The Tutor

Yay its done! Sorry if it's too similar to the last story but tbh that what I've been in the mood to write recently. Also if there are also any loose ends I apologize for that as well I ran out of time as always! Hope you all enjoy and it was worth the wait! Hopefully my next cap doesn't take as long. 

Michael laughed with his buddies as he sat in Mrs. Burnberry’s Algebra class. The high school senior’s were all supposed to be working on homework, however many of their senioritis was kicking in, especially Michael’s. He sat on his phone playing a lame mobile game with his best friend Kyle. The two had been best friends since middle school. They had a bigger friend group, but they mostly stuck together. Michael was rudely interrupted by his math teacher sticking a piece of paper in his face. “Not a good start to the semester Michael.” She shook her head, Michael turned over the paper revealing a 37% on his test. He tried to laugh it off as his friends were watching, “Oops heh.” He chuckled, but he was secretly kind of scared, his mom had been on his back about his grades lately. She didn’t really understand the concept of senior year was to make memories, but he hoped she would understand.

“Mom come on! You know this is a waste of time!” Michael Lewis groaned at his mom as he stared out the window of the SUV. Michael was not in a happy mood, the high school senior’s mom was making him get tutoring in math. Not only that, but it was his last semester of high school, and he’d already been accepted to college, he couldn’t believe dumb his mom was for making him do this. “Michael John Lewis, it is 2 days a week for an hour, it is not the end of the world. You better not be this rude around Mrs. Earhart.” That only made Michael more angry, he just remembered that his tutor was some creepy woman his mom had heard about on Facebook. Michael had looked at her profile, she looked like the typical annoying stay at home wife, how could she possibly be a good tutor?

Michael soon found himself standing on the doorstep of a perfect looking suburban home. He rang the doorbell and placed his hands in the pockets of his khaki jeans and waited. Finally the door opened, standing on the other side was a gorgeous looking middle age woman. She was wearing a beautiful floral midi dress. “Oh you must be Michael! Come in come in! You can call me Barbara!” She gushed. As Michael walked in an amazing smell immediately hit his nose. “Your mom has told me so much about you!” Michael nervously chuckled, “Yeah heh, I’m looking forward to working with you.” He lied. 

The next hour went by fast, nothing really special happened other than Michael trying hard not to stare at Barbara’s tits. Her house kind of gave him the creeps, she seemed like she was the type of woman all about her family and the perfect house, yet there didn’t seem to be any pictures of her family anywhere. But anyways, the hour went by fast and Michael seemed more ready for his math test than he’d ever been.

The next day at school Michael was rudely awoken by his math teacher Mrs. Burnberry when she handed him his test back with a 48% circled in red at the top. Michael banged his head on the desk as he got the test back, “Fuckkkk dude. My mom is gonna kill me.” He said to Kyle, who was sitting next to him. Kyle shrugged, “Don’t you have a tutor? Blame it on her.” He suggested.

Michael did exactly that, he immediately explained to his mom how Barbara had no clue what she was talking about. His mom was skeptical at first, but Michael was a great liar. He smiled as he got his mom to promise to, “talk to her.” This is great he thought to himself, he wouldn’t take the blame for the crappy math test, and he wouldn’t have to do dumb tutoring anymore. He was actually overjoyed, it was such a win win situation. 

Michael was once again, rudely awakened when his mom herded him into the car and drove him to Barbara’s house. “I talked to her, she assured me she will definitely make sure you are learning what you need to this time.” Michael groaned, his plan backfired, he wouldn’t be surprised if Barbara was a lot nastier to him now. 

This time when Barbara opened the door, she had an even bigger smile on her face. “Ah Michael! It’s great to see you again!” She smiled like a flight attendant at him. Michael decided to come clean, “Listen Barbara… I’m sorry for try to blame my test on…” He got cut off, “Oh honey, don’t worry about it. I understand. But that just means we need to teach you some new things!” Michael chuckled, a little relieved, “Sounds good to me!” He said stepping into the house. 

The next day at school Michael flagged down Kyle, “I got a date with a MILF dude.” Kyle laughed loudly, “No way bro.” He laughed again, “How?! Who is she?” Michael smiled, “She’s my tutor that my mom hired dude.  Her name is Michelle, she’s hot dude, she was definitely showing herself off to me while we were working on my homework. She was really nice at first but then I realized she was flirting. So I said what the hell and asked for her number. We are chillin Friday night.” Kyle laughed again. “Amazing bro, you will totally get to pipe.” Michael smirked, “Yeah why else would she invite me over?” The last tutoring session was a little surreal for Michael. Instead of working on math the entire time Barbara got him to watch some training videos. Michael didn’t know how to describe them, but afterwards he felt so much closer to Barbara. He was glad Barbara felt the same way. 

Michael once again stood on the doorstep of his tutor’s house, this time he dressed a little nicer. He still wore his usual khaki jeans, but this time he chose a sweater his mom had gotten him two years ago that he had never found the time to wear. He didn’t wear much other than a t shirt often. Barbara opened the door wearing a zebra print blouse and a pair of mom jeans. She didn’t look like she was ready for a date. “Michael! I’m feeling a little under the weather today, do you mind if we just hang out here for the night?” Michael didn’t care, he just wanted to dick the middle aged hottie down, “Of course Barbara. I’m sorry you are feeling so bad.” Barbara gave him a warm smile, “I bet you can help me feel a lot better.” She winked. Michael laughed a little uneasily as he walked into the house.

Almost immediately Barbara passed him a glass of water, “Your lips look so chapped hun drink this.” Michael did without thinking anything about it, however almost immediately his body felt numb. Barbara smiled, “You should sit down hun.” Michael did so, almost robotically. “Now, your mom and I had a big discussion about you earlier today. We came to an agreement.” Michael tried to respond, but he couldn’t move his mouth, or a muscle for that matter. “Frankly, your mom has given up on you Michael, and she’s turned you over to me.” Barbara smiled widely. Michael was screaming on the inside. “We are going to get your little useless life turned around, how does that sound buddy?” Michael suddenly felt like he was able to move his mouth, although when he tried to call Barbara a psycho bitch all that came out was, “That sounds great Barbara.” Barb smiled, “Good! Now let’s get to work shall we?”

Kyle pulled his tiny sedan onto Michael’s driveway. He picked up his backpack with his Xbox in it and headed for the front door. The new Call of Duty maps came out today and both friends had nothing to do. It was easily going to be a 12 hour gaming session. Kyle was also really excited to hear about how Michael’s date went. As Kyle walked up to the porch Michael opened the front door with his other hand on his hip. “Kyle! Come in come in!” Kyle was already confused… there was something way off about Michael, but it was hard to put his finger on it. “Wow I love that shirt's color.” Michael said, referring to Kyle’s red t-shirt. “Uh Thanks.” Kyle said, weirded out. Michael never really complimented him on anything, much less what he wore. Kyle glanced Michael over as they walked to his room, the way he walked gently on his toes and swayed his hips was definitely new, but Michael seemed… almost smaller, he was never that big but he was a linebacker on the varsity football team, he was considered “overweight”. But his movements seemed livelier, when they got to his room it was spotless, the place was usually filled with Doritos bags and soda cans, Kyle found himself in a lavender smelled cozy bedroom. “Decided to clean up a little since you were coming over! Don't you just love this incense?” Michael rubbed his finger across Kyle’s nose, who shuttered at first, but then took a whiff. Michael let out a little chuckle. “So! I just made cookies! They should be done in a few. We can chat until then, and then I was thinking we could head to the mall… I got some stuff I need to return!” Kyle cut him off, “Dude? I thought we were playing the new Call of Duty maps?” Michael looked at him like he was dumb, “Oh..yeah… I totally forgot about those.” He flipped his now longer brown hair and looked at his phone like he was disappointed. Kyle was bewildered, Michael was usually by far the chillest person to hangout with, he usually didn’t care what they did and went along with whatever. “Uh… I guess we could go to the mall.” Michael looked up from his phone immediately and smiled, “Oh yay! Let me just get ready! Can you watch those cookies for me?” Kyle rolled his eyes.

A week passed, and Michael didn’t get any less weird. Their trip to the mall was one to forget for Kyle. He spent 2 hours watching Michael try on clothes at Macy’s… they were all clothes he’d never envision Michael in either. At school he was disinterested in the usual things they did, but he really seemed to suddenly connect with their teacher Mrs. Burnberry. Michael used to make fun of Mrs. Burnberry for being a complete Karen, but recently Michael would stay after class and chat with her. Michael was also hanging out that Barbara lady more and more as well. Although he insisted it was nothing romantic, he was over at her house almost everyday. Kyle was growing concerned, he even called Michael’s mom. Although he was even more weirded out by that interaction when she insisted Michael has always been quite the wine drinker. Kyle didn’t really know what to do other than go to his dad. Kyle usually kind of avoided his dad, he was a scary guy. He was big and strong for an older guy, his favorite hobby was to work on cars. He was a man’s man and Kyle felt like he had to be extra manly around him. Kyle headed out to the garage where he saw his old man underneath the hood of his old Mustang. “Pops can I talk to you about something.” He said nervously. Kyle went on to explain the situation and how Michael had been acting weird since he’d gone to that woman’s house. His dad agreed something was up, and agreed to help Kyle look into it. They decided to head over to the address the next day.

Mr. Hill made Kyle stay in the car as he went up to the doorstep of the address. Kyle watched as very quickly the door opened, he saw the beautiful blonde woman that Michael had described, he then saw his dad step into the house. Chills were sent down his spine as he had a bad feeling about this. Barbara had invited Mr. Hill in to talk after he voiced his concerns about Michael. “Have you noticed anything off about him recently? My son was saying he’s almost completely different.” Mr Hill coughed briefly. Barbara shook her head, “I’m afraid not, he is as lovely as ever I think. Do you need some water? Your throat must be patched.” She handed Mr. Hill a glass of the lukewarm water which he downed with no hesitation. Almost immediately Mr Hill sat in a perfect posture on the couch, a blank stare on his face. “Oh Mr. Hill, the Michael Lewis I know isn’t your son’s friend. ” Mr Hill nodded his head slowly, “Of course the Michael Lewis I know and you know is that beauty from down the street.” Barb smiled at Mr Hill, “There’s just something about him Mr. Hill… maybe it’s the way he smiles, or tilts his cute little head when he talks, or those wonderful legs… regardless Mr Hill he’s a catch… and I hope you realize that.” Mr Hill nodded his head very robotically again. “He is totally your type Mr. Hill! But I digress, I haven’t noticed anything weird about him. I must get going. I have some errands to run. Thank you for stopping by!” The very suggestive Mr. Hill got off the couch like a zombie and headed for the front door. As Mr Hill climbed into the car Kyle was eagerly waiting, “How’d it go?” Mr. Hill smiled at his son, “Good son, nothing to worry about.” Kyle looked at his dad, there was something weird about him. “Oh... “ Was all Kyle said back. Kyle was afraid. 

Michael lit a candle as he curled up on the couch with a book he was reading called 50 shades of grey. He’d never been interested in it before but recently it seemed like such an interesting read. His phone suddenly buzzed, it was Kyle’s home phone, it was kinda weird Kyle was calling him from his home phone, his dad must have taken his cell phone. When Michael answered he was more than surprised to hear Mr Hill on the other line. “Michael, it’s Richard.” Michael was kind of stunned for a moment, he had always told Michael to call him Mr Hill. “Oh hi Richard! What’s up!” He said back enthusiastically. “I was just reading the newspaper and noticed the farmers market is tomorrow, I was wondering if you wanted to check it out with me?” To Michael this should’ve been really weird coming from Mr. Hill, but he was flattered Mr. Hill wanted to hangout with him. “That sounds lovely Richard! Can’t wait!” Michael said, smiling to himself. 

Michael carefully brushed his new soft bright hair in the bathroom mirror. Mr. Hill was going to be there in a hour and he hadn’t even picked out what he was going to wear. Michael noticed it was odd how Richard had gone from taking no interest in him to inviting him to hang out but he welcomed them, he needed something to do since Kyle had been so weird lately. Michael asked if Kyle was coming and Mr.Hill explained Kyle was busy and it would just be them. It didn’t really cross his mind hanging out with his best friend’s dad might be weird, but it felt like him and Mr. Hill were becoming just as good of friends. As he touched up his mascara he did a quick pose in the mirror to make sure his hair looked perfect. He’d elected on a floral print frilly top and a nice pair of jeans that Barb helped him pick out. He paired it with a nice new pair of booties that Barb just thought were perfect for a trip to the farmers market. For some reason when Michael informed Barb of his plans with Mr. Hill was giddy with excitement and forced Michael on a shopping spree and salon trip. 

The two walking through the farmers market at first was awkward, Michael didn’t really know how to connect with Richard. But Richard seemed to open up to him, he found out things he never knew about Richard before. He also never knew Richard was so funny and charming. He would let out a little giggle at almost everything he said. Before he knew it, Michael found himself holding hands with Richard. It should’ve felt weird, but it felt so perfect being interlocked with him. Richard even bought him a flower. Needless to say, what Michael thought was just hanging out ended up being the perfect first date. 

The following weeks Kyle avoided Michael at all costs. He did whatever he could to not see him, although Michael was hardly at school anymore, which was odd. Kyle was pretty sure he was spending most of his days with Barbara. All the avoiding had to end however when Kyle received a text one day inviting him to Michael’s birthday parties. Michael’s birthday parties were always a blast, it usually just involved playing video games all night but Kyle loved to go. He’d hoped Michael would be back to his old self at least a little bit at the party. 

Kyle was right at first, Michael seemed to be enjoying video games again. “Thank god you’re back dude.” Kyle gave him a pat on the back as he was in the middle of explaining his favorite Halo game. However he was interrupted by a knock on the door, “That must be him!” He skipped to the door giddy with excitement. The 5 boys in the living room didn’t know who it was, they didn’t know Michael invited someone else. They all peaked down the hallway to see Michael running his hands through his hair before he opened the door. “Hey you!” He gushed as he opened it. Standing on the other side was Richard Hill, Kyle immediately wanted to leave. He had a small bag in his hand, “Oh babe! You didn't have to get me anything!” gushed Michael. “Nonsense.” He said bending down and giving Michael a kiss on the cheek. “Open it sweetie.” He said handing Michael the bag.

“Ohmygosh! A trip to Hawaii?! Richie this is too much!” Michael put his long nails across his chest, he was flabbergasted. Nobody had bought him anything this expensive before. Richard smiled and rubbed Michael’s knee, “It’s never too much if it’s you, There’s more.” Michael scoffed again as he pulled out a small jewelry box. “Oh. My. Gosh” he lost his words as he pulled out a very elegant heart shaped diamond necklace. Michael just stared at it for a couple seconds. “Do you like it?” Richard asked nervously. Michael turned to his friend’s dad, “Aww. Of course hun, it’s perfect.” Kyle watched in horror as his best friend  stood up to embrace his father. The much smaller frame of Michael wrapped his arms around the 51 year old man’s head and gave him a quick peck on the lips, As he pulled away he rested his head on his chest briefly, “Thank you sweetheart. These gifts are the best.” Richard squeezed Michael’s tight little ass as they embraced. Michael’s friends watched in horror. Together they sat back down on the couch, this time Michael crossed his legs and placed his hands on Richards lap. Richard whispered something in his ear. Michael giggled quietly and nodded. “I think Richie is gunna take me to dinner, but thank you all so much for coming! It was so much fun!” All of Michael’s old friends walked out of the house stunned as what they just saw. Thay night Kyle could hardly sleep, there was a loud pounding coming from his dad’s bedroom.

More weeks passed, Kyle tried to turn a blind eye to what was happening but it was becoming increasingly difficult as his father’s relationship progressed. Michael didn’t really look like a Michael anymore, whenever he saw him his new blonde hair only got fluffier and fuller. His body was also somehow rapidly changing too, he was entirely skinnier, and he had an entirely new figure. One night Kyle was home playing video games when he heard a knock on the door. He opened it to see Michael, which caused his jaw to drop.

Michael had on a pair of black velvet booties that he paired with designer white skinny jeans that perfectly accented his new cute little figure. He finished off the look with a frilly leopard print top and of course the necklace Richard gave him. He was wearing heavy makeup, he wanted to look his best. He couldn’t stand the thought of someone seeing one of the blemishes on his face. He had a small black velvet bag slung over his shoulder, “Is your dad here?” He said to Kyle like nothing was different. Kyle looked Michael over multiple times, still not believing what he was seeing. “Dude…” was all he managed to say. Just a couple of weeks ago Michael would be standing in front of him in a stain covered shirt and sweatpants. The greasy haired overweight 18 year old not only looked like a woman… but a mature woman. His thick hips were cocked out as he laid his right hand on them. Michael heard his dad come down the stairs behind him, he turned to see his old man dressed in a nice pair of khakis and a dress shirt. His hair was slicked back and he smelt heavily like cologne. Kyle had never seen his dad so dressed up before, “There’s my cupcake!” He strolled past Kyle, he grabbed Michael by the hips and lifted him into his arms, Michael giggled loudly, “Well hey you!” He put his little arms around his man’s head as their lips met. Kyle gagged as he watched. As they pulled away Michael rubbed his hand across Richard’s chest, “My god honey this shirt makes you look handsome.” Richard smiled and turned to Kyle, “Don’t know when I’ll be home tonight boss, $20 is on the counter for pizza.” Kyle sighed, “Ok dad…” was all he said. Kyle watched as his father put his hand around Michael and rested it on his new tight little ass. He knew he had to find Barbara.

As Michael awoke from surgery Richard was standing over him with a bouquet of roses. “Wake up sleepyhead.” He smiled at Michael. Michael was still coming to, he had a hard time piecing together where he was. It took him a couple of seconds before his memory snapped into place, “Aw honey, you are so sweet.” A smile came to his face after he recognized Richard. Richard put the roses on the table, “Well… what do you think?!” He asked excitingly. It took Michael a second to realize what he was talking about, but once he did it sent chills down his spine. He removed the blanket over his bare chest, staring back at him were a pair of 2 form real breasts. They weren't anything extraordinary big or anything, but they were real. Michael rubbed his hand across his now mounded chest. He was staring at them but he couldn’t believe it. “Wow…” was all he could muster up at first. The realization hadn’t set in yet. “I feel… great.”

Not even a couple weeks after the surgery Michael was already showing off his new assets. He and Barb overhauled his entire wardrobe. He started exclusively wearing shirts that showed cleavage. He not only loved the looks he got but how much Richard loved it. His new favorite shirt was a frilly off the shoulder leopard print blouse that Barb found. It was just adorbs and really screamed his name. 

Soon enough Michael was no longer Michael. He was replaced by Monica Lewis, the 32 year old woman. Monica didn’t have a job, since she moved in with Richard he supported her. She was still waiting patiently for that engagement ring. She spent most of her days in yoga classes and out with Barb and the girls. Spending all the time around noisy wine drinkers it wasn’t long before Monica was a noisy wine drinker. 

Kyle’s life was different now. He was no longer the same person. Something about watching your best friend fall in love your father and becoming his dream woman would do that to a person. But Kyle was taking it as well as he could. He still couldn’t help but to check out his step mother everyday regardless, Monica was definitely a milf, and she knew it. Gradually her clothes became more and more revealing, when it wasn’t a pair of stretch pants and leather boots it was a dress or skirt, with matching wedges. She ran up the total’s on Richard’s credit card, it understandably frustrated him, but it all went away as soon as Monica put her hands on him. 

Every morning started the same for Kyle now. Waking up to smell of an amazing breakfast, then coming down stairs to see a dolled up Milf working in the kitchen. Today she was wearing a beautiful pink wrap dress that accented her figure perfectly. Monica had thickened up a bit since discovering that’s what Richard likes. She was still curvy, but got bigger breast implants and butt injections. She loved how she looked now but it was all for her man. Kyle hated how good Monica looked despite how fake she was.

His father came downstairs, with a brief glance at Kyle he turned all of his attention to the beautiful woman in the dress making breakfast. “Good morning you.” He said grabbed her by the waist from behind. Monica giggled like a little girl in her husband’s arms, “Oh hey sleepyhead, I missed you.” She gave him the warmest smile possible as she looked up him. Richard gave the little blonde trophy wife a warm smile back. Kyle turned his head in disgust as they made out in the kitchen. It almost like Kyle wasn’t there, they started slow but Richard practically had Monica shoved up against the counter, his hands rubbing her soft tits under her shirt. Kyle left for school, trying to get the image out of his head, but he was used to by now. It wasn’t all bad, he could see how happy Monica made his dad.

1 year later Monica Marie sat with her legs crossed underneath her as she was online shopping on the couch. She sipped her Chardonnay as she waited for Richard to get home. She usually wouldn’t be drinking wine this early, but tonight was date night and she was feeling… ready to have an entire night with Richard to herself. She had already bought the cutest pair of wedges and was looking for a matching romper when suddenly she heard the door open. In walked Richard, who unenthusiastically laid his bag on the table. The investment banker wore an expensive gray silk suit, his red tie was crooked. Monica loved the way he looked in suits, she loved the way he looked in anything, he was so handsome. “Welcome home sweetheart!” She wrapped her arms around his head and gave him a big kiss. “Missed you today. How was work?” Richard sighed as he held his wife closer, “It was a long one honey. I’m tired.” Monica let out a little smile, “Do you need to take some steam off?” She winked. “It’s okay babe you don’t hav…” before he finished his sentence Monica had already undid his belt. “But I missed you today.” She gave him a cute smile before lowering herself in front of her husband. As she did she placed her hand on Richard’s rod through his khaki’s. It was already hard as a rock. She rubbed her new acrylic nails across his crotch, his lips quivered as the arousal took over his body. She put her lips around the shaft, pushing it into her throat. She loved how the warm rod felt in her mouth. She sucked a lot louder than she had to, she wanted Richard to know how much she loved it. Richard moaned as he place his hand on the back of Monica's head. Monica moved her mouth deeper and deeper down the shaft each time, she knew she shouldn’t want it as much as she did. Richard’s moaned echoed through the living room, he couldn’t recall ever receiving a more satisfying blowjob, he couldn’t hold it any longer. Richard exploded, filling Monica’s mouth with his love juice. Not wanting to get any on her skirt she swallowed the milky love like a good girl. As Monica went to wash up Richard laid down on the couch and took a deep breath, “Wow.” Was all he said. Monica giggled and laid down elegantly on top of him, she intertwined his legs with hers and rest her head on his big chest.