The Perfect Age Ch. 04

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Sissy 'girl' is a virgin no more.
3.5k words
4.58
109.7k
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Part 4 of the 7 part series

Updated 10/18/2022
Created 08/20/2011
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keptsissy
keptsissy
2,225 Followers

When I saw the light go on in his garage I felt faint. I had been daydreaming about him, his taste in my mouth, thinking about what it felt like to suck him. Every time I thought about pumping him with my mouth my little thing would get hard. He hadn't fucked me yet, not like I now wanted him to. He'd run his cock up between my cheeks and cum all over my cheeks and lower back but he didn't put himself in me. I wanted that. I wanted him in me.

I was lost and playing with myself, masturbating, fantasizing his huge cock making me squirm, whimper. I was thinking about him fucking me with my legs wrapped around his back, thinking about making him hard as a rock with my little hole, having him take me further. My little sissy penis was throbbing, huge wet spot on the hole.

And then his light went on.

When I saw the light in his garage window I gasped, shuddered. I was in my mothers red panties and heels, staring out the window in her bedroom at his house, staring at his garage. I had her panties pulled down just below my balls so as not to stain them with my wet penis. I pulled them up quickly, wanted to rush to him.

I was into her makeup too. I had been playing at making myself up like she did. I looked at myself in the mirror. She would not be home for hours. I wanted him to see me like this, see me femmed up. I hurried for the door of her room, didn't bother to change out of her things. Then I thought about something, something very hot, felt my penis jump even harder in the panties I was wearing as the thought crossed my mind.

I took some of the k-y lotion she keeps in the drawer next to her bed, pulled her panties down just enough to get my fingers up into my butt. I put some of her k-y up into me and pulled the panties back up over the curve of my rear end. I draped a short robe of hers over myself as I went to the stairs.

I went to him in his garage across the back yard in just heels, panties and robe, felt the cold night air all over me. When I entered his garage he was seated in his chair. The chair I knelt in front of when he had me go down on him. I've masturbated hundreds of times thinking about that, makes my little dick hard to think about him sitting there with his huge erection in my face.

He just stared at me, didn't say a word. I saw him smile ever so slightly. I let the robe fall down and expose just my soft naked shoulders. I went to my usual place before him. I looked to the floor, was so bashful, felt my face flush. I had never been made up for him before, was so afraid he'd find it ridiculous.

I put my hand on my hip and pushed my butt out to the side slightly. Posed for him, I could tell he approved. I arched my back.

"You've come along way, baby." He laughed out loud.

"Turn around slowly, let me see. He leaned forward on his chair.

I did as he told me. Showed off my mother's sexy panties, the curve of my rear end, the heels I wore, my eyes made up with her mascara, my pink lips all glossed up, I showed him all of me. I let the robe fall to the floor.

He stood and moved toward me.

I felt his hand on my back. He took me by my arm with his other hand and pulled me up to him. The size of him towering over me made my heart pound, felt my little thing stand up in my panties and press against him. Then I felt his hand go down into them, his hand covering my little hard on. I felt his mouth on my ear.

"Whenever you come to me you make up like this. Don't you ever come to me again as a boy. You're as beautiful as I thought you'd be. You're perfect like this."

He was breathing heavily, felt him in my ear. I felt his hand cup my penis, huge hand covered me with ease. He wasn't playing with me. He was holding me in place, squeezed it so tight it hurt. Then I felt his other hand slap my butt hard.

"Such a pretty girlie boy, you're mine." He started kissing my ear, my shoulder.

I put my hand on the front of his pants, pushed it up between us. Felt his erection, so much bigger than me, I traced it with my fingers. I slid my hand up and down on it outside of his pants.

He took his lips off of my ear. I felt him take me to his chair, rough, ripping his hand off of my up and out of my panties, pulling me. He threw me down onto the chair cushion. I felt the chair shake as he came down onto the seat cushion with one knee up between my legs. I felt him pull aside my panties. I was afraid he'd rip them. I suddenly panicked, thought about having to explain him and all this to my mother! I didn't move. He hurried to unfasten his belt. His pants came down quickly.

It all happened so fast. He was in me for the first time. Felt his weight on top of me pushing me into the overstuffed chair cushion and seat-back, my legs spread, my hand holding my panties pulled off to the side of my tight little hole, him guiding his hard cock to my rear end, him leaning down with his mouth on mine. He pushed his tongue down my throat, me with my face up to him, pinned to the chair with his weight on top of me. I felt the head of his cock push gently up against my rear and spread my cheeks, felt him finding my hole, his cock sliding softly up and down over it.

And then it happened. I wrapped my legs around his, my high heels up over the backs of his legs. I put my arms around his neck and felt him push up into me.

I screamed out.

"Uhhhhh, oooo, uhhh!"

I scared him. He pulled back slightly. It hurt. I felt him put his hand over my mouth, whisper 'shsssh' in my ear. Felt him push in and pull back slightly again. And then he did it. Pushed all the way into me, he held me by my hair with one hand, his mouth over mine, his big other hand on my rear holding me apart, pulling my cheek so far apart I cried out.

He started to pump long and slow, full strokes deep into me. I started to cry. Cried loudly at first, then softly, kept thinking 'I want this to happen'. I kept saying that to myself, wanted this to happen so badly. I didn't care that it hurt. He paid no attention to my crying. He started to fuck me hard, fuck me for the first time. I was his.

He took his hand from my hair, reached down and cradled my rear end with both of his hands, giving him deeper access to me. He let his full weight come down on top of me. He spread me so wide it hurt. He kicked his pants off of his ankles fast and roughly, raised up quickly and pulled his shirt off, threw it to the floor. He grabbed my rear again fast and so hard I yelped, felt like he pulled apart. He collapsed on top of me again, cock in me deeply, I could hardly breathe.

He fucked me like that for almost an hour. I know, saw the clock on the table.

He was up high on me with one of his nipples in my mouth, I sucked and nibbled him, trying to please him. I winced every now and then when he slammed up against my tiny balls and penis, hurried to move slightly to avoid him, shifting my butt in the chair. He held me so tightly I could hardly move at all. He didn't stop. I was numb after a while, didn't care, just wanted him so bad.

And then he started to pump to cum.

I wrapped my arms around his back, put my hands on his butt, I held him tight into me. I could hear him moaning, grunting, breathing heavy.

When he came I could feel it hit me inside. Warm and forceful, felt his cum explode inside of me, felt his cock push some of it out of my tight little hole, felt it run into the crack of my raised up butt and down onto the chair, felt myself slide in it.

He came in me and then ran just the head in and out past the edges of my hole at the very end. He was playing with me, milking the last of it into me.

When he finished he pulled back out of me fast. Happened so quickly I cried out again, felt his semi erect big cock yank out of me, my little hole slamming shut. He hurried to the top of me, put it to my lips. He took me by my hair. I knew what he wanted. I didn't resist. I took him into my mouth. He was still dripping slightly. He tasted horrible, could taste my butt all over him. I didn't care.

"Ooooo, fuck. You little bitch. Ooooo, yes!"

I felt him reach down and cradle my head in one hand, holding me by my hair tightly with his other hand as he pumped my mouth. Grunting and moaning, pushing his semi soft cock to the back of my throat.

And then he stood quickly. He pushed my head away. He stood in front of me looking down at me, his big soft wet cock glaring at me, some of my lipstick on the end of him.

"You'll get used to that. You won't cry the next time. In fact you'll probably beg for it next time. You will be the perfect little bitch. Won't you?"

He reached down and pulled me up out of his chair before I could answer him. I could feel his cum run out of my burning and sore little hole. I felt like I'd been seriously fucked for the first time. I had. I liked it.

"Those your mama's panties?" He stared at me.

"Yes." I looked at him, hoped he liked what he saw standing in front of him.

"She going to spank that ass of yours for covering them with cum?"

"I don't know." I felt my face flush red. "I'm not going to tell her about this."

"When you come to me from now on you dress like that. Or more fem. I meant what I said, don't want to see the boy in you anymore. You're my little girl now. Do you like that, like being my sissy girl?"

"More than you know. I love that. I want you to think of me as your girl. I'll do whatever you want me to do."

I heard myself say that as if I was thinking it, sounded like it came from another place.

He laughed.

"Don't worry about that. My little girl. Yes. I do own that girly little ass."

He pointed to his cock, soft and laying against his thigh. He reached up and took my semi erect little thing in his hand, pulled me down so hard it hurt. I went to my knees, cried out as he released my still semi erect penis.

"Maybe show me what a greatful little girl you are, maybe if you suck it, make me want to fuck that ass of yours again I will."

I didn't hesitate. I did what he wanted me to do.

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

When I got home hours later my mother's car was in the drive. There was another car behind hers. I felt total panic. I had to go into the house, no avoiding it. I was covered with cum, makeup smeared all over my face.

I hurried quickly to my room, and then to the upstairs bath. She was with a date. I could hear the two of them in her room. I didn't go to the basement like I did many other nights to watch them through the vent in her bedroom wall. Not tonight. I was hoping they would be there a long time, give me time to clean everything up, clean her things and me.

I had been fucked twice. I sucked him to make him hard a second time and he fucked me bent over the back of his chair, butt up high. He fucked me so hard he bounced my feet up off the ground. He literally lifted me up off the floor, kept me bouncing on the end of his hard cock. I was dizzy thinking about that. I could barely sit, was so sore. And I was full of his cum. Deep in my butt, his cum, I could still feel him in me. I loved that, was all I could think about! My little thing was hard.

I hurried to wash and clean my mother's panties. I checked her shoes. Saw some mud on one of them, from the backyard. I felt fear, panic again. I did the best I could to clean them. I went to my room and hid the panties to dry in my closet, her shoes and robe too. I didn't think she'd even notice them gone, could put them back in her room after she left for work tomorrow.

I didn't shower, didn't want her to hear me. I cleaned the make up off of my face. I just went to bed after wiping myself as best I could. I lay there playing with my little erection, thinking about my 'boyfriend' next door, could hear my mother and her lover, thought about me being for my boyfriend what she must be being for the man in her room.

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

I came down stairs early, made coffee and was sitting at the table. She came into the kitchen an hour or so later. She slept in late. Must have been with her boyfriend until early, she never sleeps this late.

"So, you weren't in your usual perch, weren't in attendance to see your mama perform last night? Probably for the best, there are those that would find it strange that you watch me."

She laughed that cute teasing girl laugh she does. She stared at me as she came down into the kitchen, came into full view. She saw my face turn bright red, saw the look in my eyes, saw the shock on my face.

She was in her silk robe, the red one. The robe I wore to the garage next door. And she had on the red pumps.

My heart froze. She just stared at me.

"Do these look familiar, baby? Do they look as good on me as they did on you?" She glared, didn't laugh.

"I can explain...", she cut me off.

"Explain why my red panties are somewhat damp and hanging in your closet, the sexy lace ones you seem to like so much. I'm guessing they were worn with all of this." She motioned across her body with her hand.

"And I'm guessing that this isn't yours."

She pointed to slight stain, cum, on the back hem of the robe.

"Or is it? Do you masturbate on my things? Do you?"

I said nothing.

"Are you fucking the boy next door? Your little pool party friend? Answer me! I always thought you two boys played too quietly some times in the basement."

"No! Mother, please, no." She saw me squirm on the chair across from her at the kitchen table.

"Sensitive butt? You can tell me, we both know what you want to be. I told you, baby. We are going to be like girl friends. You're old enough to get that, way past eighteen years old."

She laughed when she said that. I was six months past eighteen years old.

"I'm not the judgmental mother that some boys could have."

She laughed very loud.

"Not at all, baby boy."

She took some coffee from the pot, turned and stared at me. She put the cup to her lips, sipped.

"Tell me. Who did you get all dressed up for and where the fuck did you go? To his car in the drive, is that where you got this stain on my pretty robe?"

"If I tell you the truth you can not say a word. Not a word!" I felt myself turn bright red.

"And you told me we'd get me some real girl clothes of my own, get me my own makeup. If I tell you I want to do that more than ever will you help me?"

I felt my eyes tear up. I felt afraid, embarrassed.

"Baby, I love you. Of course you can trust me. We'll do that for you. Tell me."

I did. She threw her coffee cup against the sink.

"I'll kill that fucker. Kill him." She stood. "Has he been molesting you all along, has he, tell me!" She came to my side.

"No, this just started, after the graduation pool party. He never touched me, ever. You can't say anything to him. I mean it. I want this. This is all new. But I've never wanted anything more." I started to cry hard.

"Please, I trusted you. Please don't say a thing to him. I'm old enough to do this if I want to. I trusted you! You can't ruin this. Don't talk with him, please mother."

She stood silent, looked down at me. I felt her hand on the back of my head.

"His wife would kill him. I know her. You have no idea. Leave him and take it all."

She laughed slightly when she said that.

She did something strange then. She got very quiet, calm. She went back and sat across from me.

"You're right. You are old enough. You're an adult. It's why I helped you with your makeup, said the things I said to you. I just love you and don't want you hurt, taken advantage of. I'm still shocked, baby. I had no idea. And fucking around with a married man is not easy. You have no idea."

"I've only been with him three times. I can't explain it. I love it. I can't talk about this, feels so bad. I just know I do want it. Really bad."

I was crying softly.

"Don't be ashamed. Mama loves you, stuff happens. Believe me, I know. And I bet you make a very good girlfriend. I saw you all made up and baby smooth. You'll have no problem meeting men, sweetie. But why him?"

She didn't wait for an answer. She stood and got another cup of coffee.

"Does he like you in my things?"

"Yes. A lot." I couldn't believe I said that, almost defiant.

"We have to get you some of your own. I can't have his cum on my things. I don't like that, baby. Don't like that at all. I still should kill him. But I won't. Does your friend have any idea?"

"Noooooo, no! Nobody knows. Just you. Please, please, please..."

"Shsssssh. It's okay. I know about these things. You just be smart about it. Don't ever let him treat you bad. And do not fall in fucking love! There are better men than him out there."

She went back to her seat across from me.

":Okay. We're going shopping. You're first real boyfriend, no matter how sneaky the fucker is, should be a good experience for you. I know it'll be good for him. And you're going off to college soon, be plenty of men for you to choose from. We have to make sure you're up to the challenge. And men are a challenge, baby. You still have a lot to learn about being a girl."

She sipped her coffee.

"After you get showered and shaved, baby smooth top to bottom, we'll go to the mall. You need to start doing that every day. Baby smooth, little 'girl'."

She laughed.

"We're going to the girl stores in the mall and you won't be embarrassed about it. You're a girl now. I know that's what you really want. Going to be the cutest girl on the block when your mother is through with you, go up and get ready."

She looked at me, put her hand on mine. She winked at me.

"Am I an understanding mother?" She laughed. "I think so, a very cool one too."

I stood.

"Mother, I don't think I'll ever get used to us talking like this. I don't."

"Yes you will, sweetie. Yes you will." She was staring out the window toward his house, looking over my shoulder.

I walked to the stair, saw her stand walk to the window.

"Please don't say anything to him. Please, mother."

She said nothing. She just stared out the window as I went upstairs and got ready for my shopping trip.

keptsissy
keptsissy
2,225 Followers
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  • COMMENTS
7 Comments
alicia08alicia08over 9 years ago
amazing

fantastic series written with thought and passion, my clitty was hard from start to finish, please keep them cumming x

RebeccaCherieRebeccaCherieover 10 years ago
Little

Ok. I made the mistake of wearing jeans and a tshirt to read it first time. Went and made myself alittle more Girly with my favourite hair, alittle make, lingerie and a pink dress then locked the door, pulled the curtains and read it and re read dressed as Rebecca. Quite an evening. Thank you. Gorgeous story

AnonymousAnonymousover 10 years ago
Best of the season!

Work that skirt and show some sass!

Here's yo' reward going up your ass!

AnonymousAnonymousover 10 years ago
love it

hey girly you have got to quit waiting so long between chapters we just love your stories

AnonymousAnonymousover 10 years ago
Please

don't wait so long to continue this story. Your such a tease!

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