The Perfect Age Ch. 05

Story Info
A girly-boy loses a dirty old man but gains a lover.
5.7k words
4.55
66.2k
44
5

Part 5 of the 7 part series

Updated 10/18/2022
Created 08/20/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
keptsissy
keptsissy
2,203 Followers

"Look at you. You're beautiful, honey."

She sits on the couch and stares at me, a big smile on her face.

"You're the daughter I never had."

She laughs, looks adoringly at me. I'm wearing a short soft tight-knit pink off-shoulder dress. White short stack heel summer shoes with ankle straps that show off my pink toenails. And under it all white satin panties with cute little ruffles around back. I'm completely made up, my hair to the side in little points, page boy like, sexy points out in front under my ears. I look like the perfect teen girl in summer dress. Nobody would know that I have a soft little penis in my under pants. Nobody would know that I am a boy.

"I told you. I told you so.", she says as she walks to me. "I told you we could do this, you and me, darling."

There are shopping bags next to the couch, several other outfits strewn about that I've tried on, modeled for her. My mother directing it all, she picks up a pair of thigh high stockings from inside of a bag, a pair of sheer see-through panties too.

"Now these, let me see these, honey. Let's see a big girl look."

She hands them to me. I don't wait to be told, am past the initial bashfulness of dressing like a girl for my mother. She walks back to the couch and sits.

"With the ankle boots, just the boots, panties and stockings, honey, let's have a look. You are a little super model."

She giggles. She sits and watches as I slip out of the dress. I undress and am naked in front of her. My soft little thing sticking up in front bounces slightly as I sit to put on the nylon stockings, panties, and 3" spike heel ankle boots, she smiles approvingly. When I stand before her she seems awestruck. Smiles wide-eyed, she looks me up and down critically.

"You put a short little silk robe over that or cute little dress and any man that sees you will probably cum instantly."

"Mother! I'm still not comfortable with the way you talk to me like that, about sex! Please!"

I feel my face flush. Even though I'm standing in front of my mother in just high heel ankle boots, stockings and panties I feel embarrassed by the casual way she talks to me like this. She is so bold about it all. She loves that she has discovered my femme side and is now grooming it, grooming me to be the perfect girl. She has been hard at work on me, her new 'project' for several months now. She is not so much turned on by all of this as she is marveling at it all. But I can tell there is a sexual thing going on too. I am not resistant to that in any way, felt my little thing stir as she said that. My penis is semi erect in front of me. This makes her laugh.

"It doesn't lie, little boy. You love this."

She looks me over.

"And your boyfriend next door will too."

She says that very menacingly, almost angry. She spits that out, her facial expression changes and goes serious. She is still not comfortable that she's found out I've been 'seeing' him, that he's 'taken advantage of me', as she puts it. She has respected my wishes and not spoken to him about it. But I can't help but feel she will.

"Mother, please! Don't make him uncomfortable, please. You know I like him, like seeing him."

"Oh, I know that, sweetie, I know that. That fucker. I guess given that you are now 'out' so to speak as my daughter rather than my son it had to happen, you had to meet a man eventually. But I'm friends with his wife and I don't like it. I've never liked him anyway. I see the way he looks at me. I know he thinks I'm a whore, the men I bring home. I see him give me his dirty looks."

She is angry, sees me look troubled, look to her. I start to speak.

"Shhhh, I know, baby. We will keep this secret between us girls. But that doesn't mean I have to like it."

She tensely smiled, stared at me. She was looking me up and down.

We have just been shopping. Went to several stores, have been out for hours buying me female things. Dresses, underwear, stockings, shoes, makeup, all of it, I am becoming a girl. It was one of what are now regular shopping trips for my wardrobe, things I need to be femme. And my mother could not be more thrilled by it all. She has taught me to do makeup, shave properly and in short be the perfect 18 going on 19 year old soon-to-be college 'coed'. And she's taken it further. She has supervised my 'night time bedroom wear', as she called it when we went to Victoria's Secret and two other lingerie stores she loves in town.

"You don't have to worry about me. But I'd worry about Judy. She finds out and she'll not only kill him she'll cut his balls off first. Maybe yours too."

"Mother!! Please!"

She saw that she was getting to me, teasing me. She looked at me very calmly.

"Come here."

She motioned with her index finger at me as she said that. She clearly saw the troubled look on my face. I was not having fun with her threatening, insulting what I considered to be my first boyfriend. I have been sneaking to his garage at night while my mother is at work, doing things for him. She hates it but has stayed clear of it all.

She turned me around in front of her, put both hands on my hips and pulled my rear end up close to her face as she sat on the edge of the couch.

"Don't move, honey. Just work with me on this."

I felt her slip my panties down gently. She pulled them down just below my cheeks.

"Spread your legs, push your thighs apart. That's it, bend down a bit."

I did as she directed, felt her hand instantly go up between my legs from behind and grab my penis and balls in one hand. I started to pull away from her, reflex, felt afraid at how tightly she held me. She'd never touched me like this before.

"Stop moving! This is for your own good."

She pulled my penis and balls back between my naked thighs, pulled them back tight, felt like she was going to pull them off. I felt the head of my penis touch the naked crack of the bottom of my butt. She held it all there, held me tight.

"Close your legs. Gently, don't hurt yourself. Close and hold it all in place. You can do it."

I felt her other hand pat my rear. I closed my legs, slightly bent forward, felt my penis and balls trapped and held back so far I could not stand up straight. I felt her take her hand off of me and slip my panties back up over my rear end.

"Hold that there, keep those legs together, young lady. Don't you let that boy thing fall out. You'll get the hang of it, girly girl."

I could hear the smiling in her voice.

"Walk to the chair and then walk back to me. Do not let that slip out. Let's learn to walk like a lady, honey."

I felt her give me a slight push as I hobbled forward. I minced, took baby steps, felt like I wanted to bend at the waist. She watched as I made my way to the chair and back.

"Again."

She sat watching, smiling.

"Stand up straight, stop hobbling. Walk one foot in front of the other, baby, you can do it."

Slowly it happened. I could walk completely upright, tucked tightly. I felt like a super model prancing in front of her. She sat and patiently watched the transformation.

"That won't be possible when you see some big strong man, feel it start to get hard."

She laughed loud.

"Mother!!"

"You love this. Stop acting like you don't. We both do."

She stood and walked to me. One hand on the small of my back, she ran her other hand down over the front panel of my panties.

"You feel like the girl you are down there, little boy. Nothing sticking out in front to give you away, you are all girl."

She kissed my cheek and patted the front of my panties, moved away from me and toward the hall.

"I have to get ready for work. I want to see you in those short shorts I picked out today, the red satin ones. Want to see you with that thing tucked, shorts, bare legs and with the flat heel sandals, maybe with that white blouse tied up in front under your non-existent breasts, girly girl. Humor me. I paid for most of this wardrobe. I should at least get to make a request, no?"

"Yes, mother, you get a request."

I smiled at her, saw her wink back at me.

"I love you, baby. I really do."

She turned to me as she was at the hallway.

"I made a dental appointment for you. You're having your teeth cleaned day after tomorrow. And I have one more request. I want you to wear shorts. Not the girl ones you have there. Wear short boy shorts. And shave your legs before you go. It's time you started showing a little leg here and there."

She looked at me, serious look on her face.

"You want to keep sucking that asshole's dick next door, it's fine by me. But there are much better men out there than him."

"Mother!!"

She turned and walked down the hall.

******

"Your teeth are in excellent shape."

He inspected them as the dental tech that had just cleaned my teeth looked on. He was our family dentist, a man I'd been coming to for years.

"I'd like to see you in my office if that's not a problem."

I looked up at him, somewhat surprised.

"Is there something wrong with my mouth, my teeth?!?"

I felt shocked. He'd never said anything like that before.

"No. I just want to talk with you briefly about long term care, that and your insurance policy now that you're eighteen. It won't take long."

He smiled, squeezed my shoulder.

I followed him down the hall to his office. As I entered he closed the door behind me and motioned to the couch. I sat. He sat behind his desk.

He looked at me and smiled.

"I didn't want to say this in front of my tech but I want to see you after hours, buy you a drink, maybe coffee, dinner, whatever you like."

I looked at him somewhat stunned.

"Seriously, I don't bite, we have much in common and I'd like to talk with you about that out of the office. I want to see you after hours."

He was hitting on me!

I sat back on the couch, way aware of my baby smooth legs in my short running shorts, my white canvas slip on shoes. I crossed my legs, girl-like. I let one shoe dangle on my foot, let it bounce as I looked at him.

"Are you talking about what I think you're talking about? You want to take me on a date?"

He laughed

"Maybe. Yeah, you could say that. Yes."

"Did my mother put you up to this?"

"She made an appointment to have your teeth cleaned. She told me that you are now somewhat open to what I'm all about."

I had no idea our family dentist, was gay!! He is as straight looking as the day is long.

"Don't think those smooth shaved legs are lost on me. They're beautiful and so are you."

"I'm a swimmer! I swim, shave my legs for that reason!"

I felt my face go deep red, almost choked as I said that. I knew he knew I was lying. He sat back in his chair and laughed.

"Well, your legs are very sexy, so is the rest of you. I want to buy you a drink. I want to see you. You won't regret it. Please let me see you after hours."

He looked at me very serious, very sexy look on his face. This was turning me on. He was attractive, cute the way he was looking at me. I liked that he was almost begging. I liked the feeling of being chased. I always thought he looked like a man's man, not gay at all. But now I was seeing him in a whole different light. I liked it.

"Okay. I'll do it. I'll let you buy me coffee. I'm not old enough to drink. I bet you like that."

He laughed loud. He walked from behind his desk to the front of me. He looked down at me. He extended his hand and I took it. I stood. He moved up to the front of me. I felt my penis stir in the panties I wore under my running shorts.

"You really are cute, feminine. Has anyone ever told you that?"

I said nothing, felt my face flush. He reached down and ran his finger up the inner thigh of my right leg, felt his fingers trace up and down the front of my shorts. I could see him start to breathe deeper.

"I've thought about you for some time. Couldn't say anything, you were too young. But your mother told me that not only were you older now but that you're more open minded now too."

I felt his hand move to my penis, outside my shorts. I didn't stop him, felt myself get instantly wet, little erection rise up in my panties. I felt his finger trace it.

"Tomorrow evening? Meet me at 7pm? Maybe coffee at my house? Why go out. We can get to know each other better at my place."

I felt his hand take my penis, hold it with his fingers through my pants. I almost fell down, swooned, felt weak. I fell against him. He put his arm around my shoulder, held me.

"Yes...oh...uhhhh, yes..."

I was melting!

"Good then. I'll have my receptionist give you my personal cell number and address."

His hand stroked me slightly, very gently. He felt my penis get harder in his hand.

"You're small. Like a boy, I like that, like that a lot."

He took his hand off of me. I felt his other hand trace down my back. He patted my butt, squeezed it. He moved to the door. He left me standing there almost ready to fall to the floor. I was totally hot, so turned on by this man.

"You won't regret this. I can tell by that little thing in your pants you like me already."

He laughed. I blushed. My face turned bright red.

I said nothing, hurried passed him to the desk, trying to cover the erection in my shorts. I took his number and ran out of the office as fast as I could. Couldn't help but think his receptionist KNEW. I don't know if she did or didn't but she gave me a very sly smile the whole time she wrote his contact information down.

******

"You'll thank me later. Just go see him. He's a nice man, a fun man too. I've known about him for years. He's not your typical gay man. He doesn't play with a lot of faggy boys. I know him and know his ex-boyfriend too. They're both very responsible, grounded and professional men, baby girl. They are the kind of men you should be meeting, getting to know. And he has money. You'll find out that that is major plus in a man."

She is staring at me from across the dining room table. I confronted her on 'fixing me up', told her I was shocked, felt like she'd thrown me to the wolves. I felt like she'd pulled the cover back for the world to see.

"Besides that, are you going to tell me you don't find him attractive? You going to tell me that you've never thought about him? I'd have dated him long ago if he weren't gay!"

She laughed loud.

"He's cute. And he's safe. I know that about him. He's clean, safe and takes care of himself. Did I mention the word 'safe'?"

"Mother, I'm just shocked that you set me up. My own mother."

She rose from her chair, walked to me. She quickly slid her hand down inside my shorts. Felt her take my penis in her hand, I started to pull away slightly. She gripped my penis tighter. She took the back of my hair and held it tightly.

"You just sit there and listen to me, honey. Don't you dare pull away from me."

She started to run her index finger around the hole of my penis while holding it with her fingers, held my head by my hair with her other hand. She bent forward over me. She had never touched me like this before, never played with me. I was transfixed, felt myself go hard in her hand. She kissed my cheek.

"I've seen you naked, seen you girly, sissy like. I've seen this little thing at just the hint of being naked in front of me get all wet. You are a sissy. I know you, little one. Don't I? Don't I?!? Tell me. Tell me that you are a sissy."

She shook my head, reached up and slapped my face gently. She took me by the hair again.

"Yes...uhhhh...yes, mother...I am a sissy, I am..."

I felt my penis go slippery and wet with pre cum in her hand. She ran her fingers all over it.

"You stop resisting me! I know what's best for my new-found daughter. More than you know, little girl, more than you know. Now, when you go to him all lady-like, the perfect proper little sissy, this will be as I taught you. It will be soft and tucked between your legs. Right?"

I felt her start to stroke it, felt the wet head of my penis run between her fingers.

"Yessss, yess, ooooooo, yessss...mother..."

She started to stroke me fast. She started to masturbate me, her hand all the way down into my panties.

"Good, girl. Now let's do something that's way past due. Something you've wanted do for me. We both know it. Do it. Go ahead, do it baby. Cum for me. Cum in mommy's hand. Do it, honey. Cum for mommy."

She was purring, her sweet whispering next to my ear. She released my hair, petted the back of my head. She cooed. I could feel her breath, smell her hair, hear her seductive whispering sexy tone.

I did it. I came quickly all over the inside of my panties and her hand.

"Now isn't that better? My baby girl, about to become a real woman. Wasn't that a wonderful thing, darling? Think about being with a real man and having that done for you by him."

She kissed my cheek. She squeezed my penis gently as it started to go soft, pulled her hand out of my pants and held it to my lips. She said nothing, just held her hand there.

"Well?"

She held her hand under my nose, back of it covered with my cum. Slowly, I started to lick it, kiss it. She said nothing as I cleaned her hand.

"I think now we have a better understanding, honey. Don't you? Do you have a much better understanding about us, about the two of us?"

She smiled at me as I licked her hand clean. She pulled away when I finished the last of it, went back to her coffee on the other side of the table and sat.

"Yes, mother. I do."

I looked down at my shorts, felt my face turn a bright red, heard my voice sissy like and whimpering as I said that.

"Don't you be embarrassed with me, ever. I'm your mother. And I'll never do anything to hurt you, honey. Now you probably need to go change out of those messy things. And I want to see you pretty before I leave for work tonight. Surprise me, wear something that you'd wear to please a man. Show me, honey. I know what I'd wear on a first date with that man. Let's see what you come up with. You're a girl now, baby. Don't disappoint and remember to tuck that little thing."

She looked at me, just stared with those beautiful eyes of hers.

"I love our new found relationship. You have no idea how much I do."

I stood, went to her. I kissed her cheek. She looked up at me. She saw a tear in my eye.

"You'll probably get used to that wet feeling in your panties, baby. I have a feeling you're going to a very popular girl. And when I do that for you I hope you realize I do it because I love you, not because you are a lover. You'll never be that. I'm your mother."

I felt her hand go to my rear end. She patted me.

"You're a mess, honey. Go get cleaned up, get pretty for me."

I turned and walked to my room, thought about the man I was going to see. I felt my penis start to get slightly hard again, felt it move in the mess I made inside my panties.

When she came downstairs I was showered, baby soft, made up and in red short shorts, almost hot-pants like, cut way up at the sides and low at the waist. They accentuated the crack of my rear and my round butt. I had an off shoulder soft ruffled top blouse and large pink hoop earrings. I wore open toe sandals with pink nail polish, showed off my bare tanned smooth legs. I wore pink lip gloss, way dark eye makeup and large eyelashes with my hair pulled down and off to one side, slightly covering one eye. I thought it was a very sexy look.

So did my mother.

"You HAVE to wear that, dress like that for him. Promise me you will. You are a girl. Nobody would ever think you are a boy, nobody. Very cute, unbelievably cute. Do we have good genes in this family or what?"

She walked to me, turned me around.

"If my boss sees you he'll want you, not me anymore."

"Mother!"

"Like you don't like watching me from the basement anymore?"

She laughed loud.

"I have to run, will be home late. I think he has a new client for me to meet so you should get a very good show later tonight from your little peephole room in the basement. I love having a new girlfriend! I really do."

keptsissy
keptsissy
2,203 Followers
12