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Road to RuinJamie’s Road to Ruin PartI am about to tell a story that is true. It was my first experience butit shaped my life forever, not necessarily for the better. As a c***d,I used to fantasize about being a woman, but never acted on it.Anything “gay” freaked me out. In any event, I was very closeted andrepressed. And very awkward around women I was attracted to, but seemedto be able to make a lot of female “friends.”Years ago when I was in my twenties, a female friend of mine, Karen,tripped and fell and cut her chin open. One of her girlfriends, Kathy,loaned me her car to give Karen a ride to the hospital. After taking myfriend Karen to the hospital and getting her stitched up I drove herhome and then drove the car to a bar that had bands that play jazz whereKathy was, so I can return the car. I had expected Kathy to have thecourtesy to drive me home but she didn’t want to do that so I was kindof stuck.I decided to hitchhike home. After a brief period of time, a fairlyconservative looking guy picked me up and asked me where I was going. Igave him directions and off we started. I suppose I should describemyself. In those days I have very long hair which reached down to themiddle of my back. I was tall and very slender. Jerks used to shout atme from their car windows “are you a boy or a girl?’ In any event, myrescuer was a fairly large and burly looking guy, but seemed friendlyand we had a pleasant time talking. In those days, I lived in a collegetown and hitchhiking was a viable means of transportation and a good wayto meet interesting people. He asked me if I needed to get home rightaway and I told him not necessarily. We stopped at another bar he wasfamiliar with and listened to a live band this guy knew about. It was acountry and western band, which wasn’t really my thing, but they soundedpretty good. It didn’t seem like a shitkicker bar so after my initialanxiety, I was reasonably comfortable. I remember my benefactor keptsaying of the guitar player “he plays a mean guitar doesn’t he?” Hesaid that many times and I think he was pretty drunk by then. We gotback into his car and he then asked if I wanted to stop at his house formore drinks (he said it was close by and that he would drive me homeafter that). I was pretty blasted at that point, having been drinkingall night. I said ok, and we talked some more, then, after a few minutesas we were driving, he asked me if I had ever sucked a cock. Out of theblue, as we had not talked about anything sexual all night. I was verynervous, and felt butterflies in my stomach like never before, but atthe same time, I became pretty excited (and as I said, I was reallydrunk). It had been something but I had fantasized about for a long time butnever had acted on. I have always had fantasies of being a woman, or atleast playing that role with a man. When I looked at porn, it wasalways straight porn, but I loved watching cocks and cumshots more thananything. In any event, I said no I had never sucked a cock. He lookeddisappointed, but then I told him that I had fantasized about it forsome time. I then asked him why he asked me that question. He reachedover and took my hand and put it on his crotch. I could feel him gettinghard and I remember thinking that he was pretty big too. I was filledwith anxiety but I got hard too. I was way too anxious to say anything.With his hand over mine and, therefore, making me do it, I fondled hiscock on the way to his house, but only through his pants.When we got to his house and went inside, he told me to strip. Hisattitude changed quite a bit all of a sudden. He wasn’t exactly meanbut suddenly he seemed very demanding. He told me he was divorced, buthad some of his wife’s stuff still. I had long hair back in those days.He left for a minute, came back with a skirt and some lipstick. Heagain told me to strip and I was worried for a while that somethingreally bad was going to happen to me. However, I have always been alittle submissive and I felt like I should obey. I said “Yes Sir” and Ipeeled off my clothes and was standing there in front of him naked withmy dick as hard as it has ever been in my life. He told me to put onthe skirt and then he applied the lipstick to me. My heart waspounding.At that point he kissed me and stuck his tongue in my mouth. He put hishands on my shoulders and pushed me down to my knees and told me to suckhis cock. I unzipped his pants, he was partially hard and in order toplease him I licked the shaft of his cock and his balls and thenproceeded to start to suck his cock while my hand cradled his balls.While I was doing that, he started calling me names, telling me that Iwas a whore and a cocksucker. I pulled back a bit, startled that hewas treating me like this, but at the same time was incredibly turnedon. He told me to keep sucking and pushed my head on his shaft. Istarted gagging a bit and that seemed to turn him on more. He reallywas pretty big and my jaw was getting very tired and I wasn’t sure howmuch longer I could keep it up, but when I squeezed his balls a bit, hecame in my mouth and all over my face. I was freaked out and spit outthe cum, which dribbled down my chin, but he wouldn’t let me get up fora while and there I was, on my knees with cum dripping down my chin andlipstick smeared on my face. He did not do anything to get me off and I asked if he minded if Ijerked off. He told me I could if I ate my own cum, but then didn’tmake me do it when I came. I never came so hard in my life and it onlytook a few seconds as I was so turned on.He told me to clean myself off in the bathroom. I went and wipedeverything off of me and came back to the living room topless and stillwearing the skirt. He pulled out the lipstick again and painted my lipsfor the second time. He started kissing me again, really hard and thenmade me lie down on the floor. He got some Vaseline (which is not avery good lubricant as I was about to find our the hard way) and smeareda handful on my ass. He then mounted me missionary style and I wrappedmy legs around him as he entered me. You read all of these stories thatsay that anal sex hurts at first and then the fuckee loosens up and itfeels ever so good? I am sorry to say that it hurt a lot at first andjust got worse. I had a drunken guy fucking the hell out of me and hewould not stop until he came. I think that it took a very long timeboth because he was drunk and it was his second shot of the evening. Iwasn’t sure what to do, and I was in pain, so I reached around and putmy finger in his ass and at the same time, started sucking on hisnipples. That seemed to do the trick as he started grunting and I couldfeel him shaking all over as he bred me.After that, we both kind of passed out. I woke up a few hours later. Hewas still lights out. I had sobered up a bit and the reality of what Iwas doing hit me and I was in a panic. I tip toed to the bathroom,wiped off the rest of the lipstick, put on my clothes and left. As Isobered up, I was pretty freaked out. It had been my first experiencewith a man and as a k** growing up, the worst insult anybody could throwat you was fag. And here I was, completely emasculated, but reallyturned on by it. I was not sure of what that meant, or the consequencesof my actions.I had blood in the toilet the next day when I went to the bathroom, butI was scared to go to the hospital. It took about four days for my buttto stop hurting. I masturbated a couple of times every night relivingthe memory of that evening. I did not know my new friend’s phone numberand wasn’t sure if I wanted to, or should, ever try to contact himagain. I was not sure what my reception would be. At the same time, Iwas fascinated with the role I had played.I went back and forth about the experience, but what it did for me wasto start me on the road to my slow transformation. I shaved all my bodyhair off, including my armpits and legs. I mail ordered some pantiesand got some nail polish from the store and started wearing pantiesunder my regular clothing and also started painting my toenails. Itturned me on to think about having that secret as I went about myregular business. I also bought a bra and some breast forms and wouldput them on when I was alone. But I was scared to venture out withthose on.Since the time of my first experience, I spent a bit of time troubled bywhat happened. On the one hand, it turned me on like I had neverexpected. On the other hand, I was experiencing a lot of conflict withmy sexuality. I will say in those days, that I would have more than abit of anxiety thinking that I was gay. I was more than a bit ignorantof the transgender scene, which was non-existent in my home town as faras I knew, and the internet was not as sophisticated as it is now. Itmay sound odd, or contradictory, but I guess I convinced myself that ifI was a woman, it would not be so wrong, but I was a man. In any event,I was pretty sure that I had taken my walk on the wild side and spentsome time overcompensating for it. A nice fantasy to use, but notsomething I would repeat. I would walk down the street desperatelytrying to make sure that I was attracted to every woman that went by.Unfortunately, my period of real chastity didn’t last all that long.After a few weeks of trying to be very macho, I reverted back to beingmore feminine, at least in private. In short order, I became addictedto my closet dressing and wore panties underneath my regular clothesalmost every day. I also painted my toenails and went about my businesswith my covered up toes screaming alternative lifestyle. In additionto the feminine clothes that I had purchased, I went to the local”marital aids” shop and purchased a number of toys. I bought a buttplug and a couple of dildos. My fantasy life for masturbating mainlyconsisted of me dressing up fully, putting on makeup and getting one ofmy dildos and putting it in my mouth and pretending that I was suckingcock, while at the same time, stretching my ass with a fairly good sixedbutt plug. I really liked wearing bright red lipstick for some reason. I would also practice sucking cock on the dildo and got my jaw musclesin better shape than they were before.I fantasized about men cumming in my mouth. I liked to watch bukakkevideos. I would tell myself that I would swallow my own cum to practicedoing it for the next man I might pleasure. Of course, as soon as I hadan orgasm, I would be disgusted with myself and take off my clothes,wipe the cum off my hand and not swallow anything. Fantasy and realitydo not always mix. I did have a few times where I would lay on my backand bring my legs over my head so that my cock was in front of my face. If I really forced it, I could just get the head of my cock in my mouth.I started getting some neck pain from that and stopped that practicepretty quick.In any event, as was my practice, I had driven to school for class andwas driving home to the West side of town. From the outside, I lookedlike a typical college student with boots, bluejeans and a flannelshirt. However underneath I had painted my toenails red, had red thighhighs on and red panties on underneath everything. I picked up a hitch-hiker who was going about half way down Main Street. He said his namewas Frank. Frank was a tall very built, black man in his early 20’s.We started talking about music and found we had a lot in common. Weboth liked the same kind of music and he said that he invited me back tohis place. He seemed like a nice guy and I had nothing to do, so Iagreed to take him home.It was snowy out, so I took my boots off when we got to his place. Wespent istanbul escort bayan what seemed like a few hours talking and we were drinking a fairamount and I was pretty buzzed. He was playing a bunch of records byartists that I was not familiar with and I think he enjoyed turning meon to new music. At some point, his phone rang and he picked it up.The conversation sounded like he was talking to a friend. All of asudden, he had a odd, kind of puzzled look on his face and it lookedlike he was staring at my feet. I looked down and to my dismay, sawthat there was a hole at my big toe in my right sock. My bright redtoenail and the red stockings were poking out, and apparently, givingaway my secret. I could tell from the conversation that his friendwanted to come over right away, but Frank was telling him to come by ina few hours. I could make out what sounded like the question beingasked on the other side of the line: “What, do you have a girl over?”and definitely heard Frank say “you might say something like that.”Frank hung up and gave me a funny look. I kind of raised my arms andshrugged. Frank said “is there something you want to tell me?” He tooka step towards me, but still was about 3 feet away from the couch I wassitting on. I wasn’t sure what to say, and maybe Frank wasn’t either,but I said “I have a bit of a secret – here let me show you. ” I stoodup and pulled off my jeans, which exposed my thigh highs, panties andtoenails. He kind of stared at me for short while, and I wasn’t surehow he would react, but in a few seconds, it was clear what he was goingto do. He simply unbuckled his belt and zipped his fly down and lethis pants drop to his ankles and then looked at me with an Ok, what areyou going to do now look? I could have said something, or jumped up andleft, but instead, l found myself looking at the most perfect cock I hadever seen in my life. I was immobilized for a few seconds. Flaccid, hisdick was bigger than mine when it was fully erect. In any event, Ifound myself kneeling in front of him with my mouth open. I put my lipson the head of his cock and started sucking, feeling him getting biggerand bigger. Frank’s cock was a “shower” because while it did get biggerwhen he was erect, it didn’t increase in size proportionately the waymine does. That was a good thing, otherwise, I could not have taken itin my mouth. In any event, Frank had to be a good 8 or 9 inches whenhard. I licked his shaft and sucked on his balls for a while and thengot to work on the head of his shaft. I had one hand on his balls andanother on his shaft and was sucking on the head of his cock for all Iwas worth. I could feel him start to shake and in a few seconds afterthat, felt his cum hitting my mouth. I swallowed and swallowed until hewas done and then sat back up on the couch. The whole event couldn’thave taken more than 5 minutes. I wasn’t sure what was going to happennext. Frank told me that I was the first man he had been with and Itold him he was the second. He said that his friends were coming oversoon and I should leave, but he said I should call him later in theweek. He gave me his phone number and I left his apartment with thetaste of cum in my mouth and thought to myself that I was pretty sure Iwas about to begin another bout of anxiety and self doubt. And indeed Idid. While I went home and masturbated to the memory of what I had justdone, I am sad to say that I never called Frank and never got togetherwith him again. Looking back on it I got the sense that might’ve beenthe most normal relationship I might’ve had in all this. But at thesame time, what was a pleasant afternoon ended with a blow and go (andwith no though of my pleasure at the time). In any event, this secondstep pretty much made it impossible to pretend that my feminization wassomething I could stop at any time. Also, it worried me that myimmediate reaction to seeing another man’s cock was to drop to my kneesand start sucking. And why was I only concerned about pleasing him andnot myself at the time? As future episodes will reveal, that reactionwould dictate the path my life was about to take.After a few weeks had passed since my encounter with Frank, I felt likemaybe I should try to make contact with the man that had started my pathto ruin. Since it was still winter, I could do a lot of things withoutpeople noticing. I continued to shave my legs, chest and underarms andpaint my toenails. In preparation to meet John (I really wanted to makea good impression) I got a pair of red panties and red thigh highstockings and put those on. I put on a bra with my breast forms andtopped it off with a red form fitting dress. I put jeans on over thisand put on my down coat and boots. The coat covered the breast formsnicely and I looked pretty normal and nobody would know I was femmed upunderneath. I also got some KY jelly as I had learned my lesson aboutVaseline.It was a Saturday night and I went to John’s house. The lights were onand my heart was pounding as I rang the door bell. He answered the doorand looked very surprised to see me. I said hello and told him that ifthis was a bad time or if he didn’t ever want to see me again I would notbother him. He had a funny look on his face and then smiled and told meto come in. When I stepped into the hallway, I heard him close and lockthe door behind me and then I heard voices in another room. He took myhand and pulled me into his living room. There, to my shock and horror,were two other men. They were both drinking beer and there was a pornvideo playing on the television. One of the men was in a chair, with hispants around his ankles jerking off.”This is the sissy I was telling you about” he said. It turned out thatsince my encounter with John, he had discovered social media and wasgetting his needs fulfilled by putting ads in for guys to get togetherand jerk off to porn. I had stepped into one of those times. In anyevent, he then turned to me and told me to take off my jacket. Seeing mydress, panties and the stockings, all three men started laughing andcalling me names and asked me what I was going to do for them. John wentto the bathroom and got out the lipstick. On it went and next thing Iknew, I was on my knees with three men in front of me. I had a cock inmy mouth and one in each hand, while on the television a naked femaleslut was doing the same thing, only with five men.The first man came in my mouth pretty quickly and all three of the mentold me to swallow his come like a whore would. (I am not sure that realwhores do that, but swallow I did). It tasted bad. So many times thefantasy never lives up to the reality. The first comer (I never did gethis name) then went to the kitchen to get beers for the others and Imoved on to sucking the other stranger’s cock. My jaw started to gettired again and I was not sure how long I could keep sucking. John waslooking at me and I tried squeezing the stranger’s balls to see if thatwould hurry things up. Fortunately it did, and I was swallowing mysecond load of the evening.The two strangers sat down on the couch to watch me suck off John’s cock.His was the biggest one, and I was trembling to keep my jaw from lockingup. Oddly, a minute after I started, he turned his back to me. I wasafraid I had displeased him, but at the same time, needed a moment torest my jaw. My relief turned to grief when he told me to lick hisasshole. I had never done that before and was grossed out. He said itagain and told me he did not want to have to tell me a third time. I gotnervous and did what I was told. I could smell excrement and wasgagging, but stuck my tongue in his butt hole like he demanded. He toldthe others “looks like this sissy is will do anything I tell her to.” Iguess I would, or so it appeared at the moment. My fault for going backI guess. After I had licked his ass clean, he told me to stand up andstay in place. He went to another room and came back with an old lookingdog collar and a leash. I was collared and he pulled the leash and mademe follow him to the bedroom. I was made to take off my dress andpanties. He lay down on the bed on his back and told me to get on allfours and suck him off. A minute later, his friends came into thebedroom and one of them started playing with my ass. I felt some lube goon and then I felt a cock pushing to get into me. Pretty soon, I wasbeing spit roasted. I found it hard to concentrate on sucking cock withanother one slamming into me, but fortunately, the stranger came quickly.Then it was the other’s turn. He too was relatively quick, something forwhich I was grateful, as I was still not used to anal sex. My jaw wasgiving out when John moved around, pushed my face into the pillow andrammed his big cock into my butt. He pumped for all he was worth. Iwas glad the other two smaller men had opened me up, because I think Iwould have really had a bad time otherwise. He came and then it seemedlike the guys were done with me. “Get dressed slut” I was told. As soonas I was dressed, John told me it was time to leave. As he closed thedoor, he told me that I should return in two weeks and that I would havea night I would never forget.I had already had a night I would never forget. I never returned as Iwas afraid of what lay in store for me. I think that, originally, Ithought that by going back, I might be able to develop a regular kind ofrelationship with John and perhaps have regular outlet for my submissiveurges, but I wasn’t ready to be passed around like some prison bitch. Iwas also a bit disturbed and scared by my acquiescence at being orderedto do kinky things. Of course, like so many New Year’s resolutions, itseemed like I was destined to forget this lesson all too soon.This chapter is a bit creepy, but it is part of my story. I had a veryweird relationship with my mother. She was an alcoholic and veryflighty. In many ways, I feel that she unmanned me growing up. In anyevent, I had not seen her for a while, and she called me up and told methat she wanted to come by and take me to the movies. When she got tomy apartment she then said that she had been dating some guy for a whileand wanted him to come along as well and asked if I would mind. I saidno, I wouldn’t mind (like I had a choice).On the way over to the fellow’s place, (his name was Bob) mom wascomplaining that she wondered if the guy was gay. She said usually whenshe went out with a man, he would be all over her but this guy had nevermade a move on her or had even tried to kiss her. (Mom had a habit ofsharing her sex life with me-never mind that I had told her that suchtalk makes me very uncomfortable). She said Bob was a photographer andindeed when we go to his house he did have a very elaborate photo studioin one of his rooms with a backdrop and lights.We made some small talk and then went to the movies. Mom and Bob talkedthrough the entire film, with people in the seats around us telling themto be quiet. Mom always did things that embarrassed me and never seemedto care. After the movie, we went back to Bob’s house to have somedrinks. Bob made us all martinis and the conversation livened up quitea bit. It was the first time I had ever had a martini (or three) and Iwas pretty buzzed.We spent a little time talking and Bob seem to be a bit taken with me,or so I thought. He spent most of the time talking to me and ignoringmy mother. He asked a lot of questions about my long hair and asked ifmen confused me for a girl. My mom did not like that line ofquestioning and it made me a little uncomfortable too, since she wasthere. I am not sure how I would have felt about it if she wasn’t withme.At one point, as Bob was showing us around the house, we were standingin Bob’s living room. My mom asked to use the bathroom, which was downa long hall. As she was walking down the hall, Bob stood to my side andsort of caressed my ass with the palm of his hand and told me that I waswelcome to come by anytime. Oddly, I did not pull away at this touch.I started getting hard and took my hand to adjust my cock to be morecomfortable in my jeans. Bob noticed immediately and ran his hand upunderneath my ass and cupped my balls. I heard the toilet flush andfound a couch to sit on so that mom would not come out of the bathroomand see me with a hard-on. Bob was grinning like the cat that ate thecanary and I knew I was in trouble, again.When it was time to leave, Bob told me in front of my mother that I waswelcome to come by anytime. He said if I want to use his place to studyI could do that. When mom went to use the bathroom again before weleft, the conversation changed a bit. Bob said that he would beinterested in photographing me with some other young men he knew. Hementioned the word “masculine” when describing them. The whole time hewas talking, he caressed my ass. I felt like he knew my secret. I wasa bit nervous since I expected my mother to come out of the bathroom atevery second. What a weird situation to be in. He slipped a businesscard into my hand and said, “Call me.” Moments later, mom got out ofthe bathroom and off we wentI have to confess that I was pretty curious about all this, although atthe same time, to be hanging out at this guys house would be bad news ifit got back to my mother. Also, Bob was considerably older than I was,by at least 25 years. Despite any misgivings, I waited a couple of daysand gave him a call. He seemed very happy to hear from me and asked meto come over that afternoon. As usual, I had my red panties andstockings on underneath my clothes. I went to his house and he greetedme very warmly with a big smile and invited me in. We talked for whatseemed a long time and after a number of drinks and after swearing himto secrecy I told him my life story. He acted like he was veryinterested in hearing my story and kept urging me to continue telling itto him, though I was not sure at the time what his goal was.At some point he put his hand on my thigh and I was pretty sure wherehis hand was going to go next. Next thing, I knew he had his hand on mycock and he was kneeling in front of me. He unzipped my pants, pushedmy panties aside and pulled my cock out and started sucking my cock. Icame in seconds. Moments later, I stood up and took my outer clothesoff. Exposing my panties and stockings. I undid his belt, unbuttonedhis pants, unzipped his fly and attacked his cock for all I was worth.He too came in just a very short while and I swallowed his cum. Thisact was getting easier and easier for me.Since I had already told him my story about how I like to dress in girlsclothing and he seemed kind of turned on by it, I didn’t feel too muchanxiety at the time. He asked me if I wanted to come over another timeand have him take pictures of me dressed but that made me very nervousbecause I didn’t want pictures like that of me circulating. After all,it was possible that my mother would come by and see them and that wouldreally be a problem for me.Bob asked me if I would come by on the weekend. He told me that he had acouple of other young “masculine” male friends that were coming over andhe would like us all to get together. I told him I would come by. Heasked if I would come by and get dressed and I said that I would thinkabout it. He said that I could come by dressed normally and get dressedas a girl at his place. He also said that if I was a girl, that I mighthave a very nice time with his two other young friends.I did go to his house that Saturday afternoon and spent a fair amount oftime in his bathroom getting ready. As I have told you, I had reallylong hair in those days. I had a bra and breast forms, panties, thighhighs, short miniskirt, spike heels and a nice blouse that I put on. Ispent a lot of time on my makeup. I put on false eyelashes andfoundation and eyeliner and bright red lipstick. When I came out of thebathroom, I felt I look pretty hot. Bob’s two friends came over andthey looked like they were about 18 or 19 years old thin and built.They had apparently been over to Bob’s before and were quite familiarwith the place. In any event, they quickly took off their clothes andwere standing naked in front of me. Bob took charge and told me thatthese two boys were my dates for the day and that I should take care ofthem.Somehow I felt like I had no will of my own and I took a few stepstowards these two guys I had never seen before in my life. Next thing Iknew I was on my knees sucking the cock of the first of the two to get ahard on. There was a mattress on the floor and he pulled me onto it. Sohe was lying on his back and I was sucking his cock. The other boy gotbehind me and pulled my panties down and I could feel his cock probingmy ass. Next thing I knew I had one cock in my mouth and one in my assand both boys were pumping me for all they were worth. Neither of thetwo was very well endowed so I had an easy time on both fronts.Apparently, while all this was going on Bob had a video camera going.So I was being recorded for posterity without my knowing. The two boystook turns with me and I was their receptacle for what seemed like acouple of hours. When they were done, we all got dressed and the twoboys left and I got ready to say goodbye to Bob. He told me about thevideo and I got pretty upset since I told him I didn’t want him to takepictures. He showed me the video and said that he was only going to useit to jerk off, but then he said that he wanted me to come to his”parties” again. He told me that if I didn’t cooperate that he wouldshow the video to my mother.I didn’t know if you would or not but I felt like he was blackmailing meinto being a sex slave for his videos. Also, I wanted to know what hewas doing with the videos. I was worried that he might be putting themon the Internet. However he had me in the worst possible position and Ifelt like I was stuck doing whatever he wanted. Bob told me to show upthe next Saturday and to come fully dressed.I did show up the next week and when I got there, five naked collegeboys were standing around in Bob’s house. I went into the bathroom toput on my make up and when I got out Bob said to all of us, “Well, youknow what to do.” One of the older boys walked up to me and kissed me. I kind of liked that as it made me feel little less used than what hadhappened the week before. But that was short lived.Next thing I knew I was on my knees with cocks surrounding me. I wentfrom cock to cock keep it all five hard for a while. I then started toconcentrate on the boy with the biggest cock, sucking and squeezing hisballs. Pretty soon I could feel him tense up. He puled pulled his cockout of my mouth and squirted his cum on my face and in my hair. Withhis cum dripping down my face and onto my blouse, I then turned to thenext hard cock I could see and concentrated on it. In about twominutes, this boy blasted my face with his cum as well. A that instanta third guy who had been jerking off said “look at me” and sprayed medown with his cum.The fourth boy told me to lie down on the mattress and spread my legsand pulled off my panties. He lubed me up and entered my ass and Iwrapped my legs around him. As soon as he came in my ass, the fifthboy took his place and pumped me for all he was worth. Bob seem veryhappy with all this and I noticed that he had a camera in his hands.After all the sex was done, the boys got dressed and left. I was prettyspent and in the need of a little time to recover. However while I waslying on the mattress, Bob came over and unzipped his pants and motionedme over to his cock. I had cum dripping off my face and my hair and allmy clothes and also dripping out of my ass. My jaw was tired but Iopened my mouth and started sucking on the head of his cock. I guessthe show had really turned him on because it only took him about half aminute to ejaculate. When it was done I got up and went to the bathroomand cleaned up a bit. As I was leaving he told me to be sure to come bythe next weekend for “more fun.” I left his house wondering what I hadgotten myself into.Unfortunately a few days after all this, I started to get a sore throat.I had trouble swallowing and there were white spots on my throat. WhenI went to the doctor I was diagnosed with oral gonorrhea. I was prettyfreaked out. I called Bob yelling. I told him I didn’t care what he didbut I wasn’t coming back. Oddly enough he did not give me a hard time. I never did see any pictures of me having sex on the internet, but I amnot sure that I would know where too look. One comforting thought thatI had was that if the boys gave me VD, I probably transmitted it to Bobat the end of the day. I took my tetracycline and put away my clothesfor a while. I later was told that my HIV test was negative, so I had abit of relief, but this was a real wake up call about safe sex and whatI was doing. But the memory of the group sex really turned me on and Ithink that I was hooked on the adrenaline rush of it all. Talk aboutconflicted. But no death wish here, so I vowed to be more careful inthe future.At this point my life I was pretty much torn between my desires, almostcompulsion, to cross dress and have sex with men and clinging to whateversemblance of what was left of my former normal life. I am a bit of ahypochondriac, and was worried about disease. I had already learned mylesson regarding that the hard way. In any event I was hanging out at myapartment with my roommates and one of them came in with the campusnewspaper and was laughing about an ad in the personal section. The adsaid “free lodging and a Mustang convertible to use during the week inexchange for pleasurable weekends.” It went on to say that the personthat placed the ad lived in New York City but traveled to my townfrequently for business. While my roommates were making fun of this, itsounded like a pretty interesting idea for me.In any event I called the number that was in the ad and spoke to apleasant sounding man. He said his name was Malcolm and he was a doctor,and that he managed emergency rooms and hospitals and as part of hisbusiness, he came to my town pretty much every weekend. We arranged atime for him to “interview” me and I thought about how I would prepare.I did not ask him over the phone if he was looking for a masculineboyfriend but figured there would be plenty of those but I might standout if I should come fully dressed.In any event, I want the whole 9 yards. I put on panties, thigh highs,stiletto heels, very short miniskirt, and my biggest breast forms, verytight top and with the full make up including eyeshadow, false eyelashesand deep red lipstick. To top it off, I put on a beautiful blond wig. Ireally looked pretty hot. The big question of course was whether or notthe good doctor wanted a submissive girl or a masculine boy.I snuck out of my apartment and drove over to the meeting place. I rangthe doorbell and my heart was pounding. The man that opened the doorlooked to be in his early 40s, he was tall maybe 6’3″ and had verychiseled good looks. He was clearly surprised to see me dressed up as Iwas, but after the first look of surprise, he got a really big smile onhis face and invited me in.He asked me if I wanted anything to drink and I told him that a glass ofwine would be very nice. He brought me glass of Cabernet and we chattedfor a few minutes about his business and his marital status, which wassingle and how his interviewing process was going. He said he talked tothree other men but certainly nobody like me, and the way he said it heseemed very impressed with me. I finished my wine and he asked me if Iwanted another glass and I said not at the moment. He took my glass backto the kitchen and came back out to his living room. He sat down in achair and told me to sit wherever I like. I thought about it for a fewseconds and then decided to play this up for all I was worth. Instead ofsitting in a chair I walked over to where he was a knelt down at hisfeet. If he was looking for a submissive slut, I was the girl for him.If he wasn’t, it would not have worked out anyway.So I asked him, “Sir what do you expect from a person you wish to sharehouse with?” Unfortunately, he answered with a question. “What are youwilling to give up?” I told him everything. He stood up from a chairand I reached up and unzipped his pants. I pulled his rather large cockout, and kissed it with my red lipsticked lips. He got hard immediatelyand I toyed with his penis for a long time. I sucked on his balls and heseemed to enjoy that as well. I then started sucking his cock inearnest, and it did not take very long until I realized he was about tocome. I kept going and felt his cum hit the back of my throat. I justswallowed all of it and kept sucking until he pushed my head away.He seemed very pleased. He pulled me up to a standing position and kissedme very hard. He then took my hand and lead me into the bedroom. He hadme remove my panties and skirt and lie facedown on the bed. I felt himlube my ass up and then moments later I felt him enter me. This secondtime around it took quite a bit longer and since I was facedown, Icouldn’t use any of my usual tricks to get him to come quicker. But Iwas pretty happy and I was pretty turned on by how things were going.It may have been a casting couch kind of interview, but I got the job.We made arrangements for me to move in and in a week I had my very ownsugar daddy. I was to keep the house clean while he was gone and when heshowed up on Friday afternoons I was to greet him at the door on myknees. I was falling in love but it did seem pretty clear to me that, tohim, it was just an arrangement.One night, after we had been doing this for about a month, we weretalking for a bit. Malcolm asked me how much I wanted to be a woman. Itold him as much as possible. He asked if I would be interested intaking hormones and perhaps getting breast implants. I told him I wasvery much interested, especially in getting breast implants. All throughthis I dreamed about having large breasts. He said that since he was adoctor, prescribing the hormones would be easy and he would do it rightaway. He said he just wanted to read up to see what the doses would becorrect. He told me that he had a friend that was a plastic surgeon thatwe might talk to about getting implants.Needless to say, I started on the hormone regimen right away. I feltkind of odd physically at first and I didn’t see much difference otherthan my nipple seem to be very sensitive. However, after about threemonths I could detect changes in my physique. All this time mybenefactor was buying me new dresses and shoes to wear. He also bought avariety of restraints and toys for me to use. He bought a stainlesssteel collar for me that looked kind of like jewelry, but it was prettyobvious that it was a slave collar. When he was home, I would frequentlyhave to wear handcuffs and a ball gag in my mouth. I would make himdinner and kneel at his feet waiting for him to finish. Clearly hewanted me to be a serving wench.After a while, he took more and more control. He liked to control mybathroom habits too. He would lock my penis in a chastity cage and alsomake me wear a butt plug that was locked in place. In theory, I was onlysupposed to go to the bathroom when he said it was allowable. Of course,the bathroom control was only when he was around, however the chastitycage was locked in place constantly. There were times when I couldn’tcontrol myself and ended up soiling myself. When that happened he wouldmake me sit on my own filth and suck his cock first before I could go tothe bathroom and clean up.One day he told me to get in the car and said that we’re going to go meethis friend the plastic surgeon. When we got there, it was clearly notthe surgeon’s regular office hours. Malcolm told me to wait in thewaiting room and he went to talk to his friend. In a few minutes, hecame out and motioned for me to come in. I said hello to the otherdoctor and then Malcolm told me to take off my clothes. I was littlesurprised with this but at this point I was pretty used to doing what Iwas told and it was a doctor’s office after all. I got a pretty thoroughexamination and there was a lot of discussion about what medicalprocedures could be done. I didn’t really participate very much in thediscussion. The one thing I did say was when there was some talk aboutsize of implants and I said I wanted very big ones. However as soon as Isaid that, it was made clear to me that I was to speak only when spokento. Malcomb and his friend discussed breast implants, butt implants,laser hair removal, liposuction, and lip injections.To my great surprise, at one point Malcolm told me it was time to takecare of his friend. I started to ask what he meant, but in a few secondsit became pretty clear as his friend opened his zipper and pulled hiscock out. Malcomb told me to start sucking. I was just stunned by thisbecause up till now, it had appeared as if Malcolm only wanted me all tohimself. He got a little cross at my delay, and said just do it. So,dutiful slut that I am, I took care of the new doctor.After we left the doctors office, Malcolm explained to me that thevarious surgeries that he was talking about performing were veryexpensive. Instead of Malcolm paying the surgeon, the surgeon was goingto take it out in trade with me. Malcolm would have me for the weekends,and the surgeon would have me the rest of the week. This made me morethan a little nervous, as I was not crazy about being whored out formedical procedures, but at the same time I had bought into mytransformation at this point. In any event, I could see that Malcolm wasconflicted by this and I leaned over and sucked his cock on the way hometo console him.The first operation I got were the breast implants. They were not quiteas big as I would’ve liked but I was told anything bigger would’ve lookedlike cantaloupes glued to my chest since I didn’t have much breast tissueto begin with. Still, I ended up with a nice large C cup. I spent quitea bit of time with laser hair removal. Then came the lip injectionswhich I thought really altered my features quite a bit. The two doctorskept remarking about my cock sucker lips, but it was the one thing theydid to me I thought made me look a little odd and that looked like I hadhad plastic surgery. At some point, I realized I could never go home tomy parents again..The one real mistake I made one was when I signed a release form for anorchiectomy. I was signing release forms right and left and at one pointwe were talking about shaving my Adam’s apple and that’s what I thoughtit was for. Imagine my surprise when I woke up with no testicles. I wassomewhat upset but at the same time realize that this whole process hasbeen going on without a whole lot of input from me and that I was goingalong with everything so why not this too? Malcolm said that they did itso the hormones would work better. That did indeed seem to be the case. I never got the butt implants, however they did do liposuction on mystomach and injected the fat into my butt, which rounded it out nicely.I got to a point where, if I went out, I couldn’t walk down the streetwithout men whistling or making comments. Except for my limp penis andthe fact I had no vagina I was pretty much a girl at this point.My life was divided between the two doctors, although they each treatedme quite a bit differently. Malcolm was becoming a little meaner and alittle rougher. I suspected that he was taking out his anger at havingto share me with the other doctor on me. He started taking to slappingmy face during sex which I didn’t like all. I was completely on boardwith getting spanked but slapping in the face was bad.The other doctor like to have parties. He would invite friends over andhave me serve them. At first I was mostly window dressing. The one nightwhen I asked one of his guests what he wanted, he responded with beer anda blowjob. I gave him a beer and walked away and the doctor accosted meand said why aren’t you giving him the blowjob he asked for? I startedto protest but he said just go and do it. Next thing I know, I’m givingblowjobs to everybody in the room and then a short time after that I’mface down on the bed pulling a train.The doctor said I was to not to tell Malcomb any of this. And thisstarted a period of my life where for a few months, at least once a week,my doctor friend would have a party with anywhere from 5 to 10 peoplewhere I was expected to service anyone that wanted it.Unfortunately between the hormones and the castration, my own sex drivehad very much diminished to nothing. Where in the early stages of thistransformation, this sort of thing would have turned me on like nobody’sbusiness, it just didn’t do anything for me at all. I could not get anerection anymore and no amount of tugging would give me an orgasm. I hadhad some girlfriends in the past that told me they were frigid and Iguess I could sense what they must have been going through.It had now been almost two years. I could sense that things were goingwrong in many ways. Malcomb was getting meaner and more distant and thegood doctor was getting more and more perverted. Maybe I just needed arest, I don’t know. I had no money, and had dropped out of school. Ihadn’t seen my parents in all this time and figured they would probablyhave a heart attack if they saw me. I needed a plan.Malcomb was only coming to town two weekends a month at this point. So Ihad a couple of weekends to myself. I started placing ads in the localclassifieds whoring myself out. I found that the going rate was $200 perhour. I advertised a girlfriend experience, though business was not toobrisk. It seems that most men looking for a walk on the wild side wantthe transsexual to top them, or at least be “fully functional.” Thatwasn’t me. But for those generous men that wanted a submissivegirlfriend that would do almost anything, I fit the bill nicely and Ifound I could make anywhere from $600 to $1200 on a weekend. At onepoint, I found a fellow that wanted me to spend the night and was willingto pay nicely for that. I managed to squirrel away some get out of townmoney pretty quickly.I bided my time. I figured the best time to leave was on one of thoseweekends when Malcolm was not in town. I figured I could get a headstart and get out of town before anyone noticed. I am not sure why I wasacting like I was in prison. I pretty much had free reign when either ofthe doctors were working. But I just didn’t know how they would take itand didn’t want the confrontation. I had long ago found the key to thechastity cage and at that point it was more self imposed than anything.In any event, the surgeon dropped me off at the house and I wrote a noteto Malcolm saying thanks and that I was heading to Florida (I was reallygoing to California) and goodbye. I paid cash for a bus ticket to LosAngeles and got on the bus. And off I went on my next adventure.
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