Helping My Best Friend Ch 01

All characters depicted in the story are 18 years of age or older.

*****

I feel bad for my best friend Carson. We both just graduated high school and we wanted to enjoy our last Summer before college. Especially since he's going to a different city for college while I'm going to our local college.

Instead, Carson was forced to take summer classes right after graduating high school. Carson Mother, Debra Mitchell, told him that just because school was over doesn't mean he shouldn't study. I knew how controlling Carson mom was during high school, but I thought she would at least chill out after high school.

As Carson's best friend, it's my responsibility to help him. That's why I spent a whole month learning hypnosis. At first, I was hoping to help make Debra more relaxed, but I found out that I'm actually talented in hypnosis! I even hypnotized multiple people and had them obeying my commands. I'm going to make Debra Mitchell be the caring mother her son deserves. Hehehe.

****

"Thank you so much for inviting me inside Debra. I can't believe I left my charger here," I said as I followed Debra to the living room. Once we were in the middle of the room, she turned around.

"Randal. Please call me Mrs.Mitchell," Debra said in mild annoyance. "You know where Carson's room is. Hurry up and grab what you're looking for." She went back to sitting on the couch and continued watching her soap opera. She didn't even wait for me to answer. What a bitch.

"Thank you Mrs.Mitchell!" Trying my best to convey gratitude to the controlling woman. I went inside Carson's room and pretended to search his desk. I didn't forget my charger here, I just needed an excuse to be invited inside.

I purposely came over when I knew Carson would be at his summer classes and Debra would be alone. And her husband, well, Carson told me that his dad gets home late in the summer.

I checked my pocket to make sure I still have the necklace stowed inside. When I felt the necklace in my pocket, I pictured Debra and how she would look hypnotized. Carson Mom had an amazing hourglass figure with big round tits. She kept her hair shoulder length and dressed conservative. But even through the ugly clothes, I could tell she has a sexy body.

"Let's get started," I whispered. Ready to start my plan, I started walking back to the living room.

"Did you find your charger Randall?" Debra yelled. Her eyes were still glued on the tv.

"Yup! I'm lucky it was still here."

"That's great. Listen, can you lock the door when you leave Randy? Thanks," Debra said. Wow! She must really want me gone already.

Instead of leaving when Debra told me, I slowly walked in front of her. Blocking her view from the tv. She paused her soap opera and crossed her arm.

"Do you need something? I really just want to watch my show kid" Debra angrily said.

"It's my Ma birthday soon. And I really wanted your opinion about the gift I got her," trying my best to look innocent and harmless.

"Not right now Randal. I'm busy. Please move so I can get back to my show."

"Please! It'll be quick!" I pleaded to Debra.

"Fine!" Debra grunted in agreement. "What gift did you get for your mom?"

I pulled the necklace from my pocket and held it in front of her. forcing her eyes to look up at it. "I'm planning to give her this necklace for her birthday."

Debra gave a quick glance at the necklace. "It's fine. I'm sure your mother would love it. Now, I have to get back-"

"Please Mrs.Mitchell," I cut her off. "I really want her to like it. Can you please focus on the necklace? I would appreciate your honest opinion." Debra looked mad at being cut off. I expected her to yell at me. Instead, she took a deep breath and focused on the necklace.

"It's pretty," She says. "I like it." Her answer was dry, but at least she finally focused on the pendant.

"Thank you for listening and focusing on the necklace," I said smiling. "Don't you think the red jewel is pretty. I picked it because it would look good with my Mom's green eyes. Not only that, it's so eye-catching. I can just keep staring at it. Focusing on it."

Debra stared at the red jewel in the middle of the necklace. It was small, so she moved closer to inspect it. If Debra was wearing a blouse instead of a shirt, I would be able to see her big tits.

"It's nice. Not too extravagant. Is the jewel real Randal?" Debra muttered. Her eyes concentrated on the jewel.

"Look closely and tell me what do you think Mrs.Mitchell." I said. I started to gently swing the necklace. "Focus on the jewel. Notice how the light shines off the gem as it swings back and forth."

Debra obeyed and was following the necklace. Trying her best to see if the jewel is real or not. I smiled when I noticed how focused she was.

"When I count down from three, tell me your answer. 3...2...1!" and snapped my finger. Debra immediately straightened from where she was sitting.

"Real!" Debra shouted.

"Good job Mrs.Miller," I said and Mrs.Miller smiled at my compliment. "You are so good at listening and focusing."

"Thank you," Debra said with a tint of red on her cheeks.

"Now, when I count down from 3. You will close your eyes and sleep," I quickly said to her.

"What?"

"3...2...1!" I shouted and snapped my finger again.

Debra's eyes closed as her body relaxed and her head slumped back on the couch. I feel a rush of excitement seeing how I just hypnotized my best friend mom.

"I'm going to count down from 20 and with each number you'll feel your mind get relaxed and empty. 20...19..." I wanted her to fall deeper under my control.

"15...14...Feeling relaxed," As I counted down each number, Debra was leaning more and more on the couch as she lost strength in her body.

"8...7...6." She was slowly sliding down from the couch as she heard the numbers. "5,4,3,2,1. Feeling totally relaxed and empty." I gently move Debra so her whole body is laying on the couch.

I stare at my best friend Mom as she lay there, vulnerable and open to my suggestions. She's in her late 30s, but still keeps her body healthy. It's a shame she likes to dress conservative. She would be a total milf if she dressed a bit sexier.

I crouched next to her and whispered, "I'm going to count down from 100. With each number, a feeling of trust for me will grow more and more inside you." And started counting.

I could have started at a lower number, but I really needed Debra to totally trust me. And with how rude she was with me, being her son's friend was not enough.

"Do you trust me? Mrs.Miller?" I asked her after I finished counting.

"Yes," She replied with a slight smile.

"It's fine if I call you Debra. In fact, you feel a nice tingling feeling when I call you by your first name," I said.

"Okay...call me Debra."

"Debra," She smiled when I called her name, "I want to ask you a few things and you'll answer them honestly. Do you understand?"

"I understand," she replied softly.

"Why do you force Carson to study and take so many classes?" I asked her.

"It's good for him...good for his future."

"Do you feel like a good mother? Getting him ready for his future?"

"Yes." Debra smiled. Parents have different parenting styles. My parents are super chill as long as I don't get in trouble. Debra was a strict parent with an authoritative method. I'm going to help Carson and Debra have a loving relationship before summer ends.

"Is Carson happy? Do you think your son is happy with so many classes? Spending countless hours studying. Doing everything he can to make YOU happy" I said in a commanding tone.

"I...I think-" Her brow furrowed in unease.

"He's not Debra. Carson is unhappy and stressed. You put a lot of pressure on your son and he's working so hard to make you proud."

"But it's for his future," she tried to reason.

"Don't you care if your son is happy? Do you want him to be miserable?"

"No, I-I."

"You're a bad mother Debra. Say it!"

"I'm a bad mother."

"Repeat it! And each time you say it, you'll feel more and more guilty."

"I'm a bad mother," I heard Debra repeat again and again.

I let Debra repeat she's a bad mother for a while. I saw her expression changed from confusion to sadness. Even though her eyes were closed, she had tears running down them.

"I-I'm a-a bad Mo-mother," Debra was hyperventilating the phrase now.

"Stop. You're a selfish mother. Never asing your son if he was happy at all."

"Wa...I'm a selfish mother." Debra lightly wailed.

Now that she believes she's a terrible mother and feels guilty. I'll throw her thread of hope she can latch on.

"You want to be a good mother don't you? To make up for all those years of selfish parenting. You want to make your son happy."

"Yes! I want him to be happy."

"You need him to be happy to make up for all the classes and studying. You need Carson to be happy."

"I need him...to be happy."

"I can help you."

"You?" Debra replied softly.

"I'm his best friend...So I know exactly what you can do to make Carson happy. But you have to obey everything I say Debra."

"Yes. I'll obey! Please help me," She smiled at the idea of being helped by her son best friend.

"Good Debra, when I count down from 3, you wake up. Remembering that you're a bad mother and only I can help you. 3...2..1 wake up." I said and Debra immediately woke up.

****

"Wow! This hamburger is really good Debra!" I said as I was eating a hamburger.

"Thank you Randal. I'm glad you liked it. I was worried since it was last minute," Debra happily said. She's been watching me eat the hamburger the whole time. Worried if I would like her cooking.

After Debra woke up, she begged me to help her get along with her son. That she wants Carson to be happy. Seeing how I'm her son's best friend, she was genuinely asking me for advice. So I told her if she can make me something to eat first and she quickly agreed.

"Randal...Can you please help me get along with Carson. You're his best friend. Should I buy him a new game? Go on a trip with him?" Debra said.

"Get me something to drink," I ordered Debra. She immediately went to the fridge and got me a bottle of water. I ordered her to open it and she obeyed. Good, she's obeying me like I told her to. Now for the real test.

"Take off your clothes Debra."

Debra said yes and quickly took off her clothes. Once she was naked, she sat on the chair across from me and waited for me to continue. My best friend's mom is naked in the kitchen while I'm eating and staring at her. Debra would really do anything to make her son happy.

"First, tell him he doesn't have to take classes anymore. Carson would be happy having more free time in the summer," I said, taking a sip of water.

"You're right! Carson should enjoy his last summer," She happily agreed.

"Second, Carson been pretty stressed right? Spending countless hours studying."

"Yes," Debra sadly agreed with me.

"So, what you have to do Debra is give your son a nice massage. To help relieve his stress. Trust me, I'm his best friend." I took one last bite of the hamburger. "And I'll be happy to teach you."

"Thank you Randal! I'm glad I asked you."

I stood up from the table. "Lets go to your room," I said to Debra. "It'll be better for me to teach you there." Debra agreed and led me to her bedroom. My eyes glued on her naked ass the whole time.

****

"Are you sure Randal?" Debra looked at me confused. "Will my son be happy if I help him masturbate?" I had Debra kneel in her own room while I was comfortably sitting on the edge of her bed.

"Of course Debra. Carson has been stressed lately. If you help him masturbate you help relieve some of his stress. I know he'll be happy having his beautiful Mother help him," I said with a sly smile. Looking down at Debra's naked body.

"I-I'll do it," Debra said. Looking ready to do anything to help Carson.

"That's great Debra, I'll do my best to teach you," I pulled my pants off. "But you have to trust me."

Debra's eyes widened when she saw my hard cock. She looked like she was having second thoughts, but then she looked back at me. And nodded yes.

"Good. Why don't you start with using your hands and make me cum." I commanded.

Debra slowly reached for my cock and gently held it in her soft hands. She moved her hands up and down along my cock. It feels nice, but her hands had a clumsy rhythm to them.

"You don't do this much for your husband huh?" I asked her.

"Sorry no. I never used my hands like this." Debra looked sad. "Is it bad?"

"It's not bad, but it won't make me cum." Debra looked worried. "Don't worry. As my best friend's mother, I'll make sure to teach you."

"Thank you so much Randal!" Debra said with relief in her voice.

****

"Ah...that feels good Debra," I screamed.

"Really! I'm so happy baby. I want you to feel good. Feel good for mommy." Debra affectionately said.

For the past hour, I taught Debra how she should stroke my cock. That it's important to start with teasing. Using her tender fingers to gently move around my cock feels. Then after a while of teasing, to softly hold my cock in one hand.

"Randal baby. Do mommy hands feel good? All mommy wants to do is make your cock feel good!" Debra cooed.

I even taught Debra what words she can use to help make me cum faster. Mostly words you hear in mommy play porn. She was a hot milf and Debra was a quick learner.

"My baby's cock is so big and hard. Mommy so happy!" Debra moaned. I didn't teach her to say that.

Then, Debra slowly stood up and leaned her head next to mine. I could hear her warm breath in my ear.

"Cum for mommy baby. Mommy wants to see you cum so hard," she whispered next to my ear.

"Okay Mommy," I muttered. Feeling so good, I lost myself in the roleplay.

"Please cum for mommy. Mommy wants to know she's doing a good job," Her words softly reverberated in my ear. I don't know where she saw this, but I'm glad she did.

"*slurp* Mmmh," I heard Debra tongue twisting around inside my ear.

I was close to cumming. But her tongue in my ear pushed me over the edge.

"I'm cumming Mommy!" I yelled.

"Yes! Yes! Cum for mommy! Cum all over mommy hands." I shot my cum on her hand. When I was done cumming, she slowly licked my cum from her hand. "Mmh! My baby's cum taste so good!"

Seeing my best friend Mom happily eat my cum was so hot. Who knew Debra had a talent in mommy play. Carson oedipus complex will definitely love it.

"How'd I do Randal?" Debra asked. "You think I learn enough to make Carson happy?"

I can teach Debra more, I mean, I'll be happy to teach her more. Who wouldn't want to teach a sexy milf. But what if Carson doesn't accept her Mother's stress relief and she doesn't use her newly discovered talent.

I looked down at Debra who's kneeling patiently. Remembering her saying "mommy" and "baby" a while ago, I could feel my cock hardened again. I decided there's still a few things I would love to teach Debra. I'll hate to do this to my best friend, but I can always hypnotize him if he doesn't like it.

"Debra, I think there's still a few things you can learn," I said.

****

Debra P.O.V

I'm standing in front of my son's bedroom, ready to finally make Carson happy. I take a moment to remember everything Randal taught me today.

"Carson, are you busy? Can I come in?" I knocked on his door.

"No Mother. Come in, the door's open," I heard his voice through the door.

I opened the door and saw Carson was sitting at his desk with his chair turned towards me. My heart ached as I saw the countless books and papers scattered behind him. How did I not notice how hard my son worked?

"MOM! What are you wearing!" My son yelled at me. I was only wearing a blouse with my panties. Randal told me it was the best I can do since I don't own any sexy clothes.

I didn't say anything to my sweet son. My son was quiet as I slowly walked towards him. When I was close, I dropped to my knees and put my head on his lap. "I'm sorry," I yelled.

"What are you doing mom!"

"I'm sorry for making you take so many classes growing up Carson. You can stop if you want." I slowly pulled my head from his lap and stared at him. "It's your last summer before college, so I want you to enjoy it."

"Mom..." My son looked straight at me.

"I'm sorry I was so strict with you growing up. I just thought it was best for you. But I never asked if you were happy." Starting to feel tears in my eyes. "I was a bad mother to you. Can you ever forgive your selfish mother?"

I was nervous because my son didn't say anything right away. The only thing that I was focused on was on my beautiful son's worried face. Please forgive me Carson.

"It's okay mom. I know you did what was right," Carson finally said.

"Thank you thank you!" I yelled in delight. I put my arms around my son who's still sitting.

"Please Mom. Let go," I did as my son said. "What's with you today?"

"I just want to make up for all those years I was a bad mother" I started to rub his cock through his shorts. "Please. Let Mommy make you feel good, baby. Mommy will do everything."

My son was still speechless as I pulled his shorts down. With my son cock inches away from me, I finally get to be a good mother.

****

Randal P.O.V

I got a message from Debra the next day, thanking me for everything I taught her. I messaged her back asking how it went. And she replied that everything went fine and that Carson was happy for what she did. Debra even told me that she planned to help her son every night.

"I'm glad Carson will have fun with his mother before he leaves for college," I said.

"What was that Randal?" Mrs.Tass, my former highschool science teacher, said. She was on her knees giving me a blowjob.

"Just thinking about this text Mrs.Tass."

"Randal! I'm giving you a private lesson. Please put away your phone before I confiscate it," Mrs.Tass said while jerking me off.

"Sorry. It won't happen again," I smiled.

"Hmph!" Mrs.Tass huffed and she went back to sucking my cock. I wonder if I should share my hypnotized teacher with Carson. Maybe when he comes back home for his semester break. For now, I'll enjoy Mrs.Tass and both of us can enjoy his mother.