Story Details

From Female to Shemale

SexyShemale on Anal Stories

This all happend the summer when I had my 19th birthday. It started with my boyfriend: -Ooh yeah... You feal tighter every time! -I do? -I'M CUMMING!!! I felt his 5" dick hitting deep in me while cumming. I wasn't very impressed by his preformance. We had been fucking for 4 months, but he still hadn't made me cum. It was frustrating, always having to pull out my dildo after he had left! Anyways... He was lying in my bed next to me, breathing slowly. I asked him if I really was tighter, but he wasn't shure how to respond: -It's probably just me, but you are feeling kinda tighter... This made me ask myself a lot of questions. Wasn't I required to use more lube before using the dildo than earlier? Yes. Hadn't my boyfriends dick felt bigger lately? Yes. Wierd...

Later that week, after another conversation with my boyfriend about me getting thighter, I went to a friend of my father who was working at the hospital. First he did a regular check on me before he asked what that "thing" I had mentioned earlier was. I explained as best as I could without making him (or myself) too uncomfortable. He didn't have an answer or solution, but he gave me a thing that could measure my lenght and width when streched out to the max. He told me to call him if something wasn't as it shoult be. I walked right home and tried it. It was actually making me really hot! Especially the thought about a doctor giving me a free toy! I measured myself after lubing it up, and wrote the numbers on a paper. Now it was just to wait... One week after the first measuring I measured myself again. I slid the wet pole up my pussy, and looked at the numbers on the side. I've never been freaked out as much as right then. The numbers was halfed. My vagina was shrinking! I jumped on the phone and called my doctor, but the receptionist on the other end said that he was away on a one week holiday. I put the phone down and looked at myself. Tears was dripping down from my red eyes. By the time he got back my pretty little pussy would be less than an inch deep. The days that came was just a blur for me. I didn't habe sex, I didn't talk to anybody in person (I lived by my self in a little apartment) and I didn't measure myself again. Not until Saturday evening. It was my birthday, but I hadn't celebrated it in any other way than getting drunk. I looked down on my pussy, and saw that only my outer vaginal lips where left. It wasn't hard to see that I would have as much success putting anything in there, as winning the paralympics. I wasn't frightent, just disguised by myself. I was no longer a woman. After that day I dind't look down there in several days. The only thing on my mind now was to move on without any sexual life. Boy was I wrong!

Three weeks after my pussy dissapeard I dared to look down there again. The sight was definetly not whath I was expecting. Where I thought it would be a flat surface, a penis had emerged. I was so overwelmed by this that I almost fainted. I sat down on my bed and looked at it. I almost felt like I do when I see a newborn baby. It was that feeling of watch something you had created. I slowly stroke the penis and felt it getting hard. I wasn't shure how much to expect. I had seen the penises on shemales before, and they often times never even got hard. But that wasn't a problem I had, thats for sure! My penis was growing and growing and when it stopped, I thought I've never seen a penis this big! I got my ruler from the desk and measured the length. 8.5"! That wasnt just big. That was huge! It was 3,5" longer than my boyfriend's. -This isnt 't happening, I thought to myself. But it certanly was. The next day I was thinking of who I should tell. I had alredy broke up with my boyfriend. I didn't tell him whath happend, only that something happend, and I couldn't see how we could still be together. My first thought was to call my doctor, but he would probably make a big deal out of the whole situation, so I didn't call him. Just when I started thinking again, my dad called. I hesitated for two seconds, but I came to the solution that he would think it's okay. I picked up the phone: -Good morning darling! I'm sorry for not calling you earlier, but I've been... -Dad, I need to see you! Correction: you need to se me! -Is something wrong honey? -I'll be at your house in half an hour! I put the phone down slowly. Suddenly I wasn't so sure about telling him, but there was no way out now. Half an hour later I parked my car outside my dad's house. I was wearing extremely tight leather tights, a top that was one size too small and high heels. And no bra. Why I was wearing this, I don't know. It just felt right. I rang the bell, and ten seconds later my dad stood in the door with a concerned expression on his face. -Is everything all right, dear? he asked me while stepping aside, and letting me in. -No it isn't, and yes it it, I said as I walked into his kitchen. It actually looked nice, considering the absence of women for the past three years. -Dad, I got a penis. The look on my dads face was probably one of the looks you would call priceless, but I wasn't in the right mood. Slowly his face turned a little red as he blushed. -I'm not sure exactly... -DAD, I HAVE A FUCKING PENIS! I screamed before I started to cry. He wrapped his arms around me and whispered: -That's alright, dear. May I see it? I nodded and stood up. I dont't know why I was doing this, but my body reacted by itself. I pulled my tights and panties down. My dad got onto his knees and took a good look at it. -Can I see it erected? he asked. I nodded again and started slowly to stroke it. It went faster this time, and soon it was fully erect. -Oh boy! That's a big one. Just wait right here while daddy goes to get something. I heard his footsteps as he disappeard behind me. At first, nothing of this made sense to me. But suddenly something in my brain said "click", and I was able to think straight again. He was going to fuck me! But it didn't make me angry. Maybe this was what I've always wanted. Maybe this is why I dressed up like this. -No, I whispered to myself. If anyone should get fucked here, is should be him! I heard him come down the stairs now, but I had a plan. -Can I go to the bathroom, daddy? -Yes, of course, dear! I went up the stairs he just went down, and walked slowly into the bathroom. I looked at the sink, and there I saw it! Daddy's viagra! It said only to take a half pill, but I took two. Instantly my dick started to grow. It felt fansastic! I looked around to see if I could measure it before I went down again. I found a wierd looking ruler, but it worked. 10"! That should be enough. I walked down the stairs and into the kitchen. There I saw my dad rubbing his meat slowly with his eyes closed. If I were to guess, he was around 6". I walked over to him, silent as a cat. When I was behind him, I whispered into his ear: -I want to fuck you. He looked up stared right into my eyes. -Shit honey, you scared me! -Just bend over slowly... Of some reason, he did as he were told, but when I opened the bottle of lube he brought down earlier, he spun around. -Please honey. I don't want this! The look on his face made me feel bad. It was pure, uncoverd fear. I slowly put the lube down and turned around. The kitchen table was filled with papers, so I took them away and leaned over it. -Stick it in, daddy. -But, but, but... -Just do it! He didn't hesitate any longer, and slammed it into me. I screamed, but not in pain. I mean, I have tried anal before, but this was completely different. Is was just as tight as before, but not as dry. Somehow it was lubed, just like my pussy would be. And it felt much better than before! Like somone had taken the nerves from my pussy to my ass! My dad was fucking me slowly, but I was tired of hesitating men. -FUCK ME HARDER AND FASTER!!! He stepped the tempo up. I was now breathing heavily as his cock switched between filling me up and barely be inside. I hoped he would go even faster, but didn't dare to say it. I wasn't able to speak, just breathe and screame. As if he read my mind, he went even faster, and yelled: -I'm cumming, honey! I opened my mouth and started to scream, because I was close too. But suddenly he stopped. I felt something deep inside my ass, and guessed it was his cum. He was now sitting in a chair, breathing heavily. I looked at him, but didn't say anything. Instead, I wrote a small message on a piece of paper: -It was good and everything, but I need someone who is willing to both take and give. Besides, your cock is to small, and you didn't make me cum. Goodbye.

The next day I woke up late. I didn'g have much to do until the evening, so I just sat in my bed stroking my dick and thinking of who would be the best sex partner. The answer was of course someone like myself. A shemale. Not a male-in-female-clothes kinda deal, but a woman (or two!) with a dick. I also realized that I hadn't cummed with my cock yet! I wanted it to be as good as possible when it was my first time, so I turned on the TV in front of my bed and layed down, still stroking my dick. After about half an hour of stroking dick while watching the pizza boy fuck two hot teens, I felt something. It was like a volcano ready to erupt. I stroked faster and faster and suddenly it exploded. The sensation was amazing, but the massive amount of cum stunned me. It was much more than I've ever seen in any porn movie. I dried my sheets up and went to sleep again. I just woke up, but after I came, it felt like I had been working out all day. Later that night I decided to go out to find someone to hang out with. I was tired of my old friends, so I was going to a club I've never been to before. Before I left I had to decide which clothes I should use. I chose some black, superthin latex tights that gripped nicely around my legs. Since I didn't have any mens underwhere, I decided to go without anything covering my dick. On the top i chose a matching black latex top and a leather jacket that stopped a few centimetres under my boobs. I locked the front door and walked towards my car, but stopped halfway. Driving my MC would be much more fun! When I arrived at the club, I was stopped by the guard. He asked to check me back at his office. I got the hint and walked behind him around a corner and in a door. When I got in, I stripped my latex pants down and revealed my 10" monster: -Bring it! I said to him. He laid me down with my boobs against his working desk. Then he took his cock (7" I would guess) out and approached my ass. His cock where thicker than my dad's, and felt fantastic when it was pushed up my gloryhole. When he had his whole cock inside, I screamed: -FUCK ME SENSLESS, YOU BASTARD!!! Encoruaged by my screaming he sped up and soon he was pounding me harder than anyone had ever fucked me before. While he was doing this, I was begging, crying, moaning and screaming, but he never got me to orgasm. When he was done he said that I could go right in and enjoy myself, but I had to watch out for any dealers or pimps in there. I walked into the club and was supprised by how dark it was. The first room I got into was just a hallway with two doors in the other end. The one to the left said MALE, and the one to the right said FEMALE. I wasn't sure witch one to take, because none of the said anything about SHEMALE. I opened the FEMALE door first. The room was filled with men watching women dancing on these small stages. I walked over to one of the men who looked like a big badass, and started a convesation. It turned out he was gay, but curios on the female body. I invited him to a private lesson in one of the "private rooms". I knew that they were filled with small cameraes, but I didn't care. When we got in I asked if he did it up the ass, and he said he had tried it a couple of times, but when he saw my monsterous cock he hesitated. I left him there and decided to go into the MALE room.

In the MALE room there were male dancers and female watchers. No other males. I walked to one of the stages, but felt kinda akward, because I had a dick. I felt a hand on my shoulder, and a beautiful girl started talking to me. I couldn't exactly tell what she said because my brain was in slow mode. I had probably just falled in love! -Do you feal alright? You look kinda pale. -I'm fine thanks. Who are you? -Oh, I'm just one of the regulars. I thought I should say hello, 'cause I've never seen you here before. Her lips were moving in a way that mede me want to kiss them and her eyes was making me dizzy. -Are you sure you feel alright? Here, let's find you somewhere to lay down. She took my arm and walked with me into one of the private rooms. There she helped me down on one of the beds. When she let go off me I felt like I was never going to se her again, so I pulled her down on top of me and kissed her passionately. My emotions were running wild as I kissed her, and she started to kiss me back. Soon clothes started flying as we kissed. Finally we were both naked, and the expression on her face told me that 10" of awesome is just what she needed now. I lied down on the bed and she climbed on top of me. At first she was just grinding against it, but then I felt the inside of her pussy on the tip of my cock. She slowly lowered herself down until she was filled completely. She was suprisingly deep, about 9". It would have been perfect if the Viagra wasn't still affecting my cock. She lifted herself up again and repeated it, a little bit faster this time. Soon she was sliding up and down at a moderat, but still perfect, tempo. It was a completely new feeling for me. Instead of the rough pounding up my ass it was a slow, comforting type of sex. More like making love. The thought of anyone cumming didn't reach any of our minds. After about half an hour she stepped the tempo up a bit, clearly wanting a good ending. It was probably just as much in her mind to make me cum, than to make herself cum. Just when I started to wonder what's in her mind, she lifted herself of my cock. She walked slowly over to closet that was hidden behind some curtains, and came back with a scary looking strap-on. It was pretty long, and it was covered with small dots. Besides, when she turned it on, it started spinning around slowly. She put it on, and moaned a bit. Maybe it had a vibrator as well. Then she walked over to me: -You ready? I just nodded. She took my legs over her sholders and  moved the strap-on towards my awaiting gloryhole. But then, she hesitated. She looked at something behind me, and nodded. Two things happend: someone blindfolded me, and my whole body was lifted up by several hands. I started to panick, but calmed down when some familiar lips kissed me softly. Then I was placed in this constuction that heldt me from my arms, legs and lower back. I first wondered if I had become the main item in an orgy, but didn't care. I was open for anything. I felt something touching my ass again. I first guessed it was the tip of the strap-on, but it was warmer and softer. I felt it started to penetrate my ass at the same time as I felt something else touching my cock. It was no doubt that someone slid their ass down on my cock while a cock penetrated my own. When they both had gotten as far as they could, two plastic things forced my tits together. And somehow a person slid his well lubed cock between them, but stopped moving when he was in position. The next thing wasn't any suprise. A cock (the biggest so far) was put in my mouth, and slid as far back as possible without deepthroating me. It may sound strange, but it was very natural. The feeling of beeing filled up had reached my brain, and it felt amazing. Then, like on a signal, everything started to move. The cocks moved in and out in the exact same tempo, and the ass covering my own cock, did as well. This brought me over the top instantly, and in the following I-don't-know-how-long every thrust got faster, stronger and deeper, and every thrust gave me a new orgasm. This went on for a long time, but it seemed like none of them was going to cum. When I thought i couldn't take it anymore, they pulled out. All the cocks and the ass disappeard, and was replaced by emptyness. I felt kinda lonely for a split second, but then I heard the sound of small feet walking over the floor. I couldn't know for sure who it was until he started to lick my ass. It was a dog. A fucking dog! But damn, he could lick. His big, hard, disgusting tounge licked my ass hard, and I loved it! It was so much better than a human tounge. But the joy ended too fast. Or so I thought. Suddenly two big dog paws landed on my tits, and the dog penis rammed and penetrated my alredy overused ass. I could feel a slight difference from a human cock, but it wasn't too different. Exept the speed! The dog was blazing in and out like no tomorrow. I started to scream in joy (I had always been quite a screamer), and no cock stuffed my mouth this time. In fact, between my screams I could hear heavy breathing from many mouths, but not the typical manly breathing. Could it really be? But I didn't get the time to think it throug, because the dog cummed in my ass, meanwhile a lot of human cocks shot their massive loads all over my tits and face. After the last drops of cum had landed on me and the dog had been taken away, my blindfold was taken off. My suspections where right. It wasn't a group of horny men that had been fucking me, it was shemales. Now, they were standing around me with their cocks in their hands. None of them where anything but rock hard and ready for more. I had a feeling that this would be a long night.

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