Tailored – the story of Tommy and Hanna

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.