to pleasure. This only included being penetrated, I could suck and was expected to without one.I was given no control however over this ad, as he was going to personally create it. This meant I had no idea who was coming, and none the less was expected to look as passable as possible. He told me that when the doorbell rang, I was to great them and invite them inside. They would be sending pictures back to daddy to make sure I complied. If they came in a condom I was supposed to save it in the freezer. I was stunned but also jumping with excitement, curious on what was in store. It was nearing the middle of the afternoon and due to being locked away no way to stop the building budding feelings coming and going as they willed. A text came in, giving the only advance that people would start coming within the hour, and to pleasure them as they saw fit and to do it as seductive, sexy, and feminine as possible. I went into the bathroom, and took a quick shower and did my make up in a dark slutty fashion. In the black wet vinyl outfit I really did look like a fetish model, but the cage on my cock gave an unsightly bold. I wasn’t passable and that was the point, I was a girly looking boy whore and it surprisingly only turned me on more. I gathered all the condoms and lube I had, which worried me as I only had most of a box. I started to wonder just how many people I could actually pleasure.

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