The Perfect Age Ch. 01

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Young man begins his journey as a young girl.
5.3k words
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Part 1 of the 7 part series

Updated 10/18/2022
Created 08/20/2011
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keptsissy
keptsissy
2,213 Followers

I'd just turned 18 and it was high school graduation. Most of my graduating class was at the raging pool party at my best friend's house. I lived next door to him and his parent's house was the place to be that day and most hot summer days. I didn't think much about the fact that his dad kept talking to me about 'the future' or that he seemed to be around whenever I went into the house to use the bathroom. We'd been to many pool parties at this house, all our friends were always around, his dad had never paid as much attention to me, not like this.

And when the party was raging, at it's most crowded, that's when he approached me. Told me he wanted to 'speak with me' alone, told me he wanted to me follow him to the basement. I thought nothing of it, followed him to the basement as asked to do. I'd talked with this man for years, felt comfortable with him wanting to talk with me alone.

At that time I was almost frail, not in bad shape or poor health, but small in stature. I think I weighed no more than 140 lbs. and at 5'11" that made me thin almost feminine. The man standing next to me was huge, well over 6' tall and solid muscle. He was ex-military, an former college football player and a man's man.

We were both in bathing suits and it was easy to see and feel his large and dominant presence as he stood next to me in his basement. I wasn't prepared for what happened next.

He slapped my rear end! Slapped me so hard I jumped, sort of whimpered and then cried out loud. That was drown out by the noise upstairs. He was standing between me and the door. I started to move to the stairs, didn't understand what was going on. He took my arm, tight. It hurt.

"You stay here a little longer, I want to talk to you. I'm not going to hurt you. But don't you move, boy. I've been waiting a long time to talk to you about this. You be a good boy and just listen." He smiled and slapped my rear again. That's when it happened. I felt my penis start to get hard. Felt that feeling I got when I would masturbate thinking about the men my mother would bring home, about how some of them talked to her when she was doing things for them. When he slapped me the second time he kept his hand on my rear, squeezed it. Felt him feel me through my bathing suit and then I felt him stick his hand down the back of it, inside my speedo, felt his hand go into the crack of my rear.

I could hear the party upstairs, felt like running for the stairs. I was frozen. "Pull your bathing suit down. Don't even think about it, do it for me! Now!"

I looked at him, shocked, felt like running. I also felt him squeeze my arm so tight it made me cry out again.

"Do it." He glared at me. "We don't have a lot of time, just pull it down."

Couldn't believe what happened next, I did it. Was wearing a tight speedo bathing suit, just pulled it down and exposed myself to him, let the suit drop to my ankles. I could feel the tears in my eyes as I kept glancing to the stairs and then back at him. He said nothing, just stared. He ran his hand over my soft but slightly erection penis. He cupped in his large hand, made me jump to erection. He still covered my somewhat small even when hard erection with his hand, he laughed. He removed his hand. Then he walked around me slowly.

"Nice." He looked back toward the stairs. "You're like a girl. Very nice, better than I thought. You are a fucking girl, girl's ass, tiny balls, this is way better than I'd imagined." I felt my face turn bright red. I couldn't stop myself, I just panicked and bent down and pulled my bathing suit up as fast as I could. He laughed out loud.

"I want to leave, go back upstairs. Please..." I stammered. He said nothing, just stared.

"I saw that, saw your little dick jump when I spanked you, and I saw that little hard on, felt it with my hand. You liked that, boy. That's nice too, very nice." He sat on the arm of a chair, could see his cock through his bathing suit. He was hard too, very hard. He looked toward the stairs, pulled his cock out through the leg of his swimming trunks. I stared at it.

"I could make you kiss this. I'm not going to. Not yet anyway." I looked to my feet, felt my penis start to go soft. I was scared.

"No, please, no..." I was crying fully, had never felt like this before.

"You tell anyone about this and I'll not only deny it, I'll make you out to be a liar, make you out to a little queer boy that won't stop harassing me. I'll make sure you regret it." He looked at me. "You and me, we're going to have an understanding, just between us." He watched me closely. I was looking at him and then at his cock. He put it back into his bathing suit.

He stood, moved toward me. "I know you like this and I know you like what I just showed you. You're going to keep your mouth shut about this, you going tell anyone?"

"No, no, never, I could never tell anybody, please, this is embarrassing, please...", I pleaded. I felt the tears in my eyes, felt my burning red face. "Please don't tell anyone, especially any of my friends. I could hear my voice quiver.

He laughed so loud it scared me. "Tell anybody what? That you pulled your bathing suit down in front of me, showed me your little dick, showed me your ass, tell them that you tried to get my attention, danced and wiggled like a little homo slut, that you bent over and spread for me, that you begged to suck my dick?"

He grabbed me as I started to bolt passed him, felt him put his hand to my chest, felt him push me back so hard I almost fell, he almost knocked me to the floor. He took my arm in one hand and turned me, put his other hand on my cheeks, "Ass like a young girl, you're 18, right, my son's age? You look like a 15 year old girl." He patted my rear, let my arm go.

"Now listen and then you can go. Listen to me. I think I know what you need. I have a feeling about you, you know what I'm talking about. Don't know if any of those men your mom dates have taken advantage of it but I want to." I was shocked out of what he was doing, he knew! Knew about my mother, he knew.

He took my hand, placed it on his cock, outside of his bathing trunks. I winced, did not pull it away. I just let it lay there, felt his hard on. I started to move my hand on him. I could not help myself.

"I'm not going do anything you don't want to have happen." He stepped aside from the door, unblocked my way to the stairs. I did not take my hand off of him. He smiled at me. "See? You're as curious as I knew you'd be." He stepped away.

"You think about it and let me know. You want to continue and be what we both know you want to be? All you have to is show up later tonight in my garage. I'll be there after everyone here is long gone. The light will be on and I'll wait for one hour. If you don't show, this never happened. Take the chance and show up. I think I know what you want. I may be wrong but I seldom am in these situations. I know about little sissies like you. I've been watching you."

I could not stop listening to his voice, loved how he was talking to me, first time I felt that way, ever. I stood and listened, did not move to the stairs. I moved to him. I started to rub him through his trunks, wasn't crying anymore.

He ran his hand up my rear over the top of my bathing suit, felt his fingers glide up the crack of my rear, then go to the front. He cupped my penis in his hand. "You show up in my garage later tonight after your mom goes to work. We'll talk more then." He pinched my little thing through my bathing suit when he said that, hard. He hurt me. I jumped back, he just smiled and pushed my hand away from his cock.

Before I could say anything he walked to the stairs, looked back at me. "You may want to stay here for a little bit, let that tiny dick of yours settle down." He laughed and went up the stairs, looked back one last time, "Good boy. And you're going to make a very good girl."

I was dizzy, stunned, was in shock, terrified to move. I thought everybody upstairs must have known. I also felt my dick get hard thinking about standing in front of this man with my bathing suit down around my ankles. I felt the awesome and submissive addiction of being naked in front of a real man, a man in control. First time I felt that, I wanted more.

I hurried upstairs, made straight for the pool and jumped in. I wanted nobody to see the wet spot on the front of my bathing suit. I could feel his eyes on me for rest of the party. And I liked that. I looked away from him, didn't stare but could not help but be aware of him totally.

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

I lived alone with my mother. She worked as a hostess at an upscale restaurant. She wasn't promiscuous but did have boyfriends. And from the time I started masturbating it usually centered around what I'd hear them doing in her bedroom late into the night. And she did things sometimes with several boyfriends very late into the night. I never knew if she thought I knew she saw these men, she never mentioned any of it.

"Was the party fun, baby?" She was at her makeup table. She always did her makeup in her under things, never cared about whether I saw her in just panties and bra. It had been that way since I was a small child. She thought nothing of walking around almost naked in front of me. She was my mother and had been doing that for years, ever since I can remember.

When she finished her makeup she'd slip into a dress and put the finishing touches on her hair, do her ear rings and perfume. Then she'd leave for work. I don't think she knew that seeing her do the things did not only excite me, it made me want to be like her.

Seeing her in sexy heels, stockings, maybe a panty girdle or garter belt, lacey bra and doing her make up made me want to be that! I wanted to be just like her. I would play in her lingerie drawer when she was not around, fondle her intimate things, even dare to try her panties on, my favorite were her panty girdles. I loved the ones with garters. I'd been doing that for years, making sure to never stain them, at least I though I didn't. She never said a word so I always thought she suspected nothing.

She'd leave for work at 7pm and not get home until past 2am. And she'd very often bring a man home with her. Or have one show up after she arrived back home, sometimes two men. Rarely did they stay for more than an hour or two, they never stayed the night. They would be gone before I'd be out of bed. But there was one man that stayed the longest. And he was the one that would rarely bring a second man with him. The one that stayed the longest amount of time was her boss, the man that owned the restaurant she worked in. And the things she did for him were way different than the things she did for most of her 'boyfriends', as she called them when I was younger.

I'd watched them, would wake up and listen intently. And I did watch. I didn't know what they were doing at first. But as I got into my teen years it was a source of masturbation fantasy, a huge turn on. I even had a vantage point into my mother's bedroom, could see her clearly and all that she did from the downstairs bathroom, could see through a floor heating vent in her bedroom that exposed the mirror on her bedroom door. I'd creep down there silently as I heard her and her 'guest' move from the living room to her bedroom. The living room was even easier to watch but they rarely did anything there other than have a drink, maybe start to make out.

I remember the first time I saw her in the mirror doing what I became addicted to watching, saw her on her knees in front of the man she'd brought home. I was much younger, had no idea what she was doing, kneeling in front of this man, her hands on his hips. It was her boss, he would be a regular over the years, still is. I saw her with her dress off in the same lingerie I watched her apply her makeup in before she left for the evening. I also remember that from the first time I saw her doing what she was doing, figured out what it was, I wanted to be her...not him.

I remember seeing her boss, standing in a business suit. I could not figure out why she took her dress off and he just stood dressed. Saw her head moving back and forth in front of him, saw and heard him moan, heard him cry out as she started to slightly choke. I saw him holding her head, holding her by her hair, not letting her get away from him. I almost screamed out. I wanted to run to her, save her! I thought he was hurting her, he was hurting my mother! And then I heard her laugh, heard her say. "You like that, daddy, don't you. I do that real good." Saw her hand reach up and run down his chest and saw for the first time as she moved to the side his penis. It was in her hand, saw her lick the end of it, saw her put it back into her mouth. I froze. I saw how he looked down on her, saw him smiling, saw how she made him feel, act, look. Could not look away, I wanted to be her.

I also saw the man wipe himself off on the side of her face, put his penis back into his pants and leave, heard her walk him to the door, heard her tell him she had no problem being his 'special girl'. I also knew later on that that money on the kitchen counter was not always from tips, at least not tips from the restaurant. I also learned that he sent some of her 'boyfriends' to her as well as bring others. I learned that later.

"I'll see you when I get home, honey. I may be a little late. But you're always asleep when I get here anyway." She smiled, winked at me. "Always asleep when mommy gets home from work." She'd always wink at me. She'd say that every night before she left. I think she knew I watched her.

She kissed my cheek and went out the front door. She always did that too, "Go wipe my lipstick off you face." She'd laugh, saying that as she left and was out the door. I heard her get into her car in the garage and heard her drive off. Six nights a week, that was how it was.

And then most nights just after she'd leave I'd go to her bedroom.

I went to her bedroom this night and realized something I'd never thought about before, realized it faced his house and that he could probably see my mother and her 'guests' better than I could. The man I stood naked and submissive for could see into that window. All he had do was watch from his garage, from a dark window with binoculars. I sat at the window and stared at his garage. No light on in it.

I never took my bathing suit off after leaving the pool party, didn't want to. It felt erotic to know that he made me pull it down in front of him. It felt like a tight pair of panties. Could I go, could I go to the man that made me strip naked, made me feel like I was his slut for a brief moment? I felt my penis get hard, started to play with myself as I stared at his garage window. It was so dark out. I stared at the black window hoping the light would come on. I wanted to know more about what it felt like to be in front of this man, wanted to know more about what it felt like be like my mother.

It was just past 9pm when the light in his garage went on.

"First things first, boy." He looked at me, seemed cold, aloof. I didn't say a word. He walked to what looked like a closet door, opened it. It was a small storage room. "Come here."

He looked into the room then back at me as I went to him. I was wearing my bathing suit and the flip-flops I put on to walk across the yard to his garage in. "If I tell you to go to this room, close the door and stay perfectly silent you do it. It's our 'safe room'. You stay there until I tell you to come out and then we send you discreetly home. If my wife, son, anyone comes to the garage they won't get in until I unlock it, but then you'll be in here, door locked. Kind of like hiding our little secret in the closet, think of it as your closet."

He motioned to the room. I was still in a state of shock, was hearing what he was saying but was still very much scared and excited at the same time. He brought me back to reality, grabbed my arm tightly.

"Understood, boy?!?" He glared at me.

"Yes, yes..." I felt like leaving, felt like this was a mistake...but could not. I wanted more of him.

"Second..." he moved to an over stuffed chair against the wall and sat, "take off that bathing suit and your shoes. You'll do that every time you come to visit me, you put your things in that room. Move, naked and in front me, right now. I want to see you." He watched as I stared back at him. I was frozen. "Don't be afraid, just do it. And don't keep me waiting when I tell you to do something."

I did as he told me. Felt like everything was in slow motion as I moved into the room, went into it, kicked off my flip-flops and took off my bathing suit. I moved back into the larger work room area of his garage, felt the cool floor against my feet, felt the cool air on my naked rear end.

I walked to him. Stood naked and looked down at him, "Please, I'm begging you, don't ever tell anyone I did this." I felt my face turn red again, felt slight tears in my eyes again. I could not control it. I started to cry softly. "I'm not going to tell anyone, count on that. You're safe here, safe to be what we both know you are." He stared up at me, he was fully dressed, made him even more dominant over me, saw him lean forward. I felt him take my penis between his thumb and forefinger, felt him hold it tight so that I could not pull away. He pulled me up onto my toes by it. "You're going to be a good boy for me and nobody's is ever going to know. Nobody. I'm going to take real good care of you. You are safe with me."

He could feel my penis shrink, saw my balls shrink like from cold water too, felt his other finger rub up over them. "You're going to be mine."

And then said it...said that word.

"Nice." He leaned closer to me, yanked my penis slightly to turn me around. Felt him release it and then felt his hands on my hips, felt him turn me around, spin me. Then I felt his hands spread my cheeks wide, inspecting me for the first time.

"I want you to start shaving, you don't have much hair on your little balls anyway but I want you smooth, girl like. Next time I want that tiny patch of hair around your balls gone, legs too." I felt his hand reach up between my legs from behind, felt him take my penis firmly and pull it back and up. He pulled it into the crack of my rear. He made me bend slightly forward, arch my back and push my rear out toward him, slightly painful. I whimpered.

I felt his fingers run up between my cheeks, petting me, felt his finger at my tiny hole, he circled it with the tip of his finger. "Better then I imagined." He slapped my rear and released my penis. I stood and turned back toward him. "We're going to start with something simple. I want a hand job, want you to jack me off." He looked at me as he stood. "Well?" He stared me, inches from my face as he looked down at me.

"Well what, I've never done any of this before..." He didn't let me finish.

"Undo my pants, take my pants and underwear down, boy. And don't play so innocent. You do what you know I want you to do. I want you to jack me off."

I hurried to unbuckle his belt, unzip him and slid his pants down to his ankles. I looked at him, saw him smiling as I took his underwear down, he watched my face as his big cock sprang out in front of me. He sat back down in the chair, large cock was standing up almost fully hard. "Oooo, I'm going to like you being my little bitch! I can tell."

I looked at him as he sat there, was like a deer in headlights, I was frozen. He took a bottle k-y from next to the chair. "Kneel in front of me." He didn't look at me as I knelt slowly. "You're going to be my little girl, and that's where you're headed boy. You're going to learn to be a girl. I know that's what you are, a sissy girl." His cock got rock hard as he said that, saw him take the base of it in his hand and hold it straight up to me as I knelt with my face inches from it, right in front of him for the first time. He squeezed k-y jelly over his rock hard erection, stared at my face as he did it. I took him in my hand, could not look him in the eye as I did that. I did what he wanted me to do.

keptsissy
keptsissy
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