Date: Thu, 17 Nov 2022 19:51:25 +0000 (UTC) From: Rachelle Naughty Subject: A Career Change Chapter 10 This is a work of fiction depicting sexual acts between consenting adults, aged eighteen and over. There are no similarities to anyone real or living, other than myself who is the main character, set in deep running fantasy. There are depictions of unprotected sex and smoking. I do not condone either, as each is an individual's choice. Constructive feedback welcome at rachellenaughty@yahoo.com. Also, support Nifty with a donation if you are able. A Career Change Chapter 10 The First Weekend The first weekend was boring until Saturday afternoon. I stayed in the apartment and ate all my meals there. I went to walk on the treadmill in the private, `girls' only gym. I had the place to myself. I guess the other `girls' are busy I thought. I need to ask how many girls there are. I practiced putting on makeup and walking in heels. I went to the salon and found it open on Saturday afternoon. Estelle was there. As I relaxed in the moisturizing tub, I thought, what would I be doing today on a Saturday, home alone. Dressing up in the panties and lingerie I have at home and entertaining someone who I don't know that well. That is exactly what you would be doing. But giving blowjobs every night after being fucked by a machine and practicing becoming as feminine as possible seems overwhelming. I am not built like a real woman, and I don't look like one. I dried off from the moisturizing and put a robe on. I saw Estelle stocking new nail polishes and cosmetics. I said thank you and wished her a nice weekend. She said in her broken English, "Rachelle, you so nice, you not like some of the other girls. They always complaining. I do your makeup, sit." "Thanks," Estelle I said, "but I don't think it will help, I am a man, not a girl. I don't know why I am here." "I make you super beautiful, you wait," as she pulled a bunch of products from the shelves and set it all out. She put concealer and foundation on, followed by eyeshadow, eyebrows, eye liner, blush, and lipstick. She spent a long time on the cheeks. She then got a fresh style wig. A shoulder length, auburn style that was very sexy. When she turned the chair, I didn't recognize myself. Shit, I thought to myself. Look at how my cheek bones look. I still had a squarish man face, but I was looking far more femme than I had felt. "You wait I have surprise for you," she said. She disappeared into Carla's office and came back with a box. "Carla order this for you," she said as she took out of the box a chest plate with two large breast forms. It was made of silicone, and it went over my head and covered my upper back and torso. I squeezed one of the breasts and it was very lifelike. I had looked at these online before and they are expensive. Estelle doused me in baby powder and held it up so I could put my arms and head through. She pulled it down over my chest. "Too tight?" "No, it feels good," I replied. "Come with me," she said as I followed her to the changing area while she went in the back to get clothes. She came out with a pink push up bra, pink thigh highs and garter belt, pink thong panties, a plum purple skirt, and pastel pink blouse. "Ok we dress you." She helped me get everything on and went to get shoes. Pink four-inch heel open toe sandals. I put them on and stood up. I looked in the mirror. The breasts were huge with the push bra, and I had actual cleavage. The skirt was short, and you can see the garter belt hooks. I bent forward slightly, and you could see my panties. That is sexy I thought. "You look beautiful." she said, "Go have fun." I thanked her immensely and gave her a hug. I left the salon and thought where can I go? I could tell scheduling I will work the booths. Or I could get in my car and go for a ride. That wasn't happening. Who was I kidding, I thought to myself. I went back to my apartment. All dressed up and nowhere to go I thought. I am too shy to go out in the world looking like Rachelle. It was five o'clock and I was about to take off my makeup and write a note to Carla telling her I left when there was a knock on the door. I looked through the peephole to see Mr. Degrassi standing there. He wants that favor I thought. And then I thought ok, I am going to pay him back right now as I opened the door. "Hello, Mr. Degrassi." "Rachelle! You look amazing." As his jaw dropped. He was speechless. "Thank you, Sir, I am work in progress. Please come in," I said as he slowly walked into the living area looking at me as I closed the door behind him. "Let me look at you," he said. I turned around for him. "I am getting there," I said, "but I think I may leave tonight or tomorrow." "Oh no," he said. "I just don't know about this. I have given more blowjobs in three days than I want to admit." "Did you enjoy that?" "Well yes, I did actually. I was soaked in cum from one man and that was amazing, but I just don't know anymore. Everything in my life has changed so quickly." My eyes started to well up. I was very emotional. He took my hand, "Call me Joseph please. I was done with work and came up here today to collect that favor from you, but I don't want to do that if you are upset," he said. "I appreciate that." "If you really want to be a girl, you must get past the mindset that you may not look completely feminine. You look amazing right now, but that is just my opinion. You are still a guy underneath and that won't change. If you decide to stay, and only you can make that decision, I will come back another time, but it isn't important now." He kissed the back of my hand and started to walk towards the door. "No don't go. Please stay. Can you stay?" I asked "I can." "Have a seat. Help yourself, the bar is stocked well," I said. "Thank you," he said as he fixed himself a drink. "Pour me a glass of wine please," I asked. He came over and sat on the couch. Putting the wine down on the table, "A glass of wine for Ms. Rachelle." He had straight bourbon. He pulled out a cigar from his pocket humidor and took to sizing it and lighting it. "You don't mind do you," he asked. "Not at all. I will join you," as I grabbed my pink cigarette case. We sat and talked for an hour or so. We told each other of our divorces and problems with the ex's. By the time our first drinks were empty we both were quiet. "Dinner should be here soon," I said. "I will go then." "No please don't," I asked of him. Putting my hand on his leg. "I would like it if you could stay. I will order an extra plate, though I have to warn you, Carla has me on a diet, but so far the kitchen has sent some really delicious meals." I called the kitchen and asked for two servings as I had company. About a half hour later there was a knock on the door. The same gentleman who delivered my meal the first day was there. "Room service for Ms. Rachelle. You look beautiful tonight Ms. Rachelle," he said. I thanked him, tipped him and he left. "Let's eat," I said to Joseph. We chatted some more over dinner, which was baked fish and not salad, and each of us had a glass of wine. He was single, has been working here for twenty years, he is sixty-one years old, has two kids both are grown up. His wife found out he was fucking someone at work about five years ago. When she found out it was one of the T-girls, she filed for divorce. Before that she was willing to let the transgression go but it seemed the thought of her husband fucking a crossdresser or transgendered person was too much. I was feeling the second glass of wine and knew I had to keep it together so I could give Joseph his favor. Joseph was a stocky guy, about my height, but the heels made me slightly taller. He had bit of a belly which I like on certain men. His hair was salt and pepper, mostly salt and he had a goatee that had grayed, though he said he usually just has a mustache or is clean shaven. He dressed nicely and overall seemed like a decent guy. "I am going to go use the bathroom," I announced. I brushed my teeth, and checked my makeup (oh my God am I really doing this I thought). I emerged to the living area, "Can you stay a little longer or do you need to leave?" "I can stay." Let's sit in the living room. I lit up another cigarette. "This is becoming a habit, I need to cut back or quit," I said. He pulled another cigar out, smaller than the first one. It had a pleasant aroma. I told him how I used to smoke cigars and masturbate in my garage back when I was married. I miss them sometimes, but I gave it up when I was divorced, trying to be healthy and all that. "And now look at me, smoking Virginia Slims," I said, laughing my way to a nervous silence. "I should quit these too, but I love them too much. I only indulge on the weekend. Plus, with the employee discount I get them cheap." "Do you want to kiss me, Joseph?" I blurted out. He looked at me with a surprised look but also a yes, I want to kiss you bitch look. I stubbed out my cigarette and went over to him. I straddled his legs, leaning into him, the fake breasts pressed firm against his chest. I moved in and planted my lips squarely on this. His goatee tickled me. Our tongues met and melted as his tongue forcefully penetrated my mouth. I know the wine was talking a little bit, but I wanted to have sex with him, not just return the favor with a blowjob. I dropped to my knees and started to take his shoes off, then his pants. He sat there puffing his cigar, with a smile. Before I knew it his cock was in my mouth as he unbuttoned his shirt. He had a graying, hairy chest which drives me crazy. For a stocky man, he still had a good-sized six-inch cock. Without his belly he must be eight inches, but who cares, he was rock hard. I tongued his cock head and ran my tongue up and down the shaft while he puffed his stogie. I was getting a little moan out of him. "Let's go to the bedroom," I said to him, getting up, grabbing his hand, and leading him off the couch. He trailed off behind me, releasing my hand. I was at the bottom of the bed, and I looked back over my shoulder at him. He was standing there taking in the view as I bent forward ever so slightly to reveal my thong panties. "Come and get it Daddy" I said to him. With that he came up behind me, grabbed my ass and pulled my panties down. He sunk his head into my pussy and gave it good tongue lashing. God that felt wonderful. I hadn't had that done to me in a long time. I undid the skirt and let it fall to the floor. My panties were around my ankles, and I kicked those off. He stood up and I turned partially around, and we kissed again. "Fuck me" I whispered in his ear "and cum deep inside me." He pushed me forward, bending me over the foot board. He took some spit from his mouth and lubed his cock. He pushed ever so gently against my pussy until I felt it open, and he slid all the way in. "God yes!" I yelled out, "Fuck me, Daddy!" Joseph thrust his hips in and out pounding my pussy. It didn't take him long until he shot his load deep inside me. "I needed that," he said. I needed that as well. We were both exhausted. We crawled onto the bed. I took the heels and blouse off and collapsed to sleep laying my head on his chest. How I love a furry chest to snuggle up to, I thought as I drifted off to sleep.