Tailored – the story of Tommy and Hanna by Doc Olivia

A literotic sexstories: Tailored – the story of Tommy and Hanna by Doc Olivia ,

Tommy is a guy who was treated poorly by his ex.

Hanna is a girl whose parents wanted to force her into a bad marriage. Through the intervention of Tommy’s ex girlfriend they are brought together

Tailored – the story of Tommy and Hanna by Dr. Olivia Udell

Tommy starts the story

About 3 months after my surprise divorce from Janice, I received a letter, yeah, an actual letter from the first girl who broke my heart, ripped it out of my chest, stomped on it and laughed, Jessica Goodall.

Jessica was my College girlfriend. We met Freshman year and I thought we were inseparable throughout. But, as it turned out, I was inseparable, she was fucking every other guy she met. He girlfriends covered for her until Senior year when one of them slipped up. I went over to her dorm and her friend Laura said, oh she’s upstairs with Gary. Gary? I said. “Oh shit, I wasn’t supposed to say” said Laura as I bounded up the stairs to Jessica’s room. She hadn’t even locked to door and it wasn’t only Gary. Enough said. I just slammed the door and walked out.

Jessica called later and tried to explain -”Its just sex” was her excuse. But that was that, and we were done. It was only afterwards that people told me the rest. It wasn’t pretty. The deception really hurt.

So, I sort of stared at the envelope. Good quality paper. You don’t see that much these days. And the return address Miss Jessica Goodall Graysen. “Graysen” who the hell was Greyson and since when did Jessica – the uber feminist – use Miss?

Eventually I opened the envelope and took out the actual letter. It was handwritten and scented. Yeah scented. And scented with the perfume I once loved and now loathed. The scent of Jessica.

But for some reason. I found my heart pounding and well you know

I opened the letter

Dear Tommy

I know that I might be the last person you want to hear from, especially now after Janice’s betrayal. I realize now, how horrible that is and how unfair and how disrespectful, and what a bitch I was to you. Which is why I am writing. I want to make it up to you. I couldn’t before, I didn’t even know that I should. I mean I thought I was the wronged one. You dumped me. Just because I was fucking some random dude. But now I know better. A lot better. Now that I have been tailored, I really understand what I did was wrong, and really bad.

But, the good thing is my, ummm my husband told me that he would do this for me, well, you really. He said he wants to give you a tailored girl. I have to pay for it, but I don’t mind because Terence, that’s my ummm husband, well, you’ll see.

Please call me 1 987 654 3210 Terence, ummm Mr. Greyson wants to explain it all to you and well, so do I. I know that a tailored girl will be everything you wanted me to be, which I wasn’t, but should have been.

Please call soon. I am so sorry about, well being a shit to you and about Janice. I knew she was no good. I should have told you. Sorry.

Love

Jessica

I sat there staring at the letter for a long time. Could I forgive her? Could I ever speak to her again? What about this Greyson dude? And what the heck is a tailored girl? I must have read the letter 16 times before I found myself suddenly picking up my phone and dialing. I hadn’t even looked at the time, but it was 12:42 am, luckily Jessica was awake or the timing of my call would have been really bad.

Jessica answered on the first ring. Tommy? Is that really you? You got my letter? Can you ever forgive me? Will you come and see Mr. Greyson, Terence and me?

I broke into the stream of questions saying, I thought Terence was Mr. Greyson.

And Jessica said, He is and well so is his father, but his father is really Dr. Greyson and I guess Terence is too, but he doesn’t like to use Dr.

OK. but what is this all about? I asked

Its about making amends, I mean making up for being such a bitch to you, and my becoming a better girl. Said Jessica

I thought “better girl” in the 4 years I knew her, Jessica had never referred to herself as a “girl”. She was too much of a feminist for that. I mean she was rabid about it.

“Please come” she said, please.

It turned out that She and the Greysons were about an hour and a half away from me so I said sure, I would come out that weekend and we made plans for me to come on Saturday for lunch. So I arranged to arrive at 12:30 on Saturday.

LUNCH and BEYOND

The drive to the Greysons was uneventful, arriving at their home? mansion? estate? Was a bit different. Their drive was marked off by a gate which opened as I approached and closed after me. It was then another 3 minute drive through parks and gardens until I reached the house. It wasn’t huge, but no one would ever say it was modest. Unlike most similar houses I had seen, including the one owned by my boss, OK. My boss’ boss’ boss, the owner of Rebourne Realty Holdings, Gerald Gleason Dillwell, it was actually not ugly and pretentious ,just large and imposing. It was brick and stone in the Georgian style and had 3 stories and 4 chimneys as well as smaller additions on either side and had a circular drive. I pulled to the side and got out of my little, none too recent, Honda Accord and ascended the stairs to the double front doors.

As I approached the doors opened and Jessica came out accompanied by a tall, slim man. Jessica was completely naked except for a gold choker collar around her neck, a thin gold chain around her waist and when I got closer, I could see a gold clit clip. The man was dressed in tan chinos and a white golf shirt. When I saw them I stood there in complete shock and well awe.

Jessica was even more beautiful than I had remembered. There was not a single ounce of fat on her taut body and no sag to her B cup breasts. There was also not a single hair visible below her neck. This was a change from her fierce hirsute in college, when she denounced men’s requirements for women to shave their pits, legs and pubes.

Jessica said “Hi Tommy” and ran to give me a big hug, which was rather unexpected. Being hugged by my naked ex girlfriend had the expected result and I kept thinking “down boy, down boy.” The problem was that Jessica was even more beautiful than I remembered. She was stunning. I didn’t remember stunning.

After she let go, I started up the steps with Jessica and I heard the man say “Welcome Mr. Greene” and then turn to Jessica and say, “present” at which point Jessica placed her hands behind her head, stuck out her chest and spread her legs.

The man said, “Mr. Greene” and I said, please call me “Tommy” so the man continued

“Tommy, as you can see, Jessica has changed, she has reformed, since you last saw her. My name is Terrence Grayson, welcome to our home.” and he gestured me in.

“Ummmmm, is Jessica, ummm always naked?” I asked

“Not always, but often, and I thought it was necessary today, so that you could see how well our tailoring program works. I wanted a willing, slave, fuck toy, and Jessica showed real promise when I first met her at my practice.”

“Your practice?” I asked

“Yes, my father and I are practicing Psychologists here in XXXtown and in our Psychology practice, we have developed a specialty in providing perfect companions to *********** gentlemen by tailoring girls to their specific requirements, desires, what have you.

What?

Simply put when we come across a female patient or prospective female patient who is amenable to our special treatment, not that they are told that they are going to be tailored to the specifications of our gentlemen clients we identify one of our gentlemen clients to whom the female patient can be tailored.

It seems rather unorthodox but how did you *********** me for the privilege of meeting a tailored girl?

Oh that, that is due to Jessica, as part of her tailoring program, the truth of how poorly she treated you came out and she realized that she needed to make up for it. It was actually her guilt over how poorly she treated you which was behind the problems she initially saw us for. She was so wracked with guilt, maybe assisted along a bit by her treatment, that she insisted on making it up to you. Together we decided that the best way for her to make amends was to find the perfect girl for you, when the occasion arose. It has now arisen.

You mean you have found the perfect girl for me?

Yes, and no. Said Terence We have identified a prime candidate. However, while we have a fair idea about what you require, we do not have a complete picture. We do not know if you are willing to accept her and we have only begun her tailoring. We are likely 2 to 3 months away from delivery.

Ummmm I started to say

Oh yes, there is no cost. Jessica has paid for the girl’s treatment and the necessary testing and surveys for you. Said Terrence

What is this testing and surveys? I asked

Basically it is a series of questionnaires you will complete on line, it is a secure private web so no worry there and two or three in person interviews. We can start today after lunch.

Jessica interrupted with Please say yes Tommy

this was followed by Terence correcting her, Jessica quiet. Which was followed by a yes sir.

I can’t tell you why but I said yes.

– – – – – – – – – –

2 months to later:

I returned to Jessica and Terrence’s home 2 months after my first visit. Jessica had sent a second letter to inform me that they wanted me to meet a girl, a fully tailored girl. So I went

I arrived as instructed at 3:00 pm. and was greeted once again by a completely naked Jessica who today was wearing a heavy gold choker collar, two nipple clips, and nothing else.

She greeted me and led me into the house where I was met by Terrence. The meeting was brief. He welcomed me and told me that he had a girl he wanted me to meet in order to determine if she was acceptable and what additional tweaking she might need.

With that he led me upstairs to what I assumed was one of the house’s bedrooms. He left me there and told me to strip down and that when I was ready to enter the room. He did not tell me the girl’s name or anything else.

It seemed odd but I figured, “ What the hell?” and took off my clothes. Then, I took a deep breath and opened the door.

Standing in the middle of the room, next to a hard backed wooden chair, stark naked was someone I knew very well, and didn’t know at all. I just stood there in shock

She said Hi

and I said, You, you, you, are you Hanna Raider? My god you look just like her. Do you know her?

And she said. Yes, I’m Hanna Raider but that’s a stage name, my real name is Annabelle Grace Dillwell.

Stunned I said Dillwell?

Yes, she replied with a smile

But, but, but, I ummm I work for the Dillwells, well one of their companies.

Yes, I know. Please come sit and I will tell you everything you want to know, anything, no secrets.

So I walked in the room and sat on the chair as directed by Annabelle/Hanna. As soon as I was settled Annabelle/Hanna sat on my lap facing me. Sitting on my lap we were more or less face to face. I was face to face with my dream girl, my favorite porn star, the perfect girl, blond straight hair, bluest blue eyes, slender with small firm breasts which rode high on her chest and capped with pretty pink nipples, little round rump, firm flat stomach, enticing thigh gap, pure pink puffy wet pussy, and slender athletic legs. She also had the voice of a very sexy angel and while performing the cutest gasps, whimpers, moans and screams of pleasure. She always seemed to love whatever she was doing. I was soon to discover that she really did, but the story behind that joy was complicated.

HER STORY – SEX STUFF STARTS HERE –

Anna begins

He recognized me!

He recognized me and wasn’t threatened or repulsed, or

Is that the look of love? Admiration.

They said he would be the guy for me, but I never thought.

I mean, I’m a slut, no a whore, a professional cum bucket, splooge drinker, piss whore.

They said he would like me

They said I would like him.

More than like, adore, worship, live for.

I think I can do that. I really want to.

Those were all the thoughts which went through my head as Tommy walked into the room, and all I could say was” “ Yes, I’m Hanna Raider but that’s a stage name, my real name is Annabelle Grace Dillwell”

What a dork I am, I don’t deserve him, am I good enough for him, will I ever be?

Just like they told me, I asked Tommy to sit on the upright wooden chair in the middle of the room and then sat on his lap facing him. His cock was rigid. It. looked really nice, not big, I had seen lots of big, lol but nice maybe a little smaller than average even – but so nice, so somehow as I sat down I slipped his cock into me. It felt so nice. I sighed deeply as I sat and somehow it just felt, you know, right. Like this is where I belong. Yeah its odd, I know.

And Tommy felt the same way, Even though neither of us said a word about it, just held each other for a while. Held on tight until I felt him shoot inside me. It was ,it was, great, I mean like totally satisfying. And I said thank you and we laughed, because who ever says thank you when a guy cums inside them, like just cums, but wow, I was so happy when he did. How did they know that would happen. They told me it would and it did.

And then he asked me to tell him about myself.

Myself?

Um OK.

Well, as I said I’m Annabelle Grace Dillwell, but other than that, I really have no contact with my parents or the rest of the family. They disowned me.

No no not because of the porn films. I don’t even know if they have ever seen them.

Why?

Why? Because I wouldn’t marry the scum bag rapist they wanted me to marry.

Who is he. You probably know him, Jason Furst-Simmons

Uh huh that Jason Furst-Simmons, Yeah the one who just got off on charges of being a serial rapist. Yeah the one who preyed on preteen girls. Yeah, me 2. I think I was his first. If not his first sort of the beginning of his career.

Why did they want me to marry him?

Because his Dad and my Dad are golfing buddies and are business partners in like a dozen different businesses.

Yeah he is older than me, but only like X years and they didn’t think that was a problem. So I was an X year old girl given to this scummy X year old guy by my parents. Yeah, he took me down the shore with his parents the summer before his senior year at Wharton, where else? Except his parents were never there. But I was. So like the first night we were there by ourselves he just came into my room while I was sleeping, pulled my nightshirt off of me, slapped me and said, suck my cock bitch.

I started crying and tried to say no but he kept hitting me and telling me to suck his cock and if I didn’t he would just keep hitting me until I did.

Yeah, I was even smaller than I am now and now I’m what 5’1” on a tall day and maybe 90 pounds on a fat day? And he is 6’5” and back then he had muscles, he was a body builder and star at the boathouse, doing that rowing thing.

So like, even though I never did it before, I was sucking his dick and getting face fucked hard. It seemed to go on forever and then he squirted in my mouth and held my head to his groin so I was forced to swallow it.

Then he pulled out and hit me again really hard and said, from now on, you are going to suck my cock whenever I want, No, every time you see me, you are going to ask to suck my cock, BEG!!!! and then he hit me again so hard I was thrown a few feet to the side and then he walked out of my room.

I just cried.

Eventually I fell asleep but I was woken up the next morning by Jason who pulled me out of bed, slapped me hard and said Cunt, I have to pee and then he pissed on my face and laughed. After that he had me suck his cock and he “gave me breakfast”. He was big on giving me breakfast – his cum – every morning I was there.

Yeah, it didn’t stop with blowjobs. By the end of the first week he was sticking his filthy cock in me, my pussy, my ass, my mouth pretty much whenever the mood struck.

The second week he invited some friends from College over and he made me suck and fuck them too. So, there I was getting gang banged at X by a group of college guys pretty much every day for the next two weeks.

Of course, no one believed me. My parents especially did not believe me. They told me to stop lying and forced me to keep seeing Jason – yeah for years – it wasn’t till I finished college. A prestige college graduate pornstar and total disappointment to my family, that’s me.

Well, yeah, they wanted me to marry Jason. I just couldn’t – not after years of rape and abuse. No way. So after graduation from P+++++ I ran away.

Yeah, where else to California

So, I got there and well, money was tight, and I saw this ad for like modeling and it turned out to be porn but I went to the interview anyway and guess what?

Yeah, I loved it. That first day, that first interview the guy just talked me into stripping and then he told me to suck his cock and I have to admit he had a nice cock and ummmm I like sucking cocks so I did and I know I did a good job because he came like in a couple of minutes, but he was still hard so like in 10 seconds I was flat on my back on this couch and this guy I just met like 10 minutes ago was ramming his cock into me and I was cumming like crazy, I mean I never came when Jason or his friends or whatever fucked me and they had fucked me a lot, I mean A LOT, but here was this total stranger making me cum over and over and over again and he kept repositioning me and kept fucking me, it was like he would never cum but I was cumming like every two minutes or even less and then he let out this big bellow and pushed into me so hard I thought I might pass out and spewed his stuff into me, spurt after spurt after spurt. When he puled out he told me to push out the cum and I guess I did because I have seen the shoot, you probably have too –

You did, That’s great. Did you like it?

You did! Really! You aren’t just saying that?

Wow, thanks. And yeah I was totally fucked out, completely exhausted, I sort of collapsed back on the couch and I know it was a while before I woke up, but the guy – his name is Mike Deecham, by the way, he’s like been in me dozens of times since. Yeah on film and well just cause he asked, he was like saying how great I was and how he was positive I would get lots of work and hey, I did.

Like 3 days later I was showing up at the fancy house and like 5 minutes later I was getting fucked by this huge black dude on the deck next to the pool. Yeah, you’ve seen that one too. Cool.

Anyway, you know how he cums in me twice well after that he just picked me up and threw me in the pool. Wow, talk about a wake up and yeah its a good thing I can swim. I am actually a really good swimmer, I have my Life Guard and Water Safety Instructor certification from the Red Cross, yeah its still valid cause while I was in Cali, I life guarded a bit in between shoots.

How many? Shoots you mean ummm at least 100, probably closer to 200 so far. I don’t know if all of them have been released. I know some of them were supposed to be just for collectors, particularly the ones with dogs and stuff.

Yeah I fuck dogs. I love dogs and well letting them in me is just sort of natural – you know, they want to fuck and its just mean not to let them, right?

Yeah knotting can be a real pain cause then I am pretty much stuck to the dog until it goes down, but wow you should see the cum pour out after I get released it amazing and like dog cum is way hotter than boy cum, temperature that is. I sort of love boy cum. OK. I really love cum. And I, well this is sort of embarrassing but like getting cummed in is sort of my favorite thing in the world. Yeah it is.

Uh huh, that’s what makes porn so great. I mean where else can you like meet a guy and like less than a minute later be sucking his cock and drinking his cum or have him pounding your cunt or ass or double teaming you or whatever. I mean, how could I not love that?

Well yeah, here you sort of just came in me like two seconds after we met but that’s different.

Why? Ummm I guess because I love you.

Yeah like already. Its weird isn’t it. I mean they said they were going to introduce me to my perfect guy but like who really believes that? I mean, oh sorry, I didn’t mean you aren’t my perfect guy because like you totally are.

No I love your body and your cock is perfect. I mean it just feels so right in me right now, like better than any cock before, and like I don’t know you are supposed to be in me.

Does that make sense?

You feel the same way? Wow, that is so great.

Yeah, like I would like to keep making porn, but if you don; t want me to I’m fine with that too.

I can? Its OK.? Really? OMG, I really really really do love you. You are so super perfect. I mean, OMG I don’t know how to say it.

No. I wanna be totally loyal just to you, so like sure I’ll fuck for the porn stuff, and you know when I’m told cause that’s all part of the business.

Yeah, sometimes they, the producers and stuff, they rent me out to people or maybe just lend me, you know sort of as a favor. But, like I don’t mind cause its just fucking and sex and stuff and I do get to cum and I get lots of cum to drink and cummed in and all that, so its fine.

Ummm no better than fine, I don’t know, it just makes me feel so good.

Yeah, it might be a little exploitative, but like all the girls do it.. Speaking of which I know a couple girls I think you’d really like cumming in. I mean its only fair that if I am off getting fucked in a movie or something that you get a nice cunt to cum in while I’m away.

No, really, I want you to fuck them. I want, no I need you to be happy. I need to know that well that you never lack anything or anyone

Of course I know your type.

No, really I do. You like girls like me, silly.

Yeah, I don’t know, if I am lucky maybe a couple more years. They sort of seem to drop girls you know after a while, but I have a really good following so far, yeah so that helps. So as long as guys and you know girls, lots of girls watch a lot of porn, and like lots of my really biggest fans are girls.

Yeah, well anyway, as long as I have lots and lots of fans they are going to keep putting me in scenes, you know if I want and as long as its OK. with you.

Really, anything I want? Really.

OMG you are so super perfect

We are going to be so great together

OMG we already are, I’m cumming again.

HIS STORY RESUMES

OMG. She really is perfect. Who knew, the perfect girl for me was a little, spoiled, blue blood, debutante gone so bad. Or so good. How am I ever going to thank Jessica?

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