A Mistress to Obey Ch. 02

This story involves bdsm and gay play. Not your thing, move on.

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I can't stop thinking about what happened last Saturday. It was so much more than I expected, and frankly, I did things I never thought I would do. I had fantasized about forced fem but still was surprised how different I felt when in panties. It's just hard to feel very masculine when in a pair of panties. The public stuff was so scary, really didn't think I would do that, but can't stop thinking about how that guy looked at me in the parking lot. It was so embarrassing but that doesn't help me stop thinking about it and fantasizing about what might have happened. And the discipline. It was very painful at times and I so wanted them to stop but when I remember how I felt when they stopped, I understood it was their right to do as they did. It's not like I didn't come looking to be treated like that but it was so intense.

Will she call me again? What will I do if she does? I know that this might be more than I really want but can I say no? It sends chills up my spine every time I visualize her standing over me, legs spread, lecturing me on what was going to happen. That isn't the only place I get chills and I can't stop getting hard every time I remember her making me look at her as she glares at me expressing her feeling of me. I really think she thinks I'm gay. She emphasized it often enough, talking about me lacking masculinity and how easy it was so see. I wondered if she was right. Do strangers think I'm a faggot when they look at me? I have to admit, sometimes I see a look on a guy's face that makes me think they do. I can't keep eye contact when I see them look at me like that.

Her friend, Mistress Anne, was a very intimidating lady. Really wouldn't make to make that woman mad. I'm glad Mistress Sherrie is not like her, I don't think I could handle that. Mistress Sherrie is intense, and knows what she wants, but I don't think she is nearly as sadistic as Mistress Anne. I wonder if women like them become more sadistic as time goes by. Do they want to push more and more?

I ordered some panties online. I hope they get here before she calls me again. There were so many styles of panties it was hard to decide what to get. I finally settled on a variety with a couple thongs, a pair of sissy panties, baby blue with white ruffles, and several pair of bikini panties in various colors and styles. I have to admit, I did get hard while looking at all the pretty panties.

A few more days went by and sometimes I was relieved she didn't call so that I wasn't made to decide what to do. Then there was the rest of the time when I wanted her to call so badly. At those times, I knew what I would do if she called. I would do as told. It scares me where this could lead but I know that I can't say no to her. I need this.

Finally, the call came. It was Saturday, later in the evening when the phone rang. I answered and recognized her voice right away.

'How's my little boy?'

'I'm fine Mistress, thank you for calling.'

'I wanted to give you time to think about our night together. How are you feeling about what happened?'

'It was very intense Mistress. The spankings and paddling really hurt but, I have to admit, at the time it seemed like what needed to be done. I hope I wasn't too much of a wimp, I had just never been punished that harshly before.'

'It's suppose to hurt boy, how else will you learn to behave and do as told. I have to tell you I was somewhat disappointed in your behavior. I can't stand people that say they want something and when they get a chance for it to happen they just hesitate instead of just doing as told. Sometimes that can get so irritating.' Listening to her and already feel like I'm being lectured again. 'You realize that often the reason for the discipline is your fault and you make it necessary for me to make sure you understand.'

'I guess but I was trying hard to do as told and sometimes it didn't seem like anything I did was good enough to please you,' hoping it didn't sound like whining.

'Yes, exactly, you couldn't do anything right and whose fault it that?' the edge in her voice very evident.

Know I'm fighting a losing battle here, 'I guess it was my fault Mistress Sherrie.'

'You guess?' she questions.

'It was my fault Mistress.'

'Better,' she says.

I can imagine the look of satisfaction on your face. She is so different from other ladies I have met. It's all about her and she doesn't leave that in doubt and has no problem putting me in my place.

'Now enough whining about a little spanking. You know you loved it. You loved having a woman take control of you and treat you like you need to be treated. You want more don't you boy?'

I knew what I would say all the time. 'Yes Mistress.'

'Yes Mistress, what?' her voice cold.

'I want more. I want to submit to you and I want you to be my Mistress, please.'

'Will you do as told, no excuses. Public play will not happen without your approval. Other than that, you do what I say, when I say, with who I say. Understand.'

'Yes Mistress, I understand.'

'I will test you boy, you sure you are up for this?'

'I think so Mistress, I will try hard to please you and do as you say,' I tell her trying to sound submissive.

'I don't want to hear any of your bullshit, you up for this or not bitchboy?' her voice domineering and loud.

'Yes Mistress, I am.'

'Good, then we will not have a need for anyone to see the videos from last week.'

'Videos? You have videos of the other night?' I ask, a little panic in my voice.

'Of course, bad boys must be kept in line. Don't worry, you behave and no one will ever see them. I will send you a copy, I'm sure you will enjoy watching it with your little friend. Now, I need you to go over to Mistress Anne's place at 10 tonight, she needs us to help her out.'

'Please Mistress, can't I come see you. I have to tell you I'm kind of scared of Mistress Anne.'

'Jesus fuck, you just told me you will do as told and the first thing I tell you to do, I have to hear this shit. Do you think I care if you are such a wimp you are afraid of her. Fuck, try to act a little like a man will you. Damn, I don't think you are worth the trouble.'

'I'm sorry Mistress, I'm sorry. You are right, I just wasn't thinking right. I will be at her place at 10 tonight. I will not disappoint you Mistress.'

'When she releases you, you come straight to my place. I want you to stop and pick up a dozen condoms at the 7-11 just before you get to my place. Now, I have more important things to do then talk to you, you do what Mistress Anne tells you to do or else. We already have a little work to do to make sure you start thinking right. You don't want to make that worse.'

'I will come to your place Mistress. Can you tell me what Mistress Anne wants with me?'

'I don't know what she needs you for, she just said she did. That is all you need to know boy.' Then she hangs up.

I'm panicking thinking about going to see that woman. I look at the clock and realize it's after 9 so I take a quick shower and put on some dockers, golf shirt and some slip-ons. It's already time to leave so I grab a joint and head out the door. Smoke half the joint on the way to her place. It helps me relax and always makes me feel more submissive. I get to her place and knock on the door. It opens and Mistress Anne is standing there.

'It's about time, get in here.'

I come into her fancy house and realize this lady must have some serious cash. I follow her into the living room. She turns and looks me over.

'That won't do, follow me,' she says heading up some steps.

I follow behind her, admiring the black leather dress she has on. Her black hair is pulled tightly into a bun on the back of her head. I can see the garters attached to her seamed nylons and the black leather shoes have such tall spiked heels. Her legs and ass look so hot. She leads me into an extra bedroom and opens a closet full of clothes.

'Undress and hurry it up,' she says, her attitude mindful of the way she was the other night, bitchy.

She throws a pink nylon thong on the bed as I finish undressing telling me to put it on. I do as she says. It's tight and holds my cock snugly. The string up my ass feels so strange.

'Try these on,' she says handing me what I guess were a pair of pants. They were a real stretchy material and looked way too small.

'These are way too small. I will never get these on,' I say to her.

She snaps her head around. 'I said to put those on, now get your faggot ass in those and stop bothering me.'

I start trying to get them on and realize they do stretch enough that I can get them on but when I get done adjusting everything, I realize how low they ride on my hips and they come to just below my knees. They fit skin tight and you can see the little bump my cock makes in them clearly. They pull into my ass crack highlighting my small ass cheeks. She just turns and checks them out and I can see her smile as her turns back to the closet.

She holds a burgundy colored blouse up in front of me. 'Perfect, put this on.'

I put it on, it is a really silky feeling material, has long puffy sleeves but when I go to button it, I find no buttons.

'Like this boy,' she says as she grabs the long ends of the shirt and ties them together. It is short enough that my bare midriff shows and it falls open in the front down below my pecs, hiding my nipples but not by much.

She places a pair of black pumps with two inch heels on the floor. 'These should fit you, get them on.'

I put them on and she leads me over to a full length mirror. I can't believe how I look. She walks around me looking them comes back with some hair spray and sprays my hair and combs it all back behind my ears. I'm sure you have seen pictures of really feminine looking gay guys. That is what I was seeing in the mirror. Mistress Anne came up behind me and put several gold chains around my neck. They are long enough to hand down between my pecs emphasizing my bare chest. Then some pink lipstick, nothing too obvious, but anyone looking carefully could see the shine on my lips. i can't stop looking in the mirror. I can't believe I look like this.

She leads me into the living room. 'I overbooked tonight Billie. Chrissy is busy and I need you to help me out. His name is Mike and here is his address. It's a house so no one will notice you. He will be expecting you and I will discuss what he wants before you arrive and he will pay you as soon as you get there.' She hands me a small black leather hand purse. 'Your lipstick, along with some condoms, are in the purse. Keep the money he gives you in there.'

'Mistress Anne, I'm not gay. I have never been with a man before, I don't know what to do or if I could do it.'

'I know, that is why he is paying so much. He is older and will not expect too much of you. He might spank you and I'm sure you will suck his cock. I don't know if he will want to fuck you or not. I expect you to act like a flaming fagboy for him. Your walk, your voice, your mannerisms are expected to reflect a total sissy fag, understand?'

'Mistress, I don't know if I can do this. Please don't make me go out looking like this.'

'Looking like what? A flaming fag? You bitch, I hope you fuck this up and Mistress Sherrie lets me loose on you. Mistress Sherrie may not know it yet but I know what a fucking sissy wimp you are. Give me a couple nights alone with you and I'm sure you would have no doubt either. So bitchboy, you decide, become a flaming fag for this man or not, but it will get back to me, and I will get together with Mistress Sherrie and we will see where your ass is then. I know where I want it to be bitchboy.'

I know what I must do. If this man isn't pleased with me, things could get much worse. 'I will do it Mistress Anne. I will do what he wishes.'

'Good girl, now here is his address. When he finishes with you, you are released and I think you are supposed to report to Mistress Sherrie.'

'Yes, those were her instructions.'

'OK, go there when you leave Mike's. I will get your other clothes back to you later. Now go.'

I start to walk to my car and am so glad no one is around seeing how I'm dressed. Feeling relieved that I didn't get disciplined by Mistress Anne but still panicking thinking about meeting a man like this.

Suddenly, I hear her cry out loudly to me, 'Get your sissy ass right back here, NOW!!'

Look around, hoping no one heard her but see one house light come on so I hurry back towards her house, fighting the heels but trying to get back unseen. She grabs my arm and pulls me into the house slamming the door.

'You fucking think you can just ignore what I tell you bitch?'

Confused, not knowing what I did wrong. 'I'm sorry Mistress Anne, what did I do wrong?'

'Didn't I tell you to act like a flaming fag?'

'Yes, I told you I would Mistress.'

'It sure didn't sound like it when you told me good bye and it certainly didn't look like it walking to your car.'

'I didn't know you wanted me to start doing it now Mistress, I'm sorry.'

SLAP, her hand striking my cheek hard. 'Don't give me fucking excuses. You do what I tell you when I tell you. UNDERSTAND???

Wanting to rub my cheek, her slap really stung. 'I understand Mistress,' I tell her trying to sound as gay as I can when I answer her.

She points to a soft chair in the room. 'Lean over the back of the chair, hands flat in the seat and don't you dare move them.'

The fear settling in but don't know what I can do except obey and I do as she says. She comes up behind me and starts pulling the stretch pants down until she has them down to the bottom of my ass cheeks.

'I don't think you understand but you will boy,' she opens up a drawer and takes out a wooden paddle similar to what you see in fraternities. 'You will count boy.'

The first blow strikes my ass and I can't believe how much it hurt. It stings so bad as I try to handle the pain the next blow strikes my ass. I cry out loudly wanting to reach back and protect my ass but know that will only make it worse.

'Stick your ass out and take it, you fucking fagboy. You will learn to obey. Now fucking count bitch.'

I count out the blows as she punishes my ass. By the time I get to five, tears are already flowing and I'm crying hard as she stops at ten. I know my ass has to be so red. That paddle really hurt.

'Maybe know you will start paying attention. I am not like Mistress Sherrie, I won't put up with any of your bullshit. Now, your walk. Obviously, you need help as you showed walking to your car. I think I can help you with that.'

She gets something out of the drawer and then comes around in front of me showing me the black buttplug she is holding. She takes some lotion of a table and starts lubing the buttplug.

'You ignore instructions, there are consequences. Now, let's fill up that little pussy of yours.'

She moves behind me and presses the buttplug against my ass. 'Push back boy, I'm going to hold this and you are going to move your pussy onto the plug. You have one minute or we stop and I get the paddle and we start over. Your time starts now.'

Scared, I push back and feel the buttplug slide in a little and I can feel it start stretching me open. It hurts some but nothing like the paddle as I force myself back further and feel it slide deeper. Oh god, it feels so big.

'Take your time sweetie, I don't mind another session with the paddle, do you?'

I press my ass back hard and cry out as I feel it open me wide and then I feel it slide in far enough that I can feel my ass clamping down on the narrower end of the plug. It feels so big up my ass and hurts a lot. She grabs my forearms and pulls me upright and it makes the plug seem even bigger and makes me cry out.

'Maybe next time, you do as you are told faggot.' She opens her front door and pushes me out. 'Go, you are late.' She slams the door.

I try walking and the plug moves in me and makes it hard for me to walk without it hurting. I go out her front door, still so uncomfortable, taking small steps and can feel my ass swishing as I try to ease the pressure of the plug. I'm almost to the car when I see a neighbor a couple doors down watching. It's an older man. He doesn't say another just staring at me. It's so humiliating, I know what he has to be thinking.

I get in and drive off lighting up the rest of the joint. Damn I need it. What if I would get stopped looking like this? I can't keep doing these things with these ladies. It really is too much. I finally get to his house. Feel so embarrassed walking up to his house holding my little purse in my hand. He answers the door after I ring. He's older, maybe 50, in a suit. He looks like a executive or some professional and he invites me in, introducing himself and letting me know he is a doctor.

'You are a very pretty sissy,' he says taking my hand and leading me into his office. 'First, we take care of business. Here is your money,' and he hands me $400. He then hands me a bottle of pills. 'Take two of these every morning, two more at night. I will be able to tell if you are taking them.' Unknown to me, they are a female hormone pills with an addictive additive that makes stopping very hard. He handed me some water and I took two of the pills. He then handed me a prescription. 'This is for some crème that will help keep your hair from growing back. Use it before taking a shower. Leave it on for 10 minutes before rinsing it off.'

'Yes Sir,' I answer trying to sound fem. I force myself to try and act as faggy as I can with the way I stand and smile at him. He surprises me by pulling me close and kissing me. At first, I try to resist but remember what Mistress Anne said about the doctor reporting back on my behavior so when I feel his tongue on my lips, I part my lips and let him slide his tongue into my mouth. It's so strange but I start sucking lightly on his tongue. I feel him respond and before I realize it I'm kissing him like I'm loving it. He breaks the kiss and I feel like I'm short of breathe.

'You really haven't ever been with a man before?' he asks.

'No, really, I haven't. When I met Mistress Sherrie I explained to her that I wasn't gay but she didn't seem to care and somehow I ended up over here. I'm very nervous.'

'You kiss like a girl, do you know that?'

'No Sir,' not sure how to take that.

'You might not have realized it or accepted it but it's not hard to see that you are bisexual if not totally gay. Turn around. I want to see your ass.'

I turn around and feel his hands moving lightly over my ass cheeks. I have to admit it felt good but was so crazy being felt up by this man.

'Such a cute little ass. I hope Mistress Sherrie realizes what she has here and doesn't waste your cherry. I want you to tell her not to give you to anyone else to fuck without calling me first.'

I can't believe how this conversation is going. It sounds like he thinks Mistress Sherrie owns me. I know I told her I wanted her to be my Mistress but there has to be limits. I really wish she hadn't videotaped our time together. What if she were to show that video to others? How could I face someone knowing they had seen me like that?

'Let's go sit down sweetie,' he says taking me hand and leading him behind him. He approaches a black leather chair, takes his suit coat off, and sits down. 'Please stand, I want to look at you.'

'OK,' I answer standing in front of him feeling very uncomfortable.

'Are you alright sweetie?' he inquires.

'I guess, it's just...I'm dressed like this...and I'm here with a man I don't know. I'm sorry but it's all a bit overwhelming.'

'You haven't dressed fem before sweetie?'

'Please don't call me that, I feel ridiculous enough already but no never.'

'Do you think you should be telling me what to say and not say?' he asks his demeanor changing. 'Is that what you think?'