Shemales

Erotic tales of gender bending fun
Home | Archive

All Hallow's Eve

Date: 27.09.2008

Keywords: Eve, All, Hallow's,

Pages:
Prev 1 2 3 4 5 6

How I stopped it I don't know.

Tracy rode my cock for about five minutes before I started filling her with cum. The orgasm I felt was one of the best I ever had and I knew I came a bucket load. Just before I passed out from the intensity of it I thought I would be licking her for an hour to clean out the mess.

When I woke up I was still in Tracy's bed and the dildo was still embedded in my ass. Though it felt good the night before the dildo now felt uncomfortable. Tracy held me in her arms and my head rested on her firm bosom. I really didn't want to get up but I knew Maria would be in the house and it was my job to get Tracy's breakfast.

As gently as I could I eased out from under Tracy's arms so as not to wake her. Once I was able to get out of bed I realized I only had the nightie that Tracy put on me to wear. I found the panties that Tracy had thrown across the room and slipped them on.

As I walked out of Tracy's room I tiptoed through the house so Maria didn't hear me. I didn't want her to see me dressed in a nightie. I doubt she would understand any of this. I wasn't sure I understood any of it myself, but I wasn't ready to stop it either.

I almost made it to my bedroom when Maria came from around the corner and saw me. I watched as she covered her mouth to stifle a giggle before she said, "I was just going to wake you. Your breakfast is ready and Miss Tracy's will be ready soon."

My face became hot with embarrassment while I stuttered, "Um I um was going to get dressed I'll be out in a few minutes." I ducked into my bedroom but before I could close the door I heard Maria giggle outright.

Once in my bathroom I stripped off the nightie and worked the dildo out of my ass. It was actually quite painful coming out as the lube that Tracy had used was now dry. Once it was out I was surprised by how empty my bottom felt and how open my anus felt. I fear it would never close again.

I took a shower and washed my hair to take the curl out that Tracy had put in with the curling iron. As I stood in front of the mirror after my shower I saw the makeup that Tracy had put on me didn't come off with the shower. I had to scrub my face several times before I got most of it off. I then put on my male uniform before going into the kitchen for breakfast.

Maria handed me a plate of fruit and a cup of coffee before taking a seat across the table from me. When I reached for my fork I realized I still had the nail extensions on and my fingernails were still painted a brilliant red. Maria stirred her coffee for a few seconds before saying, "I'm sorry I laughed before. I didn't mean to embarrass you."

"It's okay, I must have looked pretty silly in that nightie," I told her.

Maria giggled again and said. "It wasn't what you were wearing that made me laugh it was the way you looked like a deer that was caught in someone's head lights. As far as the nightie goes you looked very cutie in it. Do you wear girl's nighties to bed every night?"

"No never. I mean last night was the first time. Miss Tracy talked me into it." I told her.

Maria giggled again and said, "Miss Tracy is very good at talking other people into things. Don't worry about me catching you in your girl clothes I understand boys like you like wearing girl's clothes. My bother is a sissy too and he always wears girl's clothes. He had breast implants and now lives as a woman all the time."

I was shocked the Maria was so open with me seeing we barely knew each other. Before I could say anything she got up and said, "You should hurry Miss Tracy will be wanting her breakfast shortly. She goes out every Tuesday and I'm sure today will be no different." It only took me a few minutes to eat and then I took the breakfast tray to Tracy's bedroom.

She was sitting up as if waiting for me when I came into the room. I noticed instantly that her nightgown was pulled up and her vagina was exposed. The look on her face told me she was upset about something.

As I placed the breakfast tray over her lap I said. "Good morning Miss Tracy is there something wrong this morning?"

Tracy pouted a little before she said. "I was hoping my girlfriend would be serving me breakfast this morning."

I knew she was talking about me as her girlfriend so I said. "I'm sorry Miss Tracy I didn't know you wanted me to wear the maid's uniform in front of Maria."

"Well Maria works for me too, so I really don't care what offends her. But I could see where that might embarrass you so don't do it until you feel comfortable with it. Now get my bath ready and my enema. I hope you did yourself this morning, if you didn't you can after I'm done," She told me as though I was dismissed.

As I went through the dressing room I picked up the clothes that were left on the floor before going into the bathroom. Once in the bathroom I started filling the tub and the enema bag. Once the bath was filled I went back helped Tracy out of bed and followed her into the bathroom. Once more I watched as she eased the enema nozzle into her rectum.

It was actually quite exciting to watch her slide the nozzle into herself knowing she enjoyed it so. After she pulled the nozzle free I filled it once more. This time the enema was for me. I filled myself twice before I was allowed to leave the bathroom.

Once the bed was stripped and remade and the bedroom was spotless I went back into the bathroom to help Tracy out of the tub so I could dry her off. I worked moisturizer into every inch of her skin before she left the bathroom so I could clean it.

When I came out of the bathroom Tracy was dressed in a gray business suit. The skirt of the suit was short. It stopped about four inches above her knees. She long honey colored hair was done up in a French braid. She wore a pair of black pumps that had a four-inch spike heel. I knew she would be going to the diner today. I also knew all the guys there would be drooling over her.

When Tracy saw I was in the bedroom she took me in her arms and said. "I have to go out today. You know what you have to do so I shouldn't have to stay here to keep an eye on you. Maria will be leaving early again today so you will have to tend to dinner again. I hope you don't mind. When I get home I hope my girlfriend will be here." She then kissed me on the cheek before strolling out of the bedroom.

After Tracy left I went into the living room and started cleaning. I wasn't about to change with Maria still here. I know she told me that she didn't mind but I just couldn't bring myself to do it around her.

About eleven o'clock Maria came into the living room and said. "Stevie honey Miss Tracy said I could leave early so I need to show you what to make for dinner and how to prepare it?"

I was surprised by what Maria was wearing. Earlier she was wearing a pair of white trousers and a white button down shirt. In fact she wore the same thing the day before. Now she was wearing a pair of shorts that were so short and tight I would have sworn they were painted on her. Her tank top left very little to the imagination. Her breast looked bigger than when she wore the button down shirt. Now they looked like they threaten to tear the tank top in half. Her breasts were bigger than Tracy's, though Tracy's tits seemed to fit her body better. Maria's legs were long thin and very tan. Her feet were nestled in a pair of white tennis shoes.

After I had gawked at Maria for a few seconds she came to me took my hand and said. "Obviously from the bulge in your pants you like girls so I guess you're not completely gay. Now come along I need to get going."

Maria pulled me along behind her as I said, "I'm not gay at all."

Maria giggled and said, "That's going to be hard to accept seeing what I saw you wearing earlier. I mean, any guy that runs around in a pretty pink nightie should be willing to play the girl's role in bed too. Maybe you're bisexual. That's okay too. I mean, I flip both ways on occasion though my boyfriend doesn't know about it."

Before I could say anything Maria and I walked into the kitchen. She started to explain what I needed to do for dinner. She also showed me where the wines were kept and which one I should sever with dinner.

Once she told me everything I needed to know she said, "I'm leaving now so you can change into something only a sissy would wear. Tomorrow don't be afraid to wear your maid's uniform when you come in for breakfast. I want to see how pretty you can be when you're all dolled up."

"How did you know about the maid's uniforms," I asked now completely confused by how she knew about them.

Maria took my hand and said, "When you were with Miss Tracy I went into your room. I didn't want to push the issue of you being a sissy like my brother unless you were really into it. After I saw all the pretty girl clothes in there I knew you were a sissy too. I know I shouldn't have invaded your privacy like that, I hope you forgive me. Now I really have to go. My boyfriend is taking me to the beach." Before I could say anything Maria was gone.

By the time Maria had left I was really confused. How could she think those clothes in the bedroom belonged to me. Surely she must have seen the other maids wear those uniforms before. Though they did look new I was sure she had seen them. I also wasn't happy about the fact that she was calling me a sissy. Okay I wore a nightie one night, that didn't make me into a sissy did it. And why did she think I was gay. Clothes didn't make someone gay did it? I mean girls wear men's clothes all the time that didn't make them lesbians.

Pages:
Prev 1 2 3 4 5 6

Keywords: Eve, All, Hallow's,

© 2007