My Unwanted Transition 4
Updated: Dec 27, 2019
( Secrets )
Getting birth control had been a stressful few weeks. I didn’t want my parents to know I was getting it. Otherwise, that would be a dead give away that I’m having sex. I spent a lot of time researching different kinds of birth control, and I still had no idea which one I should get. Then there was the whole choosing a doctor thing too. In the end, I decided that I should see my same specialists since I would still be going to them for checkups. It would be awkward if during a test they found out I was using birth control.
I set up an appointment and gave them my cell number as the primary contact so that my parents wouldn’t find out. Andy gave me a ride to the office since this was going to be for his benefit too. I explained to them that I wanted to keep the visit and birth control between us. Since I’m not a minor, I was sure that they had to keep it in confidence.
“When can we do it?” Andy asked as I got into the car.
“I still don’t even have the pills yet,” I answered, waving the prescription in the air. “And I thought we weren’t gonna make that the only thing we do?”
“I’m not. Its been a few weeks since last time,” Andy chimed back.
I didn’t say anything else until we got to the store. It was true that it had been weeks since the last time and in fact, it was still the only time. There was still that mental struggle in my mind of having sex with a guy, even though it had felt good. I went inside the store myself and hoped that I wouldn’t run into anyone that knew me. As I gave the prescription to the pharmacy, I kept thinking about how much they might be judging me. A short time later, I had the pills in hand, and I returned to the car.
“My place then?” Andy asked, still attempting to nudge me into sex.
“It says we should wait at least a week. And since you don’t want to use condoms.” I shrugged. “Let's just wait to be safe; I don’t want to get pregnant.”
I could tell Andy was disappointed as he drove me back home. His friendship was appreciated more than he knew just by him not giving me a hard time about it. After he dropped me off, I went inside and found a place to hide the pills. Now, I just needed to make sure I would remember to take them and set the alarm on my phone to repeat every morning and hoped that would help. The thought of having sex with Andy still felt wrong, but I think I wanted it just as much as he did. I spent the rest of my day doing more organizing of my room which had been a slow process. There were still clothes and other things I had to go through and decide if I could still use them or not. Every time I tried to sort through them, I would manage to get rid of a couple, then the sentimental value of it all would start to kick in.
I quietly looked at some of my old clothes, thinking about my life as a guy. The memories were still clear, but it was getting harder to remember how it felt. I couldn’t even remember what it felt like to have a penis anymore or to have just a flat chest. After a few minutes, I shook the thoughts away and began grabbing clothes and putting them in a large trash bag. It was time for me to put my old life in the past because if I held onto it, it was just going to make my new life harder.
The next day I told my mom about all of the clothes that I didn’t need anymore so that we could plan to get rid of them. She seemed to know how hard it was for me and gave me a hug.
“We’ll take them down and donate them, then we can buy new some new stuff if you like,” she said, giving a smile.
“I’m already going with Leslie later,” I responded.
“That is your new friend from work right?” She asked.
“Not really new anymore,” I answered again.
“Have you told her about it?” She asked, continuing her motherly questioning.
“No, not yet…” I answered hesitantly, assuming she was talking about my change.
“Oh. Okay.” She gave me that hinting look of hers but didn’t say anything else.
I got ready for work and went to put my time in for the day before meeting up with Leslie later. After work, I walked about a mile to her house. It was my first time visiting her place and going inside. She led me inside and to her room, which smelled very good.
“You’re not going shopping in your work clothes?” Leslie asked, looking me over.
“Why not?” I asked, confused.
“We’re going to the mall, duh! We might see some cute guys.”
Leslie was just starting to apply her makeup as we talked. She was a hot blonde with long hair and a perfect body. Even though she was thin, her boobs had grown to be sizeable. In between putting on makeup, she rummaged through her drawers and closet, pulling out various articles of clothing.
“Put this on,” Leslie said, handing me some clothes.
It was a shirt with thin shoulder straps and a pair of very short, shorts. I started to head to the bathroom with the clothes and was stopped by Leslie.
“Where are you going?” Leslie asked.
“I was gonna change,” I turned and answered.
“You can just change here unless you’re shy or something,” she said, still doing her makeup.
I slipped my flats off, then started to undress. I took my shirt off first, then put the other shirt on and proceeded to do the same with my pants. Once my jeans were off, I pulled on those shorts. I hadn’t worn shorts outside since the change because it felt weird to show my smooth legs. It was my choice to shave, but being exposed to others was different for some reason.
“Looking good girl. Now let's get some makeup on you!” Leslie offered excitedly.
“I don’t think I really need makeup.”
“You don’t need it, but we can make you all super cute,” Leslie said, emphasizing need.
Leslie was quite energetic and ready to go for our girl's outing. It made me think about how I wasn’t being honest with her. She was standing there with that smile on her face, waiting to do my makeup. I sighed, knowing it was time that I had to tell her.
“Leslie. I have to tell you something,” I said, then pausing to let her sit beside me. “I’m not really a girl. I mean, I wasn’t always a girl.” I paused again, knowing how strange that must sound. “I was a guy, then I got sick, and I had to become a girl.” I realized that didn’t sound any better. “I know you must think I’m crazy.”
Leslie laughed a little. “I thought you were going to tell me that you’re in love with me or something.” She paused and composed herself. “I already know. You were Jason before. I worked with you for a few days at that other store. We didn’t actually work together, but I did see you, and well, I overheard you talking on the phone about this whole thing. I didn’t believe it at first, then a new girl shows up at my store, but has the same features as you. Even then, I wasn’t sure I could believe it, so I went over and talked to you when I could. Since you were so terrible at being a girl, I knew it had to be you.”
“You knew?” I asked in disbelief. “Why didn’t you say something then?”
“I was going to at first, but you looked like you needed a friend more than anything.”
“I guess I did, now that I think about it. But didn’t you say you just moved here some months ago? I was in those procedures and stuff for a long time.”
“Yeah, I sorta lied about that, sorry. I’ve been here about two years now. I wasn’t lying about not really knowing anyone though. The one good friend I made moved away.”
“I don’t know what to say.” I just sat there, stunned.
“How about we get that makeup on you?” Leslie smiled.
“Yeah, okay,” I said, still processing the information.
Leslie started to apply the makeup and walked me through what she was doing at the same time. She started with some foundation, then some concealer. Having her work on my face like that felt relaxing. After touching up with the concealer, she did some highlights before putting one set aside and pulling another set closer.
“Okay, now close your eyes and stay still. I’m gonna do your eye shadow.”
I closed my eyes and let her apply it, trying to be as still as possible.
“So, are you into girls or guys or both?” Leslie asked while continuing to put makeup on me.
“I still like girls,” I answered quickly, probably just to prove it to myself. “But,” I paused. “I was with a guy, and I liked it.”
“You had sex with a guy?” Leslie asked.
“Yeah,” I answered. “I liked it, but I don’t know if I like guys in that way, like find them attractive.”
“I guess that makes sense. Just because your body changed, doesn’t mean what you liked changed,” Leslie said.
“I don’t know, it's confusing. Somethings did change, like taste in food. There some stuff I don’t like the taste of any more, but that's easy. When it comes to sex or liking someone, my mind and memories tell me that I like girls, but when I think of a girl or see one, it doesn’t turn me on. If I think of a guy though, like a guy having sex with me, it will get my body going.”
“Girls are complicated,” Leslie said with a little laugh. “You’re a guy that all of a sudden had to be a girl, and you don’t know how to process all of the emotions and hormones.” She paused and put the makeup down. “Maybe try not thinking so much and just follow how you feel.” She smiled. “Now, just a little lip gloss and you’ll be all set!”
( The Mall )
Leslie took me to several different shops to look at clothes and shoes. She helped me find stuff that could be cute and others that could be for a more professional look. After the browsing through the first few stores and picking up a couple of things, she then took me to look at makeup.
“I can help you pick out some to get your own set started,” Leslie said.
I didn’t know anything about makeup, so I let her show me and tried to follow along. After makeup came clothes and then there were shoes. Before I knew it, I had spent quite a bit of money and had a load of new apparel. We went out to the car to drop some stuff off, then came back in to browse more. I told myself that I had spent enough money already, so I would only be looking now.
As we browsed more, I saw clothes that I always found cute on girls back when I was a guy and thought about if they would look good on me now. There were a few more things that I would’ve liked to buy, but decided against it since I still had to pay for other things.
“Some guys are checking us out,” Leslie said, laughing.
I looked around, trying not to be obvious. My eyes caught two guys off to the side as we walked toward the food court. I suddenly felt very aware about my legs being so exposed, and that other guys have probably been looking all day. There was a strange feeling about it and not a bad feeling either. I’m not sure how to explain it. I kept it to myself as we walked and finally made it to the food court.
“Mind if we ask a question?” A voice asked from behind us. Leslie and I both turned quickly and saw it was the same two guys.
“Do you either of you have a boyfriend?” One of them asked.
“I’m not with anyone,” Leslie answered with a little smile.
“Um, no, I’m not either,” I said after, completely caught off guard.
“Awesome! My name is Matt, and this is Skylar,” Matt said, introducing them.
“Leslie,” she gave her name while still holding a smile.
“Jenny,” I said, now smiling too so as not to look mean.
“So, we were wondering, how about we buy you girls lunch, then if you enjoy that, we can catch a movie later?” Skylar finally pitched in.
Leslie and I looked at each other, and I’m sure she could see the shock on my face.
“Can you give us a minute?” Leslie said to them, then pulled me away some. “First time being asked out?”
“Yeah.” I smiled nervously. “A customer did give me his number at work before though,” I added.
“Well, we are going to get lunch anyway. The worst that can happen is we get a free lunch right? I mean, we’d have to let them down gently after. They’re kind of cute at least.”
“I don’t know,” I answered. Leslie seemed so confident and practiced at this, and I felt like my heart was going to beat through my chest.
“You’re thinking a lot right? But, how do you feel about it?” Leslie asked.
“I feel like… I kinda want to do it.” I answered after a small pause.
“It’s a date!” Leslie chimed with a smile as we walked back to them.
They bought lunch for us, and we talked as we ate. After lunch, we just walked around the mall some while looking up movie times on the phone. Skylar seemed to pull more to me while Matt and Leslie pulled to each other. I didn’t want to look or pay too much attention, but Skylar did have a nice build to him. His arms were lightly toned, and it made me wonder if he had abs or not. Thinking about a guy like that made me feel weird. It didn’t seem to matter though, I just kept thinking about it and even tried to imagine what his dick looked like.
Leslie and Matt had started to walk ahead of us a bit, leaving space between them and Skylar and myself. With it being just us two, we started to talk a little more, and Skylar started to walk closer to me.
‘You’re really pretty,” Skylar complimented.
“Thank you.” I smiled, feeling good from his comment.
“I hope you like me at least a little.” He spoke again after a moment of silence.
“Sorry! Yeah, you’re pretty handsome too!” I blurted out. “Sorry, I’m bad at this.”
“Don’t worry, I’m not an expert either.” He laughed.
My mind was racing, and I tried to prepare some responses in my head so I wouldn’t sound so clumsy when talking. We worked our way around the mall slowly, trying to kill time until the movie. It was obvious that they separated Leslie and me so that they could talk and flirt with us.
“Would you mind taking a selfie with me?” Skylar asked.
“Okay,” I answered simply.”
We stopped, and Skylar put his arm around me as we leaned in for the picture. He showed me the picture afterward. With our faces side by side, it was scary how easy it was to see that I was a girl. As we started to walk again, he fiddled with his phone a bit more, and I assumed that he was sending the pic to someone or posting it online.
Once we made it around to the theater, Leslie and Matt were already there. Skylar, having already bought me lunch and the movie ticket was now buying me snacks. I didn’t know what to think about it really. It did make me feel kind of good, but at the same time, my memories of being a guy told me that he was just trying to have sex with me.
The movie the guys picked was a horror film, which was such a cliché move to make. Andy and I had watched tons of horror movies, and there was only a rare instance that I would get caught by a jump scare. Once those jump scares did start, Leslie had reacted with jerk motions in her seat. It didn’t take long for Matt to put his arm around her and she leaned against him.
I was unphased by any of the scares even though the movie was good. Skylar looked over at me slightly each time a scare came up, likely checking to see if I was jumpy. With Matt and Leslie all snuggled up, I actually felt a little bad for Skylar. I waited for the next scare and made sure to jump a little, and I even let out a little gasp just to sell it. Right after, I leaned toward him as a hint, and he put his arm around me. When his arm pulled me in so firmly, I felt a little tingle go through my body.
( After the movie )
The four of us walked out to the parking lot, and Matt went to get the car they had come in, while the rest of us waited by Leslie’s car. It was dark, and the mall shops had all closed except for the theater. The only people around were the few getting into their own cars and leaving. After talking as a group for a while about the movie, Leslie and Matt slowly moved away and went to sit on Matt’s car, leaving Skylar and I on hers. I was sitting on the trunk with Skylar right in front of me.
“Did you like the movie?” Skylar asked.
“Yeah, it was good,” I answered, smiling some.
“I see a few parts got to you,” he smirked, making a joke about me leaning on him.
“Maybe a little.” I continued to play along since he didn’t know I just did that to make him feel better.
“So, did you have a good enough time to give me your number?” He asked, taking out his phone and motioning it at me.
“Maybe…” I answered again, this time stretching the word, then softly giggling.
As I told him my number, it was on my mind how much of a girl I sounded like when I giggled. Once he put the number into his phone, he called me so that I would have his number too. I added his name in with the number and saved it. He put his phone away, then casually brought his hands up and rested them on top of my thighs. It was then I realized how close he was standing. Before I had the chance to put my phone away, it beeped with a message from Leslie.
“Hey, car is open, gonna have a lil fun with Matt!” Leslie texted. I didn’t even have to look over to hear them getting into the car.
I felt myself getting nervous, assuming that Skylar was going to try and get the same from me. I knew it right from the start when the asked to buy us lunch, and I just kept telling myself that we could break it off any time. There wasn’t much I could do now unless I were just going to sit in Leslie’s car by myself and wait for her while leaving Skylar alone.
“Do you want to get in the car too?” He asked.
The question filled my head with different outcomes of what could happen. Would we end up making out or would we have sex or maybe he wasn’t trying to do any of that, which I figured wasn’t likely? I was also looking forward to having sex with Andy in a few days. What would he think and feel about me having sex with Skylar? I wasn’t sure why that was on my mind since we aren’t dating or anything.
“We can,” I said, trying to give a neutral answer.
Once we were inside the car, I tried to look over and see what Leslie and Matt were doing. With it being dark and the parking lot lights reflecting off of the glass, I couldn’t see anything. Being alone in the car with Skylar had my heart racing. I tried to control my breathing to keep myself calm, but I kept thinking about him making a move on me and what it might be. Even as I thought that he moved right beside me.
“You know, I never thought by the end of the day that I would be hanging out with such a sexy girl,” Skylar said.
“I’m not sexy,” I said in disagreement.
“Yes you are,” Skylar smirked. “From your soft hair and pretty face, all the way down to your cute toes.” He moved even closer, leaning some to touch my hair, then placing his hand on the inside of my thigh.
I felt heat surging inside of me like it was suddenly a hundred degrees in the car. Before I could think of something to say, I felt his hand cup my cheek as he leaned in to kiss me. His lips pressed against mine momentarily, then after a short pause, he kissed me again. His other hand was rubbing along the inside of my thigh on my bare skin. I tried to think of something to say or do that could slow this down without sounding too mean. My mind was racing through so many thoughts. I wasn't supposed to like being with a guy like this. What Leslie had told me earlier was also there. Focus on how I feel instead of overthinking, she had told me. I couldn’t but think that my next time having sex was supposed to be with Andy anyway. Did that matter though? It wasn’t like I was his girlfriend or anything.
Skylar’s tongue was now in my mouth, and I naturally kissed him back. His hand moved from my leg and had made way up my shirt while I was so lost in thought. My bra was moved as his hand cupped my breast, then his finger toying with my nipple. I couldn’t deny how good it felt, especially with how wet I was. Maybe he knew that too because as soon as I thought about it, his hand moved back down and started to slide into my shorts.
“Wait,” I said breathily, and he paused.
“What’s wrong?” He asked. I felt his hand moving lower.
“I don’t think-,” I started, then stopped to get my words right. “We just met today, so I think we should wait.”
“I’d be lying if I said that didn’t suck.” He waited a moment, then pulled his hand from my shorts. I felt a little relieved but also disappointed. “Since I’m sitting here with a massive boner and we have to wait for them anyway, do you mind if I jerk it?”
“I guess that’s fair,” I said, looking over at Matt’s car, then back to Skylar.
He reached down and pulled his hard dick out, then started to jerk off. It reminded me of my first time messing around with Andy. With nothing else to do, I found myself watching him, without realizing just how intently I was.
“Since Matt is probably getting laid over there, I don’t want to look like a loser. So, would you mind if I still tell him that we had sex?” Skylar asked, even as he stroked his cock.
“Um, I don’t mind, I guess.” I took a moment to answer, trying to think about the possible outcomes of that.
“God, you have me so hard!” Skylar grunted as he continued jerking. He was looking at me all over.
“I can tell,” I said, watching him.
He kept looking at me as his hand went up and down. Knowing that he was getting so worked up over me was making me feel very good. I couldn’t help but think about how it would feel to have sex with him and how his cock would feel inside of me. Would he fuck me slow, or hard, I wondered.
“I’m so close! At least let me see your tits!” He grunted out.
Without thinking about it too much, I reached down and pulled my shirt up, then did the same with my bra. Skylar focused right on my bare chest as I gave each of my nipples a little tug to get them hard.
“I love puffy nipples. And yours get so hard!”
I played with them more so that he could watch, circling them and rolling them between my fingers. After only a few more moments he quickly pulled his shirt up as he started to cum. His large load spurted all over his chest and stomach, and I started to regret not doing more with him. We looked around Leslie’s car and luckily found some tissues so he could clean himself up. After he finished, I realized I still had my breasts out and pulled my bra and shirt back into place.
“I’ve had sex in a car before, but never jerked it in front of a girl in a car though.” Skylar laughed as he fixed his pants. “I hope it wasn’t too weird.”
“No, it was good. And you have a nice dick.” I complimented. It felt strangely good and satisfying knowing that he came because of me.
When Leslie and Matt came back over, it wasn’t long until we all left to head home. Leslie admitted to having sex with Matt, and I honored my promise to Skylar and said that I had sex with him too. I also received a text from Skylar asking me to let him know when I was home. It made me smile to myself a little.
( Late night texting )
I was so tired when I finally got home having spent the entire day out. All of the bags that I had from shopping were just left on the floor of my room. Before getting into bed, I remembered that I still had makeup on and went to wash up. When I got back to my room and started to change, I realized that I was still wearing Leslie’s clothes. Once I finished changing, I laid down and sent her text.
“Hey. I have your clothes,” I sent.
“They look good on you! You can keep them,” Leslie texted back a few minutes later.
“I’m home. I almost forgot to tell you.” I texted Skylar.
“Good. Hope you had fun!” Skylar texted back.
“I did. Did you?” I asked.
“You know I did! Lol.” He responded.
“Yeah lol.” I texted again, not sure what to say.
“What are you up to now?” Skylar asked.
“Just laying in bed,” I said.
“Same. You should send me a pic!”
I thought about his request for a few minutes. Before I could respond, he sent me a pic of himself laying in bed with no shirt on. It was a really good pic too. I tried taking a few selfies, wanting to get a good pic like he did. Several selfies later, I finally had one that I was happy with and sent it.
“You look super cute even with no makeup on!” He complimented.
“Thanks,” I said with a smiley face.
“Also, just so you don’t think I’m a creep or anything, I don’t always get into cars and jerk off in front of girls like that. You just had me so turned on.” Skylar explained.
“Its okay,” I sent back. I could feel myself getting wet a little.
“I regret not being able to get you off too,” Skylar texted right back. I wasn’t sure what to say.
“Hopefully you at least had a chance when you got home!” He texted again after a few minutes.
“No, I didn’t,” I sent. “I just washed up and got in bed.” I sent again, not wanting to sound curt.
“After seeing your pic, I kinda feel like doing it again.” He said with a wink face.
I was getting horny all over again, picturing him jerking his dick while looking at me. I lifted my shirt and looked at my own breasts. My chest was a long way from being flat now, and for the first time since the change, it really hit me that I had tits. I had considered them nothing but a hindrance and an invasion of my body, but as I squeezed one with my hand, I could feel how real it was. It felt good to squeeze them, they were mine, my breasts, and they were sexy. I suddenly felt hot, and sexy, that the heat between my legs grew more and more. Without thinking about it too much, I snapped several pics of myself with my breasts exposed and sent them right to Skylar.
“God! You’re so fucking hot!” Skylar responded, sending a pic of his hard dick as well.
As I looked at the closeup of his hard member, I pushed my bottoms down and moved my hand between my legs to my waiting pussy. My body was happy to have my attention, and it sent a strong shiver through me as I touched my clit as if rewarding me for not ignoring it anymore.
“Tell me what you’re doing,” Skylar asked.
“I’m rubbing my clit,” I answered, trying to type with one hand.
He sent me a short video of him stroking his cock, and following my urges, I took a short video rubbing my clit and sent it to him. We exchanged several more pics and videos without even saying anything. I imagined how it would feel if he were fucking me. Why didn’t I let him in the car? I kept thinking.
“I just want to blow my cum all over that cute face.” His next text came in.
In my mind, I thought about him fucking me, then pulling out like some kind of porn video before moving to unload his cum on my face. I started to cum, feeling all of the built-up heat between my legs suddenly explode through my body. I couldn’t help but to arch my back and dig my toes into the bed. After my intense climax, I grabbed my phone and took a pic of my face with my mouth open.
“I came! Your turn,” I sent with the pic.
A few minutes later he sent me a video of him cumming. Our sexting session wound down after that, but the glow and confidence I felt about my body were still very much there. I gave both of my breasts a squeeze and smiled to myself. As we texted more, I started to think about how many naked pics I had sent him and I barely even knew him for a day.
“Please don’t share the pics,” I texted.
“I won’t, I promise,” he wrote back. Either way, I had sent them now and could only hope that he wouldn’t.