Legal: I do not own DeGrassi, would not admit to even if I was.

Important things to know before you read:

*Adam never died but broke up with Becky in their senior year when she and her family moved back to Florida.

*When Dallas was kicked off the Ice Hounds he returned to Guelph.

*Drew and Bianca parted amicably; Drew dated several girls in his senior year but not Clare or Zoe since she doesn't exist in my world (it's a happy world). Drew and Clare did become friends.

*Clare and Eli broke up after he cheated; she never got pregnant but did date a few other guys in her senior year and while attending Columbia.

*Clare is now 25 and has been out of Columbia for three years, she has a fledgling career as a journalist and freelance writer.

The rest will be explained in the shot which is all in Clare's pov.

Ch. 1 A Schoolboys Dream

I arrive at The Tower Hotel and valet my car, most of my clients meet me here because they can afford to. When I graduated from Columbia and was offered a job at The Toronto Sun I took it. However even a degree from Columbia didn't get me much of a head start. I spent a year doing little more than I had done at my Interpreter internship. Slowly my editor gave me more and finally a little over a year ago finally I was a reporter with a regular byline. Still I was at the bottom of the ladder, given little space for my articles and little respect at the paper. In fact my male editor seemed to delight in giving me the stories of opening shows, rescued animals and other fluff pieces. When I first got hired my job at the paper did not come close to covering my rent and other monthly expenses so I soon found myself in need of another job. I wanted to keep my job at the paper though so I needed something that wouldn't interfere. Even now my paycheck wouldn't be enough for me to live off of, which is why a lot of reporters get syndicated in more than one paper.

It was rather by chance that I fell into this line of work as an escort, a nice way of saying I was a very expensive prostitute. Not that anyone has any idea what I do, nor do I plan to tell them. After losing my job at department store for having no patience with an idiot customer, it wasn't the first job I lost either, I went looking for a new job. I met Danielle while turning an application in at a restaurant; she took one look at me and said she had a better job for me and one that would pay five times as much as being the hostess at a restaurant. I went with her to find out what it was; I was both horrified and intrigued when I did find out. When she told me I could make as much as five or even ten grand a night, plus tips, I gave in. It's not as though she just slapped a skimpy dress on me and sent me to the streets there was six months of training. How to read men, and women too, how to give them their fantasies without them needing to say anything, how to dress, present myself and adapt to all situations, how to defend myself if by chance a "date" goes bad. It was proper concubine training actually and I learned quickly, Danielle always said I was one of her best students.

I've been an escort for almost two years now, including the training. I have a few regulars now, all the girls do. One of my regulars sees me as often as once a week, a business man in his fifties that's never married, he likes to take me to events and dinners, I'm his arm candy and sex is not involved. Actually it rarely is, being an escort is less about sex and more about fulfilling a fantasy for the night. Of course the fantasies do include sexual aspects often but that doesn't always mean sexual intercourse or even oral most of the time. Last month I started a syndicated sex column, it's like an advice column using the knowledge I've gained as an escort. I write the column under the penname of Miss M. I don't use my real name as an escort either of course; I go by the name Madam D, a throwback to my days as Madam DeGrassi. I only work in Niagara Falls and sometimes London, Ontario not England, so that I lessen the risk of seeing someone I know on duty. And it was working until tonight because when I knock on the door of the hotel room Owen Milligan answers!

"Clare!" He gasps astonished and pleasantly, carnally fascinated at the same time.

Our clients often use a code name for anonymity, of course many of them are rather well known anyway but we have strict confidentiality agreements. All I knew for tonight before knocking on the door was that my "date" went by the initials OM but I never thought it would be Owen not that it's going to stop me. I give him a salacious smile, dragging my finger down the buttons on his dress shirt. I must admit I thought Owen was hot in high school, hot but a massive jerk. By the time he wasn't a jerk I was all in the Eli/Jake drama and even when I wasn't it's not as though Owen and I traveled in the same circles. Truthfully I'd all but forgot about him after he graduated but now he's here and at my mercy, and shelling out $700 an hour for my company.

"Hello Owen," I say in a sultry voice putting my hand on his chest and pushing him into the room. "You said you wanted a dominatrix, so," I say looking him over and around the room to size him up. Using the added advantage that I know what he was like in high school, "I'm guessing you have a position of power and you're tired of making decisions and having to think," I comment taking off my long black coat to reveal the six inch leather stilettos, fishnets, vinyl skirt and leather bustier that I wear.

"Holy fuck you look hot! You should have dressed like that in high school," Owen comments and I reach into my bag pulling out a doubled leather strap.

"Did I give you permission to speak?" I question in a harsh tone slapping the strap into my palm so that it makes a cracking sound. Owen specifically requested a dominatrix so that's what I am tonight, Danielle trained me well.

"No Madam D," Owen shakes his head.

"You will call me Mistress and not speak unless I give you permission, is that understood?"

"Yes Mistress," Owen replies and I see by the growing bulge in his pants that he's hard which makes me grin.

"Good boy," I reply sitting at the edge of the bed. "Now take off that shirt and kneel before me," I command. He obeys taking his shirt off; I must admit that I enjoy the sight of his bare chest. "Kneel down and lick," I command holding up my shoe. Again Owen obeys and takes my heel licking the toe. "Stand again, strip entirely and tell me what you do for a living," I tell him.

"I work as a pilot for a private company, taking high profile VIP clients, and sometimes questionable merchandise, all over the world. It's a small company and I'm one of the few pilots and a manager," he informs me while stripping naked, mmm he is a sexy boy!

"Impressive for such a young age," I grin looking at his growing erection; he's quite a big boy too. "Now have you ever performed cunnilingus?" I ask and Owen just pinches his eyebrows together. "Have you ever eaten pussy?" I rephrase the question.

"No Mistress," he responds.

"Then I would say it's time you learn," I reply crawling back on the bed and spreading my legs so that Owen sees I'm not wearing any panties.

His mouth drops open and then he smiles licking his lips, he crawls on the bed and I begin instructing him. He's very obedient and does exactly as I tell him bringing me to a lovely orgasm. While I recover I order him to bring me water and then kiss him as a reward, which makes him smile and very hard again. After a few sips of water I instruct Owen to lie on the bed, when he is I tie him to the bed posts. I very much like look of him naked and spread eagle tied to the bed, I wish I could take a picture but of course that is not allowed, for us or the clients. I put a condom on Owen, also a rule safe sex is insisted upon and everyone, clients and us girls, are routinely tested for all manner of things and must prove to be clean before a date is arranged.

When the condom is on I mount him, Owen moans and I smile riding him the way I was trained. Riding him a long time, I could have brought him to a climax several times but what would be the fun of an early orgasm. I know how to bring him to the brink and make him hold it until finally I decide he can take no more and allow him to release. Owen's entire body breaks into spasm; he moans loudly calling out my name, my real one since he knows what it is, as he orgasms wildly and with full abandon as he's lost all control. I slow down as his orgasm dissipates, dismounting from him while he lays there, still tied to the bed, and panting hard. I remove his condom, lightly stroke his cock sending him into salacious tremors once more. I finally untie him, and he sort of folds but never takes his eyes from me.

"Fuck me that was amazing," Owen says breathlessly.

"I just did Honey, and it'll be $1050 for an hour and a half," I reply with a grin as I begin to gather the bindings and leather straps.

"Well worth it but don't go yet, I'll pay extra, I want more," Owen begs finding the strength to get off the bed. "Please mistress let me eat you out again, I still have lessons to learn," he requests crawling to me on his knees.

"You're an eager student," I reply then bite my lip with a lascivious grin, putting the toe of my spiked heel on his shoulder and lightly resting the heel on his chest. "Just remember if you disobey I will punish you," I tell him.

"Yes Mistress I am at your mercy," Owen responds and I grin.

Owen keeps me for the entire night, he takes me to orgasm twice more and I make him climax three more times before the sun rises. After my rather hefty fee, for keeping me for the night, he tips me $1000 on top of it.

"That was beyond incredible, if I knew you could do that in high school…"

"I couldn't in high school," I remind him.

"Right, doesn't matter it was amazing, more than amazing. I'm going to need several days, possibly a week, to recover but then I want to see you again, must see you again. Next time I think I might disobey and be punished, I think I might like being punished by you," Owen tells me with baited breath.

"Just call the service, I only work weekends anyway I do have a day job," I comment.

"Right I heard you were a reporter, Lois Lane by day and super sex goddess by night," he remarks.

"Something like that, just remember you need the cash, it's cash only," I remind him before grabbing the back of his neck, pulling him to me and abducting his lips for a hard and tantalizing kiss, lightly biting his lip as I pull out of the kiss.

"Cash right I need to pay you," Owen whispers when our lips part.

"You already did, see you around Owen," I smile pushing him to sit on the chair I just took my coat from.

With that I leave and make the two hour drive back to the agency, leaving Danielle's cut for her before driving home. I keep a fairly modest apartment so no one asks me where all the money is coming from. Not that I'm really in touch with anyone any longer, I see my parents since they still live in town but not very often, I go to dinner at the house maybe once every couple of months. I see Jake when he comes to town, I see a few other people around town sometimes but ones that I was never friends with. I keep in touch with Adam but he lives in San Francisco and since his parents moved to Seattle Drew goes out there to visit them. Drew still lives here but travels a lot; Adam told me Drew works as a consultant. I've seen him in passing a few times and we've chatted a couple of times but it's not as though we meet for lunch or anything, actually I haven't seen Drew around for a few months.

My week goes by like any other, my job at the paper and my column keeping me mildly busy. When I return to the agency Friday afternoon Danielle is in the front room, she's never in the front room she's always in her office or the training rooms.

"There you are I've had multiple requests for you. You're booked solid for a month, I got so many I raised your rate. OM was extremely happy and made a lot of recommendations, you have two dates tonight, your first starts at six here's the info. No more than four hours your second date is at ten-thirty. I've already packed your bag you just need to change, a nice dress they didn't request a costume, your client's code name is Brown," Danielle informs me.

"Owen recommended me, this should be interesting. I wonder who my client is and what Owen told them?" I ponder silently as I go up to my room to change into a dress.

I choose a black one; it goes to the floor but has a slit that goes up to my hip bone. I can't wear a bra with it because it has spaghetti straps and the neckline drops down well past my cleavage. I wear a long coat with it to cover the dress; I get driven by one of our cars because both dates are in town and at the same hotel. I don't normally work in town but both clients paid an extra premium to see me in town, under assumed names at a fancy hotel. So while I'm being driven I look at the info for my dates. The first is fairly vague just says that they want to be pampered. This can honestly mean anything, I had a man last month who requested to be pampered and it meant he wanted to be diapered like a baby. Normally though it means they just want to be spoiled and taken care of. The second one is also fairly vague it simply says I will be escorting him on a date. This also can mean anything, we could be going to a fancy restaurant or a charity gala, even that we stay in and live their fantasy.

The car parks and I walk in with my bag, I already know the room number, because it's in the information they gave Danielle, the room is on the tenth floor. When I knock on the door and it opens I'm shocked to see Bianca standing there, all though since Owen recommended me I suppose I shouldn't be. I don't let it show that I'm shocked, simply grin and bite the corner of my lip. Bianca looks me over and smiles with a lascivious excitement. She licks her lips and stands away from the door so I can come in. Bianca most likely came straight from work as she's dressed in black heels, a black pencil skirt and a white blouse; I also see a black blazer on a chair. I knew from one of my quick chats with Drew that Bianca had become an actuary, and a rather successful one. They hadn't been engaged since high school and I don't think friends was even truly accurate but they would run into each other in town and were still friendly.

"Heard from Owen that you were amazing, had to see for myself," Bianca tells me as she locks the door. Her voice purring with licentious elation and I grin. "Costing me a bundle too thank goodness for my bonus, you better be worth it," Bianca says but she's grinning, practically giggling with anticipation and doesn't sound angry or worried at all.

"Well Owen seemed to think so and I have been well trained in the ways of pleasure for both men and women. Now then you said you want to be pampered so I believe you are a workaholic, your job keeps you busy and under pressure leaving you little time for relationships or even simple pleasures," I remark taking off my coat and Bianca smiles looking over my dress.

"You're good," she grins licking her lips again.

"As I said I've been well trained, I know how to read people and indulge their fantasies so tonight Bianca you are Princess and I live to indulge you."

"You are very good," Bianca smiles as I saunter over to her.

I take her to the end of the bed and sit her down, sitting on the floor at her feet my knees bent and legs curled behind me. I take her shoes off setting them carefully next to me. Picking up her right foot and setting it on my leg as I begin rubbing her foot. She moans a little and leans back on the bed. After rubbing her feet, I stand her up to get her dress off and she takes her bra and panties off, she seems almost nervous now but also very excited. I look over her nude form then put my fingers under her chin to place a soft kiss on her lips, soft but passionate and Bianca melts into it. Lying her on her stomach on the bed I take off my heels, get massage oil from my bag and sit next to her, starting at her legs I spend the next hour giving her a full body massage and when she's fully relaxed and moaning in pleasure I turn her over. I take her lips for a kiss again while I gently rub her breasts eliciting a moan from Bianca into the kiss. I rub and kiss my way along her body; Bianca continues making a chorus of moans, like a rapturous symphony.

I stop at her clit, placing a soft kiss on her pleasure button and she quivers a little. I touch my tongue down and she trembles more, flicking her clit with my tongue sending waves of pleasure through Bianca and eliciting wonderful moans and whimpers from her. Spreading her legs I get between them licking her velvety pussy lips and they open to me. I suck her pussy lips and Bianca purrs arching her back. Gently my tongue probes into her and she quivers, moaning my name as her body tenses and relaxes. Using my skills and her already rapturous state it doesn't take long to bring her to orgasm. Bianca screams my name, her body trembling uncontrollably and she grips the pillow behind her as her back arches off the bed and her climax continues for over a minute. I slowly withdraw my tongue and put her legs back together, kissing my way back up her body as she recovers her breath. When I get to her lips I pause for a kiss before getting up to get Bianca some water. Sitting back on the bed I prop up some pillows and lean against the headboard, pulling Bianca to lean against me, putting my arm around her to hand her the water.

"That was incredible, Owen was right. I wish for more," Bianca says after drinking down the water.

"I would grant your wish but I have another date in half an hour," I tell her taking the empty glass and setting it on the night stand. I scratch her head which makes her purr again and then rub her shoulders until it's time for me to go. "I really must be going, call me again should you need to be pampered or want a little more," I say giving her a quick kiss before getting off the bed to get my shoes on.

"Do you do more? For girls I mean?" Bianca inquires rolling on her side and propping herself on one elbow.

"Of course, I can fulfill nearly any fantasy for anyone, guy or girl. If you can afford me again and so wish it I can bring strap-ons of nearly any size. I can penetrate or you can, or I can wear costumes, use other toys. You name it and I can probably fulfill it," I inform Bianca.

"Mmm it all sounds so wonderful, here your fee plus a tip. Don't worry I'll see you again, I'll just have to start charging more," Bianca grins handing me my money after I've got my coat and shoes on.

"I look forward to it," I smile kissing her again before I leave the room.

My second date is at this hotel only according to the card I'm meeting him in the ballroom. I assume it's a him anyway as the information I have says he gave his name as Mark. There are actually three ballrooms at this hotel, the first two are hosting events and the third is closed off for a private party. This is where I am to go so I open the door and gasp. Suddenly I'm back in Vegas Night at DeGrassi, at least there are several decorations from that night or replicated, even the same music plays but no one else seems to be in the room.

"Fitz?" I call realizing who Mark is.

"Part of me thought you might run as soon as you saw the room," he says stepping out from behind a prop wearing nearly exactly what he was that night.

"Your fantasy is to relive a terrible dance?"

"I thought we might do it right this time, here it's not quite what you wore that night but it's pretty close," he says handing me a white dress with black polka dots, it has spaghetti straps and knee length flowy skirt.

"Boxing must pay well," I smile taking the dress. Fitz is a professional boxer, a fact that I know because I've seen him in the sports section of our paper and on TV. He's actually the current featherweight champion, he does fighting in the states as well as Canada.

"Yeah well I just signed an endorsement deal; anyway I negotiated a great contract for myself. You think this is all silly don't you?"

"No I think this is very sweet, I've always regretted the way that night turned out. I'll be right back," I say walking to the ladies washroom to get dressed. He didn't bring me other shoes so I wear the ones I have. Leaving my things in the washroom I go back out to the ballroom where Fitz is waiting.

"You look great, may I have this dance?" Fitz requests holding his hand out to me.

"Of course Fitz," I smile taking his hand as we start walking back to the dance floor.

"Call me Mark," he comments turning to me on the dance floor.

"Okay Mark," I smile. We dance through a few songs, all slow ones, and then we stop when a fast song comes on.

"I had planned on taking you to The Dot that night after the dance but this will have to do," Fitz says taking me behind the giant roulette wheel and I see a café table with two chairs.

"You really thought of everything," I grin kissing his cheek.

"Yeah well that night didn't exactly happen as planned, I also have a room upstairs but we don't have t…"

"Mark I'm not that demure girl from high school, besides this is your fantasy. So did you bring food to this makeshift Dot?"

"Of course, hot chocolate and chocolate cake," he says producing said things from a basket.

We begin eating and Fitz seems nervous, far more nervous than I ever saw him to be in high school. So I take the lead, feeding him a bite of cake and once he's swallowed it I lean over and kiss him. Licking the crumbs from his bottom lip before I pull away, Fitz now wears a carnal grin and I see the bulge grow in his jeans. I smile and we finish dessert before we go up to his room, but I do grab my things before we leave the ballroom. His room is a floor above Bianca's. He no longer seems nervous just eager, his confidence returned he takes the lead now putting his arm around me and pulling me to him for a luscious kiss. Fitz picks me up and takes me to the bed laying me on it and continuing to kiss me while he takes off my shoes. I've of course had other dates take charge but typically they want to be dominate and have me be subservient. Not with Fitz however, all he wants is to make love to me. When my shoes are off he stands and gets undressed, I smile at his very muscular toned body, perfectly sculpted and I can see his every muscle. He walks back to the bed and pulls me up by my hands, his lips clasp to mine again and he starts to unzip my dress. He unzips it slowly, carefully taking it off my shoulders and lets it fall to the floor pooling around my feet. Picking me up again he takes me to the bed, taking my panties off and smiling at my breasts as I have no bra. Looking over my body with avarice carnality, his eyes glinting with such astonished pleasure you'd think he'd just found buried treasure.

"I've been dreaming of this body for a long time," he grins licking his lips.

Cupping my breasts in his hands he gently kisses around the supple flesh. My body tingles and my flesh excites, he sucks my nipple and I moan. I could take charge but Fitz is doing just fine and anyway this is his fantasy and he wants to be in charge. He sucks each nipple and I moan, I open my legs for him and he gets between, spreading my pussy lips and fingering me a little as his lips reattach to mine. I'll be honest with many dates I fake a lot of moaning and orgasms but not tonight. Fitz knows what he's doing and he's very good at it, I don't have to fake a thing.

He gets out a condom putting it on and penetrates me slowly, I moan as he goes into me, gently spearing me all the way. His lips locking onto mine again as he begins pulling out, for a long time he thrusts slowly, making love to me tenderly and kissing me with much passion and then he speeds up. With each thrust his pace increases little by little until he's going at a furious pace with rapturous abandon. My body aches for release, my hips buck and I grip his shoulders tightly, reaching the peak of orgasm and calling out Mark's name. He cries out mine as he too reaches his climax and his pace slows again. I whimper as he withdrawals, he tosses the condom and lies back on the bed.

"That was amazing, just as I always thought it would be," Fitz smiles.

I smile at him and kiss his lips softly, "I'm glad you're happy but our time is up and I should be going."

"Do you have another date? I'll pay for the night," he offers.

"No it was just you and…another for the night and I already had my first date," I reply nearly slipping out Bianca's name but I can't do that. If they know the other is seeing me they can discuss it but I can't give out names.

"Then stay, I'll pay for the night I can afford it. You can shower, I'll order in dinner if you're hungry. I'd like to make love to you again but o…"

I kiss him to keep him from speaking any further, sucking his lip gently before I pull away, "If you're paying it's your fantasy and I can do anything you want."

"I just want to be with you," he says stroking my cheek.

It's funny he's nothing like the boy from high school and yet he's is exactly the same somehow. We order in food, I shower and then we lie in bed and he holds me. We fall asleep this way, he pays me my fee in the morning and a nice gratuity, I kiss him before leaving and return to the agency.

"You have a full day, well a full evening anyway," Danielle tells me when I enter her office. "I think you owe this OM a free one with all these recommendations he's given you. Tonight you're seeing someone by the code name of Mr. Moneybags, an egotistical alias but you've dealt with that before. You're second date tonight goes by the name of Drummer Boy. All the info is in your room so rest up and eat because you start at seven tonight."

I give Danielle her fee from last night and go up to my room. I put my clothes from last night into the laundry and take off my shoes. Then go downstairs to take a soak in the hot tub in our covered garden, a couple of the other girls are here talking about their dates last night. We do this often without giving names or details to keep the anonymity of our clients.

"He wanted me to crawl around on my hands and knees dressed like a cat! He even had me lap up milk from a bowl before giving him a blow job. Definitely one of the weirder fantasies I've come across," says a girl who calls herself Jasmine.

"I spent two hours getting spanked over his lap, his bare hand, paddles, even a hair brush. I'm still a little numb, at least he tipped well but I'm not on tonight. So what about you D?" Asks the girl that goes by Violet. They call me D instead of Madam D.

"I had a great night, pampering a girl and then a regular date including dancing, dessert and love making. He paid for the whole night so I slept there," I tell them.

"Lucky you, at least tonight my date wants a dominatrix, I prefer being in charge," Jasmine says and I smile.

After my soak I put on jeans, a t-shirt and shoes and go down the street to grab some lunch. I return to my room with my lunch and look at the info for my dates tonight. The first one holds a suite at one of the most expensive hotels in Toronto. All I know is he wants to live out a piece of his favorite literature and he'll provide the costumes. Doesn't say what the literature is or anything else, I've had things like these before, all though it's usually a movie or TV show they want to live out. I've only reenacted scenes from a couple of books; I had one guy that wanted to live out Lady Chatterly's Lover which actually wasn't bad.

The second card wants a naughty school girl and he'll be the teacher. I have a naughty school girl uniform already; we all do since it's quite the common fantasy. As common as it is there are always variations so I should be prepared for nearly anything. The card doesn't say that he wants to dominate, or he wants me to just that I'm to be a naughty school girl and he will be the teacher. I'm even meeting him at DeGrassi, considering it's another recommendation from Owen it could be nearly anyone. I sincerely hope it's not actually a teacher, although I don't think a teacher could afford me, especially now that my rate has been raised.

Well tonight should be very interesting!

Obviously I'm not so cruel as to end the entire shot here; this will be two or possibly three chapters. Chapter 2 will be sometime in February and chapter 3 (if it's needed) sometime in March. I will let you know when exactly when I'm able to get the February and March calendars up. Can you guess who her next two dates are and who else she might see?