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My Unwanted Transition 5


( Complicated )

Skylar stayed in touch with me every day via text messages, and I also talked to Leslie and Andy. It had been two weeks since meeting Skylar at the mall, and I hadn’t met up with him since. My birth control was also in full effect now, but I haven’t gone to see Andy either. Every time he asked I came up with something that I was busy with, like work or running errands. I felt like if I went over to his place, then I would have to tell him about Skylar. Of course, I wanted to hang out with Skylar too, but just like with Andy, I knew sex was going to be inevitable, and I was nervous about having sex with Skylar. Somehow, it felt like it was going to be different if I had sex with Skylar. With Andy, we were just friends doing stuff, but with Skylar, it would put the last stamp on me being a girl. It made sense in my head at least but knew it was sound crazy to anyone else.

Despite my reservations about the guys, I continued to embrace my new body and practiced with the makeup I had gotten at the mall with Leslie. Luckily for me, there were tons of video tutorials online. My mom inevitably caught on that I was wearing makeup and she offered to help as well when she saw that I had messed up some.

This morning I finished my makeup, and my mom gave me her seal of approval before I went off to work. During my break, Leslie came over and joined me as she usually did when we could.

“So, when are you going to see Skylar again?” Leslie asked. “You like him right?”

“I do. It just isn’t easy to start dating a guy when I never looked at guys like that before.” I sighed.

“Have you told Andy about the pics you sent to Skylar?” Leslie continued her questioning.

“I haven’t even told him about Skylar at all yet.” I could feel Leslie’s eyes drilling into me.

“Girl, you’re gonna have to tell them something. I know Andy is your best friend, but its gonna be different no matter what now that you’re a girl. Guys are different when they’re with cute girls. If he’s attracted to you, then he might think he deserves first dibs on being with you since you guys have been friends so long. If I had a best friend that turned into a hot guy, that’s how I would feel.” Leslie lectured.

“Andy isn’t like that though,” I rebutted.

“I mean, I hope you’re right, but the guys have instincts just like women, and they want to have us if they think they’re entitled, no matter how crazy it might be.” Leslie ended her argument there.

I thought about what she said for the rest of the day and tried to reverse the scenario in which Andy had become a girl, and I was still a guy. Going from no girlfriend to being best friends with a hot girl willing to have sex with me would be quite an upgrade. Thinking about it realistically, I would be upset if Andy chose to go with another guy too. Then, it suddenly hit me that I would be upset if he decided to go with another girl now. Life was so much simpler before, I thought to myself. I knew it was time to go see Andy, and maybe right after work too.

After work, I decided to walk home. It wasn’t too far, but most days I either got a ride or ordered an Uber. As I walked, it gave me time to think about what to say to Andy. Leslie had made good points too. I didn’t know what Andy wanted and just assumed. I barely even knew what I wanted. It was just supposed to be sex for fun with a friend, and not an attraction to a guy I met at the mall. I knew if I chose to keep sex between Andy and me, then Skylar wouldn’t want to see me anymore either. I had no idea how Andy would feel about Skylar, especially after what Leslie said. After collecting my thoughts for a few minutes, I decided to start with how Andy felt. If I knew that, then I could try to make a decision on what to do. With that in mind, I started to walk faster so I could get home and change, then head over to Andy’s place. Just as I was coming up on the last block, I heard a voice come from the car pulling up beside me.

“Well look who it is!” I heard them say as the car came to a stop. When I leaned over to look in the window, I could see Skylar driving. “Do you need a ride?” He asked.

“Um. I don’t live much further,” I answered.

“Oh, well, if you’re not busy then maybe we can hang out, he offered.

“I don’t know. I’m a little busy today,” I said, trying to break it off easy.

“I’m sorry if I came on too hard at first. If you don’t want to hang out anymore, I understand,” Skylar said, making me feel kinda bad.

“No, that’s not it. I’ve just been busy with stuff,” I said, trying to think of something more specific.

“Okay then, I won’t bother you if you’re busy. Text me sometime,” Skylar said, then turned to get ready to drive away.

“What did you have in mind?” I asked quickly.

“I don’t know.” He paused. “I could jerk off in the car for you again,” he said, then laughed.

I shook my head at his terrible joke, but at the same time, I actually thought about him doing that again. Conceding, I walked over and got in the car. As he drove, I thought about what to say, and how long I could hang out before it was too late to go and see Andy today.

“So, what did you want to do?” Skylar asked.

“Weren’t you gonna jerk off?” I joked.

“I can’t while I’m driving.” He laughed. “Unless you want to do it for me!” I just laughed softly and shook my head. “Anyway. If that whole sexting thing was too much, I’m sorry.”

“No, its okay, I liked it,” I said.

“You have such a banging body too,” Skylar said. “Don’t worry though, I deleted all the pics and videos you sent.”

“You didn’t have to,” I said, but was relieved that he did.

“I know, but when you got kind of distant after, I figured you probably regretted some of it, so I got rid of them. You can even check my phone if you want,” he offered.

“I believe you,” I responded. It made me happy that he cared that much.

“I’m guessing you have to live around here somewhere,” Skylar said, slowing down.

“Oh, are you taking me home? I thought you wanted to hang out,” I asked.

“You said you were busy, so we can hang out later on.” He smiled.

I pointed him toward my house, which was just around the block and he pulled up in front. It felt a bit weird about getting a ride just up the street.

“Text me sometime when you want to do something,” Skylar said after he parked.

“Um.” I looked at my house and then at him. “You can come inside if you want.”

“Want me to meet your parents already huh?” He said with a laugh.

“They’re not even home!” I said quickly, trying to debunk his joke. “Anyway, I’m going in, so you can come if you want.”

I got out of the car and headed inside. Skylar locked up and followed. I don’t know why I invited in, but since I did, my plan for going to see Andy was growing slim. Or maybe I invited him in to delay going to see Andy.

“I don’t really know what we can do, but there are drinks in the fridge, and you can put on the t.v. If you like. I’ll be right back.”

I went to the bathroom upstairs, wanting to clean myself up since I had been at work all day. I checked my hair, face, and body to make sure I wasn’t sweaty or smelly. After washing up a bit, I went to my room so that I could change into fresh clothes. I stripped down to my bra and panties, then looked for a cute matching pair. I changed my bra first, then as I slid my panties down, I saw spots of blood on them. “Fuck,” I said to myself. Despite everything I had been thinking about, I didn’t want to miss another chance if Skylar wanted to have sex. Frustrated, I handled my woman needs and got dressed.

I went back downstairs to find Skylar flipping through the channels and took a seat on the opposite side of the couch so I wouldn’t lead him on. He just kept flipping, and since my parents had every channel for some reason, there were a lot. When he finally found something at least mildly interesting, he put the remote down.

“Oh, you changed and got all prettied up,” he said as he looked over at me.

“Yeah, I wanted to get out of my work clothes,” I said, then looking at the t.v.

“Cute socks,” Skylar complimented again.

“Thanks.” I smiled.

I was wearing a pink top with cream colored capri pants and pink socks that had white stripes going all the way up. Even as I watched t.v I could see him out the corner of my eye looking at me. The arousal that had been growing in me all day started to pick up even more. After a few minutes of t.v, I figured that he wouldn’t want to spend the rest of the day just sitting here.

“Is there anything you want to do?” I asked.

“Um.” He seemed to think for a moment. “Just you,” he answered.

His answer caught me off guard, and it took me a moment to realize what he was saying. Before I could think of something to say, Skylar got up, walked over and sat next to me.

“Jen. Ever since that night in the car, I thought you were amazing, then after you send me pics and videos, I really couldn’t stop thinking about you. Maybe its just because I’ve never met a girl so open to that stuff.”

“I guess I am different from most girls,” I said, which was the truth. I wondered what he would think if he knew that truth.

“I hope I'm not too forward, because, as you know I can be. But, I don’t want to go after something that isn’t there, so, I will ask, do you like me?” Skylar asked.

“Yes,” I nodded. His forwardness was a huge turn on from the start.

Skylar leaned into me, putting his arm around my body as he kissed me. His lips pressed against mine, then his tongue pushed forward into my mouth. It was incredibly weird to kiss a guy, but it made me feel so hot. I opened my mouth more and pushed my tongue against his. Before I knew it, his hand was well up my shirt, pushing my bra up so that he could squeeze my breast. Without realizing it, I made a soft moan in the kiss.

“I want you so bad,” he said just after breaking the kiss.

“Wait,” I said softly in response, trying to give my mind time to catch up.

He started to kiss my neck and pulled my shirt up in the process. As he kissed lower, his hands came around to unhook my bra. With it out of the way, he moved down and flicked his tongue over my nipple, then waited for it to get hard before looking up to smirk at me. He took it in his mouth and sucked which felt so good. When he moved to my other breast, his hands went lower and started to loosen my pants, but I quickly put my hands on his.

“Wait,” I finally said again. This time he stopped. “I can’t. It’s kind of that time for me,” I tried to explain without being too detailed.

“Oh,” Skylar responded, moving his hands. “I guess I’ll have to make you cum some other time.” He grinned and kissed me again. “Want to stop then?” He asked.

I shook my head. “Let's go upstairs,” I said. I didn’t want my parents to walk in and see me half naked with a guy.

We went upstairs to my room, and I finished taking off my shirt and bra. He resumed where we left off, putting his arms around me and kissing me more. Slowly, we moved toward the bed and sat on the edge.

“I guess I can jerk off for you now.” Skylar laughed.

“At least you’ll be more comfortable,” I added and laughed too.

He put his arm around me and held me close as he leaned over to mouth my nipple again. His free hand worked his pants and eventually pulled his hard dick free. He started to stroke himself while alternating between sucking my nipples. They were more hard and puffy than I had ever seen. I watched him jerking off, almost remembering what it was like to have my own, but as I tried to remember the feeling, my body reminded me that I no longer had one with an aroused throb inside my womanhood.

I reached over and took his cock in my hand, wanting to make him feel as good as he was making me feel. He moved his hand and let me take over while he moved up to kissing my neck and eventually finding my mouth again. We kissed deeply as I stroked his dick and I liked how firm and warm it felt.

“That feels so good,” he groaned and leaned back some to watch me.

Without getting lost or stuck in my thoughts, I followed how I felt and leaned over, taking his cock right into my mouth. I always knew that I would never put another guy’s dick in my mouth, but it felt so right, and I wanted to make him feel good. As I moved my mouth up and down on him, I moved from the bed and down to my knees to make it easier. I felt his hand move to the top of my head, giving me a little push. He raised his hips now and then, trying to push more into my mouth which made me gag a little. I tried to think about what I would like and replicated it. When I came back up again, I licked around the tip and could clearly taste his pre-cum.

Every time Skylar groaned, fuck, yes, and god, it made me even more into it. He started to push my head down more while pushing his hips up. I felt his cock reaching far back in my mouth, and I took as much as I could before pulling myself back up. Everything in my room seemed so quiet which made the sound of me sucking his dick seem so loud.

“Where do you want it?” Skylar asked. “I’m close.”

“Um,” I said, pulling my mouth off. I never thought I would’ve ever had to answer that. “My boobs are fine,” I answered. I didn’t mind if he did it anywhere, but I thought saying that or my face would make me seem like a slut or something.

Skylar stood up, and I sat on the bed. With no previous knowledge or skill in giving blowjobs, I continued to do what I might’ve liked while also trying to replicate some things that I saw while watching porn. I started to jerk his cock in my hand while licking the tip and taking it into my mouth some. It took a little longer than I thought, but when he was ready, he started to stroke himself and moments after, hot spurt after spurt of his cum covered my breasts. It felt warm and thick, running down my skin. I felt so horny having made him cum like that.

Unlike porn though, no camera would just cut off here. I had a mess all over me that had to be cleaned up. As I stood up, Skylar kissed my cheek, obviously avoiding my mouth for the time being. I went to the bathroom, and before cleaning myself, I looked in the mirror and at his cum all over me. It was then I thought about Andy again. Instead of going to see him, I gave a guy a blowjob and let him blow a load all over me. I still didn’t know what to say to him, and now I had, even more, to add to it.

Skylar stayed over a while longer, and we talked about stuff. I found out that he didn’t like video games, which sucked. When I was a guy, I had always hoped to find a girl that liked gaming. Now, I was that girl, only to be faced with the irony of finding a guy who doesn’t like it. As the day went on, I wanted to make sure Skylar was already gone before either of my parents got home. I didn’t feel like having to introduce or potentially explain anything about Skylar yet.

“So, does this mean we’re official?” Skylar asked, stopping at the front door.

“What do you mean?” I asked for clarity.

“Like, are we girlfriend and boyfriend now?” He asked more specifically.

“Um, I don’t know,” I said, then I thought about it for a moment. “I guess I have to think about it.” I could tell that was a little disappointing to him.

“Friends with benefits then?” He asked on the rebound.

“Maybe,” I answered and gave a small smile.

( More Transitions )

“Have you talked to Andy or Skylar yet?” Leslie asked as we drove to the piercing and tattoo parlor.

“I saw Skylar a few days ago,” I answered.

“Really!?” Leslie asked excitedly. “Did you decide to date him?”

“Not exactly. It was just some fun,” I said, wishing it didn’t sound so bad after. “I still need to talk to Andy, but I haven’t found a good time to do it.”

“Jen. For your own good, you need to pick and tell the other. It won’t be good to lead both of them on,” Leslie advised.

“I don’t know how to pick. Andy has been my friend for a long time, and it just feels easy to be with and around him. Skylar though, I do like him, and he makes me feel good. I like that he treats me naturally like a girl because he doesn’t know my past, but then I also worry about that because I know I should eventually tell him,” I said, then took a breath.

“Girl, you don’t even know if Andy wants to date you.” She shook her head as she parked the car.

“We had sex though,” I argued.

“What guy wouldn’t take easy sex?” Leslie asked. “Guys have no problem having sex with a girl without having to date.”

“Skylar wants to date me though,” I said, trying to defend my thought more.

“Maybe Skylar really likes you, and Andy just wants the easy sex,” Leslie explained. “If you want to know for sure, you need to talk to Andy.”

“This seems so difficult,” I sighed. “Maybe we can just date each other,” I suggested.

“I do not swing that way,” Leslie said with a laugh. “So, unless you turn back into a guy, there’s no way.”

We finally got out of the car and went inside. Leslie had talked me into finally getting my ears pierced, so here we were. I looked at the options for all of the piercings, finding myself learning about types that I didn’t know of. There were different ear piercings, and they also did lip, nose, tongue, nipple, and clit, with different variations of those as well. Leslie was getting her tongue pierced, so they took her back to get it done.

I continued to look at the different piercings, knowing that I only wanted to get my ears done. Even just for ear piercings, there was a bunch of different kinds. Since Leslie already went back, I was left with my own thoughts and opinions on them. The thought of getting more than just my ear-lobes pierced crept into my mind as I looked at the other options. I always liked girls that had multiple ear piercings, so that helped me decide.

Leslie was waiting for me when I finished, her eyes widening when she saw that I had my ear-lobes done as well as my helix. Excitedly, she opened her mouth and showed me the stud in her tongue. Since my ears were sore, I just had her take me home. It was going to take weeks for my piercings to heal all the way.

It took a few days for me to stop thinking about the piercings in my ear. Every time I thought about them, I had to reach up and touch them, which just irritated my ear more. The day turned out to be good and my period was short and over, so I was in a good mood, especially since I had tomorrow off. As I walked home from work, I decided it was time to face Andy with everything.

“Hey!” I texted Andy.

“Sup,” he texted back.

“I was wondering if I could swing by today?” I asked.

“Actually, yeah, that would be cool, I wanted to ask you something anyway,” Andy replied.

When I got home, I took a shower, got dressed and put on some makeup. I didn’t want anything to distract me or tempt me away from going to get this done today. Once I was ready, I ordered a ride on my phone and made my way over to Andy’s place. For the whole ride and as I walked up to his apartment, I thought about what I should say and about what he wanted to ask me. Was he going to ask me to be his girlfriend? If he did, should I say yes? I didn’t want to creepily stand in front of his door for too long, so I finally knocked.

“Wow! Jen?” Andy asked when he opened the door.

“Yeah, it’s me,” I answered.

“Damn, I knew you made a pretty girl, but now you’re just sexy as hell,” he said, eyeing me up and down.

“Leslie has been helping me be more of a girl,” I explained.

“Is that why you’re so busy all the time?” He asked as we went inside.

“Well, there’s that, and work too,” I answered. “So, what did you want to ask?” I asked as we sat down in the kitchen.

“Oh yeah, so, I wanted to ask if you’d be interested in moving in with me,” Andy said, looking at me. I guess that answered my question already.

“You want me to just move in? Are you sure?” I asked.

“Of course I’m sure. I’m having a hard time finding a roommate, and it’s really put a toll on me financially. Besides, we always talked about getting a place together. I mean, I know that you’ve had a lot to go through, so if you’d rather not, that’s cool.”

“Oh,” I said at first, feeling dumb for misreading his intention. “I guess I need to know how much so I can think about it.”

Andy got up to get some paperwork and the lease so that I could look at it. I read over it and the amount, then divided it by two in my head, figuring that I would pay half. Then, I added up my weekly checks to see if I’d have enough for that and to live.

“What do you think?” Andy asked.

“It looks doable,” I answered.

“Great! How do you think your parents would feel about it?” Andy asked.

“They’re probably waiting for me to move out,” I said, laughing some.