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Building Her Sons Confidence

Building Her Sons Confidence

by jacflash1959
19 min read
4.68 (55500 views)
adultfiction
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This is a fictional story about a mother, son, and their psychologist working to build a young man's confidence through sexual engagement. If this is not what you are looking for, please enjoy a different story.

APRIL:

CEO and owner, Greta Gooding approached the podium and faced her colleagues with her trademark brilliant white smile. They stood and clapped, and the applause was wild. And with very good reason. Ten minutes ago, the Chief Financial Officer had just announced their annual corporate earnings were 67% over the budget. Five minutes ago, the Senior Human Resources Officer announced Greta's decision to share the profits with every employee with a bonus amounting to a 40% salary bonus.

Some, most notably on the board of directors, said it was a mistake. It would set expectations too high for the next year and there was a good probability that there would be dark days ahead.

Greta's husband had created the small software firm, with a few novel ideas. Over the last five years, it grew from 15 people to a group that could barely fit into this 500 person auditorium. Two years ago, her husband died of a massive heart attack. The multitude of corporate lunches, dinners, overweight, and his heavy drinking finally took him down. With his death, she owned a largest stake in the company all by herself, but it wasn't enough to completely control the company. She still needed a few board members to vote with her on controversial matters... like giving employees a huge bonus.

She'd been a computer programmer in her younger years and knew the business well. After her husband's death, board members, counseled her to hire a "professional CEO" to run the company. But the interviews all fell flat. She took the job herself instead and decided to revamp the entire company management structure, only keeping 25% of the original team.

It was drastic but it worked.

Holding up her hands, she asked everyone to sit down and relax. They yelled more wildly and laughed as they stomped their feet and clapped even louder.

She smiled and fanned her face as if she felt flush. Thinking back, getting this company back on its feet after losing its CEO was quite the challenge. She'd done a great job but ... it meant she never really grieved the loss of her husband.

Like many, she just pushed on.

Greta had a son and the effect of losing his father worried her. He grew tall in his high school years, and to be honest, standing at 6 feet 4 inches, he often seemed awkward and gangly. His father had little time for him, which affected his confidence and pushed him even further away socially. He had few friends. The loss of his father may have confounded his confidence even more.

That was one of the considerations when Greta took the job. Kyle was still in high school, and she needed assurances that she could be there for him if he needed her. The truth was, Greta hated the spotlight and was very much like her son, technically bright... but socially awkward.

She just needed some more time to teach her son. He needed some more time to learn how to fake social interactions, like she did!

As she began her speech, she smiled broadly just like she had practiced. All of her leadership and all of her social interactions were always practiced ... because at heart, she was a software geek, not a CEO. But here she was, and she dove into her speech to the excited crowd.

MAY:

Kyle woke up early on Saturday morning. The dinner with his mom had been pleasant enough until they drank too much and she started asking those "probing questions." Ugh! He just didn't want to talk about that stuff. Frankly, he'd be happy to just not talk about anything ever again. He thought seriously about taking a vow of silence.

He was 18 now and felt good about getting out of high school. He worried about his future. They were the usual things that every kid his age worries about, but to him it didn't feel usual. He obsessed over them. He was accepted into early admission for an Ivy League school and jumped on it, but he worried that everyone would be smarter than him. He worried about dating in college. He lacked experience with girls. There were many of his high school friends that were no longer virgins. He was still was a virgin and just didn't know what to do. He watched some pornos, but he still felt ... clueless and awkward.

Greta stepped down the stairs and Kyle tried not to look.

Long slender legs took each step with a slight bounce. She was wearing a two-piece pajama set. Black silky shorts with a matching button up top. The top three buttons were undone. Her braless breasts bounced with each step, nipples poked out of the thin material, and thick black hair curled gently down and around her pretty face.

Damn, she looked great for 42. Damn, she looked better than any girl in his private high school, too.

She sat down. "I've got a hangover!" she declared.

He said nothing but glanced down her blouse as she rubbed her temples. He finally pulled himself from her spell and got her a cup coffee. This also afforded him a better look down her shirt.

"Honey, did you remember to call your doctor?" she asked.

"No idea what you're talking about," he responded as he got her cream.

"Your college requires a doctor's evaluation. It's a requirement."

"OH, now I remember. No, I didn't."

"I didn't think so. So, I called a friend. She can take you today, at 4pm."

"Um, thanks? Who is this?" he asked.

"An old friend from college. She a doctor and a therapist. I need you to talk to her, open up to her. If you do, she'll do us a favor and give you approval with short notice."

"Why? Can't I just go to a regular doctor?"

"Well, you were supposed to do it and you didn't. Now, you're out of time. You had that chance and it is gone. So, this is all arranged. Go get your physical, talk to her, and listen to her. C'mon Kyle, don't debate this with me!"

Amanda didn't like working on Saturdays but when a friend calls, a friend calls. And Greta Gooding was a very good and old friend. They went to college together and shared just about everything with each other. Greta was the kind of person who was quiet and reserved but could turn on the mega-personality when needed.

Amanda sent her staff home at 3 pm, got lost in her paperwork and was startled when there was a soft knock on the door from Kyle Gooding.

She invited him into the office and smiled as she could see some of his mother in him. The eyes were a soft green, their shape like almonds, his skin had her dark tones, his hair was thick, dark, and unruly like hers too. There was his father in there, too. The angular chin, the dimples in his cheeks, and his father's big hands.

Greta had prepared her for his low-key personality. She expected him to be shy, but he was more than just shy. He answered most questions with either "yes," or "no," preferring silence over filling in gaps with idle conversation. Greta told Amanda that she worried that he was having issues with girls. He'd had only one girlfriend, and that was for a very short time. When she left him, he was devastated and wouldn't talk about it. He was always shy but since then, he'd become introverted. After his father's death, he barely talked.

Amanda's official job was to give him a physical examination for his college entrance, but her unofficial job was to see where he might need her help to mature and grow emotionally so that he could be more social when he went to college. That was Greta's greatest concern.

As instructed, Kyle sat his tall and slender frame on the edge of the examination table. Amanda was pleasantly surprised by his muscle tone. He was thin, looked gangly, but was toned and well-muscled.

As she took his blood pressure she asked, "My, you seem physically fit. Do you work out?"

Kyle paused, waited a moment or two and asked, "Mrs. Robinson, are you trying to seduce me?"

Amanda smiled at the 1967 movie reference. He had a sense of humor! Not all was lost. Maybe he wasn't all that introverted.

He added, "Yes, I do stretching and yoga almost every day."

"Kyle, in this appointment today and any follow-up appointments, you are protected by HIPPA. That means, anything we say or do in here is between you and me. I am required by law to protect your privacy. And I will do that. No matter what you have to say."

"You won't tell anyone?"

She nodded.

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He nodded while wondering what they could talk about that required that declaration.

She had him take off his shirt and then take off his shoes, socks, and pants, leaving him in his boxers.

"It's cold in here, isn't it," she said easily and turned up the heat on the wall.

She checked his feet, ankles, shins, knees, and as she moved her manicured hands up his muscled thighs, he jumped a bit.

"All good?" she asked. He nodded. "I'm going to have to examine your penis. Is that all right?"

"I'd rather you didn't," he said softly and sat hunched like a mouse.

She knew that eventually he'd give in but added, "Can't have you going to college and spreading a bunch of STDs, now can we ..."

"I know that I don't have any," he answered and surprisingly added, "I'm a virgin."

"Lots of people are virgins when they go to college but very few are virgins when they leave!" she smiled. "It's no big deal."

It was hot in the room now. She remembered him checking her out and took off her white lab coat, "I'm hot! I guess I overdid it on the heat!" She unbuttoned two buttons showing him some of her ample cleavage.

Unlike Greta, Amanda was a bigger woman with heavy, mature breasts. They hung like torpedoes, thick, wide and full. Her bra barely held them in check. You wouldn't say she was fat, you would say she was... full-figured.

"Kyle, I have to ask you some personal questions and it's important that you are honest with me. Again, none of this will go back to your mom or anyone else. It's safe here. Okay?"

Kyle nodded, his eyes focused on Amanda's buxom chest.

"First, are you attracted to women?"

"Yes," he croaked out.

"Are you attracted to men?"

"No," he said disdainfully.

She made some notes on her tablet.

"No judgement here," she laughed. "Next question. How many girls have you dated?"

"Just one," this was said somewhat sullenly.

"That's unexpected," she murmured and he gave her an odd look. "Unexpected because you're so handsome!" she added.

She had him stand as she kneeled in front of him while slowly lowering his boxer briefs, "And are you still dating her, and if so, do you have sexual relations?"

A tuft of pubic hair appeared.

"We broke up. As I said before, we never had sex."

"I see," said Amanda.

The base of his penis showed, and it just kept going and going as she pulled down his briefs.

"Did you get naked together? You know, did you explore each other's bodies?"

He nodded slightly.

His cock hung down flaccid, but it was still long and thick. It looked ... heavy.

"Did she touch you and did you touch her? What did you touch?"

"I uhh, I dunno. I guess I touched her chest but when she touched me, that was the problem."

"What was the problem?" asked Amada as she stared at his length.

"She said that I was freak ... down there."

"Oh no. She shouldn't have said that. That's not right. Let me see what you have and give you a professional opinion. Would that be good?"

He nodded and she gently pulled his boxers to the floor.

Indeed, Kyle's cock was large, even for a young man his height. The amazing part was his cockhead was like a medium plump plum just hanging at the end of it. It was oddly... a deep purple.

She went back to her tablet and referenced it as if reading and taking notes. She hopped up onto the edge of her desk letting her breasts purposefully bounce. "Do you masturbate? If so, how frequently?"

"I uh, I don't know. Sometimes. It's hard ... er ... I mean, it's difficult to ... it gets hard sometimes, and I need umm, relief ... y'know?"

She smiled sweetly and bent more at the hip, "I do. This might surprise you but even women need ... relief."

"They do?" he asked sincerely.

"Yes Kyle, they do. I see you are getting hard now."

Kyle immediately tried to cover up.

"Oh no, Kyle! It's all right. It's natural for a young man like yourself to get hard multiple times a day. Perfectly natural. Plus, it helps with my examination. Don't hide it. Let me do my job!" She smiled and he relaxed a bit removing his hands.

"Now Kyle, what gets you hard at home?" she asked simply.

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"My mom. Oh shit, I shouldn't have said that! Fuck! Oh, I'm sorry! I shouldn't have said that either! I'm so dumb. I just shouldn't talk. I'm always saying the wrong things!"

As she closed the distance, Kyle's eyes went wide as her heavy breasts bounced again. She put a hand on his shoulder, "It's alright. It's alright. Believe me, I've heard worse things in this very office. Don't you worry at all."

Discreetly, she undid another button while adding, "Many young men are attracted to their mothers. A prominent psychiatrist, Sigmund Fred, developed an entire practice around it. It's perfectly normal for a young man to be attracted to his mother, especially at your age. Perfectly normal."

She undid another button. Her bra would show but that would be okay. Lot's of women's bras show.

"I need to examine you now," and she gripped his shaft gently, each finger gripping the middle. There were a few inches on either side of her grip and then that plum of a head, too.

She turned it left and then right. It was sizable and not completely hard yet, "Kyle, as far as your mother is concerned... she IS an attractive woman. Anyone would look at her and get excited. You do find her attractive, right?"

"Oh yes, but that's not right, right? I mean, isn't that wrong?"

She smiled at him again. He was a nice young man. "Kyle, let's you and I deal with the physical for now. After that, we'll talk about emotional, psychological, and what's morally right and wrong. How's that sound?"

"Sure. That's a nice way to break it out."

"These gloves are in my way, do you mind if I take them off? And would you mind if I helped you achieve an erection?"

"Umm no, I mean yes, I mean no."

Amanda laughed and he laughed with her. She stood, gave him a quick hug and purposefully pressed her breast into his bicep. He stiffened his back a bit at the soft pressure from her tit.

"Let's see," she said and then paused while lifting his cock again, "tell me about your mother. What attributes do you like? Describe them to me, in detail please."

He hesitated but then started talking as she began to gently stroke his cock. It felt so good to have someone else's hand on him. "Well, she's beautiful. She has stunning hair and skin. Her skin is so smooth and soft."

Amanda noticed his arousal increase as he talked, "Kyle, don't hold out on me. Is that what you think about when you masturbate? Her soft skin? Have you seen her naked? Tell me the truth, please. This is a no judgement zone."

She put lubrication on her hands and squeezed him harder. He gasped at the sensation. He liked it.

"Well?" she asked. "Close your eyes and give me the details Kyle."

Kyle closed his eyes, "Her breasts are stunning. I've seen them. I snuck in on her when she was taking a shower once. They seem large, like for a woman who weighs more. I looked at her bra, it said 36D, and I think that's good. Isn't it?"

Amanda was distracted. Kyle's cock was the biggest cock she'd ever seen. Her pussy was already sopping wet. Some fluid had just escaped her panties and dribbled down her leg. As she slowly stroked him up and down, her big tits bounced too. This was not lost on Kyle. Somehow, his cock extended a little bit more.

"Yes, that's very good. I myself am a, well I'm a little bigger but I'm a bigger woman, too." She was breathing a little harder, now.

Amanda reluctantly let go of his cock and stepped back. She tried to calm herself with a deep breath and wondered what the fuck she was doing jacking off her old friend's son? But now he was so rock hard... and it was a beautiful cock just bobbing up and down in front of her. Plus, she needed to get him to open up more, more about this experience with the girl and more about Greta. Maybe she could just get him to talk more while she beat him off.

She crossed the line, "I think we should make sure that you can ejaculate properly. I uhh, I don't want to get it on my shirt. Do you mind if I take it off?"

Kyle's eyes went wide, "No," he croaked out an answer.

"Would you like to see my breasts? Would that help you? Let's call it a reward for being honest in our first meeting. I might even let you touch them. See, good things happen when you open up!" She smiled broadly at him.

He smiled back reflexively and nodded.

She unbuttoned the rest of her buttons and took off her blouse, smiled, and then reached back behind and unfastened her bra.

He smiled and then hid his smile by trying to look away ... but still looking.

She held the bra onto her breasts for a moment or two as just a little tease. And then she let it fall to the floor and kicked it to the side as she stepped closer to him.

"Don't look away. It's okay in here, where we are private. As I said before, I won't say anything and as a gentleman, you shouldn't either. Just between you and me."

He nodded quickly.

"Now, to help you orgasm, could you rub them for me? They always feel so compressed when they're in my bra. It feels nice if you rub them when they first come out ... please?"

She wasn't really asking and didn't need to. He reached out and hefted them in his large palms. Her breasts were indeed big and full and spilt out of his big hands as he massaged them. Her nipples were small, pointed, and hard. She reached behind his head and guided him down to them. He greedily sucked her nipples alternating from one to another.

She was so horny. She knew this was the wrong thing to do. This was farther than she'd ever gone with any patient, and this was only his first visit. What was it about him? There was something about him, perhaps his vulnerability. She wanted him to build confidence. True, she also wanted to feel that meat inside her. She stroked it as he was completely distracted by her tits.

"Okay Kyle, let's just calm down a little bit, just a little bit."

He looked sad, like a boy whose toy got taken away.

She smiled adding, "I don't want you to orgasm too quickly, dear. We want the best experience for you." Kneeling down in front of him again, she pretended to examine his cock but instead, snaked out her tongue and licked him quickly and efficiently.

He gasped and his cock throbbed in her hand. She wrapped her other hand around the base squeezing tightly. His cock continued to throb as she tightened her grip.

Breathlessly, she added with a giggle, "Don't cum yet. Don't cum yet!" She paused, smiled knowingly, "Have you smelled your mother's underwear? Tell me the truth, Kyle!"

He began with a denial, but she shook her head interrupting him, "Tell the truth and I'll lick you again! Don't and you'll have to take care of this ... yourself!"

She knew it was an empty threat as soon as she said it. She could barely wait to feel his warm cum on her chest.

He was a little calmer now and she started stroking him again, one hand on top of the other from base to head.

"Okay, I stole her panties once," he started and she stopped stroking, "alright! Fuck this feels so good!"

She smiled, "Tell me everything and then I will finish you off. Would you like that?"

He nodded breathing hard, "Everything ... oh geez. I'm kind of embarrassed. I uhh, that feels sooo fucking good! Yes, everything. I take her panties out of the laundry two to three times a week and I uhhh, yeah I like that, I smell one pair and I wrap another around my cock and beat off with it. That's everything. I swear!"

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