The Transformation Of Me free porn video

TG fiction by [email protected]. This contains very graphic adult sexual content. If you are offended by transgender, crossdressing, or other themes, I encourage you to read something else. Feedback is always appreciated. Story requests are sometimes granted. My email address is above. - Copyrighted 2015 by George Wilson ============================================================== My top is making me write this history, in hopes that some other boy will be inspired to carry on my footsteps. It all began, innocently enough, with Yazmin. Yazmin and I went out when I was in High School. Being from the middle east, we had "old fashioned values". This meant that intercourse before marriage was forbidden. In fact, if we were back in the "old country", we could have been stoned to death for it. Just because intercourse wasn't allowed didn't mean we weren't sexually active. We did everything BUT break her hymen. And that's where this story becomes my adventure. On the weekend before our Senior Prom, we were naked in her bed, fooling around. Through my own clumsiness, I accidentally came very close to her opening while petting her with my cock. Another fraction of an inch and I would have been inside her, and her hymen would have been sheared away. She freaked out, and told me we couldn't be completely naked at the same time until we got married. Since we were both planning on going to college, that meant a 4 year wait, longer if she made it into medical school. I figured that I would have to just be happy with her incredible mouth pleasing me for the foreseeable future, and she'd have to be happy with my talented tongue. On Prom night, it's traditional that the couple exchange flowers. In our ethnic tradition, it's common to have a chaperone. In this case, it was to be Yazmin's father. But, when I arrived at Yazmin's house, I was told that I could forego the chaperone on one condition. The condition was handed to me in a pouch. I was told to go to the bathroom and open the pouch. I did as I was told. Inside the pouch was a number of plastic rings, a plastic tube obviously meant to encase my penis, some posts, a tiny bottle of lubricant, a lock, and directions. I carefully examined the pieces, test fit them together, and then fit them to my cock. When I came out, her father told me to go back into the bathroom, where he examined my work. Finding it acceptably tight, and not likely to be removed, I was allowed to take Yazmin in my car to the Prom without a chaperone. He collected the key from me and put it into the pouch with the extra parts. In the car, I explained what was on my penis. She said she suggested it to her father, who acquired the device, called a "curve". She said he was holding the keys. I was heartbroken, but figured it was for only one night. At the Prom, I found it pinched a bit when dancing, but was otherwise fairly comfortable. When I needed to empty my bladder, the numerous holes in it allowed that to happen effortlessly, even though I was forced to sit down to pee. When I returned Yazmin home, I asked if she could get the key. She said she'd see me in the morning with the key. I went home and slept with the device preventing me from masturbating. In the middle of the night, I had an erection. I thought my balls were going to be ripped off my body. I drained my bladder, sitting on the toilet, and sprayed cold water on it to get it to go down. The next day, Yazmin called to say she had the key and was on her way over. When she arrived, she wouldn't open the lock until I gave her three orgasms using my tongue. By the time she had that third orgasm, it was hours later. She needed to go, so she tossed me the key. I found out the key didn't fit the lock. I called her, she said that was the key in the pouch, She said she'd ask her father for the real key. Later that night, she said she had the real key, and would bring it over the next day. The next day, Yazmin demanded her two orgasms. My tongue was especially tired by the time she had the second. I asked for the key. Instead, she opened the lock using the key. She told me that she liked the device on me, and that it would remain on me except for brief periods when she removed it to allow me to clean myself, or for her to give me a blowjob. I objected. She told me I had no choice if I wanted to continue to go out with her. Since I loved her, I agreed. She had me clean myself, and then gave me a mind blowing blowjob. I came so much she gagged as she tried to swallow it all. Afterwards, she said that guzzling two days of cum was very exciting for her. She then suggested waiting three days to release me again. I reluctantly agreed after she said she'd be over every day to collect her orgasms. She watched me put it back on, and then checked it to make sure it was secure. Each day, Yazmin and I met and I orally pleased her. On the third day, she gave me another mind blowing blowjob and swallowed my huge load. After I was locked up again, she said she wanted me to go a week. The daily oral supplication to her pussy continued. On the seventh day, I cleaned up and got my blowjob. I came like a burst dam. My cum was seemingly never ending. Yazmin gagged under the heavy thick load, and had what I thought was a spontaneous orgasm during it. She was estatic. She pronounced the "curve" as the greatest invention ever. Of course, when I left her home, I was wearing it. Each day, we'd meet and I'd attend to her pussy. Sometimes one, sometimes two, and occasionally three orgasms before she'd say she was satisfied. At the end of the week period, she let me out to clean myself, but told me I had to wait until her period started in a few days for the blowjob. And that, from then on, I'd be allowed to clean myself once a week, but blowjobs would be during her four day "heavy" period. I'd get a month of weekly blowjobs in four consecutive days. I didn't have much leeway to complain about this arrangement. As the end of the summer approached, Yazmin was excited about going off to college. I was staying local. I assumed, when she went to college, she'd just give me the key and we'd pick up where we left off when she returned for the Holiday break. The night before she was to leave, she took me to a house I hadn't seen before. We went to the door and were greeted by a tall blonde woman. She was what one would call an "Amazon". She was wearing tight clothing that showed she must be a body builder. Yazmin introduced her as "your new key mistress" and handed her the key! Before I could object, the Amazon told me her rules: 1. Privacy: I was to be discreet and not draw attention to her or her home or myself when entering or exiting. 2. Preference: She prefers women and I was her first male submissive. I should not expect to put my "nasty cock" into any part of her, or expect her to have sex with me. 3. Yazmin's rules: I was not to be permitted to masturbate. I was not permitted to have intercourse with any woman. I would be permitted to be released once a week to clean myself. 4. Name rule: I could call the Amazon "Katie" or "Mistress" or "Goddess". 5. Orgasm rule: I would be expected to provide payment in the form of orgasms for the Amazon. I objected and demanded the key. The Amazon laughed. Yazmin gave a nervous laugh. I again demanded the key. The Amazon told me to arrive between 6 and 6:15 every Friday. If I was late, I would have to wait another week. And then, she pushed me out the door. Yazmin followed and the door closed behind us. I expressed my dissatisfaction with the arrangement to Yazmin all the way home. Eventually, I begged her to re-consider the arrangement. She was steadfast and explained that she wanted me to be chaste for her, and not fool around with other women. This arrangement guaranteed that. I threatened to cut it off. She told me that she wouldn't be with me if the key didn't fit when she got back in three and a half months, or the device was missing entirely. When I got back home, I thought about it for five days. That Friday, I went to Amazon Katie's house at precisely 6pm. She let me in, and had me strip naked in her foyer. I was then permitted to follow her upstairs to the master bedroom. The bedroom had a huge four post bed, with restraints on every post. There were also padded wooden tables, an X shaped cross on the wall, some kind of suspension harness hanging from the ceiling, and even more restraints. She asked me if I was prepared to provide "payment". I said I was willing to give her the weekly orgasms. She had me lay on the bed, attached cuffs to my hands, and took off her robe. Underneath the robe, she was all muscle, except for her torpedo shaped breasts. I looked down at her pussy. She had a HUGE clit. It stood out from her labia like a small cock. I think I may have started drooling. She noticed me staring at her pussy and told me that she got it so completely smooth and hairless by using a home laser system. I was actually looking at the number of rings that were hanging from her labia, which accentuated her huge clit. I had never seen anything like it. She got up on the bed, threw a leg over my head, and then "mounted" my face. She gave me instructions on doing a better job, including how to properly suck her clit. She mashed her pussy hard into my face when she finally came after at least 30 minutes of work. She told me that Yazmin extolled my oral skills and she wasn't lying. I felt pretty good about myself at that moment. Amazon Katie unlocked my cock, cleaned it for me, and then re-locked it. She then unlocked the cuffs and told me to get out. I wasted no time leaving. The next week was a re-run of the first until Katie went to lock my cock back up. She told me that I needed to be shaved down there. The next week, I arrived, re-ran the same sequence, but she wouldn't lock me back up. I had failed to shave. Since I had failed to shave, she would do it for me. I had a choice between a very scary straight razor, or I could choose to have the hair lasered off. I chose the laser. She explained that I would have to stay over-night, as the laser makes the skin tender. I wouldn't be able to put the cage back on my cock until the next morning. When I told her that was ok, she said she'd extract additional payment for her services. The lasering itself wasn't unpleasnt, although the sound did get to me. When she was done, about 45 minutes later, I was allowed to look. My whole crotch was bright red, as was the root of my cock. She pressed against the red skin. It was tender, just as she said. She spread some kind of ointment on it, and it seemed to help. Katie put a spreader bar between my knees, which she said was to prevent me from using my legs to masturbate during the night. After extracting a second orgasm by riding my face, she cuddled up with me and we fell asleep. When I awoke the next morning, Katie was doing push ups on the floor. She released me from the knee spreader and the cuffs to go to the bath room. I was reminded I should sit to pee in her house. I was required to leave the door open and she watched me. When I was done, I cleaned my cock, expecting the cage to be put back on immediately. My cock was still tender. Katie gave me a squirt of the ointment which I slathered over the now bare areas. Katie informed me that I wouldn't be leaving without the cage, but that might not be until evening. Until then, I'd be cleaning her house. And, so that I didn't get any ideas, I'd be wearing a pair of pink panties while doing it. She stood behind me all morning with a riding crop, ready to swat my pantied ass if I didn't do a good job. For lunch, I was to sit on the floor. My head went into a special chair that Katie sat on. I looked at her ass and felt the rings through her labia on my face while she had a leisurely meal. When she was done, I was allowed to kneel before her as she sat on the chair. Her thighs crushed my head as she came from my oral attention. She allowed me more ointment, and then she put the cage back on. It was a little painful. She kept my underwear, and gave me the panties to wear home. When I went to put on my pants, I found it very painful. I told her it was too painful. She suggested I wear one of her skirts. Not only was that not going to press the area, it would also keep her reputation as a lesbian intact. She didn't like the idea of me leaving during daylight hours in my "boy" clothes. If I wanted to stay, on the other hand, she said she'd do something very fun for her, but something I might not like at all. She didn't say what, and I was actually too afraid to ask. I accepted the skirt. She added a pink "Girl Power Gym" sweat jacket, a tiny purse, and some ankle socks to my wardrobe. With my long hair, anyone at a distance would think I was a girl. But, Katie wasn't satisfied. She put lipstick on me. Handing me the lipstick tube, she suggested that I might get a very special reward if I left my clothes here and wore the outfit back on Friday. I told her I'd think about it. I was somewhat curious as to what the very special reward might be. So, on Friday, I put on the short skirt, the pink panties, the girl power sweat jacket, and a light T shirt and made it over to Katie's. She smiled when she saw me. I was told to go upstairs, and leave on the clothes. Upstairs, she cuffed my hands to the bed and rode my lipsticked lips to a furious orgasm in under five minutes. When she dismounted my face, she lifted my skirt and then pulled my panties off. She stroked my caged cock. I couldn't feel a thing. She asked if I ever did anal play with Yazmin. I told her that Yazmin was repulsed, so we didn't do it. She smiled and reached for the bottle of lube. At that point, I realized she meant MY anal and I told her I was uncomfortable. She said she had a lot of practice and I'd enjoy it. If I didn't enjoy it, she'd give me the key. I agreed, under that condition. I figured I was home free with the key. All I had to do was say I didn't enjoy it. She put a finger into my ass and pressed a spot. I thought I was having an orgasm. Cum dribbled from my caged cock. She began to massage the spot, and I really did have an orgasm. She didn't stop massaging and I didn't stop cumming. After a few minutes, I felt some pressure down there. She had put two fingers inside me and was alternating tapping the spot with the fingers. The orgasm continued. After what seemed like forever, she withdrew her fingers and asked if I wanted the key. I told her no. She released me to clean myself up. Despite being in a cock cage, I had had a machine gun orgasm the likes of which I never experienced. The proof was in the puddle of cum on me and the bed. After I was clean, she re-locked my cage, and forced me to change the sheets on the bed. After the last time, I figured I'd be staying the night, but she said no. She said she may have scratched me inside, so I should take anti-biotics for the next week. She gave me a bottle and told me to take 3 tonight, 3 tomorrow, and 2 every day until Friday. She also put a suppository into my ass, which she said would help it heal. She said I might have sore thighs or tenderness in the breasts the next day, if I was actually injured. I left in the girl clothes, after Katie put lipstick on me (admonishing me for not remembering to bring the one she gave me back). She said that if I raised the bar on my outfit, she'd consider another special reward for the next week. During the week, I went out and bought a sheer blouse, saying it was for my girlfriend. I also shaved my chest hair. My nipples were a bit inflamed all week, but my thighs didn't ache at all. When I arrived at Katie's, she was all over me. We didn't make it upstairs. Instead, she took me to a first floor room that had a medical theme to it. She laid down on the examination table, put her feet in the sturrips, and showed me her pussy. I knelt and tongued her to a rapid orgasm. She held my head as it rolled over her. Ny face was so wet when she finished, I assumed she had lost control of her bladder. But, there was no urine smell or taste, so it truly was her pussy juice. She then had me lay on the table. She strapped my legs to the sturrips, and pulled aside the panties. She then used two fingers in my ass to bring me to a glorious orgasm. When I was done, and there was no more cum to be dispensed, she put two suppositories in me, asked if I was taking the anti-biotics (I was) and told to continue them. She then told me to leave. I was wearing cum soaked panties. I asked if I could clean up, and she said no. I was to return tomorrow night at 6pm for that and I should up the outfit again with the item in the gift box she handed me as she pushed me out the door. When I got into my car, I found the gift box contained an A cup bra. I went home and cleaned myself up the best I could. I washed the cum soaked panties in preparation for the next day's adventure. The next morning, I put on the freshly washed panties and the new bra. The bra was actually a godsend, since it prevented my shirt from touching the sensitive nipples. I put on some regular clothing and went to the mall. At the mall, I bought a pack of lacey panties (for the girl friend), a nearly see-though blouse (for the girl friend), a very short skirt (for the girl friend), mascara (for the girl friend), and some calf height boots with very thick heels (I confessed to the gay shoe salesman that they were for me, and he helped me find a pair I could walk in). When I got home, I put on all my new purchases, learned to walk in the boots, and eagerly awaited my 6pm appointment with Katie. When I knocked on her door exactly at 6pm, I was looking pretty good. She opened the door and did a double-take, as I was in all new clothes. She grabbed my arm and yanked me into the house. She was on me before the door even closed. This was the first time she kissed me. She put her hands underneath my skirt, feeling my caged cock, and then broke the kiss. She told me she loved the boots, the see-through blouse, and the mascara was a great addition, too, and then dragged me to the medical room. She came quickly, but held my head there for a second, and then a third orgasm. After she caught her breath, she stripped me of my skirt and blouse and had me lay on the table. Again, she strapped my legs into the sturrips. This time she cuffed my hands to the side as well. She promised that I'd be happy she did, and reminded me how each special thing I did for her, she returned in kind for me. She undid the front clasp bra she had given me, and touched my nipples, which were swollen. She then sucked on them. The feeling for me was very different. I'd never had anyone do that before, and it gave me little jolts of pleasure. She told me my breasts were beautiful in the bra, and that she liked how more swollen they now were from her attention. She asked me if I was ready to cum, and I said I was. She put a mask over my eyes, and told me she didn't want to spoil her surprise until I was "fully committed" to it. When I asked what it was, she told me to wait and see. I felt her fingers enter my ass, and drum on my prostate. I was about to orgasm when she suddenly stopped and removed her fingers. I then felt somehing larger enter my lubed ass. She took off the blindfold and I saw her standing between my outstretched legs. She moved closer and the thing in my ass went deeper. She asked if I was ok, and I asked what was in my ass? She said her smallest, smoothest dildo attached to a harness around her waist. She moved in a little more and the dildo hit THE spot. I blasted out cum. She began to move it in and out, constantly hitting THE spot. I think I passed out from the intense pleasure. When I became aware of my surroundings again, she was holding my thighs tightly and rocking the dildo in my ass, at the same time having an obvious orgasm of her own. I laid there accepting her dildo work until she calmed down and withdrew. When it was out, my ass felt empty and I wanted it back in. I asked her to put it back in. She laughed and called me a "whore". She cleaned me up (unlocking my cum covered cock to do so), put in a few suppositories, and told me to take four anti-biotic pills a day because she apparently drew some blood. She said I'd definitely have sore thighs and my ass might be a bit sore too. She handed me her laser hair removal device and told me my chest hair needed to be gone if I wanted to continue to play at this level. She then shoved me out the door and told me to come back on Friday, clean of hair on my chest, under my arms, and especially on my face.. I used the laser device on my chest and shaved everywhere else. My thighs hurt for a day. My breasts were very tender and swollen. I figured Katie would like that. The bra now had something to hold. On Friday, I wore the same outfit, but added some costume jewelry (left at my house by Yazmin). I also had dark eye liner, to give me "bedroom eyes". Yazmin had left that at my place, too. Katie met me at the door and calmly let me into her foyer. As soon as I was in, she was behind me, her hands underneath my blouse and unbuttoning my bra. She was wearing the dildo. I felt it bump me. She caressed my swollen breats and massaged the tender nipples. Lightning bolts of pleasure went through me. She guided me to the staircase, but pushed my head down onto the first step. I put out my hands to hold myself steady. She pulled down my lacey panties. I felt her fingers and some lube. She didn't take me gently. She positioned the dildo at the opening without even entering me with her fingers first. I felt the end of the dildo and then a brief pain as the dildo's head popped inside me. She gave me a moment to catch my breath and get used to the size, then slid it deep inside. I came immediately. She began long strokes. The dildo was different than last time. It had a head on it, like a real cock. Each time the head past THE spot, cum blasted out of my cock onto the floor. I was in a state of near constant orgasm and moaned as she fucked my ass with the dildo. Her strokes got shorter, harder. She came, jamming the dildo as deep as it could go into me. I emptied all the cum I had stored onto the floor. When she removed the dildo, I asked her to put it back in. She said she would, upstairs, but first I needed to clean up my "mess". I stood up. She pointed to the puddle and drops of cum on the floor. There was a LOT of it. I took my panties in hand to clean it up, and she told me that I needed to use my tongue instead. I made a face and she said I could clean it properly, or leave now. I buttoned up my bra, put my panties on, and left. By the time I got home, I was sure I had made the correct choice. When I checked my phone a while later, I saw I had a message from Katie. The message was "Whore, come to my house Saturday at 6pm and expect to spend the rest of the weekend." I then knew I made the correct choice. I went out the next morning to buy a new outfit. I got red vinyl boots, a red vinyl mini-skirt, red silk panties, a red bra in the same A cup size, and a red bow. The bow went around my caged cock. I wore the same see through white blouse and the "fuck me red" outfit I purchased. Katie met me at the door. She made no attempt to hide the very realistic dildo strapped to her. Once the door was closed, I opened my mouth to say something, but she told me not to talk. She explained that a professional dominatrix told her that realistic dildos are the best for fucking men, so she bought three of them, in increasing sizes. By tomorrow night, I would be receiving the largest size. There would be no negociation, no complaints. I nodded in agreement. She told me I would be doing things that I never expected to do, and would do them willingly, in exchange for pleasure unlike any I had previously ever experienced. I nodded in agreement. She told me that if I said "No" even once, I would no longer be welcome and she would report to Yazmin that I had been unfaithful. I nodded in agreement. She told me to kneel before her. I did. She then brought the realistic dildo to my face and told me to suck on it like Yazmin did to my own cock. I hesitated. She hit my cheek with the dildo and reminded me that there was no saying no, or room for negociation. I put my screaming sensibilities aside and sucked the dildo like Yazmin did when I had been in the cock cage for a week. Katie had her hands on the side of my head and told me how good I was doing the whole 10 minutes before she, herself came. The dildo apparently had a set of rubber fingers on the base that tickled her clit. As I was sucking the dildo, the fingers were driving her toward an orgasm. When she came, she pushed the dildo deep into my mouth, causing me to gag as it went into my throat. She quickly withdrew it, and then mentioned that we'd work on the gag reflex and deep throat technique later. She had me go to the master bedroom. On the bed was a red teddy. I was instructed to put it on. She told me to leave on the red boots. When I had the teddy on, my swollen nipples felt the lacey material and it gave me goose bumps. Katie unbuttoned the velcro crotch and put a condom over the cock cage. She had me lay on the bed, and then brought over a vinyl covered foam wedge to put underneath my butt. It had the effect of raising my hole to a more comfortable angle for her. I pulled my legs back, allowing her direct access. She put vaseline on her fingers and lubed my hole. Then, she switched to a lube in a squirt bottle. This she also lubed me with. Finally, she wiped her fingers on her dildo and shed her robe. She was wearing a black leather bustier, which made her thin waist thinner, and accentuated the black harness with the brown realistic dildo protruding from her loins. She asked if I was ready. I said I was. She eased the dildo in gently. Cum erupted into the condom. She said she'd stop when the condom was full. And then, she was no longer gentle. She fucked me, changing angles and depths. I was cumming more or less continuously. I was moaning. I was actually trying to move to meet her thrusts to give myself more pleasure. I was living through my ass, and my orgasms were the only thing in my life. I used my hole muscles to grab at her thrusting cock after realizing that I could get even more pleasure from that than just relaxing and accepting her attack on my hole. After a while, she turned me onto my stomach, putting some pillows underneath me, and hammered me doggy style until she had her own orgasm. She buried her cock deep in my ass and drove me into the bed. She asked if I felt good. I told her I felt great! She withdrew her cock and had me get back up on my knees. She announced that my condom was full. I was to wait for her to return. She left. I watched her remove her harness and pick up another. This was topped by a dildo about the same size as my own cock. She told me that it's a special dildo and I should kneel and treat it like the special dildo it is. I knelt and sucked on it. It was a little thinner than the other dildo, and a little shorter. Still, it was fairly substantial. Katie took the condom off my cage and put another in its place. She put the used condom onto the dildo she was wearing and squeezed the balls. The cum disappeared from the condom. She removed the condom. She pointed to the dildo, which was now glistening with cum. I knew what I needed to do. I sucked on the dildo, tasting my own salty cum. After five or ten minutes, I could sense that Katie was getting close to an orgasm. When it finally hit her, she drove the dildo deep into my mouth and squeezed the balls. Cum exploded into my mouth. I coughed and gagged, but she held the dildo in my mouth until I swallowed the cum. She checked my mouth to see that I wasn't hiding it. I was told I was doing very well. My mouth had the salty sweet taste of cum in it, and it's not a taste I'd ever had before. Katie asked if I needed a break. I told her no. She said she'd be right back and I should make myself comfortable. I laid back on the bed, awaiting her return. When she came back, another woman entered with her. She was another Amazon, and had a large dildo sticking out of her black leather harness. Following her was another Amazon, with an identical dildo. The two Amazons seemed to be related, as they looked identical. Sensing my questions, Katie informed me that the two were twins, and were here to "spitroast" me. I said I didn't know what that meant. She explained that one would be in my mouth, and one in my ass. I was to pick which one went where. I pointed to one of the Amazons and said I'd take her in my mouth. The three women giggled nervously as they took up positions. Katie strapped me onto a bench face down. My ass was at the perfect height to be fucked by these large women. The one for my ass lubed me up and slid her dildo in. It was long, but not any thicker than the one Katie had used on me earlier. As such, it went in without any pain. Katie put a mask over my face, telling me I'm just a pair of holes for these two, so I don't get to see. The other dildo was presented to my mouth. I sucked on it. As the Amazon behind me began to fuck my ass, the one in front began to fuck my mouth. Katie told me that I better not bite it, to open my mouth wider, and to accept it banging against my throat. If I was about to choke, I could open my mouth and let the saliva pour out. As I gained experience with the one in my mouth, the fact that it was banging against my throat became a turn on. The Amazon in my ass really knew how to wield a dildo, and my ass was loving it. The one in my mouth started to become more erratic. She had a hold of my head and was moaning. She came. I felt warm sweet fluid run out of the end of her dildo. I sucked harder to get it all. It was very tasty. The one behind me was obviously turned on and came as well. Both Amazons held their dildos deep inside me for a minute or two, and then withdrew together. When Katie removed the blindfold, they were both gone. She asked me whether I liked it. I told her I did, especially the trick dildo of the girl at my mouth. Katie laughed when I told her I liked the taste of the girl's cum. Katie released me from the bench, and I went and cleaned myself up. On the toilet, I ejected an incredible amount of lube from my ass. Once I was clean down there, I felt my hole. It was no longer a round donut. Instead, it was elongated and puffy like a pussy. Katie put suppositories into my ass before taking me to the bed. She didn't tie me down. In the morning, I woke before she did. I slid my head between her legs and ate her to a waking orgasm. Her thighs crushed my head so hard I had to take aspirin for a headache. For breakfast, I was strapped into a chair that had a large black butt plug on the seat. The butt plug vibrated by remote control. Katie had a good time using the remote control to bring me to the edge of an orgasm, but not over, numerous times. For breakfast itself, I ate a peeled banana that Katie had in her pussy for 30 minutes. It was mushy and tasted like a pussy flavored banana. Katie told me the two Amazons would be back this afternoon. I told her I hoped my ass would still be tight enough for them. She laughed and said they're coming back for more oral sex. I said I was looking forward to more of that tasty cum I sucked out of the dildo. She smiled and said that would definitely happen. At the end of the meal, Katie asked me if I wanted to fuck someone with my cock? I said that was against Yazmin's rules. She said there was a loophole. I asked what the loophole was. She said that the rule was no intercourse with "a woman". She said she had a friend who looked like a woman, acted like a woman, and had woman parts, but was technically male. I asked how that could be and she said the friend was born a man but had gender reassignment surgery. I said I wasn't sure. She reached down to my cock cage and looked at it. There was no mistaking my animal urge to fuck a woman for the first time. She picked up her phone and asked Chris to come over. While we were waiting, Katie put fresh makeup on me, and put me into the teddy. When Chris arrived, I met her at the door. She looked me up and down, reached to feel my caged cock, and smiled. I took her offered hand and we went to the bedroom. Katie was there with the key and unlocked my cock. Chris told me what to do to get her ready, since she doesn't self lubricate. When I slid my cock into her warm velvety pussy, I could barely contain my desire to cum immediately. She moaned as I thrust into her. I didn't last very long, and apologized to her for that. Katie made me lick my cum from her pussy, even having Chris squat over my mouth so that the last few drops would fall out of her. Chris cleaned my cock with her mouth, and then put me back into the cage and locked it up tight. We laid on the bed for an hour. I played with her surgically enhanced breasts. She sucked on my swollen nipples, saying she loved "puffies". We kissed a lot. She said she was sorry we could only get together this once, because Katie obviously wasn't going to continue to share me. When she went down stairs, I was rather sad for her. Katie lifted my spirits telling me the twins were on their way. She had me change into a leather corset. She laced it up so tight I could barely breathe. She showed me the effect in the mirror. It was astounding. I now had an hourglass shape. My hips flared out, and my butt was more feminine looking. The front of the corset had breast forms built in. With their gel design, they pushed my swollen breasts up and to one side, making me look like a full B cup. But for my caged cock, I'd be a super fuckable woman. Katie put long gloves onto my arms. Then, putting my arms behind me, she began to lace them together. This quickly became painful. My laced arms pulled my shoulders back, making my breasts appear even larger. When the Amazon's arrived, I was strapped to the bench. A hood was over my head. I couldn't see except in a vertical stripe in front of me. My mouth was forced open by a metal ring behind my teeth. My arms were sticking up, and were tied to a tether on the ceiling. My legs were tied to the legs of the bench. Katie asked them if they were ready? I could see the same pink dildos as last night strapped to their loins. I saw them nod. Katie entered my ass with a larger dildo. It was a bit painful, but I moved my ass in appreciation for her dildo. I also moaned, which got her excited. She began to fuck me. The first Amazon came up and offered her dildo. I sucked on it until she established a rythym of fucking my mouth. She came, offering me the same sweet nectar as before. I sucked her dildo to get all of it. After a minute or two she stepped back, but the dildo was still in my mouth. She pulled it from my mouth and offered me a smaller dildo. It was wet with the same tasty nectar. It was warm! It had a very realistic texture. It was not hard, and was getting softer. I turned my head back and forth, spitting out the very realistic dildo. The Amazon stepped back. Her dildo looked like a real cock. The other Amazon pushed her aside and offered me her dildo, which was definitely a real cock. I knew this to be the case about 10 seconds after it got into my mouth, which was about 5 seconds before it began to spray the wonderful tasting nectar into my mouth. Despite it being a real cock, I sucked on it until the last of the cum was in my mouth. Katie was banging my ass hard, obviously turned on by my giving a blow job to the two Amazons and swallowing their cum. She came a few minutes later, and was very vocal about her orgasm. When Katie pulled out of my ass, I genuinely felt like my ass was lonely. Her big dildo had brought so much pleasure to my ass that I tried to grab it with my ass muscles as she withdrew it. The Amazons removed the eye patches that prevented me from seeing. I saw Chris come in wearing a gigantic dildo. Katie informed me that Chris volunteered to be my final lover for the day, knowing that I would likely remember the final dildo more than anything else. When Chris's dildo entered my ass, it made its own way. It pushed my interior parts around to make space for itself. Chris expertly moved it until it was hitting THE spot, and then gently rocked the big head of it over that spot. I began to spray cum into my condom. I heard myself moaning as the pleasure of that huge cock head going over THE spot brought me to orgasm after orgasm. When Chris withdrew it, my ass just wouldn't close. It was hanging open waiting for the monster to return for more fun. My day as fuck toy was almost over. But, first, Katie made me drink the cum from my condom. It was amazingly full, despite the draining I had only 12 hours earlier. Then I had to meet the Amazon twins (Adriana and Ariana), and thank them for all they did for me. Katie's way of making me thank them was to give each a blowjob. I'm not as skilled with male anatomy as female, so it took 20 minutes for each one to get their "thank you". I did swallow the sweet nectar without being asked. Then, the ultimate submission was requested. I had to perform analingus on Chris. Chris bent over and spread her ass cheeks. Her ass hole was elongated, with a crinkly opening and dark brown skin around it. It looked more like a pussy than her surgically created one. Despite everything in my head screaming "NO NO NO", I knew I had to do it. Those were the rules of the day. I cannot say no. I licked her hole, and even darted my tongue inside slightly. She moaned as I did it. Except for a slight smell, it was no worse than licking a pussy. Katie had me stop after a few minutes. Chris thanked me profusely. After everyone had left, Katie took me to the bathroom. There, she bent me over the sink and examined my ass with her fingers and a tiny fibre optic camera. She said I was in good health, with no apparent ill effects from all the fucking. She popped a few suppositories into me, saying that the inside lining of my colon was very abraded and wouldn't get enough moisture due to the fucking taking it out. The suppositories would lubricate the membranes and the medicine in them would rapidly be absorbed. She then unlocked my cock cage and had me take a shower. While in the shower alone, I played with my cock for the first time in weeks. Not surprisingly, I couldn't get an erection. Not even a tiny stiffening. When I came out of the shower, Katie was there with a towel to dry me off. She tried to stimulate my cock, but no erection came. She said nothing about it. Instead, she talked about a change in schedule. On Friday, I was to arrive in a conservative outfit that any woman would wear. I was to wear appropriate make up. I should make sure I was completely clean shaven. Then, she did my make up, and gathered up my clothes so I could put them on. She didn't lock my cock up. When I was about to leave, she handed me the cock cage and the opened lock, instructing me to put it on if I had an erection. During the week, I went to the mall and bought a conservative skirt, blouse, and a flesh colored bra (all "for the girlfriend"). Each night, I tugged on my cock, but couldn't make it get to do anything until Thursday. On Thursday night, I got a little stiffening. I put the cage on and locked it, even though I wasn't able to achieve a full erection. On Friday, I arrived in the conservative plaid knee length skirt, the beige blouse, my new flesh colored bra, black lacey panties, and the brown boots. I carried the small purse she gave me. In it was my make up, car keys, and the contents of my wallet. My legs were shaved smooth, as was my face. Katie let me in and looked me over. She pronounced me "excellent". She told me that her period began today, so today's get together wouldn't include me giving her an oral orgasm. She asked about the cage, and I told her what happened. She nodded in understanding. She took me to a salon. There, the gay male stylist looked over my shoulder length hair, told me I was using the wrong shampoo and styling products, and then washed, cut, and re-styled my hair. I have to say, when he was done, I had a very fashionable female head of hair. When I asked how much, the stylist smiled and pointed to a back room. I looked at Katie. She nodded. The stylist and I went to the back room, where he asked if I was a top or bottom. I just looked at him. He said that I was a top if I liked putting it in, and a bottom if I liked getting it. I told him I was a bottom. He suggested a blowjob. I knelt on the ground. He didn't unbutton his pants, so I did it. When I pulled out his cock, it was already hard. It was an attractive cock. I kissed it, then licked it, then started sucking on it. He held my head as I used my mouth like a pussy. After a few minutes, he said he was about to cum. I doubled down on my efforts, and swallowed his cum. Not until I opened my mouth did I actually taste anything, because his cock was so deep in my mouth. The taste was very sweet. I told him his cum was very sweet. He said he was a diabetic, and excretes lots of sugar. He complimented me on both my style and my willingness to swallow. He told me to come back any time I wanted for a hair appointment, with a back room payment afterwards. I told him I would, that I loved the new hair style, and especially enjoyed his cum. He had me wipe off my smeared lipstick before I returned to the salon proper. In the salon, Katie handed me my purse, and suggested I re-apply my lipstick. I went to the only bathroom in the place and put on fresh makeup. When I came out, Katie gave me a thumbs up. I thanked the stylist again, and we left. Katie drove us to the mall. I hadn't really gone out in public, yet she wanted to go shopping. She took me to Victoria's Secret to buy a new bra. She selected a "gel" bra with a name that promised huge cleavage. We went to the dressing room and I tried it on. It gave me actual cleavage by pushing what little I had towards the center. Katie felt it looked too fake. She left and returned with two others. The first had a lot of padding, and was rather comfortable. It was labelled a +2. The second was a gel bra with additional padding that was removable "to equalize". I put this on and knew I found the right bra. I looked like a woman, right down to the skin showing at the top of the bra. I put my own bra back on, and then my blouse. Katie selected the same style of bra in black, white, and flesh, then added some lacey panties and a black teddy to the pile. I paid cash and followed Katie to the next store. The next store was a department store. She took me to the cosmetics counter and got a "consultant" to look at me. The consultant suggested some changes to colors, a skin regime to minimize pores, and Katie agreed. So, I let the consultant do my make-up. I had no idea that I could look so nice. I bought all of it, again with cash. Katie took me to the department store shoe department. My favorite sales person was there. He didn't recognize me. Katie selected a number of styles of shoes, all with heels. I questioned her whether I could wear them. She assured me I'd get the hang of it quickly. The salesman recognized my feet and winked at me. I smiled back. In the end, I selected two pairs of shoes. I paid with my credit card, since the salesman knew me. We had dinner at Friday's in the mall. The young man serving us called me "ma'am" the entire dinner. Katie paid for dinner and drove us back to her place. She bid me good night at the curb. I asked if I might come in, and she said no. She made me wait, however, until she went into the house and came back. She handed me the first (smallest) realistic dildo she used on me, an unlabelled bottle of cream, and a large unlabelled bottle that Katie said contained the suppositories she had previously used on me. My homework assignment was to use the dildo, lubricated with the cream, for 15 minutes a day, followed up with 2 suppositories when I was about to go to bed. I thanked her and drove home.Once inside my apartment, I couldn't wait to use the dildo. I actually did my 15 minute "homework" not five feet from my front door, still wearing my panties and skirt. When I was done, my panties were drenched. I put in 2 suppositories, cleaned up, changed my panties, and put on my new teddy. Exhausted, I went to bed. I woke up the next morning incredibly horny. My cock, of course, was still caged, and it wasn't stirring. I needed my ass fucked. It was a new day, so I put a condom over the cock cage, lubed up the dildo with the special cream from Katie, and fucked my ass with the dildo until I was dry cumming. The condom was filled with cum, which I drank. I had violated Katie's rule. I had fucked myself for an hour. I put in a pair of suppositories, just in case, and then called atie. I explained what I had done. She told me to bring her back the dildo. I dressed in the same outfit as yesterday, but with my new bra and panties from Victoria's Secret, and went to return the dildo to Katie. She was a little disappointed that I couldn't self police my play with the dildo. But, she was more upset that I was wearing the same clothes. She took me to the mall again. There, we spent hours picking out new outfits for me. All were very conservative. I got enough clothes to last a week without washing them. I paid for everything with my credit card. Katie accompanied me to my apartment with the purchases. She confiscated all of my male underwear, shoes, shirts, and grooming products. She told me she'd periodically be watching, and that every time I went out the door I was to be dressed as a woman. I told her I would. She handed me a bag containing 2 dildos. One was the one I returned that morning. The other was the trick dildo that squirts cum when you squeeze the balls. She told me to use them in moderation, and always with the special lube she provided. She offered to unlock my cock, but I declined. I needed to have an incentive to not abandon all that I had achieved. I promised I'd be good about not over- using the dildos. She left, saying that she would see me at the normal time on Friday. During the week, I followed the skin care regime. I noticed my skin getting softer. I practiced putting on the make up until I was able to duplicate the make up consultant's work. When I left the house, which wasn't often, I wore women's clothing. I shopped at the store in women's clothing. People addressed me in the female pronoun. At home, I used the dildos every morning and night. I watched Internet porn on how to deep throat, and practiced with the shooting dildo. I spotted Katie outside my house once, so she was definitely watching me. On Friday, Katie met me at the door. She was wearing her black leather bustier, but no dildo harness. She backed me against a wall and kissed me for several minutes, then led me upstairs. In her bedroom, I was tied to the bed fully clothed and she rode my face until she came. Then, she unlocked my cock cage, cleaned my cock, and put the cage back on. She then hustled me out of there without an explanation as to why I was getting such a treatment. I went home, contemplating what I might have done wrong. I didn't see it. I called her to ask. She said that she felt I needed more practice as a woman with a woman. She reminded me that tomorrow was Halloween, and we still had plans to go to a party. She would pick up me at 7pm and drive us to the party. I had picked out my costume earlier in the week. It was Japanese cosplay character. Female. It came with a mask that was very cartoon like with big eyes and huge lips. The rest of the outfit was a bra (hugely padded with flesh colored inserts), garter belt with nylons, high heels (which I had, by now, mastered), and a bright blue pair of panties with a molded in outline of a 10" long penis. I had tried it on and I thought I looked hot in it. When Katie picked me up the next day, I skipped out of the house in the outfit. She laughed, and thought it was fun. As we were driving to the party, she asked me what possessed me to dress as a futanari? I told her I thought it was a way for me to show off my body. Plus, I liked the cartoonish big boobs and the way the padded bra felt on my chest. She told me the outfit would get me a lot of attention at the party. She was wearing all black pvc, which showed every muscle and fold in her very toned body. Her clit was especially prominent in the outfit, a bulge not unlike a small penis. We arrived at the party. It was held at a huge estate. A parking attendent took Katie's car away. Katie put on the matching mask to the pvc outfit. I could see why she didn't wear it earlier. There was a gag in it, with a pumping ball hanging out of the front, tubes from her nose that extended out in front of her, and bright red horns on the top of it. It was, in a word, scary. We entered the party. The costumes were all very "edgy". Many were right out of a dominatrix's closet. Others, like mine, showed a lot of skin. I was a bit shocked when one of the guests, dressed as a satyr, walked up to Katie and began to stroke her clit through the pvc. Katie stood there and accepted it. Through her gagged mouth, I heard her moaning. It was apparent when she came, as she bent at the waist and made a wailing sound around the mask. After he left, I brought Katie to a seat so she could recover from the orgasm. As we were sitting there, another woman dressed in pvc came by and pumped up Katie's gag. When she sat down next to Katie, I informed her that Katie just orgasmed less than 10 minutes ago. The PVC clad woman stood up, dropped a panel from her pants, and mounted Katie's face. I rose to stop it, but Katie was holding the woman in place. Her breathing tubes were inserted into the woman's pussy and I could hear a rude bubbling sound as Katie vacuumed cum from her pussy with her breathing tubes. The woman dismounted after only 10 or 15 seconds, leaving Katie's pvc slimy with her juices. A futanari came up to me and asked if I wanted to go upstairs. Katie waved me to go. Upstairs, the futa exposed herself to me. She had 10 real inches of man meat between her legs. I had never seen a cock so big, but had sucked dildos as large and was not scared. I gave the futa an outstanding blow job, but she withdrew and blew her cum all over my mask instead of in my greedy mouth. When she was done shooting, I took the big cock in my mouth, cleaned it, and vacuumed all the remaining cum out. After I pulled back, the futa covered herself up and left. I returned to the party, with cum dripping from my mask. Katie gave me a thumbs up when she saw me, since she was unable to speak. Once the cum was on my mask, I got numerous requests to go upstairs. I took them in groups of two. Word got around and I found myself with a line in front of me. I did my best with every one. Despite not having any of the appetizers, my belly was full by the end of the night. When we got out to the car, Katie told me that she was touched, stroked, and fondled the entire night. She had so many orgasms she lost track. She asked how many cocks I sucked, and I said 42, which is where I stopped counting. We both laughed, considering this a very enjoyable evening. She dropped me off at my house, suggesting I take extra anti-biotics due to all the cum inside me, and an extra dose of the suppositories, just in case. I followed her direction after a very satisfying 30 minutes with the dildo. The following Friday, I arrived at Katie's house as usual. She told me that she had a new strap on she wanted to try. Of course, I showed great enthusiasm. The dildo was molded to exactly fit her big clit, and was held in place by a section that went into her pussy. No straps at all. She had me suck on it as foreplay. Just sucking on it was enough to make Katie cum. When she mounted my ass with it, she often had to stop, since the sensations were overwhelming. I was excited to see her so excited to fuck me, and had numerous orgasms myself. Katie allowed me out of the cock cage, after trying to get an erection without success while cleaning me. She handed it to me to take home. A number of suppositories and more anti- biotics came home for me to use during the week. I'd been noticing my ass getting bigger. It was apparent when I wore the "misses" jeans Katie made me buy. My breasts were also growing. I became suspicious of the suppositories being something else. I took them, the lubricating cream, and the anti-biotic pills to the pharmacy. The pharmacist said the pills were hormone replacement therapy estrogen pills. He couldn't identify the cream, but thought it might be the same thing based upon the shape of the tube. The suppositories he said looked like standard suppositories for hard stools. I continued to use the suppositories, but switched to a regular lube for anal play. I discontinued the use of the "anti-biotics". I was going to confront Katie about the deception, but figured I'd go along for a bit longer. Friday came and Katie was having her period. I was very horny, however, and asked her to fuck me. She told me no, that we had an appointment at the plastic surgeon's office. He previously removed my adams apple. When we went in, the receptionist handed us a large color book. Inside were seemingly every shape and size of breasts. I told Katie I wasn't able to afford a boob job. She said the owner of the estate where we attended the party was going to pay for it. I told her I wasn't sure I wanted permanent boobs. She and I got into it, and stepped into the hallway. She reached out and touched my breasts, which were still swollen and tender. She said that their growth meant that I should be a girl. I blurted out that feeding me HRT pills for weeks would also do that. She apologized for that, and tried to convince me to go back in. I finally did, but just to humor her. The doctor was very nice. He looked at my chest, did some measurements, and was able to show us on the computer exactly which breasts would look best on me. I said I wasn't sure I wanted to go through with it, but he said just pick which ones I liked. I chose a perky and full B cup, which he said was his preferred size for me. He had me sign some paperwork, and told me the scheduling nurse would call me. We left, and I told Katie I didn't want permanent boobs. She said to schedule the procedure after Thanksgiving, which would give me time to "think about it some more". So, when the scheduling nurse called on Monday, I scheduled the appointment for the week after Thanksgiving. The Friday after Thanksgiving, I arrived at Katies. My cock had not had an erection in a week, and I carried the cage in my purse. I was met at the door by Yazmin. I opened my mouth to speak, but said nothing. Tears started to come down my eyes. She took my arm and brought me into the house. She said it was ok. She brought me to the family room. Katie was there. On the big screen TV was a video of me at the party. Yazmin sat me down and I watched myself suck cock. Yazmin commented on my skills, saying that I was truly gifted. Katie had her hand in her crotch and was masturbating to it. For ten minutes, we sat in silence, until Katie came. Yazmin said she couldn't take any more, stood up and pulled off her pants. She seated herself over Katie's face and rode it as she watched me sucking cocks. Eventually, I ran out of cocks at the party, and the video became a montage of me being fucked in the ass. From all kinds of angles, over numerous days, I was a hole to be enjoyed by real cock and dildo alike. I put my hand in my shirt and gently stroked my breast and nipple. Yazmin came, loudly. After a moment, she dismounted Katie's face. Katie remarked at how well I took cock. Yazmin agreed, and then put her hand in my blouse to stroke the other nipple. Yazmin commented how nice my breasts were, and demanded I remove my blouse and bra. I did so, and she started to lick my nipples. I arched my back in pleasure. Yazmin stopped and asked when my new boobs were going to be installed. Katie said "next week" and Yazmin said she was pleased with the design chosen. Yazmin led me upstairs to the bedroom. She stripped me of my panties, noted the flaccid nature of my cock and the absence of the cock cage, and then put me into the suspended harness. She chose a large realistic dildo, lubed it well, and fucked my brains out for an hour. Afterwards, she released me and I was given a mask that included a large thick dildo sticking out of the front. It was held in place by a smaller dildo that went into my mouth. Yazmin strapped me to the bed and rode that dildo until she came twice. I watched her from below as she rode up and down. Her juices dripped out onto the mask and into my nose. When she was done, she dismounted, but left the mask on me. Katie took her place for a very quick orgasm. The girls didn't release me, but did remove the mask. In its place, they put a larger inflatable gag. They then teased my nipples, which had me completely aroused, before they decided to play with each other. I watched Katie fuck Yazmin's pussy, the pussy I wasn't allowed to fuck, with a thick black dildo. She then moved it to Yazmin's ass. Yazmin was moaning and slamming herself against the dildo. When Yazmin had an orgasm from the ass fucking, I knew that she had been playing me for quite some time. Being gagged, I could say nothing. After some time, Katie removed the dildo from Yazmin's ass. They each laid on a side of me. Yazmin asked me how I liked watching her fucked in places I would never get to fuck? Katie laughed. I said nothing. I was still gagged. I laid there until I fell asleep. The next morning I awoke to an empty bed. Thankfully, they had uncuffed me and deflated the gag. I removed the gag and sat up. Neither Katie nor Yazmin was in the room. I got up and put on my lacey panties and my bra, which I found neatly folded on a chair. I made my way downstairs. I found them in the kitchen. I confronted Yazmin about how long this has been going on? She replied that she always knew she was gay, but stayed in the closet because of her family. She started seeing Katie a few weeks before Prom, and Katie, not realizing the importance of Yazmin's hymen, broke it. She said she loved me, but couldn't be with me because she was attracted to girls. The cock cage was really about keeping me distracted, as Yazmin was being fucked every day by Katie. Rather than dump me when she went to college, Katie suggested she try to convert me into a female. All of the cremes, ointments, pills, and lubricants were laced with highly concentrated estrogen, as I suspected. The innocuous suppositories were an anti-male hormone therapy given to sex offenders. Basically, I was being chemically castrated and I didn't know it. Even when I realized the drugs weren't as advertised, it was too late for the chemical castration to be un-done. I was now, and forever would be, unable to get an erection. I began to cry. Yazmin kissed me on the cheek and sat me down. She was smiling. She said I'd make the perfect wife for her! I looked at her and she was serious. She went on to explain that she told her parents that I had come to realize that I was really a woman after I was unable to masturbate due to the cock cage. She showed them videos of me in women's clothing, and a short piece of me sucking cock at the party. She told them she knew long ago, and being a lesbian (another shock to Mom and Dad), she figured I'd be the perfect boy friend for her. She admitted that I spent considerable time pleasuring her orally when we were dating, but never went beyond that. Finally, she told her parents that we were both in love with one another, and that, as is our ethnic custom, I would be becomng a woman by the end of the year. She got them to give her the money to pay for the boob job. It wasn't the estate owner at all. Yazmin looked deeply in to my teary eyes and told me she loved me. Once I had real breasts, I could meet her parents again without any stigma. I was overcome. The only thing I could say was "I like cum". She replied she did, too, and we could invite men over occasionally to play with us. I nodded. She took me upstairs, strapped a dildo on me, and had me fuck her. It was a rewarding experience to finally fuck Yazmin's pussy and ass, after being denied for so long. And, without the issue of me getting too excited and cumming, I fucked her for a good long time. She left the bed bow-legged. That was the last time I played a male role. Since then, I've been fucked by Yazmin's dildo and a few selected men. When we go out together, men are always coming over to talk to us and pick us up. My breasts are beautiful and perfect, and I only wear low cut blouses to show them off. My ass, through hormone therapy, is a perfect heart shape. My cock is getting smaller due to the heavy hormones, but I only use it to pee and to dribble out cum when I'm fucked so that's ok with me. So, my advice is to wear the cock cage for your girlfriend. Maybe, just maybe, you'll find she'll help you bring out your innermost desires.