Man to Woman

by Jane Futa

  When we had both finished, I pulled out of her and helped her slide of the counter. “You really know how to show a lady a good time,” she said with a smile.

  “It’s rare I meet a genuine lady,” I replied. She couldn’t help but laugh as she picked her panties up from the floor.

  “You’re fun. I’m growing quite attached to you already,” she said.

  “Same here.”

  “But there’s time, still,” she said. “Let’s eat some breakfast and see where the day takes us.”

  She was the wildest woman I’d ever known. She was full of passion and more exciting than I was used to. Just as I sat down to enjoy pastries and coffee with Catherine, my cell phone buzzed on the counter. I picked it up and it was Jacob asking how my night went.

  I looked at Catherine who was taking a sip of her coffee and I smiled. “My night was absolutely breathtaking,” I told him. Catherine looked at me with wide eyes and pink cheeks.

  “Really, man? That’s great! You finally get some?”

  “Oh I got some, alright.” Catherine chuckled at my response to my friend.

  “Fuck yeah! Want to hang later? The buddies and I are thinking of bar hopping and maybe picking up more chicks.”

  “I’ll have to call you back, actually. I may be tied up for the afternoon.”

  “Oh…ok! Call me later, man.”

  I hung up the phone and returned to the dining table with Catherine. The morning sun was rising higher in the sky, illuminating my house a little more with each moment. I wasn’t sure what my time with Catherine would bring me, but I was all in. I wanted every moment with her that she could spare, and I wanted her to know that she had changed me.

  She didn’t seem like one for words, so I vowed to show her the best time I could. We made loose plans for the day, but never ended up leaving the bedroom. I’d never fucked so much in my entire life. By the evening, my body was sore and covered with sweat, but I had Catherine in my arms.

  Femboy Babysitter

  Chapter 1

  It was officially summer and everyone in town had a summer job, except my sister. Unless you consider babysitting a job. She was only 18 though and didn’t live on her own yet. I didn’t really live on my own yet either except during the school year. I was a 20 year old sophomore graduate that came home every summer. The jobs were better in my hometown and even though I was racking up student loan debt like crazy, I needed the summer cash for pizza sprees and video games to get me through the grueling semester.

  I was only going to college because I’d be kicked out if I didn’t. My dad wanted me to be an engineer and my mom just wanted to see that piece of paper. Neither of them understood the expenses of my lack of passion for the field. I was just hoping to slide by enough to land a job with a good training program once I graduated. But every summer the only thing on my mind was kicking back and raking in as much small change as I could.

  I had a few friends from school but most of them were back home. We’d get together on the weekends and talk girls or play video games. Some of us smoked a little weed, but that was never my thing. Greasy junk food was enough for me.

  I thought I had hit the jackpot when I got hired at my favorite restaurant. It was called The Cheddar Palace. Despite cheddar not being the ritziest of cheeses, it was the fanciest place in town. I heard the waiters got so much in tip money that some of them were able to make it their career. Some of them even pulled in what I’d hope to make as an engineer without ever having to go to college.

  Part of me hoped I could make enough to just quit school altogether. The other part of me wanted to at least avoid any more school debt. I knew my dad would never go for me being a career waiter, so that wasn’t really an option for me. I thought I would be on easy street with the money I’d make, but after my first day I started to worry.

  I came home and threw my apron on the kitchen counter with an exhale. I couldn’t get the smell of cheese and pasta out of my nose. I saw Brianna sitting at the kitchen table, counting her babysitting money.

  “How was work, jerk?” she asked without looking up from her smile of cash. “Did you spill cheese on anyone?”

  “Well at least I have a job,” I shot back, somewhat proud of my quick response time.

  “Babysitting is a job. Some people make it their careers.”

  “Sure,” I said while rolling my eyes. “Just make sure you have enough for gas money to your real job when you finally have to get one.”

  “I have plans this summer. I’m expanding. Soon, I won’t have to do any work and I’ll still be rolling in it. I’m officially starting a network of babysitters in town that can be on call.”

  “So a literal babysitters club?” I laughed while I opened the fridge to place my leftovers inside. The best part about working at your favorite restaurant is getting a discount on the food.

  “More professional than that,” she said with a tinge of acid in her voice. “You’ll see. I bet I make piles more than you this summer.”

  “I don’t know about that. Do you know where I work?”

  “Yeah, your stupid cheese place.”

  “Yeah. And it’s the most expensive restaurant in town. The tips I’ll make on one table alone will be more than you make in a whole night.”

  “And how did your first day go?” she pressed again.

  “Never mind that. All first days are rough. I’ll get the hang of it.” She rolled her eyes and laughed. She picked up her small stack of money and placed it in an envelope.

  Brianna stood up and walked over toward me until we were only a foot apart. “Care to make a bet?”

  “A bet about what?” I asked, folding my arms across my chest.

  “About who will bring in the most money this summer. If I win, you have to do something super embarrassing.”

  “Oh yeah? Like what?”

  Her eyes lifted toward the ceiling as she thought of something I’d hate. Little did she know I was up for most things. I wasn’t easily embarrassed.

  “You have to cross-dress,” she said.

  “What? That’s ridiculous,” I said. “And do what exactly?”

  “You have to dress up like a woman…and then…oh! You have to post a photo of yourself to all of your social media followers.”

  “No way. My buddies follow me on those sites. Some of my professors follow me.”

  “Oh come on, Chris. Don’t be such a pussy.” She stuck out her tongue playfully and I just wanted to tug on it to teach her a lesson. “Afraid you’re going to lose?”

  “No, I’m not afraid. Okay. Okay. And what if I win?”

  “What do you want?” Her eyes stared into me daringly. She knew I wasn’t the most creative person. All I really wanted was money anyway.

  “If I win…you have to…give me a whole week’s worth of your babysitting money.”

  “Deal,” she said faster than I had expected. A small wave of panic rolled through me. She was confident and it made me worry a little. It’s ok, I told myself. You work at an expensive restaurant now. You’ll soon be raking in the dough.

  She extended her hand out for me to shake it. I took hold of it and instantly felt weak in her grasp. She seemed determined to win. Fuck. What have I gotten myself into?

  “Good luck at work tomorrow,” she said in a teasing tone. I watched her walk upstairs with her long brown ponytail swinging behind her. My eyes darted back to my apron. I picked it up and held it to my nose, immediately gagging from the cheesy scent.

  “Ugh.” I sighed. I could only hope that tomorrow would be better.

  Chapter 2

  “When do we start making tips?” I asked another one of the new kids at the restaurant.

  “I don’t think we make tips for another two weeks or so. I don’t know. It goes by hours of training or something. The more you’re available to train the sooner you’ll be making tips.”

  “Fuck.” I was more available than anyone but they were still only giving me ten hours a week at minimum wage while
I trained.

  Training pretty much consisted of shadowing other waiters and occasionally reciting the daily specials. The closer a new hire got to the end of training, the more responsibility they’d be given. Unfortunately, I frequently screwed up the sales pitches for new menu items and I’d forget the daily specials. The longer I trained, the more I realized waiting might not be for me.

  But now I had a bet going with my sister that I couldn’t lose. So I tried my best. I worked as hard as I could to nail down the orders and the menu. I got marginally better, but I instantly felt a disconnect between me and the customers. They didn’t seem to like me very much and I wondered how well they’d tip me if it were for the handsome guy/girl I was shadowing that day.

  Eventually, the trainers seemed bummed to have me that day. Apparently, my presence alone was causing their tips to fall. I couldn’t help it though. I didn’t know why people didn’t like me. After all, I was giving it my all just like anyone else there.

  It took me longer than the other new hires to finish training. I had spent 3 weeks at the stupid Cheddar Palace making minimum wage at ten hours a week. Meanwhile, Brianna was hiring new babysitter after new babysitter. I had no idea how much she was making yet, but it had to be more than me.

  I tried to remind myself to be patient. Once I was on my own, I might do better. It was probably the idea of being watched and scrutinized that always made me fuck up orders. Yeah. Just wait until you’re on your own. You’ll make a killing.

  “How’s work?” asked Brianna on one of my days off. She was throwing a bag of things together to take to a babysitting gig.

  “Great. I’m making tons of money already,” I said, hoping I could just lie to her.

  “Oh yeah? Let’s see it.”

  “Uh,” I tried to think fast but she was already rolling her eyes.

  “Nice. Liar.”

  “Well, what about you then?”

  “I’ve got 5 girls all making $500 a week right now. I get 10% from each of them, so I’d say I’m doing pretty well.”

  “They’re letting you take 10%?”

  “That’s only $50. But I make $50 every week they work. Even while I sit on my ass at home and watch TV. And I’m planning on finding at least 15 more girls.”

  Fuck. $250 wasn’t that much but it was already more than I was making in a week. If she found the other girls she wanted, she’d be making $4000 a month without lifting a finger. I knew I would have some serious catching up to do if I was going to win the bet. The only plus side was that if I did win, a week’s worth of her income would be a lot more than I originally anticipated.

  “Well, don’t get your hopes up!” I yelled as she stepped through the front door. She paused for a moment a looked back at me with a smile. “I’m still going to win the bet,” I added.

  “Sure you are,” she said condescendingly. “Have fun on your day off.” She closed the door and I sank into the sofa. The only thing keeping my spirits up was the fact that the next time I worked I’d finally be on my own and making tips. I stretched my arms behind my head and exhaled. Yeah. I’ll win that bet in no time.

  But the next day was a disaster. Without the help of a trainer, I was completely lost. I bumped into every server at least once, sometimes twice. I spilled drinks and dropped orders. I forgot orders and brought payments to the wrong tables. I was only an hour into my shift and I already wanted it to end. Despite my disastrous efforts I still made a few tips, but they weren’t nearly the amount I needed to win the bet against Brianna. In fact, there were a lot of tables that didn’t tip at all.

  The kicker was when a manager had to have a talk with me. “Do you need a few more training days?” he asked.

  “No! I’m ready, I swear.”

  “You don’t seem like you’re ready. Look. Between you and me, we’re looking to cut a few people. We often over hire at the beginning of the summer so we can cut back to our best crew. If you don’t want to lose your job, you’re going to have to work harder.”

  “Are you serious?” But he only nodded with a disappointed look. I felt my cheeks heat up and my body tense. I almost felt like I could cry at the thought of losing this job. Then when I thought of losing the bet with my sister, I became furious. “I’ll do better. I promise,” I told him.

  He slapped my back and then returned to his office. I turned down the hall toward the busy and crowded restaurant. I can’t let myself lose this bet.

  But it didn’t matter. I couldn’t get the orders straight and I couldn’t keep from dropping everything. I felt like my limbs were jelly and the pressure of losing my job wasn’t helping. It was only a few shifts later when my manager gave me the bad news.

  “Sorry, Chris. I tried to give you a heads up. We’re going to have to let you go.”

  “No. No, you can’t do this. Please, I need this job.”

  “I’m really sorry, man. You’re just not cut out to be a waiter.”

  I felt defeated. I handed in my apron and collected my last measly paycheck. I barely made any tips and all the hard work I put in only earned me minimum wage. I could’ve worked anywhere for minimum wage and probably still had a job at least.

  I went home and sulked. I knew Brianna was going to rub it in my face. How could she possibly be more successful than me at something as stupid as babysitting? My only hope now was that she’d call off the bet.

  “No way,” she said when she found out I got fired. “Nope. I win. You have to cross-dress now.” She started laughing as she imagined me in some of her clothes.

  “Fuck, Brianna. Come on. Don’t kick me when I’m already down.”

  “Hey. You were the one with the snotty attitude about babysitting. We had a deal. Now it’s time for you to pay up.”

  “Look. I’m really sorry about that. I was actually going to ask…”

  She dropped her arms to her side as she waited for my question. “Yeah?”

  “Do you ever hire any guys to babysit?”

  “You want to babysit now?” She threw her head back and burst into a fit of laughter. “Sorry, bro. No guys allowed.”

  “Why not? That’s so sexist,” I challenged back.

  “It’s not sexist. It’s because guys are perverts that moms don’t trust them as much to watch their kids.”

  “That’s ridiculous.”

  “Maybe so. But that’s the way it is. Now if you want to cross-dress like we talked about, maybe I could get you a gig as a girl.” She laughed again as the image flashed in her head.

  “Ha, ha,” I replied sarcastically. But I couldn’t shake the suggestion from my head. The only reason I’d even consider it for two seconds was because I was desperate for money.

  “Well you still owe me,” she said. “In fact. If you don’t follow through on our bet I’m telling dad you flunked one of your classes.”

  “Shit, Brianna. How do you even know about that?”

  She walked to the foyer table and waved an envelope at me. “Your grades came in. I took the liberty of peaking for you.” I snatched the envelope from her hand and opened it up. She was right. I flunked one of my major classes.

  “This is illegal, you know. Opening someone else’s mail.”

  “You going to report me?” she challenged.

  “Maybe. You can’t seriously expect me to cross-dress.”

  “Hey. It’s your funeral. It’s that or I tell dad.”

  Shit. She was really trying to get back at me. “Fine,” I said with a sigh. “But no posting it to social media.”

  “I won’t post it to social media if you agree to be one of my babysitters,” she argued back.

  “What? No way. The whole point is that no one sees me cross-dress.”

  “No one you know will see you. Come on. It’ll be a good chance to make some cash. For both of us.”

  As much as I hated to admit it, she had a point. But what if someone I knew found out? What if one of the moms found out? There could be so many more consequences than just posting a one-time thing
on social media.

  Despite my brain telling me no a million times, my body was flooded with curiosity and pleasure at the thought. After all, I’d have my own little secret. And it would feel really good to fool all the biased moms that don’t want to hire a male babysitter.

  “I’ll do it,” I told her as we climbed the stairs.

  She turned back toward me and smiled. “I had a feeling you would.”

  Chapter 3

  I couldn’t believe what I had agreed to. I couldn’t believe I was being led to my sister’s bedroom to try on some of her outfits. I was about to cross-dress for the first time in my entire life. I’d always known guys from school who would cross-dress as a joke. Most people thought it was pretty funny. But this was a little more serious. This was me trying to fool people into actually believing I was a woman. I started to wonder if I should’ve just taken my sister’s offer to post everything on social media instead.

  But there was money to be made. Not just chump change, either, but serious money. If it worked out well enough, I might be able to drop out of school and be a full time babysitter. Of course, there would be no explaining that one to my parents. If I thought wanting to be a waiter was bad….

  I could hear my heart pounding as my sister opened the door to her bedroom and led me inside. She had the curtains drawn to protect her room from the hot, summer sun. The darkness, however, made everything feel more secretive which I liked and hated simultaneously. I started to feel dirty and ashamed, and I hadn’t even done anything yet.

  “So..what do I do?” I asked Brianna. I was desperate to break the silence. I was desperate to tear away from my punishment line of thinking. I kept reminding myself that this wasn’t permanent. I didn’t have to actually babysit as a woman if I didn’t want to. This afternoon was just an experiment. It was just a first time fling with women’s clothing. If I didn’t mind it, I could consider being one of Brianna’s sitters. And if I hated it, I’d be done. That would be it.