Jess

I first met JD in the 6th grade at Westminster Middle school. We had several classes together and after being paired up repeatedly for science projects and other activities, we became good friends. Our days at school often extended to doing stuff together after school and on the weekends and eventually even the occasional vacation together. JD and I became inseparable. I was an only child while he was the youngest of five and the only boy of the lot.

JD was always a bit different. When we were younger, the differences were subtle. As we got into high school, those differences seemed more significant. JD was attractive - more pretty than handsome - but he never dated. While all the other guys got taller, bigger and stronger, he didn't. He was in good shape - we both ran cross country - but he was relatively short at 5 foot 6 and no more than 130 pounds soaking wet. Everyone at school figured he was gay and hadn't come out of the closet yet.

As you can imagine, some of the jerks at school constantly mocked and bullied JD and I often found myself in fights because of it. I took a few beatings to protect him during our four years of high school. What I didn't realize was that the emotional abuse he was getting at home was far worse.

By the time we got to our senior year, JD seemed distant and isolated. We were still friends and spoke all the time, but even I had a hard time getting through to him. He was barely passing his classes and just seemed eager to be done with school. Towards the end of our senior year he talked about moving out as soon as he turned 18 and he never wavered from it. As our high school years came to a close, I would finally find out why.

I turned 18 in March while JD was a couple months behind me. When his 18th birthday hit in May, he arrived at my parent's door steps with two packed bags. He told us that his father had kicked him out and he had nowhere else to go. My parents loved JD and they gladly took him in.

Just a few weeks later, we both graduated. I had been dual enrolled for several years and by the time I finished high school, I had already earned enough credits for my associates degree. I was ready to get into the workforce and take care of myself. JD wasn't sure what he was going to do.

By the middle of the summer, I had lined up a job as a junior level programmer working on apps for smartphones with a local tech company. By early fall, I decided to move out and live on my own. I found a nice two bedroom apartment close to my work office and in walking distance of the local nightlife. Without hesitation, I asked JD to move in with me. He was thrilled when I asked and immediately said he would.

Our move into the apartment ended up being a turning point in so many ways.

Revealing the truth

Moving into the apartment was a dream come true. My parents were really supportive and surprised us with living room furniture, including a nice, new 50 inch flat screen tv. They also made sure JD and I had suitable furniture for our bedrooms.

It wasn't more than a day or two after we got settled in that JD decided to open up about everything that had happened that year and before.

"David, do you have time to talk," I remember him asking in a subdued tone.

"Sure. I have to run some errands, but I can do those later," I responded.

"I need to tell you about what happened with my parents. About what happened with me. About me. There's so much I haven't told you and I'm sorry I've taken this long to open up about it," he said as tears began to fill his eyes.

I had never seen him this broken before. He could barely control himself. I walked over and gave him a long hug and walked him over to the couch. I could tell this conversation wasn't a standing one.

"My dad always wanted a boy. After four girls, he was excited to have a son he could watch sports with and toss the ball with. Except, that's not who I was. It's not who I am."

He paused for a while to gather himself before continuing through repressed tears, "I just ended up being a massive disappointment to him."

"Are you telling me you're gay?" I asked.

"Not, not exactly," he hesitated.

I was confused and the look on my face must have said it all.

"I'm sorry I didn't tell you this sooner, but I'm actually ... I know that I'm really a girl. I'm trans and I've known it for a while now," he said, quietly. "I began the process over a year ago. My mom supported me and took me to counseling, but hid it from my dad. I was about to start on hormones when he found out and he flipped out. He was so furious. That's why I wanted to get out of the house as soon as I turned 18. He even talked about divorcing my mom, but I don't think he's going to go through with it."

I was floored. I didn't know what to say and sat there in silence. After an awkward minute, JD continued.

"I'm really sorry, David. I wanted to tell you, but I was so confused and upset and didn't want to run the risk of losing my closest friend. Please tell me what you're thinking," he asked nervously.

"I'm glad you told me. Don't worry, this doesn't change anything except that I can be here to help you through all of this," I responded in an assuring tone.

JD smiled and covered his mouth as the tears started rolling down his cheeks. After he composed himself, he made one more request.

"If you don't mind, can you call me Jessica from now on? I want to put the past behind me and I'm getting my name legally changed soon."

"Absolutely, Jessica," I responded affirmatively.

She got up from her place on the couch and sat next to me and gave me a long hug that expressed her relief. I could tell this was a turning point for her and I was determined to help see her through it all.

"My mom has been secretly stashing money away for awhile and she gave me enough so that I can begin HRT. I don't know how it's going to go, so please be patient with me. This is all so exciting and scary and I could be emotional for a while," Jessica said.

"It's fine. We'll work through it. I'm here for you, Jess," I said, apparently giving her a nickname inadvertently. After a pause, I asked, "I hope I'm not prying too much, but are you planning to uh ... you know ... uh, get the final surgery at some point?"

I've since learned how offensive that question can be, but Jess didn't make a big deal of it. She answered, "No. I don't think I will. It's not something I think is absolutely necessary for me. I know it might ultimately limit my dating options, but I'm ok with that. I haven't really thought that far ahead, honestly."

Our conversation continued for a few hours. Jess told me about her hopes and dreams. She said her body would change a lot over the next couple of years. She wanted big natural breasts, but the doctor said most trans women only end up with A or B cups. Her genetics could help, though, as all the women in her family were quite large chested - especially her four sisters. Jess was determined to have them, though, and so she set out to try every possible remedy, diet recommendation and alternate method to promote growth. Her doctor also prescribed progesterone, which he thought would help as well.

She explained that she had started growing out her hair well over a year ago. As it got longer, her natural curls began to show up even more. I had never noticed before, but her curly, brown hair and crystal blue eyes made her adorable already. I had no problem seeing her as Jessica, even though I had known her as JD for all these years.

Towards the end of our conversation, Jess decided now was also the time to start presenting as female. The move into our apartment was her opportunity to truly begin a new life. She had just gotten a job doing audio transcriptions, which allowed her to work out of the apartment.

"Why don't you go with me on my errand run and I can help you kick start your wardrobe? I'll be the first person to take Jessica out clothes shopping," I said excitedly.

The huge smile on her face said it all.

"Are you sure? You don't have to do that, David," she replied.

"I want to. Let's do it," I responded. I got up from the couch, grabbed her hand to help her up and motioned to the door before adding, "This will be fun!"

We finished the day running a few errands and spending a couple of hours buying her some outfits. In total, I probably spent a few hundred on clothes, shoes and makeup. The joy on her face made it all totally worth it.

Changes

As soon as Jess started HRT, the changes began quickly. Within the first few days alone, she had significant soreness in her breasts. She also spent at least 30 to 60 minutes a day massaging them with oil after reading that it could promote tissue growth and lead to a fuller, more feminine shape.

"My boobs hurt so much, David, ughhhhh," she lamented to me after just a few weeks on HRT.

I smiled and gently patted her shoulders before saying, "Just remember, this pain is a good sign. It means they're growing like you wanted."

She hugged me and pressed her head against my chest before saying, "I know. I just wish two big melons would magically appear overnight. Like some Harry Potter shit, you know?"

I laughed and said, "I don't remember Harry having big boobs, Jess."

She surprised me when she suddenly took a step back and lifted up her shirt, revealing her developing breasts to me.

"Do they look like they've grown to you? Can you tell a difference?" she asked me.

I definitely could. Her nipples were larger and puffy and there was definitely more flesh than before. In fact, I could tell that her overall appearance was changing significantly. Her skin looked softer and her overall body shape appeared to be feminizing. Her voice was already a good bit different. Her face, though, was already there. She was already pretty before HRT, but with makeup and the hormones she was gorgeous, and I told her so.

After several months, her transformation was well underway. By this point, she was already into a 34B bra and still growing. Her body shape was far more feminine and her voice was smoky and far different than before she started on hormones. In fact, on several occasions I found myself staring at her longer than a friend reasonably should.

About eight months in, though, Jess truly shocked me. I was coming home from a late day at work. When I opened the front door, Jess was on the couch watching Netflix completely topless! She was massaging her breasts with oil and seemed completely unfazed when I walked in.

"Oh, you're home! Look at this, David! I'm in a C cup now! I'm so excited," she exclaimed as I shut the door behind me.

I looked down at her oil glistened chest and marveled at the significant growth. Her boobs had grown a lot in that relatively short period of time. They were perky and tear-drop shaped and feminine looking. She grabbed them in her hands and jiggled them and poked them around, which was far more of a turn on than I let on.

"I think all the massaging has really made a difference. I bought my first C cup bra today. I think they're still growing, too!" she said gleefully before asking, "Well, what do you think?"

"That's amazing, Jess, I'm so happy for you. They look fantastic," I said awkwardly.

She grabbed her long sleep shirt on the couch and tossed it on before giving me a warm, long hug.

"I wouldn't be here if it wasn't for you, I hope you know that," she said sweetly and softly.

I didn't say anything, instead hugging her a little tighter to acknowledge her words.

I still remember the dreams I had that night. They were vivid and felt like a different reality. Jess was naked, in my arms. My hands were on her breasts, massaging them. My lips wrapped around her large nipples as she moaned in pleasure. I squeezed and kissed them passionately as she writhed sexually under my hands. When I awoke, I realized I had pitched a tent in my boxers.

It was the first of many dreams about Jess in the coming months.

Seeing more of Jess

Over the next six months, I watched as Jess continued to come to life. Her confidence and happiness were so evident now. It was like watching the birth of a new person. In many ways, I felt like I was getting to know her for the first time. The person I used to know was hiding and afraid. This person was vibrant and spunky. Jess truly was a new and different person to me.

In a little over a year, the physical transformation was also incredible. Her body looked completely feminine and her breast growth was beyond her wildest hopes. Our friendship grew stronger by the day as I constantly encouraged and supported her.

One day though, our relationship took a turn I wasn't expecting.

Upon coming home from work one day, I saw Jess wearing really short shorts and using a strange looking device on her legs. When she heard me come in, she jumped up from the couch and gave me a hug.

"You can't look while I'm using the thingy. The light can hurt your eyes if you aren't wearing glasses, David," she warned me as she returned to the couch.

"Is that one of those laser hair removal devices?" I asked her.

"It sure is. It's one of the expensive ones. I've been saving up for it and it came today. I'm going to have a super smooth, hairless body when this is all said and done! The hormones have made body hair less of an issue, but I want every remnant gone forever," she told me.

She continued, "Actually, on that note, I need to ask you a big favor. Like, it's ok if you say no because I'll totally understand. Don't feel like you're going to offend me..."

"Jess, just ask," I said, cutting her off before she rambled on.

"Ok. So, the thing is, I can get to most parts of my body with this thing. Most. Not all. There are some areas I'm going to need some help with if you're willing to help me. Again, no problem at all if you aren't comfortable with it, I can always go to a specialist for those areas," she rambled on.

Wow. Was she seriously asking me to use that device on her backside and what not? I was floored. I didn't immediately know how to respond.

She must have read my silence as my answer.

"Don't worry about it, David. It's ok. I don't want to make things awkward..."

"You didn't. It's ok, I'll do it," I finally shot back.

"Really? I'm serious, it's not a big deal if ..." she started saying.

"I'll do it, Jess. I'd do almost anything for you, including that," I responded before asking, "When did you want to start?"

"Can we do it this weekend?"

"Sure thing," I told her.

That weekend ended up being far more significant than I could have imagined. When the weekend rolled around, I was incredibly nervous. She called me into her room after she got ready. When I walked in, she was lying face down on her bed completely naked.

"So, the trick with the private areas is to use ultrasound gel. I have some on the dresser next to the device. Just rub it all over my backside and just begin shooting like I showed you the other day," she instructed me.

I looked at her naked body and couldn't help but be aroused. Her breasts were poking out slightly at the sides and she had a firm, nearly perfect bubble butt. I grabbed the gel and the device and positioned myself on the bed.

"Uh, you'll need to spread your legs some," I told her.

When she did, I could see as much of her as I had ever seen. Her girl cock was showing a little and I found myself incredibly turned on by it. My heart started racing as my own cock began to harden at the sight of her. This was not a reaction I was expecting to have.

I did my best to act normal - none of this was normal - and began spreading the gel. After a while, the clinical nature of what I was doing calmed me down and I proceeded to get the job done. After about 15 minutes, the session was over.

"All done?" she asked.

"Yup. I think so," I responded.

Unexpectedly, Jess turned to face me, exposing nearly all of herself to me. I tried not to react, but the image of her body facing me was burned into my mind. Her breasts were even larger than the last time she showed them to me. It looked like her genetics did come into play after all! Her girl cock was also there for me to see. She was actually bigger than I thought she'd be, but her cock looked amazingly feminine just like the rest of her.

"So, we probably need to do it a few more times before it's all done if you're ok with that," she said to me, completely comfortable with her body being fully exposed to me.

"Yeah, sure, whatever you need Jess," I responded in a nervous tone.

"Oh! I meant to tell you the other day, but my boobs are officially 36DD now! I can't believe it! My doctor said I'm one of the very few trans girls who will ever experience this kind of growth. I feel so lucky and fortunate. He figures the massages and progesterone made a difference, but it's hard to say for sure. Anyways, don't they look amazing! I'm so excited!" she said gleefully as she playfully jiggled them in front of me.

The sight of her playing with her large, beautiful breasts replayed in slow-motion in my mind. I somehow recovered from the sudden blood loss in my brain to formulate a response.

"Yeah, they're fantastic. I'm really happy for you," I responded dryly.

Something in my face must have disclosed how uncomfortable I was, as she suddenly clued in.

"Oh David, I'm so, so sorry. I'm just so comfortable around you and after what you just did for me, I figured you seeing me naked wouldn't be a big deal. I didn't mean to offend you or anything," she apologized profusely.

"Jess, it's fine. I was just a bit caught off-guard. Plus, I've never seen you quite like this before. It's fine, really," I said, waving my hands in the air to dismiss the apology.

"Ok. Don't worry, I'm not going to suddenly just walk around the apartment naked all the time," she said, as she got up from the bed and walked into the bathroom.

"Well thank god for that," I shot back playfully.

Dammit.

"Thanks again, David. You don't know how much it means to me to have your help and support. You're my everything," she said as she turned on the shower and shut the door.

I walked into the living room and plopped down on the couch to watch some TV. I don't remember what I watched because all I could think about was Jess and her incredible body. I could see the full picture vividly in my mind and my cock got rock hard thinking about it. That night, all I could see was Jess when I closed my eyes. When I did fall asleep, she tore through my dreams like a tornado.

Dating

Over time, Jess decided it was time for her to try dating for the first time. She had befriended a group of other trans women through an online support group and they all decided to get together one evening for a night on the town. I wanted her to get out and socialize since she missed out on it while we were in high school.

As for me, I always had excuses for not dating much. I was really wrapped up in my job or I was too busy with other commitments. The reality was that much of my life was spent at the apartment with Jess over the past 18 to 24 months. I had gone out a few times and Jess always encouraged me to do so, but nothing ever stuck. I always found myself wanting to spend more time with Jess than with any of the girls I had taken out.

Jess began regularly going out with the girls. They would often come back to the apartment afterwards complaining about how hard it is to find a good guy these days. She and the girls still had fun going out, but they regularly struck out in trying to find guys. Nevertheless they persisted.

On one fateful evening, though, the return visit to the apartment would turn out to be quite different. Shortly before midnight, the door flung open and Josie - one of the new girls Jess was hanging out with - started screaming my name.