The Perfect Age Ch. 01

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keptsissy
keptsissy
2,223 Followers

As I pumped him, ran my hand over his erect cock I could not believe how big he felt. Not like my penis, he was big, at least eight or nine inches, huge. I felt him throb as I stroked him, saw him lean back in the chair and lose himself to my hand, heard him say things to me, tell me I was better at this than his wife, heard him moan, heard him make the sounds some of my mother's 'guests' make. I heard that for at least half an hour. Made him squirm in the chair as I ran my hand over the back of the head while with my other hand ran my index finger around the hole. I looked at the clock above his head on the wall, playing with him for at least half an hour. I was learning to please him, learning to drive him crazy.

And then it happened. He leaned forward, took my head in both his hands and pushed me toward his cock.

"Don't you pull away, you just do this...uhhhh, fuck...oooo." I felt his one hand go to the back of my head, hand holding me by my hair on the back of my head and his other hand go toward my chin. Felt him take me roughly by my cheeks with his fingers, He squeezed my mouth, held it tight and open. "Don't you stop stroking me, don't you dare stop...ooooooo...almost there..." I felt him guide it into my mouth..." don't you stop...uhhhhhhhhhhhhhh, fuck!" He pushed himself all the way into my mouth just as he started to cum.

He came in my mouth, held my head in place tightly and came in my mouth. I swallowed as best I could but didn't like the taste, started to gag. I let most of it run onto his lap. I felt the head of it run over my tongue, felt my tongue rub up against the hole as he came. I tried to block his heavy stream with my tongue, tried not choke. He kept pumping in and out of my mouth, all the way to the back of my throat as he milked himself, holding my head tight and my mouth around him.

"Ooooooooo, fuck, that mouth, that sissy mouth, that dirty little mouth...ooo...", he just kept cumming, he seemed to go on forever.

When he finished he pushed my head back off of him, gently, pushed me back onto my knees, my feet folded up under my naked rear end. My mouth was numb. He looked down at me.

"If someone came here now, knocked on the door to get in and I sent you to your safe room, how would I explain this?" He looked down at the mess, the cum all over his legs, some of it on the chair.

He was covered in cum. It was all over him. "I don't know." Felt his cum all over my face too, on my chin, saw it drip down onto my knee, could taste it. I couldn't look him in the eye.

"Exactly, you don't know. You swallow it. Swallowing is what good girls do every time, understood?" He looked at me, "Men don't care if girls like to do that or not. Men don't care if girl's like the way it tastes, they just care that girls do it, that they swallow it!"

He ran his finger up some of the cum on his leg, had it all over his two fingers. He leaned forward and put it to my mouth. I sucked his fingers. Didn't have to be told to do it, I just did it. He did it again, did it until the cum was off his legs and off the chair. Did until I'd swallowed it all.

"Good girls swallow while it's in their mouth, make it part of pleasing their man. And you are going to learn to be a good girl. Your mom's going to think she has a daughter when we're through with you." He laughed loud.

I look up at him, felt ashamed, was ready to beg him not to tell my mother. He shushed me, "Get that towel." He pointed to a towel next to his garage work bench. "Clean your face and clean me up. Hurry up."

He watched as I walked naked across the room, watched as I did as he directed. When I finished with him he stood in front of me. I didn't have to be told. I knelt. I pulled his underwear and pants back up, fastened his belt, I was on my knees looking up at him.

He patted my head. "That was very good for the first time. You are a very good boy. And you're going to be an even better good girl. You don't know this yet but you're going to be passable. A completely passable sissy girl, I can see that quality in you. I'm going to bring it out. And you are the perfect age for that. You're going to thank me for all this someday."

He walked to the safe room door. "I have plans for you, boy. You can think of this room as your 'girl' closet, you're sissy dressing room."

He took my bathing suit and flip-flops from the floor, tossed them toward me. "You should probably be getting home, you have a lot to think about. Remember, tell anyone about any of this and I'll make it so you'll never forget what you've done. Everyone you don't want to know about this will. Not a word, boy."

"I won't tell anyone, I promise, I want to do it right, never done this before, I'm scared of you. I really want to please, don't hurt me." I was stammering again, voice shaking. I started to cry again. I started to sob.

He stared at me, he just watched as I cried on his floor.

"Just be shaved smooth next time. Next time I'm going to put you across my lap and finger fuck you. Think about that when you jack off like we both know you will. I'm going to finger your tight little butt. I'm going to get to know my sissy girl."

He smiled at me. He walked to the garage door. "I know you like this. We both know that. You pay attention to the female things your mom does, you watch my wife when you see her too. You pay attention to how they walk, dress, talk. You think about the things real girls do to look pretty for men. You think about being like they are."

As he unlocked the door and I walked past him he pinched my rear. I did not pull away, I moaned and pushed back against his hand. "Good boy. Now you're learning."

I could feel his eyes on me as I walked back to my house across the back yard, walked slow and tried to be sexy. I knew he was watching me from behind.

As soon as I got home I went to my mother's room. I went to her dresser drawer, the special one with all her good lingerie. I took out and put on a pair of her black lace panties, put on a pair of her stockings, put on a pair of her shoes, the one's she wears for her visitors. I stood in front of her mirror. And then I did something I've never done before. I put on some of her red lipstick. I have done this before but never to this extent, have only worn her panties up until tonight. I practiced walking in her heels, watched myself in the mirror as I did. Tonight I dressed in her things knowing that I want to be a girl for the man next door.

That was the first time.

keptsissy
keptsissy
2,223 Followers
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  • COMMENTS
15 Comments
SissyCrissy6245SissyCrissy62456 months ago

Ohhh Myyy KS, I'm "drawn back" to this thread like a "Moth to the Flame"...or I should say: a "PantyBoi to Hur Lingerie"...going to Mommy's dresser drawer to "explore and relish" in her smooth, SeXy, Foundations "Intimates" and do "naughty things" with them...Mmmm Mommy..."delicious" things!!!

sissy11sissy119 months ago

forever one of my favorite series on here and pretty much the inspiration for my whole account. <3

ytown44514ytown44514almost 2 years ago

This series is very well written and kept my attention throughout. Thanks

SissyCrissy6245SissyCrissy6245over 2 years ago

Ohhh Myyy, what a "dark" naughty start for a young Sissyboy. Straight to the "prime" lingerie drawer...in Mommy's room...Mmmm!!! Then lipstick for the "first-ever time"...the texture, silky sensations and faint "makeup" smell of the "Red"...of course, lipstick. Thanks for a delicious start...definitely the "Right Age" to start hur journey.

AnonymousAnonymousalmost 5 years ago
This one is borderline ...

... but ever so hot! The nature versus nurture argument arises. Was the young sissy always destined to follow this path or was he corrupted at a vulnerable age? Very well told & perfectly paced. 5 stars.

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