Mother Dear Pt. 01

"Let's say for instance that I had son that was a sissy boy. A son that not only was a sissy boy that did very dirty and naughty things while he still lived in my house, dirty things for our next door neighbor, but a naughty little boy that liked to dress up in his mother's underpants too. I think a boy like that would need guidance. Don't you? I remember what you used to be like while still living at home with me. Don't I, dear?"

She smiles broadly. She is sitting across the table from me. She is a stunning woman. Her tight red blouse pulls her breasts together. It's unbuttoned low enough to show the black lace top of her bra in the lower center of her ample cleavage. She's gorgeous and knows it. She is the epitome of an erotic 'cougar lady' fantasy, the older woman, a super hot vixen.

She leans forward.

"And let's say that my naughty son from time to time would watch his mother, spy on her from the basement when she brought a man home to her bedroom. What if I had a son like that? What if I decided that a naughty little boy like that interested me in naughty little ways. What if he would please his mother very much in secret ways, even get touched in special ways by her from time to time if he followed her guidance and rules."

She sips her wine, goes on. She has prepared for this. I can tell.

"Would that be you, honey? Would it? Would that be you, my son, my baby boy?"

She stares at me coldly, smiles wickedly. I am hypnotized by what I am hearing, enthralled. My mother has known about me, even helped me with makeup, helped me dress up in all the girl things just after high school. Just after high school she let me know that she knew about my attraction to men as well as women. She knew all that I did. She knew I was playing with the neighbor man next door when his wife was away. She told me she supported me and my desires, told me I should never be ashamed of what I am, who I am. But she never talked to me like she is talking to me now. She now sits across from me speaking to me like she never has before. And she sees the effect it is having on me.

"I'm far too old now to give a damn about what others think, baby. I knew you were wearing my underthings when you were at home with me well before your eighteenth birthday, well before that pervert next door started petting you. I wanted to say something then but you were too young. I didn't want an abuse charge on me while you were still under my roof."

She laughs, sips her drink.

"I knew about your sissy ways, knew you were playing with that little thing thinking about me and my lingerie. Weren't you? Watching me fuck men in my room through the grate in the floor, I think we established that, didn't we? And it never made me stop, did it? I actually liked that."

I stare back at her, silent, stunned, mesmerized. We are out to dinner. We do this often. But tonight she told me she had something special to say to me. She said to me, 'Sit and listen...don't speak.' Just before she started to talk she told me to 'Sit and listen, don't say a fucking word.', her exact words to me.

She's been talking, asking questions she wants no answer to for almost half an hour. We are in a crowded restaurant. She is on her second glass of wine.

"I know about you, little boy. And now you're old enough to know about me. We are going to know about each other, count on that. I mean really get to know each other"

She sits back, looks at me. The waiter comes to the table. She asks for another glass of wine, tells him to bring me more water. I sit silently as he leaves to get her order.

"Now you're going to say one thing and one thing only. You can choose to say something else but if you do we stop this talk, go back to being the dear old normal mother and boring normal son the world sees."

She smiles at me, laughs, leans forward and puts her hand on top of mine.

"Say 'Mama, I love you and want to follow your direction and guidance. Please make me your dirty little boy.' Say it."

She sits and stares, caresses my hand.

"Say it!"

I hurry to repeat and say what she told me to say. I feel choked up slightly as the words spill from my dry mouth. I feel my face redden. I feel like the entire restaurant hears my words to her. She says nothing, just smiles at me.

"This is going to be good, baby, real good. You're old mama has some interesting ideas about you and what you need. Not to mention what I need. And we're both adults. You know your ex-wife and I are very good friends, don't you, have been ever since your divorce. We've discussed you at length many times. She thinks you need a strong hand too. I can give you the strong hand you need. I intend to give you a very strong hand."

She's not old at all, far from it. She's attractive to a fault. Men check her out constantly. She is a very sexy fifty-five year old woman, looks thirty-something. She laughs, catches the attention of the couple at the next table. The waiter brings her wine.

"And mama can give you a very soft hand too. I can reward my little boy if he pays close attention to the rules. Would you like that, baby? Tell me you'd like mama to touch your little dick with her hand. Go ahead, honey. Tell mama."

I start to stammer, talk softly so that only she can hear, feel my face flush bright red.

"Mother, please...don't, not here..."

"Say it! You know it's true. Say it!"

"Yes, please. Please, I want that so bad. I want you to touch my penis, I do."

My ex-wife has told her everything. I know that now. She knows about my fantasy life concerning my mother. She's told her all about me, it's obvious. And no my mother is going to exploit that.

"I know, baby, I know. We'll get to that in time. You just concentrate on being mama's good boy. Don't you worry. I'll touch your penis."

She giggles, very girly. She sips her wine.

"I'm going to go to the ladies room. I'm going to pee. I'm also going to put my hand all over my pussy after I do that. When I come back to the table I'm going to present my hand to you. You're going to kiss it right here in front of all these people. It will be our little secret, baby. Will you do that for your mama?"

"Yes, mother."

I look around the room, my eyes darting everywhere, seeing all that I think KNOW. I hear her chair move as she stands.

"Good boy."

She says that loud enough for the couple at the table next to us to hear. They glance at her, at me.

She is wearing a tight dark red skirt, pencil skirt just below her knees. It accentuates her perfectly round and beautiful rear end. I hear her black spike heel boots click on the floor as she walks away from the table. Her hair is up in the back, large hoop earrings bounce as she walks. Men turn to look at her. They always do. I sit and internalize what is happening.

I've fantasized about my mother for years. I masturbated thinking of things she has done, heard through her bedroom door when she was with a boyfriend, seen through the heating grate in the floor from my basement vantage point when I still lived at home with her. Now at thirty-five years old I still think about her, shared all of that with my now ex-wife. She used to tease, have me call her 'mother' when I would fuck her sometimes. She has told my mother everything. I feel embarrassed, choked up, feels like everyone in the room KNOWS, is watching me. They KNOW. My mind races.

She returns to the table.

She smiles as she passes her right hand across the table to me. I can smell her feminine scent as I kiss her hand. She doesn't pull her hand back, keeps it front of me face. I kiss it again. I can taste her.

"Is your little thing hard, baby?"

She stares at me, laughs. Nobody hears but I think they do. I am so afraid, soft penis, not a chance it will get erect here. I feel terrified that all in the room know about me and my dirty thoughts for my mother.

"Don't worry if it isn't. Mama likes that too. There are lots of things to do with a soft little sissy boy with a soft little penis, lots of things."

She laughs, pulls her hand back.

"Oh my, this IS going to be fun."

She sits and sips her wine.

"You're not going to get to fuck me, you know. Don't even think about that, sweetie, not going to happen. Mama has a boyfriend for that. And that wouldn't be right. You're not going to be my boyfriend."

She watches as my face goes bright red.

"Mother, please...", I talk softy, so very much don't want anyone else to hear this.

She giggles. She finishes the wine in her glass.

"Here's what we're going to do. You're going to pay that check. Then you're driving me back to my house. And we're going to start a whole new chapter of our lives, baby. You're going to present yourself naked to me. Naked as the day you were born."

She laughs loudly. Sees my face flush, she leans in and talks softly to me.

"Baby, I used to change your diapers. Don't you ever think about being shy with your dear old mother. You let me see what I want to see when I want to see it."

She smiles.

"Might even make you start wearing them again. Diapers that is. We'll see."

She laughs so loud that the couple sitting next to us hear her, stare over at us. They can't hear what she is saying but it feels like they can. My face is beet red. They do see that.

"Now let's go. Let's go get my little boy naked and start his first naughty inspection in front of his mother, shall we?"

She stands. I hurry to help her on with her coat. She touches my hand. Quickly kisses my cheek.

"This is going be very good, baby. You'll see. You trust me. You know I love you, dear. This is going to be very special."

All the way home she was silent, thinking. She just stared out the window as we drove. When we got to her house and I escorted her in. She took my wrist in her hand and led me through the house, all she said was 'Upstairs, move.'

We ended up in her bedroom.

"Perfect!" She's sitting on the edge of her bed.

She stares at me, reaches forward and runs one finger up my naked thigh.

"Do I know my little boy or what? I think so."

I'm standing before her in a pair of her panties. Nothing else, just her white panties, I stood before her being inspected. My soft penis sticks out in the front. I feel embarrassment and shame. But also feel I am unable to say 'no' to her.

After taking her home from the restaurant she led me straight to her bedroom, ordered me to strip naked and tossed me a pair of her panties. She sat on the edge of her bed and watched it all as I undressed.

"Put these on and stand still. You be quiet too. I'll tell you when to talk, little boy. And that's what you are to me, my little boy."

She spoke to me in a commanding voice I'd never heard her use before. I felt her hands roughly grasp me just above my butt, leaning forward on the bed she turns me around by my hips. Taking her hands off of me she sits back on the bed.

"I like it. I like it a lot. You are a very good boy. Attractive and in shape, and you'll make a very cute little sissy girl too. I can tell. You have a nice bubble butt. We're going to have to get you your own girly things, can't have you ruining mine. I'm betting you have much of that already at home in a secret drawer."

I feel one hand come down hard across my rear end. I yelp as the sound of her hand 'cracks' off of the bedroom walls.

"Turn around and look at me."

I turn to see her smiling up at me.

"From now on I want you keep several things in mind. Whenever you come to my house I think it would be appropriate for you to be in panties, to start. That allows me to get at this."

She reaches forward and roughly pulls my panties down on front just far enough to expose my penis. She takes me into her hand.

"And it allows for a severe spanking or whipping to be most effective across a bare or almost bare butt."

I feel her hand start to manipulate me to erection. She stares up at me from edge of her bed.

"See? You like that. Mama knows her little boy, she knows that he likes."

She laughs, sexy and girl like.

"We're making much progress here, honey."

She bends forward, kisses the end of it, smiles up at me.

"And you're going to have some chores to do around here. Even though you don't live with me, doesn't mean you can't help your dear mother around the house."

She leans forward and takes me into her mouth. I wince, writhe as I feel her warm wet tongue bring to full erection. She looks up at me, her eyes wide. She starts to pump, masturbates me slowly full length with her tongue up over the head of it, she sucks my penis. I whimper, feel faint. I start to moan.

She pulls her mouth off of me, sits back on the bed.

"Oooo, please, mother, please..." I don't want her to stop.

"That's what happens to a good boy. Now we're going see what may happen to a bad boy. You want to be a good boy don't you, not be bad?"

My erection bobs in front of me. She runs one finger up the length of it.

"My thirty year old baby boy, look at you."

She laughs loudly. I feel her take me by my wrist and pull me down across her lap, face down. Quickly she starts to spank me hard. I reach back to protect myself, feel her grab my wrist and pull it up behind my back hard. I feel her right leg come down across the backs of my legs and pin me up tight to her. I am held in place.

"Don't you even think about resisting me, young man!"

She starts to spank fast and very hard. I writhe and squirm as my butt is paddled to bright red, me helpless across her lap. I cry out with each hard slap.

When she finishes she pets my butt. Soft and gently petting, her hand moves down and across the curve of my exposed cheeks. Then she pushes me gentley off of her lap, hurrying to me feet I stand in front of her. I am crying softly.

She pulls me toward her, looks up at me.

"Now which do you like better?"

"The first, mama, the first, please...please."

She takes me into her mouth again. She holds me in place by the sides of my hips. I feel her fingers dig into me. She starts to pump. She masturbates me with her mouth, long full strokes. I feel the head of it hit the back of her throat, feel her tongue work as she runs her wet lips over me, she sucks to take me to the edge of cumming.

I start to lose myself to her, fully erect in her mouth. And then she pulls back, looks up at me.

"Don't you dare cum in my mouth, little boy. Don't you fucking dare."

She starts to suck me again. It goes on for over half an hour. She feeds on me. I stare down at her. I see her eyes fixed on mine as she sucks me, drives me crazy with her mouth.

And then it ends. She is satisfied. She pulls back off of me, sits back further on the bed.

"I think that's enough for tonight, baby. Mama found out all she needs to know. I think you did too."

She stands and walks to her mirror, her make up table.

"I'm a mess."

She wipes her mouth on a tissue, reapplies her lipstick.

"Thank you, mother, thank you."

"I was wondering how long it would take you to say that."

She giggles.

"This is our secret, honey, nobody but us, tell anyone and it's over. Do we understand each other?"

"Mother, I won't tell anyone. I'm still in shock..." she cuts me off...

"You'll get over that. And I expect a somewhat more submissive tone from you going forward. I'm your mother."

She turns to me, moves up close and takes my still erect wet penis in her hand.

"It's our secret, baby. Ours. And if anyone else knows it will be me that tells them. Not you. Do we have an understanding?"

"Yes, mother, yes...oh yes."

I feel dizzy, in a trance. She strokes my still standing straight up in front of me hard-on through her soft hand. She kisses my cheek softly.

"Now I want you to get dressed, be a good boy and go home. I'll let you know where we go from here. You just trust me, this is going to be as wonderful as wonderful gets."

She kisses me quickly on the lips, winks at me.

She laughs as she starts to undress. I hesitate as she removes her blouse, see her pretty bra and her beautiful breasts.

"Shoo, away, little one. Hurry along. I need my beauty sleep. You'll get to see all this in time. You can dress downstairs, let yourself out. And thank you for dinner tonight. You are a good son. I love it that you take time to visit your mother, take her out to dinner."

She smiles, winks at me. I gather my clothing and hurry to leave.

I dressed quickly downstairs in her living room, let myself out and went to my car. I looked up at her still lit bedroom window.

All the way home I played with myself, almost came in the car as I was driving. When I got home I masturbated twice thinking about her, thinking about my mother dear. I was addicted. Whatever she wants I will give to her. I thought that as I came the second time, thought about telling her that naked and on my knees in front of her.

That was the how it all started.