The Stepmother Checkup Ch. 01

Chapter 1

"Sure, Babe. I'm gonna miss you!"

"Me too, Peter! See you Monday, then. Gotta go now!"

"Bye Macy!"

Peter hung up. His girlfriend had just told him she was away with her father for the weekend. They had been together for about three weeks now, after meeting at a party.

About an hour later, Peter's phone rang, he didn't know the caller's number. He picked up the phone :

"Hello?"

"Hello, Peter, it's Dana, Macy's mother."

"Oh, hello Mrs Weathers. How are you?"

"I'm fine, Peter, thanks. Actually, I was calling you because I wanted to talk to you. Could you come at my place if you don't have anything planned?"

"Um, sure Mrs Weathers. Macy just told me she was going on a trip with her dad, so I'm free. There's nothing wrong, is there?"

"Don't worry, Peter, I just want to talk. Can you come now if it's okay with you?"

"I'll be on my way, Mrs Weathers."

Twenty minutes later, Dana's doorbell rang. She opened the door to her daughter's boyfriend. She looked at the muscular, nicely tanned 20 year old young man. As always, she thought, her daughter had good tastes in men. She welcomed the young man in. and led him to the living room, where he sat on the sofa.

She quickly joined him, bringing with her two cups of coffee, which she placed on the glass coffee table.

"So, Peter, since you've started seeing my daughter, I haven't had much time to talk with you. I wanted to know more about you."

"Sure, Mrs Weathers... Well, I'm going to start engineering studies next year, I like sports and electro music..."

"Interesting. But Macy already told me all that. I wanted to know you on a more... personal level. For example, what are your long term goals in life? What kind of relationships are you currently looking for?"

"Those are hard questions, Mrs Weathers... Regarding my future job, I'm not sure yet, I wouldn't mind working abroad... As for your question about my relationships, are you trying to know if it's serious between Macy and me?"

"I'd like to know how you consider your relationship with her, yes."

"Well, you know, Mrs Weathers, we've only known each other for three weeks, so it's hard to say. But we have a lot in common and our personalities seem to be a good match."

"That's good to hear." She smiled. "Have you had many girlfriends before?"

Peter hesitated a moment. He had never stayed very long with one girl, and sometimes even dated several at the same time.

"I've had... a few. Usually not for very long, though."

"I see. I hope you're not embarrassed with all these questions, Peter. I don't want to make you uncomfortable..."

"No, that's okay, Mrs Weathers. I understand you want to know more about the people close to your daughter, and that's fine by me. You want to make sure she dates good people."

"Exactly, I'm glad you understand. Now, I'm sorry if this seems a bit blunt, but... I've heard you and Macy when you were locked in her bedroom yesterday. I know you two had sex."

The young man blushed.

"I, um, I'm sorry, Mrs Weathers, what do you..."

"That's okay, Peter, I'm not mad or anything. You're both young adults, there isn't anything wrong about this. But, as you said yourself, I want to make sure you're good enough for my daughter... in every way."

The young man was startled.

"Wh-what do you mean, exactly?"

"I want to know that you're a good lover, that you treat her well. I've had my share of experiences, when I was her age, and not all of them were good. I'd like Macy to avoid bad experiences."

"I... I see. Did she tell you something? About me, I mean?"

Peter wasn't sure where his girlfriend's mother was going with this.

"No, don't worry, Peter. I just want to check things myself. You're the first boy she's had sex with, right?"

"Yes..."

"Then its all the more important that I take my precautions. Have you had sex with other girls before?"

"Yes, Mrs Weathers..."

Dana moved and sat right next to Peter. Turning her bust to face him, she said :

"Okay. Now, as I'm sure you'll understand, I'd like to check out your body."

Peter almost dropped his coffee cup as his heat skipped a beat.

"I'm sorry?"

"I want to know who my girl is having her first sexual experiences with. I want to see your body."

He didn't know what to say :

"Mrs Weathers, I... I'm not sure this is a good idea, I mean..."

"Come on, Peter, you don't have to worry. There's nothing wrong with your body, is there?"

"I don't think so..."

She ran her fingers through Peter's hair, looking in his eyes.

"Then don't be ashamed to show it to me. I don't think you have any reluctance to show it to my daughter, do you?"

"I, um... don't, Mrs Weathers..." He paused to think for a few seconds. The physical contact was making him nervous, but also starting to arouse him. He finally asked : "So, what do you want me to do exactly?"

"First, I want you to strip naked."

"Okay..."

Hesitantly, the young man stood up. He put the cup on the coffee table, and looked around, as if he expected someone to walk by at that exact moment.

"Don't worry, we're all alone in here, Peter," Dana said.

Peter slowly pulled up his tee shirt, revealing his well formed pecs and abs to Dana. Then he kicked away his shoes, pulled his socks, unbuttoned his jeans, and pulled them down. He was now standing in his underwear.

"Pull these down too, please."

Shyly, he slid down his underwear, revealing his sex to his girlfriend's mother. Dana's eyebrows raised a little, she was pleasantly surprised to see he was shaven.

"Well, you seem to have nothing to be ashamed of, Peter. I wonder what your penis looks like when it's fully erect. Please, show me."

"How do you want me to..."

"I'm sure you can think of some way," she interrupted him, sporting a playful smile.

"Yes, Mrs Weathers..."

It was too late to turn back. His face scarlet, the young man slowly brought his right hand to his manhood. He couldn't believe what he was about to do. He had never touched himself in front of someone, and now he was going to do it in front of his girlfriend's mother.

He wrapped his fingers around his sex, and began pumping slowly. Dana watched with attention as his manly organ quickly sprang to life. Peter felt his heartbeat accelerating as his penis grew harder beneath his fingers. He shyly looked at his girlfriend's mother, who was focused on his penis. When it reached it's full size, he removed his hand. His penis was now facing up, pointing directly towards Dana. It throbbed slightly with every heartbeat.

Peter realized his embarrassment was fading away, replaced by his growing arousal.

"You have a very fine penis, Peter. Macy is luckier than I was at her age," she added with a smile.

Peter replied with a shy, muffled laugh.

Dana, still sitting on the sofa, leaned forward, bringing her face closer the the young man's erection. She delicately grabbed it between her right thumb and index. Peter twitched when she made contact, but didn't say anything.

Dana moved Peter's penis left, right, and up, examining it from all angles with lust in her eyes. Carefully, she pulled down the foreskin, revealing Peter's hard glans. She could feel the young man's heartbeat beneath her fingers. She released the hard penis and watched it throb before her eyes.

"You're already pretty turned on, aren't you, Peter?

"Um, y-yes..."

"Now, I want to know if you can hold long enough to give my daughter real pleasure. Some men just think about themselves, and come within a few minutes. I want to see how long it takes you to come."

This was going way too far, but the young man was now pretty sure he wasn't going to regret going through with it. Actually, he really enjoyed being naked in front of the beautiful, mature woman. He asked in a low voice :

"Do you want me to... masturbate?"

Dana smiled and replied :

"That would be cheating, young man. Let me handle this. First, you're going to stand on your knees, right before the coffee table."

"Why there?"

"You'll find out soon enough. Just do as I ask."

Peter moved to the coffee table. As he put his knees on the carpet, he saw his erect penis stood only a few inches above the large, dark tinted glass panel. Dana removed the two coffee cups from the table, then placed herself behind her naked guest.

She also put her knees down, and pressed herself against the Peter's back. He felt the fabric of her clothes against his body. He smiled as her generous breasts squeezed against his back.

"We'll see how sensitive you are, now. I will masturbate you. At my own rhythm."

Dana's hot breath caressed Peter's ear as her lecherous words escaped her mouth. With her right hand, she cupped his balls and applied a soft pressure, delicately squeezing one after the other. Peter let out a soft moan, and looked down at the feminine fingers feeling his balls.

After a while, she switched hands, and used her right hand to wrap her fingers around his throbbing shaft. Peter felt her firm grip. Still playing with his balls, she began to slowly pump him. Peter didn't move or talk, he was completely submitting. She said :

"You seem a little tense."

"Yes, sorry..."

"Don't be. Maybe you'd feel less ill at ease if we talked about something while I masturbate you?"

"Um, I don't know, Mrs Weathers, if you like..."

"Um, let's see... Macy told me you're a bit of a musician. What is it you play exactly?"

It was strange and disturbing to hear her ask him such a casual question while she touched him so intimately. It was very difficult for Peter to focus on anything, with his girlfriend's mother handling his sex. He looked down at her hand sliding up and down his glistening shaft, and tried to concentrate on the question.

"Um, I... don't exactly play an instrument. I'm a DJ. I use controllers to mix various songs together..."

He was having trouble speaking, as Dana's stimulation wa starting to draw moans from him. Dana asked :

"I see. Do you do that on stage?"

"I have on a few occasions... I mainly practice at home."

"Actually, if I recall correctly, Macy told me that you two met at a party where you performed?"

Peter was breathing deeper and deeper with every stroke of his penis. He once again looked down at Dana's hands playing with his sex as he answered :

"Th-that's right... We, um, talked after I finished my performance..."

Dana nodded, and progressively raised the speed of her movement. Soon, Peter's breathing became faster and increasingly erratic, and he closed his eyes.

"You're doing pretty good, Peter, you think you can hold it a while longer?"

"I-I don't know, Mrs Weathers..."

She slowed her movement back to its initial pace. Her hand was covered in the young man's precum, easing her sliding movements up and down the sensitive member. She kept going for a while. Once she felt the tension rising again, she released her grip on the young man's erection, and removed her left hand from his scrotum. Peter opened his eyes and looked down. For a few seconds, they both silently looked at the hard member, throbbing with anticipation. Dana smiled as she saw yet another drop of precum appear at the tip of Peter's penis.

After a while, she finally grabbed it again, and placed her left hand back on his balls. Her skillful stimulation was driving Peter crazy and bringing him ever closer to the edge, and Dana knew it. She could tell he wold soon come. She said :

"You've been holding it long enough, Peter, that's pretty good."

"Th-thank you, Mrs Weathers..."

"When you come, you will ejaculate on the coffee table. The glass panel will give me a perfect view of the semen you produce. Alright?"

"Y-yes, Mrs Weathers..."

"And you will warn me before you reach orgasm."

"Yes..."

The young man was subjugated by his girlfriend's mother. He was completely under her control. Dana used the tip of her index to rub the underside of Peter's glans as she kept pumping him. She resumed their little conversation :

"So, Peter, tell me more about when you met my daughter."

"Well, I, um... Like I told you, we talked when I had finished mixing on stage. She came to me, she was... beautiful... And we started talking."

"Aha. What did you talk about?"

The young man now had to make a tremendous effort to be able to keep this casual conversation, as he was getting so close to his orgasm. He took a deep breath and answered :

"She started by telling me she liked my playlist... the... songs I had chosen to play. Then I went on asking her about her tastes in... music..."

"Macy told me that the second time you met, you..."

Peter interrupted her :

"I'm sorry Mrs Weathers, but... I'm... going to come..."

At the young man's surprise, she removed her hands altogether, and watched from over Peter's shoulder as he began ejaculating. Free from her grip, the hard member began throbbing erratically as it shot white ropes of semen across the glass table. The young man began to growl in frustration from the interrupted stimulation, and Dana quickly grabbed his wrists to hold him in place. His thick orgasmic fluid kept erupting from his twitching sex, one burst after the other.

"That's good, Peter. Keep going, release all your load on the table."

Dana looked at the glass panel, covered with an increasing number of white lines diverging from Peter's sex. When he stopped ejaculating, Dana felt his body was still tense, and that his orgasm wasn't over. She let go of his wrists and grabbed his penis again. As soon as she resumed pumping it, the young man started moaning and rocking his pelvis against her hand. His orgasmic pleasure was finally spreading throughout his body, thanks to Dana's stimulation.

She saw he was about to fall forward and helped him stay up by pressing her left hand against his chest. She smiled as she saw that the young man still had more semen to give her, and felt his whole body tremble against her as he continued his ejaculation.

When she saw he was done for good, she increased her grip on his shaft to squeeze the last drops of manly fluid. Peter looked down at the thin, feminine fingers covered in his fluids, pinching him and drawing out all of his semen. Peter's orgasm finally ended in a long sigh of release. Her left hand still on his chest, Dana pressed the young man's body against hers, caressing his sex as the last waves of pleasure coursed through his extremities.

"Well, I'm quite satisfied with what you've shown me so far, Peter," she said as she let go of him and rose up.

"Um, thanks, Mrs Weathers."

Dana walked towards a box of tissue across the room, and grabbed several of them. Peter looked at her right hand, covered in his white goo. As she wiped her fingers, she moved toward the kitchen and pulled a cleaning product from a drawer. She walked back to the living room and to the coffee table. Looking at it with a smiling nod, she said :

"That was a pretty impressive ejaculation, Peter."

"Th-thank you, Mrs Weathers."

"Now, please be a lamb and clean it up for me," she asked, putting down the cleaning product and the remaining unused tissues."

"Yes, Mrs Weathers."

Standing on his knees, naked before the dressed woman standing above him and having to clean his own sperm from her coffee table, Peter felt belittled. Obediently, he grabbed the cleaning product and sprayed it over the surface of the table.

"Thank you very much, Peter."

She just stood next to him with her arms crossed while Peter, still out of breath from his messy orgasm, wiped the glass panel clean of his semen. When he was done, she asked :

"So, Peter, did you enjoy this?"

She looked down on him in a judgmental fashion. The young man gulped, at a loss for words :

"Mrs Weathers, I..."

"Just be honest. Macy won't know. Did you enjoy having your girlfriend's mother masturbate you?"

"Y-yes..."

"Would you like it to happen again?"

He looked up to her. He hadn't had the time to think about it, but suddenly he realized that the reasons she had initially given him were just excuses, and that she really did all this just because she enjoyed it. This made him feel like he had betrayed his girlfriend even more, but this was so good... He actually really enjoyed being her plaything, and admitted :

"Yes, Mrs Weathers."

"Then come back here tomorrow afternoon. You can get dressed, now."

Chapter 2

Dana watched TV while she waited for the doorbell to ring. It was 3pm, she expected her daughter's boyfriend would be here any minute now. She had spent the rest of the previous day thinking about what she wanted to do with him. She wanted to dominate him further. She wanted to make him her sexual plaything. And from what she had seen so far, he wouldn't be very reluctant to submit.

Finally, the doorbell echoed in the house. Dana stood up, turned the TV off and walked to the door. She was wearing a pair of jeans and a white sleeveless top. She unlocked the door and opened it.

"Hi, Peter, how are we doing today?"

"Fine, Mrs Weathers."

"Please, now, come on in."

Like the previous day, she invited him to follow her to the living room, and sit on the sofa. As soon as they both made themselves comfortable, she asked :

"So, Peter, why did you come here today?"

The young man didn't expect the question. They both perfectly knew what had brought him back, given their last conversation. But it seemed she wanted to hear him say it.

"Well, I came because you... invited me."

She frowned slightly.

"Don't give me that, Peter. You came here for one specific reason. And I want you to tell me."

The young man blushed.

"I, um... want you to... well, I want to do what we did yesterday, again."

"And what did we do yesterday?"

He was now becoming scarlet. Dana, on her side, didn't seem to be affected by the conversation she was leading.

"You... I... undressed for you, then... you touched me."

"And you want that to happen again?"

"Yes..."

"Then ask me. Politely."

It took all of his courage to answer.

"Mrs Weathers, I'd like to... undress for you again. And I'd like you to touch me."

"Good. Then undress now."

"Yes, Mrs Weathers."

Peter stood up and began removing his clothes. His lust was slowly taking over his embarrassment, and he slowly gained back his composure as he dropped one garment after the other. Still, he had trouble looking at his host in the eyes. Soon, he stood before her, completely naked.

Dana stood up.

"Follow me," she said, as she turned around and walked out of the living room.

Peter followed her, leaving his clothes behind, as she led him her bedroom. There, he found a large bed, covered with white sheets.

"Are you ready to do anything I tell you, Peter?"

Her tone was calm but somewhat authoritarian. The young man hesitated, but pushed by his lust, he felt compelled to agree :

"Yes."

"Yes who?"

"Yes, Mrs Weathers."

"Good. Now, get on the bed. You will stand on all four, facing away from me, on the edge of the bed."

The young man obeyed timidly, slowly placing himself as requested. He realized that by doing so, he was exposing his dangling sex as well as his anus to his domineering host. His penis wasn't fully erect yet. Dana grabbed a small transparent glass from her bedside table and spoke :

"Now, Peter, I am going to milk you. I will draw out all your sperm and fill this glass with it."

As she spoke, she immediately noticed his member getting harder.

"I can see this idea seems pleasing to you, young man. Tell me, have you ever been milked before?"

"No, Mrs Weathers."

Dana put the glass on the bed, beneath the young man's sex, and opened the bedside table's drawer. She pulled from it a bottle of lubricant. She opened it and began pouring it abundantly above Peter's crotch. She looked as the thick fluid ran down from his lower back, sliding between his buttocks to reach his anus, then continued its journey along Peter's balls and his now fully erect penis. She kept pouring until Peter's crotch was completely covered in lubricant. She grabbed his sex and stroked it a couple of times before releasing it. The young man moaned.