Mother Dear Pt. 09

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Loving son and mother, home from dinner out.
6.8k words
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Part 9 of the 14 part series

Updated 06/07/2023
Created 05/10/2014
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keptsissy
keptsissy
2,211 Followers

"I love this place, baby boy. Every time we dine here I think back to that one fateful dinner, the dinner where this all began. The dinner after I came to your home unannounced innocently enough, wanting to take you out to eat only to find you dressed like a girl and on your knees doing what we bad girls do, delightful."

She winks at me over her wine glass, sips lightly. She laughs softly to herself. Her eyes sparkle with delight as my face turns beet red. She is beautiful.

"Would have been fun enough if I surprised you in girly clothes alone but with a man in the house no less, you with your lipstick all over your chin, him with his big dick in your mouth, walked right in on my son giving a man a blow job. Indeed. That was a surprise. You now know better, you now know to lock your doors, right?"

She laughs loudly.

"And that man pulling his pants up so fast he almost fell over, almost knocked me over as he hurried to your door and out of your house, his face bright red. He couldn't even look at me. I saw his wedding ring. I can only imagine what he was thinking on the way home, your lipstick all over his dick."

She nods her head back and forth, cutely, grins at me.

"Any regrets, honey? I would think a twisted little sissy faggot boy like you wouldn't have any regrets at all."

She smiles, raises her eye brows, sexy, visibly amused. She sits back in her chair and folds her arms over her breasts. She stares at me.

"No, Mother. You know I have no regrets. I love what we do. And I am so addicted to our secret world. I love you, Mother, adore you. You know that."

"I know you do, sweetheart. I know you do. And me likewise, darling little boy, couldn't love you more. I sometimes wonder why I didn't move you in this direction much earlier, once you reached the age of consent that is. After all I knew you snooped around in my underwear drawer early on. My darling boy wanted to be a darling little girl, fondling his mommie's panties and things. Well, now you are, so to speak, you are my sissy girl. My friend Allan thinks so, very much so. And he really is the perfect man for you. I trust Allan, a dear friend. He and I go way back, dear. He's better for you than a bunch of strangers cheating on their wives, no? He's taken a firm hand with you, hasn't' he?"

"Yes, Ma'am. He has."

She leans forward, her arms on the edge of the table. Her breasts push up and out, the hint of lace on top of her black bra visible through the top of her crisp white blouse, buttoned only to the center of her breasts exposing sexy and erotic cleavage. I see the bra I helped her into as I dressed her prior to our trip to this place, her favorite restaurant. I think about her slapping my face as I dawdled while helping her step in the sexy black lace panties she is wearing under her tight skirt, scolding me as I knelt in front of her, her holding the short leash attached to the collar she puts on me when I help her dress, telling me 'Stop staring at my pussy and pay attention to dressing me!'. I think about her allowing me to kiss the crotch of them, kiss her lovely panties, allowing me to smell her scent, just before she snapped my collar and scolded me to help her into her skirt.

I think fleetingly about my milking at her hand several hours ago, stretched out across her lap.

I squirm slightly. She notices.

"Those stripes I put on your butt yesterday must still be uncomfortable. If you'd do like I tell you to do you wouldn't have to be whipped like that."

She takes up her glass and sips again.

"Mother, we both know that even if I did everything the way you tell me to do it perfectly you'd still find a reason to whip me."

I look around the room, slightly uncomfortable on my seat. Even though I know only she and I hear each other and know what we are talking about, it feels like everyone in the room can hear, feels like they all know I'm wearing my locking penis harness and a rubber 6" butt plug inserted in my rear end, all held firmly in place by a tight panty girdle. I feel the slight welts from her riding crop, delivered two days ago, as I wiggle slightly, seeking comfort on the hard wooden chair.

"Yes, we do. Yes, we do. And we both know you'd beg for it if I didn't. You cry much easier than your father used to do. You really are a little baby."

She smiles at me.

"I haven't talked much about your father but he was the one that started all this, you know, this Dominatrix thing I love so much. A complete pervert, your father, God bless him. I loved and miss him dearly. We started our kinky journey before you were even born, honey. So much hot and dirty fun with that man, it all actually started for me with Doris. My first sexy little victim to fall prey to my selfish and dominant side, but I didn't think of it as such with her. She was just a college roommate that I could use for my guilty pleasures. Cute little lesbian girl waiting for just the right woman to come along and exploit her little ass, or should I say her mouth.", she giggles. "I was much amused by all of it. But it was your father, shall we say, that 'inspired' me."

She looks at me, gages my slight discomfort. She giggles louder, teen-girl like.

"You keep moving like that and I'll whip you as soon as we get home. You sit still like a good trained boy! That rubber penis up your butt serves to train you to be a good girl for my friend Allan. I'm warning you, little boy, sit still!"

Her voice a slightly raised whisper across the table, firm, Dominatrix-like, she makes me glance around at other tables to see if anyone heard her. We are ignored, alone to the world at our table.

"Yes, Mother. I'm sorry."

I sit perfectly still. I feel the large rubber life-like cock push up fully and firmly into my butt all the way.

"I don't want you to think that I lusted after you, baby. I didn't, not ever. In fact if this had come up any time other than when it did I'd say it was crazy, wouldn't think we'd be doing what we're doing now in million years. But given my wonderful sexual libertine kinky S&M past history, well it was too good an opportunity to let pass by and not to seize the moment with you, lover boy. My baby boy, my baby lover boy, in reality my sissy girl, this all turns me on very much, honey."

She laughs so loud that the next table looks over. The couple sitting across from us smiles at us. It appears to the outside world that we are having fun, a Mother and son out for dinner.

"Your father built that room in our basement. I know you know that, that room that's now yours. I guess you could say he left it to you, your kinky inheritance. He spent many hours down there being given the treatment he begged for, treatment I came to love delivering and thought that he deserved. I found out very quickly that he had no limits. Sort of like you. Like father, like son. But it was my delightful Doris way back in college that released my inner sadist. That little bitch still makes gush."

The waiter comes to our table.

"I'm going to have the Delmonico steak with almond green beans and a wedge salad to start."

She is glancing down at her menu. She deliberately moves the corner of the large menu up from the table, just brushes across the front of the waiters pants, up and then down over his penis. An innocent mistake to the eyes of anyone that caught it, nobody did. The waiter looks into her eyes, smiles. She smiles back at him. She knows him. She has been here too many times to count. And he has been in her bed almost as many times He fucked her for the first time in his car at a Christmas party here at the restaurant a year ago and has been her part-time lover ever since.

As the waiter turns to me she looks up at him, pushes the menu toward him.

"He'll just have water. He's watching his weight."

I look to the table, feel my face flush red. The waiter takes the menu from her hand, takes mine up off of the table. He turns to her and smiles warmly.

"Yes, Ma'am. I'll put your order in right away."

As he leaves she smiles at me.

"My friend Allan loves that smooth baby butt of yours. So does his friend that came to see you last week. Allan tells me that his friend will be seeing you regularly. We don't want you losing your girlish shape, honey. Mother knows best. Now that you see the men I send you to you have to think seriously about these things. They expect you to be cute, girl like. You listen to your Mother about all of that. I know about these things. I know what girls need to do to be at their feminine best for their mail suitors."

She sips her wine, glances about the room.

"The entire time you were growing up your father and I were so fucking kinky, had a select group of playmates, kept it all away from you. You had no idea. And that was hard. I know you didn't know about us, went out of our way to shield you from it all. Your father was my complete and total slave, honey. I could cum by whipping him, seeing him cry and whimper. I have to tell you it was a revelation different from my girlfriend Doris. And he begged me to do it. I learned quickly that there's a market, so to speak, for dominant Mistress girls like me. I was a quick study. I told your father early on that if I played his 'stupid little games', and that is exactly what I called it when we started, when I first indulged him in his kinky fantasy, that it would be on my terms not his, that his fantasy would become mine totally. I had no idea at the time just how accurate a statement that would be. I became as addicted to it all as much he was, more so. I was never so turned on and empowered in my life. I went all in, became the perfect Mistress."

She reaches across the table and puts her hand on top of mine.

"Do you remember your 'Uncle Frank'?"

I think about my Uncle Frank, always came to the house when I was very young, always friendly to me but didn't spend much time visiting with me or my father. My Mother and he would go out, sometimes stay home and spend time in her room upstairs away from us.

"Frank was your father's boss, baby. I still think about how hot that man made me, how on wet he kept me pretty much all the time."

The waiter came to the table, served my Mother her salad. He filled my water glass. As he did she reached up and touched his hand. She looked up at him and he bent forward toward her. She whispered something I couldn't hear. He smiled at her, said 'Yes, ma'am.' and left.

"Your father was my cucklold and husband slave for almost ten years, Frank my lover. Frank is in Florida now, maybe I should drop him a line someday, see if he's still got that magic touch."

She started delicately eating her salad.

"I'm not trying to titillate you, honey, just giving you the background on our somewhat unique family history. Now you don't remember this, you were too little at the time. But one time I was with Frank in my bedroom, on my knees in front of him going down on him. I remember it vividly, was really working on him, lost to it all. Your father was supposed to keep you busy and downstairs watching cartoons. You came upstairs and if I hadn't heard you on the stair and closed the door you'd have seen your dear Mother with Frank in her mouth, you'd have seen me get cum shot all over my face. He came as soon as you were at the top of the stair, barely got the door swung shut when he exploded. That would have been most improper."

She smiled at me.

"I'm not making you uncomfortable, am I?"

She seemed genuinely concerned.

"No, Mother. I love everything about your, our sexuality. I do. I really do."

"Good, because as I told your dear father, I'm all in. There is no turning back now, baby doll. Your father spent two days in his punishment room for that, for letting you upstairs. He couldn't sit for a week. And Frank told him if he ever disobeyed me again that he would deliver the whipping personally, slapped your father across the face several times. Frank never wanted anything to do with your father sexually. He only wanted me. I loved that, get wet thinking about that. We shielded you from it all. It wouldn't have been proper to expose you to an adult sexed up world, sweetheart. But now that we are all adults here, well that's another story."

I feel the toe of her shoe run up my leg under the table.

"I just got very horny thinking about Frank and the things we did. I may have to use that cute little mouth of yours when we get home. We'll see."

She smiles at me, feel her shoe run up my leg, toy with me.

"Tell me you love me."

"I love you, Mother. I do. I am so addicted to you and what we do. Please touch me when we get home, please."

Even though she milked me hours ago I still feel my penis strain at its cage.

"I said we'll see."

She starts to eat her salad.

Two hours ago I was across her lap. She was sitting on her 'milking stool', as she calls it, a large leather padded ottoman. She had a rubber sheet, a baby diaper changing sheet, across her lap. I had my panties pulled down to my ankles, my sissy pleated skirt house dress up over my back. I presented myself to her as I do regularly now for my milking. She had on blue latex rubber gloves as she always does for this procedure. Lying face down across her lap, butt up high, I felt myself wince as her fingers matter-of-factly spread my butt cheeks, her other hand pushing her middle finger down and into me, searching for my prostate gland. She finds it instantly now. She makes me submit to this regularly and always before she sends off with her friend Allan. I get turned on thinking about her doing this to me but not while it is happening. I hunger for the dirty and submissive feeling I get thinking about being naked across her lap but it is a most uncomfortable feeling, like having to urinate badly, when the actually 'milking' takes place. And it ruins any chance at orgasm. There is no climax feeling at all as she milks the semen out of me, makes it run and drip onto the rubber sheet across her lap, catching it all between her legs. She always talks to me when she does this. She coos and baby-talks to me, 'Oooo, good boy, that's a good boy, I can feel it, honey. Such a good little boy, pretty little boy.', and on and on. And always after I am milked dry she watches as I kneel in front of her and clean up my mess, lick the sheet clean, the rubber sheet carefully layed out across her lap so as to not spill any of it onto the floor. This is ritual she gets wet doing. It pretty much always ends in me licking her to orgasm after she raises her dress or skirt and presents herself to me, usually from behind with my face up into her rear as she kneels on hands and knees on the large ottoman facing away from me, her favorite position for me to service her in.

"You know my current boyfriend would have a heart attack if he knew about any of this. I like that. I love having secrets. He's a straight arrow to a fault. But he serves a purpose. The man is gifted to say the least. And he's not demanding, pretty much an on call lover. And although not huge, he's adequate. I sometimes wish I could give you to him like I give you to my friend Allan. He'd have a heart attack if I even suggested it, never see me again. The man is too damn straight. But he comes in handy once a week or so."

She sees my face flush, laughs loudly at the way she is making me feel.

"Oh, honey, we're far to far down the line for you to be uncomfortable with your dear old Mother's sexuality and dirty talk."

She laughs again.

"He doesn't have as big a dick as that that waiter over there does, and that young waiter boy goes several times, but he's stable and he gives me things. But I do love younger men. They can get it up more than once. I bet you like that about younger men too."

She winks at me. She sips her wine, holds her glass up for the waiter so see. He hurries to fill her glass.

"Where were we, baby?"

"You were telling me about my father."

"Your father was the perfect 'M' for my 'S'. Your father begged for abuse, a real submissive, your father. And Frank fit into that too. He was very domineering with your father, at work and out of work. I remember times in your father's office, I'd go to visit Frank sometimes, you were away at school, and Frank would have me go down on him while he made your father watch. He made your father stand and watch, sometimes make him put his nose to the wall as I did that. And your father never complained, ever. He knew better. Frank told him if he ever bothered me about any of what we did he'd forbid me to touch your father's penis, that and whip him. We loved dominating your father as much as he loved being our little slave boy. Your father was the perfect submissive. All of this kept your daddy hard and sexually excited constantly. And isn't that what it's about for us too, baby boy?"

She smiles at me.

"Like I said, 'like father, like son', both addicted to my hand, addicted to mama's loving touch."

"I am, Mother. You know that. I think about you masturbating me constantly. I can't help it."

"And doesn't that work well for both of us."

Her steak arrives at the table, her salad plate cleared. The waiter smiles at her, another 'knowing' glance. He leaves.

"Tell me your favorite part of all this."

She stares across the table at me as she cuts into her steak.

"You, Mother, everything about you. I used to masturbate as a boy thinking about you, thinking about you in your lingerie. I'd smell your panties in your lingerie drawer and get instantly hard. I came in my pants several times just fondling your things."

"I'm surprised you never confessed to me. I'd probably have done something about that. Hind sight is twenty-twenty, you delightful little sissy boy."

"I hate when you whip me but think about it all the time. I fantasize you doing it to me. But when it happens I hate it. I can't say 'no' to you, Mother."

"No you fucking can't. And this works two ways.

I love doing that to you. And the reason is because of just that, you can't say 'no'. I own you now more than I ever did. And we both know that's a very good thing, don't we?"

She stares at me coldly, winks slowly.

"Yes, Mother."

I feel my penis strain at its locked restraint, feel the rubber 'erection' in my rear end. I am hopelessly addicted to her.

"I may stroke that little tiny penis of yours when we get home, maybe put it in my mouth. You have no idea how cute you are to me right now. Oh my, I just made myself wet. We'll see. You just sit there and think about all of that."

She giggles. She starts to eat her steak, looks perfectly content, perfectly beautiful as she enjoys her dinner.

******

An hour later we are back at her house. I am, like so many times before, over the whipping horse in my room in the basement. I am naked, my penis restraint removed and on the table next to the horse, the dildo pulled from my rear and tossed to the floor in front of me.

I am fastened by wrists and ankles to the metal
locking rings in the legs of the whipping horse, pulled tight and down over the leather bar under my stomach. My butt is stretched up and outward, my soft penis dangling boy-like between my spread legs, against the side of the leather covered bar underneath me. I am as always baby smooth to the touch top to bottom.

She paces behind me, her high heels 'clicking' on the tile floor. She takes her time slipping into the blue rubber gloves she wears whenever we are down here in this room. I see it all in the mirror in front of me. The entire room is walled with mirrors. She is wearing the things I dressed her in prior to leaving for our dinner out, all except for her skirt and blouse. She is in 4" spike heel open toed pumps with thin ankle straps, lace top thigh high stockings, small black satin bows at the back of each stocking top, black lace see-through front panel panties with delicate ruffles in the back across her cheeks. The sheer panties faintly show the crack of her butt through them in the back. She is wearing a black lace push-up bra, pushing her breasts up and tightly out in front, hint of her nipples at the top of each bra cup. She is the perfect Dominatrix, the ultimate gorgeous sexual tease.

keptsissy
keptsissy
2,211 Followers
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