tagCelebrities & Fan FictionA Night with Hayden Winters Ch. 01

A Night with Hayden Winters Ch. 01

byvelvet hammer©

NOTE TO READERS: This is a fantasy about the lovely, luscious Miss Hayden Winters. You may or may not know of her -- she only just started doing porn a year ago, at the tender young age of eighteen.

A caveat: Although I have bedded girls more than a decade younger than myself, I usually prefer women with some experience under their belt. The truth behind this tale is Hayden's remarkable resemblance to Tracy, my high school girlfriend -- I exploit this angle with a twist at the end of Part 3.

The subject of this fantasy has recently "retired" from doing porn but there are numerous pictures & vid clips of Hayden available on-line - of course! All the usual sex is here - Hayden IS a porn star after all - no violence or nastiness in this one, just enjoyable sex. Please remember as you read this is FANTASY; a work of fiction and is intended for people of the age of 18 or older. Cheers -- Velvet Hammer**

It was one of those late nights like so many nights where I usually end up surfing porn on my machine. I was idly clicking on links leading to images and marveling at the seemingly endless parade of naked female forms. As I progressed in my journey through acres of nude flesh I had to adjust my 'package' a few times, naturally. Things were progressing to the point where I was about to undo my trousers and take it to the next level when suddenly, an image appeared on my screen that stopped me in my tracks.

On the screen before me was a girl -- yes a porn girlie - who was the spitting image of my high school girlfriend! The hair was right; brunette cut to mid-neck level, her eyes were right, even her body was right. She wasn't even naked; she was wearing a pair of lime green panties with white polka dots and a long sleeved halter top thing tied in front. I hit right-click and saved the image to my porn file and on the heat of the moment I dubbed her 'Tracy'.

Tracy was my first love. Tracy gave up her virginity to me - one memorable afternoon, on a thick fluffy sheepskin on the floor of her sister's bedroom. And while we did the dirty deed, Tracy's mother was down with the flu in bed in the next room. I always was a risk-taker.

There was no indication of the young lady's identity -- it obviously wasn't my Tracy, she'd be in her middle age by now. So I moved on in my data- mining of the Internet's vast porn resources, and didn't think a thing of the girl I'd named after my first girlfriend.

You know what they say . . . a man never forgets his First Girl.

About a year went by, and from time to time I'd open my porn file and gaze longingly at the girl I'd named Tracy. I swear she is the spitting image -- right on down to the freckle on her right titty.

Then one day I was surfing porn - the still shots - and there she was again! This time there was a NAME:

Hayden Winters

A quick search revealed scores of images of this lovely young thing; Miss Winters had been quite the busy little beaver in the course of her first year in porn. Mostly solo scenes where she was feeling herself up and diddling herself, and some girl-girl action.

My guess was she'd started out doing some nude modeling for some of those 'art' websites -- the ones that feature high-end photography and HD video of absolutely beautiful young ladies, totally naked with their legs spread wide apart -- and then ventured into some lesbo action before taking her cockteasing to the higher art of masturbation.

Then I hit the motherload.

Hayden Winters sucking cock. Just like MY Tracy sucked MY cock . . . all those years ago . . . Hayden Winters fucking. Just like MY Tracy . . . fucking ME!

The more and more I explored the more images of young Miss Winters became available. Hayden Winters straddling some dude on a sofa. Close ups of Hayden Winter's wet pussy getting drilled. Close ups of Hayden Winters sucking cock. Close ups of Hayden Winter's asshole. Hayden Winters getting pearl-necklaced. Hayden Winters taking a facial.

Of course I had to masturbate to her -- the overwhelming sensory input of this lovely creature performing all these lewd and crude acts, quite openly and without a hint of shame, was simply too much. That and the incredible resemblance to My First Love . . . she was too much to resist.

As I stroked off to watching the wonderful Miss Hayden Winters wrapping her sweet pouty lips around a hard cock, it made me wonder about all the hard cocks my Tracy wrapped HER sweet lips around, over the years since high school? Watching the jizz splatter across sweet, sultry Hayden's lips and chin made me wonder how many cocks did my Tracy suck to completion, how many jizzloads dripped off my Tracy's chin?

I jacked off to Hayden Winters sucking some guy, fucking some lucky fellow. As she took his load in her gaping mouth, across her outstretched tongue I shot a legendary wad four feet across the room.

Now is about the time for me to discuss my . . . < ahem > . . . hobby . . .

As the male of the humanoid species accumulates years, there is a certain . . . < ahem > . . . diminishing of the . . . uh . . . full vigor of youth . . .

This of course has not happened to me to any great significant effect. Not because I am extraordinary but rather because I am very athletic and I do take certain supplements.

Let's put it this way; I don't need Viagra.

Nonetheless, about ten years ago or so I decided to exploit of my years of advanced humanoid sexual studies and research. I began by modifying my diet to advantage my legendary sexual prowess . . .

These days I max out on bananas (good for the banana), egg whites and pineapple juice (good for what comes out of the banana), oysters (I don't have to explain THOSE do I?) Broccoli (puts lead in the pencil) and oranges - LOTS of oranges (improves the taste of what comes out of the banana).

I compound this strict diet with heavy doses of vitamins, specifically vitamin D (for the Dick), vitamin C (for the Cock), vitamin B (for the Balls), vitamin E (for EJACULATION), vitamin F (for FUCKING) and a whole buncha other vitamins and herbs good for the Cock-and-Balls Department.

Since embarking on this regimen, I have developed some remarkable results in the Wadsworth Longfellow department. Between the diet, vitamins and restraining myself to no more than two wads per day (sometimes two days or more between wads) my wad has increased significantly not only in volume but also in viscosity. If I conserve my efforts then tantalize and tease the boner long enough I have been able to achieve some really heroic cumshots.

Let me just say that my wife is a cum freak, and thoroughly enjoys the semen-beauty-facemask treatment I rewarded her with for her memorable blowjobs. The other morning my lady had me lay back while she subjected my cock-and-balls to a particularly delightful tickle-torture-tongue-bath and when she finally let me cum I launched a squid four feet across the mattress.

I should be declared a living treasure. If there was a Nobel Prize for shooting jizzwads I'd be the permanent recipient, of this there is no doubt . . .

. . . but I digress . . .

Back to my story.

I spent a significant period of time researching Miss Winter's body of work and learned that sexy Hayden Winters was born Tiffany Maples, in San Diego, California. Hayden started out in the adult industry at age eighteen -- I already knew that -- by the time she was nineteen she'd already made the transition to explicit hardcore pornography.

There was only one more thing to learn.

These days you can find out anything with just a few key strokes on a computer key pad. I went to the search engine and typed in "pornstars who escort, Hayden Winters".

Right away: paydirt.

There it was; Pornstar Escorts of Las Vegas Agency.

"Slim, sexy brunette Hayden Winters is the perfect mix of innocent and devilish. A gorgeous face with pouty lips and bright eyes, Hayden is a definite head-turner wherever she goes. Hayden is new to escorting but her classic 'GirlFriend Experience' will be a hit with our clients because of her mix of beauty, sense of fun and sex appeal."

"Call Hayden to ask about availability."

Oddly enough, this was a bit disconcerting. I mean, its common knowledge that many if not most porn stars also hook on the side. When you get fucked on film for a living, it's not exactly a great leap, right? It's just that, well, I'd sort of come to think of Hayden/Tracy as . . . well . . . my girl.

I normally don't go with hookers. I mean, there's no shortage of quality pussy to be had for free, so why pay a grand or more for what I can get for free? I'm simply not willing to risk everything -- reputation, relationship, health -- but this was different. This was an opportunity to relive my youth. A very special and poignant time of my youth. For this I was willing to pay to be with a very special lady -- we're talking a thousand here but that's for an all-night in-call.

And she was keeping some pretty good company. Here's a sample of the sluts I'm talking about: Eva Angelina. Lena Cova. Stormy Daniels. Brittney Skye. Kayden Kross. Vicky Vette. We're talking some gold plated pussy here.

You guessed it -- I talked myself into the deal. So this is how a happily married, church-going conservative hooked up with and spent a night of sin fucking the living double of his high school girlfriend.

I travel a lot in my work; finding my way to Las Vegas is practically a detour. I could actually make it a business-related trip and work it into my expense account. All my boss asks for is a business-related purpose and everything I charged backstopped with receipts. So I had the where -- all I needed was to line up the when and it would be off to the races.

In the Internet age there's a whole protocol to become involved in; you can talk with your prospective date via email or twitter. By the time you and the lady of your dreams actually get together, a guy can specify special lingerie, schoolgirl outfits, everything right on down to role-playing.

I reached out to Hayden through the website, sent some nice perfunctory messages; told her I was a fan, said she reminded me of a former girlfriend but "I'm not a stalker."

Hayden: That's so nice of you to say. A girl meets all types in this business.

Me: Let me say that you are simply gorgeous! May I ask what would be the age of the oldest man you would ever have sex with?

Hayden: I don't know lol I never asked ;)

Me: Checking out one of your shoots with "_______________" (high-end art-type erotic nudes site) . . . Love it!

Hayden: Yes I like working with them.

Then I got serious. Me: Working in porn, does sex still have the same magic to you? Is it still an intimate thing that you do with someone you love or is it more of a recreational thing now?

Hayden: If I'm with someone I care about it will always be special. Sex without feelings behind it isn't special, it's just sex.

At this point Hayden took the high ground: What about you, Sean? How is it for you? What do you like?

Hayden continued: I know that some guys like to be dominated. Some guys want it nice and slow, some guys want straight up hardcore sex like they see in the movies. Some guys want to abuse and humiliate the girl they're with, like she's his hated mother-in-law and he's taking it out on her with psychological abuse while he fucks her, if you can believe that.

I told Hayden I just wanted to relive that special time in my life, when I was with my high school girlfriend. My first girl -- the girl I lost my virginity with. I said 'with' and not 'to' because she was a virgin also. We popped each other's cherries together, at the same time.

Hayden: Awww, that's so sweet!

Me: Only with a twist.

Hayden: OK, shoot.

Me: I want you to act all sweet and innocent -- on the front end -- then as we get into it I want you to get all slutty and kinky.

Hayden: Oh I get it -- sort of like the Mother-in-Law Grudge Fuck but with a new twist.

Me: No -- not a grudge fuck. I loved her; she was my first girl. I just think I'd enjoy fucking a dirty talking pornstar version of her -- which to me is exactly what Hayden Winters represents.

Hayden: No problem. I can handle it. Any kind of special outfits you have in mind?

Me: Miniskirt. Micro-mini. SHORT. Tied-in-front halter top, long sleeves is nice.

Hayden: Lingerie?

Me: Just plain simple white or tan bra and panties. Nothing special.

Hayden: I get it; Little Miss Pure-As-The-Wind-Driven-Snow, then when you can rip my dainty white underthings off me I turn into a totally wanton, slutty, sexual being?

Me: Something like that.

Hayden: Ha ha! This will be fun! Do you want me to put my hair up in pigtails?

Ooh . . . pigtails! I was actually tempted for a moment.

Me: Nah, that's okay -- she was way out of pigtails when we got together. Besides, I only like pigtails on older women, over forty.

Hayden: Ha ha! This IS going to be fun! You're a funny guy, Sean.

The funny thing was I wasn't joking; there's something especially kinky and perverted about a middle-aged woman with her hair in pigtails. She's sending out a definite message that begins with F-U-C-K and ends with M-E.

Hayden: Who do you want me to be, Sean? What was her name? Do you want me to go by her name?

Me: Her name was Tracy but no, I think that would be too much. That would be too real for me. I think it might actually take the fun out of re-living the fantasy. Lets just go with Hayden.

Hayden: You know, this will probably work out Sean but only because you so totally accept we're dealing with a fantasy here. Because you're not expecting me to be somebody else for your fantasy and not the real person ya know. Rita Hayworth once said, "Men go to bed with Rita Hayworth, but then they wake up with me."

Me: How are you with an all-nighter? Would you be game? I want the FULL 'GirlFriend Experience'

We made a date.

The big night came; I was checked into the hotel, ready and waiting. A knock came at the door. I got off that sofa like a rocket and opened the door.


"Hayden! So good to see you! You look GREAT in person; your photos don't do you justice!"

"Why thank you, Sean! That is so nice of you to say so . . ."

I wasn't lying. Hayden Winters the pornstar had just walked into my hotel room and she was as fresh and young and vivacious and good looking as her images on line, only more so.

She was wearing a simple gray wool businesswoman's suit -- slacks not a skirt - and strappy heels completed her businesswoman's look, which is what she is when it comes right down to it. She was carrying an oversized leather purse over her shoulder, which I assumed had the clothes I'd asked for and who knows what else in it.

We sat down on the sofa, facing one another. There was a bit of distance as if this were a job interview. I handed her a plain white envelope. "Here, let's get this nasty little business out of the way right up front."

"Oh, thank you Sean." She tucked the thick envelope into her purse, then faced me and crossed legs. One arm over the back of the sofa, the other brushing a strand of hair back behind her ear in a gesture that I swear was identical to what my Tracy used to do.

"Tell me about yourself, Sean," Hayden volunteered as an icebreaker.

"Well, I'm married, and I love my wife a lot; I've never done anything like this before. Its just that when I saw your face on the Internet, and the resemblance to my high school girlfriend Tracy; of course, well, just wanted to do something different, is all."

"I understand completely. I hear that a lot, actually. Not the girlfriend bit, but married guys wanting to strike out, experience a little action on the side."

"Well, I love my wife a lot." For some reason I repeated myself.

"I understand, Sean," Hayden placed her hand on mine. "If it makes you feel uncomfortable, don't talk about her."

"No, no, its not anything like that. I'm very excited about your being here." And I was. Here was a beautiful nineteen-year-old who carried herself with the sophistication of a fully-grown woman -- I guess a couple years in porn with do that to a woman -- and just the knowledge that over the next couple hours I was going to rub my cock over each and every square inch of her body was having an unreal effect on my psyche. An almost out-of-body experience.

"I'm a big fan of your work," I volunteered. "I hope that doesn't bother you."

"Why, thank you! No it doesn't bother me at all! I'm retired, of course, but no regrets, none, over my porn years."

"That's good."

"Oh, I loved every minute of it, believe me! Not every girl in porn enjoys what she's doing but I did! It was thrilling! To enjoy doing porn you've got to be a total exhibitionist. That, and a nympho of course, and I'm both, obviously. Um, Sean, it won't turn you off if I'm frank?"

"No, not at all. You can think of me as your Father-Confessor."

"Oh, that's sweet."

"I mean, I am old enough to be your father, after all."

"Ha-ha! Well, I wasn't going to throw that in there, but you said it!" Again with her hand on mine. This beautiful young creature was having a visible effect on my libido.

Hayden went on, "There's something about being nude in front of a room full of fully-dressed people that really turns me on. I mean, having sex - whether with a man or another woman - in front of a director and a camera crew close enough to make out the color of my eyes."

"Woah." I was getting turned on just listening to her describe the situation.

"But it was just wasn't what I wanted to do forever, and it was time to move on."

It's incredible; Hayden carries herself in such a way she can be anywhere between eighteen to thirty-eight. Right now I was looking at a young twenty-something who for all the world resembled a sophisticated businesswoman. Kind of like an older version of my Tracy; a few years out of college, and we were discussing her career which of course involved sucking cock . . . a LOT of cock, fucking total strangers on camera for all the world to enjoy . . . other worldly.

She got up off the sofa, put her hands to the front of her blouse. "Say, I've got something to show you, Sean."

I just smiled. Given the circumstances, those words could only mean one thing. Hayden smiled right back, looking me straight in the eye as she undid her buttons, untucked her silk blouse and pulled it wide open.

Simple white bra, sort of half-cups almost like a shelf-bra. Nice. Very nice.

Her jacket came off, then her slacks, and there she was in a nice silky white blouse, open in front, simple white bra and panties. With her strappy heels she looked like a high-class escort. Which was what she was, of course.

"I wanted to show you the white bra and panties," she smiled.

"Thank you," I said. "I approve."

"Say, may I use the restroom and freshen up a bit?"

"Sure. Yes, of course."


I watched her round asscheeks going up and down in her slacks as she moved across the room; like two piglets in a sack.

(To be continued -- V.H.)

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