A Mistress to Obey

I woke up when she whipped the cover off the cage. I had been able to curl up enough to sleep on my side but when I tried to move I was very stiff. She opened the cage door and I backed out. She told me to go take a nice long shower and that my clothes would be on the bed when I finish. She was wearing a pair of tan slacks and a yellow blouse and looked like she had been up for a while and had already cleaned up.

I went and got into the shower. The hot water was intoxicating and I took a long shower. Still wasn't used to the smoothness of my body. It did feel good but it just was so different. This reminded me about the bottle of hair remover Mark had given me and knew I would be using it. I soaped up my cock and it too felt weird without pubes and the hair on my balls. I had hoped it would make my cock look bigger but whenever I look it just makes me feel more like a little boy. I finally force myself out of the shower and find a note with an arrow pointing at a toothbrush and tooth paste. It read, "For you sissyboy."

While brushing my teeth I can't stop thinking about what I have got myself into. If I want to put a stop to it, can I or will they use the pictures and videos against me. Remembering what Mark said about Mistress Sherrie outing a couple boys. Did she just do it because they wanted out? I'm scared what the answer might be. Maybe it's all a mind fuck where they want to scare you to enhance the experience but would never expose you for real. Maybe, but what if it isn't like that at all. What if I really have to do anything she says or she will make things public. Damn, damn. I wanted this experience but wanted some control of things and feel like everything is out of my control.

I finally get it together enough to come back to the bedroom. On the bed is a pair of white silky bikini panties, a baby blue sundress and a pair of white sandals with two inch block heels and ankle straps. I just look at it and realize she isn't taking a break from this and wants to continue making me do as she wishes. I walk over and get dressed and move over to the full length mirror. I look at myself and realize how ridiculous I look. I look like a man in a dress and heels and I can't do anything about it. I really just wanted to get together for a few hours and play nasty, not all this. I can't help thinking if I go in there and bitch about it, it will probably make it worse. I really don't want to be punished anymore.

I'm surprised by the door opening and you walking in and coming up behind me.

'Morning sissyboy.'

'Good morning Mistress.'

'Do you feel better now?

'Yes the shower felt so good. May I ask you something without making you mad?'

'Yes, go ahead Billie.'

'Could I just wear my regular clothes Mistress? I feel so silly and I look ridiculous in a dress like this.'

'My, my, you are a little whiner, aren't you? I didn't realize you had any regular clothes over here. I didn't think you would probably want to wear your sissy fag outfit this early in the morning.'

This reminds me that my regular clothes are over at Mistress Anne's. Fuck, fuck, how does this keep getting worse and worse? 'I forgot Mistress, I'm sorry. I forgot that there isn't any over here. Do you have anything more masculine that I could wear long enough to go get some things?'

'No, not really. You might keep women's clothes at your place but I don't feel the need to keep men's clothes here. I'm not like you at all.'

'I don't have women's clothes at my place Mistress. Dressing up like this and the other things were all your idea Mistress.'

'Other things, what other things?'

'You know what I mean Mistress. You know the stuff Mistress Anne made me do last night.'

'Oh you mean, you dressing up fem and sucking cock. I just love those pictures of you, why don't we go look at them again.'

'Please Mistress. I don't know if I can do this. It's so much more than I was expecting and I'm really not gay.'

'Look at yourself in the mirror. Just look. I talked to Mark this morning. He was very impressed with you. He told me that you told him you liked dressing up for men and couldn't wait till you had some dresses to wear for men. He said you told him you wished you were a girl and that you were a faggot. Did he lie to me Billie?'

I know that I did say all those things but I said them because he told me too. I know, at times I did enjoy what was happening but I can't be like that. The thought of people knowing I'm gay, and not just gay, but like to dress up like a girl too would be too much to handle. Head down, I answer, 'No Mistress, he didn't lie.'

'You liked it with him didn't you?' she asks as her hand moves under the back of my sundress and caresses my pant covered ass lightly. It feels so good. I can feel her fingernails scratching lightly over my panties and I can't help but press back a little. 'You liked being his sissy, didn't you Billie?'

'At the time, it wasn't so bad. But Mistress, I'm not gay, really. Please don't take me there. I don't know if I could handle it, being gay, you know. I really like women. I will try hard to please you. I will do whatever I can to make sure I'm a good boy for you. Please.'

'You can bullshit yourself all you want boy. I will ask you one more time and I want a straight answer. You lie to me and I will know. Now did you enjoy being Mark's sissyboy?'

Head down, tears in my eyes. 'Yes Mistress, I did.'

She moves over and sits down on the bed. 'Come here Billie.'

I go over to her and she points to the floor and I kneel in front of her submissively, head down, feeling so out of control. She pulls my head to her lap and lets me rest my head there as she talks to me.

'I am going to turn you into a sissy fagboy Billie. I enjoy taking boys like you and turning them into good little sissies. You would not believe the feeling I get when I watch a boy like you kneel in front of a man and take his cock into your mouth and suck it like it's the most important thing in the world. It makes me all warm and wet inside sweetie. The best is when the sissy begs to be fucked. Her first cock has to be big and she must beg for it. She must want it so bad she will do most anything for it. She will beg me to punish her and help her become the sissy slut she knows she is. I can't wait to see you like that. Dressed up nice and pretty and giving your pussy to a man.'

Tears running from my eyes as I listen to her. 'Please Mistress, please just let me go. I'm sorry, I can't do this.' I can't keep from sobbing, not realizing that the pills (double dose of feminine hormones) I took last night and this morning might be having any effect on me.

'You can do it Billie. You will do it for me. I will help you with this and I'm sure you will make a good little sissy. I will help you understand that it's better to do as told, even if it something you might not want to do, then to know that you must be failing with your training and that I will just have to make you understand better. Do you understand?'

Sob, sob, 'I think so. I do what you say or you punish me or expose me,' I say quietly not looking up at her.

'Exactly, sweetie. I'm so glad you understand. Now enough of this, I have breakfast waiting for you. I want you to go out and get the paper. It's on the sidewalk out front.'

Realizing she wants me to go outside like this and know I better do it after the little speech she just gave me. I go to the front door, look around and don't see anyone. I get to the street and pick up the paper and start back when I see a man in the house next door standing at his door watching me. He just stares till I look down and hurry back into the house.

'Doesn't the wind feel nice on your legs sweetie?'

'Yes I guess so but one of your neighbors saw me.'

'Next house to the left? Older guy?'

'Yes.'

'That's Mr. Lyons. He likes sissyboys. I have fixed him up a couple times. I know he keeps a close watch on my house, the pervert. He has quite a setup in his basement. He invited me and one of my sissy boys over to see it. I left the sissy boy there but left with $200. He's rather strange. He is all lovey dovey with young sissy boys but with older boys, I think he thinks they should have grown out of it and now they are just perverted boys that need a man like him to set them straight,' you say laughing softly. 'He sets them anything but straight. They do learn obedience but his methods differ from mine.'

Damn, what is with this neighborhood? Thinking about the way he looked at me. It made me feel like I'm prey. Thinking this is a man I probably want to stay away from.

'I watched you too and I have to say I was disappointed. You don't seem to understand that when you are with me, I expect you to act like a sissyboy.'

'I'm sorry Mistress, I didn't know you wanted me to behave like that.'

'It's ok sweetie, I told you I would help you. A trip to the playroom will be necessary after breakfast, now sit down.'

Oh god, I know what that means. I look down and all that there is a grapefruit. She starts telling me she is going to help me with my diet and that corset training will start soon. I eat as I listen to her as she talks about my diet. The phone rings and when she answers it doesn't take long till I realize she is talking to Mistress Anne.

'Hello Anne, I can't wait to talk to you,' she says then pauses and listens. 'Oh Anne, I couldn't believe the outfit you had him in, it was perfect.' Pauses. 'Yes, I couldn't believe how it made me feel,' laughs lightly. 'I got so wet I couldn't believe it. Listen, he even stopped on the way to my place at a convenience store and went in like that. I think he wanted guys to see him like that. Can you believe it?'

I just sit there head down as they talk about me like I'm not even there. She made it sound like it went into the store because I wanted to. She listens to Anne for quite a while.

'I guess you were right about him Anne. Mark said he loved the way the boy protested but couldn't get enough once he got a taste. You won't believe how he came. He was sitting on Mark's lap with Mark rubbing his cock through the panties and he came in them. He was such a sticky mess when he got home.' Listening. 'I know, that is just so queer,' she says laughing softly.

'Oh, he's right here beside me. Anne wants me to tell you that you were a good little whore last night.' Listening. 'He sitting here in a sundress and panties,' laughing, 'just can't keep the bitch out of a dress. Ok, keep in touch,' and she hangs up. 'She really wants to spend some serious time with you. If you behave I won't let her have you.'

Hearing them talk about me like that is demeaning but I can't keep the thoughts away that this is what I have fantasized about. It's just the fact that I have no control that makes the situation uncomfortable. How far might they push things? And that doesn't even start to deal with the fact that I don't think I could handle what Mistress Anne might do to me. The thought of that happening is something I can't allow to happen. I better keep Mistress pleased with me. She looks over at me.

'Do you like your dress Billie?'

Head down, 'Yes Mistress, it's very nice.'

'It's pretty Billie. Tell me you love your pretty dress.'

I can feel my face getting red. 'I love my pretty dress.'

'I know you can do better than that sweetie. You do want to please me don't you? It's ok to sound fem. Don't you just love the ways really gay boys talk, I know I do. Think about last night, sitting on a man's lap. I want to hear that girl tell me how she loves her dress.'

I know I must do this so I tilt my head to the side slightly bringing a finger to my lip as I say 'Oh Mistress, I just love this dress. The way the wind felt on my legs and under my dress was so fabulous.' I tried to sound really feminine but think it probably just sounded gay.

'You are going to be a good girl, aren't you Billie?'

She lifts my chin up making me look at her. 'Yes Mistress.'

'We still need to deal with your earlier bad behavior though Billie. I think I mentioned visiting the playroom, didn't I?'

'Yes Mistress but I hoped I have pleased you since then Mistress.'

'You have sweetie but things must be dealt with. Misbehavior can not be tolerated. Now tell me why we must go to the playroom.'

Head down, so embarrassing, 'Because I didn't act like a sissy Mistress.'

'I had told you what I expected of you, didn't i?'

'Yes Mistress, I just didn't understand everything. I didn't know you wanted me to act that way all the time.'

'Is that my fault that you didn't understand Billie?'

Quietly, 'No Mistress.'

'Whose fault was it?

'It was my fault Mistress, I'm sorry.'

'What do you think I should do since you obviously didn't do what I wanted even though you knew what was expected of you. Do you like disobeying me just to piss me off? DO YOU??'

Her demeanor did an abrupt one-eighty. I knew I was in trouble. 'No Mistress, I'm trying to please you.'

'Well, you are fucking failing!! What do you think I should do?'

'You should punish me Mistress to help me learn how to behave properly.'

'I agree, playroom now.'

Thankfully, I think to walk like a flamer, swishing my little hips. Can feel her right behind me. I have to admit it was rather intimidating and I was kind of scared. The way she was instantly mad and the look on her face left no doubt that she had plans for me.

'Stand there, face the mirror.'

I do as she says and when I look at myself in a dress and heels, it hits me again what I have got myself into and I don't have a clue on how I can make this stop.

'Tell me what you see Billie.'

'I see a man in a dress and heels. I think he looks ridiculous.'

'I didn't ask you what you thought. I asked you what you saw. Did you really see a man? I didn't. I mean, would a man wear a dress around all the time?'

'No Mistress.'

'Look again. Take a good long look and tell me what you see Billie.'

I look in the mirror. I can see her behind me. She is slipping on a pair of black leather gloves. Trying to sound really fem, 'I see a sissy in a dress and heels. She looks like she loves being in a dress and wants to look pretty for her Mistress.'

'Much better, maybe you aren't such a stupid girl after all. Are you a stupid little girl?'

'No Mistress, I don't think I'm stupid.'

'Then why do I have to tell you things twice. Do you just not pay attention when I talk to you? IS THAT IT???'

'No Mistress, I really am trying.'

'Lift up your dress.'

I lift it up exposing my panties.

'Look at yourself sissyboy. Are you trying hard enough?'

I feel like I'm on the verge of tears. 'No Mistress.'

'I agree, don't you fucking move.'

She starts spanking me with her leather gloved hand. It really stings and it was all I could do to stand there. She just kept spanking me till I was in tears. My ass felt like it was on fire.

'Look at yourself sissyboy. Look at the little fucking crybaby. Now I want you to ask me to pull your panties down and spank you harder.'

Oh god, my ass was on fire already. What would she do if I didn't ask her? I knew what I had to do. The tears ran down my cheeks and I was scared to brush them away. 'Mistress, will you pull my panties down and spank me harder, please?' I really, really didn't want that to happen but it did. Her blows echoed around the room till finally couldn't take any more and fell to my knees.

'ARE YOU A SISSY?'

'Yes Mistress, I'm a sissy,' I get out between sobs. I can't believe how much that hurt.

'Are you going to do as told sissyboy?'

'Yes Mistress,' still sobbing loudly.

'Taking my chin in her hand making me look at her, 'You better, now thank me for your spanking.'

'Thank you for spanking me Mistress, I will try harder, I promise.' She wipes the tears from my face.

'Good girl, now go wash your face and come back to the living room.'

I go into the bathroom, throw cold water in my face trying to calm down. I can't believe it hurt that much with her just using her hand. Maybe the glove made it hurt more. I turn so I can see my ass in the mirror and it is bright red. It looked so strange, my ass so red. I reach back and rubbed it and could feel the heat on my cheeks. Damn. I finally feel composed enough to go back into the living room and force myself to try to act as feminine as I can. Mistress is in her chair having coffee.

'Come Billie, sit at my feet.'

I go sit down her chair and feel her hand rubbing the back of my neck lightly.

'I don't like to have to punish you like that Billie but I have learned it is the only way to make sissies like you pay attention. I have to admit, you do look so pretty when you are crying. I feel like at those times you understand. You did good Billie.'

I just sit there feeling weak and out of control. Her hand feels so nice but my fears make it tough for me to relax.

'I want you to go home now. Here is a list of my sizes. I want you to go home, get dressed like a boy and go to Victoria Secrets and buy some lingerie you would like me to wear tonight. I want to look sexy tonight, I need to feel like a woman tonight and want a romantic evening. Does that sound good Billie?

'Yes Mistress, that sounds very good, thank you Mistress.' Finally maybe we will get into some more sexual scenes with the Mistress. I wonder if she will let me fuck her. Even if she doesn't, maybe I will get to cum again sometime during the night.

'Good, now run along. Be back tonight at eight.'

'Mistress, I'm sorry but don't you have something else I could wear, maybe sweat pants of something.'

'Don't be silly, you look nice in that dress. You won't be outside your car much anyway, unless of course, you want to stop at the 7-11 for the boys again,' she says a smirk on her face. 'Now go.'

I grab my purse, my license and my $100 in there, and she lets me out. The neighbor opens his door and stares at me the whole way to my car. It's even worse this time since I'm trying to walk as feminine as I can in case Mistress is watching. He watches me till I drive off, kind of a scary dude.

I drove home trying to keep away from traffic taking some backstreets. Finally, I get home and go inside and get undressed and put on a tshirt and some shorts. I sit down and try to relax for a while. I was still having trouble handling what was happening. How did it all get out of control so quickly? I relaxed for a while then got ready and went out and found an outfit I thought Mistress would like. I bought a matching blood red bra and panty set. I found a black garter belt in a shiny material. Then I found some black silk nylons with seams up the back. I finished off the outfit with a long shear black nightgown. I hoped she liked what I got for her and couldn't wait to see her in it. It wasn't as bad buying the bra and panties because the difference in our sizes indicated that I wasn't buying the stuff for myself.

I am so excited about tonight and maybe getting into some wild sex with Mistress even though I realize she will be in control of things but at least we will be spending time together. I laid down to take a nap to get some decent sleep. I did get some sleep when I was in the cage but not sound sleep. I really don't like being put in there. I think it's the sound of the padlock clicking shut and knowing no matter what I want, I can't get out until she decides to let me out. It's such a feel of helplessness.

I get up and take a shower and get ready to go to her place. I take a couple of the pills and smoke a joint trying to relax but it's not easy to do. Finally, it was time and I drove to her place. She met me in a sexy royal blue robe and invited me in. She fixed me a scotch and told me to come into the bedroom with her. She made me sit down by her at her makeup table and talked to me about how she did her makeup and what needed to be done to make it look perfect. She puts on quite a lot of makeup and looks so sultry. She takes the robe off and hangs it on a hook on the door and turned to me. It was my first time seeing her completely naked and I couldn't stop staring.