A Mistress to Obey Ch. 04


'My little faggot sissyboy couldn't get enough of that black cock. It was the first time I realized what a wimp and faggot he really was and how badly he needed a woman like me. Isn't that true sissyboy? Don't you need me?'

'Yes Mistress, I want to serve you, I want to worship you.' The picture changes to where my face is covered with cum, my tongue out trying to reach to lick it off my face.

'My lesson here lady is you really might have no idea about the man you are interested in domming. You might find out things you really don't want to know. I was disappointed in my sissy at first wishing he was at least a little manly but look at him. He needs me and I'm going to help him become the sissy he knows he is and train him to serve women. Isn't that really what we want from men? Submission and obedience. You can make it happen and Mistress Anne will show you how now.'

Mistress Anne walks into the room in a black leather cat suit. A black leather corset fit snugly over the cat suit. Black leather lacing boots extend up over her knees, halfway up her thighs. Black leather gloves stretched tightly up over her arms overlapping the cat suit. A skin tight leather collar extends up her long neck. Her makeup is heavy and very erotic, her hair pulled tightly into a bun on the back of her head giving her such a domineering look.

'Hello ladies,' she says. 'I'm so glad you decided to spend the evening with me and I hope I can enlighten you on the pleasures and rewards of feminine dominance. I understand several of you lady are married and looking to change your relationship and that some of you only had occasional dominant experiences and want to learn more about the lifestyle.'

The ladies reply to her and looking at them, you can tell how impressed they are with her outfit and demeanor. I keep my eyes down not making eye contact with her.

'Excuse me for one minute ladies,' she says as she starts walking over to me. 'Who do we have here? Look at me.'

I look up at her. 'I'm Billie and I'm a wimp.'

'Well Billie, if I ever enter a room again and you don't fucking drop to your knees immediately we are going to have a problem. DO YOU UNDERSTAND BILLIE???' her face right in mine.

I drop to my knees immediately, head down.

She turns around and starts addressing the ladies again. 'Excuse me about that. As you have around discovered, Billie is Mistress Sherri's sissyboy. He has just started training recently and seems to have potential but it's very important that sissies are trained properly. Mistress Sherri feels like I might be helpful in his training. You will all be expected to take your turn bringing your sissy here to show how his training is progressing.'

She turns looking at me.

'Look at me sissyboy,' she tells me and I look up at her. 'There are different kinds of sissies ladies. There are those that just like to dress up feminine and be treated like a girl or woman. Sexually they are straight and still interested in satisfying the woman they serve. Then there are boys like Billie here,' she says looking right at me. 'Little sissy faggot boys that crave cock. They want it in their mouth. They want it up their ass. There really isn't much they won't do to be able to have a cock. Isn't that right Billie?'

It's so hard keeping eye contact with her but I answer, 'Yes Mistress, I love cock.'

'Tell them about the first night you came over here Billie. Tell the ladies what you did. I want you to crawl to the first lady to the right and start your story and then move to the next lady to continue. You will look up at them as you speak. Now go.'

I crawl over to the first lady and look up at her and see the look of superiority on her face as she looked down at me. 'My Mistress sent me over here to help Mistress Anne out with something, she wouldn't tell me what. I had met Mistress Anne before once but was very nervous about meeting her again.'

'Why were you nervous? Was it because you are a wimp?' the lady questions me further showing what she thinks of me.

'Yes ma'am, that is probably why.'

'I have to tell you that you didn't have to tell us you are a wimp. All of us knew it when we saw you,' the lady tells me. 'Crawl away, faggot.'

I crawl over to the next lady. 'Mistress Anne took me to a bedroom and made me undress for her. I saw the way she looked at me and found out later that she was disgusted that I wasn't smooth and she did let me Mistress know about it so I keep myself smooth all the time now.'

'I hope you got punished for that sissyboy, you should have known better. Are you stupid or just don't care enough?'

'My Mistress punished me for that Ma'am. It helped me learn that it's important to try harder to please women.'

'Go on, what happened.'

'She dressed me in an outfit that made me look like a sissy man. I couldn't decide whether the clothes made me feel feminine or, I think more likely, they made me feel like a fag. She told me that she wanted me to go meet a man. He was going to pay me to come see him. I was so nervous about going out dressed like I was especially since I was going to a strange man's house.' She just looked down at me and softly said 'fag whore' and turned away from me.

I crawl to the next lady and it's the lady from the cosmetics store. She looks down at me.

'Hello again sissyboy. In case you ladies haven't heard Billie came into my store to buy some makeup. He had a dress and heels on. Tell the ladies why you were wearing them.'

Knowing the more pleased Mistress Anne is, maybe she will take it easier on me. 'I'm a sissy and I love wearing pretty dresses and heels and love dressing up.'

'Ladies, it wasn't hard to see what a sissy wimp I was dealing with so I put lipstick on him right in the store while other ladies watched and he just let me do. What kind of man does that? I'm so glad Mistress Anne invited me tonight.'

'I'm glad you decided to come, June, wasn't it?' Mistress Anne says. 'I can see June understand how boys like Billie here need to be treated.'

'Yes and I hope his mistress will let him attend a makeover clinic at my store next Wednesday. We usually have a good turnout and think Billie would make an ideal subject, don't you ladies?'

Affirmative comments flow and I see my mistress just staring at me. I feel she is putting me out there tonight to see how I will react. I don't want to disappoint her.

'She would be glad to have your help in learning about makeup, wouldn't you sweetie?' Mistress Anne says her eyes boring into me.

'Yes Mistress.'

'Good, then that's settle. Now go to the next lady and tell her what happened next.'

I crawl to the next lady. 'I started to leave but Mistress Anne didn't think I was acting feminine enough and made me come back into the house and she punished me.'

'What did she do sissyboy?' the lady asks.

'She pulled my tight pants down and gave me a hard spanking.'

'Did you cry sissyboy?'

'Yes, she made...'

'Cry? You should have seen the little faggot. He was crying like a little girl and I wasn't even spanking him that hard. I thought he was a wimp before but this confirmed it. I have been thinking about him a lot since that night.'

She comes over beside me leaning over, staring at me. 'Tell the ladies how you feel about me.'

'I'm scared of Mistress Anne and what she might do,' I answer knowing better than to not admit it.

'What did I tell you when you told me you were scared of me faggot.'

'You said I should be scared Mistress Anne.'

'Are you still scared of me faggot?'

'Yes Mistress.'

'Good,' she says moving away leaving me feeling more intimidated than ever.

The lady looks down at me. 'I can't wait to watch her hurt you sissyboy,' she says turning away and I crawl to the next lady.

'What happened when you got to the man's house sissyboy?' she asks.

'He had me come in and he kissed me right away. It was my first time kissing a man.'

'Did you like it sissy?'

'Yes, his kiss was aggressive and helped me deal with being there and what was expected of me. I was so embarrassing when he gave me the money, having him think that I really was a gay whore.'

'But you were, weren't you? You were a gay whore and I bet you loved it. Bet you begged for his cock before you were done.'

'Yes Ma'am, I did beg for it.'

'Are you a cum slut sissyboy? Did you want him to come in your mouth?' she asks.

Looking down embarrassed, 'Yes Ma'am, I wanted him to cum in my mouth.'

'Look up at me and tell me you are a cum slut.'

I look up at her and see the same look I see in Mistress Anne's eyes. 'I'm a cum slut.'

She leans down in my face, 'WIMP. Look away, I'm tired of looking at you.'

I crawl over to the last lady. Mistress Anne walks over near me. 'Tell Helen how you came sissyboy. Look up and tell her and the other ladies.'

'I was sitting sideways on Mike's lap, my arms around his neck and he was playing with my cock through my panties. It felt so good and I came in my panties and he made me wear them back to my Mistress's house.'

'Have you ever heard anything more gay than that ladies?' Mistress Anne asks. 'I couldn't believe it when I hear it. What a fucking fairy.'

I hear all the ladies laughing and Mistress Anne tells to crawl into the center of the circle the ladies have made with their chairs.

'Up on your knees, back straight hands behind your back sissyboy. Spread your knees apart. Present properly.'

I do as told and Mistress Anne walks around me then takes a toe and tapes the cock cage. She picks up handcuffs off a table making sure I saw them then moves behind me and handcuffs me.

'I'm sure you have all seen this bulge. You are right, his cock is caged up nice and tight. His Mistress has to do that to make sure he isn't playing with himself all day and has more time to think about pleasing her. His mistress is pleased that he hasn't complained about it very much and feels he deserves a reward. Do you want a reward sissyboy?'

'Yes please Mistress Anne, I can't wait to get it off for a while.'

'I'm sorry sissyboy, but I don't remember saying anything about taking it off. I just said you deserved a reward. What do you think ladies? Do you think Billie deserves a reward?'

I hear mostly agreement between the ladies with at least one saying no and I know what one that is.

'I guess you get your reward sissyboy, Alex will you come in here.'

A muscular white guy, looks to be about 6'2", 200 and probably in mid 30's. All he has on it a dirty white jock with yellow stains so obvious. Under the jock, clearly outlined is a big cock. Hard to say how big but can tell it's very thick.

'Alex, this is Billie, he's a wimp. He loves sucking cock and the nastier the better. He has been being a good little sissy so his Mistress decided to let him have some cock.'

He looks down at me then at the ladies, 'sissy bitches like this make the best cocksuckers. There is nothing better that you can do to show your sissy his place then let a real man use him. It reinforces in their mind how little they are like real men. Look at this faggot at my feet.'

My mind racing, my cock trying to get hard in the cage. My body so sensitive, everything seems so intense. Having trouble concentrating but remember how all the ladies looked at me. My body feels so hot. I lift my head and look at his jock and see how nasty it looks.

'Did you see that ladies. The sissy can't help but check out my cock. He's starting to think how badly he wants it. He can't help himself, sissy faggots need cock.'

The verbal abuse stings but I have trouble thinking about it. His cock is right there and it looks like it has even gotten bigger. I wonder what it tastes like. My mind is racing, realize how high I am. I can't help but lick my dry lips.

'Look at him. What a sissy fag. But look at this jock ladies, I have been cumming in it nightly getting it ready for tonight. I made sure I pulled it up too soon when I took a piss too. You know why? Mistress Anne challenged me. She said I couldn't get a jock strap so nasty that the faggot she had lined up wouldn't suck it clean just to get to my cock. I thought there is no way any faggot would be able to handle this but look at him.'

I see my Mistress in the background. Mistress Anne walks over to me, lifting my head making me look at her. 'I know what a nasty boy you are, it's time you show the ladies. Tell them what you want to do for me faggot.'

'I want to lick his cock through his dirty jock Mistress Anne. I want to get it wet and suck it till it's nice and clean to show you how badly I want to please you Mistress Anne.'


'Don't lie to me you fucking wimp. Tell me why you really want to suck his dirty jock. Lie to me again and you will regret it.'

My cheeks stinging, 'I want to suck it clean so you will let me suck his cock Mistress Anne. I really want to suck his cock and I want him to cum in my mouth.'

'That's better, don't try pretending you don't want that cock faggot, now get busy and impress the ladies. Show them what a nasty little sissy faggot you are.'

I lean in and start licking on the jock. It's so nasty but as I get it wet I get those tastes of cum and soon I'm totally into it not thinking about anything but sucking on the jockstrap. I feel Mistress Anne pull my head back and show all the ladies my wet nasty face.

'Beg for cock bitch.'

My mind racing. I just look at it in the wet jock. I want to suck it. I want his cock in my mouth. I lean forward but Mistress Anne pulls me back. 'Beg for cock faggot.'

So hard to think about anything but his cock as he slowly takes it from his jock and holds it out in front of my face. My mouth so dry, I look up at him. 'Please let me suck your cock Sir? Please I really want to,' I ask knowing I really do want to suck him. I want it in my mouth.

'Open your mouth faggot, make a nice little fuckhole for my cock.'

'Look at him ladies, your sissies must be trained to be good cocksuckers. Once your sissy has had you stand there watching as a real man using him, he will never be the same. He knows you know what he really is. Just imagine,' he says as he puts his cock between my lips and slowly starts sliding his cock into my mouth. 'Just imagine what power that gives you over him and how you can use that power.'

His cock stretches my lips as he slides his cock into mouth slowly. I feel his hands on the sides of my head as he slides deeper and deeper. I feel his cock at my throat and start to choke. I feel him hold my head tighter as he presses forward until I'm gagging but he doesn't let up and tilts my head back and I feel his cock slide into my throat. I'm trying to struggle but no leverage and he holds my head tightly and pulls me the rest of the way onto his cock, my nose in his pubes as I struggle. Finally, he pulls me off his cock. I'm choking and gagging, slobber running down my cheeks, my face all wet.

'I am a dominant man, and this ladies,' making me turn so they could see my red face, tears running down my cheeks, 'this is a submissive faggot that you can never look at again without remembering what a fag he really is and he knows it. Imagine the power this will give you over him. Don't you want that power over your sissy? That is why they must be cocksuckers and eventually more.'

Head down as I listen to him and feel how we really are so different. I can't believe I had that big cock all the way into my mouth.

'Now ladies, I'm sure you have heard about face fucks. I am going to face fuck this faggot right now. Feel free to move around and get a good view as I face fuck him. You do want to impress the ladies don't you sissy. You know ladies, faggot like this,' slapping my face lightly, 'faggots like this boy often like to dress up as sissies so they don't feel as much like a faggot. Can you imagine that, thinking wearing around a dress around makes you appear less of a faggot. It is how their weak minds think and why they need ladies like you.'

He walks over in front of me and puts his fingers under my chin lifting my face till I'm looking at him and then suddenly he slaps me hard.

'Isn't that right faggot? Or maybe, you really want to be a girl. Is that it, you want to be some man's wife.'

Sobbing softly, 'I just want to please my Mistress Sir.'

He leans down looking at me. 'Do you know how badly your Mistress wants to watch me fuck your mouth? She seems to like seeing what a sissy wimp you are to real men. It's time for your cocksucking lesson faggot. Open wide.'

I see the ladies gathering closer and feel him take my head in his hands again. It's a repeat of what he did to me earlier making me take his cock deep in my throat and holding me on it till my face was getting red and he let me up. He turned my head slowly letting all the ladies get a good look at me.

I was choking again trying to get my breath. I see the smiles on the ladies faces. I see the way they look at me.

'Ok faggot, this time you do it on your own. Do not disappoint me boy. I know you like to think about yourself as a girl but when you suck a cock you suck it like a faggot.'

I take his cock into my mouth and start sucking it deeper and deeper. I feel it at my throat and try to push myself deeper but start to gag every time I try. Suddenly I feel a hand on the back of my head and it shoves me down hard forcing the cock deep in my throat. My nose is buried in his pubes.'

'He said take it all faggot. You will not embarrass your Mistress and me,' I hear loudly recognizing the voice of Mistress Anne.

She lifts my head up off his cock, trying to catch my breath as she pulls my wet face up and slaps me hard.

'Now fucking do as told cocksucker. You embarrass me one more time and you will regret it.'

She releases my head, her glare burning through me. I immediately take his cock into my mouth and start sucking him. Start moving up and down forcing myself to take a little more each time till finally I have him in my throat and I push forward and take it all. I realize I can really do this as I slowly pull back a little then take it deep again. Breathing through nose and start moving up and down taking more of a long stroke as I go, feeling it slide in and out of my throat. Not even aware where I am, cock is all I have on my mind. Sucking cock. Sucking his big cock. His hands move to my head and holds it still as he slides his cock in and out of my mouth, faster and faster, his balls slapping my chin. Suddenly, he pulls me off his cock.

'Open wide cum slut.'

I open my mouth wide, his cock in his hand as he strokes and then cum shoots into my mouth. I feel it on my tongue but keep my mouth open. He cums and cums all over my face. Feel it on my cheeks, chin, lips and even on my nose.

'Keep your mouth open faggot. I hope you ladies enjoyed that and Mistress Anne has my number in case you need my assistance in your training. I will leave this faggot to you ladies now. It's important you realize that this wimp you see in front of you thought he was a straight man only a few weeks ago. Now look at him.' He leaves the room.

'I hope you ladies enjoyed that, I know I did,' Mistress Anne says. 'Do any of you ladies want to help clean the cum off the faggots face?'

The lady who reminded me of Mistress Anne stands up. 'May I assist Anne.'

'Yes Katie, please.'

She walks over to me, looking down at me like I'm worthless. She takes one finger and scoops a big gob of cum off my cheek and holds it in front of my mouth.

'Suck sissyboy.'

I lean forward and take her finger into my mouth and suck on it tasting all the cum. It feels so slimy when it gets cold. I suck on her finger as she pulls it from my mouth. She doesn't say anything but can hear the other ladies making fun of me. She continues feeding me cum till I have swallowed all the cum off my face.

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