Chris remembers his first time as Chrissy

This is a much larger story broken into chapters. Please read in order, as it may not make sense if you don't. I'd be glad for any feedback you may have.


Her birthday was a couple days later, on Saturday, so we had the day free. We woke up in the late morning. We showered together, but without having sex, which we usually did if we were in the shower together. In fact she wouldn't even let me touch myself. She washed me. When we were done she told me to sit on the bed for a minute while she got everything ready. "Now, we are going to do this." Sandra was talking in a comforting voice, trying to put me at ease. "I'm going to be in charge, and you will do as I say. That's how a good maid should act. I might do things we haven't done before. If you really want to stop then say so and I will, but you know that I would never do anything to hurt you, or that I thought you wouldn't end up enjoying. So please try to go with it, even if it shocks you."

"I will."

Sandra went to the closet and got out my outfit, with the stockings and shoes. She put the stockings on me; they were thigh highs. Then handed me a light blue thong, saying it was the most girly one I had. I think I heard her mumble something about getting me others. I stood up and put it on, liking the feel of my hands sliding along the sheer material covering my legs. I turned around for her to see, and she slapped my butt playfully. Next came the costume. I stepped into it and pulled it up, slipping my arms into the little sleeves. Sandra had me turn around again so she could zip it up. There was a little white lace collar that she put around my throat. Her fingers trailed the lace edges of the top, along my chest. Then she knelt down. I hadn't noticed the little garter straps that are part of the costume, but she was connecting them to my stockings. She ran her hands over my legs.

"Sit," she commanded, and I sat back down. She lifted my feet, one at a time, and put my shoes on. She was smiling widely, clearly enjoying this. I have to admit that I was too.

"Now come in here," Sandra said, wiggling her bare butt at me as she turned and walked into the bathroom. I followed her. She said, "Sit there," pointing at the little stool that we have in there. She picked up her reddest lipstick off the counter.

"What are you doing," I asked. Make-up wasn't something I had thought about.

She looked at me. "You need some lipstick, and eye shadow, maybe a little mascara. You are already in a tiny little skirt, how is this any worse."

I let her put it on me, thinking that it really wasn't any worse. I might as well go the whole way, it was just for her. It was strange feeling her put it on me, and she wouldn't let me look in the mirror.

"I'll be right back, DON'T look in the mirror, I'm not finished with you yet." Sandra left the bathroom for a minute. "Close your eyes hun," I heard from the bedroom. I did, wondering what she had planned. I felt hair brushing my face, then something on my head. It was moved around a bit, then she told me to look in the mirror.

I couldn't believe it. She had put a dark red wig on me; it hung a little past my shoulders. I kept looking, shocked by what I saw. I looked kinda feminine, not that I could pass for a woman, but it wasn't totally horrible. She was standing behind me, hands on my shoulders.

"You are such a sexy girl, don't you think so Chrissy?"

"Chrissy," I whispered, still a little stunned. "Why are you calling me that hun?"

"Well," she pointed at the mirror, "I can't just call someone who looks like that Chris, now can I." It wasn't really a question, more her making sure I knew how she wanted it to be.

We went into the bedroom, and she told me to go make breakfast like a good maid while she got dressed. I had been hoping to have sex but I did what she told me to. This was her birthday present after all.

I went out to the kitchen, fairly well in the heels. The feeling of the stockings on my legs as they rubbed past one another was great. I checked the large mirror in the living room. Standing up the skirt went low enough to cover things, but barely. If I bent forward just a little then you could see light blue fabric going up between my cheeks. It turned me on to know that I could flash my butt so easily; I like the reactions that it gets in tight pants. I thought that it was lucky the skirt flared out a little, otherwise it would be obvious that I was getting hard.

When I got to the kitchen I decided to make some eggs and potatoes. Sandra loved that as a big breakfast. It didn't take long, and just as I was finishing she walked into the room. She was wearing a little black dress that I liked. It was low cut in front, showing her 34B breasts well, and the skirt was only about halfway down her thighs. What she had on under it I hadn't seen before. There was red lace showing above the top of her dress. At the edge of the skirt there was about an inch of skin showing before the lacy tops of red stockings, and I could see the garter straps holding them up. She had on black heels over these, about three and a half inches high. Those would have made her almost as tall as me, 5'10", if I didn't have heels on too.

She took a seat at the table, and I put her plate in front of her, the silverware already there. I turned to get mine, and she grabbed my wrist. "Shouldn't the maid curtsy before she leaves?" She was grinning wide.

I did my best to curtsy, almost falling down. She giggled. I got my food and sat across the table from Sandra. I looked at her, smiling myself because she was obviously enjoying herself. I noticed that I could see her nipples poking against the dress very well. I usually couldn't when she wore that dress and a bra, but she definitely had something on under it. I was getting harder.

"Breakfast is wonderful Chrissy, I just might have to keep you around more." She winked as she said that, making me wonder exactly what she meant. I didn't ask, afraid that I had an idea already.

Not much was said as we ate, but looks kept going back and forth. She kept running her fingers along the lace above her dress, which made me unconsciously do the same. She smiled when she saw that. We finished and I go up to clear the table. Sandra slid back from the table some and crossed her legs, making the tops of her stockings even more obvious. As I took her plate and turned, she tossed her fork in front of me on the floor.

"Oops," she tittered, acting like it was an accident. "Chrissy honey, could you pick that up for me." I bent at the waist, forgetting how that would expose my bottom, when I felt her pinch my butt cheek. I jumped a little, almost dropping the plate. When I looked over my shoulder she was looking away, playing innocent, but not trying very hard. Once everything was cleaned up she led me to the living room.

She sat me on the couch, kneeling in front of me. "You are doing so well so far Chrissy girl, I thought I could give you a reward. With that she lifted my skirt, poking at the fabric covering my semi-hard dick. "Looks like my girl is excited, I think I'll have to do something about that." Sandra spread my legs and got close. Her lips rubbed against my thong and the hard bulge that was beneath it. It was such an excruciating tease. I reached down to pull my thong off and hurry things along. She slapped my hand away, giving me a look that said if I did anything she didn't tell me to then I would regret it. I laid back and let her do what she would, hoping she wouldn't take too long. The tight cloth was painful with me so excited, and her teasing was only making it worse. She finally pulled it aside, freeing my cock. She couldn't pull it down without removing my garter straps, and I don't think that idea even occurred to her. She was still teasing, giving me little pecks of her lips on my shaft and my balls. Her hands were rubbing my covered legs. After a few minutes of this I thought I might explode whether she went farther or not. That's when she opened her mouth and, without using her hands, took me into her. She sucked hard and started moving up and down fast. I didn't last long after all the teasing, but the feelings were some of the best ever. I was covered with sweat and breathing hard.

When I had finished she pulled off of my cock and smiled up at me, looking satisfied. With her hands on my knees, she lifted herself up to my face. I noticed a little cum dribbling from her lips. She kissed me quickly, pushing her tongue into my mouth right away. That wasn't all she pushed in, I could taste my cum. This was new, and a total surprise. She had always kissed me after, but never before she swallowed. The taste usually didn't bother me, but this was much stronger. She pushed me so my head was tipped up and lifted her lips from mine, letting cum dribble into my open mouth. Her finger made sure I didn't try to close it. The she kissed me quickly, getting the last of it from her lips to mine.

"Swallow," she commanded as she backed up. I did, feeling it slide down my throat. "Now that's a good little slut maid. I knew you would work out Chrissy," she said, sounding like I was someone she had hired and then fooled around with. I guessed that that was part of her game, the idea of taking advantage of the hired help.

"Your lipstick is all smeared Chrissy, let's go fix it." I followed her into the bathroom, where she kissed me deeply, running her hands under my skirt to my bare ass. Then she took care of fixing my make-up. "Now pay attention Chrissy, you will have to learn to do this yourself." Now it was clear that it wasn't just for the day, she would want to do this again. I wondered how often as she held me, putting the lipstick on my face. "There, now back to the living room with you." As I left she smacked my bottom, hard.
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