The Sex Tutor Pt. 01

"What's the matter, dear?" Kay could see that her normally happy-go-lucky daughter was distraught about something. She had barely taken off her stylish new spring coat when Holly appeared in the hall, looking forlornly at her mother.

"Did something happen at school?"

"No."

"Is it your new boyfriend? Did you have a spat with Kevin?"

"No, not a spat. At least not a disagreement."

"What was it then?" Kay adored her daughter and understood that she would want to talk over whatever was bothering her. She knew Holly practically worshipped Kevin and would not want anything to come between them.

"It's embarrassing to talk about."

"You mean it's about sex?" Kay knew her daughter had been going with Kevin for several weeks and intended to have sex with him. Kay approved. After all, Holly was eighteen now. At 46, Kay remembered the exploration of sexual pleasure as one of the glories of her youth.

"Yes. We talked about it for the first time last night and it was new to me but not to him because he had done it before with other girls. I could tell he expected me to know all about what to do, but I don't know what he wants." She burst into tears.

Kay sensed that Kevin was not particularly the talkative type and wasn't surprised they hadn't been able to discuss the problem. She would have to find out what was going on.

"Tell me what happened and maybe I can see a way to help you." Mother and daughter had always been able to talk about anything.

"Well we made out for a while and then he said he wanted to have sex on our next date when his parents will be out and we'll have a place alone. He told me he really enjoyed hot sex. I didn't know what he meant. I've got no experience and he done it with other girls, I think."

"Did you ask him what they did that he wanted you to do?"

"Not at first. I couldn't bear to ask him what those girls did. Finally I asked him what kind of sex he meant."

"What did he say?"

"He said he wanted to be teased. 'I want a real cocktease,' he said and then sort of clammed up. I got the idea he thought I should know what that means because other girls had given it to him." Kay comforted her daughter as best she could. Holly was somewhat immature for her age. Despite her generally sunny disposition, she suffered from typical teenage anxiety about dating. Kay hoped she would mature without too much distress. From her long experience she had some idea what Kevin might have in mind. She also knew she couldn't really teach her daughter this sort of thing. It would take a male.

"I think what you need to do is to learn more about this before seeing Kevin again. When is your next date?"

"Well, we planned to do it tomorrow, Saturday night."

Kay thought for a moment.

"That's not much time. Look, only a guy can show you this stuff. I've got an idea that might work. Just listen for a moment."

"OK, but I can't just ask some guy to tell me, can I?"

"No, not just anyone. What you need is a man with lots of experience who can teach you the tricks. I think it's possible that Michael might be willing to help."

"Mom! Your boyfriend? You must be crazy! I mean, he's older than you and wouldn't ever do something like that. I'd be mortified if Michael knew we were even talking about this. It's impossible!"

Holly was genuinely appalled. Her mother's latest boyfriend was 52 years old, a mature man who behaved like a gentleman in every respect. She had only met him a couple of times coming or going. He was invariably nice to her and seemed to really like his mother. She wouldn't mind if they got married, though that didn't seem likely very soon. Holly couldn't imagine what her mother was thinking by bringing the subject of Michael up.

"Look, darling," said Kay. "I know it seems crazy, but hear me out. Guys aren't all the same when it comes to sex. They have very individual tastes and desires, so you have to learn a lot of different things to please them. Michael is very experienced sexually, so he can show you everything you need to know. I also know he likes a lot of teasing. If he can be persuaded, I'm sure he'd make a really good teacher. I don't think he'd refuse because he wants us to be happy."

"No way," said Holly. "I couldn't possibly ask him that. It's too embarrassing. What would he think? It's impossible... Besides, there's not enough time. "

"He won't do it unless he knows you really want him to. I'll explain everything to him first. Then, if he agrees to talk to you, you'll at least know he's open to the idea. There is nothing to lose. As for the short time before your date, he works at home and could easily make time for you."

Holly looked doubtfully at her mother. She was aghast at the idea. At the same time, she really wanted to make Kevin happy and couldn't see another way to learn what she needed to know, and fast.

"I'm sure he won't want to embarrass himself like that. Go ahead and talk to him; I'm sure that'll be the end of it."

"I'll ask him to come over here right now. His condo is only ten minutes away. I'll take him into my bedroom and explain the situation to him. If he agrees, we'll all talk and see if it can be agreed."

"OK, I guess," said Holly doubtfully. She still didn't like it, but her mother was insistent. Holly felt confident Michael would balk at the idea anyway.

Michael Handlin agreed to come over when Kay called saying only that something important had come up and he could help. They had been going together for almost two months and got along well. Kay was so upbeat and cheerful. Her daughter was much like her, though even sunnier with the bubbly enthusiasm of youth. He wondered if he would ever get married again. Right now he enjoyed his time with Kay and wanted to help her, if he could.

Kay greeted him with a big smile and a kiss.

"There's something I need to talk to you about. Come into the bedroom for a minute."

"OK." Michael said hello to Holly and followed Kay into her bedroom, a little curious.

"Michael, I need a favor. Or rather Holly needs one. I know it's a lot to ask, but you can really help her out. I wouldn't ask you if there was any other way."

"I'll help if I can. What is it?"

Kay carefully explained the problem, leaving nothing out. "So you see what her problem is. She doesn't want to lose Kevin. There's no one else to ask."

Michael was stunned. It's the last thing he had expected. He knew that Kay was rather open-minded about sex, but nothing like this. "I don't know what to say. Kay, I can't imagine doing something like that with Holly. She's just a girl."

"She's 18 and she's wants to have sex with her boyfriend. You know what he's getting at, don't you? I mean you have experience with that sort of thing, cock teasing, don't you?"

"Well, yes. I can guess what he likes. Many men like to be teased, some quite a bit. But I can't really imagine that Holly would want me to teach her about it. I can't believe she would ask me that and I certainly wouldn't ask her."

"I know it's...well...unusual, but you could really do her a great favor. Look, just agree to talk to her. If she asks, then you will know it's OK with her. I'll be there to reassure you."

Michael sighed. "I suppose I can hear what she has to say."

"Good. I'll talk to her first to let her know you will hear her out." Kay left the room quickly and found her daughter in the living room.

"He has agreed to consider it. All you have to do is to ask him. I'll be there to help."

Before either one could consider further Kay had the three of them together. She ignored their obvious discomfort and plunged on.

"OK. We all know what the problem is and how it might be solved. Isn't that what you want, Holly, so that you can keep Kevin?"

"Well, yes, I guess so. It's so embarrassing to talk about."

"Don't worry about that. Michael is ready to help, if you want him to. How about it?"

Holly looked uncertain for a moment.

"It's OK with me if it's OK with Michael."

"What do you say, Michael?" asked Kay.

"If Holly wants my help, I'll give it a try." Michael surprised himself at his answer. He rationalized it by thinking that Holly would probably only want to talk about sex, not to do anything with him.

"Good," said Kay. "Then it's all agreed. But you can't do it here; Jeff will be home soon and you will need all the time you've got before tomorrow evening." Jeff was Holly's younger brother. "You could go to Michael's place after fixing yourself up a bit first. You'll have complete privacy. Go home now Michael. Holly will be there within the hour."

"Take a shower, dear," said Kay after Michael had gone, "and then we'll pick out some outfits for you to take with you."

Holly nodded, somewhat in a daze. She decided to just do as her mother asked; everything had happened so fast she really couldn't think straight. Kay took Holly into her bedroom and scrummaged for various items of lingerie from the drawers. "You'll need these things. Michael really likes them, like some males I've known. I don't know about Kevin, but you've nothing to lose." She put the items in a large grey bag for Holly to take with her.

In the shower after he got home Michael wondered whether he had been dreaming. The whole situation was unreal. Probably the girl wouldn't show up and that would be that. If she did come most likely they would just talk about her problem and he would offer some advice from a male point of view. He certainly wasn't going to do anything with her, unless she wanted it.

He looked down at his thick hung penis. Noticing some grey hairs, he decided to shave around the base and balls, just in case. He dried himself off with a towel and looked in the mirror.

He was pleased with the result. His cock was his most prominent feature, exceptionally large and well-shaped. Most women he had been with loved it, but some found it too much. If Holly unexpectedly did really want to go through with it and he ended up fucking her he would have to be careful not to hurt her. Maybe it was just too big. Anyway, they would probably just talk. He sighed and dressed quickly.

Walking up to the condo carrying her bag with the lingerie her mother had provided Holly felt determined, yet also anxious about having enticed Michael into something he probably wouldn't do. Her crazy mother had put her in an awkward situation. She was eager to learn as much about sex as possible before her date with Kevin but surely Michael would have second thoughts. If he would go through with it, she would. She screwed up her courage and rang the bell.

Michael opened the door and greeted Holly with a somewhat shy smile, trying to hide his surprise that she had showed up. Holly gave him a smile in return as she entered the condo. Her ample golden hair, in the customary lush ponytail and bangs, looked nicer than usual, perhaps because of the extra makeup she had put on.

"I wasn't sure you'd come," he said.

He was struck by how young she looked. He and his ex-wife had a daughter aged 26. This girl was a lot younger, pretty as a kitten and very bubbly and sweet. He endeavored not to betray the nervousness he felt when he thought about what they might do together. It might be best to treat her as a daughter and just offer some friendly advice.

"I wasn't sure either until Mom reminded me that you'd be a good teacher and would be willing to help me out. I really want to learn everything I can. Not only for Kevin, but so I'm never ignorant with boys again." Holly had her mother's plucky spirit.

"If you really want me to help I'll give it a try."

Michael had never really looked closely at Holly before. Most teenagers today looked alike to him, or at least they dressed alike. She was wearing some kind of blue sweater jacket and what looked to be dark pants, not very revealing. As far as he could tell, she was built rather like her mother, with a round full figure.

"Maybe we should talk a bit first, to make sure we understand what's expected," he said as she sat on the soft white couch. "What is it you want me to teach you?"

"Well, everything. I mean about sex, that is. I really don't know much about it, you see, because I've hardly done anything yet." She felt immediately comfortable with this older man who treated her kindly without the risk of rejection which seemed always present with boys her own age.

"What have you done?"

"Well, kissing and that stuff. And then after I started going with Kevin last month we played with each other, you know. I rubbed his cock and he put his fingers in me. Then I made him cum with my hand." She blushed a bright pink.

"Did he like it cum?"

"Yeah, I think so. It didn't take very long, just a few minutes."

"Did you cum?"

"Not with him, though I came close." She blushed again.

"So you're a virgin, actually?"

"Well technically, yes. No guy has yet been inside me, if that's what you mean. I know how to cum, though. I've got a dildo thing and do it to myself all the time." She giggled and they both laughed.

"Well that's a good start. At least you know sex can feel really good. But I can see you have a lot to learn. Do you want me to just explain what I can, or do you want me to show you? I mean do you want to try things out?"

"Oh, I want to try with you. I learn best by doing and there's no better way to get it right."

"OK," he said. "We'll have to get undressed first, if that's OK?" He was going to take this step by step.

"Sure. I brought some lingerie things Mom told me you would like. We can mostly wear the same size, so you've probably seen them before." She gave him a bright smile.

"Yes, I love that sort of thing." Jeez, Kay had really put her daughter up to something, he thought.

"If it's OK with you, I can go in the other room and change"

"Yes, it's OK," he said. She left the room with the bag leaving him somewhat jumpy to say the least. He wasn't sure how this might go, and was playing it by ear. He quickly undressed and put on a heavy white bathrobe.

When Holly came back into the living room Michael was stunned by what he saw. She wore only a pink bra, matching silky garter belt, sheer thong revealing a glimpse of neatly trimmed pussy, black stockings and high heels which Michael vaguely remembered having seen before on Kay. He was surprised at how much Holly resembled her mother. She had the same clear golden skin, big round voluptuous tits and thighs, with the daughter rather thinner in the waist. The push-up bra emphasized an astounding amount of cleavage. A full big ass made up the rest of the package.

"You look lovely, "he said admiringly.

"Thank you," she smiled, preening herself a bit. "My mom said you'd like it. I really like dressing up in lingerie and stuff. "

"Why don't you sit in that chair there for a moment? We can start by learning the ways men get aroused." He stood in front of her still a little unsure how far she wanted to go.

"First of all you should know that guys can get sexually excited by sight alone, without being touched," he began. "Sometimes all it takes is thinking about a sexy girl or scene. So for example my penis could get hard just looking at you posing for me."

She giggled. "That's cool. I'd like to see that."

Kevin thought he might as well go for it now.

"Is it OK if I open my robe?" he asked, trying not to appear anxious.

"Yeah, please do, if you don't mind. I'd like to see."

He loosened the cord and opened his robe, displaying his fat cock hanging out which took up a remarkably large portion of the space between his long thighs. Though only partially erect, it extended almost half way to his knees.

"Oh my!" said the girl laughing and giggling the way teenage girls often do. "I never realized a guy could be so huge. I mean Kevin's seems really big to me, but yours is even bigger." Holly looked up at him with an expectant smile. She hadn't expected anything like this and marveled that he could put that thing into her mother. Of course he must do it, she thought, wondering what it would feel like inside her.

"Don't be alarmed, but it'll get quite a bit harder when I get excited. I'll sit in that chair and you go over by the couch." He said down, leaning back in the chair and spreading his legs so that his penis hung out in front of him.

"How do you want me to pose for you?"

"The idea is to look as provocative as you can. The sexiest parts are your thighs, butt and pussy, especially with your legs spread apart exposing yourself to me."

"Like this?" she said spreading her legs. Michael could now see the outline of her cunt through the sheer pink panty.

"Yes, that's the idea. Now try to vary the pose in different positions, standing or sitting. Just remember the guy is going to be looking between your legs."

As she assumed different positions, always keeping her thighs well apart he could see that she seemed to relish exposing herself like this to him.

Holly felt quite comfortable doing this. Since she was very young she had always liked to perform for people. Kevin was so friendly and appreciative that is seemed natural to her to pose for him. She was also a bit of an exhibitionist.

Kevin felt his cock beginning to stiffen. Holly lifted one leg up on the chair arm and turned toward him. Then she sat on the couch and assumed the same position he had, leaning back while thrusting her pelvis toward him with her legs spread.

"That's great, honey," said Kevin. "I like that a lot."

"Oh my! I can see it getting bigger." She gave him a big grin, delighted that it was working.

"See, you're doing great. Keep your eyes on me or my penis, don't' look away or close them, and keep changing the pose from time to time. It won't be long now."

She looked very pleased as his cock rose up straight in front of him.

"I now see what you mean about it getting even bigger when you get excited. Does it feel good when it gets stiff like that?"

"Yes, an erection feels good. Would you like to take off your panties? That would make it get even harder."

"OK." She slipped them off, displaying her beautiful pussy trimmed with a shadow of light brown hair. She reached down and slowly pulled her pussy lips apart.

"Do you like the way my pussy looks?"

"Yes, very much. He felt a strong response in his loins. He realized that he really wanted to fuck this girl but would be careful not to proceed any further than she wanted.

"I haven't been sure whether or not to completely shave it. I think many girls do that. What do you like?"

"I may be old fashioned. I like it the way it is now."

She beamed at him. "I'm so glad you like it, Michael. It makes me feel wonderful to know someone likes the way I look. Do you think I need to lose weight?"

If she had been more experienced, she wouldn't have had to ask. The swelling of his penis answered her question.

"No, I like you just the way you are. I think your figure is perfect for me." She continued to pose for him for another few minutes.

"OK, I think it's completely hard now, just from watching you in those sexy poses. Come over here and feel what I mean."

Holly knelt before him and shyly wrapped her hand around the shaft.

"I see what you mean. It's gotten very hard!"

"Give it a good feel. The whole thing is sensitive to touch. The most sensitive parts are the head and the underside."

"OK. " She giggled and then ran her fingers over the tip and down the front and back. "Does that feel good?"

"Yes. Now let's try something different. How would you feel about putting it in your mouth for me?" He was very aroused and feeling bolder.

"Oh, I've heard about that. Girls give guys blowjobs and stuff. I want to learn to do that."

"Put your mouth over the top and suck on it like a lollipop."