Olivia: The Tutor

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This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. It is a fantasy and as such, the story may or may not conform entirely with reality. But isn’t that the whole point of fantasies? With historical exceptions, all other locations, events, and characters are entirely fictitious and any resemblance to actual persons, living or dead, is purely coincidental.

I don’t practice nor do I condone any of the sexual behavior about which I write, other than straight, heterosexual relationships. Other than the fact that most other forms of sexual behavior are illegal, I still don’t judge others for their sexual preferences except where such behavior is hurtful/harmful to others, such as pedophilia.

None-the-less, many people have FANTASIES of such taboo laden behavior to achieve sexual gratification or whatever, but have no intentions whatsoever of carrying out such behavior in actual practice. That said, if I have struck a particular fantasy of yours, read and enjoy.


“John, what do you think?”

“Think about what, Mary?”

“Think about getting a tutor for Sam this year?”

There was a pregnant pause.

“What the hell? Why does he suddenly need a tutor? He’s senior, or will be in one more week and a straight ‘A’ student to boot.”

“Yes, I know that’s all true. But I was thinking more in terms of non academic tutoring.”

“Just what do you mean, ‘non academic’ tutoring?”

“Well, Sam is somewhat lacking in socialization skills.”

“Come on, Mary, spit it out. Quit beating about the bush.”

“Ok, here it is. Sam is quite competent, confident and outgoing in everything except where relationships with the female sex are concerned. He’s very rarely dated his first three years in high school. He’s extremely shy around girls, particularly in one-on-one situations. I thought we might get a tutor on the pretense of helping him study for college entrance exams. But the real intent would be to have this ‘older female’ tutor improve his interactive skills and confidence with the opposite sex.”

Another lengthy pause ensued.

“John, say something.”

“In other words, Mary, you want to hire an older woman to initiate Sam into the world of sex.”

“That would be icing on the cake. I would hope she could do exactly what I said–help Sam develop the ability to deal with females on a level of confidence and expertise that he does with everything else in his life. Sexual interaction is one aspect of the total interaction. Sam just doesn’t have the self image and confidence to deal with that aspect. He needs to acquire that confidence.”

“There was a time, Mary, when a father or big brother took a young man to a favored brothel for that kind of introduction to sex.”

“This way is more subtle, John.”

“Do we tell Sam why we are really getting him a tutor?”

“Good heavens, of course not. We only tell him that we’re getting a tutor for helping him to get through college entrance exams.”

“What do we tell the tutor?”

“I’ll indicate, one way or the other, what my true intentions are. In other words, I’ll strongly hint that any leaning toward sexual relationship abilities is desirable.”

“You’ll indicate; meaning I won’t be part of the interview process.”

“That’s correct. I think, female to female, I can get my true intentions across more easily if you aren’t present at the interview.”

“Oh, yes. What about pay?”

“We’re well enough off that we can make an offer that would be difficult to refuse, especially to a college freshman or sophomore girl working her way through college. A sophomore or possibly a junior girl would be the ideal age difference I had in mind. And, there’s one other factor.”

“What’s that, Mary?”

“Sam’s not an unattractive boy. In fact, he’s quite a ‘hunk’ in the going slang. Girls have crushed on him all through high school but he just ignored them primarily because of his lack of confidence but also because of other and higher priorities.”

“Well, it’s your ball game, Mary, I have no objections. In fact, if anything, I’m envious as hell of Sam’s looming experience.”


“Sam, it’s time to get up and come downstairs. Lunch is nearly ready and you need to get out of bed.”


Ten minutes elapsed with no sound upstairs from Sam.

“Nikki, I guess you’d better go up there and splash cold water on your brother or something–just get him up.”

“Ok, Mom.”

Nikki trotted up the stairs. In a matter of moments, a loud screech emanated from above.


“Nikki, what’s going on? What was that scream?”

“I just did what you told me to do –I dumped a glass of cold water on Sam’s face. He’s awake now.”

“Well, both of you get down here, I’m taking up lunch now.”

A brief conversation drifted down the stairs.

“Jeeze, Nik, did you have to do the water thing? I’ll get you for that one.”

“Promises, promises. Now move or I’ll give you another.”

“Well, get out ataşehir escort of my room so I can get up and dress.”

“What, afraid I’ll see something?”

“Quite possibly since I sleep naked.”

“OOH, do I have to leave.”

“Yes, now git if you want me to get outta this bed.”

“I’m going, I’m going–damn it.”

“Watch your language, Nik.”


“And I don’t need your raspberries either.”

Nikki came down first. A few minutes later, a very ruffled Sam followed into the kitchen.

“Mom, why can’t I enjoy my last weekend. Senior year starts Monday morning and I just want to laze away this last free weekend.”

“Because your father and I have something to discuss with you over lunch before he goes off to the golf course.”

“A family conference? Now what’d I do?”

“You didn’t do anything. Let’s eat first and then talk. I don’t want this hot lunch to get cold.”

Our lunch of tomato soup, grilled cheese, milk, and coffee went quickly with only mundane and sporadic conversation. Nikki cleared the table.

“That was a great lunch, Mom. What’s the big deal now?”

“Your father and I want to hire a tutor for you during the school year.”

“What? Did I hear you correctly? A tutor? What the heck for? I can’t get much higher grades than I’m already getting. I’ve a 4.914 average out of 5 as it is. No thanks.”

“Nik, quit the giggling or I’ll…”

“You’ll what, big brother by two minutes? Come after me? More promises, promises.”

Ignoring Nikki’s comments, I went on with Sam.

“Your father and I are serious, Sam. We’d like this tutor to help make sure you score as high as possible on college entrance exams and scholarship applications.”

“All well and good, but I still don’t need a tutor. I think I can handle those as well as I have my high school academic career so far. Again, no thanks.”

“Sam, this one time of very few, your father and I must insist on this tutor.”

“Aw, Mom, I’m eighteen. I can make that kind of decision for myself.”

“True, but as I said, this time, we insist. We will be hiring a tutor for you.”

“Jeeze, just what I need, more weight around my neck.”


“Well, it’s been two weeks, Mary. How’re the interviews going?”

“Number ten is due in an hour. God, I didn’t think it’d be this difficult what with the salary we’re offering.”

“So what’s been the holdup, dear?”

“In short, Sex.”

“How so?”

“Any mention of the sex angle and, so far, all the girls have backed out right then and there either politely or bluntly. Most already have a committed relationship and are unwilling to take on anything that would threaten that. A few of the others were far too sexually inexperienced for my taste.”


“So, I can’t give up. After Sam’s reaction to our plan, I can’t just cave in with the excuse I couldn’t find anybody to do the job.”

“Well, good luck, dear.”

When the doorbell rang, I was nervous, but ready. I opened the door to an astounding sight. There stood a very pretty redheaded female with green eyes and a beautific smile that showed off her sparkling white teeth to perfection. In flats, she was shorter than my five foot ten by a couple of inches. The young woman was dressed in a shirtwaist dress that ended a bit above her knees. Her bosom, while not monstrous, would turn any male head within one-hundred yards. The rest of her body looked even better, perfectly proportioned. Her eyes sparkled with mischief.

Then she spoke.

“Hi. My name’s Olivia and I’ve come in response to the job advertisement you ran in the papers. May I come inside?”

Her solid English accent hooked me right then and there. I just hoped she could meet the rest of the requirements.

“Yes, please come in. We’ll sit in the library through that door. Would you like some tea, Olivia?”

“Oh yes, that would be just great.”

Nikki brewed some tea for us while I began the interview. I didn’t tell Nikki to leave, but I hoped she would. She did go upstairs after bringing the tea, but I’ve an idea she eavesdropped on the entire conversation.

“Now, Olivia, tell me about yourself, please.”

“I’m English, but I guess you can tell that. I’m here in the States for my junior year at State University as a one year scholarship student from Oxford. I’ll be returning to England in June of next year. I’ll be twenty-one in December.”

“What are you studying, Olivia?”

“I’m collecting first hand information for my third year dissertation on cross cultural differences and their effect on English immigrants to America in the period 1800 to 1900.”

“Oh my, that sounds deep.”

“Not really, it’s a really interesting, at least to me.”

“Have you dated much, either at home or over here in the States?”

“Not here, at least not very much. I’m in a committed relationship at home and fully expect to take up with that when I get back. We have given each other the freedom to see others while I’m gone, but we’re truly committed to each other in the long run.”

“So, that then brings up the kadıköy escort delicate portion of this interview…”

I went on to explain what the real purpose of the job entailed. I talked about coaching Sam on how to get along with the opposite sex, but I also hinted strongly, that if things turned sexual between Sam and herself, John and I would have no objections to that part of his education.

“So, Mrs. Story, you want me to be sort of an older sister coach at the least and maybe the ‘older woman’ teacher of the art of seduction and carnal bliss should such a relationship develop?”

“To put it bluntly, yes.”

“Could I possibly meet Sam before I decide?”

“Of course. He’s out in the shop. I call him up here for a break. You two can talk privately for as long as you need.”

I walked to the intercom system and called out to the shop for Sam. “How ’bout taking a cold drink break, Sam? I’ve also got someone I want you to meet.”

“Be right up, Mom.”

A few minutes later, Sam popped into the kitchen. He was dressed in cargo shorts, barefoot in sandals, and sans any kind of top. Sweat ran down his chest and back. I gave him “the look.”

“Sorry, but it’s really hot in the shop. I didn’t know you had female company for me to greet. I’ll go tidy up a bit.”

“Oh, you don’t hav…”

Olivia was cut off by Sam’s retreating back.

Now Sam wasn’t an adonis exactly, but he wasn’t far from it. He’d lettered in football, basketball, baseball, and track for three years. He was definitely physically fit with toned muscles, broad shoulders, definable abs, blue eyes, and blond hair. Even if he was my son, I’d definitely call him a hunk and then some.

“Ah, Mrs. Story, I’ll take the job, but I still want to talk a bit with Sam.”

“Your happy with the pay?”

“Indeed so. I think I’m happy with the boy as well.”

“Ah, Sam. This is Olivia Littlejohn. She’s from England and would like to talk with you about becoming your tutor. Olivia, this is my son, Sam.”

“Pleased to meet you Sam.”

“Ah, uh, oh, me t-too.”

“Sam, I won’t break if you smile or shake my hand.”

Sam broke his rigid stance to raise his hand to meet Olivia’s outstretched one and got so lost in looking at her that he forgot to let go. She just continued to smile in amusement as Sam continued to hold her hand.

I finally had to interject, “Sam, I think you can let go now.”

“Oh, oh, oh yeah. Sorry.”

“Nothing to be sorry about, Sam, I enjoyed our handshake.”

“You’re English, aren’t you.”

“I believe that was mentioned, son.”

“She talks English.”

“I waved my hand in front of my son. Sam, can you come out of your haze long enough to talk with Olivia?”

Sam shook his head and said, “Oh, yeah, I’m sorry. It’s just that you surprised me, Olivia.”


“Sam. It’s ok. I don’t usually have that effect on people, but I kind of like it. I’m just a girl, Sam.”

“Just a girl, yeah.”

“Since I’m supposed to tutor you, might I ask what’re your grades and what subjects do you like and dislike?

“May I call you Olivia?”

“Yes, indeed, you may.”

“I’ve managed a 4.914 out of 5 by the end of this school year–six semesters. There isn’t really any subject that I dislike: I just like some better than others.”

“Such as, Sam?”

“Tops? I like history, sociology, and human relations the best. But, as I said, I don’t really dislike anything.”

“What about girls. Have you dated much?”

“No, I’ve been too busy to date much. Besides, I get all shy and withdrawn around girls, especially one on one.”

“You seem to be doing alright with me, one on one.”

“Yeah, but you’re different.”

“Oh? Different? How?”

“I don’t know. You just are. Maybe it’s your accent. Whatever it is, I can just relax around you. I realize that much already. You make me want to get to know you.”

“See, it’s not all that hard to talk to a girl with at least some kind of confidence, is it.”

“Well, not with you anyway.”

“So, Sam, do you think we could work together on this tutoring thing? You mother said you weren’t much if favor of it. If you aren’t, it won’t work.”

“Oh, yes. With you, I think I could work very well. Your awfully good looking, too. Are you going to take the job?”

“Why thank you, Sam. You stuck that compliment in there pretty slick. Flattery will go a long way with girls, Sam. And, if you want me to, then yes, I’ll take the job.”

“Deal, Olivia.”

“Sam, why don’t you go find your mother and have her come back in to finalize the job.”

Sam left to do my bidding and I nearly drooled watching him walk out of the room. Three years younger or not, he was indeed quite a “hunk” or a “stud” as Americans say. If it came to it as part of my job, I’d have no trouble with any “personal” relationship between the two of us. A short affair before returning home would suit me fine. Teaching a novice the ropes in that context would be a delight, for both of us, I assume.

I also gave some thought to Sam’s sister, a another really beautiful piece of humanity. bostancı escort She was the female opposite of her blond brother. Also blonde and blue eyed, with shoulder length hair, she had a beautiful face and a body to die for–whether the dier be male or female. Boobs bigger than mine fit her tall frame well, a taller frame than mine. That frame sat atop long, toned, and tan legs that supported trim ankles and feet. These twins really were a matched pair.

Well, Mrs. Story came back and we settled the details. The pay was sumptuous–deliciously outrageous, actually. As for hours, I was to do my tutoring every Saturday from noon until four, longer if the occasion demanded. I would be expected for lunch with Sam and Nikki but “on the clock” as Mrs. Story put it. The job would start one week from the interview, in other words, the next Saturday.

Sam and Mrs. Story escorted me to the door. Before I stepped out, I reached up and gave Sam a peck on his cheek. He turned beet red.

A week later, I knocked on the door of the Story house just as the town clock tower began striking the noon hour. Sam opened the door with a big grin, not to mention a fair bulge in his pants. Seducing him very much appealed to me and I didn’t think it was going to be very hard or take very long, for that matter.

“You certainly seem happy to see me, Sam.”

“Oh yes, I really am.”

Sam was dressed in jeans, Tee, and sandals. September was still warm, so I was dressed in a sleeveless top, modest shorts, and sandals sans socks. My toenails were natural–I never painted them. My fingernails were also natural colored.

Sam ushered me into the kitchen where his twin sister Nikki was just finishing setting up lunch.

“Hi, Nikki. How’re you today?”

“Oh, Hi Olivia. I’m fine thanks. And you?

“Just great.”

We chatted and ate. Then Sam took me up to his room where we studied for nearly four hours. I did nothing overt–just allowed him to surreptitiously ogle me and catch a glimpse now and then past my blouse arm holes. He certainly did plenty of that. I suspect that by the time he ushered me to the door at the end of our session, he had quite a bad case of blue balls.

Just before stepping out the front door, I again gave him peck on his cheek–a little longer one that time. He again turned beet red and blinked. I swear his bulge grew larger.

“See you next week Sam.”

“Yeah, next week, Olivia.”

We followed almost the identical routine until right before Thanksgiving. One change did occur though. I think it was about the third Saturday, Sam kissed my cheek in return. I smiled. Sam kissed the other cheek. His prominent bulge was quite obvious.

“Next week, Olivia.”

“Bye, Sam.”

I think it was the first Saturday after Thanksgiving that the next step in our relationship occurred–Sam had been obviously ogling me more each week. I teased him by leaving more blouse buttons undone than necessary and just the week before, even arriving sans bra–a practice I continued thereafter. I wore short skirts and was none to careful about how much I let show when I sat, stood, or crossed my legs directly in front of him. I did continue to wear a string thong, though.

On his part, Sam slowly grew more aggressive (subtly) in brushing against my body. A breast graze here, a thigh bump there, and so on. I didn’t discourage such contact, but neither did I initiate any in return. I just played dumb about the touching. I simply continued to give him eye candy.

I believe it was a week or so before Christmas that our relationship considerably intensified. For one thing, it was the second Saturday that I came sans thong, pussy baby bare. So, Sam was quite nervous and fidgety that Saturday when he met me at the door. He’d not calmed down yet by the time we got to his room. I was curious.

“What is it Sam? Your up tight about something. Talk to me, Sam.”

“Uh, er, uh.”

I just waited. I found I got much further getting people to talk if I just waited them out. People just can’t stand long pauses for some reason. I didn’t say a word, I just stood in front of Sam with an expectant look on my face.

At last, Sam just blurted it out.

“Oh God, Olivia, I just want to kiss you so bad. In fact, I want to do a lot more than just kiss you, but I don’t know how. I’m also afraid you’ll just slap me down and leave. I’ve never kissed or done anything else with a girl.”

I ignored the part about slapping him down when I replied, “Not even your mother or your sister–kisses I mean.”

“Well sure, but that’s not the kind of kissing I mean.”

“What kind of kissing do you mean then?”

“Oh, I, uh, sorta, uh…”

“You mean like this?”

I stepped right up to Sam, took his head in both my hands, stood on my tip toes, and gave him a smoldering kiss. The kiss went on and on and… Well, we didn’t break until we nearly dropped for lack of air. It didn’t take very long for that kiss to turn into a delicious French kiss, either.

Before that kiss ended, Sam grabbed me in a clutch and crushed me against his body–chest to chest, groin to groin, thigh to thigh, toe to toe. My nipples went erect so quickly, I nearly poked two holes into his chest. His cock was quite fully erect, mashing and grinding against my pussy so hard that I quickly developed a fast growing wet spot in my panties and slacks.

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