My Unwanted Transition 7
( Stuck in the house )
When Andy left for work again, I started thinking about what happened with Skylar yesterday. The way he was so forward and aggressive had turned me on immensely. We still hadn’t had sex yet, but now he had a bunch of nude pictures of me. I felt myself getting aroused, thinking about how he used his mouth on me and then jerking off to my photos. Turning the TV down, I grabbed my phone and started to next him.
“Did you enjoy the pics?” I asked.
“Fuck yes! They made me cum like crazy. Too bad it wasn’t all over those sexy tits you have!” Skylar replied.
“Glad you liked them,” I sent back, with a smiley face.
“I can delete them now if you want,” he offered.
“As long as you don’t show them to anyone, then it's fine,” I answered, after thinking about it for a minute.
“Okay. By the way, I won’t be able to come over today. I have to go out of town for work for two weeks,” he typed back.
“Oh, no problem, I’ll see you when you get back then,” I sent, feeling a little disappointed, but maybe it was for the best.
“Hey! I’m off today and was wondering if I can come by?” Leslie texted as soon as I put my phone down.
“You can if you want,” I replied.
Leslie arrived around an hour later, and I crutched myself to the door to let her in. I did my mini-tour just like with Skylar before going back to sit on the bed.
“How’s the ankle?” She asked.
“Not too bad as long as I don’t put pressure on it or bang it against anything,” I answered.
“Sorry I left you hanging at the party. I was kinda… having sex with Matt,” she said.
“Really?” I said, not able to hold back a curious smile. “How was it?”
“I was pretty tipsy, but it was good from what I can remember. He has a big dick too,” she said excitedly.
“I’m glad ya’ll are doing well with each other,” I said, smirking.
“Yeah. What about you and Skylar? How are you guys?” She asked.
“He was here yesterday and helped me out most of the day,” I answered.
“Did you fuck him?” She asked, grinning.
“No!” I said, blushing some. “I mean, he was going to, but we ran out of time. He.. he ate me out really good, though.”
“Niiiiicee,” she said. “So, are you officially dating now or what?”
“I guess, maybe, I don’t know,” I answered, wondering about it myself.
“Maybe you should ask him,” she suggested.
“I don’t know. The day before yesterday, I had sex with Andy again,” I said.
“Ohhh. You’re still stuck between both of them. You probably want to pick one soon, unless you plan on playing them both,” she said.
“Yeah, I know, but every time I think about it, it makes my head hurt. I feel comfortable with Andy since I’ve known him for so long and we already know everything about each other. Skylar, I’ve been getting to know him, and I do like him a lot,” I explained.
“You know Skylar has the hots for you, but you also told me that Andy doesn’t see you that way. Do you just want comfortable sex with a friend, or do you want like a relationship, love, and all of that?” She asked.
“Is it wrong to want both? I like sex with Andy because there isn’t any pressure. But, every time I come close to having sex with Skylar, I get incredibly nervous,” I said, trying to explain.
“Trying to have both might cause you to end up with neither. If you were still a guy, would you want your girlfriend to be having sex with another guy all the time?” Leslie asked.
“No, of course not. I just mean that I want a good relationship that I’m comfortable in, not two guys,” I said to clarify.
“Well, then, you’ll have to either get Andy to love you that way or get yourself to feel with Skylar like you do with Andy,” she said.
I thought about Leslie’s advice for the rest of the day after she left. It became more clear to me that if Andy wanted to give it a shot, then I would choose him. Even on one foot, I decided to get up and try to cook. It wasn’t anything fancy, just some pasta, but I thought if maybe if I cooked dinner, it could help.
Every day Andy helped me before and after work by taking off and putting on the bandage around my ankle. I decided to make dinner every day, too, not only as a thank you to him, but in hopes that it could help build a different relationship. After almost four weeks, my ankle felt good enough to walk normally on again. My number one priority was getting back to work and catching up on the management training program since I was now weeks behind.
( Work & Andy )
I worked long hours and didn’t take any days off so that I could catch up on the training program. In between shifts, I managed to buy some new clothes to better fit the position. Luckily, Andy drove me to work and picked me up each day, which was one less thing I had to worry about. The only thing social I managed to squeeze in was going to the salon with Leslie to keep my nails done.
With work as my focus, other things like relationships took a back seat. It was the most normal I had felt in quite some time. My new challenge was now learning to be a manager, delegating, and everything that came with it. I was meeting a lot of new people and, at the same time, establishing my new public life as a girl. More people than ever were meeting me as Jenny and never knew me as a guy
Every day I worked at least 12 hours, wanting to make sure I finished on schedule for promotion consideration. Andy continued to give me a ride in the morning and picked me up at night. Outside of the car ride, we barely had time to talk, play games, or anything. This went on for eight full weeks.
On the last day, I stayed at work even later. When my shift was over, my training supervisor came to debrief me. She had me give a self-evaluation, and then we went over the next steps. She explained that all of the trainees were going to have a week off, then we’d meet with the district manager for final interviews. She gave me an excellent review, which I took, like almost a guarantee that I would get the job. I was confident that I did well and could see myself in the position already.
Since it was so late, I called a rideshare to get home instead of asking Andy to come and get me. When I got home, it was dark and quiet, so I was careful not to make noise. I took off my heels at the door and headed to my room, where I fell back on my bed to relax a moment. I kept thinking about the training and what it would be like to be an assistant manager. The extra money would mean I could help furnish our apartment more and maybe even get a car finally.
Things were getting better now after a long string of getting beaten down. There was still a week to go before I’d find out if I got the position or not, but the excitement was already bubbling in me. Along with that, I felt that warm tingle down between my legs. I moved my hand down, sliding it into my skirt and into my panties. My fingers found a surprising amount of wet, the slight touch to my clit, making my body shiver. It made me remember that it had been over two months since I last came, when Skylar went down on me.
I got up and walked over to Andy’s room and peeked in. He was sitting on the end of his bed playing a game, so I went in.
“I’m home,” I said.
“Oh, hey! Why didn’t you call me? I was waiting,” Andy said, turning to look at me.
“I didn’t want to wake you up.”
“As you can see, I’m awake anyway,” he said. “Want to play a bit?” He asked, holding up the controller.
I walked over and looked at the game for a moment, then turned and stepped in front of him. I took the controller from him and put it down, then stepped forward, straddling myself into his lap. The surprise on his face made me smile. Without a second thought, I leaned and kissed his neck, my hands reaching down. Thinking about feeling him inside of me made my already wet pussy throb. I tugged his shorts down just enough to find and maneuver his cock free. He rapidly became hard in my hand, which was plenty for me to lift up, pull my panties aside, and guide him inside of me.
His dick was hard and hot as it pushed deep into me, making me shiver with each inch it stretched. I placed my hands on his shoulders and began to lift and lower myself on him over and over. Eventually, his hands moved to my hips and pulled me more, thrusting upward into me as he did. I didn’t think about how I used to be a guy or anything else, only how good it felt and that I wanted to do this with him.
Andy moved his hands up and pulled my top open, then pulled my bra up. He took my nipple in his mouth, licking it, sucking, biting it. I didn’t stop though, I kept lifting and dropping my body against him, shoving his cock in and out of me. When he finished mouthing me, his hands gave my butt a tight squeeze.
“Fuck! You’re gonna make me cum,” Andy groaned, squeezing my ass even harder.
It turned me on that I was making him feel so good, but I was a little disappointed because I wasn’t quite there yet. I tried to slow down a little and reached to rub my clit, wanting to get myself off too. Anxiety was building in me, knowing that he was going to cum soon, so I rubbed my clit harder and faster. The harder I tried, the more I could feel my orgasm slipping away instead of getting closer.
“I’m cumming!” He called out as he pushed his hips up to plant himself as deep in me as possible.
Everything slowed down, and we both returned to the reality of me half-naked in his lap. I was still feeling horny since I hadn’t cum, but I was happy that he was feeling good. I pulled myself up and off of him slowly. Both of us had a bit of a mess from the mix of my wetness and his cum.
“What was that about?” Andy asked.
“Why? Did you like it?” I asked, not wanting to explain how horny I was.
“Yeah, but I wasn’t expecting that,” he said.
“Sorry if I did something wrong,” I added.
“No, I loved it,” he said again.
“Good,” I said, smiling.
He stood and walked up to me, putting his hands on my hips before giving me a soft kiss. “What time do you have to be at work tomorrow?” He asked.
“They actually gave us a week off. When I go back, I’ll find out if I get the position or not,” I explained, smiling more, happily.
“You’ll definitely get it,” he said in support.
“I hope so,” I said back.
“Well, do you play to play a bit then? He asked, referring to the games.
“Maybe tomorrow. I’m pretty tired,” I answered.
“Not tired enough to skip sex!” He said, making a joke.
“I guess not,” I said as I started to leave his room.
For some reason, his joke about sex bothered me. It was intimate for me, something I had just put everything I could into. The more I thought about it, the more I figured it was something stupid to be upset over. We always made jokes like that.
In my room, I undressed then sat naked on the bed for a while, looking up stuff on my phone. I was still frustrated that I didn’t get a chance to cum and why it was so hard to do it sometimes. My first thought was that something was wrong with my new body, but as I found information, I learned that a lot of women experience the same thing. Before I knew it, I spent a full hour looking up ways to make it easier. The most common advice was to relax and let myself enjoy the pleasure. Of course, by the time I finished reading, I wasn’t in the mood anymore, so I took a shower and went to bed.
In the morning, I got up early to make breakfast for Andy and me. I was already dressed, too, since I planned on meeting Leslie after. Andy had been an enormous help over the last couple of months, so I wanted to show my gratitude. As usual, we didn’t talk about sex and went on like nothing happened. After breakfast, I cleaned up as he went off to work. Not long after he left, Leslie arrived to pick me up, and we went to the salon.
I wanted to get a full manicure and pedicure since I found that I liked having my nails done. After the salon, we went over to Leslie’s place. To my surprise, she had moved to a new apartment, and it was well furnished. She had a new t.v., furniture, everything.
“I didn’t think anyone could afford this working at the store,” I said, shocked.
“I actually make more money on the side,” she said.
“Oh, are you like driving for ride-share or something?” I asked.
“Nope! I actually make more money than that,” she said, almost grinning.
“Are you gonna tell me?” I asked curiously.
“As long as you don’t tell anyone,” she said.
“I won’t,” I said.
“Well, I’m a cam girl,” she said. “I get naked on camera and do things, and people send me money.
“Like- on the internet?” I asked. “Like- the girls that masturbate on cam?”
“Exactly,” she said. “And I make a lot of money.”
“Wow, I didn’t expect that,” I said, not sure what to say.
“Come see,” she said, then walked down the hall.
I walked down the hall behind her and into one of the bedrooms. It was set up almost like some sort of movie set. There was a bed, a camera, toys, and a computer.
“This is where I work mostly now. I still work at the store, too, just for a guaranteed check,” she explained.
“And you just- play on camera?” I asked.
“I act on camera. I show them what they want to see as long as they tip me. I masturbate, use toys, laugh, giggle, cum. It’s all part of the show. The more you’re into it, the more money you can make. There’s a lot of competition, so you have to really put everything into it.”
“I definitely never excepted this,” I said, laughing. “I mean, if it pays well, and you like it, then great.”
Leslie showed me around the rest of the apartment. Her main bedroom was just as lovely, then she had a guest bedroom as well. It also had a full bathroom, then a half. It was much nicer than what I had with Andy. After the tour, we ordered some food for lunch and talked about everything. Except for the time we spent at the salon on occasion over the last couple of months, we hadn’t spoken much. There was quite a bit of catching up to do. I have to tell her about my time training, and she told me more about how she got into camming.
When the conversation shifted to me again, the topic of my complications between Skylar and Andy came up. Leslie always had good suggestions, I just needed to pull myself together and take some of her advice. The talk carried us all the way through the afternoon, and soon it was almost six.
“I guess it’s about time for me to get going,” I said, standing up and taking a much-needed stretch.
“Before I drop you off, I have a request,” she said, then pausing for a long moment as I waited. “Um, I’m going to be doing a show in a little while, and I wanted to know if you’d join me?”
“Join you on cam?” I asked, incredibly surprised.
“Yes, for a whole show. As I said, there is a lot of competition, and there’s a lot of demand for girl on girl,” she explained.
“I really don’t think I can just get naked and do stuff on cam, with people watching,” I said.
“It’ll be easy. You can just follow my lead,” she said, trying to convince me.
“I thought you weren’t into girls?” I asked.
“I’m not. It’s just a show. I don’t have to be attracted to you to put on a show,” she said again.
“I really don’t know, Leslie,” I said, already feeling incredibly nervous.
“I will pay you a thousand dollars,” she said, smiling.
The amount of money being offered made me freeze up. I didn’t know if she was being serious or joking. We both stood there as she waited for me to say something. I kept thinking about the money, then what it would take to get it. Being naked on camera for who knows how many people. What if someone that knows me saw it? The money sounded so good, but I couldn’t overcome that nervous feeling.
“I don’t think I can, sorry,” I said.
“That sucks. Well, if you change your mind, let me know,” she said.
Andy was already home when Leslie dropped me off. I went inside and changed into a t-shirt and shorts, and went to find Andy in his room, knowing he’d be playing games. As I looked in his door, I saw just that, Andy sitting on the end of the bed, playing a game.
“Hey, I’m home, can I join?” I asked.
“Sure, I was just about to find a different game to play,” he answered.
I sat down as he got the next game ready. We played our regular rotation, which was mostly cooperative games. This was one thing that hadn’t changed between us. From the first time we met, video games had been our shared hobby, and I was happy that we still had it. Eventually, we cycled through a few games and came to our favorite competitive game.
“We should make a wager,” Andy said, while the game started up.
“I don’t want to bet sex. I think we’re past that now,” I said.
“You don’t want to have sex anymore?” He asked.
“I didn’t say that,” I rebutted, then pausing since I still felt weird about my feelings. “I just rather have sex because we enjoy it, not because I lose a bet or game.”
“Oh, alright,” Andy said and looked a little surprised to me. “I wasn’t exactly going to propose sex.”
“What were you going to ask then?” I asked.
“I was going to say, if I win, you have to take a nude pic for me,” he proposed.
“We don’t need to bet on that,” I said, trying not to get upset.
We continued playing without a bet, but I decided to call it a night soon after. I knew it was stupid to be mad over Andy trying to make those bets. He just wanted an easy way to see me naked without commitment. It made me think that he wasn’t interested in anything more than being friends and having sex occasionally. When I got back into my room, I pulled my top off and took a selfie in the mirror, then sent it to Andy. I went to bed right after without checking for a response.
I got up early again, just like before, to get ready for the day. Since the only thing I had planned was to visit my parents, I dressed casually, before preparing breakfast.
“Thanks for the pic,” Andy said as he sat down.
“Yeah, and you didn’t even have to win a bet,” I said.
“I’m sorry. I didn’t mean to make you mad,” he said, not eating yet.
“It was stupid to get mad over it anyway,” I said.
“No, it’s stupid for me to keep trying to win things like that in a bet,” he said, countering.
“Especially since you can get it for free,” I mumbled, not sure if he heard me or not.
After breakfast, Andy went to work, and I went to my parent’s house. It had been quite some time