Rich Boy and the Old Porn Star
Copyright© 2026 by storyace
Chapter 1
Coming of Age Sex Story: Chapter 1 - A sexualy frustrated teenage US Asian boy has access to a computer and lot of money. After several call girls refuse, sexy and famous old Nina agrees to come over and see to his needs. She'll change his life, for a price.
Caution: This Coming of Age Sex Story contains strong sexual content, including mt/Fa Heterosexual Fan Fiction White Female Indian Male First Prostitution
I grew up rich. We had a big fancy house on an expensive US city street, my parents they gave me everything except their attention. I had tutors and coaches, I might have even had a wet nurse. Yeah, I was used to having money to buy whatever I wanted.
I was home alone for the summer when I was 15. I was watching a lot of porn, and found a website with expensive call girls; That was when I decided I wanted to get laid. They were only a few thousand dollars and a few were in my city.
I was shy with girls; my mind would go numb and my throat dry when suitable ones were around. Ok, I was a bit weird, a social misfit. I had money though; at that time, I was sitting on around $50,000 in bitcoin.
I went online, chose an attractive woman in my area, and called her. There was a credit check, and then she wanted to talk to me over a video link.
“Yeah, I don’t think so.” She said dismissively, broke the connection, and blocked my access to the whole website.
I went back to pornography and masturbation for a while, intermittently looking for a hooker who would take my money.
I made a new identity and went back to the site where porn stars and playboy girl prostitutes advertise. One in my area was Nina; she was really old though. I downloaded her videos and jerked off for a couple of weeks. She was so sensual, I loved the way she touched and kissed.
Her advertisement said she did “coaching”. She took my call!
I wondered if it was really her I was talking to?
“You know my rates?” She asked.
“Yes, that’s not a problem for me.” I told her, “It’s just that, um, I’m not going to lie, I’m uh, young.”
“You sound mature enough.” She said, “I have a ‘don’t ask, don’t tell’ policy. Are you disabled or something?” she asked kindly, “Obese?”
“No.” I told her, although my weight was on the borderline.
“Then why do you need me?” she asked.
“I can’t talk to girls my age.” I said.
“Rajeev, are you masturbating right now?” she asked me.
“Yes.” I admitted.
“Have you downloaded all my movies?”
“A lot of them.” I told her.
“The later videos where I’m old?”
“Yes.”
We got onto a video link. Fuck! It was really her! she was wearing big glasses and she was in her 60’s, but she was real!
“Oh. You’re REALLY young.” She laughed; she didn’t break the connection though. “I can’t take your money, Rajeev.” She told me, “I’d like to help you, it’s just that I could get in really big trouble.”
“I could pay with bitcoin.” I offered.
She laughed again; man, that was just so sexy. “You’re so sweet! I tell you what, I can’t accept money, but I’d meet you if you make a donation to a women’s charity for ten thousand dollars.”
“Ok.” I said.
She laughed some more, I don’t think she believed me.
Two weeks later, two women got out of an uber car in front of my house. Nina is really small, high heels and a long dress, with fake blond hair and fake tits.
The other woman was larger, with short hair and wide shoulders.
Shit! What had I done? I was terrified. What if my parents found out? Well, they’d never paid any attention to me before, why should they start now?
I opened the door and we all looked at each other for a moment. Nina smiled; and her smile seemed real.
She was really old. She was still attractive though, despite large glasses. She has huge blue eyes that bug out just slightly, her skin is very white, teeth even and straight. She was dressed like a woman you’d meet in an office, and had a great figure; a small waist and a moderate ass.
“So, you’re the teenage millionaire.” She said, holding out her hand, “I’m Nina, this is George, my security.”
George nodded to me and entered first.
“I hope you don’t mind.” Nina said, sweeping in past me, “I’m a little bit paranoid. Now, I’d like a coffee.”
She took off her jacket, revealing a short tight summer dress over patterned black stockings. She wore boots with 2” heels. She sat back on the sofa with a total confidence that just oozed sex appeal. She looked straight at me with those big blue eyes and smiled; all my doubts vanished.
I loved her! I mean, you know, not forever romantic love. I loved her for the moment, for being a sexual goddess who looked into my eyes and talked to me. Who seemed to see me.
We talked as George methodically searched the house, and swept for electronics. I’d disabled the wifi as requested.
“Tell me everything about yourself.” Nina said, crossing her pretty legs and smiling at me with her pretty face, “Relax, everything is good.”
She had a way of putting me at ease. She’s a real professional, more than a whore. She advertises as a therapist and teacher.
“Sit down with me.” She told me, and then she took my hand. The first sexual touch of my first lover.
“Look me in the eyes.” She instructed, “Good. Are you happy right now?”
“Very happy.” I said.
“Then you need to show it, dear. Smile, that’s better. Move a little closer. Are you afraid? I am! Hah, you’d think a woman with my experience would be used to it by now, but even with George in the next room I’m nervous. That’s part of it you know. Now, talk to me. Tell me your story, convince me that you really want me here.”
She looked at me though her big glasses with her big blue eyes, her mouth curled into a sincere little smile that somehow pried open some door in my mind that had always been closed.
Words started to come out of me, spilling into the room. Nina smiled and nodded, made small comments and asked the occasional question. Her fingers moved just slightly against my palm; the sensation was maddening, I was more excited than I’d ever been in my short life.
Mom was a software engineer, Dad had an import-export firm. I was an Asian kid in a 95% white school, I was socially awkward, self conscious about being overweight, and generally a loner.
I was clever though, good at computer stuff. I’d sold some gaming assets and bought the bitcoin when I was 12.
Nina rotated away from me, then put a foot on my lap.
“Take my shoe off.” She instructed me kindly, “And gently massage my foot. That’s a good boy. Tell me, do you have a large cock?”
“No.” I admitted.
“Is that why you think you need to pay for sex?” she asked without apparent judgment.
“No; I just don’t know how to talk to girls.” I said, “Girls I like don’t like me.”
“I like you, and you’re talking to me.” She pointed out, “Run your thumbs up and down under the arches, not too hard. Yes, that’s very nice. You may stroke my legs up to the knees. You know, I’ve been with over a thousand men but only one or two virgins. When I was your age, my lovers were old men. Wealthy old men. Anyway, I don’t think we can go beyond this. I know you made a big donation to my favorite charity, and I appreciate that.”
I didn’t say anything; I was sort of numb. I had my hands on her, she was a genuine porn star, she was here in my house! I wanted to make love with her more than I wanted anything ever, yet I knew it was very unlikely. I was happy with just massaging her small white feet.
She looked at me in silence for a minute, and then reached under her skirt and rolled her stocking down her milk-white thigh, and took it off. Then she took off the other. Her feet were soft and clean, toenails painted red.
I stroked her calves in silence, looking at her face.
“What do you feel?” she asked.
“You’re really pretty.” I said.
She laughed; “So are you.” She said, “You don’t believe me? Well, it’s true. You have kind eyes. A lot of the men who I meet with are not nice. These days I’m more discriminatory, I only work with guys I like. Kiss.”
She stretched and lifted her right foot to my lips.
“Now run your tongue over it. Suck my toe. Bite it softly.”
As I complied, I kept my eyes on her face; my obedience seemed to excite her.
“You like this, don’t you?” she asked, “Suck each toe, one by one. Oh, that’s good! Run your tongue across my ankle. You seem more relaxed now, your fear is being replaced by excitement. If you trust me and do what I tell you, this could be a really wonderful afternoon. For both if us.”
I just stared at her; I was so turned on, my cock was screaming for release, my brain was numb. The smooth white leg in my hands was more exciting than I knew was possible, the feeling of her toe in my mouth as I sucked was inexplicably different to anything I’d ever had in my mouth before. And when I looked into her face, her easy confident smile, her big blue eyes, I knew I was safe.
Nina was a professional. She knew just how to play me, she understood that I needed to be lead through this. As my terror drained away, I let myself trust her. Obey her.
“Do you want to kiss me?” She asked, “On the mouth I mean.”
“Oh! Yes please.” I answered in pleasant surprise.
She pulled her foot out of my mouth and swiveled upright, wrapping her pale fingers around the back of my neck, her face almost touching. Her white face, old yet still attractive, filled my vision. Her breath was in my throat. Her eyes, god how I loved her eyes, I could look into them forever.
“Now put your hand on my face, gently curl your finger around the back of my head. That’s it, now you have me, see? At this point, if a girl doesn’t pull away, you have permission to kiss her mouth. Go on, carefully pull our faces together. The slower the better, because you don’t want to strike teeth, and it’s more erotic to anticipate the kiss first.”
She had to stop talking, because our lips met then.
My first romantic kiss; I liked it. The sensation of her lips pressing molding, caressing my mouth. Her tongue came out to gently slide up inside, and her breasts pressed against me too. She was so soft, so small and vulnerable. I just wanted to hold her, cherish her, appreciate her. I held her with my hands as we kissed for a long, long time.
Then she suddenly pulled away and stood up.
“Well baby, that’s your time for today. I have another appointment.”
I was devastated. “Really?” I pleaded, looking up at her.
“No, I was just testing you.” She admitted. “It’s important that a woman knows that she can just say no at any time. ANY time, understand? Even if you’re fucking and about to come, if your lover suddenly changes her mind you have to stop. Even if you paid money. Got it?”
“Yes.” I said sincerely.
“Ok then. Where’s your bedroom?”
“Through here.” I said.
She was only as high as my nose now that she was barefoot.
“You don’t have any hidden cameras in here, do you?” she asked me sharply, staring intently into my eyes.
“No, I swear!” I said.
“Ok, I believe you.” She said. “Good, now take off your clothes.” She told me, “Let’s see what you got.”
What I had was a flabby belly and a small cock. Look, I want to tell you I’m six feet tall with a six-pack torso and 12 inch dick. If I was that guy, I wouldn’t have paid ten grand to lose my cherry.
“Sorry.” I said to her.
“For what?” she asked, “You don’t have to be ashamed of anything, baby. Now bring that beautiful big hard cock over here.”
She held out her hand, palm up at the height of my groin.
I smiled at her gratefully. I was hard for sure, beautiful I can’t say, but I knew I wasn’t big.
And then she wrapped her experienced old fingers around my young virgin rod. She smiled into my eyes as she watched my reaction to the unexpectedly intense sensation.
I thought the top of my head would blow off; and suddenly I knew that sex was far more that I’d imagined. A world of sensation was opening up, if I dared feel it.
“Oh, you like that?” she teased, “It’s different to when you do it yourself, isn’t it? Oh baby, just you wait. Aunty Nina is going to show you what it’s all about!”
And she kissed me, standing against my naked body still dressed, her hand gently stroking my rock hard penis.