Chrissy Serves

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.

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Sandra lay down next to me, breathing fast, teasing my cock as it started to soften. I turned toward her and kissed her. She brought both of her hands to my face and returned my kiss, sucking on my tongue. Then she pulled away and lay back.

"You are always so good for me when I'm on top, you know that Chris," she said, a little laugh in her voice.

"I like it just as much as you babe." I replied.

Sandra leaned back, resting her head on her hand. "An old friend of mine from college is going to be in town sometime this weekend. I thought I might invite her over for a while, for dinner or something. That sound ok to you," She asked me. "Sounds great. When is she going to be here?" I haven't met any of Sandra's friends from college because her school was pretty far from here. "Did you wanna go out or have dinner here?"

"Probably just stay home, you can cook up something good." She seems to think I'm some kind of master chef, or at least she likes my cooking.

Sandra reached over and pinched my nipple. "One other thing I was thinking about. I think I want to play with Chrissy tomorrow hun."

I looked over and saw the mischievous smile on her face. "Anything for you." I said and kissed her again briefly.

As we lay back to go to sleep I was thinking about being Chrissy. It wasn't that I went out dressed as a girl. We just liked to play sometimes that I would serve Sandra, and she puts me in a French maid outfit while I do it. And she calls me Chrissy, like a girl. It is fun and she really enjoys it. I drifted off to sleep thinking about playing her maid for a day this weekend.

I woke up around eleven. Sandra was already up and not in the room. She usually gets up earlier than I do on the weekends. I sat up and pushed the blanket off to the side, looking around the room. On the chair I saw my clothes for the day; she had laid them out for me. I got up and walked over to the chair. I was about half-hard, like I always am first thing in the morning. I thought about playing with it, but decided not to. I would be getting off enough over the course of the day playing maid for Sandra. I hoped.

I walked into the bathroom, grabbing a towel on the way. I relieved myself and took a quick shower. After drying off I sat on the bed for a few minutes, enjoying the feel of the air on my bare skin. I don't have any body hair, we both wax. It hurts, but a little pain once a month is better than the raw skin from shaving every other day. I went over to the chair to get dressed, wanting to greet Sandra already in my costume. I was the usual maid outfit, black with white trim, skirt that doesn't quite cover the butt. The top was tailored for a man though, so it didn't look loose with the lack of breasts. She had put out the white thigh high stockings and my shoes. For underwear there was my red silk thong.

Looking at the outfit, I started thinking about my first time as Chrissy. It was for Sandra's birthday. We were at the adult book and toy store, a couple days before her birthday, looking around to buy her a new outfit. She likes having sexy underwear, teddies and such. She wears them around the house just to wear them sometimes. Probably as a way of teasing me too. I heard her giggling and went over to see what she was looking at. She held up the maid outfit and looked at me, smiling.

"It looks a bit big for you hun, maybe they have one that will fit," I told her. It looked like a cute costume, but the maid was never a big fantasy for me, so I wasn't too excited.

Sandra laughed more. After looking at me for a minute, she got close and whispered in my ear, "It would fit you Chris." She laughed again as she backed up again.

"You can't be serious," I said in shock. She had never given me any indication that she would want me to dress up like that, not even asking me to try on her panties. I probably would do that for her, without much thought, but this was taking things a bit farther.

"It's not like I want you to go out in it hun," she told me, smiling. "It would just be at home, for us. I think it would be fun." She moved close again, holding the outfit between us as she pressed against me. She whispered, "We could make a game of it, you could be my maid for the day. Take care of all my needs." At that she kissed me. "Just for my birthday," she pleaded.

I've always had trouble saying no to her about things like this, which has led to some rather interesting sex. I smiled, and she grabbed my wrist and started pulling me toward the fitting rooms. She pretty much had to push me into it when we got there. I slowly undressed to try it on, stripped down to just my thong. That's something else that she started, although I prefer them to any other underwear now. I put it on, having a little trouble with the zipper in the back. Sandra was right; it fit me fine. "It fits, I'll---"

"Don't come out," she interrupted before I could tell her I had no plans of doing so. I wasn't going to let anyone who might be in the store see me like this. "I don't want to see you in it till my birthday." I was relieved to hear that.

I changed back into my jeans and shirt, glad to be dressed again. I sat there for a minute or two, deciding if I really wanted to do this or not. Finally I thought, why not, it's just us. When I stepped out of the fitting room, Sandra was walking back from the front of the store. I didn't think much of it, seeing that she has a pair of white stockings in her hand. Just more for the outfit she was putting me into for her amusement.

I started walking back to the clothes racks, still wanting to get something for her to wear. "What are you doing hun," she asked. I told her and she replied, "Don't worry about it; I got myself something while you were in the fitting room. I want to surprise you with it."

"OK."

We went to the counter and paid for my costume. The woman at the counter, an older lady grinned at me as we did it. I blushed, and she giggled and winked at me. We left the store, Sandra putting our purchase in the trunk so I wouldn't see what she had already bought.

She drove us to a small shoe store, cheap place. "Why are we here," I asked.

"You need shoes. You can't wear any of the ones that you have with something like that."

I was mortified, it was one thing to try on and buy something like that at the porn store. They see all kinds of stuff, I'm sure most stranger than that. But this was a normal store and she wanted me to try on women's shoes. It must have been obvious what I was thinking, because she leaned over and hugged me.

"Don't worry. We don't go here usually and it's a bit away from our place. No one will know you." She hugged me, running one of her hands to my butt and squeezing it. "I have such a great guy," she said as she pulled me toward the store.

We weren't in the shoe store long. She picked out a pair of white pumps with a 2" heel for me to wear. Nothing fancy, if not for the heel they would have looked normal with a real maid's uniform. We did have to have the clerk, a cute girl who looked barely 18, go into the back to find them in my size. She was giving us strange looks the whole time.

When we got home, Sandra pulled into the garage. As we were getting out she said, "Put the shoes on, you need to practice walking in heels." I did, why object now. It took me a minute, but I could walk ok if I thought about what I was doing. She got the stuff out of the trunk, still not wanting me to see what she had bought when I wasn't looking. "Chris, come over here, I need your help with something."

I walked over to her as she closed the trunk. She bent over it, lifting up her skirt. "Thinking about you in this outfit has me all wet babe, can you take care of it for me." I could see the damp spot on her light blue panties. "Don't fool around; just take me quick, right here."

I usually like foreplay, but this was definitely a time to be quick. I walked over to close the garage door, but Sandra stopped me. "No, leave it open," she said seductively. We had had sex in the back yard before, but with the fence there was no chance of being spotted there. This was different, and a turn on. I walked up behind her, running my hands over her round bottom as I pulled her panties down. I opened my pants and took out my cock, already very hard, without pulling then down. I rubbed the head against her wet lips a few times, listening to her whine softly. She does that when she is very hot, almost ready to cum, and I tease her. I pushed in slowly and she gasped, she must really be close. She was warm and wet around me. I began backing out. When almost out I thrust back in fast, until my hips hit her bottom. She moaned as I did it again and again, out slowly, then in hard. She was cumming in a short time, a high-pitched hum coming from her mouth as she tried to be quiet. I came just after her, shooting inside her as I leaned against her back, kissing her neck.

I pulled out, pulling her panties back up and righting her skirt. She turned, and before I could put myself back in my pants, she knelt down and took me in her mouth. She just sucked me for a second or two, and then put it away. She stood up and kissed me deeply. Sandra grabbed the bags and we went inside, me still a little wobbly in my heels.