The Perfect Age Ch. 02

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I started seeing him regularly. He became my first real boyfriend, more like my Daddy. And I liked that too. Have had a select few men as erotic as he was since then, he was the first. And he was the one that showed me what I really was, showed me the real me. I’d think about him all the time. I’d masturbate daily thinking of what my ‘next time’ with him would be like, what I’d do to please him. I still do.

I still get so hot thinking about that very first time, the time my high school friend’s father made me stand naked in front of him, first time I was completely submissive and in the presence of a real man. We did it secretly in his basement I could not keep from touching myself every time I thought about that day, still can’t. I was hard all the time thinking about that, at eighteen years of age my hormones were in overdrive, I wanted him constantly. I craved the things he’d do to me. I’d sit nightly waiting for him to call me to him with his garage light.

As soon as I saw his garage light go on I’d go to him. That was the signal, anytime after 9pm his garage light went on it was a call to me. I’d watch from my mother’s bedroom window, little dick hard in my bathing suit. That was our ‘cover’ so to speak. I’d wear a bathing suit and if caught I was only there to go swimming in his pool. Nobody would ever know what I was actually there for. Once there, it was off into my special room to prepare for him to become the girl he’d made me into. I didn’t have a hard time doing that, becoming a sissy girl. I had my mother to thank for that.


“You don’t like girls, do you.” She was seated at her makeup table, talking like we always did before she left for work. I didn’t know how to respond to that. This was just one day after I’d been with the man next door. I was terrified, did she know about him, did he tell her? I almost screamed.

“Why, what do you mean?” I was embarrassed, somewhat shocked to hear my mother say that. I stared at her, horror-like look on my face.

“I can remember only one time I ever saw you with what might have been a hint of a girlfriend. And that was years ago, I think you were all of fifteen. That didn’t last, did it?” She continued to apply her eye makeup, not looking at me, looking into the mirror as she spoke. She had a different tone than usual, not friendly, almost scolding. “That girl was gone in less than a month.” She smiled to herself in the mirror.

“Tell me. Do you like boys instead?” She turned and looked at me. I felt my face go instantly bright red. She was in a short half slip, seamed nylon stockings and lace push up bra. White pearl necklace around her neck and her large hoop earrings tinkled against it as she turned her head to me. She was as she always beautiful, was in front of me while preparing for work at her makeup table. She didn’t think anything of it that I saw her like that, never did, I’d been watching her like that for years. “You’re old enough to know whether you do or not, you’re a young man, you’re 18 years old. Do you like boys?” She had a very pointed and direct tone, she scared me.

“No, what are you saying?!? Why are you talking to me like this…”, she interrupted my indignant tone, cut me off in mid sentence.

“Do you think I don’t know about your snooping around in my lingerie drawer? I never thought much of it until recently. I know you look at my things, I’ve known for years. You never quite put them back the way I put things in my drawer.” She turned back to the mirror, started finishing her eyes. I was in shock, only stared.

“Did you think you could wear my stockings and not have me find that out? You stretched them out, lucky I have several pair like that. Who else would wear them? It was you, baby.” She looked back over her eye makeup in the mirror, inspected her beautiful work. “Tell me, do you like boys, want to be a girl?” She didn’t look at me, just kept doing her makeup.

I bolted from her doorway. I went to the kitchen, was short of breath. My mother accusing me of being what I knew I was—a sissy. She knew. At least I thought she did. He told her. He told her! I was shaking. I ran to my bedroom, closed the door. I was in shock, sat on the edge of my bed and cried.

Then she softly knocked on my door and just opened it. She came in dressed for work. She was as she always is, gorgeous, sexy and showing it off. She was wearing a short tight red dress, it set off her black heels and stockings. I knew now that she knew I paid attention to that sort of thing for an entirely different reason than most boys my age would.

“Don’t be afraid of it, not if it’s true. I still love you, honey, you’re mama’s little boy. And if it is true, if you want to wear the things I wear, be a girl, I can teach you how to do that real good.” She sat next to me, put her hand on my leg, stared at me from the side.

I couldn’t speak. I almost fainted, could not deal with this at the moment. I started to cry harder, looked away from her gaze to the xslot side.

“Listen baby, don’t you worry about this, you think about. You don’t have to wear my pretty things. We’ll get you some of your own. Nobody has to know, not unless you want them too. Believe me, I can help you become a real girl, if that’s what you want. What’s a mother for if she can’t love and help her little boy with the things he needs.” She laughed when she said that, not mean spirited, but amused and knowing. She knew what I was. Did she know what I did with my friend’s father the night before?

“Do you have a boyfriend, have you had any experience with another boy? If you haven’t don’t worry about that, there’s nothing wrong with liking boys. I know I do.” She smiled at me. She didn’t know, she did not know! I was almost dizzy hearing all this but relieved to think that she did not know about HIM.

“No.” I looked at her, wanted to crawl under the covers of my bed, hide. “No. Please, I don’t want to talk about this. No.”

“Well, you think about what I said. If you want to play, experiment a little, if you want to be a girl, there is no woman better to teach you how to do that safely than your mother. I’m a girl, honey, trust me on that. I’m a very sexy one.” She laughed and stood. “I have to get to work, almost late. I’ll be home later. And one more thing, I not only know you’ve been stretching out my stockings and underpants, I know you watch me from the basement. You’re old enough now that I can tell you that I know. I’ve known for a long time.”

I looked at her, eyes wide open, my mouth dropped.

“Why do you think I have that mirror adjusted the way I do on my bedroom door, why do you think I moved my bed like I did? Do you think I didn’t know that you go into the basement when I bring a man home? They don’t know but I do. I’ve been down there looking up through the floor register, know that’s what you do and know exactly what you see from that vantage point. I look at it as part of your education, thought it might make you want to be with a girl. I guess not.” She bent down and kissed my forehead. “You think about all this.” She put her hand on the back of my head, stroked my hair. “I think you’d be a better little girl than a boy anyway. I do.” She walked to my bedroom door, “Love you, honey. It’s going to be okay.” She turned and left.

I was stunned, sat frozen on the edge of my bed, had tears on my face, stared at the wall for over an hour, stared at myself in my bedroom mirror. All this happening at once, my eighteenth year, just out of high school, I was learning quickly, learning what I really am.

I knew now that she knew about me. She knew I’d watch her with her boyfriends. She KNEW, was doing it all right in front of me. She knew I liked to dress in her female things, dress as a sissy. But she didn’t know what I did with the man next door. At least she didn’t hint at that,

I was convinced she didn’t know about that. It was still my secret. I had many secrets. That got me so excited to think about just that, my secrets. I masturbated three times that night thinking about all that was happening in my life.

The second time I was with him I didn’t have to be told what to do. I did not tell him about my mother and the conversation we had. But I thought about that the whole time I was with him.


I saw his garage light go on and hurried to him. As soon as I entered his door I walked sissy like to the center of the room. I took off my bathing suit, stood naked before him, let my suite drop to the floor onto my pink flip flops. I stepped out of them. I wanted him to see that I’d shaved completely for him, see that I was baby girl smooth. I wanted him to know I was his.

He smiled, didn’t say anything. Just smiled at me as he walked to the chair I’d masturbated him in two nights ago. He kept smiling, didn’t say a word and sat. He just watched me. Then he slid down his pants, pulled them to his ankles and kicked them off. The sight of his big cock made my little thing start to stand up. He was semi erect, at least three times as big as my me and he wasn’t even rock hard…yet. My little boy penis stood straight up.

“Put these on.” He tossed a pair of panties to me. Took them from under the seat cushion in the chair he sat in, threw them to me. I picked them up off the floor. “They’re my wife’s, she won’t miss them for an hour or so. By the time she’s back home you’ll be long gone with the taste of my cum in your mouth.”

He started at me as I put them on, kept smiling. “And tuck that thing back between your legs. I don’t want to see it.” He watched as I did what he told me to do. So awkward, so uncomfortable, first time I’d ever done that, it hurt.

“I like.” He leaned forward. I was standing in the middle of his garage workshop in red lace panties. Pinching my hard little penis back between my legs, that made me bend forward and push my rear out.

“Thank you, I want to please…”, he cut me off.

“I xslot Giriş think it would be best if you don’t speak unless I tell you to. Like I said, you’re going to be the perfect woman when we’re through with you. Come over here and do what you did last time, jack me off, boy.” He picked up the small bottle of k-y, squeezed it down all over his cock.

I went to him and knelt in front of him. I hurried to do as told. As I started to stroke him he looked down at me, not like last time. He watched me intently. His cock went rock hard as soon as I slid the head of it through my hand. I looked away from him, felt my face turn red. Felt his hard on throb and slide back and forth through my hand, I was still not comfortable, slightly afraid of him. He did not lean back in the chair like last time, was staring at me coldly.

“Look a me!” I hurried to turn my face to him, bright red. I looked into his eyes. “Don’t look away from me. Make me want you. That’s what girls do. I know you like this, don’t play shy with me. And pump slower! You want to make me happy, make any man you do this for WANT you.” He stroked the side of my face. “You’ll learn.” He sat back, smiled. He was breathing deeply but still staring down at me. “Ooooooooo, that’s it. You are better than I thought you’d be.” He closed his eyes.

“I used to watch you at my son’s pool parties, and watched you cutting your mother’s lawn too, in just shorts, your tight sissy like shorts. Saw that sissy-like body of yours, thought about what it would be like to stick my dick in your mouth.” He opened his eyes, glanced down at me. He saw me reach down and struggle to push my little thing back between my legs, had to push my butt so far back to hold my erection in place. It hurt. “I had to wait until now, wait until you were a consenting adult.” He laughed loud when he said that. “I knew what you were, used to jack off thinking about what you did in my basement, thought about making you stand naked in front of me. And when you did it was even better than I hoped it would be. Do know, do you have any idea how girl-like you are?” He patted my head, ran his finger down the side of my face and across my lips. He leaned back in the chair.

“Oh, fuck…yes…ooo…”, he started to lose himself to my hand. “You just keep doing that, do it like you’re doing it now, don’t you stop.” Slid him through a tight little circle I made with my thumb and forefinger, concentrated on the head of it. I didn’t wait to be told, held it straight up by the base with one hand and pumped it with the other. And then I leaned forward and licked the end of it, ran my tongue over the hole, kept doing that for him. I made a tight little point out of the end of my tongue and pushed up and down across the hole of his hard cock. He cried out, “Oooooooo, you little bitch. Do that again, lick it.” I did. He watched as I slowly stroked him, took time to run my tongue over the head back and forth. I was getting used to the taste of him too, I was learning.

And then he leaned forward and put his hand on the back of my head. I knew what he wanted, guided me to it like he did before. I did not hesitate this time, I wanted to do it this time. I had been masturbating thinking about this moment, this chance to do it right. This time I was not going to spill a drop.

I swallowed for him, did what he wanted. He came so hard I almost choked. Swallowed for him as he moaned, pumped my mouth as I held his cock firmly in place with my tongue. I wanted it to go on forever, seeing his hips quiver and feeling his legs tighten in front of me. And then I felt him start to go semi erect in my mouth, felt his spurting against the back of my throat stop.

I could feel my little dick press back against the panties I wore, felt the wet head up between my legs and pushed back against the rear of them. I arched my back, sat back on my feet and looked up at him. I smiled at him. First time I did that, I didn’t spill a drop.

“You are beyond belief, so good at that. You’re better at that than my wife is.” He looked down at me. “Stand up.” I did as he said, stood careful not let my dick slip out, slightly painful, was getting used to that too. Before I could stand completely he took my arm, spun slowly and pulled me down across his lap. Felt like I was light to him, like he could throw me across the room if he wanted too. And then I was laying face down across his knees.

I started to put my one free hand to the floor to support myself, he held my other arm, the arm he had in his hand tight. “Put that arm up, hands behind your back.” I did, my full weight on his lap. “You are like a little girl, this is so much better than I thought it would be. You’re like a baby girl.” Felt his hand take both my wrists, huge hand held me and I knew I could not pull away even if I wanted to. I felt his other hand pet my rear. He petted me like a person would pet a dog, slow and deliberate. He let his hand just brush over the little bit of my erection sticking out between my xslot Güncel Giriş legs from behind and pushed up tight against the back of my red panties. I started to whimper. I moaned for him. He said nothing. He just kept petting my rear end, held my wrists with his other hand.

“Beautiful tiny ass, so cute! Where did you come from…”, he slipped his hand down inside my panties, felt the waist band pull up tight against my stomach when he did that, “…and you’re mine all mine.” His large hand covered my butt, felt it all way across both cheeks, he rubbed me. “I fucked my wife after you jacked me off the other night, thought about this ass.” I felt him guide one finger up and down between the full length of my tight and pressed together little cheeks. I felt goose bumps rise all over my rear, all over my body too. Felt his finger touch the end of my penis as he ran it down to the tops of my legs, made it jump and pull as my thighs were holding it in place.

“I’m not going to play with that.” He pinched the end of it, made me whelp, cry out. “A little sissy like you can do that for herself, may hold you up on your toes by it if I spank you, but don’t think I’ll ever do for you what you do for me, boy.” He pinched my left cheek so hard with his finger and thumb I cried out, hurt very much. “Calm down.” He cupped my rear inside my panties with his large hand, squeezed my wrists so hard they hurt, held me in place as he did that. And then he pulled my panties down.

“Stay still, don’t you move, little boy. Gonna start calling you ‘little girl’ with an ass like this, I’m going to have to think of a girl name for you.” I felt him push his middle finger up between my cheeks. He put the tip of it to my hole. I pulled forward, pushed against his strong legs as he did that. He took it out and slapped my rear. “Don’t move!” I struggled to stay still, put his finger back in place. I could feel the tip of it just at the edge of my tight little hole. Slowly he worked it open, spread me slightly, just ran it slowly inside of me. I tightened around his finger tip but did not pull away. He worked me, put it in just to the first joint of his finger.

“We’re going to prepare you, get you ready for what you’re going to be doing for your man.” He kept massaging my hole, talked to me softly, took his finger out and the put it back just a little bit. He was not using any of the k-y. I moaned, squirmed slightly. He said nothing, put his finger up into to me to the second joint and held it there. Then he started to move it around so slightly, made a tiny circle with his finger spreading my rear as he did that.

“You are so tight, so fucking tight. That’s a good thing, girl.”

He kept me on his lap for almost half an hour doing that, my rear relaxing to his hand. He never forced me to go any further, just his finger half way in. When he pulled it out I almost begged him to stick it back in.

“See? That wasn’t so bad. That’s enough for tonight, don’t want to break it before it’s ready to be used.” He petted my naked rear end again, panties pulled down tightly to just the tops of the back of my legs. “You have no idea how cute you are right now, could do this forever.” He slapped my rear, made me jump. “Get up, sissy.”

I did. I hurried and stood in front of him, stood with the panties down just below my cheeks, penis tucked. He ran his hand up over the front of me, started to feel where I’d shaved for him. He stroked and petted me just about my penis. Ran his hands down and over my legs and then it happened. My penis sprang out, could not control it. My face went red. It was hard, small and hard, couldn’t have been more than 3″ hard, standing straight out in front of me.

“I’m sorry, please…” I hurried to try and tuck it back between my legs. He laughed. Felt him reach up and take my wrist, pulled me gently to my knees. He didn’t wait for me to tuck it back in.

“Come here, baby.” He guided my head to him, his semi erect cock in front of my face, reached down with his other hand and held it up. He was soft but still big. He held it up to my mouth, pushed it into my face. I opened my mouth and felt him grow hard as soon as I took it in. This time he leaned back in the chair and lost himself to me as I sucked his cock for the first time.

I sucked him for a long time. He took a very long time to cum the second time but when he did it was not less than the first time. I liked that. He came just as hard as he did the first time. I swallowed for him as I looked up eyes wide open, looking up at him. I wanted him to see me doing that. I wanted him to watch me. He was lost, eyes closed, saw his hands grip the arms of the chair tight as he spurted into my mouth.

When he was finished I sat back. Shiny lips covered with him. I hurried to put my penis back between my legs. It didn’t hurt like it did before, felt right to have my little erection out of his sight.

“Next time I’m going to finger fuck you, I mean really finger fuck you. You may want to do that to yourself a couple of times before that, practice being a good little slut with that rear end.” He stood, stepped up in front of me. I was looking up at him when he wiped his cock across my lips. I licked it, smiled up at him.

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