The Shemale Diaries

I suppose that technically, I had already had my first real date when I went out with Steve back home but I really did not consider it to be since I had already fucked and been fucked by my athletic friend and it was more a show than anything else.
School had settled down and over the couple of months following that horrible first day, I managed to keep my head down and out of trouble. I had passed the registrar in the halls on a few occasions and, although nothing was said subsequent to them saying that I could not attend university as a shemale, he always addressed me with a side-ways grimace and the name Colleen always seemed to stick in his throat. On one particular day as I was coming out of my advanced physics class, he stopped me in the hall and asked me to come to his office. The first thing I thought was that the son of a bitch was about to blow me out of school. I followed him to his office trying to think of my response and how I would deal with him and inside, I sat across from him.
“Colleen,” he began, “you know I am not big on you being here as a shemale but I have been following your progress and I am impressed by your intellect as are all of your professors. We have a guest professor coming from the west coast late next week who is lecturing in another discipline but he has asked us to fix him up with someone to take to the Met for a Pavarotti performance. He is gay but has not come out of the closet because it would kill his perceived integrity so he asked if there were any shemales that were not boys trying to look like girls. It did not take us long to think of you and since you look nothing like a boy trying to be a girl, we told him we thought we had just the right young lady for him.”
“Gee thanks,” I said unsure about how to address the slight-handed comment. Since I too loved the opera and was a big fan of Pavarotti, I told him I would be delighted to accompany the visiting prof but was not guaranteeing any additional benefits after the opera. He assured me that there was no pressure for any extracurricular activities and his primary focus his to have a woman on his arm for the opera. I agreed and the registrar said that my opera date would pick me up at 7 on the following Friday evening.
When I got home after school, I told Linda my exciting news and then gasped. “I have nothing to wear to the Met,” I declared. “What am I going to do sis?”
Linda smiled that knowing smile and replied, “I think me and my girlfriend need to go shopping.” And did we ever shop. It took us all day on Saturday but finally found this sweet black gown that fit perfectly and, of course, the purse and high heel pumps to go with it. I had played with high heels before but this would be the first time I had worn them outside, so I practiced every chance I got. By the next Friday I was ready.
Linda and I started right after school getting me ready. She helped me make sure that there were no stray strands of hair around my cock and I shaved my underarms. This time, I really took my time putting on my makeup and once I was dressed my sister simply said, “Wow Colleen, you look awesome.”
The limo driver called up and I went down to the lobby where my gentleman date was waiting for me. Like David, he did not look or sound gay but he was clearly more dignified than my friend back home. “I am so glad you agreed to do this for me,” he said calmly. “Do I look alright?” I asked as my confidence wavered ever so slightly. “You look amazing Colleen. I know who you really are and I would never think that you were anything other than a beautiful woman.” I could feel the blush rising in my cheeks beneth my makeup as he extended his arm for me to slip my hand into. Professor Wainthrop was a consummate gentleman. He held the limo door open for me and helped me inside and then slipped through the wide opening to sit beside me. We immediately got along well. As impressed by his intelligence as I was he assured me that he was equally impressed with mine but what I did not say was that although he was twenty years older than I was, this man was really really hot. He obviously worked out a lot and his grooming was impeccable. As we pulled up at the main entrance to the Metropolitan Opera House, I was beginning to think very seriously about whether he manscaped right down to his cock.
The opera was incredible and to hear my idol in person literally brought tears to my eyes which seemed to inflame my date’s desires more as he softly stroked my thigh causing me a bi of discomfort. It was not as though I did not want the attention, but he was really beginning to turn me on which, when your cock is tucked securely under your bum, it can be a bit stressful. After the show was over and the dim lights were turned up, he asked if I would like to have some dinner at one of the finest restaurants in Manhattan. I quickly said yes. After dinner, he grew silent and, as we sat in the back of the limo I asked if I had done something to offend him. It was his turn to blush and he said no but he was trying to muster the courage to maybe ask me back to his hotel room for a night cap. Now you have to realize that I had been the proper young lady all night - well as proper as any shemale can be - and it startled him when I leaned over, kissed his cheek softly and replied, “I would be really disappointed if you did not. I have to be honest, “I whispered seductively, “I can’t wait to get out of this dress.” The tension relieved he said, “I can’t wait to get you out of it!”
Inside his hotel suite, he took off his tuxedo jacket and poured us a drink. “You look uncomfortable,” Ron said to me. I smiled in response but playfully said, “A young lady cannot get undressed before the man. It would not be proper!” He was on his feet in a heartbeat and stripped down to his boxer shorts. I was right about Ron Wainthrop working out. His belly was rippled like a six pack and his chest was so strong and muscular. I needed to hold him and beckoned him to come to me and then reached into his fitted boxers and wrapped my fingers around his swelling dick as I placed a delicate kiss on that sweet belly. I removed my hand and stood up asking him to unzip the long zipper on the back of my gown and he did. His hands felt so good as he slid them between my dress and my own flat tummy and then moved up to encase my bra covered titties. I was in heaven. I was being treated like a woman by a guy who wanted all of me. I took off my dress and stood before him in my thong and my matching satin bra and my high heeled pumps that only served to so exquisitely define my legs and I could see that Ron loved what he saw. Then, I climbed onto his bed where he joined me after he slipped his boxers off and showed me his very neatly groomed cock. Boy was he good at manscaping and better yet, he knew that he was about to put that hard cock into a very horny shemale. He was a lot bigger than Steve was an his cock kept pulsating from his excitement which really turned me on. I could not wait. I reached out and took that hot thick flesh in my hand and immediately began stroking it while he rubbed my tits through the bra that I was still wearing. My own dick was beginning to strain to get free of my thong and as I began to lick his sweet stick, I began wiggling my way out of my confines until I was finally free. Ron and I slumped onto the bed where we shared the fun of sucking on each others hard cock until I could not stand it any more. “I want you to fuck me so bad right now sweetie,” I purred when I took my mouth off his cock. “Me too,” his voice raspy from desire replied as he moved around while I lifted my feet over my head. Ron was a great lover! He started off by licking my perky little ass until it was nice and wet as his hands kept fondling my balls. Of course, I was playing with my tits all the time. Then, I closed my eyes tight as he began kissing his way up my tummy and then sucking on my titties. I could feel the swollen head of his cock now pressing against my ass and I wanted him. I reached down and grabbed his hips, pulling him forward until he started to spread my hole. I was so excited that he pretty much slipped right into me. The sensation of my own cock trapped between our bodies as he fucked me hard was way too much for this beautiful shemale and before long, he was loading my ass with his man cream and I was squirting mine between our bodies perhaps sticking us together for all time. That night, we had sex three more times together and then we showered and went to bed for the night as he held me close to his warm bodies. I knew then that being a shemale was the only way I would or could be. Before Ron left for home, he asked if he could see me again and I told him I would always be there for him when he came to town. Since he was such a great lover, why would I say anything else. I can still feel that delicious cock caressing my ass.
There will be more about Ron later in these Shemale Diaries so stay tuned. In the meantime, if you would love to meet a hot beautiful shemale like myself (or maybe you will even meet me) why not check out one of the very best Shemale Dating sites around. I am a shemale and I swear by this site. Trust me, the trannies you will find in your area will have you begging for more.

Take care for now and I do hope you will visit again.
All my love
Colleen

Linda woke me really early on the morning of the first day of school. My nerves were raw from a sleepless night and anticipating every possible problem that could come of me being outed by some bastard professor. I had nightmares about the registrar coming up to me in the middle of a crowded corridor, grabbing me by the cock and marching me out the front door telling me never to come back. However, I was determined to do this and two hours later, Linda looked at me and smiled telling me that I was perfect. Dressed in my mid-thigh pleated skirt and sweater, Linda and I left for school. Before my first class, I went to my firs professor’s office and explained to him who I was and asked that he address me by Colleen in class if he were to address me at all. He was an old school professor and I figured he would tell me to fuck off particularly since my first class was anatomy and he was sure to laugh me out of his office. He did not though. He told me it took a lot of courage to come forward and that he would try to help as much as he could. Needless to say, my first class was great and my prof was true to his word. Because of him, I was able to focus on the work and take part in his lecture lab without concern. The second class was much like the first and I began to let my guard down thinking that they would all go the same. I was suddenly wrenched back to reality when, upon meeting with my third professor of the day he literally told me to fuck off. He was younger than the others and a real red necked ass hole who figured that when not in use, guns should be used to pick his teeth and women were there only to fuck and get a blow job if fucking them was out of the question. Nervously, I went into his lecture hall, and it took the bastard all of two seconds to out me causing every pair of eyes in that hall to focus on the fucked up guy in the middle of the room. Amid whispers and nervous laughter of derision, I mustered my courage and spoke to all of them and snidely berated the professor for being a jerk who promptly got into a huff and threatened to kick my ass out of class. A couple of red-necked jocks at the back of the lecture lab jeered and taunted me but I was determined not to back down. Most of the students though simply had “so what” attitude so when I sat back down, the class went along as usual. After class, a couple of the girls came over to me to check me out. They collectively agreed that I should have been a girl and I had done a good job in hiding the boy parts. As they talked, I could not help noticing the gawkers as they stared and snickered at me but I didn’t care. I was there, after all to be educated in my chosen research discipline and nothing else mattered. Sure, I hoped that I would be accepted but I knew better than that. I knew there would be some tough times ahead and that I could even be beaten to crap.
After classes were done, I moved hastily across the street from the campus to have a wee and a coffee. It was there that my worst fears were recognized. The sneering assholes from my last class it seemed had followed me off campus and were about to teach me a lesson. They formed a circle around me and started with the jibes until one aggressive bastard decided to try it on and pushed me. He wasn’t that much bigger than I, but he had decided that since I was a poof, he would have no problem in kicking the shit out of me. When I turned to confront him, his fist landed on my cheek and sent me reeling backwards but the others in their little bashing party promptly steadied me only to send me back towards the primary foe. I tried not to get upset and maintain my dignity but I knew that he would not let up. I ducked and dodged his next three attempts at hitting me all the while trying to reason with him. Of course, being a bully son of a bitch, there was no reasoning with him and I decided it was time to protect myself. I knew I could not take them all but I could inflict enough damage before they had me completely. Those eight years of Kung Fu training that my father had insisted upon kicked in and hurt my foe and dropped him to the ground and readied myself for the next attack that came in the form of three. I punched and kicked with great control and was about to inflict more serious damage when the sound of an approaching siren stopped them short. Slightly dissheveled and blood trickling from the corner of my mouth, two police constables quickly got out of the car and began to forcefully break up the tiny gathering. In response to one of the officers saying with a high degree of disgust that these ruffians were beating up a woman, one of the boys said “she is a guy”.
“And your point is?” the female officer asked as she radioed in for backup. “Well, he’s a fag,” the moron said. “That gives you the right to beat up an innocent person does it?” the officer asked as she handcuffed his hands behind his back. “You are under arrest,” she said calmly yet forcefully. “Officer,” I finally broke in after rationalizing the consequences of their arrest. “I prefer not to press charges. I clearly am a novelty and they decided a good target. They are also obviously pretty intelligent to be going to this university in the research sciences so I would like to let this pass just for this one time.” The constable and her partner warned against it but at my insistence, they released the handcuffs and then lectured them on the need to use their brains and if they should respond again to such an incident, they would press charges and make sure they paid dearly for their actions.
Nursing my cheek and wiping away the blood, I turned my back on them and began the walk home knowing that they had no idea why I had done what I did. When I finally reached my bedroom, I collapsed on my bed and cried partly because of the horrible day and partly relieved that I was not killed by those ass holes. When Linda got home, I vented my doubts that had been simmering in my mind for the rest of the afternoon and, after listening to me she finally sighed and softly said, “But you made it through sweetie and now there is no turning back.”
Next time on The Shemale Diaries, I am going to tell you about my first real date with a visiting professor. In the meantime, if you want to take a look at one of the neatest shemale sites around, take a look at

All my love
Colleen

I was literally over the moon when I returned to the apartment my step-sister and I shared. Apart from really having a great time with Steve and really being able to explore sex the way we wanted to, I convinced myself that the new me, the real Colleen, was perfect for the world.
The following day was going to be a huge day for me. It was not possible for me to attend the classes as a female unless I met with the registrar to both explain my situation and to change the name on my admissions. Although I had already applied to have my name changed from David to Colleen and was awaiting the court date so I could stand before a judge, it would not be until after the semester started and it would not be “a good thing” to become Colleen before my fellow student’s eyes. I got up in the morning full of hope and not seeing a problem with this being done since it would be legal soon anyway and, as I sat in the registrar’s office as Colleen, I waited with baited breath.
Finally, I was shown into his office and he asked, “What can I do for you young lady?” He seemed friendly enough even though he was a big man and in his late fifties, he appeared, on the surface at least, to have an open mind.
“I need to change my registration,” I said confidently.
He looked at me and asked my name and when I said David, he looked at me oddly, his already pale skin went stark white. “Explain yourself,” he commanded suddenly changing from mild to judgmental. I explained to him that although I was born male, I really was female inside and assured him that I had applied to the courts for a name change. His pronounced frown sent a dark pall over his desk and he asked simply, “Physiologically, what are you?” When I told him that I was male, he rudely chuckled and asked, “So where are you going to the bathroom boy? You sure are not going to use the girls facilities and you are certainly not going to play any female team sports. I do not see this as practical.”
To be honest, I had never thought of going to the bathroom or taking a piss. He was right that I could not use the men’s room but to bar me from the girls’ was not fair. “It isn’t going to happen son,” he said with such condescention it sent a shiver up my back. “But,” I began to protest before he cut me off.
“Do you know what would happen if a female student complained that there was a pervert using her toilet? Beyond that,” he boomed, “How in the hell do I know that you have no interest in women? How do I know that you don’t want to secretly take pictures of naked girls. It is not going to happen. You are David! You are a male and that is how you will be registered if you want to go to school here.” Suddenly, his tone softened and, as he read the computer screen with my scholastic data said, “It would be a shame to lose such a bright mind though.” After telling me he would have to confer with the university president and the legal department he said that the school would advise him of the outcome before the school year began. “Him,” I thought knowing that the sneer on my face was obvious. “Look at me man, do I look like a him to you? You sexist unrelenting bastard,” I thought. I stood and left his office.
When Linda go home later in the day, she found me in my room crying inconsolably. When I told her about my meeting with the registrar, she wrapped her arms around me and held me like a mother holds her daughter. “What am I going to do?” I sobbed. For two weeks, I could not shake the misery I felt in spite of my step sister being such a sweetie. When the letter finally arrived, I ripped open the envelope with guarded optimism. Surely they could see I was a shemale. Surely they would make some kind of concession for my plight. As I read the letter, my eyes filled with tears. They could not see that I was a shemale and they would not make any concessions. Even after I had my name legally changed, they said, would they allow it simply because of the bathroom shit. I had no idea what to do. Would it be wise to be my shemale self and have professors address me as David? I could handle the jeers from fellow students since I had gone through school being the class geek and they always made fun of me. Now I would be surrounded by adults and if one of those adults happened to be some bible thumping hypocrite who thought the answer to shemales was beating them to death, could I handle that? Dejected and depressed, I curled up in my bed for three days straight and not even Linda could get me up. If I needed to pee, I got up went, and then returned to the safety of my bed. On the morning of the fourth day I awoke and yelled out, “Fuck all of you! I am Colleen NOT David and I will be damned if you bastards are going to ban me from school. Tough shit if any of you don’t like it. Give me your worst and I will fucking well take it.”
I got up and dressed then I walked the campus. I found that there were three placed on or near the campus where they had single bathrooms that I could go into. There was a small coffee shop not more than a ten minute walk that I could go to and use if needed. So if the bathroom was the problem, I just solved it so, defiantly, on the first day of school, Colleen got dressed and went in for her first day of university as a Shemale and I would deal with everything else after. It would have to be the registrar to keep me out of school because I was going to learn to be a scientist and I was going to do it as Colleen and if they did not like it then they would be the ones to expel me. “After all,” I thought, “I could always be in porn movies.”
Next time, I am going to tell you about my first day of university and the bad shit that happened as well as some not too bad stuff. In the meantime, if you want to check out one of my very favorite porno sites that is pure Exotic Shemale heaven.

Thank you for visiting me
Colleen

As soon as I could, I moved from my parents home and into Linda’s apartment. In all, we had two and a half months to prepare me for the world and the one thing I wanted to be, was perfect. I had stopped getting haircuts just after Christmas much to my father’s chagrin, but I refused to cut it and neither my father or mother could understand why a young man who was always so neatly groomed would now decide to go shaggy. How could I tell them I was turning into a woman before their very eyes? As soon as I moved in, I started doing my hair properly while Linda helped me completely to wax all of the hair from my body including my face. Fortunately I was blessed with a pretty light growth of hair on my face and never had one of those five o’clock shadows, but the beard definitely needed to be dealt with. Waxing my face was just short of torture but I was a shemale on a mission and soon it was over. I decided after it was over that as soon as I could afford to get electrolysis on my face I would and that would put an end to this torture forever. With my eyebrows plucked and shaped, Linda stood back and looked at me and nodded with a triumphant smile. “We need to get your hair properly done,” she said and immediately picked up the phone to make an appointment with her hairdresser who just happened to be gay. She made the appointment for a week later so she and I could go do some shopping for clothes. My step sister had impeccable taste in clothes and every time I tried something on, she made sure that it was right. I would, after all, be wearing these things to school and on the street so they had to fit right. There is nothing like going out in a pair of jeans and having a cock bulging out when you don’t want it to.
The only thing left to do was to get rid of all of my pubic hair except for lust a thin wispy line that I wanted pointing down to my cock. I tried to do it on my own but found it hard to see even surrounded by mirrors so, once again, I looked to my sweet step sister to jump in to the breach and to help me. I must admit that as I grew closer to being a woman, I was becoming more self-conscious about Linda seeing me naked but this needed doing and I stripped naked in front of her. She went right to work and in spite of my screeches of pain, continued to wax away the hair including the stuff that gathered around my sphincter. Doing my balls was a challenge. For one thing, having someone’s hand playing with my bag got me excited even though it was a girl but Linda was not distracted from her task. Soon, my balls were as hair free as my legs, my ass, and my chest and she moved aside to let me see my reflection in the mirror and asked if I approved. “How could I not?” I asked looking at the soft hairless skin. My cock was rock hard partly because of my anticipation in being hairless and partly because my sweet Linda had been playing with my cock and balls to get me that way. “We cannot leave you like that,” she observed casually. “We need to see what you look like when you are soft.” Without saying a word, Linda knew that I was always up for a blow job, even by a girl, so she wrapped her lips around my cock and sucked me dry and made sure that not a drop of cum would escape her throat. “You can be such a little slut,” I said still reeling from the orgasm. A wry smile grew over her face and she answered, “So can you Colleen! But now I need to get some of that girl love.” I knew what she meant. We went into the bedroom and lay down on the bed where I sucked on her tits as she played with mine and finally worked down to her ass where I licked and probed it wit my tongue.
Ever since that first time I fucked her pussy and told her I would never do that again, we made an agreement that she would deal with her pussy as long as I did not mind putting my cock into a girl’s ass or sucking her tits. For the time being I agreed to that and so, as she fingered her wet girlie part, I rode my step sister like a puppy in heat until I filled her bum with more of my goo.
The following week we shopped and the day of my hairdressing appointment, I dressed under the watchful and critical eye of my step sister. Once I was all done, she examined my makeup and said I looked good and in fact better than a lot of her girlfriends. The test would be the hairdresser. He would be the first person other than Linda to see me as a girl. Would I pass the test? “You didn’t tell me he was so hot,” I whispered in my sister’s ear when she introduced me. I sat down and he ran his fingers through my hair shaking his head slowly. “We need to do a lot of work my dear,” he said clearly up to the challenge. He worked for over a three hours and when he finished, he unveiled an absolutely gorgeous do and a whole new me. “You are going to have all the boys clambering to be with you Colleen,” he said causing Linda to laugh. “Oh,” he said correcting himself, “Are you gay?”
Linda came up to him and leaned into his ear and whispered, “Colleen is my step-brother. I don’t think all of the boys are going to be chasing him.”
“No chance, are you really a shemale?” he asked almost hopeful.
“Yes,” I replied. “Do you like what you see?”
He said he did and invited me out for the night to introduce me to some of his friends as a coming out gift. That night was nothing short of amazing. Colin took me to one of his favorite clubs and introduced me to a lot of his friends who, at first, thought I was a girl. We partied and drank a lot and when it was over, Colin took me home, kissed me good night and left making sure that we could go out again so we could experience a more personal coming out. Linda was up and waiting for all of the details and after I told her what had happened, she said, “You go girl!”
There is one more test I want to make before I go to he registrar and tell him to change my name on file. I need to go back home and get together with Steve. I know mom and dad will recognize me right off the bat, but if I can fool Steve and have him take me out as his girlfriend, I will know that I am perfect.” With that, I called Steve and told him I was coming to town the next weekend and wanted to know if he wanted to meet me at the hotel restaurant. He readily agreed. I was sitting there when he came into the dimly lit restaurant and I sat watching him from the bar. He looked around for me and when he could not see me he sat waiting at the bar just four stools away. After ordering a drink, he looked at me and asked if I were waiting for someone and I said that I was and asked him the same thing to which he said yes. “Well,” I said, if we get stood up we could always get together.” Steve gave me a weird look and said, “I don’t think so!” I studied him closely and asked, “Are you gay?” He averted his eyes from mine but said nothing. Conversation turned to other things as I moved to sit beside him until I could not take it any more. “Screw it!” I hissed softly. “What’s the matter?” he asked. “Screw dinner Steve,” I said. “Let’s go up to my room!”
Suddenly the penny dropped in his mind and Steve realized that I was not a woman but his old friend David. “Colleen, is that you?” he asked hopefully. “Yes sweetie,” I said, “It is me!”
In the light of the room, he told me that he had no idea it was me and even as he stood there looking at me he was having a hard time seeing the old David. When I took his hand and guided it to the now pulsating bulge beneath my dress, he grinned openly and then he slowly began to unwrap his new present. That night, we fucked and sucked and made love like we had never done before and before he left the following morning asked me to go out with him that night to a sports banquet as his date. The date was perfect and no one knew that the girl Steve had brought was really a shemale and when we got back to my hotel room, he sucked my cock until I exploded all over him. My plan had worked and the new shemale Colleen had been introduced to the world.
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Thank you for visiting me
Colleen

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There were times, until Linda left for university, that I was sure she was going to spill the beans about who I really was but every time, she kept quiet and assured me every night that she was well into keeping our little secret. Until she left, she gave me a crash course on being a girl every chance she got. She showed me how to walk, talk and hold my hands without looking like I was some effeminate gay. She also told me not to wax my legs until I moved in with her the following year. It’s funny, looking back, I was about to do the waxing and never thought that when I was in the shower room after gym class, I would be more than obvious to the other guys. Shaving around my cock was not that big a deal since the jocks did it anyway so that their dicks looked bigger. Throughout the last year of high school, I worked hard on my grades, worked harder on my feminine side and worked even harder not to reveal my little secret to my parents. In her wisdom, Linda took the bra set she had given me with her and assured me it would be there every time I visited her. I visited Linda once a month and our parents were so happy that we had such a natural brother and sister relationship and that we wanted to spend time together. It makes us smile even today!
It was in that last year of high school that I also had my first sexual experience with a man. One day, my chemistry teacher asked me to stay after class to talk. I knew I could not be in trouble since my test scores were almost always perfect in chemistry and all of the other maths. He told me that one of the boys on the football team needed to get his grades up and suggested I tutor him and I agreed. I knew Steve to see him and always thought he was hot but he was always surrounded by the girls as most typical football players are. Anyway, we made arrangements to meet twice a week and for three weeks it was all business. Steve was not stupid, just distracted by his “jock” life and he picked up the basics of chemistry pretty fast. My parents were going to be going away one weekend and I suggested Steve come over if he had the time and we could spend all day Saturday working on it rather than an hour here or there. He quickly agreed and it wasn’t until later that I realized why. As agreed, he showed up just before my parents left and met my dad and stepmother. “No parties!” my dad ordered. “Oh no sir,” Steve countered, “it will just be the two of us and we will be studying hard.” My parents left and as we always did, Steve and I got down to studying. Two hours later we needed a break and we went into the family room just to kick back and talk. I had no grand dillusions that Steve saw anything in me othe than his tutor. After all, he was a jock and had his pick of any babe in school but something deep inside me wished that I had become that girl before I started my last year. But I did not let on that I wanted him.
We were joking around on the sofa and having a laugh when suddenly, he leaned over to me and kissed my cheek. “What the hell?” I asked seriously.
He could see the horror in my eyes and said, “Sorry man, I thought you were gay! I have been watching you for a long time and I thought that you liked me - you know!”
“Steve,” I probed, “Are you telling me that you are gay?” My biggest concern was that he was not gay but only trying to rack up a good story for his football buddies. Steve nodded slowly! “But all of those chicks,” I countered.
“Well, I have to put on the show right? I prefer boys and although I have fucked a couple of babes, I have never really had a guy before because I have been a chicken shit. But you are different. I like you a lot and I have seen you in the shower room and I like what I see.”
I was more than a bit skeptical and as much as I wanted to jump on his body, I was also very worried that this might be a trap and I told him so. Without saying a word, Steve stood up and began stripping until he stood in front of me completely naked. It was the first time that I had seen a hard cock other than mine and it was definitely hard. Nature took over and my body seemed to lean closer to him until he could feel my warm breath cascading over the pulsating head of his cock. “Oh that feels so good,” he said. I did not need any more encouragement. I leaned ever closer and my lips made contact with his hard cock and I naturally began to start licking it and examining this hard beast like I had always dreamed. He placed his hands on my head and gently pulled me towards his hard dick; my mouth opened and as my fingers now danced along his shaft, I began to administer my very first blowjob to the sounds of his deep passionate moans. “Can we go to your bedroom?” he asked. Without a pause, I released my lips from his cock and led him upstairs to my room where I quickly turned down the bed, removed my own clothes to expose my cock that was harder than I had ever known. When we climbed onto my bed, I was still hungry to taste his cock and more importantly, his jizz and I immediately went down on him to resume my virgin cock sucking. As I cradled and massaged his balls in my hand, I could feel them begin to rise and knew I was about to receive the white foamy cum and sucked and lapped at his dick even more furiously. He moaned long and loud and suddenly, I felt him explode in my mouth until the cum trickled down my chin. He had blown his load and now he wanted to have mine. He lay back on the bed and spread his legs, lifting them above his head. Instinctively, I knew what to do. I wiped the cum that I had not swallowed over his tight little ass hole and got it wet. When my finger slid into him without resistance, I aimed my hard cock and began my first expedition into fucking a hot guy. As much as I wanted to blow my load, I needed a cock in my ass. I knew that would feel right and before I came, I pulled out of his tight sphincter, knelt face down on my bed and panted, “I need you to fuck me real hard Steve!” He mounted me in a heart beat. The searing pain was meaningless as he rammed his cock deep inside my ass and humped me like a rabbit in heat until he came once again. While he fucked my ass, he reached around and grabbed my cock and with every push of his cock, he rubbed on my cock until we both exploded together. Steve was as hungry for sex as I was that first day as we both lost our virginity. After I had blown my load all over my sheets and Steve’s softening cock slipped out of my ass, he knelt over my cum load and he ate it telling me he wanted to taste me like I had tasted him.
For the balance of the day, Steve and I fucked in every room of the house including in Linda’s bed. We talked a bit and I told Steve about my desire to be a shemale which really turned him on. He said that if I looked like a girl, we could date all of the time and no one would know he was fucking another guy or that he was gay. I told him I could not do it yet but maybe by the summer. In the meantime, we could study more than chemistry whenever we were alone and he quickly agreed. The following afternoon, after I finished tutoring him, he undid my pants, slipped them down and gave me another blowjob saing that he needed to drink me one more time before going home.

Linda was thrilled that I had finally lost my cherry and as she had promised to do, by the end of the school year, she had me to the point where I could almost greet the world as a woman. When I moved in with her a month later, the metamorphosis would be complete.

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It was the weekend before my eighteenth birthday when I really started to learn how to be a woman. My father and his wife had gone away for the weekend leaving me and my stepsister to fend for ourselves. Now you have to realize that Linda was beautiful by anyone’s standards and the two of us had always gotten along great. From a sex standpoint, I had no interest in her but I did have an interest in her body which, to me, was the kind of body I wanted with the exception of course, she did not have a cock.
Anyway, on that weekend with my parents out of town, Linda had planned on going out with her boyfriend. Linda, a year older than me, was off to university in three weeks and would be a four-hour drive away. The only good thing was that I planned on going to the same university the following year and that would make a huge difference in my life. I had no plans for the night since I did not tend to date and when you are a boy in high school who is more interested in men than women, you do not tend to date guys for fear of the fallout. Linda kissed me on the cheek as she left and I curled up in the family room watching a movie. Halfway through the show, I felt the need to get dressed in Linda’s bra and panties and so I went upstairs. I stripped naked in her room and pulled the bra and thong she had discarded in her hamper and put the on. God I loved the way I looked. I pranced around her room and then picked up her perfume bottle and dabbed a bit on my neck just like I had seen her doing it. I felt electrified and I was also starting to feel horny. Rather than getting her in trouble again, I slipped the thong off and my cock stood hard in my hand. I watched in the mirror as I jacked off in my bra that perfectly squeezed my little tits and forced them into a pretty awesome cleavage for a guy trying to be a girl. I was coming along pretty good when I heard the door downstairs open and then slam shut. I quickly pulled off the bra and slipped them back into the hamper and then, after picking up my clothes off her bed, raced to my room with my hard cock swaying from side to side as my little bum quickly wiggled through the hallway. I was not expecting Linda until well after midnight so her return was a surprise.
She knocked softly on my bedroom door as my t-shirt cascaded over my slender shoulders and I invited her in. Linda was obviously upset. She told me she dumped her boyfriend because all he wanted was sex before she left for university. Linda was a smart girl and she knew there was no future with the jerk even though she was horny as hell she told me. She sat on the edge of my bed and cried; then she suddenly stopped and looked at me with a look that I had never seen before. “What’s wrong?” I asked.
“Do you ever have sex David?” she asked.
I could see the reflection of my discomfort in her eyes as I tried to explain to her that I was a virgin. I don’t know why I kept talking though. I felt the need to finally tell someone about my feelings and since I trusted Linda and really loved her as a sister, I began to tell her about my desire to be like her physically causing her brows to furrow in disbelief. “Are you saying you are gay?” she asked but without an judgment.
“I don’t know, I have never had sex with anyone. I just know that I like to wear your underwear.” Oh shit! I let the cat out of the bag but Linda was not surprised at all. “I thought someone was putting on my undies,” she said with a smile. “Come with me,” she said inviting me to her room.
Linda did not close the door when we entered. She simply told me to strip. When I stood naked in front of her she went to her dresser and pulled out a satin bra and a matching thong. When asked if I had tried these on I told her no and she wathed as I put them on. All the while her eyes were glued to my cock which, although it wasn’t hard, was still big and she told me so. When I had her undies on, she came over to me and reached into the thong and pushed my cock between my legs and aranged my tits in the bra so they looked great. As her hands pushed and prodded me, I got hard and she knew it. “Look at yourself in the mirror,” she said and as I did, she took off her own clothes down to her undies. “You would make a beautiful girl,” she said with such a supportive tone I hugged her. The feeling of her body pressed against mine, and mine hers, got my cock a little hard and I could tel that she enjoyed it too. Then, Linda led me to the bed and said, “Let’s talk like girlfriends,” and she put her feet up and I joined her. I could see why her boyfriend wanted to fuck her so badly. She was really hot. As we lay on the bed just talking and her giving me suggestions as to how to be a better woman she suddenly asked if I had ever tried having sex with a girl. When I told her I had not, she slipped off her thong and her bra and then she took off mine. It as the first time in my life that a hand other than mine was on my cock and it did respond quickly. Linda quickly sank to my hard cock and began to lick the shaft and head while I eagerly rubbed my hands over her round firm tits that, to be honest, I wanted to have as my own. As she sucked my cock, I examined her nipples as the got hard and watched as she sucked like a woman and wanted to try. That night, was the first and last time I have ever fucked a woman although after that night, Linda and I would often sleep naked together but it was always like two girls sharing a sleepover. The next morning when we got up, Linda began to help me become a woman. She shaved my legs and most of the hair around my cock. She even began to show me how to put makeup on but suggested that I be careful with that around mom and dad and certainly around school until I had it refined. She told me to come up to her once a month and she would continue the lessons until I moved in with her the following year at university. Somehow, Linda seemed almost more excited about me becoming a shemale than I was. I would be the girlfriend she always wanted. Until she actually left for university, Linda taught me how to act and walk and talk like a girl every chance she had when my parents weren’t around.
On my birthday after Linda knew my secret, she gave me a secret present late that night when the folks were asleep. She crept into my bedroom, slid into my bed and said, “Open this one sweetie.” She had bought me my very own satin bra and thong set from Adorably You where she bought all of her sexy things. I kissed her and held her tight as the tears welled up in my eyes. I felt her hand touch my cock but it was not for sex. She knew it made me happy when she touched me.
Stay tuned for the next instalment of The Shemale Diaries.
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After I tried on my step-sister’s bra and panties when I was 15 and after nearly getting caught for cumming in her panties, I laid low for a while. That is not to say that I did not creep into her bedroom occasionally and try on her dirties, but I made sure I had all ready jacked off so I would not get caught. Over the next couple of years, I spent a lot of time in front of my mirror tucking my cock between my legs and squeezing my breasts together and the more I looked at my reflection, the hotter I became and the more determined I was that one day I was going to be almost a girl. The thing is, that I really liked playing with my cock so I was not going to have that lopped off. Besides, when I was in the boy’s change room at school, my cock was a lot bigger than their’s were. I will say though, that there were some guys who I would have loved to go over to and start stroking their dicks. The only thing that stopped me was that they would have kicked the shit out of me.
The Shemale Diaries is all about my metamorphisis into a transsexual. It is all about me and everything I went through to become a real live shemale. There are a lot of shemale sex sites out there and all sorts of tranny porn, but this answers the fundamental question that most guys and, even girls, have asked me. How did you become a shemale? What is it like to be a shemale? How hard was it for you to become a shemale? Now the fact that I am a very sexual lady, The Shemale Diaries are going to be loaded with sexual recountings of my very first time that, as a shemale, I got undressed and had sex with a young man who had just picked me up in a bar right through to some of the trials and tribulations of being a shemale. There are some drawbacks, not many mind you, but there are some and because, if this is going to be a real diary, you deserve to hear all about everything in my shemale life. So join me regularly for my updates. I am not a seventeen year old boy any longer. In fact, I am a young woman 28 years old so I have eleven years of great stories and adventures to tell and that will really keep me busy and I hope it keeps you glued to me. Of course, if you are a hot sex guy, I would really love you glued to me. So, tune in regularly and I will take you on the journey that is a shemale’s life. Indeed, it is a journey of my life and that is The Shemale Diaries.