A Mistress to Obey Ch. 04

Realize the cum is still on my cheek. The way he looks at me is so predatory. 'No, I have to go.' He shoves a piece of paper in my hand.

'Call me. She doesn't have to know. I know what you need sissyboy, and I can give it to you.'

'I got to go,' and I get into my car and drive off. Get home and go sit down, staying in the dress and heels. What am I going to do? What if Dave talks to others? I smoke a joint trying to relax. Get up and wander around trying to think about the situation I'm in. I end up in the bedroom in front of a full length mirror looking at myself in the dress and heels. Find myself trying to pose to look more feminine. Notice how the heels make my legs look longer and they look so different being smooth.

What am I doing admiring myself in a mirror? What is wrong with me? Even thinking these thoughts, I don't take off the dress and heels and I go back into the living room. Find I'm not having as much trouble walking in the heels as before. Sit down and think about the whole situation when I feel my cock start to get hard then can't and I remember the chastity cage. Oh god, what if I need to get out of it. She has the key. I sit down thinking about how I have lost all control of my situation.

I don't hear from her for the next four days and I'm beginning to worry about not seeing her again and what I could do about my caged cock if I can't get ahold of her. Then remember, I do know where she lives and that helps me relax some. Then Friday evening, I get a call from her.

'Hello sissyboy, have you missed me?'

'Yes Mistress, I'm so glad to hear from you.'

'I bet I'm not all you missed you little wanker. Is my little fagboy all frustrated?'

'Yes Mistress, it has been very frustrating. Not even being able to get hard is hard to handle.'

'You poor boy. Would you like a chance to play with your little cock again and cum for your Mistress?'

'Yes, please, I need to cum so badly.'

'Will you be a good girl and not whine?'

'Yes Mistress, I will be a good girl,' can't believe I'm saying this but want to get uncaged so badly and really want to cum. I am used to masturbating at least a couple times a day.

'Then be at Mistress Anne's home at ten tonight.'

Panicking, 'but Mistress, can't I meet with you instead?'

'Don't worry silly boy, I will be there and I won't let her hurt you, at least not too much.'

The feeling of helplessness overwhelms me. If I want to get the cage off, I have to see Mistress but thinking about the pain I experience with Mistress really makes me worry about Mistress Anne. There is just something about her that makes me fear her. 'I want to please you and serve you Mistress and will be at Mistress Anne's home at ten. Mistress, please don't leave me alone with Mistress Anne, please.'

'I know you are scared of her Billie. I love the look on your face when I mention her name. You look like such a wimp. You don't mind me calling you a wimp, do you Billie?'

I hate it when she calls me that but the way she looks at me when she does make me believe she is right. I feel the need to submit to her. 'No Mistress.'

'You are a wimp. You know I'm right. No real man would let others treat him like you let other people treat you. This should help convince you that I'm right. You will wear your dress and heels over tonight, no panties. I want you to stop on the way over tonight at the Sally Cosmetics a block before her house and buy a nice shade of red lipstick you want to wear for me. I want to see the receipt sissyboy.'

'Please Mistress, please don't make me do that. How can I walk in there in a dress and heels? Please Mistress.'

'Ten tonight sissyboy. Don't be late,' and she hangs up.

Oh god, why does she keep pushing me so hard. She has to know how hard that will be for me to do. But, if I don't do it? What if she refuses to take the cock cage off me? I don't know what might happen if I go there and don't stop and buy the lipstick. Would she turn Mistress Anne lose on me. What will follow if I don't obey?

I go into the bedroom and undress needing to start getting ready. At least, I didn't have to think about this all day and realize how little consolation that should be. I get wet and then spread the lotion all over my body. I know Mistress will expect me to be smooth for her. I wait till it has had time to work and rinse it off. Rubbing my body, it feels so nice all smooth. Run my hands lightly on my nipples and moan softly. Damn, that feels so good. Pinching one nipple lightly and can't suppress another moan. Feel my cock start to response then feel the cage restricting any growth. It's so frustrating. I want to masturbate so badly.

After finishing my shower, I go get ready to get dressed. I take the dress out of the closet and lay it on the bed and look at myself in the mirror. I look so different being smooth and hairless everywhere. I look at my cock encased tightly in the clear plastic. What kind of guy does this? I look at the dress and go put it on and look at myself in the mirror. It's such a strange feeling looking at myself in a dress and realizing I like the way I look in it. I want to put the heels on and go get them and put them on. They make my legs look so different. I find myself posing in various ways trying to look more feminine.

Come back to my senses and realize what I had been thinking. Fuck, I have to put a stop to this somehow. I think it's a fear that I'm starting to like it. Realize some of it I do like but the public stuff is so scary and humiliating. And the punishment. It is punishment and not like you fantasize about. It hurts but I know often it's my own fault. I know I should try harder to please her all the time. I go take the pills she gave me to take morning and night and get ready to go.

I pick up the pink leather hand purse. She told me to always carry my ID, money, keys and makeup in the purse whenever I was coming to see her. I look at myself in the mirror. I have my hair combed like she likes with bangs. I almost wish I had some makeup to put on. How can I walk into the store looking totally like a man with a dress and heels on? Oh, god, why does she do this to me?

I work up my nerve, leave and drive to Mistress Anne's. I see the cosmetic store and pull up in front of it. How can I do this? I know I have to. If I don't I know it will be worse. I finally get out and walk into the store. A couple other ladies are in there and an older, stern looking lady is behind the counter. I make my way to the lipstick, my high heels clicking on the hard floor. My face feels so hot, know I must be blushing badly.

'May I help you?'

I turn and see the clerk behind me. 'No thank you.'

'I see, you are familiar with lipstick and cosmetics then?' she asks looking at me.

'No not really. I was just going to pick one.'

'I bet you want something that doesn't come off very easy, don't you?' the look on her face saying it all. 'Probably something in a bright red. Bet you want those lips nice and shiny.'

I look down, knowing what she thinks of me. I feel totally humiliated and see the other two women staring at us. She picks up a tube of lipstick.

'Let's try this one. Pucker up your lips.'

'No please, I just want to buy it and go.'

'You really should try it before you buy it. Now do as you are told and pucker up.'

She takes my chin in her hand and holds my head up making me look at her and when I do I know if I don't want things to get worse I better do as she says so I pucker up my lips and feel her putting the lipstick on me. She turns my face towards a makeup mirror and I see my lips. Cherry red and they look so wet.

'Now that looks better, I'm sure he will like you much better now. Now pay for this and get out of my store sissyboy.'

I pay and leave and hear the ladies all laughing as I go out the door. I get in and just sit there. I see them looking at me through the window laughing at me. I finally settle down enough to drive to Mistress Anne's. I can't really do anything about the lipstick and know if I will try it will just look worse. I get out and go knock on the door and Mistress Anne opens the door.

'Well hello sweetie. If it isn't my favorite little sissyboy. Come into my lair sweetie.'

She is in a short, tight leather dress, black seamed nylons and high spiked heels, looks like they must be at least 5" heels. A black studded leather collar adorns her neck. I follow behind her, her ass swaying. She scares me ,but at the same time, is so sexy. Mistress is sitting there in a big black leather chair. She has a tight silver dress with black seamed nylons and 5" black patent leather pumps. Her makeup looks so sexy. She has a riding crop laying across her lap.

'Would you look at my little sissy,' Mistress tells Mistress Anne. 'The little bitch couldn't wait to put her lipstick on. I know you couldn't put it on this well. Who put lipstick on you Billie?'

'The lady at the store Mistress did it Mistress. I told her I didn't want to do it but she insisted I did. She made a nasty comment about a guy liking me better now.'

Mistress Anne picks up the phone and calls a number. 'May I speak to the lady in cosmetics?'

'I am the only one working here at the moment, may I help you?'

'A friend of mine just stopped there and told me how nice you were putting lipstick on him. I'm having a few friends over, I live about a block away. I thought maybe you might want to join us for an interesting evening.' She listens, then, 'OK, we will see you in a little while.'

I stand there listening to all this. A few friends? I wonder what Mistress and her friend have planned and what it will mean to me. I get a feeling that buying the lipstick might not be the worst thing that may happen to me tonight.

'I have been looking forward to meeting you again Billie. Your Mistress tells me you are scared of me. Is that true?'

No use lying, I answer, 'yes Mistress Anne, I am rather scared of you.'

'You should be sissyboy,' Mistress Anne says moving in front of me. 'Not all women are as kind as your Mistress. You better appreciate her and serve her well so you don't end up with a woman like me.' She slaps my face lightly and moves away.

Mistress stands up, 'Follow me sissyboy. We need to get your ready before the rest of the guests arrive.'

I start to follow her when Mistress Anne commands me to stop. I stop but Mistress continues to the room. Mistress Anne hands me two pills and a glass of water. 'Take these sissyboy and think about what is going to happen to you tonight. Your mistress tells me you haven't totally accepted the situation yet. She wants me to explain it clearly to you. Think about that sissyboy. I have been waiting for this,' she tells me just loud enough for me to hear.

Fuck, I just take the pills and take them as she watches. I am definitely scared of this woman. Just the way she looks at me makes me shiver. Her smile due to me swallowing the Viagra and Exstacy and knowing what it will do to me.

'Ok faggot, go get ready and think about the next time you see me,' she says as I turn to walk away, 'Stop, on your hands and knees, crawl back to your Mistress. I will not tolerate your behavior in my house and it better fucking change. You are a fucking sissy faggot and don't you fucking forget it.'

I go down onto my hands and knees and crawl away. Really worried about what is happening.

'Fucking faggot.'

I crawl back into a bedroom where Mistress is waiting for me. It's a very feminine room, all done in pinks and whites. Big canopied bed sits against one wall, a makeup counter on opposite wall. She leads me over to the makeup counter, sits me down and turns me where I can't see and starts working on my face. She takes a long time with it and when she finishes she takes an auburn wig out of the closet and puts it on me and combs it out.

She turns me around and I can't believe how I look. Full makeup, fake eyelashes, a totally feminine look. I can't believe how feminine I look. She comes over and starts putting white nylons on me. Then she has me stand and fastens a white leather corset around me and starts tightening it. She doesn't stop till my waist has really been taken in and I have trouble taking a deep breath. She hooks the garters on the corset onto the nylons. Then she brings in 4" white spiked pumps and puts them on me.

She stands me in front of the mirror and I can't believe what I see. The corset not only restricts my waist but it pushes up making it look like I have really small breasts. Also makes my ass stick out more and between that and the heels, my legs and ass look so much different. She hands me a pair of silky white panties with lace all around them.

'You put these panties on sissyboy. 'I'm not sure I'm comfortable letting the ladies know my sissyboy has such a small cock.'

I put the panties on and when you look, you can still see the bulge the cage makes but at least it's covered up. She makes me stand in front of the mirror and look at myself.

'Tell me what you are Billie.'

Trying to sound as feminine as I can as I answer, 'I'm a sissy faggot.'

'I do not want you to disappoint me tonight sissyboy. Mistress Anne gives lessons to aspiring dominant women and it works best if she has a sissyboy to demonstrate with and she begged to use you. What could I say?'

I know there is nothing I can do about what is going to happen and resign myself to it. 'I want to please you Mistress, if you want me to do this I will do it for you.' I look at myself in the mirror and I look like such a sissy slut.

'I want you to concentrate on your voice and your mannerisms. It's important to please Mistress Anne. You must not forget this. I know she can be verbally abusive but I want you to pay attention to what she says or it will be more than verbal. You do have a lot to learn Billie.'

'Please don't let her hurt me Mistress, please.'

'Now you just settle down Billie. Just do as you are told. Now her lesson tonight is 'Helping your sissy accept what she is.'

'Mistress, I'm scared.'

'Now I have a gift for you that I feel will help you understand how things are Billie,' she says as she moves a pink leather collar around your neck and feel the padlock click locking it on.

I look at the collar and reading backward in the mirror. I see the large silver letters spelling out WIMP.

'When you meet a lady or a group of ladies you will introduce yourself in this manner. "My name is Billie and I'm a wimp.'

There is no doubt that she is totally into her dominant personality and her manner of dealing with me leaves no doubt in my mind that things are really starting. I feel a rush through my body and I feel so warm suddenly as the drugs start affecting me. I just stare at myself in the mirror. Having trouble focusing unless I concentrate.

'Tell me you want to be a sissy slut and show the ladies what a sissy faggot you are.'

I try to say it as feminine as I can but as soon as I finished her crop lands across my ass cheeks very hard.

'You don't fucking understand. I expect a slutty little bitch that can't wait to show women what a fucking sissy I have turned you into.' WHACKKKKK. 'You better make a convincing sissy slut or else.' WHACKKKKKKK. 'Do not disappoint me.'

My ass is really stinging. There are three red lines across my ass. 'I will be a good sissy Mistress. I want you to be proud of me Mistress.'

'If you ever want out of that cage, you make sure you do. Now it's time for the ladies to meet you.'

Mistress hooks a silver chain onto my collar and leads me into the living room. There are eight ladies sitting around the room including the lady from the cosmetic store. Mistress Anne is nowhere in sight. I feel so humiliated as the ladies look me over commenting to each other. She leads me through them all and then turns and leads me back through them again. I concentrate on trying to walk as sexy as a can crossing one foot back in front of the other exaggerating my swish. Know I better try to behave as they expect.

'This is my sissy, she just started training just a couple weeks ago so as you ladies can see it doesn't have to take a long time to change a boy's behavior. It does help if they don't think about themselves as being very masculine to begin with. My sissy was like that. Of course, he thought he was a straight man interested in serving a dominant woman. I soon discovered how wrong he was. There was very little manly about him at all and I have discovered that he is really gay and prefers cock. He really isn't man enough to even accept what he is. He does need women like us to help him though. Women like Mistress Anne understand how to properly take a man and train him to become your sissy and get him to accept himself as such. Introduce yourself sissyboy.'

It's so humiliating standing there on display as she tells all the women about me. I can see the looks on their faces and it's easy to see what they think of me. I know what I must do. "My name is Billie and I'm a wimp.' I hear the laughing and comments.

'I have prepared a small slideshow for your viewing pleasure while Mistress Anne is getting ready. Now Billie, stand to the side there where all the ladies can see you and you can see the television.'

She turns on the tv and hits the dvd button and a picture appears on the television. It's me at Mike's. I'm on my knees, his cock in my hand, giving his cock a kiss. It looks like I'm loving it.

"This was Billie's first cock. As you can see, he couldn't wait to get it into his mouth.' She hits a button and the picture changes to where his cock was deep in my mouth. You could see some slobber at the edge of my lips. 'It seems like Billie is a natural cocksucker, look at her. You loved it didn't you Billie?'

So embarrassed and humiliated as I hear the ladies talking about the pictures. It's so degrading but I know what I must do. 'Yes Mistress, I loved sucking his cock.' I hear several of the ladies laughing.

'Why don't you tell the ladies what happened then Billie.'

'I sucked his cock till he came and he came in my mouth and on my face,' I tell them as she switches to the picture of me with a mouthful of cum and cum on my cheeks and chin. I just look at the picture. Starting to feel the drugs, mainly my body feels so warm and I feel my cock responding against my will, trying to get hard but the cage is too small. I shake my head as I feel a chill run through my body. What a rush. I try to focus on Mistress's voice.

'You like the taste of cum don't you sissyboy?'

'Yes Mistress, I like it.'

'Why don't you tell the ladies about your saucer sissyboy.'

Oh, god, why does she do this to me but I answer. 'Mistress places a saucer out for me to masturbate into and then I lick it all up.' As I do the picture of me and the saucer, mouth open showing the cum I just licked up. Can I feel more degraded? I hear them all laughing and making nasty comments. Wishing I didn't have to look at them but she told me to make eye contact with the ladies. Let them see what a fag I am.

'She loves it girls, I don't think she can get enough,' and they all laugh.

'Do you want to tell the ladies about Terrell sissyboy?'

Oh no, I know what she is going to show them. 'Yes Mistress, Terrell is one of Mistress's lovers, he is black.'

'What else sissyboy?'

'He has a big, black cock.' As I say it a picture of Terrell comes on. Standing there, his big cock hanging between his legs. I hear the ladies nasty comments about his cock and how big it is. She changes the picture and I'm on my knees, my mouth open, his cock all wet, my cheeks wet from where he rubbed his cock on my face.

'Think my little sissy wanted that cock girls?'

Hear all the nasty comments and the picture changes to where he had my head in his hands and his cock deep in my mouth, my cheeks bulging.