A Mistress to Obey

'You really are a wimp.'

Feel like I'm being overwhelmed. Didn't really think it would get this intense this quickly. Before, in this kind of play, I always still felt that I had control of things but realize this is different. The way she talks to me leaves little doubt of what she thinks of me. My mind rushes as I think what she might have planned. What if it's too much for me? Do I dare not do it or what might she do to me. What if she would cage me again? I don't want that and better try harder to please her. She lifts the cage door and I back out. My balls still hurting so badly.

'Don't take all day bitch. You don't want to keep me waiting.'

She leaves and I get up and try to work out all the kinks from being in the cage. Rubbing my balls trying to ease the pain. I go into the bathroom and take a nice hot shower. It feels so good. Then go back into the other room and see the clothes laid out on the table. All that is there is the pair of pink panties with the white ruffles on the ass and a pink camisole. I put them on and I feel so stupid in them. The camisole has pink fluffy trim all along the bottom and has puffy sleeves. On the floor is a pair of pink slippers with 3" heels and pink fluffy ball on the toes. Look at myself in the mirror and realize how ridicules I look, but the thought of not wearing these things like she told me to, is not an option.

I force myself to walk back into the living room. The heels make me take small steps and I try to walk in a rather feminine manner. I feel this is probably what she expects of me and don't want to make her angry so I try to act as fem as I can when I enter. I walk into the living room and she is sitting in her soft chair and I move towards her when I see another lady sitting on the couch. The humiliation is instant as I realize what I must look like. I just stop there not knowing what to do. When I think about how I was walking and trying to act more fem when I came into the room only adds to the humiliation. Mistress gets up out of her chair and walks over to me. She rubs the back of her hand lightly over my cheek. It feels so nice.

'Ann, this is my new sissyboy billie. We have been getting to know each other haven't we sweetie?'

So humiliated standing there dressed like I am. Looking down, not making eye contact with anyone. Can't stop thinking about the look on the other lady's face. The look was what I would call a smirk. She looks like she was enjoying my discomfort.

She moves in front of me. 'I have just started her training. You will have to excuse her lack of manners. She forces me to make her remember her place.'

Suddenly, she knees me right on my sore balls. I drop to my knees grabbing my crotch as I bend over trying to minimize the pain.

'Where is your place when ladies are present sissyboy?'

'On my knees Mistress,' I say realizing my voice is a little higher than normal. I can't believe there is another lady here.

Mistress laughs, 'now you even sound like a sissy, maybe you need a knee more often to make sure you remember how to talk. Say hello to Mistress Ann.'

I look up, trying to look at her but so embarrassed that it's hard to make eye contact. Thinking about what she said, it try to keep my voice a little higher, 'Hello Mistress Ann.' She gives me a cold look then turn to Mistress.

'Where did you find this wimp?' she asks.

'The internet of course Ann. Place is full of weak men that need women like us. How is Chrissy's training going?'

'The little bitch was rather resistant at first but a couple evening all alone with her thoughts, made her realize how things were going to be. She's up to two weeks with her little cock locked away now. Think she is going to work out well.'

Listening, I realize that they are talking about another guy but they keep using feminine pronouns when talking about him. It makes me wonder if the nights alone were in a cage. There is something scary about Mistress Ann. She doesn't look like a woman you would want to displease. Think about how difficult it would be to be locked up, not being able to masturbate.

'What do you think of him Ann?'

'I don't know. I kind of like starting out with a man and turning them. Of course, sometimes it's fun to see how far wimps like him will go to please you. Guess I just like guys to be at least a little manly and I don't see that in him. Just look at him and the way he pranced in here like a little fairy.'

So embarrassing to be kneeling there as they demean me. Both of the ladies fully dressed and there I am in pink. Head down, rather worried where this might be heading. I see Mistress motion me over to her and I crawl over and she presses my head down to her heels.

'Clean them sissyboy.'

I start licking her heels as I listen to them.

'Ann, I still owe you for the night you let me borrow Chrissy. I thought maybe I could pay you back tonight if you liked him. I know what you like and think it might be just what he needs.'

Well, at least they are referring to me as him and not her now. The thought of spending time with Mistress Ann frightens me. She looked like she could be...you know...a real bitch. Hoping maybe what she said about me not being very manly might make her pass.

'I think I would like that Sherrie. I do want to get him out of his panties though. I think you still have that leather jockstrap don't you?'

'Of course Ann, not all my little boys are wimps like him. Back room sissyboy. NOW!!'

I start crawling back to the back room and can hear you both behind me.

'He does have a nice ass Sherrie, you tapped it yet,' Ann asks.

'Not yet, my bitches have to earn that and he's got a long way to go.'

We get back into the room and I hear it lock behind us again. I'm told to get up and take everything off and I'm standing there naked. My Mistress hands me a black leather jockstrap and I pull it on. It has a hole in the crotch and I pull my cock through the hole. Damn, I wish it would get hard so it didn't look so small.

'I can see why he acts like he does now, kind of hard to be manly with a tiny fucking cock like he has,' Ann states. 'I want to hook him up Sherrie, will you lower the cuffs.'

Mistress goes over to the wall and hits a switch, and a wooden beam with a pair of leather cuffs attached to it, descends from the ceiling and it's not long till my wrists are firmly cuffed. Then leather cuffs are hooked around my ankles and they are spread wide and hooked to chains coming from opposite walls. Then Mistress goes back to the wall and hits the switch again and the chains start lifting. She doesn't stop till I'm stretched out, my feet just barely on the floor.

Mistress Ann walks over in front of me and holds up a red leather ball gag. 'You are going to need this boy,' she says as she shoves it into my mouth and fastens it behind my head.

I'm feeling very worried about this. I watch Mistress go sit down on her throne just looking at us. Mistress Ann goes over to the wall and takes down a black leather flogger. She walks back in forth in front of me cradling the flogger.

'Look at me boy.'

I look up at her and I feel fear. I can feel this woman wants to hurt me and Mistress is going to let her.

'You probably thought that you were man enough to handle this and already I see the doubt on your face. Mistress Sherrie has started you on your path of discovery and I just want to take you on a little side trip to show you something. You don't mind do you boy?'

Really scared now of this lady. I shake my head no even though I don't want this at all and wish Mistress would come to my rescue. She moves behind me and I turn to try and look at her.

'Turn around bitch.'

Then it starts, first high on my back and then working down my back. It hurts but not that bad and think that I'm going to be able to handle it alright.

'Do you like warming them up Sherrie? I do, you know, letting them think this isn't so bad. They were all worried for nothing. You know what I mean?'

'Yes, it does make it better doesn't it?' Mistress replies.

'Yes but now, let whip this boy,' she says bringing the flogger down hard across my back.

I try to cry out but little comes out from behind the gag. Then over and over on my back till I'm cry hard, trying to avoid the blows but can't and just take it. Finally she stops and Mistress Ann comes around in front of me.

'That wasn't so bad now was it?' she asks, a cruel smile on her face. 'You deserve a reward.'

She kneels down in front of me and I can't believe it when she sucks my cock into her mouth and starts sucking me. It feels so good almost helping me forget the pain as I feel myself starting to react and get hard. Her mouth is so wet and so warm. Then I jerk as I feel pain in my cock. It takes me a moment to realize that she bite my cock. Then she does it again, her teeth feel so sharp as I try to pull away. She grabs my balls and pulls me back to her.

'Look at me boy,' she orders.

When I look down I see my cock in her hand, her mouth open and she places the head of my cock between her teeth and bites down on it as she makes me watch. It hurts badly and it's all I can do to take it. Then it feels like she started chewing on the head of my cock. I scream into the gag. Finally, she releases my cock but squeezes my balls hard.

'You are going to be a good boy for Mistress Sherrie and become whatever she decides she wants you to be, aren't you boy.'

'Yes Mistress Ann, I will be a good boy and obey her.'

'Good boy, now let's take care of that ass of yours. I just love flogging a nice back like yours but for that ass I really think a paddle will be best don't you boy?'

Sobbing loudly, trying to handle what is happening. I feel her hand grab my balls and squeeze, digging her nails in.

'I asked you a question boy.'

Not wanting too but too scared not too. 'Yes Mistress, I think a paddle will help me learn.' I watched her go over to the wall and take down a paddle. She brings it over looking at it as she stops in front of me. I can see the paddle now. It's all black leather, shaped rather like a ping pong paddle but the paddle being elongated a little making it less round and more into an almond shape. The paddle section about 12" long and 5" wide at its widest. She brings the paddle up to my lips and holds it against the ball in my mouth making it seems like I'm kissing the paddle. The look on her face says it all as far as what she thinks of me.

She moves behind me and it starts. The sting of the first blow surprises me and I cry out. The sound of the paddle hitting my ass is so loud. Then the blows come one right after the other till I'm jerking around in the chains trying to avoid the blows. Crying hard, my ass feels on fire. Then it stops and I try to compose myself and I'm sobbing loudly. Suddenly, another hard blow and I realize she isn't done.

My ass so sore. Can hear her walking up close behind me and feel her nails on the bottom of both ass cheeks and then she start scratching her nails up slowly. It's hurts but also feels so erotic that I find myself pushing my ass back. She rakes my ass several times and I'm surprised to find myself moaning more than sobbing. Then she takes the paddle again and gives me ten more hard whacks. Crying again,it hurts so bad.

'Thank me boy,' her breathe hot in my ear.

I can feel the tears running down my cheeks as I thank her trying to sound as sincere as I can. The last thing I want to do is displease her in any way.

'Thank you Sherrie, I needed that,' Mistress Ann says as she tries to quiet her breathing.

'You're welcome Ann, I do so like watching you work a boy. It's nice knowing that if I encounter any problems, I can always ask you to come over and help me make my boy understand his place.'

'I hope you do that, maybe Chrissy and him could spend some time amusing us. I better get going. Chrissy had an appointment tonight but she should be getting home soon and I need to be there and make sure the client was satisfied. I need to stay on top of things with Chrissy. She just started meeting clients for me.'

'I didn't realize he had reached that point already Ann. You really are an impressive trainer.'

Laughing Ann replies, 'You just have to understand that you know what they need better than they do and have to convince them to think that way and as you know, I have my ways of convincing them.'

'Yes you definitely have a way about you Ann, sometimes I wish I were more like you.'

'You will get there. You just need to concentrate on your needs and mold them accordingly. You really have to stop being so concerned about them, they don't deserve it. It's not what they want or need, they need firm control and discipline.'

'Thanks Ann, I know sometimes I'm too soft. I really appreciate you help.'

'Any time Sherrie. I got to go,' and she leaves.

Mistress walks over to me and just looks at me for a few minutes. Figure my eyes are probably red from the crying and know the tears that have run down my face are obvious. I have trouble making eye contact looking down embarrassed by my behavior. Finally she walks over and hits the switch and lowers the chains and she releases my wrists and ankles. I stay on the floor and when I'm released I crawl over on my stomach till my lips are on her shoe kissing and licking it.

'She thinks I'm too soft on you boy. Maybe I am, maybe you need someone more like Mistress Ann.'

'No Mistress, you are perfect. I want to serve you so badly. I promise I will do better.' My pleading genuine, the last thing I want is for her to ask Mistress Ann back over.

'I want obedient, I want total commitment to my wishes. Present.'

She walks away as I get up on my knees spreading them as wide as I can, hands behind my back, back straight, eyes down. When she comes back she places a saucer in front of me.

'You will jack off your cock and I want all your cum in the saucer boy. Tell me why I want you to cum in the saucer. Look at me.'

I look up at her and know what she expects to hear. 'You want me to cum in the saucer so I can lick it up Mistress.'

'I would never expect you to do that unless you wanted to do it for your Mistress.'

Thinking about all the times I have thought about eating my own cum but once I come the last thing I want is to lick it up but knowing the situation here, there is only one acceptable response. 'I want to lick it up Mistress if it would please you.'

'It would please me, now begin, masturbate for your Mistress, show her what a good boy you want to be for her.'

I start stroking and my cock is hard. Mistress talks to me, telling me she enjoyed watching Mistress Ann punish me. She tells me how she enjoys watching me cry and how my sobs make her pussy so wet. She tells me how turned on her got watching Mistress Ann chew on my cock and tells me how much Mistress Ann enjoys doing that and tells her how she really needs to see if she would like it.

'Come on boy, jack off that cock for your Mistress, show her how much cum you can shoot for her. Be my good little stroke boy, jack it fast for your Mistress. I'm going to count you down from ten boy. You will come when I say "cum." You will cum or I will be so disappointed.'

Stroking myself, know I'm close. She starts counting me down and I'm not sure I will last that long. Finally she get to one and then she tells me to cum and I cum hard shooting a big load into the saucer. Can't believe how good that felt.

'Good boy, now show Mistress just how big of a wimp you are, lick up your cum for me.'

I really don't want to do that, but know that if I don't, she will be disappointed in me so I lean down and start licking it up. It's so nasty and hard for me to do but I force myself to lick it all up.

'Very good boy, it's time for you to go home and think about what happened tonight. I will be getting in touch with you. I will give you a week to do as told as far as the panties but that is not negotiable. Now get up and get dressed.'

I get dressed and she shows me out. My mind races as I drive home. Looking forward to getting home and just relax and think about this encounter. It was intense but finally was an experience that was unforgettable. What might this lady expect from me and is going forward something I want now that I have had this experience. Know it will be on my mind as I what I will do and will have to see what happens. What will I do? What do you think?