The Perfect Age Ch. 03

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A sissy learns much from his mother, from his boyfriend too.
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Part 3 of the 7 part series

Updated 10/18/2022
Created 08/20/2011
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keptsissy
keptsissy
2,202 Followers

"Hold still!" Felt his hand come down across my rear so hard I saw stars, wanted to cry out, stifled it as best I could. He slapped me again much harder, loud 'crack' as his large hand came down across my bare butt, made my cheeks quiver.

I pulled forward but could not get away. He had the index finger and thumb of his left hand in a vice-like circular grip tightly around my balls and soft little dick, right at the top of them. He squeezed them, almost separated them from my body. He pulled my penis and balls down against my legs. He held them so tightly I winced. His hand was up between my legs from behind spreading my legs with the huge fist he made, felt his large knuckles dig into my baby smooth upper thighs and crotch keeping my legs spread apart.

He was sitting behind me in his favorite chair with me standing naked in front of him, my arched back and butt out for him to see, inspect, pet, spank. My rear was about a foot from his face as

I stood bent forward like that. When he finished amusing himself by watching me squirm like this, slapping my rear, flicking the end of my penis with his other hand, he took the k-y jelly on the arm of the chair and squirted it up between my legs and up the crack of my butt. He let the plastic bottle drop to the floor after spreading it all over my rear. I could feel the cool jell up between my cheeks, felt it drip down over the tops of my back thighs. I could feel the sting of his hand print rise on my rear end as he ran his hand over it. Then he pulled my balls down firmly, making me bend slightly at the knee, held me in place like that, made me cry out.

I couldn't help myself, tried to remain silent like he likes..."Please, please...don't hurt me, please...I'm begging you..." I whimpered, tried to squirm away from him as he held me.

"Shhhh, not going to hurt you, just stay still. You're going to love this, going to get used to it." He leaned forward in his chair, made me move forward slightly, knees bent. He pushed the middle finger of his right hand up between my cheeks, ran it quickly up and down the full length of my rear twice, could feel the tip of it glide deep into my crack. And then he put it to my tight little hole, pushed it in. I couldn't help myself, shocked me, I tried to pull away but could not. Felt him push his finger in slowly all the way, hold it there and then pull it out.

"That's not so bad, come on baby, just relax, be a good girl." He pushed his finger back in, started to fuck me slowly. "You're like a virgin, like a little girl. Nice."

He held it deep in me and started making small circles with it, spreading me as he did it. I gave in, just stood with my hands on my knees, supporting myself. I just let him do it, said nothing, just whimpered softly, used me like that for several minutes.

He pulled his finger out, gently stroked my right cheek, "Reach back and spread your cheeks. I shouldn't have to tell you that." I did as he told me to do.

The only sound in the room for the next twenty minutes or so was his finger moving in and out of my rear end. I started to moan, started to push my rear back against his hand. I could feel my inner thighs squeeze against the fist he had up between them. He felt my penis start to get hard in his hand. He didn't try to stop me, he let it happen. I loved what he was doing to me.

"See? You like this. You little bitch, I know you like this. Very nice!"

And then he stood, made me pull up onto my toes as he lifted the hand that held my balls and penis up from behind, up between my legs. I was pulled up straight slightly bent forward as he rose up onto his feet. He pulled his finger out of me so slowly, pulled it out so slow, wanted to beg him not to, could feel every part of his finger as it moved out against the tiny circle of my tight little rear.

"Please, don't stop, please..."

He said nothing. I felt him wipe it clean across my rear end, wiped it all over the side of my cheeks. Then he started to move me. He marched me to the wall next to his chair still holding me in place by my balls and erect little dick. I cried out as I moved, whimpered. He walked me to the wall.

He pushed me up against it. "Put your hands up over your head. Keep them against the wall. Don't you move, you just stay like that." He slapped my rear with his free hands, brought up as high as I could, hands above my head.

When he released my balls it hurt. I cried out.

He ignored me. He slipped his shorts down from behind, he was right up against me, felt him press himself up against me hard. I felt his naked chest and stomach against my back, felt his knees come up against the backs of my thighs. Then I felt the full length of his huge erection slip up between my slippery cheeks spreading them apart so wide it hurt. The crack of my rear was covered in k-y, it was so easy for him to split them apart. He was huge, so big. I heard him start to use the crack of my rear, long slippery strokes, all I could hear was the slippery noise of him moving up and down on me, me being pumped hard against the wall. He just took his time, could hear him moan as he pinned me to the wall. He reached up and grabbed my wrists, held them tight up above my head.

And then it happened, felt him almost push me through the wall as he started to cum. He released my wrists and with both hands took my hips. He grabbed me so tight I thought he'd bruise me, lifted me up onto my toes and then an inch or two right off of the floor. He held me like that in place against the wall, came all over my backside and up between my cheeks. He came all over my back too, all over my rear end. I felt like I was floating. I was. He held me off the ground as he finished. He dug his hands into my hips and used me. I wanted it go on forever.

"Oooooooooo, fuck, ooooooo,", he crushed me as he fucked me like this for the first time, "Oh, ooooo...uh, uh, uh, uh...fuck!" He came so hard, could feel it run down my rear, down the backs of my legs, felt his breath on my neck, made me cry out.

"Oh, Daddy...don't stop, don't..." I wanted him just keep fucking me, squeezed his erection between my cheeks so hard, tightened them around him so much it hurt.

When he finished he pulled away from me, let my feet got back to the floor, almost dropped me. He was through with me. I did not move, was afraid to, didn't know what to do next. I could feel him all over me, felt his sweat all over my back. I was covered in his cum, felt the cool air on me as he pulled away. He slapped my rear again as he did, hard.

"Nice!" He went back to sit in his chair, sat and admired his sissy bitch.

His cum dripped down the bottom of my back, my rear, down my thighs, running down my legs, dripping down into my crotch and all over my balls. I liked that, felt my little thing start to stir against the wall.

"Fuck, you have no idea how good that felt." He laughed very loud. "And you have no idea how good you look right how, what an ass! I need a picture of this. Next time." I pushed my butt out slightly when he said that, wanted him to see me do that for him. I reached back and took my cheeks in my hands. I spread my rear him, kept my face to the wall.

"Oooooo, come over here." When I walked to him he reached out and grabbed my wrist, pulled me down onto his lap. I sat, felt his cum all over my rear and all over his strong firm knees as I slid around on them. I looked down at my little dick, saw his hand go down and cover it, cupped my balls and penis. His hand looked larger than large against my baby like thing. Then he slid is hand up between my legs from the front. Felt my legs pushed apart as he put his hand up between them and back to my hole, felt his middle finger start to probe, looking for my little hole. He pushed his finger into me again. I closed my eyes, gasped, was under his control. I moaned softly, felt my penis get as hard as it gets, felt my little thing stand straight up. And then I felt his mouth.

Shocked me, felt him kiss me, push his tongue into my mouth as he took the back of my neck in his hand. I kept my eyes closed, felt him take me like that, was afraid to move, did not want him to stop.

He fingered me like that as I sat on his lap fucked me hard with his hand. He made out with me, French kissed me deep, used me like that until I felt his cock get hard again underneath my rear end. Felt it push up between my legs, up between my slippery thighs. I reached down between my legs and ran my hand over it. His cock was so big that it stood up above the tops of my thighs as I was on his lap, could get my hand all the way around it. I started to stroke him, stroked the head like that until he came again.

He came all over again as hard as he did the first time, all over my inner thighs, my legs, all over my hand. And when he finished he slipped his hand out from between my legs. I felt his hand on the back of my neck, ran it slowly down my back, gave me chills. He petted me as I held his semi-erect cock between my thighs, still so big the head of it stuck up plain to see. I fan my finger over the hole.

He patted my rear. Just kept patting me softly, "You want me to stick that in you, don't you, want me to fuck you." He looked at me. "You wanted me to do that when I had you against the wall, didn't you, you little whore?"

"Yes." I looked down at his cum all over my legs, felt so hot for him. "I think about you a lot, think of you as my man. I want to do that for you. I want you to cum in me."

He ran his cupped hand up the cum on my legs, covered his hand with it. He put it to my mouth and watched, watched as I licked his hand clean. I saw him smile as I did that, ran my willing tongue all over his hand. He talked to me as I cleaned his hand three times.

"You think about me? I think about you too." He laughed loud, teasingly, "Think about your mouth on my cock, think about your ass too, think about you being my whore, my little sissy bitch." I felt my face turn bright red. "And that's what you are now, my whore. That's what I think about. I'm going to fuck that tight little ass good, teach you to just be ready for it with or without lubricant, girl. I'm gonna pay special attention to that tight ass. You're gonna get spanked too. Sometimes that's all, just a good hard spanking on that little bubble butt, send you home afterward to jack off and think about that." He laughed, slapped my rear so hard I almost fell off his lap. He started to stand. I slid off his lap. "I'll send you home to think about me, bitch."

He walked to the workbench in his garage, took a towel off of it and wiped himself clean. "Time for you go, sissy." He took his shorts from the floor, put them back on. "And that's your name, 'sissy'. Was going to call you 'Lisa', that's my wife's name as you know. But you're 'sissy', more appropriate."

He didn't say anything else as I put my swim suit back on and started for his door. As I was about to leave I turned to him, looked at him just before I opened the door. "I'm yours, will do anything you want me to do. I'm going to get a lot more girl-like for you, wait and see. You're going to be real proud of your little girl, you wait and see, Daddy. I love the way you treat me. I do."

He said nothing as I stared at him. I saw him

smile to himself as I left, looked away from me. I closed the door behind me.

**********************

"Hold still!" When she said that I felt my rear tighten, remembered him slapping my butt hard when he said that. When he shouted at me 'hold still!' just before he finger fucked me in his garage last night. I felt my little thing stir.

She didn't see me start to get hard, my robe covered that up. "You need to make the liner as sharp and crisp as you can, it sets off your lips, makes the boys want you real bad. They may even buy you things."

She laughed and I felt her hand tighten on the back of my head as she applied the dark pink liner to my already pink lip-glossed lips. "Hold still, have to get this right or your sexy little mouth won't be sexy at all, baby."

I kept staring at myself in the mirror, did not recognize myself. I was seated at my mother's makeup table. She was making me up for the first time, applying all the makeup skill and technique I'd watched her do for years, do on herself. Now she was doing it on me. I was wearing just a short white terry-cloth bath robe, was naked underneath it. I let it hang off of one shoulder, loved what I saw in the mirror. I was astounded at just how absolutely feminine I truly was. She was so good at this, too! I could not believe it. I was actually a girl, a real girl. From the neck up anyway, did not know who the 'girl' in the mirror staring back at me was but I wanted to see her more.

"Told you, honey, told you you'd be cute." She took her hand away from the back of my head, stood back and off to the side of me, looked at me in the mirror and smiled, "You are a treat! Any man that doesn't pay attention to you would have to be gay." She laughed so hard when she said that, felt my face go red.

She put the lip liner tube top back on and placed it on the table, put her hand on my shoulder. "And you can learn to do this on your own, just takes practice. I did for you what my mother did for me. She didn't do as hot though, she wasn't the understanding mother I am. What's a mother for, baby?" She sat on the edge of her bed, looked at me. "You are the perfect little girl, all the boys are going to want to get your phone number." She smiled, admired her work in the mirror.

The lip gloss and liner tied it all together but the eye makeup was what I could not stop staring at. Dark mascara, eye lashes looked twice as long as they were, deep eye shadow, and the base makeup and hint of blush she brushed on my cheeks, she was truly an artist. I did not recognize myself. I was indeed a very pretty girl. I loved it. But my face turned bright red, could not help it, was embarrassed by all this.

"Don't you get all nervous and uncomfortable on me, this is our secret. I know you like this, I know more about you than you do. And when and if you're ready to go out in the world like this it's okay with me, I support you. You're my son...sort of, well now you're my daughter." She smiled, laughed, "And I love you, honey." She looked at me in the mirror. "And trust me, the boys really are going to love you too. Better get ready for that, when you go off to college, you choose to look like this, you are going too be chased all over campus, hot little chick like you." She talked to the image in the mirror.

She did not know about what I'd been doing with the man next door, had no idea. But she did know that I didn't like girls, knew that I had been wearing her lingerie when she was at work nights. And she pretty much had me figured out, knew that I was a sissy, that I wanted to be a girl, not a boy.

This was the first time after 'the talk', the talk that she essentially confronted me with right here at her makeup table. She asked me if I liked boys instead of girls, pretty much told me I did, that she knew I was a sissy.

And tonight she gave me another talk, right after an early dinner she said she had a treat for me. She told me I was going to learn makeup, said I should be squeaky clean, told me that after a shower I was to come to her room in my robe. She told me that tonight we were going teach me about what boys that like real men instead of girls need to know about being pretty. She said that if I were a real man I would not have been sneaking around like a little sissy boy, sneaking around to wear her under things. She told me that it was time to see the real me, told me it was time to bring out the pretty girl in me and look at that.

I was in a trance through the whole thing but did it, just listened as she spoke, said nothing, did exactly as she told me to do. Her voice was almost hypnotic, she spoke me deeply. Now here I was, completely made up. And loving it! I liked what I saw in the mirror, wanted the man next door to see and like it too. I slipped my robe slowly off my other shoulder, exposed both of them down to my nipples. I wore my robe like a low cut dress at the top, held it like an off the shoulders wrap, exposed my fem like upper body. There was nothing male about me. I saw that now.

"You have much to learn, baby. Have to learn to do hair, walk in high heels, have to learn to act like a lady. And believe me, the more you walk and talk like a lady, the more the boys will want you to be un-lady-like, especially when they get you alone." She laughed hard again, she was seeing the humor in this too. I was seeing the eroticism in it, wanted to be with my man, made up and on my knees in front of him. I felt my penis start to get really hard, it jumped up and almost out of my robe as I thought about that.

She noticed that. "Looks like your little friend likes all this too, I saw that." I hurried to cover myself with my hand as she laughed again. I hurried to cover myself tightly, placed my hands on the front of my robe and pulled it up around me.

"Please, this is all so hard. Believe it or not I like this but hate it too." I looked away from the mirror. I felt my face go bright red again, felt a slight tear in my eye. "How do I do this?!? How do I go out in public, see people I know??? This scares me..." She shushed me, sensed my anxiousness.

"Stop!" She stood. "A lady doesn't cry with makeup on, smears her pretty mascara." She came to me and put her hands on my shoulders. "Now listen. You have to admit, you are what you are. You want to take off the pretty face? Be a man? Want a girlfriend? Or do you want to be a girlfriend?" She bent forward, kissed the top of my head. "I think we both know the answers to those questions." She walked away from me, toward her bathroom. "I have to start getting ready for work. How about you spend some quiet time and get acquainted with the girl in the mirror." She smiled at me, as she went to her shower. "She really is a very nice person."

She looked back at me. "If you do this once a day you will learn to do it that good in no time. You'll be a real lady just like rest of us cute chicks, baby. Trust me. That is you in the mirror, the real you." She went into her bathroom, heard the shower start and then she closed the door.

I sat and stared into the mirror. I also started to play with myself, slipped my hand up under my robe, tiny penis fully erect. I stood, pushed her makeup stool back, let my robe slip off and fall to the floor. Completely sexy little girl with an erection looked back at me from the mirror, 'so HOT!' I thought to myself. I wanted to be this all the time. I wanted to be this in front of the man next door, stood there and just looked at myself, started to run my hand softly over my erection, over my legs, one hand up over my nipples. I was lost. I was so lost that I didn't hear my mother's bathroom door open slightly.

Then I heard her...

"I told you, honey. That's the real you in the mirror." I saw her looking at me, naked, made up for the first time, posing, being the sissy I am.

I quickly bent and pulled my robe back up, hurried to cover myself, pulled it on over my shoulders. My face was burning red.

"Don't be shy around another girlfriend. I can hardly wait to get you dressed all cute and pretty, that's the next step, a cute wardrobe. The boys are going to love you, honey. Trust your mother on that. And it looks like shaving will be easy for you, not much hair on you, you're lucky." She laughed again, closed the bathroom door. I stood in shock, mouth open, could not move for several minutes.

Then I hurried to the living room.

*****************************

When she came downstairs I was sitting on the couch, still very much embarrassed and confused. I looked away from her. She was cute, sexy and beautiful, she always is when she leaves for work.

keptsissy
keptsissy
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