Jack's Sex Tutor Ch. 03

When Jack woke up the next morning and went into the dining room for breakfast he was apprehensive about facing her after the hand job she had given him the other day. As he walked into the room though he was met with her smiling face.

"Oh Jack, I'm going to be in town all day running errands, but I've got it all organised, your new tutor should get here around 10:30. Looking forward to your new studying?"

Jack just nodded. He couldn't believe she'd actually done it. He knew straight away she was planning on going out and getting laid, but he just couldn't care at the prospect of maybe getting more hand jobs (or maybe more) from what he assumed was a hooker that Kate had hired to keep him entertained.

=====

After breakfast Kate sent Jack to his study room to wait for the arrival of his new tutor, while she went out to run her "errands" in a low cut, tight fitting t-shirt and mini skirt.

Not long after entering the room and tidying the desk up slightly he heard the door bell ring. He lent on the desk, facing the door waiting for the arrival of his hooker "tutor".

He was shocked when the women that opened the door looked like a completely respectable woman. She was wearing black high heels and black stockings. She had on a black business suit jacket, under which was a white shirt. She also had on black knee length skirt. Nothing terribly erotic then, although she was a very attractive woman. Tall and slim with long legs, her long black hair was drawn up in a bun and held in place by two of those hair sticks that always reminded Jack of chopsticks. She looked to by in her late twenties. She was carrying a large bag by her side.

"Hi" Jack said, thinking he had got the wrong impression from his stepmom the day before. "I'm Jack."

She looked him over in an appraising manner before replying. "My name is Melissa Hallin, I'm your new sex tutor. Take a seat please."

Jack sat down on one side of the desk facing the chair which Melissa then occupied. He decided to find out if this was just going to be an extended sex ed class and Kate had just been messing with him. "Umm, Ms Hallin. What exactly am I going to be learning?"

"Your mom told me that she wants you educated in all areas of sex, so that's what I'm going to do. When I'm finished with you you'll fuck like a pro."

The smile came back on Jacks face until she started talking again.

"Today's lesson will cover talking to and picking up girls."

So it was just a slightly skewed sex ed class after all.

"But I already have a girlfriend."

"Yes but you're going to need to pick up some girls to practice my advice on first. You don't want your first time to be with your girlfriend, trust me."

So now it seemed like he'd be having sex after all. Jack decided to give up on trying to figure the situation out, it was too bizarre. He'd just go with the flow, at the very least he might learn something.

"What have you done with your girlfriend so far?" Melissa asked.

Blushing, Jack replied "Uhh, kissing..."

"With tongues?"

"No, also she lets me play with her tits sometimes..."

"Hands under or on top the clothing?"

"On top."

"Wow, she sounds pretty frigid." Melissa said. "And your mom told me she was a cheerleader too. Maybe she's a lesbian." She teased.

"It's not that. Were just waiting for her to be legal age like I am. It's her birthday in 3 weeks, so it's not long now."

Jack felt that he had to defend himself for not getting any further with Sarah. The stereotypical cheerleader didn't apply to her.

"Well don't worry, you'll soon be getting all the pussy you can eat" Melissa said with a grin. She then stood up then sat with her butt perched on the edge of the desk. "Now, pretend I'm hanging out somewhere, I want you to come and chat me up."

Jack wasn't very good at this kind of thing, so he normally kept it short and simple. Walking up to her he said "Hi, my name's Jack, can I buy you a drink?"

"Not bad, it's nice and simple, you say hi and give you're name, and by offering to buy her a drink you are showing that you don't mind spending money on her. It shows obvious interest, plus it has the added bonus of getting her drunk. The downside is you're underage, so I doubt you'll get much chance to use that yet as you wouldn't be able to buy her that drink. Also there's nothing in what you said to entertain her, or capture her interest, besides the offer of free booze."

She then took Jack through a number of replies girl would give him and he had to then have a suitable reply to that.

"Now, there are different styles of chat ups for different types of girls. Obviously if a girls a bit tipsy and is dressed like a slut, she's more outgoing and you can probably get away with being more direct like slapping her ass."

She then went on to show how you could identify what kind of girl would accept what style of chat up line, and also which type of girl he would have a higher percentage of scoring with.

After that they went through an extensive list of pick up lines, first Melissa would state the advantages and disadvantages of each one, as they worked through the styles. Then Jack would try them out on Melissa as she replied with all the possible replies.

Eventually they got to the more direct ones. Melissa stood up and faced away from Jack.

"Come and slap me on the ass." She ordered, pushing her ass out ever so slightly.

Standing up Jack nervously approached and gave her ass a half hearted pat.

"You've got to really spank it!" Melissa urged. "Try again."

This time he pulled his hand back and got a bit of power behind it making an audible smacking sound and making Melissa let out a small yelp.

"That's better," she breathed, rubbing her left bottom cheek furtively "but slightly not so strong as that. Now try the just a grope."

Jack put his hand on her right cheek and gave it a little squeeze. He had tried this before with Sarah while they were making out, but she always stopped him, saying she didn't want to get him to excited.

Melissa had a well rounded but still tight ass. Although Jack would have preferred to feel it without her dress and panties in the way, but it still felt just fine. He could stand there and squeeze it all day.

That is until after a while she turned her head and said "in reality, she would have turned around a lot sooner."

Blushing Jack let go, but as Melissa started to turn around, he said "I've got an idea for one more."

"Oh really now?" Melissa smirked, but she dutifully resumed her position.

Adjusting the erection he was now sporting, Jack postioned it under his trousers so it was pointing straight out in front of him.

"Oops" he said, then gave Melissa a little push, unbalancing her in her heels. Placing his hands on her hips he held her as if to steady her and stop her from falling but instead it was so he could pull her gently backwards and press his dick in between her ass cheeks. He only wished she had been wearing jeans instead of skirt so he could have rested it right under her pussy lips.

Melissa laughed "Well, that'll certainly get their attention." Then she actually ground her ass on his cock for a second before pulling away.

"I think it's time for our lunch break, come on." And she walked out the door towards the dining room.

Jack would have liked nothing better then to go jerk off his impressive hard on, but he dutifully followed her to go eat lunch.

=====

After lunch, back in the study, Melissa declared that the final part of getting a girl to bed, was dancing with her.

"But I can't dance" Jack protested.

"I thought as much" Melissa exclaimed "that's why I set aside this whole period to teaching you."

Jack then learnt a whole host of dance moves, culminating in Melissa grinding her ass against him like she had done previously, leaving him with another erection.

"Phew, times almost up for today" Melissa said. "There's just one more thing to do before I go. Strip."

"Huh?"

"I need to see what I'm working with here, so I can plan out the rest of your lessons. Now get naked."

Nervously, Jack started getting undressed, until he was standing in front of her completely naked.

"Well well, your mom was right. You've got nothing to be ashamed of. A nice fit body, nice and slim, although maybe you could do with a bit more muscle definintion. And that cock is amazing. Turn around."

Jack turned around and after a couple of seconds felt a hand grope his ass like he had down to her earlier. "Nice ass" he heard her whisper softly by his ear.

Snaking a hand around from behind she grasped his cock in a firm grip. "Well, now I know you've got plenty to offer we can get right to business. Next lesson, will take place in your bedroom."

Jack desperately wanted some release for his cock, but he managed a nod.

"Also, I've noticed you have a slight confidence problem. So from now on until I say otherwise I want you to flirt with every member of the opposite sex you meet. If they're people you know, start extremely subtly, with small compliments maybe. But if they're people you've never met, I want you to be outrageous in your come ons."

"Uhh... ok."

Jack couldn't take any more, he started making minute thrusting movements with his jips, hoping Melissa would get the idea.

Her hand instantly sprang away from his cock. "Sorry Jack, but as much as I love my job I don't work overtime for anyone."

She reached into her bag and pulled out a couple of sheets of paper. "Here's some exercises for your muscle definition. I want you to do these every evening." She put them down on the desk then turned to him grinning. "Now, you don't want that to be the second hard on you got today with no release do you? Go down the corridor to the bathroom and relieve yourself."

Jack looked behind her at his clothes, but he knew she meant for him to do this naked. Opening the door slightly he checked if the coast was clear before rushing to the toilet and locking the door.

After cumming explosively he cleaned himself up, then unlocked the door, and opened it, forgetting he was naked.

Kate was standing right in front of him, she must have got back early! She gave a start when she saw him naked, but she quickly smiled. "Wow, it looks tiny when it's not erect."

Jack blushed and covered his privates. It was a source of embarrassment with him that with some guys they always had large cocks, and when they got an erection their dicks just got harder. Jacks dick was only 2 inches long when limp, so it looked like he had a tiny cock, until it ballooned up to size whenever he got an erection.

"Are you enjoying your lessons with Melissa?" Kate asked.

Jack just nodded.

"Good, because I plan to test you on your progress after a couple of weeks."

Jack stared at her as she walked away laughing. Tehn, pulling himself together he ran back to the study to get dressed and pick up the exercise sheets. There was only 10 minutes until his first tutor arrived for the evening.