Rich Boy and the Old Porn Star - Cover

Rich Boy and the Old Porn Star

Copyright© 2026 by storyace

Chapter 2

Coming of Age Sex Story: Chapter 2 - 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   Shemale   TransGender   Fan Fiction   White Female   Indian Male   First   Prostitution  

“Hi, I’m Venus.” She said brightly in a passably feminine voice. She had great long black hair down her back, and lovely dark slanted eyes. I held out my hand; instead, she took my face in her hands to kiss me softly.

“Mmm, Nina told me you’re a sensual young man, but you have a pre-ejaculation problem.”

I was shocked; I didn’t have a problem.

I thought.

“Yeah, see you’re young, so you stay hard after.” She told me as she swept past me to check out the house. “What will you do when you lose that power?” she asked, twisting her long elegant neck to look back at me sharply. “I have a treatment for it, that’s why I’m here.”

I was relieved; I thought she was here for sex. She was beautiful, I liked looking at her. At the same time, I was terrified. I didn’t want to encounter cock, because I’m not gay.

“Take your clothes off.” She told me with a wave of her hand as she admired the art work.

I was about to protest, when she turned and stabbed me with her dark eyes. She was visually female; I’d kissed that mouth already. And Nina had said I had to do it.

“Go on.” The tall gorgeous transsexual insisted doggedly. “Show me what you’ve got.”

I steeled myself, thought of Nina, and pulled my pants down. My cock hung small and soft between my thighs; Venus stepped close and took it in her hand, her face close to me, her eyes burning me as my rod inflated in her grip. It felt good, so good. I didn’t want it to, it just did.

“Ah, that’s better.” She said approvingly, “I like a hard cock. Oh, your testicles are undescended. Bedroom?”

I’d “matured” my room, so it didn’t look like a kid’s. Still, it was obviously not the room of the owner of this house. Venus strode in on her long legs, glanced around and without a word, accepted the situation.

I was standing near the bed, naked, and quite afraid. My cock was starting to deflate. She looked me up and down thoughtfully, then approached.

“Are you going to be obedient?” she asked.

“Yes.” I mumbled as she put her hands on my face and kissed me again. Our bodies were close, so close I could feel her heat as our mouths became acquainted. Her touch was light, sensual, and I was wonderfully conflicted.

I remembered how it had been the same with Nina the first time we kissed; I’d almost called it off.

Slowly, I wrapped my hands around her slim hips, and pulled her close. Her breasts against my chest, her long fingers stroking my back and ass, her sweet perfume, her wonderful hair ... I was erect, hard as steel before her hand wrapped around it again.

“Nice.” She whispered. “Do you like my face?”

“Yes.” I said honestly, “You have a beautiful face.”

Her smile was radiant, and I realized that underneath her bravado she was quite vulnerable.

“Would you like to put your cock in it?” she asked as her fingers stroked my cheeks and toyed with my earlobes.

“Oh, um ... Yes.” I agreed optimistically.

“Have you ever sucked cock?” she asked me.

“No.”

“Oh baby, you’re in for a treat.” She said confidently. “It’s so good, you’ll love it.”

I didn’t think so; although in the end, I have to admit she was right.

She took off her outer clothing, revealing that she had long stockings on with vertical stripes that accentuated her beautiful long thin legs. Her breasts were medium-large in a black satin bra. And between her thighs hung a small soft penis that I tried not to think about. I concentrated on her lovely face instead. Her eyes, brown and clear.

We lay in bed, kissing and touching for a while. She seemed to like that, and I was thinking that maybe our time would run out and she’d just go. At the same time, I was quite turned on. Her skin was so nice and smooth, she stroked my hard cock and tickled my balls with a beatific smile that I did want to put my thing into.

I squeezed her breasts and sucked her nipples, she laughed and kissed my eyes. I didn’t want to enjoy it with her, it was impossible not to. She was so good looking, so sensual, so female despite her extra bit.

Like Nina, she seemed to enjoy her work; whether true or not, that was what made it good. That was what I was paying for I guess.

She slid down, and fixing me with her sexy eyes, put my hard cock into her mouth.

It was wonderful; I couldn’t escape the reality that I was happy to look at and put my penis into that face. I relaxed, stroked her great thick silky hair, and wallowed in the deep intense pleasure. She looked so different to Nina; the sensation of her mouth was about the same though. I realized that the pleasure was more about who was doing it that what was being done.

“Ok baby, your turn.” She told me, lifting herself up onto her knees above me and holding her half erect cock in her hand with a happy grin.

There was no escape; I had to do it. Part of my education Nina had told me, take the bad with the good, no one would know, except Venus and Nina of course, anyway just do it, I told myself, do it and then Nina would be pleased and she’d come and cuddle with me and let me hold her and fuck her again.

So my mouth opened, and the penis entered.

And to my surprise, it was ok. Alright, I admit it, after a few seconds I started to like it. Yeah, it was hard and hot and filled my mouth, I sucked and she laughed, holding my head between her hands as she thrusted, fucking my face for some minutes.

I was looking up at her sexy face, framed by waves of gleaming sexy hair, her great sexy smile beaming at me as her penis bulged and pushed into my head. The penis wasn’t really important; it was the face, the smile, the inward curve of her waist and her big tits that made her female to me.

“Wow, that’s good.” She sighed, “Ready for stage two?”

She pulled away, and then put a pillow in the middle of the mattress. “Set your ass on here, and pull up your knees.” She instructed. “Come on! Don’t chicken out now, this is why we’re here. You want anal, don’t you? Well, before you give, first you must receive.”

She grabbed my cock in an iron grip, and used it like a handle to put me into position. She sat back on her knees and smiled with satisfaction as she looked at my vulnerability.

“Tell me that you surrender.” She demanded softly.

Oh shit; this was going really far, really fast. I wished Nina was here; if Nina told me to do it, I could do it. I thought of her; and I knew it was what she wanted. Nina had told me that the great thing about anal was how men and women experience it the same way. It was a bridge between the male and female she’d said.

“I surrender.” I whimpered.

“And you want it.” She teased, “You really really want me to penetrate your anus with my hard cock!”

“I really want it.” I claimed.

“Good boy.” Venus smirked as she quickly rolled a condom over herself. She took something else from her bag, a wide plastic ring about an inch around the inside, and she pulled my balls through it.

“How’s that?” she asked as she pulled on my stiff cock, “Doesn’t hurt? Ok, good. Now, the idea is to stay near the edge, good and hard, for a long time without coming. That’s the grail, if you can do that, you’ll be the best you can be. You’ll be able to satisfy your lover, it’s more important than anything. Everyone knows this, yet no one talks about it. Ready? Here we go.”

She held my balls in her hand and went down on me again, only this time she held put a finger in my ass. I was totally surprised at the intensity of the sensation; a hot pulse shot up to my brain, then bounced back to my balls. I was about to come when she pulled her mouth away and pressed a button on a little box in her other hand that I hadn’t noticed.

An electric shock ran through my testicles; it wasn’t very strong, but man did it freak me out! And it stopped my orgasm cold.

With a deep look and a wide smile, without a word, she put her cock against my anus, sliding the tip around for a few terrifying seconds before she pushed against me.

“Relax.” She said with a convincing smile and honey smooth voice, “Relax and let me in. There’s nothing to be afraid of, it’s REALLY nice, so good, the greatest feeling in the world is a hot hard cock up the ass.”

She ran her fingertips over my face sensuously, my cock was throbbing in her other hand, and I felt myself open. Holy shit, what was happening to me? My anal sphincter was forced open, she was HARD, and greased, there was no stopping it! It was like a horror porn movie.

Ok, here’s the worst part; I want to tell you it was torture, but it wasn’t. It felt great. I could feel that cock sliding slowly, gently, carefully, brutally up inside me, penetrating, entering my body as I looked into that sexy beautiful smiling face, one hand on my cock and the other on my balls, and I sort of liquified and my balls contracted.

She zapped me again. I convulsed and shivered; I think the pulse was a little bit longer than the first one.

“It’s a sort of behavioral therapy.” She explained as she proceeded to fuck me. “How does this feel? You like it, don’t you? Just don’t come, I told you that.”

The feeling was intense, so good and so bad, hot, close, maddening. She leaned forward and kissed me, I almost had to come again but was afraid of the shock. Her hard cock pumped me, my guts were bouncing, the sensation at the anus was crazy, unlike anything I’d ever known or imagined, and her hand was jerking me off at the same time. I held her ribs, then her face, then grabbed her ass and pulled her in with each crazy fucking thrust, I had to COME!

“Not yet, Loverboy.” She laughed as she hit my balls with electricity again.

I groaned in agony, wrapped my legs around her, looked into her beautiful eyes, and knew I’d never be the same after she was through with me.

Did Nina know what sort of terrible things Venus would do to me? Was this really necessary, or was my gorgeous lover simply torturing me because she was enjoying herself?

Suddenly, she pulled her rod out of my ass. I felt weird and empty. I was relieved that it was over, and at the same time I wanted more of it.

Venus stripped the condom off of herself, and put one on my cock before getting on her hands and knees.

“My turn, sweetheart. Grease me up and give it to me.” She said breathlessly.

I put some jelly on her anus and smeared it around with my finger as she kept still. She had a really nice ass; just slightly off white, tight and round.

“Go on now baby.” She encouraged me, “Put your hard young cock into me.”

I’d only ever done it vaginally, with Nina. This is why Venus was here, I reminded myself. This was what I was paying for, so I’d better just fucking fuck.

“Oh yes, yes!” she groaned as I slowly pushed my rod into her tight ass. It was amazing; totally different yet just as good.

Her knees splayed out and her hips dropped to the mattress as I carefully fucked her deeper. She seemed to like getting it even better than she liked giving it; which made me wonder; was I the same? I sure enjoyed fucking, yet getting fucked was damn good too.

She was smooth, sexy, I stroked her and kissed her spine, reached around and held her big tits in my hands as I thrusted my rod through her.

She lifted up and pushed back, rolling me onto my back; She pivoted around, throwing a long leg over my face, so she was facing me and on top, grinning down through her great wonderful river of black hair as I held her stiff hot cock in my hand. We kissed, then rolled over so I was above again.

Face to face, we kissed and fucked, my rod hard up her tight ass, her smile, her beauty in my face, her hard cock in my hand as she zapped my balls again and again, the pain and pleasure so perfectly matched that we did it for almost an hour. “I want to come in your mouth.” She told me softly as she lifted herself off my rod and sat on the mattress with her knees open. “Go on, suck me. Oh yes, just like that, baby, just like that.”

She groaned, and held my face in her long fingers as she ejaculated hot sweet semen into my mouth. I ate it gratefully, sucked it all down my throat as I watched the pleasure on her face.

She sucked my cock slowly, her face sliding up and down my rod, until at last she gave me permission to come.

It was the greatest ejaculation of my life; a release of everything, total emptying of my soul, my self, and (obviously) my balls.

“Well, that was fun.” Venus smirked as she got dressed again. She strapped up her genitals, pulled a tight skirt over her ass, and swung her tits into a sexy bra. “I hope you’ll want to continue, you still have a lot to learn.”

I took her in my arms and kissed her passionately. She laughed and patted my face, then her long legs walked out to the waiting taxi, pulling her little wheeled case behind her.

Maybe I was just another job for her, maybe that was perfectly normal sex for Venus. How would I know?

Man oh man, for me, what an experience!

Venus was expensive; I wanted to have her every week as well, and that meant I needed more money. I went on a major offensive, digitizing my dad’s classic porn collection (obviously, he didn’t know I’d found it). He had a rare HD video from 1985 that was banned due to having an underage actress in it. I added the trojan to the file and uploaded it into BitTorrent.

It worked; I started to receive coin. My money trouble was over, I could pay Venus and Nina! Nina came, we talked for hours, we cuddled and made out, kissed and fucked. She told me stories, shared her experience of life and sex. Mainly, sex. Nina loved to talk about it almost as much as she loved doing it.

I could look at her face forever; whether my cock was in it or not. Her voice turned me on too, her smile, even the grey roots on her head.

Then Venus; hard where Nina was soft, young and powerful, gleefully fucking my ass as she held my ankles up in the air. Sucking and fucking, zapping my balls with her torture ring.

She was so beautiful, and always smiling; she just loved getting paid to fuck a teenage Indian boy.

One time, she came storming into the house wearing a short skirt and high heeled boots. “Get on your fucking knees!” she demanded, obviously n a shit mood about something. “Lift my skirt, take my cock out and suck it!”

She grabbed my head and thrusted in and out of my mouth savagely. “How do you like this, boy?” she laughed, her mood easing as I sucked happily.

“Mmmmmm!” I choked.

 
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