tagTranssexuals & CrossdressersA Well Groomed Sissy Boy

A Well Groomed Sissy Boy

bykeptsissy©

"If I receive any complaints I'll diaper you and put you in your dog cage for 48 yours, no exceptions. Do you understand?"

He looks down at me. I feel his dominance over me. I see the look on his face. I start to cry hard.

"Please, Daddy, no. Don't do that to me, please...I'll be good...please..."

I stammer through sincere tears.

"Well then, all you have to do is be a good boy and we won't have to do that. Isn't that right?"

I feel his hand pet my hair. His other hand goes up under my chin and pulls my face up to him. My eye makeup is smeared and dripping, running down my cheeks. Before I can speak, beg, stammer on, he puts a finger to my lips, silences me. He leans forward and kisses me. He French kisses me the way he does, the way that drives me absolutely crazy for him. I feel him pet the side of my face. I feel my soft little penis start to go to tiny erection.

"Shhhhh. We both know what's best for you, don't we? All you have to do is be a good boy, a good little sissy boy cocksucker. We both know you can do that, don't we."

I feel his cum drip and run from my rear end as he sits back in his chair. I feel my tight little hole throb, slightly numb from the hard fucking I just received. I feel the stinging stripes from his riding crop all over my butt. The crop that sits on the table next to him, it scares me to look at it. I think about the severe whipping I just endured for him.

I am wearing only thin ankle strap open toe 3" heels and lace top sissy ankle sox, all pink. My pink toenails show through the shear sissy stockings at the front of my shoes. It's the only thing I'm allowed to wear in my house other than when he has me dress totally femme for him. But for every-day 'dress' it's heels and stockings...and full makeup at all times, that is what he demands in my house. That and a lubricated and slippery tight little rear end. That's all. 'My' house, I call it, which has become pretty much his house.

I cry as I put the side of my face on his naked muscular leg. I'm kneeling in front of him. He's naked and sitting in his favorite leather chair, the one he uses to sit and watch me 'confess' to him in. It used to be a chair I'd sit in. Now I'm forbidden to. He calls it his 'worship' chair. I've just had it 'explained' to me that I'm going to see other men. I'm going to see other men that he sends to my house. I'm not to question his judgement on this. If a man shows up at my house I'm to let him in and do whatever he wants. Whatever and anything he wants, I'm to do it. I've never done this for him or any other man before. I feel scared just thinking about it.

He's huge. He's 6'4", 225lbs, and solid muscle. He could literally pick me up by my arm and toss me across the room. At least that's what it feels like when he grabs me, puts me up against the wall, or pulls me to the floor for fucking. He is pure alpha male and he's been in complete control of me for almost a year now. I'm slight, 5'11, barely 170 and only allowed to be in shape such that I stay tight and firm for him. He has groomed me way passed any 'safe word' and has taken me to total submission to him. I don't even think of saying 'no' to him, even if I wanted to. I am addicted to him, his cock and the way he rewards me with his hand. I have confessed to him that I would live with him and be his bitch 24x7 if he wanted me too. He just smiles when I say that to him, at his request, as part of my devoted confession as I stand or kneel in front of him.

"The first two are friends of mine. You'll get used to it. I showed them pictures of you. I talked you up big time. You should appreciate that. And I had to laugh. One of my friends asked if you suck cock. He said, 'Does he suck cock? Will he swallow my cum? My wife won't do that.' That cracked me up. We both know you suck cock, don't we, bitch? He'll be seeing you this Thursday. You gonna be a good little cocksucker for him? Are you, little boy?"

"Please, Daddy, please, I'll do that for you. You know I will. Don't put me in the cage. Please. I'm begging you. You know I'll do that for you. I'll make him happy. I will."

I cry softly as I say that to him. I feel my butt sting and throb from my whipping. I feel him move my head toward his semi erect and wet cock. He just fucked me hard after he whipped me, me restrained over the whipping horse in his basement. The whipping horse he built, positioned right next to the dog cage he put there, the cage that terrifies me to think about. He did that to make a point. He made me beg to please other men for him, beg to be his whore as he fucked me for over half an hour, hard. I was crying and whimpering the entire time through my pleading words, stretched tightly and restrained at the ankles and wrists over the whipping horse. He used the vicious crop on me first, fifty hard times on each cheek and back thigh. I was crying hard. He ignored it all. Then he mounted me and said softly, 'Beg me to have you fuck other men.' That's all he said before he started to fuck me. He pinned me to the whipping horse as he crushed me with his weight, mounting me from the back.

When he came in me he did it huge. He pushed up as deep into me as he could and filled me. I don't remember him ever more 'turned on', more excited. When he finished he pulled out of me and undid my restraints. He told me that I really am going to start seeing other men. All I could do was sob softly. He led me up off of the whipping horse and up the stairs by my arm.

"I know this will be somewhat new to you, seeing the men I send to you. But we both know you're a whore. Tell me you're not. I dare you."

I looked to the floor. I felt my face turn bright red.

He laughed. Pulling my face up to him, his other hand on the back of my head, I felt my mouth guided to his cock. His erection stood up off of his lap. I felt the head of it slip passed my lips and into my mouth.

"Does he suck cock?", he said looking down at me, in a mimicking teasingly humiliating way.

He laughed hard. I felt his cock grow to rock hard full erection as he moved my head up and down on him. I felt the tears in my eyes, felt my rear end and the backs of my legs burn like fire from my whipping. I felt his cum run out of me and drip down my inner naked left thigh to the bend in my knee as I knelt in front of him and did what he wanted.

"This is a going to be a brand new thing for you. And for me, I love it. And you are going to do it. I think to start you should be ready for visitors on Tuesday and Thursday evenings, say from 5pm on into the night. I can't see any of the men I send to you wanting you for more than an hour or two. If a man knocks on your door you will let him in. And you'll be as pretty as pretty gets, perfect sissy girl candy at the door and ready to please. There may be some lunch time visits too. I've told your first two gentlemen callers that you will not disappoint in the sissy girl department. And you had better not. I mean pretty, they will expect a gorgeous little faggot to answer the door. We both know you are capable of that. I know my one friend likes ultra femme full dress. We know you can to that. He told me he wants no hint of you being a man. That cracked me up, sissy girl. And any man I send to you will be there because I sent them. You remember that. You think of serving me when you service them, little boy...uh, uhh...oooooo, yeah...that fucking mouth...ahhhh..."

He leaned back in his chair and closed his eyes. As he talked he started to lose himself to me. I love taking him to that 'place'.

I had the head of his cock 'trapped' between the roof of my mouth and my tongue, running my tongue over the hole of it in small short strokes. I was lost to masturbating him with my mouth. When he came the second time I felt a strong spurt hit the back of my throat. I held my lips tightly around him just behind the head of his cock and licked the hole of it with my tongue in a tiny hard point. I pushed my tongue into him. This drives him totally crazy. As he spurted into my mouth I swallowed it all.

When he finished he pushed my head back off of him, looked down at me.

'They're going to love you. You'll be seeing them more than once. I know that."

"I want to please you, Daddy. It's all I want. Sometimes you're so mean to me. You know I only want to be a sissy for you. You know that."

He ran his hand over my hair. I tasted his cum in my mouth, felt it on my lips.

"You know you need firm hand. You know you need to be disciplined some times. And you also know it turns me to do that to you. You are my bitch and you know that too. Remember when I told you to lose ten pounds extra and you couldn't do that? Isn't that why you needed me to get you your dog cage? Didn't you being in there for several days help you focus on what I expected from you? "

I remembered being diapered for the first time, put into that cage, remember him locking it as I cried For almost four days all I got to eat was his cum, me sucking him through the bars. I remember the horrible mess I made in my diaper too. I remember the begging and sobbing, begging to be let out. He didn't care. It was the first time I realized that he truly owned me.

He pulled me up quickly over his lap and rapidly started to spank my naked butt. My tight cheeks bouncing with each slap of his firm and powerful hand, he pinned me quickly with his leg over my legs. I cried out with each hard slap. I felt him reach up between my legs and pull my soft little penis back and display it, lay it out on his leg. I felt him start to run his finger around the head of it, up over the hole of it.

"Good boy, such a pretty boy. We both know what you need, don't we, baby?"

He was almost purring to me as he played with the underside of the head of my little thing. I felt myself start to get hard.

"Oooooo, Daddy...yesss, uhhh..."

He kept working me like that. I felt his other hand go to the crack of my butt and push down into me, between my cheeks. I felt his middle finger slip into me.

"Uhhhhhh...oooooooooooooo...yes, please..."

All I could do was whimper, as I balanced myself on his rock hard muscled leg. I felt him start to finger fuck me, slow and methodically. I felt him start to rub the head of my penis between his index finger and thumb against his leg.

"I have two other men in mind. But I have not approached them. These are married men at an age where a lot of married men need a dirty little secret. They have long passed been through with their wives. Most wives won't do what they want anyway. You're going be very much in demand, sweetie. I can tell already."

I felt his finger pull out of my butt and felt him lift me by my arm off of his lap. He stood and pulled me up close to him. He French kissed me deeply as he held me to him. He made me almost faint in front of him. I felt my little erection up against him, felt his hand go to it and start to pump me.

"Are you going to do what I expect from you?"

"Yessss, Daddy, you know I will, you know I will!"

I was lost to his hand, his tongue pushed down my throat, his hand cupping my stinging right cheek.

"You know I will."

He kissed me again and pulled away from me. He put the finger he had in my butt to my mouth. I opened and started to suck it clean. He smiled at me.

"That's my dirty little boy. That's the boy I love and own. No complaints, none. You do what they want. We both know you could not find a hotter man than me. We both know that I know what you need. Don't we?"

I mumbled 'yes, yes, yes' as he finger fucked my mouth with his dirty finger.

He pulled his finger from my mouth and wiped it on the side of my face. He moved away from me and walked to his clothing on my couch. As he dressed I stood and looked at him, my little erection barely 3" standing up and bouncing in front of me.

"I know you'll masturbate after I leave. I don't have time for you to do it while I watch your dirty little show. And we both know that you lose some of your sissy boy submissive edge when you cum, don't we? You had better not let that happen, boy. I've been thinking of getting you a pink sissy dick cage, a locking harness. It would be a good way to control your constant masturbation and the undesirable loss of a good attitude."

"Please, Daddy, no. Please don't do that. Please."

"We'll see." You just be the best little good boy you can be and we'll let that limp little dick stay free. For now."

He looked at himself in my hallway mirror. He snapped his fingers and pointed to the floor at the door. I hurried to him, knelt in front of him.

"Fix your makeup. You're a mess. No man would want that messy face. No man wants a dirty girl."

He petted the side of my face as he said that. I looked to the floor. I felt the humiliation that can bring about with just a few words.

"Do you want to kiss me goodbye?"

"Yes, Daddy, please, please, please let me kiss you goodbye, please. You know I love to do that for you."

I begged looking up at him. He smiled, laughed. He reached down and unzipped his fly, took his cock out quickly and held it out in front of me. He watched as I repeatedly kissed the head of it, small pecking affectionate kisses.

"You are going to love being my whore. You already are but now I'm going to give you to others and make it as real as real gets. We both know it's what you want. We both know it's what you are, a whore."

He laughed when he said that. He slapped me hard across the face with his cock. Then he held it out to my lips. I kept kissing the head of his semi erect cock. He pulled away from my 'act of devotion', my kissing him. He put his cock back into his pants and zipped himself up. He smiled, patted my head and opened my door.

"Bye, baby.", was all he said. He closed the door behind him.

I hurried to my upstairs full length mirror and looked at myself in it. I slowly masturbated. He was right. I was a total mess. I always am when he's through with me. I put k-y on my hand and masturbated super slowly staring at the dirty 'girl' in the mirror. It was what I always did after he left. I thought about being a real live whore for him. I was never hotter. I knew more than ever he was the perfect man for me. I came into my hand, watching myself in the mirror, concentrating on keeping my submissive state of mind, keeping it completely. I overcame instantly my natural 'loss of submission' feeling I get upon cumming. I felt even more the owned and shameless sissy that I am. I licked my hand clean as I repeated in my head...'You are a whore, you are a whore...', over and over as I cleaned my hand. And then I did it again, masturbated a second time, all through it 'chanting' to myself what I am. I am a whore.

After I came the second time and cleaned up my mess I went to my makeup room and redid my makeup completely. I tied a tight pink ribbon up around my tiny balls, made a big bow on top of my soft little thing, pushing it all out in front. I looked at myself in the mirror at my makeup table. Huge smoky dark eyes, huge lashes, superhot pink lip gloss and deep red liner, I was exactly what I was meant to be. Exactly. I stood and turned, looked at my butt and the whip marks on me. And I felt that I didn't want to be anything other than that. I felt my penis stir as I thought about my doorbell ringing next Tuesday evening, a complete stranger entering my house. I thought about being the perfect sissy boy, made up, dolled up, and ready to be used. And I thought I wouldn't want to be anything else for my man.

I could taste my cum, his cum in my mouth. I could still feel his cum in my butt, still wet on my inner legs. I slipped into a pair of shear ruffled panties to keep his cum there. I looked at myself in the mirror. I am exactly what I was meant to be. Exactly.

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by Anonymous

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by Jennytheodor05/23/18

kinky

asusual, your stories are a great turn on...
but wish the humiliation part to be higher... you increased our expectations lol

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by aurelietv7805/11/18

Extraordinary !

Well written, and so exciting story!!
Love so much your stories, please continue this one !

kisses
aurelie

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by justincbenedict05/10/18

It's so intense

I leave my heterosexuality at the door when I read your incredible stories of the little fag who has the big man come to his house...wow

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by sissygirl12305/10/18

missed your stories

I love your stories and have read them all my tiny sissy clitie is always soft but my sissy pussy is moist and just quivers waiting for my bf hard cock.

look forward to more

hugs

sis

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