My transition from David to Jessica

I knew I was a girl, even if my body had boy parts.

As far back as I could remember, I knew that I was a girl who was born with a boy’s body, and named David. Whenever I would start to play with my sister’s toys or try on Mommy’s clothes, Dad would get mad and make me do boy things and play with boy toys like trucks and toy soldiers. They did let me grow my hair long because a lot of guys had long hair. In my mid teens, I was petite. I was 5’6” and weighed 122 pounds. I did not work out or eat very much. I wanted to keep my body thin and soft. It felt natural.

It got to the point in junior high that I saved my allowance so I could go to the thrift store and buy a couple skirts and blouses and a pair of pretty sandals with 2 inch heels. I snuck a pair of Mom’s panties and one of her bras. I kept my pretty things hidden in a box in my closet, under a bunch of other things. I would put them on when I was alone in my room. It felt so good and so natural. I felt pretty.

Eventually I got to where I would keep my girl clothes in the tree house we had, out back in the woods. I would go to the tree house and change into them and then walk around in public. I had to put padding in the bra to have any shape at all.

I had fucked one girl. She was pretty much considered the class slut and would let just about any guy in her pants. When I removed my pants, she made fun of my small cock. It was about 5 inches when hard, and not very thick. She just laid there and let me do it, without much reaction. I lasted maybe 2 minutes at most before pouring my seed into the condom. It didn’t do much for me, and even less than that for her. I spent the whole time wishing I were her. When I was finished, she got up, pulled her panties back up and told me not to ask again.

One day when I was a senior, an older man stopped me and told me how pretty I looked in my skirt and blouse, with my hair in twin ponytails. That was a quick way to make my hair look more feminine and still be easy to put back when I would go home. He said that I made a very attractive girl. I told him that I was a girl, but my body got messed up. He asked me my name, and I told him Jessica. That was the name I gave myself. Then he bluntly asked me if I would suck his cock. I had never done that, but had watched hundreds of videos, on my computer, of girls being fucked and giving blowjobs, also of transvestites and guys who liked having sex with other guys. I liked the ones of trans guys sucking and getting their assholes fucked the best. I looked at him and said, “Not yet.” He asked me if I wanted to try it, and I nodded my head yes.

I followed him to his car, and we got in the back seat. He lifted his ass off the seat and pulled his pants and shorts down. His hard six inch cock was pointing straight up. “Go ahead and show me that you know what to do.” I reached my hand out and took hold of his cock. A feeling of excitement raced thru my body and mind as, for the first time, I touched a cock other than mine, I stroked him a couple times and pre-cum oozed out and dripped onto my hand. I lifted my hand to my face and licked his pre-cum. It was thin, clear and tasteless. I knew it would be, because I had tasted mine and it was the same.

He put his hand behind my head and pulled it to his crotch. My face was just a few inches from another man’s cock. I thought it looked wonderful. “Open your mouth and put it in. Suck my cock. Fuck my cock with your face.” I opened my mouth and leaned forward. My lips slid down over his cockhead and down his shaft. I was feeling very, very feminine and happy. I knew that this was just what I was born to do.

The head and outer skin was warm and soft, the inner shaft was rock hard. I knew it would be, as mine was like that when I had an erection. Fuck, I wished I had a cunt rather than a cock. With his hand pressing on the back of my head, I went deeper and deeper. I had his cockhead and about half of his shaft in my mouth and was happily bobbing up and down on it, but he wanted more. He pushed harder on the back of my head. His cock hit the back of my mouth and I gagged. He laughed and let me pull back, just a little bit.

He took his hand away and I kept giving him a blowjob, like I had seen in so many videos. I was enjoying it. He lasted about 5 minutes. My jaw was starting to ache. I felt that I had gotten hard. I didn’t like that. I’m a girl. I’m not supposed to have a cock that gets sexually excited. I’m supposed to have three holes that men want to fuck. He announced, “I’m going to come. Keep my cum in your mouth and show it to me, until I tell you to swallow it.”

He pulled back till just a little more than just his cockhead was between my lips. He grabbed his cock and rapidly stroked it. He groaned, “Here it comes. Don’t swallow it.” I felt his cock swell and pulse three times. Each time, a big squirt of cum flew into my mouth with surprising force. It was thick and slippery and warm. It had a salty and slightly sharp taste. I fought the urge to swallow. There was more than my mouth could hold, and some leaked out around his shrinking dick and dripped down onto my chin. He pulled away, Open your mouth and show it to me.” I did. He grabbed his phone and quickly took a picture of me with a mouthful of his white cum. “I’ll send you a copy to remember your first time. OK, now swallow it and lick my cock clean.” I gladly did. I had just given my first blowjob and swallowed my first load of a man’s cum. I was so happy. I knew for sure that it would be far from the last time I did it.

He pulled out his wallet and handed me a twenty. “Here, buy yourself something. I’ve got another twenty if I can fuck your ass.” I thought for a minute, then replied, “I’m only an anal virgin once, my ass has to be worth more than that, the first time.”

“How much?”

“$200 and you can fuck it as much as you want, till you can’t get it up any more.”

After a minute of thought, he said, “OK, but not now. I’ll pick you up tomorrow and we can go to my place. Meet me right here at 2pm.” I got out of the car and he drove off. I went to the thrift store and bought a shorter skirt and a sexier blouse. I went to Target and bought some high cut lace panties.

The next morning, I took a long bubble bath. I also pulled Mom’s dousche bag out of the linen cabinet and used it to give my bowels a good cleaning. Mom and Dad were both at work, so I got dressed at home. I put on some of Mom’s makeup and did my hair. I looked in the mirror. I thought I looked sexy. It would have been so much better if I had real tits and a cunt, rather than this damned cock. About the last thing I did was to push some vaseline into my butt.

I got there ten minutes early and he was already there. From the inside, he opened the passenger’s side door and I got in. We drove about fifteen minutes and pulled into an upscale, gated apartment complex. We pulled into his garage and entered his apartment. It was really nice, with what looked like expensive furniture and decorations. He went to the kitchen and got us beers. He finally told me that his name was Steve. He asked me for my email address. When I told him what it was, he sent me the photo that he had taken at our first meeting, the previous day. I opened it on my phone and saw myself with my mouth open and overflowing with Steve’s thick white cum. I smiled and put my phone back in my bag, along with my blue jeans and sweatshirt. I would put them on before going home, if it was late enough for either of my parents to be home.

Steve took my hand and led me to his bedroom. He watched me as I undressed and then he had me undress him, and kiss all over his body as I uncovered it. We got onto his king sized bed. He lay on his back. “Suck my cock till you get me hard. Take it as deep as you can and suck hard on it. Don’t use your hands.” I quickly took his limp dick in my mouth.

I was surprised at how long it took me to get him hard, but he told me I was doing a good job and that it felt good. I didn’t know it, but he had already masturbated, so he would last longer. “Suck my balls and lick up and down my shaft.” After about five minutes, I felt him harden in my mouth. He put me on my knees and elbows and got behind me. He spread my legs wide apart. My cock and balls dangled below me. I knew the time had come. He spit into his hand and rubbed his spit around the head of his cock.

I felt the tip of his prick press against my puckered little anus. He held my hips and pushed. He slid in more easily than either of us expected. I had expected it to hurt. I did not tell him that I had lubed myself. Very quickly he was balls deep in me. And he started fucking me, hard and deep. “Your ass is so nice and tight.” It felt like I had to shit out the biggest turd of my life. The longer he fucked my butt, the harder he fucked it. I felt his balls slapping against my balls. Because he had already drained his balls before he picked me up, he lasted and lasted and lasted. The longer he butt fucked me, the more I liked it. The feeling of having to shit went away and was replaces with pure pleasure. My cock hardened, and then I screamed out in pleasure as I orgasmed and my cock sprayed cum on his bed. I hadn’t expected that to happen. After several minutes more, I felt him hold deep in me and I felt my insides being flooded. He rolled on his back. “Suck my cock. Clean me all up.” Sucking a cock that had just come out of my ass did not sound desirable, but I knew I was clean in there, so I did it. I had seen ass to mouth many times in videos. I sucked him till he was completely limp. He told me it would be quite a while before he could get it up again. We sat and chatted for a while. I told him how much I wished I had a real female body, and how I hated it when I got an erection. He took me close to my home. My parents would not be home yet, so I did not change clothes. I cleaned up and changed before they got home. I had $200 to spend.

The next morning, there was a cum puddle in my bed. My ass had still leaked more of Steve’s cum as I slept. After Mom and Dad left, I went to wash my bedding. When I took the sheet off, I brought it to my face and licked the cum spot, as I thought about the previous day.

Three days later, Steve messaged me and said that he had told a friend about his time with me. He asked me to come over and spend some time with both of them. “I’ll give you $100 to spend the afternoon with us.” I had gathered from his car and his house, that money was not much of a problem for him, so I agreed to take his money. I probably would have done it for free, if he had not offered.

He picked me up ay the usual spot. When we walked into the apartment, his friend was sitting on the couch, naked and stroking a much bigger cock as he watched porn on the TV. “Jessica, this is my friend Ron. Go over and say hi to him.” He stood up. He was probably in his mid twenties. He was about six-two and maybe 200 pounds. He was built spectacularly, with muscles in all the places a man should have muscles. One other thing I immediately noticed was that he was black. His skin was the color of fine dark chocolate. He smiled at me, put his hands on my shoulders and pushed me to my knees. “Say hello to my cock.” I knew what he wanted. His manhood was big, but not as big as some I had seen on the videos I had watched. I reached out and put one hand around his already hard cock. I couldn’t reach all the way around it. I stroked it and then put my second hand around it. The head still stuck out past my hands. I licked a drop of pre-cum off the tip. “Suck it.” His voice was deep and almost threatening. I took my hands away. I had to open my mouth as wide as I could, but I got him in. I started sliding my lips up and down on his cock. “Play with my balls.” His cock was oversized and so were his balls. I saw that Steve had his phone out and was taking a video. I was thinking to myself. “Am I going to be able to take his big cock in my ass?”

After a minute, he pushed me back. I sat hard on my ass. He took my hand and helped me up. Then he reached down and gave my cock and balls a hard squeeze, causing me to yelp. He laughed and told Steve, “Willing little sissies are fun.” I looked over and saw that, without stopping the video, Steve had stripped. He stood there, looking small compared to Ron, and looking out of shape with his chubby, middle-aged tummy. His six inches looked small next to Ron’s cock that probably was around nine inches. I imagined how my dick would look put next to Ron’s.

Ron put his arm around my shoulder and guided me to Steve’s bed. They got on and watched me undress. Ron said, “I can see why he wants to be a girl. That little weenie isn’t good for anything.”

We spent more than an hour with me sucking them and them fucking my ass. Steve fucked my ass first, while I sucked all of Ron’s manhood that I could get in my mouth. I was glad that they did it in that order. When Ron pushed into my ass, it did hurt, but the pain quickly went away. I couldn’t believe that I could take all of him in my ass, but I could. They both came in both my ass and down my throat. My dick betrayed me again and sprayed my cum on Steve’s bed. Finally they were done with me, and I gave them each a final cleaning with my mouth. I was worn out but happy. Before he took me home, he handed me $100 and a gift wrapped box. It was long and skinny. I opened it and it was a soft plastic dildo, about the thickness of Steve’s cock, but at least ten inches long. “Practice with this till you can take it down your throat without gagging.”

I watched videos and read suggestions about how to do deepthroat. Things like how to breathe, relaxing your throat, putting butter on the roof of your mouth and the angle to hold your head for a straight shot. Each day I tried multiple times, finally on afternoon of the fourth day, it slipped into my throat without gagging me. Once I figured it out, it became easier and easier. I was anxious to show Steve.

About a week later, Steve messaged me and wanted me to come over. He had something he wanted to talk to me about. “I know that you are not happy living with your family. You are old enough to move out. How would you like to come live with me, at least for a while? You would not have to ever wear guy clothes again. I’ll buy you some very pretty things. Also, I have a doctor friend that I talked to about you. He said he is willing to help you transition.” I smiled and kissed him. He wasn’t really fond of me kissing him. I opened his pants and took him out. I went down on him and showed him what I could now do. He rested one hand on my throat so he could feel his cock moving inside my throat.

I told my family that I was moving out on my own and sharing a place with a friend, but I did not give them the details. The next day I packed two suitcases and a backpack. I had everything I wanted to keep. My sister was excited. She quickly claimed my room because it was larger. I said my goodbyes and promised to keep in touch. I could see a tear in Mom’s eyes. Then I was gone. Steve was waiting for me out at the curb.

Steve’s apartment was three bedrooms and a large family room and nice kitchen. One of the bedrooms was set up as an office that allowed him to work from home, and one was a guestroom. As I expected, I shared Steve’s bed. Steve took me shopping and we bought lots of very pretty and sexy looking things. He took me to a salon and I had my hair curled and shaped. Some of the people gave me strange looks. We also got some nice makeup. All my guy things were locked away in storage or disposed of.

Over the next week, he fucked me and I deepthroated him morning and night, and sometimes a random times during the day. Steve did not seem very affectionate. I got a feeling that I was only a fuck toy for him. Then he said that he had arranged a welcoming party for me. That night, four men and a woman arrived. Ron was one of them. I was even able to take him down my throat, but it was not easy. The woman and I sucked all the guys and they all fucked us. About one am, Steve said that the party was ending, but there was one final closing event. Steve had me lay on the floor on my back. Then the woman squatted over me and lowered her cunt onto my face. She had four loads of cum inside her, and I had to eat her out until she orgasmed and no more cum flowed into my mouth. That meant that I had swallowed about eight loads of man sauce that night. My stomach felt full.

He took me to see his doctor friend. We talked for about thirty minutes about what could be done. Medicines, castration, breast implants and even removing my penis and construction of a realistic looking pubic vaginal area. To do it all would take a long time and be very expensive. He said Steve had agreed to pay for all but the penis removal and reconstruction. He did say that it was possible to shorten it so there was just enough to urinate with, but I would not look male in my underwear. Rubbing it like a clit would still give me the feeling of an orgasm but there would not be any cum. He said that if I ever wanted, I could have an operation on my vocal cords to raise the pitch of my voice. I said I was ready for castration and implants.

“I want to examine you to make sure everything is OK for you to go thru all of this.” I went into the exam room and changed into a gown. He came into the room and had me sit on the exam table. He lifted the gown and felt all around my parts. I started to harden. “The castration and medicines will stop that. Your penis will stay limp and actually shrink some. I need to check your anal cavity to be sure there is no problem there. Stand on the floor, spread your legs and bend down onto the table. I watched him put on latex gloves and apply some lube.

He slid one finger up into me and then added a second. “I need to check even deeper.” I heard him unzip his pants. Then I felt his cock press against my rectum. He fucked my ass deep and hard and came in me. He handed me a tissue and told me that everything appeared good. I left with three prescriptions and an appointment at the hospital a week later. We had decided to do the castration and implants during the same hospital stay. I started taking the pills that night.

After two days in the hospital, I returned home with bandages below my cock. My balls and scrotum had been removed and firm B-cup, almost C-cup, tits that were there but all bruised. That very night, Steve insisted on a blowjob.

Two weeks later, the bruising was about gone and I was able to stop having bandages where my balls had been. My cock was totally limp and less than three inches. All it worked for was when I held in between my fingers to pee. Steve said I looked great. Steve was regularly fucking my ass again.

Twice while I was recovering, Steve brought a woman home and fucked her in front of me. Then he had me eat her out before she left.

Steve took me shopping again. This time the skirts and dresses were even shorter and the tops were low cut to show a lot of my new breasts. He did not buy any panties. After a month, I was all healed. I liked how I looked but still hoped that someday I could completely get rid of my cock.

I went home, dressed in one of my sexiest dresses that had a neckline almost to my waist, and wearing three inch red pumps. My hair was freshly fixed and I had applied my makeup. I knocked on the door and Mom opened it. “Yes, may I help you?”

“Mom, it’s me, Jessica, I mean David.”

I thought Mom was going to pass out. “Oh my God.” I walked in. Mom, Dad and my sister just stared at me. Sis spoke first. “Do you still have a …… “? I was commando, so I lifted my short skirt and showed them what was left of my male parts. Dad got up and stormed out of the room. Mom, Sis and I chatted for about twenty minutes. I told them about my new life without going into too much detail about the sex. As I was leaving, Mom said, “I love you …… Jessica.”

Steve arranged another party. He called it my coming out party. It lasted till early in the morning and I was the hit of the party.
____________________________________________________

0625. PO469. If you want to see a full list of my other stories, click on my username link at the top of this story. Any photos with my stories are of people who are 18 or older. They were consensually taken and come from my friends or from a website that states that its purpose is sharing adult photos and gifs. Photo credit and thanks to imagefap.com. If you claim copyright to any of these, and want it removed or credited, let me know.