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My Unwanted Transition 8

( Disappointment )

I stepped up to the apartment door, knowing that Andy was inside. I hadn’t responded to his texts, so I was sure he wanted to know how I felt about it. With a deep breath, I opened the door and went in. I went to my room first so I could change into fresh clothes. Next, I went to find something to eat since I skipped breakfast at Skylar’s place.

I sat down at the table and ate some cereal while waiting for Andy to come out, which didn’t take long. He came out of his room, sat at the table with me, just looking at me without saying anything for a minute.

“I guess you didn’t like my text,” he said finally.

“Why do you want to suddenly date me?” I asked, wondering why he didn’t ask me sooner.

“I don’t know,” he said. “We’ve been friends for a long time, and course, you used to be a guy, so I never thought we’d date. But, after what I said about moving into your house, I thought about it- and, well, we’ve had sex and just the other day, great sex. We already live together, we know each other well, and like a lot of the same things.

“Why couldn’t you have asked me before?” I said, becoming upset.

“What’s wrong?” Andy asked.

“I spent all day with Skylar yesterday,” I answered. “And all night.”

“Oh,” he responded.

“Oh? Just oh?” I said, my emotions flooding into my voice. “We fucked! And I told him I’d be his girlfriend. Only because I thought you weren’t interested!” My voice started to shake, and tears were welling up in my eyes.

“I’m sorry, Jen. I never thought you’d want to date a guy, so it’s something I didn’t want to bring up and make you uncomfortable,” he answered, trying to explain. “And I thought the sex was just because it was easy, with no strings attached and felt good.”

“That’s what it was supposed to be,” I said, wiping the tears from my eyes. “I can barely remember what it was like to be a guy. Any of it. I don’t remember the sexual urge of a guy, the attraction to women, anything. Every day I wake up, more of that part of me has faded away, replaced by a piece of my new life. I want to hate it, but I don’t.”

“I didn’t know, Jen,” he said. “And I definitely didn’t mean to hurt you. I just wish you would’ve told me all of these things- how you felt.”

“I didn’t even know how to tell myself,” I said, then getting a tissue to wipe my eyes. “Andy, I like being this way. I love being a woman, and it makes me happy that you accepted me so quickly.”

“Of course, I did! Just because you had to transition from a guy to a girl doesn’t mean you aren’t the same person. Even if you like being a girl, you still haven’t changed all that much. You still enjoy video games, movies, porn, all of that.”

I listened to what Andy was saying, and I appreciated every bit of it. Even with me trying to blame him, and the fact that I went and had sex with Skylar, he still sat right here and supported me. I got up and walked around the table to where Andy was sitting. Without saying anything, I turned and sat sideways on his lap, then wrapped my arms around him while placing my head on his chest. He put his arms around me as well, and we sat there in silence for a long time until I calmed down.

“I don’t know what to do. I don’t want to hurt you or Skylar,” I said softly.

“I can’t make that choice for you, but if you do pick him, I promise we’ll still be friends like always,” Andy said.

“Thank you,” I said.

I spent most of the rest of the day in my room just thinking about what I was going to do. My parents were going to move soon, and I was going to have an entire house to myself. I’m sure by now, Skylar had told all of his friends that we were dating, and I didn’t want to hurt him by breaking up. But, if Andy was ready to be with me, that’s what I really wanted to do. More importantly, my final interview was coming. I cleared my mind of everything else for now and picked an outfit for the interview, wanting to make sure everything was perfect.

There was so much going on in my head that I could barely relax or sleep. I got out of bed incredibly early, and since I couldn’t sleep, I shaved, took a long hot shower, and got my hair ready. I noticed my bra was getting a little tight again, which meant my breasts were still growing. That would be an issue for a different day, though, so I focused on today. I did my makeup and put on lipstick, then dressed in the clothes that I had picked out, which consisted of a blouse, skirt, heels, and stockings.

Instead of getting a ride from Andy, I decided to take a rideshare to the office. It gave me time to think on the way there without having to talk. When I arrived at the office, I signed in, then went to the bathroom to check myself while I waited for my turn. I straightened out my clothes and checked my makeup before going back to wait. Not long after, the district manager called me into his office. I followed him in and took a seat at his request.

“Thank you for coming, Jenny,” he said.

“Thank you for this opportunity,” I responded with a smile, trying to remember to sit up straight and keeping my legs closed.

“I’ll get right to it then. I’ve reviewed your training and see here that you’ve done quite well, even working extra hours to complete it on time,” he said.

“Yes. I’m willing to do whatever is needed,” I said, trying to sound confident.

“I like that spirit,” he said, then sighed after a moment. “This is a tough round of candidates. Ten altogether, but only two positions available.”

“I assure you that you won’t be disappointed if you pick me,” I said, once again trying to be confident.

“Let me show you something, Jenny,” he said, then stood and walked to the other side of his office.

I got up and followed him. We stopped by a wall that had pictures of all the current store managers. He explained that out of the 16 stores in his district, there was only one female store manager and that most of the current assistants were males too.

“With your work ethic and noble attitude, maybe you can start changing this number in the future,” he explained.

Store manager, I thought to myself. It almost sounded like he wanted to fast track me into the position once I was promoted to assistant. To be polite, I took a little time to look at the pictures, showing interest in them. As I did, I felt him put his hands on my shoulders from behind. I ignored it as a friendly gesture and continued looking until his hands moved down and forwardly cupped my breasts. I tensed up and didn’t move, shocked by what he was doing.

“I’ll make sure you stand out among the other candidates,” he said quieter, his hands slowly pulling the buttons on my blouse open.

Once he had my blouse open, he put his hands on my shoulders again and turned me around to face him. I refused to make eye contact and hoped it was some kind of joke or prank, maybe even some sort of initiation. He pushed my bra up to uncover my breasts, then looked at me. His hands reached and cupped me again, his thumbs swiping over my nipples. I finally tensed up and pulled away from him.

“I’m not doing this!” I said, shaken up.

“That’s a shame,” he responded.

I moved toward the door while fixing my bra and blouse, then left as soon as I was proper. I went into the bathroom again and locked the door, so I could take a few minutes to calm myself down. As I thought about what to do, I took deep breaths. It was going to be my word against his if I decided to report him, and I wasn’t sure that I wanted to go through the stress of it. I beat myself up mentally for letting it get as far as it did. My shock shifted into anger as I thought about the possibility of not getting promoted. I checked myself in the mirror again then went back to his office, where I barged right in.

“I still expect to be promoted,” I declared. “My work is excellent, and I shouldn’t have to have sex with you to be recognized for it.”

“Oh, you came back,” he said, looking up at me. “You’ll be graded appropriately for your actions,” he said, being vague.

“On my work, and not on my body,” I said again, still mad. He didn’t answer, and instead, starting writing. “Hope you enjoyed my tits,” I said sarcastically, then left.

At home, I spent the rest of the day in my room and only talking to Andy briefly when he came home. I laid in bed while browsing on my phone, trying anything to take my mind off what happened. I knew there was no way I was going to get promoted now, which was going to be an issue since I was taking over my parent’s house soon.

( The letdown )

For two days, I kept to myself and my thoughts. I waited for my phone to ring with a call from my job about my status. I didn’t have a work schedule, nor did I know if I was going to be promoted or fired. Like the last couple of days, I sulked in bed, doing nothing but watching videos on my phone. That lasted almost half the day until Skylar texted me.

“Hey babe,” he texted. “I was hoping to see.”

“I’m home today, so I guess you can come over if you want,” I replied.

I had made up my mind that I needed to break up with Skylar. Even with him on his way over, I still didn’t know how I wanted to do it, or what to say. Since I was still in my sulking mood, I didn’t even bother to get dressed and, instead, remained in my t-shirt and pajama bottoms. He didn’t take long to get here and sent me another text when he did.

“Hey,” I said as I opened the door.

“Hey,” he said with a big smile, then pulled me into him to kiss me.

“We need to talk,” I said after the kiss, even knowing how cliché it sounded.

Not knowing what else to say, I decided to be blunt. “I can’t be your girlfriend,” I said after we sat down.

“You’re breaking up with me already?” Skylar asked, sounding disappointed.

“I’m sorry,” I said. “I know this sounds like an excuse, but I really do like you. The thing is, I love Andy, and I feel like I’m supposed to be with him.”

“I knew it would be Andy,” he sighed. “I hope he knows how lucky he is to have such a sexy lady.”

“I’m not exactly sexy right now,” I rebutted, giving myself a look over and remembering that I hadn’t taken care of my hair, nails, or anything after what happened.

“You look sexy to me,” he insisted. “I wish this wasn’t happening, but I guess I understand why. Since we’re being honest, though, I did come over here to fuck, so if it’s over, then I’ll head out.

“You don’t want to talk or anything?” I asked as he stood up.

“You’re dumping me less than a week later, so I’m not in the mood to talk,” he said. “If you ever change your mind, or just want to fuck, shoot me a text or something.”

I started to cry as Skylar left, feeling terrible for hurting him. My job and the thoughts of my interview overflowed into my mind, too, making me cry heavily for several minutes. As it all came out, I slowly calmed down and even felt a little better.

Now that I had broken up with Skylar, at least I could tell Andy we could get together. The thought of us living together in a house as a couple actually made me happy. It also meant that I could finally put my mind to rest on who I should date. I pulled myself out of the slump I’d been in and cleaned myself up. I shaved, showered, did my hair, and touched up my nails. I took extra care to make my toes look cute and put on a pair of open-toed heels since I remembered he has a thing for feet.

When I heard him coming in, I checked myself one last time, then tried to fluff my cleavage a little more. I stepped out of my room and stood in the living room, waiting for him to notice. While waiting, I wondered if I should say something sexy, or make a joke, or maybe say nothing and see what he says.

“Oh, hey, you’re actually up and about,” Andy said. “Alice, this is Jenny, my best friend, and roommate,” he said again as a woman came in a moment after him. “Alice and I met up yesterday after meeting on the app.”

“Hi, nice to meet you!” Alice said with a smile.

“You too,” I said, forcing a smile.

“Looks like you’re about to go out too, so I won’t hold you up,” Andy said.

I quickly went back into my room, feeling a pain in my chest and shortness of breath. Tears started to pool up in my eyes again, but I forced myself to calm down, not wanting to cry anymore. I undressed and threw my clothes into a pile before sulking in bed for the rest of the day. I woke up sometime later to the sound of Andy and Alice having sex. Instead of being sad, I felt a bit of anger. Everything seemed to have gone wrong for me this week.

( Not giving up )

My dreams were filled with sex. I was in the district manager’s office again, bent over his desk while he fucked me. This dream repeated in different variations all night, though, they were more like nightmares. When I finally woke in the morning, I was wet. The familiar tingle of arousal was also present. I ignored it, not wanting to masturbate or orgasm from anything stemming from that sex nightmare. At the same time, I knew that I didn’t want to let this continue any longer.

I ate breakfast, showered, did my makeup, and dressed as womanly as possible. Looking in the mirror, I worked on a business face, practicing it, so that I could look as professional and serious as possible. As I made my way to the office, I thought about what I wanted to say. I intended to get my thoughts out so they wouldn’t be on my mind any longer or disturb my dreams. I had no idea if this was the right thing to do.

I had to wait to see the district manager, which gave me more time to work on my thoughts. When my time came, I went into the office, walking, so my high heels clicked on the floor with authority. I closed the door firmly, then turned to look at him. This was my moment to retake my womanhood and pride. I saw down in front of him, sitting up straight, then smiled slyly.

“I work hard for this company, and just as much through my training. I thought about coming back here to let you fuck me just so I could get my promotion. I’m not going to do that, though. I know I’m qualified for this job, and you don’t need to put your dick in me to know that. So, either promote me or fire me and be done with it.” I stopped and continued to look at him.

“Is that all?” He asked, sitting back in his chair casually. “Why didn’t you do like the other female candidates, take the offer or quit?”

“Why should I do either? If other women want to fuck their way to success, then that’s their choice,” I said, holding my ground.

“Since we're speaking candidly, I’d still love to fuck you. Since you deny that offer, yes, I do agree that your work ethic is good. I’m also impressed by you coming here to challenge it.” He sat up again and began looking at papers on his desk. “I think I have a different position to offer you.”

“I don’t want some consolation position just to keep me quiet,” I rebutted.

“That isn’t what I have in mind. The contrary, actually. I want to offer a better position. Front-end specialist for the district,” he said, handing me a paper that highlighted the responsibilities.

“Oh,” I said, surprised by the offer. I was sure I’d be fired today.

“If you agree, I can get you set up today, and you’ll start next week.”

I accepted the position, then went through the process of being put in the system. It came with a significant pay raise, a work phone, and even a work car. The downside was that he was going to be my direct supervisor. I hoped that after today, I made a clear line that he wouldn’t try to cross again.

( Myself )

My life seemed to be in fast forward, with many events happening rapidly. Not only did I have to get used to being a female so quickly, but I had also already experimented with sex, relationships, dating, and breaking up. Now I had gotten a significant promotion at my job, and my parents were going to be moving far away soon, which meant I would have an entire house to myself. I decided to use the few days I had left before going back to work to just be myself.

Leslie had helped me find my way as a girl, which I much appreciated. It was time to find myself now, something that I mostly had together when I was a guy. I tried to carry over the same me when the change happened, but now I realized I don’t feel the same way anymore. Looking around my room, it was easy for me to see that it didn’t match how I felt now. Except for my video games, almost everything else felt alien. The colors, posters, figures, and other decorations.

Getting the house to myself and moving back was the perfect opportunity to make a personal change. In between shopping online and going to the store, I started to collect things I found more to my liking now. Most were items that I would’ve never even looked at as a guy, but I put those thoughts aside, which was becoming easier as time went on. As for the old stuff, I started taking them down and packed them up since I was going to be moving soon anyway. The same went for other things I wouldn’t need right now.

By the last day of my time off, I had at least a dozen boxes packed, which left me feeling a bit accomplished. I still hadn’t spoken to Andy much, though I still considered him my best friend. I just needed time to get myself together. With all the errands for the day finished, I got my laptop out and poked around on social media. I had added a pic here and there, but I didn’t usually spend much time on social sites.

There were dozens of requests waiting for me and just as many messages. It was strange considering that I hardly ever use it. Without overthinking, I approved all of the friend requests. The messages were random “Hellos” and “How are you?” I had even more notifications than requests or messages. My few pictures had gained quite a few likes and comments. A few more minutes of browsing led me to the source of this sudden attention. Someone with a lot of followers had shared a picture of me. It was a mirror selfie I had taken after putting on black lipstick just for fun.

Something felt good about having all of these people liking my pic. This particular photo had been taken when I first started practicing with lipstick, so I decided to take a new one. I had gotten practice in since then too, so I applied the same black color to my lips again. I snapped a pic and looked at it, then decided to do a bit more first. Time went by, and before I knew it, I had done my eyelashes, put on eye shadow and liner, and did some foundation. I snapped several more pics until I had one with a good angle and lighting, then uploaded it. In the caption, I put: “Thank you all! Here’s a new one!”

( Wet dreams )

It was hard to fall asleep while thinking about starting my new position tomorrow. When I finally did get to sleep, my dreams were vivid. I dreamt of being a kid again, out with my parents, except I was a girl. The dream was like I had been a girl all my life. I found myself dating Andy later. We were never best friends, but instead, he had always known me to be a girl. I lost my virginity to him in my own bed while my parents were out. The weirdest part of this dream was when my parents came home and caught us. Even as I tried to get Andy to stop, he didn’t, and my parents walked in. They watched as Andy continued to drive himself into me, over and over until he finally finished with one last deep push and came inside of me. Instead of freaking out, they started commenting about how I was going to give them a grandchild now.

I found myself in my district manager’s office again in my next dream. This one was far longer and even more vivid than the last. He had me undress, piling all my clothing on the floor as I did. I stood there, completely naked as he watched me for several minutes before getting up. He came around the desk, picking my panties up from the floor, then showing me a safe where there were at least a dozen others.

“See, you’re not the first, nor will you be the last. Smart women know how to use all their tools to get ahead,” he said with a big smirk.

I couldn’t speak or move unless he wanted me to, no matter how hard I tried. He placed my panties with the others, and then it began. His hands unzipped his pants, then pulled his dick out, which was already hard. With just a mere motion of his hand, I went to him, dropped down, then put him in my mouth. Even as I sucked his dick, he still didn’t give me his full attention. Instead, he was on his phone, texting, then making some phone calls.

From there, we moved to his desk, where he sat me on top of it, spread my legs, and shoved himself inside of me. I now wished he had continued talking on the phone instead of trying to kiss me, my neck, and my breasts. He eventually pushed my down on my back, wrapped his hands around my legs, and began to fuck me more aggressively. I put my hands over my breasts to keep them from bouncing and kept my head turned to the side.

He just kept going and going like he never intended to finish. Then, almost as if he heard my thoughts, he told me he wasn’t going to stop until I came. I didn’t want to have an orgasm with him. It was bad enough that it was already making me feel good. He kept saying it, though, telling me to cum every few moments. Now, each time he said it, I felt myself get closer.

I woke up, sleep heavy in my eyes, but with a hot throbbing in my center. It exploded and made me shiver, even as I was still half asleep. I sat up and squeezed my legs together as I came. My orgasm was intense and prolonged, then when it was over, I had to get up and take off my panties as they were too wet. I went back to bed just like that and tried to sleep until morning.

When morning came, I woke up and readied myself for work. Despite the prior week and my creepy sex dream, my first day at work went great. I took a rideshare in, then completed my onboarding. Soon after, I was given a work car, which wasn’t the best, but it was still a car. Over the next couple of weeks, I used the car and my new salary to purchase new clothes, since my new position required a different dress code.


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